(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: 997
• Molecular Formular: C27H30F6N2O2
• Molecular Mass: 528.5297192
• Monoisotopic Mass: 528.22114753
• SMILES: FC(F)(F)c1c(NC(=O)[C@@H]2[C@@]3([C@H]([C@H]4C([C@@]5([C@H](NC(=O)C=C5)CC4)C)CC3)CC2)C)cc(cc1)C(F)(F)F
• Canonical SMILES: O=C1C=C[C@]2([C@H](N1)CC[C@@H]1C2CC[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-VYZSUTEISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (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
• IUPAC Traditional name: dutasteride
• Brand Name: Avodart
• Synonyms: dutasteride; Dutasteride

Database IDs

• CAS Number: 164656-23-9
• PubChem SID: 160964460
• PubChem CID: 152945

CALCULATED PROPERTIES

JChem

• Acid pKa: 12.56134
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 5.7926135
• LogD (pH = 7.4): 5.7928123
• 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

ALOGPS 2.1

• Log P: 5.45
• LOG S: -5.77
• Solubility (Water): 9.08e-04 g/l

PROPERTIES

Physical Property

• Hydrophobicity(logP): 6.8

DETAILS

DrugBank - DB01126

• Drug Groups: approved; investigational
• Description: Dutasteride belongs to a class of drugs called 5-alpha-reductase inhibitors, which block the action of the 5-alpha-reductase enzymes that convert testosterone into dihydrotestosterone (DHT). Finasteride also belongs to this group, but while dutasteride inhibits both isoforms of 5-alpha reductase, finasteride inhibits only one. Even so, a clinical study done by GlaxoSmithKline, the EPICS trial, did not find dutasteride to be more effective than finasteride in treating BPH. [Wikipedia]
• Indication: For the treatment of symptomatic benign prostatic hyperplasia (BPH) in men with an enlarged prostate gland to improve symptoms, and reduce the risk of acute urinary retention and the need for surgery.
• Pharmacology: Dutasteride is a synthetic 4-azasteroid compound that is a selective inhibitor of both the type 1 and type 2 isoforms of steroid 5 alpha-reductase (5AR), intracellular enzymes that convert testosterone to 5 alpha-dihydrotestosterone (DHT). Type I 5a-reductase is predominant in the sebaceous glands of most regions of skin, including scalp, and liver. Type I 5a-reductase is responsible for approximately one-third of circulating DHT. The Type II 5a-reductase isozyme is primarily found in prostate, seminal vesicles, epididymides, and hair follicles as well as liver, and is responsible for two-thirds of circulating DHT.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic. Extensively metabolized by CYP3A4 and CYP3A5 to active metabolites.
• Absorption: 60%
• Half Life: 5 weeks
• Protein Binding: Highly bound to albumin (99%) and α-1 acid glycoprotein (96.6%).
• Elimination: Dutasteride is extensively metabolized in humans. Dutasteride and its metabolites were excreted mainly in feces.
• Distribution: * 300 to 500 L
• References: Keam SJ, Scott LJ: Dutasteride: a review of its use in the management of prostate disorders. Drugs. 2008;68(4):463-85. [Pubmed] ; Shah SK, Trump DL, Sartor O, Tan W, Wilding GE, Mohler JL: Phase II study of Dutasteride for recurrent prostate cancer during androgen deprivation therapy. J Urol. 2009 Feb;181(2):621-6. Epub 2008 Dec 16. [Pubmed]
• External Links: Wikipedia; RxList; Drugs.com

REFERENCES

• Keam SJ, Scott LJ: Dutasteride: a review of its use in the management of prostate disorders. Drugs. 2008;68(4):463-85. Pubmed
• Shah SK, Trump DL, Sartor O, Tan W, Wilding GE, Mohler JL: Phase II study of Dutasteride for recurrent prostate cancer during androgen deprivation therapy. J Urol. 2009 Feb;181(2):621-6. Epub 2008 Dec 16. Pubmed