DUTASTERIDE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C27H30F6N2O2
Molecular Weight	528.5297
Optical Activity	UNSPECIFIED
Defined Stereocenters	7 / 7
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C[C@]12CC[C@H]3[C@@H](CC[C@H]4NC(=O)C=C[C@]34C)[C@@H]1CC[C@@H]2C(=O)NC5=CC(=CC=C5C(F)(F)F)C(F)(F)F

InChI

InChIKey=JWJOTENAMICLJG-QWBYCMEYSA-N

InChI=1S/C27H30F6N2O2/c1-24-11-9-17-15(4-8-21-25(17,2)12-10-22(36)35-21)16(24)6-7-19(24)23(37)34-20-13-14(26(28,29)30)3-5-18(20)27(31,32)33/h3,5,10,12-13,15-17,19,21H,4,6-9,11H2,1-2H3,(H,34,37)(H,35,36)/t15-,16-,17-,19+,21+,24-,25+/m0/s1

HIDE SMILES / InChI

Molecular Formula	C27H30F6N2O2
Molecular Weight	528.5297
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/DB01126
Curator's Comment: Description was created based on several sources, including http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/021319s028s029lbl.pdf

Dutasteride is a synthetic 4-azasteroid compound that is a selective inhibitor of both the type 1 and type 2 isoforms of steroid 5 alpha-reductase (5AR), intracellular enzymes that convert testosterone to 5 alpha-dihydrotestosterone (DHT). 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. Dutasteride inhibits the conversion of testosterone to 5 alpha-dihydrotestosterone (DHT), which is the androgen primarily responsible for the initial development and subsequent enlargement of the prostate gland. Testosterone is converted to DHT by the enzyme 5 alpha-reductase, which exists as 2 isoforms, type 1 and type 2. Dutasteride is a competitive and specific inhibitor of both type 1 and type 2 5 alpha-reductase isoenzymes, with which it forms a stable enzyme complex. Dissociation from this complex has been evaluated under in vitro and in vivo conditions and is extremely slow. Used for the treatment of symptomatic benign prostatic hyperplasia (BPH) in men with an enlarged prostate gland to improve symptoms, and reduce the risk of acute urinary retention and the need for surgery. Marketed under the brand name Avodart.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Glycine receptor subunit alpha-1 24 Target ID: CHEMBL5845 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25790278	Modulator 846		0.33 µM [EC50]
Steroid 5-alpha-reductase 15 Target ID: CHEMBL2363075 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20519274	Inhibitor 8504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Benign prostatic hyperplasia 28 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/021319s028s029lbl.pdf	Primary		Approved 8583	AVODART Approved Use AVODART 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, and reduce the risk of the need for BPH-related surgery. AVODART in combination with the alpha adrenergic antagonist, tamsulosin, is indicated for the treatment of symptomatic BPH in men with an enlarged prostate Launch Date 2001

C_max

Value	Dose	Co-administered	Analyte	Population
8.91 ng/mL EXPERIMENT https://link.springer.com/article/10.1365/s10337-008-0613-7	0.5 mg single, oral dose: 0.5 mg route of administration: Oral experiment type: SINGLE co-administered: TAMSULOSIN	TAMSULOSIN	DUTASTERIDE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
56.85 ng × h/mL EXPERIMENT https://link.springer.com/article/10.1365/s10337-008-0613-7	0.5 mg single, oral dose: 0.5 mg route of administration: Oral experiment type: SINGLE co-administered: TAMSULOSIN	TAMSULOSIN	DUTASTERIDE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
5.71 h EXPERIMENT https://link.springer.com/article/10.1365/s10337-008-0613-7	0.5 mg single, oral dose: 0.5 mg route of administration: Oral experiment type: SINGLE co-administered: TAMSULOSIN	TAMSULOSIN	DUTASTERIDE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
35 day REVIEW https://www.ncbi.nlm.nih.gov/pubmed/14565784	0.5 mg 1 times / day steady-state, oral dose: 0.5 mg route of administration: Oral experiment type: STEADY-STATE co-administered:		DUTASTERIDE plasma	Homo sapiens population: UNKNOWN age: ADULT sex: FEMALE / MALE food status: UNKNOWN

