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(1S,2R,7R,10S,11S,14S,15S)-N-tert-butyl-2,15-dimethyl-5-oxo-6-azatetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-3-ene-14-carboxamide
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ChemBase ID:
1086
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Molecular Formular:
C23H36N2O2
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Molecular Mass:
372.54414
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Monoisotopic Mass:
372.2776784
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SMILES and InChIs
SMILES:
O=C(NC(C)(C)C)[C@@H]1[C@@]2([C@H]([C@H]3[C@@H]([C@@]4([C@H](NC(=O)C=C4)CC3)C)CC2)CC1)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
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Cite this record
CBID:1086 http://www.chembase.cn/molecule-1086.html
NAMES AND DATABASE IDS
NAMES AND DATABASE IDS
Names Database IDs
IUPAC name
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(1S,2R,7R,10S,11S,14S,15S)-N-tert-butyl-2,15-dimethyl-5-oxo-6-azatetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-3-ene-14-carboxamide
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(1S,2R,7R,10S,11S,14S,15S)-N-tert-butyl-2,15-dimethyl-5-oxo-6-azatetracyclo[8.7.0.02,7.011,15]heptadec-3-ene-14-carboxamide
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IUPAC Traditional name
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Brand Name
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Chibro-Proscar
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Finastid
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Finpecia
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Propecia
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Proscar
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Prostide
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Synonyms
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(5α,17β)-N-(1,1-Dimethylethyl)-3-oxo-4-azaandrost-1-ene-17-carboxamide
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Prostide
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Finastid
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Finasterida [INN-Spanish]
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Finasteridum [INN-Latin]
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Finasteride
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MK-906
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N-tert-Butyl-3-oxo-4-aza-5α-androst-1-en-17β-carboxamide
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N-(2-methyl-2-propyl)-3-oxo-4-aza-5α-androst-1-ene-17β-carboxamide
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Finasteride
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Proscar
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Propecia
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(4aR,4bS,6aS,7S,9aS,9bS,11aR)-N-tert-butyl-4a,6a-dimethyl-2-oxo-2,4a,4b,5,6,6a,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-indeno[5,4-f]quinoline-7-carboxamide
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N-叔丁基-3-氧代-4-氮杂-5α-雄甾-1-烯-17β-甲酰胺
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N-(2-甲基-2-丙基)-3-氧代-4-氮杂-5α-雄甾-1-烯-17β-甲酰胺
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非那甾胺
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CAS Number
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MDL Number
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PubChem SID
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PubChem CID
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DATA SOURCES
DATA SOURCES
All Sources Commercial Sources Non-commercial Sources
CALCULATED PROPERTIES
CALCULATED PROPERTIES
JChem
ALOGPS 2.1
Acid pKa
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14.525358
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H Acceptors
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2
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H Donor
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2
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LogD (pH = 5.5)
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3.0735092
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LogD (pH = 7.4)
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3.0735118
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Log P
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3.073512
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Molar Refractivity
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108.196 cm3
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Polarizability
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42.34966 Å3
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Polar Surface Area
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58.2 Å2
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Rotatable Bonds
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2
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Lipinski's Rule of Five
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true
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Log P
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3.53
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LOG S
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-5.27
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Solubility (Water)
