(1S,2R,7R,10S,11S,14S,15S)-2,15-dimethyl-N-[2-(2H3)methyl(2H6)propan-2-yl]-5-oxo-6-azatetracyclo[8.7.0.02,7.011,15]heptadec-3-ene-14-carboxamide

• ChemBase ID: 168921
• Molecular Formular: C23H36N2O2
• Molecular Mass: 372.54414
• Monoisotopic Mass: 372.2776784
• SMILES: C1=CC(=O)N[C@H]2[C@]1([C@@H]1[C@@H](CC2)[C@H]2[C@](CC1)([C@H](CC2)C(=O)NC(C)(C)C)C)C
• Canonical SMILES: O=C1C=C[C@]2([C@H](N1)CC[C@@H]1[C@@H]2CC[C@]2([C@H]1CC[C@@H]2C(=O)NC(C)(C)C)C)C
• InChI: InChI=1S/C23H36N2O2/c1-21(2,3)25-20(27)17-8-7-15-14-6-9-18-23(5,13-11-19(26)24-18)16(14)10-12-22(15,17)4/h11,13-18H,6-10,12H2,1-5H3,(H,24,26)(H,25,27)/t14-,15-,16-,17+,18+,22-,23+/m0/s1
• InChIKey: DBEPLOCGEIEOCV-WSBQPABSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,7R,10S,11S,14S,15S)-2,15-dimethyl-N-[2-(^2H₃)methyl(^2H₆)propan-2-yl]-5-oxo-6-azatetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-3-ene-14-carboxamide
• IUPAC Traditional name: (1S,2R,7R,10S,11S,14S,15S)-2,15-dimethyl-N-[2-(^2H₃)methyl(^2H₆)propan-2-yl]-5-oxo-6-azatetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-3-ene-14-carboxamide
• Synonyms: (5α,17β)-N-(1,1-Dimethylethyl-d9)-3-oxo-4-azaandrost-1-ene-17-carboxamide; MK-906-d9; Proscar-d9; Prostide-d9; Finastid-d9; Finasteride-d9

Database IDs

• PubChem SID: 162263053
• PubChem CID: 25224489

CALCULATED PROPERTIES

• Acid pKa: 14.525358
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 3.0732863
• LogD (pH = 7.4): 3.0735092
• Log P: 3.073512
• Molar Refractivity: 108.196 cm^3
• Polarizability: 42.34966 Å^3
• Polar Surface Area: 58.2 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; DMSO; Methanol; n-Propanol
• Apperance: Off-White Solid
• Melting Point: 252-254°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - F342002

The labelled version of Finasteride. An inhibitor of 5α-reductase, the enzyme which converts testosterone to the more potent androgen, 5α-dihydrotestosterone. Antialopecia agent.

REFERENCES

• Koronkowski, M.J., et al.: Pharmacotherapy, 13, 309 (1993)
• Tenover, J.L., et al.: Clin. Ther., 19, 243 (1993)
• McConnell, J.D., et al.: N. Engl. J. Med., 338, 557 (1993)