Salicylic acid: application, properties and derivatives. Salicylic acid Derivatives of salicylic acid have the effect

10.04.2022 Repair

MINISTRY OF EDUCATION AND SCIENCE OF THE RUSSIAN FEDERATION

FGAOU VPO

Immanuel Kant Baltic Federal University

MEDICAL FACULTY

Heterofunctional derivatives of benzene as

medicines

Performed:

Alexandrovich Yulia Alexandrovna

1st year student, 4A group.

Checked:

Myamina Maria Alekseevna

Kaliningrad

Heterofunctional derivatives of benzene as drugs

The inextricable link between chemistry and medicine is clearly manifested in the field of the creation and use of medicines. Back in the 16th century. The founder of iatrochemistry, Paracelsus, argued that "the real purpose of chemistry is not to make gold, but to make medicines." Since ancient times, biologically active organic compounds have been selected empirically, and the appearance of a number of drugs was often due to chance. Currently, all synthesized compounds must be tested for biological activity (biological screening). This is important for revealing the general patterns of the relationship between the structure of compounds and their biological activity. The “structure-property” problem serves as the foundation for the purposeful creation of effective drugs.

In recent decades, many new drugs have appeared. However, some groups of previously known drugs remain of great importance, in particular those with a benzene ring as a structural basis.

Benzene itself can cause acute and chronic poisoning. It has an irritating effect on the skin, its vapors in high concentrations cause excitation, respiratory distress.

Monofunctional derivatives of benzene in most cases also have pronounced toxic properties. Phenol, aniline, aromatic halogen derivatives serve as initial or intermediate products of the large-scale chemical industry. In this regard, it is necessary to take into account their toxic effect.

Benzoic acid. It is used in the form of sodium salt as an expectorant. In free form, benzoic acid is found in some resins and balms, as well as in cranberries, lingonberries, but more often

is contained in a bound form, for example in the form of an N-benzoyl derivative of aminoacetic acid, called hippuric acid. This acid is formed in the liver from benzoic and aminoacetic (glycine) acids and excreted in the urine. In clinical practice, the amount of hippuric acid in the urine of patients (after taking sodium benzoate) is used to judge the effectiveness of the detoxifying function of the liver.

OOPpantothenic acid in the human and animal body is part of coenzyme A (coenzyme A), which is involved in the implementation of such biochemical processes as oxidative decarboxylation of α-keto acids (pyruvate, α-ketoglutarate), β-oxidation and biosynthesis of higher fatty acids, synthesis steroid hormones, triacylglycerols, phospholipids, acetylcholine, hippuric acid, hemoglobin heme and others, acting as an intermediate acceptor and carrier of various acid residues (acyls) and forming the so-called acyl derivatives of coenzyme A (including acetyl-CoA, a key metabolite through which interaction between protein, carbohydrate and lipid metabolism).

i-Aminophenol and its derivatives. As a heterofunctional compound, p-aminophenol can form derivatives for each functional group separately and simultaneously for two functional groups. p-Aminophenol itself is poisonous; of interest to medicine is its derivative - paracetamol, which has an analgesic (pain reliever) and antipyretic effect.

The drug is used for headache, myalgia, neuralgia, arthralgia, for pain in the postoperative period, for pain caused by malignant tumors, to reduce fever during fever. It is well tolerated. At therapeutic doses, it rarely causes side effects. Possible skin (paracetamol is part of many combined drugs (Coldrex, Solpadein, Panadein, Citramon-P, etc.) allergic reactions.

Unlike acetylsalicylic acid, it does not have a damaging effect on the gastric mucosa and does not affect platelet aggregation (since it does not inhibit COX-1). The main disadvantage of paracetamol is a small therapeutic latitude. Toxic doses exceed the maximum therapeutic doses by only 2-3 times. In acute poisoning with paracetamol, serious damage to the liver and kidneys is possible. They are associated with the accumulation of a toxic metabolite - N-acetyl-p-benzoquinoneimine. At therapeutic doses, this metabolite is inactivated by conjugation with glutathione. At toxic doses, complete inactivation of the metabolite does not occur. The rest of the active metabolite interacts with cells and causes their death. This leads to necrosis of the liver cells and renal tubules (24-48 hours after poisoning). Treatment of acute poisoning with paracetamol includes gastric lavage, the use of activated charcoal, and the administration of acetylcysteine (increases the formation of glutathione in the liver) and methionine (stimulates the conjugation process). The introduction of acetylcysteine and methionine is effective in the first 12 hours after poisoning, until irreversible cell changes occur.

p-Aminobenzoic acid (PABA) and its derivatives . Esters of aromatic amino acids are capable of causing local anesthesia to one degree or another. This property is especially noticeable in para-derivatives. In medicine, anestezin (PABA ethyl ester) and novocaine (PABA 2-diethylaminoethyl ether) are used. Novocaine is used in the form of a salt (hydrochloride), which is associated with the need to increase its solubility in water.

Anestezin- one of the very first synthetic compounds used as local anesthetics. Despite more than 100 years of existence (synthesized in 1890; used since the late 90s), it is still relatively widely used alone and in combination with other drugs. Recently proposed a new aerosol preparation "Amprovizol" containing anestezin.