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1.98e-03 g/l
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DETAILS
DETAILS
DrugBank
Selleck Chemicals
Sigma Aldrich
TRC
DrugBank -
DB01216
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Item |
Information |
Drug Groups
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approved |
Description
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An orally active testosterone 5-alpha-reductase inhibitor. It is used as a surgical alternative for treatment of benign prostatic hyperplasia. [PubChem] |
Indication |
For the treatment of symptomatic benign prostatic hyperplasia (BPH) in men with an enlarged prostate to: Improve symptoms, reduce the risk of acute urinary retention, reduce the risk of the need for surgery including transurethral resection of the prostate. Also used for the stimulation of regrowth of hair in men with mild to moderate androgenetic alopecia (male pattern alopecia, hereditary alopecia, common male baldness). |
Pharmacology |
Finasteride is a synthetic 4-azasteroid compound. This drug is a competitive and specific inhibitor of Type II 5a-reductase, an intracellular enzyme that converts the androgen testosterone into 5α-dihydrotestosterone (DHT). Two distinct isozymes are found in mice, rats, monkeys, and humans: Type I and II. Each of these isozymes is differentially expressed in tissues and developmental stages. In humans, 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. Although finasteride is 100-fold more selective for type II 5a-reductase than for the type I isoenzyme, chronic treatment with this drug may have some effect on type I 5a-reductase. |
Affected Organisms |
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Humans and other mammals |
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Biotransformation |
Drug is extensively metabolized, primarily in the liver via CYP3A4. Two metabolites have been identified with ≤20% of the activity of finasteride. |
Half Life |
4.5 hours (range 3.3-13.4 hours) |
Protein Binding |
Approximately 90% |
Elimination |
Following an oral dose of 14C-finasteride in man (n = 6), a mean of 39% (range, 32 to 46%) of the dose was excreted in the urine in the form of metabolites; 57% (range, 51 to 64%) was excreted in the feces. Urinary excretion of metabolites was decreased in patients with renal impairment. This decrease was associated with an increase in fecal excretion of metabolites. |
Distribution |
* 44 to 96 L |
Clearance |
* 165 mL/min [healthy young subjects] |
References |
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Suzuki R, Satoh H, Ohtani H, Hori S, Sawada Y: Saturable binding of finasteride to steroid 5alpha-reductase as determinant of nonlinear pharmacokinetics. Drug Metab Pharmacokinet. 2010;25(2):208-13.
[Pubmed]
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Smith AB, Carson CC: Finasteride in the treatment of patients with benign prostatic hyperplasia: a review. Ther Clin Risk Manag. 2009 Jun;5(3):535-45. Epub 2009 Jul 12.
[Pubmed]
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External Links |
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DrugBank -
DB07774
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Drug information: experimental |
Selleck Chemicals -
S1197
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Research Area: Prostate cancer Biological Activity: Finasteride, a synthetic 4-azasteroid antiandrogen compound, is a specific inhibitor of steroid Type II 5α-reductase, an intracellular enzyme that converts the androgen testosterone into 5α-dihydrotestosterone (DHT). [1]Finasteride is used in the treatment of prostate cancer, benign prostatic hyperplasia, and androgenetic alopecia (male pattern baldness). [1]In benign prostatic hyperplasia, finasteride inhibits 5alpha-reductase activity in epithelium for Ki of 10nM, significantly lower than in stroma (Ki = 33nM). [2]References on Finasteride[] J. Steroid Biochem. Molec. Biol., 1998, 67:49-55 |
Sigma Aldrich -
F1293
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Biochem/physiol Actions Selective 5α-reductase inhibitor; antiandrogen. Other Notes Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. F1293.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin. |
Sigma Aldrich -
34202
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Biochem/physiol Actions Selective 5α-reductase inhibitor; antiandrogen. Legal Information VETRANAL is a trademark of Sigma-Aldrich Co. LLC |
Toronto Research Chemicals -
F342000
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Inhibitor of 5α-reductase, the enzyme which converts testosterone to the more potent androgen, 5α-dihydrotestosterone.Antialopecia agent. |
REFERENCES
REFERENCES
From Suppliers
Google Scholar
PubMed
Google Books
- • Suzuki R, Satoh H, Ohtani H, Hori S, Sawada Y: Saturable binding of finasteride to steroid 5alpha-reductase as determinant of nonlinear pharmacokinetics. Drug Metab Pharmacokinet. 2010;25(2):208-13. Pubmed
- • Smith AB, Carson CC: Finasteride in the treatment of patients with benign prostatic hyperplasia: a review. Ther Clin Risk Manag. 2009 Jun;5(3):535-45. Epub 2009 Jul 12. Pubmed
- • http://en.wikipedia.org/wiki/Finasteride
- • 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)
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PATENTS
PATENTS
PubChem Patent
Google Patent