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13-cis-Retinoic Acid CAS 4759-48-2 Isotretinoin

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  • Appearance: Yellow to organic powder
  • Purity: 99. 0%min
  • Stock: In stock
  • Sample: Available
  • Zhishang Chemical: 13-cis-Retinoic Acid Supplier & Manufacturer

Basic Info

What is 13-cis-Retinoic Acid?

Isoteritonin, also known as 13-cis-retinoic acid, the trade name is Thales, and the chemical name is 3,7-dimethyl-9-{2,6,6-trimethyl-1 A cyclohexene-1-base}-2 cis-4 trans-6 trans-8 trans-nonatraenoic acid. Oral administration of this drug has a significant effect on nodular cysts and acne conglomerates, and is the drug of choice for severe acne or cicatrix acne that is not well treated with antibiotics. It has a remarkable curative effect in the treatment of skin diseases, tumors, recurrent pediatric respiratory tract infections and other diseases, and has a good prospect in clinical application.

Isotretinoin is a bright red or orange flaky crystal with a melting point of 174~175°C. It is hardly soluble in water but soluble in organic solvents such as ethanol and isopropanol. It is easy to oxidize and is very sensitive to light below 500nm, trace metals, strong acids, and high heat.

After β-ionone reacts with ethylmagnesium chloride, it reacts with triphenylphosphine to form a triphenyl salt, and then reacts with cyclopentenone derivatives to generate isotretinoin and its 8Z isomer. After its 8Z isomer is separated, it is isomerized into isotretinoin by the action of palladium nitrate.

13-cis-Retinoic Acid Uses

  • 13-cis-Retinoic acid has the functions of shrinking sebaceous glands, inhibiting the activity of sebaceous glands, and reducing the secretion of sebaceous glands, thereby inhibiting the reproduction of Propionibacterium acnes, which relies on the growth of lipid environment.
  • 13-cis-Retinoic acid has anti-keratinization, inhibits excessive proliferation of epidermal cells and promotes their differentiation, and can reduce keratinization of hair follicle orifices and sebaceous ducts.
  • It can also affect the function of monocytes and lymphocytes, inhibit the chemotaxis of neutrophils and have anti-inflammatory activity.
  • Selectively bind to retinoic acid nuclear receptors to play a therapeutic role. Inhibits the proliferation of Brevi Corynebacterium acnes, has immunostimulatory effect at low doses, and immunosuppressive effect at high doses.
  • 13-cis-Retinoic acid can inhibit the formation of collagenase and gelatinase in the skin, and can inhibit the activity of ornithine decarboxylase. Because the induction of ornithine decarboxylase can play a major role in skin mutations, isotretinoin can also inhibit tumorigenesis.
  • When used topically, the mechanism of action of this product is similar to that of tretinoin, which can induce epidermal cell proliferation, promote the differentiation of epidermal granule layer into stratum corneum, and regulate the horny plug in the process of abnormal keratinization of pilosebaceous epithelium, thereby exerting a therapeutic effect.

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Clinical Treatment of Isotretinoin for 6 Skin Diseases

Isotretinoin belongs to oral retinoic acid drugs, which can play a role in the four key pathophysiological links of acne. It has the effects of significantly inhibiting sebaceous gland lipid secretion, regulating abnormal keratinization of pilosebaceous gland ducts, improving the anaerobic environment of hair follicles to reduce the propagation of Propionibacterium acnes, and anti-inflammatory and preventing scar formation.

Acne is a chronic inflammation of hair follicles and sebaceous glands, which mostly occurs during puberty and affects the appearance of the skin. The actual etiology is not very clear, and it may be related to increased secretion of secretory glands, hyperkeratosis of hair follicles, abnormal flora and inflammation. Isotretinoin can inhibit the proliferation of keratinocytes, prevent keratin embolism, inhibit sebaceous gland secretion and sebum production, and make acne lesions subside. It can inhibit the secretion of sebum, stimulate the conversion of thickened epithelial cells, and reverse abnormal horny It has a significant effect on the treatment of acne and has become the first choice drug for acne treatment. Isotretinoin can regulate cell proliferation, differentiation and apoptosis in the epidermis, has anti-proliferation, repair and exfoliation effects, and has anti-inflammatory and immunoregulatory effects.

