(1S,2R,7R,10S,11S,14S,15S)-N-tert-butyl-2,15-dimethyl-5-oxo-6-azatetracyclo[8.7.0.02,7.011,15]heptadecane-14-carboxamide

• ChemBase ID: 134062
• Molecular Formular: C23H38N2O2
• Molecular Mass: 374.56002
• Monoisotopic Mass: 374.29332847
• SMILES: C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2C(=O)NC(C)(C)C)CC[C@@H]1[C@@]3(CCC(=O)N1)C
• Canonical SMILES: O=C1CC[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/C23H38N2O2/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/h14-18H,6-13H2,1-5H3,(H,24,26)(H,25,27)/t14-,15-,16-,17+,18+,22-,23+/m0/s1
• InChIKey: ZOIUUCNFVDJSJK-WSBQPABSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,7R,10S,11S,14S,15S)-N-tert-butyl-2,15-dimethyl-5-oxo-6-azatetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecane-14-carboxamide
• IUPAC Traditional name: (1S,2R,7R,10S,11S,14S,15S)-N-tert-butyl-2,15-dimethyl-5-oxo-6-azatetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecane-14-carboxamide
• Synonyms: Dihydroproscar; 3-Oxo-4-aza-5α-androstane-17β-(N-t-butylcarboxamide); (4aR,4bS,6aS,7S,9aS,9bS,11aR)-N-(1,1-Dimethylethyl)hexadecahydro-4a,6a-dimethyl-2-oxo-1H-indeno[5,4-f]quinoline-7-carboxamide; (5α,17β)-N-(1,1-Dimethylethyl)-3-oxo-4-azaandrostane-17-carboxamide; [4aR-(4aα,4bβ,6aα,7α,9aβ,9bα,11aβ)]-N-(1,1-Dimethylethyl)hexadecahydro-4a,6a-dimethyl-2-oxo-1H-indeno[5,4-f]quinoline-7-carboxamide; 1,2-Dihydrofinasteride; 3-Oxo-4-aza-5α-androstan-17β-carboxylic acid N-(tert-butyl)amide; N-(tert-Butyl)-3-oxo-4-aza-5α-androstane-17β-carboxamide; Dihydro Finasteride

Database IDs

• CAS Number: 98319-24-5
• MDL Number: MFCD00214352
• PubChem SID: 162228339; 24897969
• PubChem CID: 9864387

CALCULATED PROPERTIES

• Acid pKa: 14.546902
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 3.0756648
• LogD (pH = 7.4): 3.0756881
• Log P: 3.0756886
• Molar Refractivity: 107.1027 cm^3
• Polarizability: 42.590748 Å^3
• Polar Surface Area: 58.2 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: White Solid; yellow powder
• Melting Point: 276-278°C

Safety Information

• Storage Condition: Refrigerator
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Drug Control: regulated under CDSA - not available from Sigma-Aldrich Canada
• Storage Temperature: -20°C

Product Information

• Purity: ≥90%

DETAILS

Toronto Research Chemicals - D448975

The reduced product of Finasteride (F342000): a mechanism-based inhibitor of human prostate and skin steroid 5α-reductase. It forms an enzyme-bound NADP-dihydrofinasteride adduct during this inhibitory process.

REFERENCES

• Bull, H.G. et al.: Am. J. Chem. Soc., 118, 2359 (1996)
• Liang, T. et al.: Endocrinol., 117, 571 (1996)
• Ellsworth, K.P. et al.: J. Steroid Bioche. Mol. Biol., 66, 271 (1996)