Anestezin is an active surface local anesthetic. Due to the difficult solubility in water, the drug is not used parenterally and for anesthesia during surgical operations. However, it is widely used in the form of ointments, powders and other dosage forms for urticaria, skin diseases accompanied by itching, as well as for pain relief of wound and ulcerative surfaces. Apply 5 - 10% ointments or powders and finished drugs ("Menovazin", "Amprovizol", etc.).

Novocaine(procaine hydrochloride) is an ester of diethylaminoethanol and para-aminobenzoic acid. In medical practice, it is used in the form of hydrochloride. It has a fairly pronounced anesthetic activity, but is inferior in this respect to other drugs. The duration of infiltration anesthesia is 30 min-1 h. The big advantage of novocaine is its low toxicity. This also applies to its metabolites. Novocaine does not pass well through the mucous membranes, therefore it is rarely used for surface anesthesia (sometimes it is used for these purposes in otorhinolaryngology in high concentrations - 10% solutions). Novocaine, unlike cocaine, does not constrict blood vessels. Their tone does not change or decreases somewhat, therefore, adrenomimetics (for example, adrenaline) are often added to novocaine solutions. By narrowing the vessels and slowing down the absorption of novocaine, adrenomimetics enhance and prolong its anesthetic effect, and also reduce its toxicity.

With a resorptive effect, novocaine has a predominantly depressing effect on the nervous system. It has moderate analgesic activity. In large doses, it can cause convulsions.

The effect of novocaine on the cardiovascular system is manifested by a hypotensive effect (the result of the inhibitory effect of the drug on the central nervous system and sympathetic ganglia), as well as a short-term antiarrhythmic effect (the effective refractory period and conduction time along the conduction system of the heart increase, excitability and automatism decrease).

In the body, novocaine is quickly hydrolyzed by plasma and tissue esterases. Its main metabolites are diethylaminoethanol and para-aminobenzoic acid. It should be borne in mind that the latter is a competitive antagonist of antibacterial agents from the group of sulfonamides. The conversion products of novocaine are excreted by the kidneys.

Salicylic acid and its derivatives. Salicylic acid belongs to the group of phenolic acids. As a compound with ortho functional groups, it decarboxylates on heating to form phenol.

Salicylic acid is moderately soluble in water, gives intense staining with iron(III) chloride, on which the qualitative detection of the phenolic hydroxyl group is based. Salicylic acid exhibits antirheumatic, antipyretic and antifungal effects, but as a strong acid (pKa 3.0) it causes irritation of the gastrointestinal tract and is therefore only used externally. Inside, its derivatives are used - salts or esters.

Salicylic acid is able to form derivatives for each functional group. Of practical importance are sodium salicylate, esters on the carboxyl group - methyl salicylate, phenyl salicylate (salol), and also on the hydroxyl group - acetylsalicylic acid (aspirin).

The listed derivatives (except salol) have analgesic, antipyretic and anti-inflammatory effects. Due to its irritant effect, methyl salicylate is used externally as part of ointments. Salol is used as a disinfectant for intestinal diseases and is notable for the fact that it does not hydrolyze in the acidic environment of the stomach, but decomposes only in the intestines. In this regard, salol is also used as a material for the protective shells of some drugs that are unstable in the acidic environment of the stomach.

Salicylic acid was first obtained by the oxidation of salicylaldehyde contained in the meadowsweet plant (genus Spireae). Hence its original name, spiric acid, with which the name aspirin is associated (the initial "a" stands for acetyl). Acetylsalicylic acid is not found in nature.

Of the other derivatives of salicylic acid, p-aminosalicylic acid (PASA) is of great importance as an anti-tuberculosis agent. PAS is an antagonist of p-aminobenzoic acid, necessary for the normal functioning of microorganisms.

Sulfanilic acid and its derivatives. Sulfanilic (p-aminobenzenesulfonic) acid exists as a dipolar ion.

Sulfanilic acid amide (sulfanilamide), known as streptocide, is the ancestor of a group of drugs with antibacterial activity called sulfonamides.

All sulfonamides contain a sulfonamide group -SO2NH2. Replacing it with other groups leads to a loss of antibacterial activity. It has been established that the amino group in the para-position must remain unsubstituted, and additional substituents cannot be introduced into the benzene ring, since they reduce the antibacterial activity of the compound.

The bacteriostatic effect of sulfonamides is based on the structural similarity with para-aminobenzoic acid (PABA), which is necessary for the vital activity of microorganisms. In environments where there is a lot of PABA (pus, a focus of tissue decay), sulfonamides are ineffective. For the same reason, they have little effect in the presence of procaine (novocaine) and benzocaine (anesthesin), which are hydrolyzed to form PABA.

Streptocid is one of the first antimicrobial drugs with a sulfanilamide structure, from which the name of this entire class came from. Currently not used due to low efficiency and toxicity.

In the search for effective antibacterial agents, more than 10,000 sulfanilamide derivatives have been synthesized. However, only a few dozen of them have found practical application. The most active are those derivatives in which the radical R has a heterocyclic nature.

List of used literature and information:

Bioorganic chemistry: a textbook by N. A. Tyukavkina, Yu. I. Baukov.

Pathophysiology: textbook: in 2 volumes / ed. V.V. Novitsky, E.D. Goldberg, O.I. Urazova. - 4th ed.,

Pharmacology: textbook. - 10th ed., corrected, revised. and additional - M.: GEOTAR-Media,

SULFANILAMIDES, L. S. Strachunsky, S. N. Kozlov. Guide for doctors

The site provides reference information for informational purposes only. Diagnosis and treatment of diseases should be carried out under the supervision of a specialist. All drugs have contraindications. Expert advice is required!

