Hydroxycarboxylic acids: Educational and practical manual, page 6

Description and properties of the substance

Chenodeoxycholic acid has the property of dissolving gallstones. This is one of the most important bile acids for the body, produced in liver cells. Once in the gallbladder, it acts specifically on cholesterol stones, dissolving them, providing protection to the liver and the entire body from gallstone disease. In addition to dissolving stones, this acid reduces the amount of cholesterol synthesized in the liver. It follows that the bile becomes less saturated with it, so the formation of new cholesterol stones is minimized.

Deoxycholic acid

Deoxycholic acid

(eng.
deoxycholic acid
, or
deoxycholate
, or
cholanoic acid
, or
3α,12α-dihydroxy-5β-cholan-24-oic acid
) - bile acid, belonging to the so-called
secondary acids
, formed from primary bile acids in the colon under the influence intestinal microflora. The gross formula is C24H40O4. Molecular weight 392.57 g/mol. Deoxycholic acid will dissolve in alcohol and acetic acid. In its pure form it appears as a white or off-white crystalline powder.

Deoxycholic acid in the enterohepatic circulation of bile acids

Deoxycholic acid is formed from a conjugate of the primary bile acid - cholic, which enters the intestines of healthy people from the gallbladder, under the influence of anaerobic bacteria of the colon, where it is deconjugated by microbial choleglycine hydrolase and dehydroxylated with the participation of 7-alpha dehydroxylase.
The resulting deoxycholic acid binds to dietary fiber and is excreted from the body. Acidity in the intestinal lumen is of great importance. When the pH value increases, deoxycholic acid is ionized and well absorbed in the colon, and when it decreases, it is excreted. An increase in pH values ​​in the colon leads to an increase in the activity of enzymes leading to the synthesis of deoxycholic acid, its solubility and absorption and, as a result, an increase in the level of bile acids, cholesterol and triglycerides in the blood. One of the reasons for the increase in pH may be the lack of prebiotic components in the diet, which disrupt the growth of normal microflora, including bifidobacteria and lactobacilli (Lyalyukova E.A., Livzan M.A.). Part of the total volume of deoxycholic acid absorbed in the intestine returns through the portal vein with the blood to the liver (this process is called enterohepatic circulation of bile acids). In hepatocytes, deoxycholic acid is conjugated, binds with glycine or taurine, turning into glycodeoxycholic or taurodeoxycholic acid, and circulates further in the human body along with primary bile acids.

The damaging effect of deoxycholic acid on the mucous membrane

It is assumed that deoxycholic and other bile acids can penetrate the cells of the mucous membrane, being in a non-ionized lipophilic form, thereby causing a damaging effect.
This process is acid-dependent and more pronounced at acidic pH values. When studying the composition of duodenogastroesophageal reflux in patients with erosive esophagitis and Barrett's esophagus, it turned out that with a predominance of cholic, taurocholic and glycocholic acids, there was a significant amount of deoxycholic and taurodeoxycholic acid. In terms of toxicity (and hydrophobic properties), deoxycholic acid is superior to cholic, ursodeoxycholic and chenodeoxycholic acids, but inferior to lithocholic acid.

To reduce the damaging effects of deoxycholic acid on the mucous membrane of the stomach and esophagus, ursodeoxycholic acid preparations are prescribed. Ursodeoxycholic acid is a competitive inhibitor of deoxycholic and other bile acids at all levels of their physiological action: molecular, cellular, tissue and systemic. Due to the significant displacement of hydrophobic deoxycholic and other bile acids from the enterohepatic circulation, ursodeoxycholic acid reduces their potential toxicity to hepatocytes, the epithelium of bile canaliculi, the mucous membrane of the esophagus and stomach, increases the fluidity and reduces the lithogenicity of bile.

Deoxycholic acid as a non-surgical treatment for double chin

At the end of April 2020, the FDA registered the injectable prescription (Rx) drug Kybella, working name ATX-101, developed by Kythera Biopharmaceuticals (USA), the active ingredient of which is synthetic deoxycholic acid. Kybella is approved for use in adult patients to improve the appearance of moderate to severe thickening or enlargement of the submental fat layer. Deoxycholic acid destroys the cell membranes of the fatty tissue under the chin without affecting the adjacent tissue.

