U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C23H36N2O2
Molecular Weight 372.5441
Optical Activity UNSPECIFIED
Defined Stereocenters 7 / 7
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of FINASTERIDE

SMILES

[H][C@@]12CC[C@H](C(=O)NC(C)(C)C)[C@@]1(C)CC[C@@]3([H])[C@@]2([H])CC[C@@]4([H])NC(=O)C=C[C@]34C

InChI

InChIKey=DBEPLOCGEIEOCV-WSBQPABSSA-N
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

HIDE SMILES / InChI

Molecular Formula C23H36N2O2
Molecular Weight 372.5441
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 7 / 7
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: Description was created based on several sources, including http://onlinelibrary.wiley.com/doi/10.1111/j.1527-3458.2006.00053.x/pdf and https://www.drugs.com/pro/finasteride.html

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. Finasteride is used 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). Finasteride is sold under the brand names Proscar and Propecia among others.

CNS Activity

Curator's Comment: Finasteride has been found to cross the blood-brain barrier.

Originator

Curator's Comment: # Merck & Co

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
41.0 nM [IC50]
1.2 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
PROPECIA

Approved Use

PROPECIA is indicated for the treatment of male pattern hair loss (androgenetic alopecia) in MEN ONLY.

Launch Date

8.8084801E11
Primary
Proscar

Approved Use

PROSCAR is indicated 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 (TURP) and prostatectomy.

Launch Date

7.0882558E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
9.2 ng/mL
1 mg 1 times / day steady-state, oral
dose: 1 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
FINASTERIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
53 ng × h/mL
1 mg 1 times / day steady-state, oral
dose: 1 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
FINASTERIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
4.5 h
1 mg 1 times / day steady-state, oral
dose: 1 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
FINASTERIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
10%
1 mg 1 times / day steady-state, oral
dose: 1 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
FINASTERIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG



Drug as perpetrator​Drug as victim
PubMed

PubMed

TitleDatePubMed
Quality-of-life assessment in patients with benign prostatic hyperplasia: effects of various interventions.
2001
Dietary supplement use in the Prostate Cancer Prevention Trial: implications for prevention trials.
2001
The value of hair cosmetics and pharmaceuticals.
2001
Lower urinary tract symptoms suggestive of benign prostatic obstruction--Triumph: the role of general practice databases.
2001
Lower urinary tract symptoms suggestive of benign prostatic obstruction: how can clinical expertise contribute to rational management?
2001
Discontinuation of alpha-blockade after initial treatment with finasteride and doxazosin for bladder outlet obstruction.
2001
Androgen antagonists: Potential role in prostate cancer prevention.
2001 Apr
As genes differ, so should interventions for cancer.
2001 Apr 11
Effects of finasteride on size of the prostate gland and semen quality in dogs with benign prostatic hypertrophy.
2001 Apr 15
Narcissus drowned.
2001 Apr 28
Docetaxel followed by hormone therapy after failure of definitive treatments for clinically localized/locally advanced prostate cancer: preliminary results.
2001 Aug
Effect of androgen deprivation therapy on prostatic intraepithelial neoplasia.
2001 Aug
Ventral tegmental area infusions of inhibitors of the biosynthesis and metabolism of 3alpha,5alpha-THP attenuate lordosis of hormone-primed and behavioural oestrous rats and hamsters.
2001 Dec
Pharmacogenetics of human androgens and prostatic diseases.
2001 Feb
Bioequivalence study of finasteride. Determination in human plasma by high-pressure liquid chromatography coupled to tandem mass spectrometry.
2001 Feb
Management of lower urinary tract symptoms of elderly men in Austria.
2001 Feb
[Status of scalp hair and therapy of alopecia in men in Switzerland].
2001 Feb 15
Is there a place for combination medical therapy?
2001 Jan
Comparison of histological compositions and apoptosis in canine spontaneous benign prostatic hyperplasia treated with androgen suppressive agents chlormadinone acetate and finasteride.
2001 Jan
Combined effect of terazosin and finasteride on apoptosis, cell proliferation, and transforming growth factor-beta expression in benign prostatic hyperplasia.
2001 Jan 1
Online prescriptions of pharmaceuticals: where is the evidence for harm or for benefit? A call for papers--and for reflection.
2001 Jan-Mar
Management of male pattern hair loss.
2001 Jul
Body dysmorphic disorder and life-style drugs. Overview and case report with finasteride.
2001 Jul
The "Dorian Gray Syndrome": psychodynamic need for hair growth restorers and other "fountains of youth.".
2001 Jul
Steroid-sensitive gene-1 is an androgen-regulated gene expressed in prostatic smooth muscle cells in vivo.
2001 Jun
Enhanced anticonvulsant activity of neuroactive steroids in a rat model of catamenial epilepsy.
2001 Mar
Clinical application of 5alpha-reductase inhibitors.
2001 Mar
Characterization of the 5alpha-reductase-3alpha-hydroxysteroid dehydrogenase complex in the human brain.
2001 Mar
[Finasteride in prolonged therapy of patients with benign prostatic hyperplasia].
2001 May-Jun
Contribution of androgens to chronic allograft nephropathy is mediated by dihydrotestosterone.
2001 Nov
Baldness. Medical solutions for men and women.
2001 Nov
Managing benign prostatic hyperplasia.
2001 Oct
Increased expression of the neuropeptide Y receptor Y(1) gene in the medial amygdala of transgenic mice induced by long-term treatment with progesterone or allopregnanolone.
2001 Oct
Molecular epidemiologic studies within the Selenium and Vitamin E Cancer Prevention Trial (SELECT).
2001 Sep
Possible mechanisms of miniaturization during androgenetic alopecia or pattern hair loss.
2001 Sep
Patents