Salicylic acid - a descriptive characteristic

Salicylic acid known to many, it is often present in the home first aid kit. This drug brings a lot of benefits, but it is cheap. This pharmacological agent is used to treat many diseases, but, like any medical drug, it also has its own contraindications for use.

It was first obtained from the bark of the willow Salix L., and then the German chemist Kolbe managed to synthesize salicylic acid in a simple way, which is still used today. Initially, salicylic acid was used to treat rheumatism, but with the advent of modern antirheumatic drugs, it is used only as a topical agent. Refers to non-steroidal anti-inflammatory drugs.

Composition and form of release

The active substance is orthohydroxybenzoic acid.

The drug is available in the following dosage forms:

Salicylic acid 1% solution, 25 and 40 ml vials.
Salicylic acid 2% solution, 25 and 40 ml vials.
Salicylic ointment 2%, can 25 g
Salicylic acid alcohol solution 1%, bottles 25 and 40 ml.
Salicylic acid alcohol solution 2%, bottles 25 and 40 ml.
Salicylic acid alcohol solution 3%, bottles 25 and 40 ml.
Salicylic acid alcohol solution 5%, bottles 25 and 40 ml.
Salicylic acid alcohol solution 10%, bottles 25 and 40 ml.
Salicylic vaseline 1%, tube 30 ml.
Salicylic-zinc paste (Lassar paste), 30ml jar.

Salicylic acid is included in many combined products used externally: Diprosalik, Belosalik, Viprosal, Camphocin, Zinkundan, Lorinden A, in Klerasil lotions and creams, shampoos, tonics, gels, pencils and other forms.

Pharmacological action of drugs

Salicylic acid corresponds to the following formula: C 7 H 6 O 3 \u003d C 6 H 4 (OH) - CO 2 H. It is a representative of the group of aromatic hydroxy acids. In the neighboring positions of the benzene ring, it has an OH group, like in phenol, and a COOH group, like in benzoic acid. This compound is widely distributed in nature.

Salicylic acid is recommended for external use as a distracting, locally irritating, anti-inflammatory, keratoplastic, keratolytic, drying and antiseptic agent.

At a sufficient concentration, salicylic acid is able to coagulate microbial proteins. When applied, it has a pronounced effect on sensitive nerve endings. In addition, it improves trophism, reduces pain.

The tool has the ability to suppress the secretion of not only sebaceous, but also sweat glands. When using low concentrations, keratoplastic takes place, and high concentrations of the solution - keratolytic effect of the drug. Weak antimicrobial activity is noted.

Powders
In powders (2-5%), salicylic acid is used for excessive sweating of the legs, hyperhidrosis. Powder Galmanin contains 2 parts of salicylic acid, 10 parts of zinc oxide and 44 parts of talc.

Corn plaster "Salipod"
The patch is fixed on the skin and kept for two days. Repeated application is recommended until the corn disappears.

Persalan
Used as a hair conditioner. Represents a liquid. It is applied to the hair, the head is insulated with a towel. After 30 minutes, wash your hair with warm water. Used to treat oily seborrhea.

Salicylic acid derivatives

Salicylic acid preparations are used as classical antirheumatic agents. They have antipyretic, anti-inflammatory, analgesic effects.

When ingested, salicylic acid can cause irritation of the gastric mucosa, in connection with this, its sodium salt is more often used.

The agent is quickly excreted from the body through the kidneys, as well as sweat glands. Salts of Salicylic acid have low toxicity. However, due to the fact that salicylates are prescribed in very large doses in the treatment of rheumatism, they can cause side effects: shortness of breath, tinnitus, skin rashes.

Solutions of salicylic acid are practically incompatible with resorcinol, since in the case of their interaction, melting mixtures are formed. When interacting with zinc oxide, insoluble zinc salicylate is formed, so the use of salicylic acid with it is not recommended.

Side effects

With topical application of salicylic acid, burning, itching, hyperemia at the site of exposure may occur. Allergic reactions may occur, and individual intolerance to the active substance is rarely possible.

special instructions

It is not recommended to apply salicylic acid preparations to birthmarks, warts in the genital area or face, as well as hairy warts. When treating children, it is not recommended to treat several skin surfaces at the same time. Children under 3 years of age are not recommended to use salicylic acid preparations and its derivatives.

During pregnancy, the use of products containing salicylic acid is allowed for the treatment of corns only on a limited surface.

Mucous membranes must be washed with plenty of water if they get even a small amount of salicylic acid preparations.

It should be borne in mind that it is possible to increase the absorption of salicylic acid in certain skin diseases, especially those that occur with hyperemia, inflammation or weeping eczematous skin lesions: dermatitis, psoriasis, eczema, ichthyosis.

Application for various pathologies

Salicylic acid and its derivatives are used in the treatment of many diseases and various skin manifestations in various fields of medicine.

In dermatology

Salicylic acid and its preparations have a strong exfoliating effect on the skin, therefore they are successfully used in the effective treatment of simple acne. The action of the product is based on softening the upper layer of the skin and plugs of the follicles, which prevents the formation of comedones.

