SML1619
Tazarotenic acid
≥98% (HPLC), powder, retinoid receptor (RAR) agonist
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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
Empirical Formula (Hill Notation):
C19H17NO2S
CAS Number:
Molecular Weight:
323.41
MDL number:
UNSPSC Code:
12352106
PubChem Substance ID:
NACRES:
NA.77
Recommended Products
Quality Level
Assay
≥98% (HPLC)
form
powder
color
white to light brown
solubility
DMSO: 20 mg/mL, clear
storage temp.
2-8°C
SMILES string
CC1(C)CCSC2=C1C=C(C#CC3=CC=C(C(O)=O)C=N3)C=C2
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)
InChI key
IQIBKLWBVJPOQO-UHFFFAOYSA-N
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.
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Certificates of Analysis (COA)
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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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