F_unbound

Value	Dose	Co-administered	Analyte	Population
0.5% REVIEW https://www.ncbi.nlm.nih.gov/pubmed/14565784	0.5 mg 1 times / day steady-state, oral dose: 0.5 mg route of administration: Oral experiment type: STEADY-STATE co-administered:		DUTASTERIDE plasma	Homo sapiens population: UNKNOWN age: ADULT sex: FEMALE / MALE food status: UNKNOWN

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1946 inhibitor 2252 inducer 1087	substrate 1193 inhibitor 2438	substrate 1388 inhibitor 2507

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 2153 CYP2A6 879 CYP2E1 1060 CYP2C8 1057 CYP2C19 2057 CYP2B6 926 OAT3 747 OATP1B1 1079 OATP1B3 961 MRP2 499	CYP3A5 446 CYP1A2 1197 CYP2A6 626 CYP2C19 1119 CYP2E1 729

Drug as perpetrator

Target	Modality	Activity	Clinical evidence
CYP1A2 2333	inhibitor 4027 Sources: https://ca.gsk.com/media/588688/avodart.pdf#page=13 Page: 13.0	no
CYP2A6 911	inhibitor 4027 Sources: https://ca.gsk.com/media/588688/avodart.pdf#page=13 Page: 13.0	no
CYP2B6 1160	inhibitor 4027 Sources: https://ca.gsk.com/media/588688/avodart.pdf#page=13 Page: 13.0	no
CYP2C8 1117	inhibitor 4027 Sources: https://ca.gsk.com/media/588688/avodart.pdf#page=13 Page: 13.0	no
CYP2C9 2497	inhibitor 4027 Sources: https://ca.gsk.com/media/588688/avodart.pdf#page=13 Page: 13.0	no
CYP2D6 2546	inhibitor 4027 Sources: https://ca.gsk.com/media/588688/avodart.pdf#page=13 Page: 13.0	no
CYP2E1 1146	inhibitor 4027 Sources: https://ca.gsk.com/media/588688/avodart.pdf#page=13 Page: 13.0	no
CYP3A4 2633	inducer 1966 Sources: https://www.pmda.go.jp/files/000220574.pdf#page=9 Page: 9.0	no
MRP2 625	inhibitor 4027 Sources: https://www.pmda.go.jp/files/000220574.pdf#page=9 Page: 9.0	no
OAT3 749	inhibitor 4027 Sources: https://www.pmda.go.jp/files/000220574.pdf#page=9 Page: 9.0	yes [IC50 0.5 uM]	likely (co-administration study) Comment: Adverse events were experienced by subjects; however, none of these events was serious or causally related to dutasteride. Sources: https://www.pmda.go.jp/files/000220574.pdf#page=9 Page: 9.0
OATP1B1 1095	inhibitor 4027 Sources: https://www.pmda.go.jp/files/000220574.pdf#page=9 Page: 9.0	yes [IC50 0.8 uM]	likely (co-administration study) Comment: Adverse events were experienced by subjects; however, none of these events was serious or causally related to dutasteride. Sources: https://www.pmda.go.jp/files/000220574.pdf#page=9 Page: 9.0
OATP1B3 970	inhibitor 4027 Sources: https://www.pmda.go.jp/files/000220574.pdf#page=9 Page: 9.0	yes [IC50 20 uM]	likely (co-administration study) Comment: Adverse events were experienced by subjects; however, none of these events was serious or causally related to dutasteride. Sources: https://www.pmda.go.jp/files/000220574.pdf#page=9 Page: 9.0
CYP3A4 2633	inhibitor 4027 Sources: https://www.pmda.go.jp/files/000220574.pdf#page=8 Page: 8.0	yes [IC50 50 uM]
CYP2C19 2141	inhibitor 4027 Sources: https://www.pmda.go.jp/files/000220574.pdf#page=8 Page: 8.0	yes [IC50 50 uM]	likely (co-administration study) Comment: Adverse events were experienced by subjects; however, none of these events was serious or causally related to dutasteride. Sources: https://www.pmda.go.jp/files/000220574.pdf#page=8 Page: 8.0