Most often, 1 and 2% alcohol solutions of salicylic acid, the so-called salicylic alcohol, are used. Higher concentrations of solutions for the treatment of acne and pimples are not used.

Salicylic acid is also used in the treatment of skin diseases. It is part of many finished medicines: creams, gels, shampoos, lotions. Means of the series "Clerasil", "Sebium AKN" are effective. Complex medical prescriptions for the treatment of skin diseases are popular.

Usually salicylic acid medicated preparations are used for rubbing from one (in the morning) to two times a day. When using low concentrations of solutions, side effects, such as irritation and hyperemia of the skin in the affected area, are not observed.

People with sensitive skin often experience dry skin caused by the action of salicylic alcohol. It is necessary to follow the basic rule: do not apply salicylic alcohol to the skin after cleansing it with alcohol lotions, gels, scrubs. It is also not recommended to use salicylic acid preparations together with benzoyl peroxide.

Treatment of warts with salicylic acid
To get rid of warts, the Salipod patch is used, which includes salicylic acid.

Application: stick a patch on the wart area for two days. Then it is removed. The wart is soaked in hot water, and its top layer is removed. This procedure is repeated several times until the warts disappear completely.

Instead of a patch, salicylic acid solution can be successfully used. They moisten the surface of the wart with a cotton pad, which can be left on the wart until completely dry. This procedure will have to be repeated more than once.

Elimination of age spots
Often, after squeezing acne, age spots remain on the skin, bringing a lot of tears to young girls. Psychological discomfort in this case often becomes the cause of self-doubt. At home, you can apply wiping the face with salicylic alcohol. Some prefer to visit a beauty salon. There, experts will help to eliminate age spots with the help of whitening masks based on salicylic acid and bodyagi.

salicylic acid for psoriasis
For the treatment of psoriasis, salicylic acid is used as a topical therapy.

In cosmetology

The extremely effective effect of salicylic acid on skin cells has long been proven. As already mentioned, it has anti-inflammatory, exfoliating and keratolytic effects, which allows it to be used in cosmetology.

Possessing the strongest antibacterial effect, salicylic acid is considered to be a thunderstorm of acne.

Salicylic acid is used to remove warts, corns, calluses, used against dandruff, acne. It can be found in many cosmetic products.

As you know, the use of salicylic acid has a number of advantages:

effectively helps against pimples, comedones, as it freely penetrates into the sebaceous glands, dissolves sebum;
improves skin regeneration;
does not affect the normal microflora of the skin;
slows down the aging process of the skin;
does not suppress the immune system;
suitable for problematic, sensitive and oily skin;
does not increase the photosensitivity of the skin;
cosmetics with salicylic acid can be used daily.

In cosmetology, peels with salicylic acid are often used. More often, the peeling composition includes two components: 7% salicylic acid and 45% glycolic acid, the PH level is 1.5.

Peeling is used for acne, photoaging, post-acne, seborrheic dermatitis, demodicosis.

Peeling is carried out by applying the mixture on the skin for several minutes, lightly massaging along the facial lines and removing it with a cotton pad. Finally, rinse the skin surface with warm water.

Salicylic acid preparations should not be used in children's cosmetics, with the exception of shampoos.

Preservative properties of salicylic acid

Salicylic acid is not an effective preservative, but its action is much stronger against yeast than it is against bacteria. As a preservative, salicylic acid has found application in various dermatological preparations, less often in cosmetic products.

There is information about the use of salicylic acid for domestic purposes as a preservative. Sometimes it is used in the manufacture of homemade preparations: compotes, canning

Salicylic acid, the use of which we will consider a little further, is a medication for external use. What this tool is for, and other information, we will consider in the materials of this article.

General information

Salicylic acid is a must have in your first aid kit. After all, this drug brings a lot of benefits, but it is inexpensive. For the first time, such a remedy was obtained from willow bark. After some time, the German chemist Kolbe synthesized salicylic acid in a simple way, thanks to which we can use it today.

Release form and composition

What is salicylic acid used for? The use of this drug is very extensive. As you know, its active ingredient is orthohydroxybenzoic acid. 1, 2, 3, 5 and 10% solutions, 2% ointments and pastes are made from this component. In addition, salicylic acid is very often included in the composition of combination preparations that are used externally (for example, Lorinden A, Belosalik, Diprosalik, Viprosal, Zinkundan, Camphocin, etc.).

pharmachologic effect

Salicylic acid is used externally as a local irritant, distraction, keratoplastic, anti-inflammatory, antiseptic, keratolytic and drying agent. At high concentrations, it is able to coagulate the proteins of microorganisms. During the use of such a drug has a pronounced effect on the nerve endings. Among other things, salicylic acid is able to improve trophism and reduce pain. This remedy suppresses the secretion of sweat and sebaceous glands. Like all anti-inflammatory nonsteroidal drugs, such a drug, as well as all its derivatives, has an antipruritic, vasoconstrictive and anti-inflammatory effect at the site of application.

Indications for use

Salicylic acid is actively used in the following pathologies:

hyperkeratosis and hyperhidrosis;
erythrasma;
inflammatory and infectious diseases of the skin;
eczema;
pityriasis versicolor;
pyoderma;
acne, getting rid of calluses, removing warts, corns and blackheads;
dermatitis;
burns;
ichthyosis;
psoriasis,
foot mycosis;
seborrhea and hair loss.