During each treatment session, the patient receives several injections of Kybella.
The session is carried out on an outpatient basis. Session duration is 15-20 minutes. The full course of treatment is 2-4, sometimes up to 6 sessions. Sessions are not held more often. than once a month. In 2020, deoxycholic acid, as an international nonproprietary name, was included in ATX, in “Section D. Drugs for the treatment of skin diseases”, in the group “D11A Other drugs for the treatment of skin diseases” and was assigned the code D11AX24.

On the website GastroScan.ru in the “Literature” section there is a subsection “Diseases of the hepatopancreatobiliary system”, containing publications for healthcare professionals on this topic.

general information

Deoxycholic acid is contained as an excipient in the hepatoprotective drug Essentiale N.
Deoxycholic acid has contraindications, side effects and application features; consultation with a specialist is necessary.

Back to section

Medicines

Preparations containing chenodeoxycholic acid:

1. Henofalk. The drug is from Doctor Falk Pharma GmbH, manufactured in Germany.
2. Henochol. Medicine from ICN GALENIKA. Country of origin: Serbia.
3. Hyeonosan. Medicine made by PRO.MED.CS Praha as in the Czech Republic.

Preparations from well-known imported manufacturers are high-quality and effective medicinal raw materials.

Classification of chemical reagents

Pure (“pure grade”) Glycolic acid Purpose grade. The content of the main component is 98% or higher (without impurities). The color of the stripe on the package is green. Pure for analysis (“analytical grade”, “analytical grade”) Glycolic acid, analytical grade. The content of the main component is higher or significantly higher than 98%. Impurities do not exceed acceptable limits for accurate analytical studies. The color of the stripe on the packaging is blue. Chemically pure (“reagent grade”, “chemically pure”) Glycolic acid, chemically pure. The content of the main component is more than 99%. The color of the stripe on the packaging is red. Extra pure (“special purity”) Glycolic acid, special purity grade. The content of impurities is in such small quantities that they do not affect the basic properties. The color of the stripe on the packaging is yellow.

Glycolic acid is an organic compound related to fruit acids. It is usually obtained from green grapes or sugar cane. It can also be synthesized artificially. Glycolic acid is designated by the formula C2H4O3 and has a number of unique properties that allow it to be used in various cosmetic procedures.

The compound is also included in many skin care products. Its high regenerating ability is noted. It not only cleanses the skin of the upper, dead layer, but also starts the process of renewal of dermal cells. After cleansing the epidermis, the skin is evened out, and its color and texture improve.

Application

The drugs are prescribed for gallstone disease with the presence of cholesterol stones up to 20 millimeters in diameter. In this case, the gallbladder must perform its function, that is, accumulate, concentrate and discharge bile when food enters the digestive system. Cholesterol stones are the most common formations of the bladder, since cholesterol becomes the basis of all stones formed in this organ. The use of the above drugs is a good alternative to surgical treatment of cholelithiasis.

Indications for use and benefits

This organic compound and preparations based on it can be used by all age categories of women. The effect is especially noticeable in middle-aged women with oily skin. In girls during puberty, the skin is especially sensitive and blackheads (acne) and pustular rashes associated with hormonal changes in the body often appear on the face. Therefore, drugs and procedures with glycolic acid can be prescribed to girls starting from 16 years of age. The main indications for cosmetic procedures with glycolic acid may be as follows:

• problematic skin with blackheads;
• enlarged pores;
• acne;
• aging skin;
• minor defects;
• age-related pigmentation;
• freckles.

People who are constantly exposed to ultraviolet radiation experience negative changes in the dermis on exposed parts of the body, especially on the face. This process is called photoaging. The use of drugs with acid will significantly reduce the effects of sunburn. Learn how to make a vitamin C mask at home at.

