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Merck
CN

SML1619

Tazarotenic acid

≥98% (HPLC), powder, retinoid receptor (RAR) agonist

Synonym(s):

6-(2-(4,4-Dimethylthiochroman-6-yl)ethynyl)nicotinic acid, 6-[2-(3,4-Dihydro-4,4-dimethyl-2H-1-benzothiopyran-6-yl)ethynyl]-3-pyridinecarboxylic acid, AGN 190299, AGN-190299, Tazarotene acid

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About This Item

Empirical Formula (Hill Notation):
C19H17NO2S
CAS Number:
118292-41-4
Molecular Weight:
323.41
UNSPSC Code:
12352106
PubChem Substance ID:
329825505
NACRES:
NA.77
MDL number:
MFCD00872121

Key Documents

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Product Name

Tazarotenic acid, ≥98% (HPLC)

SMILES string

CC1(C)CCSC2=C1C=C(C#CC3=CC=C(C(O)=O)C=N3)C=C2

InChI key

IQIBKLWBVJPOQO-UHFFFAOYSA-N

InChI

1S/C19H17NO2S/c1-19(2)9-10-23-17-8-4-13(11-16(17)19)3-6-15-7-5-14(12-20-15)18(21)22/h4-5,7-8,11-12H,9-10H2,1-2H3,(H,21,22)

assay

≥98% (HPLC)

form

powder

color

white to light brown

solubility

DMSO: 20 mg/mL, clear

storage temp.

2-8°C

Quality Level

100

Related Categories

Biochem/physiol Actions

Tazarotene is transformed to tazarotenic acid with the help of esterases. Tazarotenic acid regulates the pathogenic aspects of psoriasis through normalizing abnormal keratinocyte differentiation. It possesses strong anti-hyperproliferative effects in skin and reduces inflammation.
Tazarotenic acid, an active metabolite of tazarotene, is a potent and selective agonist of the retinoid receptor (RAR) that binds to RARα, RARβ, and RARγ. Tazarotenic acid relatively selective activates RARβ and RARγ. Tazarotenic acid is a first xenobiotic substrate of human retinoic acid hydroxylase CYP26A1 and CYP26B1.
Tazarotenic acid, an active metabolite of tazarotene, is a potent and selective agonist of the retinoid receptor (RAR).

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
0000426179
0000426179
0000232282
0000232283
0000226851

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Cytochrome P450 2C8 and flavin-containing monooxygenases are involved in the metabolism of tazarotenic acid in humans
Attar M, et al.
Drug Metabolism and Disposition, 31(4), 476-481 (2003)

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