Salicylic acid: the use of the drug

Salicylic acid is used in the form of an ointment or solution only externally.

Features of use in rheumatism

The presented tool is quite often used as an additional component for the creation of classic antirheumatic drugs. As you know, such drugs have anti-inflammatory, antipyretic and analgesic effects. When ingested, salicylic acid causes severe irritation of the gastric mucosa. That is why its sodium salt is used for such cases. Such a remedy is very quickly excreted from the body through the sweat glands and kidneys. Salts of the presented acid are practically non-toxic. But due to the fact that salicylates are prescribed in high doses during the treatment of rheumatism, they can cause side effects such as shortness of breath, tinnitus, skin rash, etc.

Salicylic acid derivatives

Based on salicylic acid, the following drugs are produced:

Means "Aspirin", or acetylsalicylic acid. At temperature, this drug is very often used by patients.
Medication "Methyl salicylate", or methyl ether. This is a liquid that is used to treat neuralgic and rheumatic pains (intended for rubbing).
The drug "Phenacetin" (available in the form of powder and tablets). Combined with antipyretics.
Medication "Analgin". It is used orally and parenterally, that is, subcutaneously.
The drug "Antipyrin" (available in the form of tablets). Used in combination therapy.

Salicylic acid

Product chemical formula: C 7 H 6 O 3 / HOC 6 H 4 COOH

Trade designations of the product:

O-Hydroxybenzoic acid

Phenol-2-carboxylic acid

Salonil

2-Hydroxybenzoic acid

2-Hydroxybenzenecarboxylic acid

2-Carboxyphenol

O-Carboxyphenol

Product description:

Salicylic acid - white crystalline powder or needle-shaped crystals with a sweetish taste; Soluble in acetone, ether, alcohol, boiling water, benzene and turpentine, rarely soluble in chloroformbenzene, slightly soluble in water; Melts at 158°C. Form sodium salt (sodium salicylate) is conventional, derived primarily from sodium phenolate with carbon dioxide under heat and pressure. Salicylic acid contains both hydroxyl and carboxyl groups, which react with either acid or alcohol. The carboxyl group forms esters with alcohols; For example, methyl salicylate is formed with methanol, which is used in food flavorings and preservatives; Menthyl salicylate is formed with methanol, which is used in tanning lotions. The hydroxyl group reacts with acetic acid to form acetylsalicylic acid(so-called aspirin), which is the most common antiseptic and antipyretic. Phenyl salicylate (called salol) is formed by phenol, which is also used as an antiseptic and antipyretic. sodium salt (sodium salicylate), a shiny white powder, is used for antiseptic preparations and as a preservative. In addition to its analgesic and antipyretic properties, salicylic acid has keratinolytic properties and fungicidal properties. It and its derivatives are used in the treatment of hyperkeratosis, dandruff, ichthyosis and psoriasis, as well as in the treatment of fungal skin infections such as herpes zoster. Para-aminosalicylic acid (abbreviated PAS and PASA) is an analogue of para-aminobenzoic acid (abbreviated PABA), which inhibits the synthesis of folic acid in Mycobacterium tuberculosis and is bacteriostatic, inhibiting the growth and reproduction of tuberculosis bacillus. Para-aminosalicylic acid and its sodium salt (sodium p-aminosalicylate) are bacteriostatic against mycobacteria and are used to treat tuberculosis; Orally. Aminosalicylic acids are pharmaceutically active ingredients, including anti-infective agents against colds, flu and other viral infections. Mesalamine (5-aminosalicylic acid, abbreviated 5-ASA) is the active metabolite of sulfasalazine used to treat inflammation of the rectum and lower colon, mild to moderate ulcerative colitis proctosigmoiditis, and proctitis. Para-aminosalicylic acid (4-hydroxybenzoic acid) is used as a bacteriostatic agent intermediate, especially for arabens (alkyl esters of p-hydroxybenzoic acid), which are used in food and personal care products as a preservative. It is used in the production of liquid crystal polymers. It is also used as an intermediate in dyes, insecticides, pharmaceuticals, pesticides, and other chemical compounds. Salicylic acid and its derivatives are important in the preparation of other pharmaceutical products, dyes, flavors and preservatives. Topical keratolytic agents are beta-hydroxy acids such as salicylic acid.

If you heard about salicylic acid, chances are you know it as the main ingredient in aspirin. The chemical gets its name from the Latin term for willow, salix, because it was first made from a complex carbohydrate found in willow bark. There are some companies that make acne-care products claiming to contain salicylic acid from willow bark, but the compound is not found in the tree bark. Powdered bark must be treated with oxidizing agents and filtered to obtain acid. Salicylic acid is a very useful pain reliever. For a time, researchers even speculated that it might be a vitamin they called vitamin C. Inside the Body salicylic acid relieves pain and improves blood circulation. Applied to the skin, it breaks down fatty compounds such as oily sebum that can clog pores. In fact, it breaks down fats and fat-like compounds in the skin so well that it is generally believed that more than 2% is used for facial skin. salicylic acid, and 98% of the lotion is a neutral carrier. Until 3% salicylic acid can be used on other parts of the body and 10% to 30% will dissolve warts. Applying a soft solution salicylic acid directly on the skin provides many cleansing benefits without the risk of rupturing pores or damaging tiny blood vessels. However, treatment salicylic acid has many benefits not found in a simple cleaning procedure. Gently removing dead skin does more than just open pores. Salicylic acid increases cell turnover. This causes the skin to grow faster, opening up the pores. It increases the production of collagen, filling in the depressions in the skin and making it less "flexible". It removes discoloration from the skin, although it is often too strong for use on dark skin. Salicylic acid is the only beta hydroxy acid used in skin care. It performs the same skin care tasks as alpha hydroxy acids such as lactic acid and glycolic acid, but is used at a much lower concentration. Acne care products can contain up to 30% alpha hydroxy acids, but the same effect is achieved from 0.5% to 2%. salicylic acid. Similar to benzoyl peroxide salicylic acid is most effective only when used continuously, even after the acne has cleared. In the absence of an exfoliating and cleansing action salicylic acid the pores can become clogged again, leading to the return of blackheads. Salicylic acid also used in many acne treatments as combination therapy at low concentrations. The exfoliating effect of the acid enhances the effectiveness of other active ingredients. Because salicylic acid is effective at low concentrations, it is significantly less irritating than other products.