Drug as victim

Target	Modality	Activity
CYP1A2 1197	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21319_Duagen_biopharmr_P1.pdf#page=7 Page: 7.0	no
CYP2A6 626	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21319_Duagen_biopharmr_P1.pdf#page=7 Page: 7.0	no
CYP2C19 1119	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21319_Duagen_biopharmr_P1.pdf#page=7 Page: 7.0	no
CYP2C9 1193	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21319_Duagen_biopharmr_P1.pdf#page=7 Page: 7.0	no
CYP2D6 1388	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21319_Duagen_biopharmr_P1.pdf#page=7 Page: 7.0	no
CYP2E1 729	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21319_Duagen_biopharmr_P1.pdf#page=7 Page: 7.0	no
CYP3A4 1946	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21319_Duagen_biopharmr_P1.pdf#page=7 Page: 7.0	yes
CYP3A5 446	substrate 4014 Sources: https://ca.gsk.com/media/588688/avodart.pdf#page=13 Page: 13.0	yes

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:521033	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:521033
ChemicalBook	CB3254628	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB3254628
eMolecules	8724782	https://www.emolecules.com/cgi-bin/more?vid=8724782
MolPort	MolPort-003-847-041	https://www.molport.com/shop/molecule-link/MolPort-003-847-041
Selleck Chemicals	Dutasteride	http://www.selleckchem.com/products/Dutasteride.html
ZINC	ZINC000003932831	http://zinc15.docking.org/substances/ZINC000003932831

