FINASTERIDE

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 Search

SMILES

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

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
Sources: http://www.drugbank.ca/drugs/DB01216
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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Steroid 5-alpha-reductase 1 5 Target ID: CHEMBL1787 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12139451	Inhibitor 8504		41.0 nM [IC50]
Steroid 5-alpha-reductase 2 3 Target ID: CHEMBL1856 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9873639	Inhibitor 8504		1.2 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Androgenic alopecia 8 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/020788s018lbl.pdf	Primary		Approved 8583	PROPECIA Approved Use PROPECIA is indicated for the treatment of male pattern hair loss (androgenetic alopecia) in MEN ONLY. Launch Date 1997
Benign prostatic hyperplasia 28 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2010/020180s037lbl.pdf	Primary		Approved 8583	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 1992

C_max

Value	Dose	Co-administered	Analyte	Population
9.2 ng/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/020788s020s021s023lbl.pdf	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

Value	Dose	Co-administered	Analyte	Population
53 ng × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/020788s020s021s023lbl.pdf	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

T_1/2

Value	Dose	Co-administered	Analyte	Population
4.5 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/020788s020s021s023lbl.pdf	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

F_unbound

Value	Dose	Co-administered	Analyte	Population
10% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/020788s020s021s023lbl.pdf	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

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1946	substrate 1193	substrate 1388

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
UGT1A1 246 UGT1A3 89 UGT1A4 98 UGT1A6 136 UGT1A9 148 UGT2B7 197 UGT2B15 84	CYP1A1 389 CYP2B6 776 CYP2C8 810 CYP2E1 729

Drug as perpetrator

Target	Modality	Activity
UGT1A1 303	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/25448279/	no
UGT1A3 99	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/25448279/	no
UGT1A6 171	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/25448279/	no
UGT1A9 155	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/25448279/	no
UGT2B15 84	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/25448279/	no
UGT2B7 210	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/25448279/	no
UGT1A4 100	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/25448279/	yes [IC50 11.5 uM]
P-gp 1932	activator 342 Sources: https://journals.eco-vector.com/pavlovj/article/view/4677	yes

Drug as victim

Target	Modality	Activity
CYP1A1 389	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/8654202/	no
CYP2B6 776	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/8654202/	no
CYP2C8 810	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/8654202/	no
CYP2C9 1193	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/8654202/	no
CYP2D6 1388	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/8654202/	no
CYP2E1 729	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/8654202/	no
CYP3A4 1946	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/8654202/	yes

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:5062	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:5062
ChemicalBook	CB9433852	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB9433852
eMolecules	27520086	https://www.emolecules.com/cgi-bin/more?vid=27520086
eMolecules	538270	https://www.emolecules.com/cgi-bin/more?vid=538270
MolPort	MolPort-002-500-272	https://www.molport.com/shop/molecule-link/MolPort-002-500-272
Selleck Chemicals	Finasteride	http://www.selleckchem.com/products/Finasteride.html
ZINC	ZINC000003782599	http://zinc15.docking.org/substances/ZINC000003782599