Chemical peel is a safe, effective and economical procedure for treating various skin conditions and improving appearance. Principle peeling involves controlled chemical damage to the skin to induce it to rejuvenate, resulting in smoother skin and improved surface texture. Chemical peel can be classified in different ways. A useful approach is to classify them according to the degree of skin damage, which determines the indications they can be used for treatment. Respectively, chemical peeling can be divided into three broad categories, i.e. superficial, medium depth and depth. Surface peelings cause damage to the epidermis and are therefore used to treat superficial conditions, including melasma, acne, and dyschromia. Medium depth peels penetrate the papillary dermis and are useful in the treatment of solar keratoses, dyschromias and pigment disorders. Deep peels cause necrosis down to the level of the reticular dermis, so they are indicated for deep wrinkles, severe photoaging, and deep scarring. Salicylic acid belongs to a group of compounds known as hydroxy acids, which are widely used for a number of cosmetic indications due to their many important properties. Its mechanism of action is desmolytic rather than a true keratolytic and its safety in dark-skinned people. Chemical peeling is the process of applying controlled chemical damage to the skin (partial or complete epidermis with or without dermis) by applying a chemical peel that causes the superficial layers of the skin to peel off, leading to the removal of superficial lesions, followed by the regeneration of new epidermal and dermal tissues. Salicylic acid is generally a safe compound when used in appropriate concentrations for the treatment of acne. However, one thing you may notice with salicylic acid based acne products is that sometimes they can leave your skin a bit dry. So it goes without saying that you should avoid any harsh cleansers and astringents when using salicylic acid based products. It's important to make sure you have a balanced acne treatment regimen, especially if you're using salicylic acid based products. Make sure you moisturize your skin regularly and use soothing products while using salicylic acid. Also, make sure you don't use salicylic acid for large areas of your skin, stick to areas that have pimples. If your skin is damaged, swollen, red, or infected, avoid using salicylic acid products.

Physical and chemical properties Salicylic acid.

	Indicators	Meaning
	State of aggregation Salicylic acid	crystalline powder
	Colour Salicylic acid	White to pale yellow
	Melting point Salicylic acid	158-161°C
	Boiling point Salicylic acid	211°C
	Density Salicylic acid	1,44
	Vapor density Salicylic acid
	Vapor pressure Salicylic acid	1 mmHg Art. (114°C)
	Solubility: Ethanol: 1 M at 20 °C	transparent, colorless
	Solubility in water	1.8 g/l (20°C)
	pH level Salicylic acid

Storage and transportation Salicylic acid.

Salicylic acid has the ability to break down lipids in the skin, causing symptoms ranging from dryness and irritation at low concentrations to mild acid burns at higher concentrations. If ingested in large quantities, it can cause salicylate intoxication, which can lead to very serious side effects.

Special storage is not required, salicylic acid can be stored in any clean container. Keep closed. Keep away from heat. Keep away from sources of ignition. Empty containers present a fire hazard, evaporate residues under a hood. Ground all equipment containing material. Do not swallow. Do not inhale dust. Wear appropriate protective clothing. In case of insufficient ventilation, wear suitable respiratory equipment. If swallowed, seek medical advice immediately and show container or label. Avoid contact with skin and eyes. Keep away from incompatible substances such as oxidizing agents, moisture.

Product Applications .

Salicic acid used as an anti-aging agent

Salicic acid used as a remedy for poisoning with certain poisons.

Salicic acid It is used as a remedy for removing warts and other skin defects.

Salicic acid used as a cosmetic biocide.

Salicic acid used as a denaturant.

Salicic acid used as an exfoliant.

Salicic acid used as an external analgesic.

Salicic acid used as a flavoring agent.

Salicic acid used as a skin conditioner.

Salicic acid used as a preservative.

Salicic acid used as an agent in hair conditioning products.

Salicic acid used as a solvent.

Salicic acid used as an agent in sun protection creams.

Salicic acid used in the manufacture of ultraviolet light absorbers.

Send your good work in the knowledge base is simple. Use the form below

Students, graduate students, young scientists who use the knowledge base in their studies and work will be very grateful to you.

