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Finasteride (98319-26-7)

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Chemistry

IUPAC Name: (1S,3aS,3bS,5aR,9aR,9bS,11aS)-N-tert-Butyl-9a,11a-dimethyl-7-oxo-1,2,3,3a,3b,4,5,5a,6,9b,10,11-dodecahydroindeno[5,4-f]quinoline-1-carboxamide 
Following is the structure of Finasteride (CAS NO.98319-26-7):
                               
Empirical Formula: C23H36N2O2
Molecular Weight: 372.5441
Index of Refraction: 1.523
Molar Refractivity: 106.9 cm3
Molar Volume: 349.5 cm3
Density: 1.065 g/cm3
Flash Point: 177.4 °C
Melting point: 253 °C
Surface Tension: 37.7 dyne/cm
Water solubility: insoluble
Solubility: DMSO: 32 mg/mL, soluble
Enthalpy of Vaporization: 86.34 kJ/mol
Boiling Point: 576.6 °C at 760 mmHg
Vapour Pressure: 2.69E-13 mmHg at 25 °C 
Appearance of Finasteride (CAS NO.98319-26-7): Off-White Crystalline Powder
Product Categories of Finasteride (CAS NO.98319-26-7): Active Pharmaceutical Ingredients; API; Biochemistry; Steroids; Steroids (Others); Intermediates & Fine Chemicals; Pharmaceuticals; Vitamin Ingredients; Intracellular receptor
Canonical SMILES: CC12CCC3C(C1CCC2C(=O)NC(C)(C)C)CCC4C3(C=CC(=O)N4)C
Isomeric SMILES: C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2C(=O)NC(C)(C)C)CC[C@@H]4[C@@]3(C=CC(=O)N4)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

Uses

 Finasteride (CAS NO.98319-26-7) is used as a treatment in benign prostatic hyperplasia (BPH) in low doses, and prostate cancer in higher doses. A May, 2008 study indicates that finasteride reduces the rate of prostate cancer by 30%. It is also indicated for use in combination with doxazosin therapy to reduce the risk for symptomatic progression of BPH. Additionally, it is registered in many countries for androgenetic alopecia (male-pattern baldness).

Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LD50 oral > 1gm/kg (1000mg/kg) GASTROINTESTINAL: NAUSEA OR VOMITING Kiso to Rinsho. Clinical Report. Vol. 28, Pg. 4091, 1994.
mouse LD50 intraperitoneal 372mg/kg (372mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
BEHAVIORAL: ATAXIA
LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION
Kiso to Rinsho. Clinical Report. Vol. 28, Pg. 4091, 1994.
mouse LD50 oral 486mg/kg (486mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
BEHAVIORAL: ATAXIA
LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION
Kiso to Rinsho. Clinical Report. Vol. 28, Pg. 4091, 1994.
mouse LD50 subcutaneous > 2gm/kg (2000mg/kg)   Kiso to Rinsho. Clinical Report. Vol. 28, Pg. 4091, 1994.
rat LD50 intraperitoneal 885mg/kg (885mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
GASTROINTESTINAL: ULCERATION OR BLEEDING FROM SMALL INTESTINE
GASTROINTESTINAL: PERITONITIS
Kiso to Rinsho. Clinical Report. Vol. 28, Pg. 4091, 1994.
rat LD50 oral 418mg/kg (418mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
GASTROINTESTINAL: ULCERATION OR BLEEDING FROM STOMACH
LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION
Kiso to Rinsho. Clinical Report. Vol. 28, Pg. 4091, 1994.
rat LD50 subcutaneous > 2gm/kg (2000mg/kg) SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE" Kiso to Rinsho. Clinical Report. Vol. 28, Pg. 4091, 1994.

Safety Profile

Hazard Codes: HarmfulXn,ToxicT,IrritantXi
Risk Statements: 22-61-60-36/37/38 
R22:Harmful if swallowed. 
R61:May cause harm to the unborn child. 
R60:May impair fertility. 
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 36/37/39-45-53-36-26 
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection. 
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) 
S53:Avoid exposure - obtain special instructions before use. 
S36:Wear suitable protective clothing. 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
WGK Germany: 3
RTECS: CL5245000

Specification

 Finasteride , its cas register number 98319-26-7. It also can be called N-(2-methyl-2-propyl)-3-oxo-4-aza-5alpha-androst-1-ene-17beta-carboxamide ; Proscar ; N-tert-Butyl-3-oxo-4-aza-5alpha-androst-1-ene-17beta-carboxamide ; (5alpha,17beta)-(1,1-Dimethylethyl)-3-oxo-4-azaandrost-1-ene-17-carboxamide ; and 17beta-(N-tert-butylcarbamoyl)-4-aza-5 alpha-androst-1-en-3-one . Its classification code are Drug / Therapeutic Agent; Enzyme inhibitors; Inhibitor [alpha reductase] and Reproductive Effect.
 Finasteride (marketed as Proscar, Propecia, Fincar, Finpecia, Finax, Finast, Finara, Finalo, Prosteride, Gefina, Appecia, Finasterid IVAX, Finasterid Alternova) is a synthetic antiandrogen which acts by inhibiting type II 5-alpha reductase, the enzyme that converts testosterone to dihydrotestosterone (DHT).
 Finasteride was approved initially in 1992 as Proscar, a treatment for prostate enlargement, but the sponsor had studied 1 mg of finasteride and demonstrated hair growth in male pattern hair loss. In 1997, the U.S. Food and Drug Administration approved finasteride to treat male pattern hair loss. Merck sells it under the brand name Propecia.
Health organisations and practising clinicians have expressed concerns that Propecia gives rise to persistent side effects in some men.

Finasteride Basic information

  • Product Name:

    Finasteride

  • CAS No:98319-26-7
  • Formula:C23H36N2O2
  • Molecular Structure:Molecular Structure of (<span class=bigs><a href=/cas-983/98319-26-7.html />98319-26-7</a></span>) (Finasteride)
  • Synonyms:Proscar (TN);17beta-(N-tert-butylcarbamoyl)-4-aza-5 alpha-androst-1-en-3-one;Finasteride (USP);Finpecia;4-Azaandrost-1-ene-17-carboxamide, N-(1,1-dimethylethyl)-3-oxo-, (5alpha,17beta)-;Proscar;? Finasteride;L-652,931;MK 0906;(5alpha,17beta)-(1,1-Dimethylethyl)-3-oxo-4-azaandrost-1-ene-17-carboxamide;N-tert-butyl-3-oxo-4-aza-5alpha-androst-1-ene-17beta-carboxamide;Finastid;N-(2-Methyl-2-propyl)-3-oxo-4-aza-5-alpha-androst-1-ene-17-beta-carboxamide;Propecia (TN);Propecia;MK-0906;MK 906;1H-Indeno[5,4-f]quinoline-7-carboxamide,N- (1,1-dimethylethyl)-2,4a,4b,5,6,6a,7,8,9,9a,9b,- 10,11,11a-tetradecahydro-4a,6a-dimethyl-2- oxo-,(4aR,4bS,6aS,7S,9aS,9bS,11aR)-;Finasteride [USAN:BAN:INN];Florfenicol;MK-906;Prostide;Chibro-Proscar;Finasterida [INN-Spanish];Finasteridum [INN-Latin];(5alpha,17beta)-N-(1,1-Dimethylethyl)-3-oxo-4-azaandrost-1-ene-17-carboxamide;N-tert-butyl-4-aza-5alpha-androsta-3-oxo-17beta-carboxamide;Finasteride 99%;