Sample Use Guides

In Vivo Use Guide
Usual Adult Dose for Benign Prostatic Hyperplasia 5 mg orally once a day Usual Adult Dose for Androgenetic Alopecia 1 mg orally once a day
Route of Administration: Oral
Finasteride (0.5 uM - 1 uM) down-regulated the expression of AR target genes in LNCaP cells
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:06:54 UTC 2023
Edited
by admin
on Fri Dec 15 15:06:54 UTC 2023
Record UNII
57GNO57U7G
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
FINASTERIDE
EP   HSDB   INN   JAN   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD  
INN   USAN  
Official Name English
FINASTERIDE [JAN]
Common Name English
NSC-759318
Code English
finasteride [INN]
Common Name English
ENTADFI COMPONENT FINASTERIDE
Brand Name English
N-tert-Butyl-3-oxo-4-aza-5α-androst-1-ene-17β-carboxamide
Common Name English
MK-906
Code English
FINASTERIDE [USAN]
Common Name English
FINASTERIDE COMPONENT OF ENTADFI
Brand Name English
FINASTERIDE [EP IMPURITY]
Common Name English
FINASTERIDE [EP MONOGRAPH]
Common Name English
FINASTERIDE [USP MONOGRAPH]
Common Name English
FINASTERIDE [USP IMPURITY]
Common Name English
Finasteride [WHO-DD]
Common Name English
FINASTERIDE [MART.]
Common Name English
PROSCAR
Brand Name English
4-AZAANDROST-1-ENE-17-CARBOXAMIDE, N-(1,1-DIMETHYLETHYL)-3-OXO-, (5.ALPHA.,17.BETA.)-
Systematic Name English
FINASTERIDE [MI]
Common Name English
PROPECIA
Brand Name English
FINASTERIDE [ORANGE BOOK]
Common Name English
NSC-741485
Code English
FINASTERIDE [VANDF]
Common Name English
Classification Tree Code System Code
WHO-VATC QG04CB01
Created by admin on Fri Dec 15 15:06:54 UTC 2023 , Edited by admin on Fri Dec 15 15:06:54 UTC 2023
EPA PESTICIDE CODE 129113
Created by admin on Fri Dec 15 15:06:54 UTC 2023 , Edited by admin on Fri Dec 15 15:06:54 UTC 2023
NCI_THESAURUS C2319
Created by admin on Fri Dec 15 15:06:54 UTC 2023 , Edited by admin on Fri Dec 15 15:06:54 UTC 2023
WHO-ATC G04CA51
Created by admin on Fri Dec 15 15:06:54 UTC 2023 , Edited by admin on Fri Dec 15 15:06:54 UTC 2023
WHO-ATC G04CB01
Created by admin on Fri Dec 15 15:06:54 UTC 2023 , Edited by admin on Fri Dec 15 15:06:54 UTC 2023
WHO-VATC QD11AX10
Created by admin on Fri Dec 15 15:06:54 UTC 2023 , Edited by admin on Fri Dec 15 15:06:54 UTC 2023
NDF-RT N0000000126
Created by admin on Fri Dec 15 15:06:54 UTC 2023 , Edited by admin on Fri Dec 15 15:06:54 UTC 2023
LIVERTOX NBK548319
Created by admin on Fri Dec 15 15:06:54 UTC 2023 , Edited by admin on Fri Dec 15 15:06:54 UTC 2023
WHO-ATC D11AX10
Created by admin on Fri Dec 15 15:06:54 UTC 2023 , Edited by admin on Fri Dec 15 15:06:54 UTC 2023
WHO-VATC QG04CA51
Created by admin on Fri Dec 15 15:06:54 UTC 2023 , Edited by admin on Fri Dec 15 15:06:54 UTC 2023
NDF-RT N0000175836
Created by admin on Fri Dec 15 15:06:54 UTC 2023 , Edited by admin on Fri Dec 15 15:06:54 UTC 2023
Code System Code Type Description
FDA UNII
57GNO57U7G
Created by admin on Fri Dec 15 15:06:54 UTC 2023 , Edited by admin on Fri Dec 15 15:06:54 UTC 2023
PRIMARY
IUPHAR
6818
Created by admin on Fri Dec 15 15:06:54 UTC 2023 , Edited by admin on Fri Dec 15 15:06:54 UTC 2023
