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

• ChemBase ID: 168925
• Molecular Formular: C23H36N2O3
• Molecular Mass: 388.54354
• Monoisotopic Mass: 388.27259302
• 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(CO)(C)C)C)C
• Canonical SMILES: OCC(NC(=O)[C@H]1CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2CC[C@@H]2[C@]1(C)C=CC(=O)N2)(C)C
• InChI: InChI=1S/C23H36N2O3/c1-21(2,13-26)25-20(28)17-7-6-15-14-5-8-18-23(4,12-10-19(27)24-18)16(14)9-11-22(15,17)3/h10,12,14-18,26H,5-9,11,13H2,1-4H3,(H,24,27)(H,25,28)/t14-,15-,16-,17+,18+,22-,23+/m0/s1
• InChIKey: MFUJYZCMHDCXGQ-WSBQPABSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,7R,10S,11S,14S,15S)-N-(1-hydroxy-2-methylpropan-2-yl)-2,15-dimethyl-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)-N-(1-hydroxy-2-methylpropan-2-yl)-2,15-dimethyl-5-oxo-6-azatetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-3-ene-14-carboxamide
• Synonyms: (5α,17β)-N-(2-Hydroxy-1,1-dimethylethyl)-3-oxo- 4-azaandrost-1-ene-17-carboxamide; Finasteride 2-(2-Methylpropanol)amide

Database IDs

• CAS Number: 116285-36-0
• PubChem SID: 162263057
• PubChem CID: 15230776

CALCULATED PROPERTIES

• Acid pKa: 14.326564
• H Acceptors: 3
• H Donor: 3
• LogD (pH = 5.5): 2.026381
• LogD (pH = 7.4): 2.0265992
• Log P: 2.026602
• Molar Refractivity: 109.7397 cm^3
• Polarizability: 42.97321 Å^3
• Polar Surface Area: 78.43 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - F342020

A metabolite of Finasteride (F342000) (M-1 metabolite), an inhibitor of 5α-reductase, the enzyme which converts testosterone to the more potent androgen, 5α-dihydrotestosterone.

REFERENCES

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• Huskey, S., et al.: Drug Metab. Dispos., 23, 1126 (1992)
• Ishii, Y., et al.: Xenobio. Metabol. Dispos., 10, 197 (1992)
• Roylance, P., et al.: Biomed. Pharmacother., 49, 332 (1992)
• Lundahl, A., et a