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

[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

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 8297		41.0 nM [IC50]
Steroid 5-alpha-reductase 2 3 Target ID: CHEMBL1856 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9873639	Inhibitor 8297		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 8429	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 8429	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 1737	substrate 1037	substrate 1217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
UGT1A1 204 UGT1A3 84 UGT1A4 77 UGT1A6 108 UGT1A9 116 UGT2B7 146 UGT2B15 64	CYP1A1 349 CYP2B6 664 CYP2C8 693 CYP2E1 667

Drug as perpetrator

Target	Modality	Activity
UGT1A1 254	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/25448279/	no
UGT1A3 93	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/25448279/	no
UGT1A6 141	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/25448279/	no
UGT1A9 121	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/25448279/	no
UGT2B15 64	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/25448279/	no
UGT2B7 157	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/25448279/	no
UGT1A4 80	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/25448279/	yes [IC50 11.5 uM]
P-gp 1650	activator 214 Sources: https://journals.eco-vector.com/pavlovj/article/view/4677	yes

Drug as victim

Target	Modality	Activity
CYP1A1 349	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/8654202/	no
CYP2B6 664	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/8654202/	no
CYP2C8 693	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/8654202/	no
CYP2C9 1037	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/8654202/	no
CYP2D6 1217	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/8654202/	no
CYP2E1 667	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/8654202/	no
CYP3A4 1737	substrate 3367 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
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
eMolecules	27520086	https://www.emolecules.com/cgi-bin/more?vid=27520086
eMolecules	538270	https://www.emolecules.com/cgi-bin/more?vid=538270

PubMed

Title	Date	PubMed
Anaemia in men receiving combined finasteride and flutamide therapy for advanced prostate cancer.	1999 Jan	10233450
Quality-of-life assessment in patients with benign prostatic hyperplasia: effects of various interventions.	2001	11735675
Hirsutism: diagnosis and management.	2001	11480095
Treatment of localized prostate cancer with intermittent triple androgen blockade: preliminary results in 110 consecutive patients.	2001	11306729
Changing therapeutic regimens in benign prostatic hyperplasia. Clinical and economic considerations.	2001	11284380
Treatments for androgenetic alopecia and alopecia areata: current options and future prospects.	2001	11217871
Evaluation of the male pubertal onset assay to detect testosterone and steroid biosynthesis inhibitors in CD rats.	2001 Apr	11248141
As genes differ, so should interventions for cancer.	2001 Apr 11	11308380
Effects of finasteride on size of the prostate gland and semen quality in dogs with benign prostatic hypertrophy.	2001 Apr 15	11330612
Effects of different steroid-biosynthesis inhibitors on the testicular steroidogenesis of the toad Bufo arenarum.	2001 Aug	11585264
Effect of androgen deprivation therapy on prostatic intraepithelial neoplasia.	2001 Aug	11502458
Androgen deprivation therapy for prostate cancer chemoprevention: current status and future directions for agent development.	2001 Aug	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 Aug	11502450
Neurosteroids mediate habituation and tonic inhibition in the auditory midbrain.	2001 Aug	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 Aug	11489700
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	11722704
Pharmacogenetics of human androgens and prostatic diseases.	2001 Feb	11258198
Management of lower urinary tract symptoms of elderly men in Austria.	2001 Feb	11223673
Effects of the anti-androgen finasteride on the modulatory actions of oestradiol on androgen metabolism by human gingival fibroblasts.	2001 Feb	11163318
Stable expression of the human 5alpha-reductase isoenzymes type I and type II in HEK293 cells to identify dual and selective inhibitors.	2001 Jan	11496834
Combined effect of terazosin and finasteride on apoptosis, cell proliferation, and transforming growth factor-beta expression in benign prostatic hyperplasia.	2001 Jan 1	11170131
Finasteride cream in hirsutism.	2001 Jan-Feb	11250761
Online prescriptions of pharmaceuticals: where is the evidence for harm or for benefit? A call for papers--and for reflection.	2001 Jan-Mar	11720943
Management of male pattern hair loss.	2001 Jul	11480145
Body dysmorphic disorder and life-style drugs. Overview and case report with finasteride.	2001 Jul	11471771
Androgen responsive genes as they affect hair growth.	2001 Jul-Aug	11399535
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 Jun	11434663
Finasteride and tamsulosin used in benign prostatic hypertrophy: a review of the prescription-event monitoring data.	2001 Jun	11412215
Steroid-sensitive gene-1 is an androgen-regulated gene expressed in prostatic smooth muscle cells in vivo.	2001 Jun	11357054
Enhanced anticonvulsant activity of neuroactive steroids in a rat model of catamenial epilepsy.	2001 Mar	11442150
Benign prostatic hyperplasia. Patient evaluation and relief of obstructive symptoms.	2001 Mar	11252759
[Gynecomastia and finasteride].	2001 May	11427816
Evaluating adverse cardiovascular effects of drug treatment for benign prostatic hyperplasia (BPH): methodological considerations.	2001 May	11337216
[Finasteride in prolonged therapy of patients with benign prostatic hyperplasia].	2001 May-Jun	11505535
Progesterone and 3alpha,5alpha-THP enhance sexual receptivity in mice.	2001 Oct	11584925
Direct-to-consumer advertising. Finasteride for male pattern hair loss.	2001 Sep	11570300
Molecular epidemiologic studies within the Selenium and Vitamin E Cancer Prevention Trial (SELECT).	2001 Sep	11552710
Anxiolytic effect of Kami-Shoyo-San (TJ-24) in mice: possible mediation of neurosteroid synthesis.	2001 Sep 21	11669460

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

Name

Type

Language

FINASTERIDE

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