SML1619

Tazarotenic acid

≥98% (HPLC)

• 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: 118292-41-4
• Molecular Weight: 323.41
• MDL number: MFCD00872121
• UNSPSC Code: 12352106
• PubChem Substance ID: 329825505

Properties

• Quality Level: 100
• 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

Description

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.

Safety Information

• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable