CAS 118292-40-3|Tazarotene
Introduction：Basic information about CAS 118292-40-3|Tazarotene, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
| Common Name | Tazarotene | ||
|---|---|---|---|
| CAS Number | 118292-40-3 | Molecular Weight | 351.462 |
| Density | 1.2±0.1 g/cm3 | Boiling Point | 499.8±45.0 °C at 760 mmHg |
| Molecular Formula | C21H21NO2S | Melting Point | 97-98ºC |
| MSDS | ChineseUSA | Flash Point | 256.1±28.7 °C |
Names
| Name | tazarotene |
|---|---|
| Synonym | More Synonyms |
Tazarotene BiologicalActivity
| Description | Tazarotene is a selective retinoic acid receptor (RAR) agonist for the treatment of plaque psoriasis and acne vulgaris. |
|---|---|
| Related Catalog | Signaling Pathways >>Metabolic Enzyme/Protease >>RAR/RXRResearch Areas >>Inflammation/Immunology |
| In Vitro | Tazarotene, in both gel and cream formulations, has been used both as monotherapy and as an adjuvant therapy. For psoriasis it has been combined with steroids, calcipotriene and phototherapy, and for acne, with antibiotics. Tazarotene has been shown to upregulate the tumor suppressor, tazarotene induced gene 3, which is overexpressed in psoriasis and skin cancer[1]. In human epidermal cell cultures, tazarotene suppresses the gene expression of 2 marker proteins, MRP-8 (calgranulin A) and SKALP (skin derived anti-leukoproteinase), highly elevated in psoriatic epidermis[2]. |
| In Vivo | Topical gel application provides direct delivery of tazarotene into the skin. At 10 hours after a topical application of 0.1% tazarotene gel to the skin of healthy individuals and patients with psoriasis, approximately 4 to 6% of the dose resides in the stratum corneum and 2% of the dose distributed to the viable epidermis and dermis. Tazarotene is designed to undergo rapid and complete metabolism to its active metabolite tazarotenic acid. Tazarotenic acid has a short systemic residence time and limited tissue distribution in animals[3].When topically applied, tazarotene blocks the induction of ornithine decarboxylase (ODC) activity by the tumour promoter 12-O-tetradecanoylphorbol 13-acetate (TPA) in the epidermis of the hairless mouse[3]. |
| References | [1]. Talpur R, et al. Efficacy and safety of topical tazarotene: a review. Expert Opin Drug Metab Toxicol. 2009 Feb;5(2):195-210. [2]. Nagpal S, et al. Negative regulation of two hyperproliferative keratinocyte differentiation markers by a retinoic acidreceptor-specific retinoid: insight into the mechanism of retinoid action in psoriasis. Cell Growth Differ. 1996 Dec;7(12):1783-91. [3]. Tang-Liu DD, et al. Clinical pharmacokinetics and drug metabolism of tazarotene: a novel topical treatment for acne and psoriasis. Clin Pharmacokinet. 1999 Oct;37(4):273-87. |
Chemical & Physical Properties
| Density | 1.2±0.1 g/cm3 |
|---|---|
| Boiling Point | 499.8±45.0 °C at 760 mmHg |
| Melting Point | 97-98ºC |
| Molecular Formula | C21H21NO2S |
| Molecular Weight | 351.462 |
| Flash Point | 256.1±28.7 °C |
| Exact Mass | 351.129303 |
| PSA | 64.49000 |
| LogP | 6.22 |
| Vapour Pressure | 0.0±1.3 mmHg at 25°C |
| Index of Refraction | 1.625 |
| InChIKey | OGQICQVSFDPSEI-UHFFFAOYSA-N |
| SMILES | CCOC(=O)c1ccc(C#Cc2ccc3c(c2)C(C)(C)CCS3)nc1 |
| Storage condition | Store at +4°C |
Toxicological Information
CHEMICAL IDENTIFICATION |
ACUTE TOXICITY DATA - TYPE OF TEST :
- LD - Lethal dose
