ethyl 6-{2-[4,4-bis(2H3)methyl-3,4-dihydro-2H-1-benzothiopyran-6-yl]ethynyl}pyridine-3-carboxylate

• ChemBase ID: 178095
• Molecular Formular: C21H21NO2S
• Molecular Mass: 351.46194
• Monoisotopic Mass: 351.12929992
• SMILES: C1CSc2c(C1(C)C)cc(cc2)C#Cc1ncc(cc1)C(=O)OCC
• Canonical SMILES: CCOC(=O)c1ccc(nc1)C#Cc1ccc2c(c1)C(C)(C)CCS2
• InChI: InChI=1S/C21H21NO2S/c1-4-24-20(23)16-7-9-17(22-14-16)8-5-15-6-10-19-18(13-15)21(2,3)11-12-25-19/h6-7,9-10,13-14H,4,11-12H2,1-3H3
• InChIKey: OGQICQVSFDPSEI-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ethyl 6-{2-[4,4-bis(^2H₃)methyl-3,4-dihydro-2H-1-benzothiopyran-6-yl]ethynyl}pyridine-3-carboxylate
• IUPAC Traditional name: ethyl 6-{2-[4,4-bis(^2H₃)methyl-2,3-dihydro-1-benzothiopyran-6-yl]ethynyl}pyridine-3-carboxylate
• Synonyms: 6-[2-(3,4-Dihydro-4,4-(dimethyl-d6)-2H-1-benzothiopyran-6-yl-d2)ethynyl]-3-pyridinecarboxylic Acid Ethyl Ester; AGN 190168-d8; Tazorac-d8; Zorac-d8; Tazarotene-d8

Database IDs

• PubChem SID: 164234005
• PubChem CID: 71752332

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 5.218718
• LogD (pH = 7.4): 5.2187405
• Log P: 5.2187405
• Molar Refractivity: 97.882 cm^3
• Polarizability: 39.302673 Å^3
• Polar Surface Area: 39.19 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO
• Apperance: Light Brown Solid
• Melting Point: 103-104°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - T010052

Labelled Tazarotene (T010050). An acetylenic retinoid prodrug converted to the active metabolite, Tazarotenic acid, with selective affinity for retinoic acid receptors RARβ and RARγ. Antiacne; antipsoriatic. Used in treatment of photodamaged skin.

REFERENCES

• Tang-Liu, D.D.-S., et al.: Clin. Pharmacokinet., 37, 273 (1999)
• Roeder, A., et al.: Skin Pharmacol. Physiol., 17, 111 (1999)