Tazarotene

Names

[ Name ]:
Tazarotene

[Synonym ]:
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

Biological Activity

[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/RXR

Research 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.

[Related Small Molecules]

Retinoic acid | AM580 | Tamibarotene | Palovarotene | Fenretinide | TTNPB | Magnolol | AGN 194310 | AGN 193109 | CD437 | Adapalene | AR-7 | UVI 3003 | Tarenflurbil | AGN 195183

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

[ Storage condition ]:
Store at +4°C

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: US5675100

CHEMICAL NAME :: 3-Pyridinecarboxylic acid, 6-((3,4-dihydro-4,4-dimethyl-2H-1-benzothiopyran-6-yl )ethynyl)-, ethyl ester

CAS REGISTRY NUMBER :: 118292-40-3

LAST UPDATED :: 199801

DATA ITEMS CITED :: 3

MOLECULAR FORMULA :: C21-H21-N-O2-S

HEALTH HAZARD DATA

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

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

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%

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...

Related Compounds

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