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Rodent - rat
- DOSE/DURATION :
- >2 gm/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- REFERENCE :
- JAADDB Journal of the American Academy of Dermatology. (C.V. Mosby Co., 11830 Westline Industrial Dr., St. Louis, MO 63141) 1979- Volume(issue)/page/year: 37(Suppl),S25,1997 ** OTHER MULTIPLE DOSE TOXICITY DATA **
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Rodent - rat
- DOSE/DURATION :
- 22750 ug/kg/13W-I
- TOXIC EFFECTS :
- Musculoskeletal - other changes
- REFERENCE :
- JAADDB Journal of the American Academy of Dermatology. (C.V. Mosby Co., 11830 Westline Industrial Dr., St. Louis, MO 63141) 1979- Volume(issue)/page/year: 37(Suppl),S25,1997
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Primate - monkey
- DOSE/DURATION :
- 35 mg/kg/26W-I
- TOXIC EFFECTS :
- Musculoskeletal - other changes
- REFERENCE :
- JAADDB Journal of the American Academy of Dermatology. (C.V. Mosby Co., 11830 Westline Industrial Dr., St. Louis, MO 63141) 1979- Volume(issue)/page/year: 37(Suppl),S25,1997
Safety Information
| RIDADR | NONH for all modes of transport |
|---|---|
| HS Code | 2942000000 |
Customs
| HS Code | 2934999090 |
|---|---|
| Summary | 2934999090. other heterocyclic compounds. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0% |
Articles49
More Articles| A custom tailored model to investigate skin penetration in porcine skin and its comparison with human skin. Eur. J. Pharm. Biopharm. 95 , 99-109, (2015) Reliable models for the determination of skin penetration and permeation are important for the development of new drugs and formulations. The intention of our study was to develop a skin penetration m... | |
| Tazarotene versus tretinoin or adapalene in the treatment of acne vulgaris. J. Am. Acad. Dermatol. 43(2 Pt 3) , S51-4, (2000) The efficacy and tolerability of tazarotene 0.1% gel in the treatment of acne vulgaris have been compared with those of tretinoin 0.025% gel and adapalene 0.1% gel in multicenter, double-blind, random... | |
| Retinoic acid receptor signaling preserves tendon stem cell characteristics and prevents spontaneous differentiation in vitrox. Stem Cell Res. Ther. 7 , 45, (2016) Previous studies have reported that adult mesenchymal stem cells (MSCs) tend to gradually lose their stem cell characteristics in vitro when placed outside their niche environment. They subsequently u... |
Synonyms
| 3-pyridinecarboxylic acid, 6-[(3,4-dihydro-4,4-dimethyl-2H-1-benzothiopyran-6-yl)ethynyl]-, ethyl ester |
| Avage |
| Ethyl 6-[(4,4-dimethyl-3,4-dihydro-2H-thiochromen-6-yl)ethynyl]nicotinate |
| ethyl 6-[2-(4,4-dimethyl-2,3-dihydrothiochromen-6-yl)ethynyl]pyridine-3-carboxylate |
| 6-[(4,4-diméthyl-3,4-dihydro-2H-thiochromén-6-yl)éthynyl]pyridine-3-carboxylate d'éthyle |
| 6-[(3,4-Dihydro-4,4-dimethyl-2H-1-benzothiopyran-6-yl)ethynyl]-3-pyridinecarboxylic acid ethyl ester |
| Ethyl 6-((4,4-dimethylthiochroman-6-yl)ethynyl)nicotinate |
| Ethyl 6-[2-(4,4-dimethylthiochroman-6-yl)ethynyl] nicotinate |
| Tazorac |
| 3-Pyridinecarboxylic acid, 6-[2-(3,4-dihydro-4,4-dimethyl-2H-1-benzothiopyran-6-yl)ethynyl]-, ethyl ester |
| Tazarotene |
| Zorac |
| Ethyl-6-[(4,4-dimethyl-3,4-dihydro-2H-thiochromen-6-yl)ethinyl]pyridin-3-carboxylat |
| ethyl 6-[(4,4-dimethyl-3,4-dihydro-2H-thiochromen-6-yl)ethynyl]pyridine-3-carboxylate |
| MFCD00867628 |