PRIMARY
ChEMBL
CHEMBL710
Created by admin on Fri Dec 15 15:06:54 UTC 2023 , Edited by admin on Fri Dec 15 15:06:54 UTC 2023
PRIMARY
PUBCHEM
57363
Created by admin on Fri Dec 15 15:06:54 UTC 2023 , Edited by admin on Fri Dec 15 15:06:54 UTC 2023
PRIMARY
DRUG BANK
DB01216
Created by admin on Fri Dec 15 15:06:54 UTC 2023 , Edited by admin on Fri Dec 15 15:06:54 UTC 2023
PRIMARY
NSC
759318
Created by admin on Fri Dec 15 15:06:54 UTC 2023 , Edited by admin on Fri Dec 15 15:06:54 UTC 2023
PRIMARY
SMS_ID
100000092656
Created by admin on Fri Dec 15 15:06:54 UTC 2023 , Edited by admin on Fri Dec 15 15:06:54 UTC 2023
PRIMARY
NCI_THESAURUS
C1099
Created by admin on Fri Dec 15 15:06:54 UTC 2023 , Edited by admin on Fri Dec 15 15:06:54 UTC 2023
PRIMARY
WIKIPEDIA
FINASTERIDE
Created by admin on Fri Dec 15 15:06:54 UTC 2023 , Edited by admin on Fri Dec 15 15:06:54 UTC 2023
PRIMARY
NSC
741485
Created by admin on Fri Dec 15 15:06:54 UTC 2023 , Edited by admin on Fri Dec 15 15:06:54 UTC 2023
PRIMARY
RXCUI
25025
Created by admin on Fri Dec 15 15:06:54 UTC 2023 , Edited by admin on Fri Dec 15 15:06:54 UTC 2023
PRIMARY RxNorm
DAILYMED
57GNO57U7G
Created by admin on Fri Dec 15 15:06:54 UTC 2023 , Edited by admin on Fri Dec 15 15:06:54 UTC 2023
PRIMARY
EPA CompTox
DTXSID3020625
Created by admin on Fri Dec 15 15:06:54 UTC 2023 , Edited by admin on Fri Dec 15 15:06:54 UTC 2023
PRIMARY
MESH
D018120
Created by admin on Fri Dec 15 15:06:54 UTC 2023 , Edited by admin on Fri Dec 15 15:06:54 UTC 2023
PRIMARY
RS_ITEM_NUM
1270402
Created by admin on Fri Dec 15 15:06:54 UTC 2023 , Edited by admin on Fri Dec 15 15:06:54 UTC 2023
PRIMARY
CAS
98319-26-7
Created by admin on Fri Dec 15 15:06:54 UTC 2023 , Edited by admin on Fri Dec 15 15:06:54 UTC 2023
PRIMARY
MERCK INDEX
m5383
Created by admin on Fri Dec 15 15:06:54 UTC 2023 , Edited by admin on Fri Dec 15 15:06:54 UTC 2023
PRIMARY Merck Index
CHEBI
5062
Created by admin on Fri Dec 15 15:06:54 UTC 2023 , Edited by admin on Fri Dec 15 15:06:54 UTC 2023
PRIMARY
HSDB
6793
Created by admin on Fri Dec 15 15:06:54 UTC 2023 , Edited by admin on Fri Dec 15 15:06:54 UTC 2023
PRIMARY
DRUG CENTRAL
1171
Created by admin on Fri Dec 15 15:06:54 UTC 2023 , Edited by admin on Fri Dec 15 15:06:54 UTC 2023
PRIMARY
INN
6539
Created by admin on Fri Dec 15 15:06:54 UTC 2023 , Edited by admin on Fri Dec 15 15:06:54 UTC 2023
PRIMARY
USAN
AA-52
Created by admin on Fri Dec 15 15:06:54 UTC 2023 , Edited by admin on Fri Dec 15 15:06:54 UTC 2023
PRIMARY
EVMPD
SUB07629MIG
Created by admin on Fri Dec 15 15:06:54 UTC 2023 , Edited by admin on Fri Dec 15 15:06:54 UTC 2023
PRIMARY
Related Record Type Details
TARGET->WEAK INHIBITOR
IC50
TARGET -> INHIBITOR
A Slow-Binding 5a-Reductase Inhibitor
TIME-DEPENDENT INHIBITION
IC50
Related Record Type Details
METABOLITE -> PARENT
IN DOGS
FECAL; PLASMA; URINE
METABOLITE LESS ACTIVE -> PARENT
via the cytochrome P450 3A4 enzyme subfamily
MAJOR
URINE
METABOLITE LESS ACTIVE -> PARENT
via the cytochrome P450 3A4 enzyme subfamily
MAJOR
PLASMA
Related Record Type Details
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Related Record Type Details
ACTIVE MOIETY