PubMed

Title	Date	PubMed
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.	2001-12	11722704
Online prescriptions of pharmaceuticals: where is the evidence for harm or for benefit? A call for papers--and for reflection.	2001-11-27	11720943
Contribution of androgens to chronic allograft nephropathy is mediated by dihydrotestosterone.	2001-11	11703615
Baldness. Medical solutions for men and women.	2001-11	11692629
Pharmacokinetic parameters and mechanisms of inhibition of rat type 1 and 2 steroid 5alpha-reductases: determinants for different in vivo activities of GI198745 and finasteride in the rat.	2001-10-01	11543729
Managing benign prostatic hyperplasia.	2001-10	11677898
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.	2001-10	11677270
Replacement of surgical castration by GnRH-inhibition or Leydig cell ablation in the male rat Hershberger antiandrogen assay.	2001-10	11603962
Progesterone and 3alpha,5alpha-THP enhance sexual receptivity in mice.	2001-10	11584925
Co-administration of finasteride and the pure anti-oestrogen ICI 182,780 act synergistically in modulating the IGF system in rat prostate.	2001-10	11572795
Anxiolytic effect of Kami-Shoyo-San (TJ-24) in mice: possible mediation of neurosteroid synthesis.	2001-09-21	11669460
Direct-to-consumer advertising. Finasteride for male pattern hair loss.	2001-09	11570300
New progesterone esters as 5alpha-reductase inhibitors.	2001-09	11558590
Molecular epidemiologic studies within the Selenium and Vitamin E Cancer Prevention Trial (SELECT).	2001-09	11552710
Possible mechanisms of miniaturization during androgenetic alopecia or pattern hair loss.	2001-09	11511857
[Finasteride in prolonged therapy of patients with benign prostatic hyperplasia].	2001-08-17	11505535
Docetaxel followed by hormone therapy after failure of definitive treatments for clinically localized/locally advanced prostate cancer: preliminary results.	2001-08	11685725
Effects of different steroid-biosynthesis inhibitors on the testicular steroidogenesis of the toad Bufo arenarum.	2001-08	11585264
The impact of participation in a study of medical treatment of lower urinary tract symptoms on the incidence of prostate surgery.	2001-08	11550784
Effect of androgen deprivation therapy on prostatic intraepithelial neoplasia.	2001-08	11502458
Androgen deprivation therapy for prostate cancer chemoprevention: current status and future directions for agent development.	2001-08	11502457
Androgen deprivation therapy for patients with clinically localized (stages T1 to T3) prostate cancer and for patients with biochemical recurrence after radical prostatectomy.	2001-08	11502450
Neurosteroids mediate habituation and tonic inhibition in the auditory midbrain.	2001-08	11495974
Discontinuation of alpha-blockade after initial treatment with finasteride and doxazosin in men with lower urinary tract symptoms and clinical evidence of benign prostatic hyperplasia.	2001-08	11489700
[Prostate problems. More clarity regarding prognosis].	2001-07-26	11524988
Management of male pattern hair loss.	2001-07	11480145
Body dysmorphic disorder and life-style drugs. Overview and case report with finasteride.	2001-07	11471771
The "Dorian Gray Syndrome": psychodynamic need for hair growth restorers and other "fountains of youth.".	2001-07	11471770
A double-blind, randomized, placebo-controlled pilot study to investigate the effects of finasteride combined with a biodegradable self-reinforced poly L-lactic acid spiral stent in patients with urinary retention caused by bladder outlet obstruction from benign prostatic hyperplasia.	2001-07	11446841
[Wellbeing or happiness medications?].	2001-06-30	11440653
Effect of finasteride on behavioural arousal and somatosensory evoked potentials in fetal sheep.	2001-06-22	11403946
TrichoScan: combining epiluminescence microscopy with digital image analysis for the measurement of hair growth in vivo.	2001-06-16	11399546
Advances in the treatment of male androgenetic alopecia: a brief review of finasteride studies.	2001-06-16	11399540
Androgen responsive genes as they affect hair growth.	2001-06-12	11399535
Steroidogenic enzymes in skin.	2001-06-12	11399532
Prevention of prostate cancer.	2001-06	11525290
Inhibition of 5alpha-reductase enzyme or GABA(A) receptors in the VMH and the VTA attenuates progesterone-induced sexual behavior in rats and hamsters.	2001-06	11434663
Finasteride and tamsulosin used in benign prostatic hypertrophy: a review of the prescription-event monitoring data.	2001-06	11412215
[Gynecomastia and finasteride].	2001-05	11427816
Enhanced anticonvulsant activity of neuroactive steroids in a rat model of catamenial epilepsy.	2001-03	11442150
Neurosteroid withdrawal model of perimenstrual catamenial epilepsy.	2001-03	11442149
Stable expression of the human 5alpha-reductase isoenzymes type I and type II in HEK293 cells to identify dual and selective inhibitors.	2001-01	11496834
Quality-of-life assessment in patients with benign prostatic hyperplasia: effects of various interventions.	2001	11735675
Management of patients with LUTS suggestive of BPH.	2001	11598346
Dietary supplement use in the Prostate Cancer Prevention Trial: implications for prevention trials.	2001	11588893
Efficacy and tolerability of drugs for treatment of benign prostatic hyperplasia.	2001	11583366
Hirsutism: diagnosis and management.	2001	11480095
Finasteride: a long-term follow-up in the treatment of recurrent hematuria associated with benign prostatic hyperplasia.	2001	11464120
The value of hair cosmetics and pharmaceuticals.	2001	11455137
Inhibition of 5alpha-reductase in rat prostate reveals differential regulation of androgen-response gene expression by testosterone and dihydrotestosterone.	2001	11444528

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

In Vitro Use Guide

Finasteride (0.5 uM - 1 uM) down-regulated the expression of AR target genes in LNCaP cells

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:46:56 GMT 2025` Edited by `admin` on `Mon Mar 31 17:46:56 GMT 2025`
Record UNII	57GNO57U7G
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ENTADFI COMPONENT FINASTERIDE

Preferred Name

English

FINASTERIDE

Official Name

English

FINASTERIDE [JAN]

Common Name

English

NSC-759318

Code

English

finasteride [INN]

Common Name

English

N-tert-Butyl-3-oxo-4-aza-5?-androst-1-ene-17?-carboxamide

Common Name

English

MK-906

Code

English

FINASTERIDE [USAN]

Common 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