(1S,2R,7R,10S,11S,14S,15S)-N-[2,5-bis(trifluoromethyl)phenyl]-2,15-dimethyl-5-oxo-6-azatetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-3-ene-14-carboxamide

• ChemBase ID: 70499
• Molecular Formular: C27H30F6N2O2
• Molecular Mass: 528.5297192
• Monoisotopic Mass: 528.22114753
• SMILES: N1C(=O)C=C[C@@]2([C@@H]3[C@@H](CC[C@@H]12)[C@@H]1CC[C@@H]([C@]1(CC3)C)C(=O)Nc1c(ccc(c1)C(F)(F)F)C(F)(F)F)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)Nc1cc(ccc1C(F)(F)F)C(F)(F)F)C)C
• InChI: InChI=1S/C27H30F6N2O2/c1-24-11-9-17-15(4-8-21-25(17,2)12-10-22(36)35-21)16(24)6-7-19(24)23(37)34-20-13-14(26(28,29)30)3-5-18(20)27(31,32)33/h3,5,10,12-13,15-17,19,21H,4,6-9,11H2,1-2H3,(H,34,37)(H,35,36)/t15-,16-,17-,19+,21+,24-,25+/m0/s1
• InChIKey: JWJOTENAMICLJG-QWBYCMEYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,7R,10S,11S,14S,15S)-N-[2,5-bis(trifluoromethyl)phenyl]-2,15-dimethyl-5-oxo-6-azatetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-3-ene-14-carboxamide; (1S,2R,7R,10S,11S,14S,15S)-N-[2,5-bis(trifluoromethyl)phenyl]-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: dutasteride; (1S,2R,7R,10S,11S,14S,15S)-N-[2,5-bis(trifluoromethyl)phenyl]-2,15-dimethyl-5-oxo-6-azatetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-3-ene-14-carboxamide; @dutasteride
• Synonyms: Dutasteride; Avidart; Avolve; Duagen; Dutas; Dutagen; Duprost; Dutasteride; Avodart; Dutasteride(Avodart)

Database IDs

• CAS Number: 164656-23-9
• MDL Number: MFCD00937869
• PubChem SID: 162036214
• PubChem CID: 6918296

CALCULATED PROPERTIES

• Acid pKa: 12.56134
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 5.7928166
• LogD (pH = 7.4): 5.7928147
• Log P: 5.7928176
• Molar Refractivity: 127.8962 cm^3
• Polarizability: 46.833355 Å^3
• Polar Surface Area: 58.2 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO

Safety Information

• Storage Condition: -20°C
• Storage Warning: IRRITANT
• TSCA Listed: false

Pharmacology Properties

• Target: 5-alpha-reductase
• Mechanism of Action: 5 alpha reductase inhibitor

Product Information

• Purity: 95+%
• Salt Data: Free Base
• Application(s): Under investigation for treatment of benign prostatic hyperplasia

DETAILS

Selleck Chemicals - S1202

Research Area: Prostatic intraepithelialn
Biological Activity:
Dutasteride is a 5-alpha-reductase inhibitor that inhibits the conversion of testosterone into dihydrotestosterone (DHT). It is used for the treatment of benign prostatic hyperplasia (BPH) and is prescibed off-label for the treatment of male pattern baldness (MPB). [1]Dutasteride inhibits both isoforms of 5-alpha reductase (5aR1 and 5aR2) to a similar extent (IC50 6nmol/l and 7 nmol/l, respectively), while finasteride only inhibits Type II. [2]Dutasteride competed for binding the LNCaP cell AR with an IC(50) approximately 1.5 µM. [3]References on Dutasteride[] TheProstate, 2004, 58:130^144

REFERENCES

• http://en.wikipedia.org/wiki/Dutasteride
• Bakshi, R.K. et al., J. Med. Chem., 1995, 38, 3189-3192; 1996, 39, 1192, (synth, pharmacol)
• Pat. Coop. Treaty (WIPO), 1995, Glaxo, 95 07 927; CA, 123, 56393f, (synth, pharmacol, cmr)
• Bramson, H.N. et al., J. Pharmacol. Exp. Ther., 1997, 282, 1496-1502, (hplc, pharmacokinet)
• Graul, A. et al., Drugs of the Future, 1999, 24, 246-253