Posted on http://www.Allbest.ru/

Introduction

Preparations of the salicylic acid group are classic antirheumatic agents. In addition to anti-inflammatory, they have a well-defined antipyretic and analgesic effect. The anti-inflammatory effect of salicylic drugs is not associated with an antimicrobial effect, but may depend on their ability to stimulate the release of adrenocorticotropic hormone from the anterior pituitary gland. This hormone, in turn, enhances the secretion of hormones of the adrenal cortex, which have a powerful anti-inflammatory effect.

Salicylic acid and its derivatives

Salicylic acid(CaK) is an aromatic phenolic hydroxy acid, the hydroxyl group of which is linked to the benzene ring.

It is a colorless crystalline substance, readily soluble in ethanol, diethyl ether, and poorly soluble in cold water (1.8 g/l at 20°C). Melting point 159 C, and boiling point - 211 C (20 mm Hg)

CaK has two acidity centers - a carboxyl and a phenolic hydroxyl group, and chemically behaves like a monohydric phenol and a monobasic acid (pK = 2.98).

When CaK interacts with strong bases, salts are formed both at the carboxyl group and with the participation of a weaker acid center - the phenolic hydroxyl group (Fig. 1.2 A).

CaK displaces weak acids from their salts, such as carbonic acid.

When the carboxyl group of CaK reacts with alcohols, esters are formed. This acid is also capable of forming ethers and esters due to the phenolic hydroxyl group; when it is acetylated with acetic anhydride, acetylsalicylic acid is formed.

food sources

In nature, CaK occurs as a glycoside of its methyl ester in essential oils of plants. Unripe fruits and vegetables are natural sources of salicylic acid, in particular blackberries, blueberries, melons, dates, grapes, kiwi, guava, apricots, green peppers, tomatoes, olives, radishes and chicory; also mushrooms. Some herbs and spices contain quite high amounts, while meat, poultry, fish, eggs, and dairy products contain little or no salicylates. Of legumes, seeds, nuts, and grains, only almonds, water chestnuts, and peanuts contain significant amounts of them.

The main industrial method for the synthesis of CaK and its derivatives) is the carboxylation of dry sodium phenolate by the action of CO2 at a pressure of 0.6 MPa, a temperature of 185C for 8-10 hours (Kolbe-Schmitt reaction) (Fig. 1).

CaA derivatives

Esters of salicylic acid and derivatives of salicylic acid amide can be assigned to this group. Salicylic acid forms esters both with organic acids (I) due to interaction with phenolic hydroxyl, and with alcohols or phenols (II) due to interaction with a carboxyl group. Salicylic acid amide derivatives have the general formula (III): (Fig. 2)

CaK and its derivatives - sodium salicylate, salicylamide, acetylsalicylic acid (AA), lysine acetylsalicylate, salol - are important medicinal substances. SaK is an antiseptic, irritant and keratolytic agent. It is part of the ointments, pastes, powders and solutions for the treatment of skin diseases and fungal diseases of the nails. CaK is also used as a preservative for some food products, an intermediate in the synthesis of dyes and fungicides. Sodium salicylate, salicylamide, acetylsalicylic acid, lysine acetylsalicylate are known as antipyretic, anti-inflammatory and analgesic agents; phenyl ether (phenyl salicylate, salol) - antiseptic; methisalicylate - an antirheumatic agent; p-aminosalicylic acid is an anti-tuberculosis drug.

Aspirin- acetylsalicylic acid - С6Н4(ОСОСН3)СООН - is widely used as an antipyretic and analgesic agent. In some countries, it is widely used for the treatment of rheumatism. In the gastrointestinal tract, aspirin is partially saponified to form salicylic and acetic acids. Part of it is absorbed unchanged. Acetylsalicylic acid, as an ester formed by acetic acid and phenolic acid (instead of alcohol), is very easily hydrolyzed. Already when standing in moist air, it hydrolyzes into acetic and salicylic acids. In this regard, pharmacists often have to check whether acetylsalicylic acid has been hydrolyzed. For this, the reaction with FeCl3 is very convenient: acetylsalicylic acid does not give color with FeCl3, while salicylic acid, formed as a result of hydrolysis, gives a violet color.

Methyl salicylate- methyl ester of salicylic acid - is a liquid that is well absorbed by the skin. It is used as an external rubbing agent in the treatment of rheumatic and neuralgic pains, often in combination with other remedies. Methyl salicylate has both local and resorptive effects. (Fig. 3)

Salicylamide(like salicylic acid) sublimates when heated. Salicylamide is slightly soluble, osalmide is practically insoluble in water. Salicylamide is soluble in ethanol, sparingly soluble in ether, slightly soluble in chloroform. Osalmid is easily soluble in ethanol and alkali solutions, sparingly soluble in ether. (Fig. 4)

Phenyl salicylate, or salol, was first obtained by our compatriot M.V. Nenetsky. Phenyl salicylate is a crystalline powder, very poorly soluble in water. Has free phenolic hydroxyl. Due to the low solubility in water in aqueous solutions, it does not give a staining reaction with FeCl3, however, its alcoholic solutions are stained purple with FeCl3. Phenyl salicylate hydrolyzes slowly. In medicine, it is used as a disinfectant for certain intestinal diseases. Its action is associated with hydrolysis and the release of salicylic acid and phenol. Phenyl salicylate is used to cover pills in cases where they want the medicinal substances to pass unchanged through the stomach and show their effect in the intestines: phenyl salicylate, which is generally slowly hydrolyzed, is only hydrolyzed to a very small extent in the acidic contents of the stomach and therefore the pill shells from it disintegrate sufficient only in the intestines.