The biggest feature of palmoplantar keratoderma is the symmetry, diffuse keratosis, and hypertrophy in the palms and soles of the feet. Most of them start from infants, and the skin is pale yellow due to hyperkeratosis. General patients are often accompanied by hyperhidrosis. Due to keratinization and hypertrophy, chapping is prone to occur in winter, and the most serious type is mutilated palmoplantar keratoderma. Due to severe keratosis, hypertrophy and proliferation, the foot is deformed and disabled. Isotretinoin can bidirectionally regulate the growth, differentiation and repair of epithelial cells and other cells, and normalize the process of keratinization and differentiation; it can normalize the distribution of Langerhans troupes in the skin, and has a direct effect on the immune system Regulatory effect; reduces neutrophil migration from dermis to epidermis and alters adhesion between target cells.

The clinical manifestations of seborrheic dermatitis are scalp itching, greasy scales and papules of various sizes, and the papules are covered with greasy scales or scabs, including greasy scalp on the top of the head, progressive soft, sparse hair, and increased shedding . The etiology of seborrheic dermatitis is not completely clear. Most studies believe that there is excessive seborrhea, accompanied by inflammation secondary to abnormal keratinization of the epithelium of the hair follicle orifice. Isotretinoin can inhibit the activity of sebaceous glands, reduce sebum secretion, improve abnormal keratinization of epithelial cells, and has anti-inflammatory effects.

It is generally believed that the mechanism of isotretinoin in the treatment of psoriasis is: 1. It can normalize the hyperkeratotic epidermis of psoriasis, regulate the proliferation and differentiation of lesion skin; 2. Activate macrophages and epidermal Langerhans cells, Adjust the inflammatory response and immune response in the lesion; 3. Reduce the activity of polyamine synthetase, so that the biochemical metabolic process in the body returns to normal; 4. Inhibit keratinocytes and inhibit the DNA of hyperactive epidermal keratinocytes in patients with psoriasis And RNA synthesis, inhibit the formation of vascular endothelial cell growth factor and cell adhesion molecules in patients.

Primary cutaneous amyloidosis is a common metabolic disorder skin disease. Its pathogenesis is not fully understood, and it is generally believed to be related to genetics, metabolic disorders and immune responses. Isotretinoin can regulate the mitosis of epidermal cells, inhibit the production of keratin, and restore the hyperplasia and differentiation of lesioned skin to normal.

Adverse reactions of isotretinoin: dry skin, cheilitis, desquamation, itching, pain, rash, increased skin fragility, peeling of palms and soles, ecchymosis, secondary infection, etc. Women of childbearing age who desire to have children must take contraceptive measures for 2 years. Corresponding countermeasures can be taken for the above adverse reactions, such as dry skin and mucous membranes, external use of moisturizers, eye drops and no contact lenses for conjunctivitis, avoid ethanol (alcoholic) beverages and alcohol, low-fat diet, and adjust if necessary Dosage.

Clinical Application of 13-cis-Retinoic Acid

Isotretinoin is an effective medicine for treating acne. It contributes in the 4 web links of acne pathogenesis as well as protects against the development of acne skin lesions:

  1. Hinder the secretion of sebaceous glands.
  2. Hinder the development of acne bacillus.
  3. Restraint of sebaceous gland hyperplasia.
  4. Anti-inflammatory impact.

Isotretinoin has no affinity with retinoic acid receptors, and the exact device of its action is not really clear. The anti-acne effect of isotretinoin may be related to its or its metabolites’ capacity to inhibit the expansion and differentiation of sebaceous glands. Decreased sebaceous gland volume is related to minimized cutaneous DHT and downregulation of cutaneous androgen receptors. Other devices consist of minimizing keratinization of hair roots, anti-bacterial results, and also anti-inflammatory impacts.

In the 1980s, isotretinoin was utilized only in serious nodular cystic acne. Now isotretinoin is also used in some much less extreme acne. These patients are usually aloof to traditional therapy, particularly some In people who have actually utilized antibiotics for a long period of time, acne bacilli have created resistance to multiple drugs (such as erythromycin, tetracycline). It can likewise be made use of in the treatment of some acne individuals who are prone to scarring.

Reference

  1. Isotretinoin – WikiPedia
  2. Luo Ying. Research progress of isotretinoin and its clinical application[J]. Journal of Zhejiang Ocean University (Natural Science Edition), 2006(04):457-460.

13-cis-Retinoic Acid Supplier and Manufacturer

As a 13-cis-retinoic acid supplier and manufacturer with a strict standard product quality system certificate, Zhishang Chemical has long been providing the best 13-cis-retinoic acid raw materials to customers all over the world.

Over the years, relying on professional team experience and customer-centric team concept to meet customer needs in a timely manner, our company enjoys a high reputation in the world. At present, our company has served more than 6,000 customers and has established long-term cooperative relations with customers from many countries.

If you have a demand for 13-cis-retinoic acid and related products, please contact our service staff Zhishang Chemical – White directly, and we will provide you with high-quality products at the best price.

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