Instructions for chenodeoxycholic acid

Features of the use of drugs:

• "Henofalk" is used daily, once a day before bedtime. The dosage is 15 mg per kilogram of weight. The capsules are not chewed and washed down with water in the required amount. The maximum dose is 1.5 grams per day. Treatment is long-term - from three months to 3 years. Treatment should be carried out under ultrasound control, since the absence of a decrease in the diameter of the stones after six months serves as a reason to stop taking the medication.
• "Henochol" is used in a daily dose of 15-18 mg per kilogram of the patient's weight. The manufacturer recommends dividing the dose into three doses and taking one capsule in the morning and lunchtime, and 2 capsules in the evening. The maximum that can be taken per day is 1.5 grams. The duration of treatment depends on the size of the stones, but therapy should not be less than 6 months, and in cases where the stones reach 15-20 mm, you have to take the medicine for up to two years. Having measured the diameter of the stones using an ultrasound diagnostic device, after 6 months the feasibility of further taking Henochol is assessed. In case of successful dissolution of cholesterol stones in patients prone to increased stone formation due to metabolic characteristics, it is recommended to take the drug prophylactically for another month, one capsule per day, repeating the monthly course every 90 days.
• "Henosan" is used for oral administration, calculating the daily dose of 15 mg per kilogram of weight. On average, 3-6 capsules are obtained (no more than 1.5 grams per day), which are taken once in the evening. The capsules should be swallowed whole with the required amount of water. Treatment must be continued for 6 months to a year. The effectiveness of stone dissolution is assessed after six months using ultrasound. For preventive purposes, repeated courses are recommended after several months.

It is necessary to treat with drugs strictly according to the instructions for use of chenodeoxycholic acid.

Excerpt describing Glycolic acid

“God have mercy, you never need a doctor,” she said.
Suddenly a gust of wind hit one of the exposed frames of the room (by the will of the prince, one frame was always displayed with larks in each room) and, knocking off the poorly closed bolt, fluttered the damask curtain, and, smelling cold and snow, blew out the candle. Princess Marya shuddered; The nanny, having put down the stocking, went to the window and leaned out and began to catch the folded frame. The cold wind ruffled the ends of her scarf and the gray, stray strands of hair. - Princess, mother, someone is driving along the road ahead! - she said, holding the frame and not closing it. - With lanterns, it must be, doctor... - Oh my God! God bless! - said Princess Marya, - we must go meet him: he doesn’t know Russian. Princess Marya threw on her shawl and ran towards those traveling. When she passed the front hall, she saw through the window that some kind of carriage and lanterns were standing at the entrance. She went out onto the stairs. There was a tallow candle on the railing post and it was flowing from the wind. The waiter Philip, with a frightened face and another candle in his hand, stood below, on the first landing of the stairs. Even lower, around the bend, along the stairs, moving footsteps in warm boots could be heard. And some familiar voice, as it seemed to Princess Marya, said something. - God bless! - said the voice. - And father? “They’ve gone to bed,” answered the voice of the butler Demyan, who was already downstairs. Then the voice said something else, Demyan answered something, and footsteps in warm boots began to approach faster along the invisible bend of the stairs. "This is Andrey! - thought Princess Marya. No, this cannot be, it would be too unusual,” she thought, and at the same moment as she was thinking this, on the platform on which the waiter stood with a candle, the face and figure of Prince Andrei appeared in a fur coat with a collar sprinkled with snow. Yes, it was him, but pale and thin, and with a changed, strangely softened, but alarming expression on his face. He walked onto the stairs and hugged his sister. Name Glycolic acid Synonyms hydroxyacetic acid; CAS registration number 79-14-1 Molecular formula C 2 H 4 O 3 Molecular weight 76.05 InChI InChI=1S/C2H4O3/c3-1-2(4)5/h3H,1H2,(H,4,5) InChIKey AEMRFAOFKBGASW- UHFFFAOYSA-N SMILES C(C(=O)O)O EINECS 201-180-5

Contraindications

Contraindications to taking chenodeoxycholic acid drugs are:

• Stones whose size exceeds 20 mm.
• Stones with a powerful calcium frame.
• The gallbladder is clogged to capacity with stones and does not perform its function.
• Acute cholecystitis.
• Acute or chronic hepatitis of any nature.
• Acute inflammation of the bile ducts.
• Decompensation and end-stage cirrhosis.
• Presence of liver failure.
• Kidney failure.
• Blockage of the bile ducts with stones.
• Peptic ulcer of the stomach, duodenum during exacerbation.
• Malabsorption syndrome.
• Ulcerative colitis, enteritis.
• Pregnancy.
• Breast-feeding.
• Intolerance to the main substance or auxiliary components.