Of the other derivatives of salicylic acid, p-aminosalicylic acid (PASA) is of greater importance. It is synthesized by carboxylation, like salicylic acid. The starting compound in this case is m-aminophenol.

PAS has an anti-tuberculosis effect and is used in the form of a sodium salt. Other isomers of this acid do not have such actions, and m-aminosalicylic acid, on the contrary, is a highly toxic substance. The anti-tuberculous effect of PAS is explained by the fact that it is an antagonist of p-aminobenzoic acid, which is necessary for the normal functioning of microorganisms.

Preparations Sak

salicylate analgesic antipyretic

Phenacetin(Phenacetinum), FVIII. White crystalline powder or scaly crystals, odorless, slightly bitter in taste, almost insoluble in water. It is used orally in powders or tablets of 0.25-0.5 g per reception 1-3 times a day, depending on the indications. Often combined with other antipyretics or sedatives, as well as caffeine.

Antipyrine(Antipyrmum), FVIII (B). White crystalline powder, odorless, slightly bitter taste, highly soluble in water. It is used orally in powders or tablets of 0.25-0.5 g 1-3 times a day. Often used in combination with other agents. To stop bleeding, it is applied externally in 10-20% solutions.

Higher doses: 1 g (3 g).

Pyramidon(Pyramidonum), FVIII (B). White crystalline powder, odorless, bitter taste, soluble in water. It is used orally in powders and tablets of 0.25-0.5 g 1-3 times a day. Often combined with other drugs. Its combination with veronal (1 mol: 2 mol) is called verodona.

Analgin(Analginum), FVIII (B). White crystalline powder, odorless and tasteless, soluble in water. Analgin solutions are unstable during storage. It is used orally in powders or tablets of 0.3-0.5 g and parenterally (subcutaneously, intramuscularly or intravenously) 0.5 g 1-3 times a day.

Higher doses: 1 g (3 g).

Butadion(Butadionum) (B). White crystalline powder with a slight aromatic odor and slightly bitter taste, almost insoluble in water, soluble in alkalis. It is used orally in powders or tablets of 0.15 g 4 times a day during the main course of treatment. Maintenance doses are 0.1-0.2 g per day. The sodium salt of butadione can be used for intramuscular injections, although they are somewhat painful. A solution containing sodium salt of butadione and pyryramidone in equal amounts is convenient for injection.

sodium salicylate(Natrium salicylicum), FVIII. White crystalline powder or flakes, odorless, sweetish-salty taste, highly soluble in water. The drug is taken orally in powders, tablets or solutions, and is also administered intravenously in 10-15% solutions. A single dose of sodium salicylate is 0.5-1 g, the daily dose in the initial period of treatment of rheumatism can be 8-10 g. Subsequently, the dose is reduced. The total duration of treatment varies.

Biological action of salicylates

Salicylates are non-steroidal anti-inflammatory drugs that have antipyretic (antipyretic), analgesic, and anti-inflammatory effects, and aspirin also has antiplatelet (reduces platelet aggregation) and anti-gout effects.

The main mechanism of action of salicylates as pharmacological agents is irreversible inactivation by acetylation of both COX isoforms, a key enzyme in the synthesis of prostaglandins, prostacyclins and thromboxane from arachidonic acid.

It is assumed that the anti-inflammatory effect of AA and other salicylates is not limited to the effect on the prostaglandin system. Thus, acetylated COX-2 can form 15-R-hydroxyeicosatetraenoic acid, which is converted by 5-lipoxygenase into 15-epilipoxin A4, which has a powerful anti-inflammatory effect and enhances the effect of salicylates. In addition, salicylates reduce the activity of hyaluronidase and limit the energy supply of the inflammatory process by inhibiting the formation of ATP.

It is known that high doses of salicylates inhibit the contraction of striated muscles, and AA inhibits the spasmodic effect of prostaglandins on smooth muscles.

The negative effect of salicylates on the body is associated with their inhibitory effect on the isoform of the COX enzyme - COX-2. These side effects include ulcerogenic effects (the appearance of stomach ulcers and gastric bleeding), drug-induced liver damage (a rare complication in the form of hepatitis or liver failure), Reye's syndrome.

The ulcerogenic effect of aspirin is due to the inhibition of blood coagulation factors and inhibition of the synthesis of prostaglandin E1, which has a cytoprotective effect on the gastric mucosa, and the CaK formed during its decay inhibits the intestinal microflora.

Reye's syndrome is an acute encephalopathy in combination with fatty degeneration of the liver and other internal organs that occurs after taking AK or other salicylates for viral infections (influenza, chicken pox, hepatitis A, AIDS), without treatment ends in death. This disease affects children aged 4 to 16 years. The pathogenesis of Reye's syndrome is associated with damage to mitochondria that occurs under the influence of salicylates and viral infection.

In view of the side effects of salicylates described above, the creation of new dosage forms and agents based on CaA and aspirin, devoid of their negative effects, is an important area of modern pharmacology. Some authors point out that CaK derivatives with transition metals may have a number of beneficial pharmacological properties. At the same time, they do not cause side effects that are characteristic of CaC, and in a number of other studies it was noted that the anti-inflammatory effect of cobalt, zinc, and copper salicylates is much higher than that of CaC.

Hosted on Allbest.ru

...