Release form of chenodeoxycholic acid

Medicines are produced in the following forms:

• "Henofalk" is produced in capsules with a dosage of 250 mg of active ingredient. Records of 25 pieces, packed in a box of two or four blisters.
• "Chenochol" is produced in capsules containing chenodeoxycholic acid in which is 250 mg. The capsules are sealed in blisters of eight pieces. The cardboard package contains seven blisters.
• "Henosan" is produced in capsules containing chenodeoxycholic acid 250 mg, blisters of ten capsules in a cardboard package of five pieces.

Side effects

Chenodeoxycholic acid preparations are usually well tolerated. Among the side effects, mild allergic reactions are possible, manifested in the form of a skin rash or itching. In patients taking large doses of the drug for a long time, it is possible that liver transaminases in a biochemical blood test may exceed the norm, which indicates a toxic effect of the drug on liver cells, where active metabolic transformations of the active substance occur.

A significant increase in ALT and ASAT requires a revision of dosages. Paroxysmal pain in the right hypochondrium (biliary colic) may occur when stones dissolved by the drug move. If the pain is short-term, then the medication continues without changes. Intestinal manifestations in the form of diarrhea appear with high doses and intensive dissolution of stones, which is accompanied by an increase in the fat content in the stool.

Products with C2H4O3

It is included in the following cosmetic products:

• peeling;
• cream;
• tonic;
• mask;
• cleansing gel;
• cleansing milk

Before using products with C2H4O3, you must consult a cosmetologist.

Peeling

Peeling products with glycolic acid have gained the most popularity in cosmetology:

1. Beauty Med peeling to eliminate rough wrinkles contains no more than 10% fruit acids, so it can be used independently at home. The drug evens out complexion, tightens pores and helps reduce expression lines and age wrinkles.
2. Peeling gel "Pleyana" is considered a gentle drug due to its low glycolic acid content. stimulates collagen production and gives a good lifting effect.
3. Neopeel Glycolic High Acid Series is for professional use only. Independent procedures are not allowed.
4. Peeling cream Glico-A from the French company IRIS can be used at home. cleanses and tightens pores, normalizes the functioning of the sebaceous glands and helps fight the signs of aging on the face.

Creams

• Glycolic Acid cream with birch sap is a delicate product for caring for problem areas of the body. In addition to the rejuvenating effect, this cosmetic product moisturizes and vitaminizes the skin.

Price: 900 rubles.

• Source Naturals is a blend of plant extracts and nutrients. The cream is intended for daily use in the evening.
• Collistar rejuvenating anti-aging cream with a pronounced tightening effect. Suitable for middle-aged women and intended for daytime use.
• Reviva Labs cream easily penetrates the skin, limits the appearance of wrinkles and gives the face a healthy complexion.
• A'PIEU Glycolic Acid Cream has no restrictions on skin type. It can be applied both morning and evening.
• Avne Cleanance K Cream-Gel cleanses pores, removes dead cells, mattifies the face and moisturizes the dermis.
• Anti-stretch mark cream Guam for body and chest with glycolic acid is suitable for body care during the postpartum period. The composition includes oils and scrubbing particles.

Emulsions and lotions

Lotions and emulsions with fruit acids are universal cosmetics. They can be used regardless of time of year and age.

• Academy exfoliant emulsion cleanses pores and smoothes out fine wrinkles. Apply in the evening after removing makeup.

Price: about 4500 rubles.

• Clinique Mild Clarifying Lotion removes old cells, moisturizes and soothes sensitive skin.