PubMed

Title	Date	PubMed
Effects of the dual 5 alpha-reductase inhibitor dutasteride on apoptosis in primary cultures of prostate cancer epithelial cells and cell lines.	2006-06-15	16703599
Actions of 5alpha-reductase inhibitors on the epididymis.	2006-05-16	16476520
Gateways to clinical trials.	2006-05	16801985
Clinical usefulness of serum prostate specific antigen for the detection of prostate cancer is preserved in men receiving the dual 5alpha-reductase inhibitor dutasteride.	2006-05	16600723
Treatment and pharmacologic management of BPH in the context of common comorbidities.	2006-04	16613527
BPH: epidemiology and comorbidities.	2006-04	16613526
Dutasteride: a dual 5-alpha reductase inhibitor for the treatment of symptomatic benign prostatic hyperplasia.	2006-04	16569804
Combination of phosphodiesterase-5 inhibitors and alpha-blockers in patients with benign prostatic hyperplasia: treatments of lower urinary tract symptoms, erectile dysfunction, or both?	2006-04	16507053
Impact of medical treatments for benign prostatic hyperplasia on sexual function.	2006-04	16507052
Relationship among serum testosterone, sexual function, and response to treatment in men receiving dutasteride for benign prostatic hyperplasia.	2006-04	16434455
Gateways to clinical trials.	2006-03-17	16541195
Update on prostate cancer chemoprevention.	2006-03	16503715
Dutasteride, cantharidin, atopiclair, cetuximab, sirolimus, AC-11 and dimericine reviewed in brief.	2006-02	16485893
Oral testosterone in oil: pharmacokinetic effects of 5alpha reduction by finasteride or dutasteride and food intake in men.	2006-01-10	16400081
Treatment of lower urinary tract symptoms in benign prostatic hyperplasia and its impact on sexual function.	2006-01	16490576
By the way, doctor. I developed acute urinary retention after having a pacemaker put in. I'm a 90-year-old man and in pretty good shape considering my age, but I'd rather not have any more procedures. What are my options?	2006-01	16450452
Development of nomogram to predict acute urinary retention or surgical intervention, with or without dutasteride therapy, in men with benign prostatic hyperplasia.	2006-01	16413338
Long-term therapy with the dual 5alpha-reductase inhibitor dutasteride is well tolerated in men with symptomatic benign prostatic hyperplasia.	2006-01	16336332
Discovery and clinical development of dutasteride, a potent dual 5alpha-reductase inhibitor.	2006	16719800
Inhibitors of 5alpha-reductase in the treatment of benign prostatic hyperplasia.	2006	16515494
[Effect of dutasteride on reduction of plasma DHT following finasteride therapy in patients with benign prostatic hyperplasia].	2005-12	16429658
[Effect of dutasteride on reduction of intraoperative bleeding related to transurethral resection of the prostate].	2005-12	16429657
Gateways to clinical trials.	2005-12	16395422
Phase III prostate cancer prevention trials: are the costs justified?	2005-11-10	16278467
Effect of dutasteride on the detection of prostate cancer in men with benign prostatic hyperplasia.	2005-11	16217336
Evaluation and medical management of benign prostatic hyperplasia.	2005-10	16212149
Effect of dutasteride therapy on Doppler US evaluation of prostate: preliminary results.	2005-10	16183933
Effects of testosterone and levonorgestrel combined with a 5alpha-reductase inhibitor or gonadotropin-releasing hormone antagonist on spermatogenesis and intratesticular steroid levels in normal men.	2005-10	16030154
Gateways to clinical trials.	2005-09-24	16179960
Effective treatment of female androgenic alopecia with dutasteride.	2005-09-20	16167423
[Prevention of prostate cancer].	2005-09-09	16143928
Gateways to clinical trials.	2005-09	16258596
[Novel therapeutics strategies in benign hypertrophy of prostate management].	2005-09	16240894
Long-term sustained improvement in symptoms of benign prostatic hyperplasia with the dual 5alpha-reductase inhibitor dutasteride: results of 4-year studies.	2005-09	16104912
Selecting therapy for maintaining sexual function in patients with benign prostatic hyperplasia.	2005-08	16042709
Combined inhibition of types I and II 5 alpha-reductase selectively augments the basal (nonpulsatile) mode of testosterone secretion in young men.	2005-07	15811930
[Dutasteride (Avodart): a novel 5-alpha reductase inhibitor for treatment of benign prostate hypertrophy].	2005-06-11	15945422
Gateways to clinical trials.	2005-06	16082422
Pharmacogenetic analysis of human steroid 5 alpha reductase type II: comparison of finasteride and dutasteride.	2005-06	15956333
Sexual dysfunction and lower urinary tract symptoms (LUTS) associated with benign prostatic hyperplasia (BPH).	2005-06	15925080
Gateways to clinical trials.	2005-05	16082427
Oral testosterone in oil plus dutasteride in men: a pharmacokinetic study.	2005-05	15713724
Gateways to clinical trials.	2005-04	15834452
Chemoprevention of prostate cancer.	2005-04	15780904
RE: Effect of the dual 5alpha-reductase inhibitor dutasteride on markers of tumor regression in prostate cancer.	2005-04	15758829
Dutasteride: a novel dual inhibitor of 5alpha-reductase for benign prostatic hyperplasia.	2005-02	15757426
The dual 5-alpha-reductase inhibitor dutasteride induces atrophic changes and decreases relative cancer volume in human prostate.	2005-01	15667867
[Prostate carcinoma: can 5-alpha reductase inhibitors prevent it?].	2005	16515298
Noninvasive management of lower urinary tract symptoms and sexual dysfunction associated with benign prostatic hyperplasia in the primary care setting.	2005	16110128
Preventing diseases of the prostate in the elderly using hormones and nutriceuticals.	2004-06	15672940

Patents

Sample Use Guides

In Vivo Use Guide

Monotherapy: 0.5 mg once daily. Combination with tamsulosin: 0.5 mg once daily and tamsulosin 0.4 mg once daily. Dosing considerations: Swallow whole. May take with or without food.

Route of Administration: Oral

In Vitro Use Guide

Both low (0.25 uM) or high (1.0 uM) doses of dutasteride abrogated testosterone-stimulated growth of androgen-sensitive benign BPH-1 cells, LNCaP cancer cells, their derivative C4-2 cells, or Dunning rat cancer cells lines.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:03:48 GMT 2025` Edited by `admin` on `Mon Mar 31 18:03:48 GMT 2025`
Record UNII	O0J6XJN02I
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

AVODART

Preferred Name

English

DUTASTERIDE

Official Name

English

GI 198745

Code

English

AVOLVE

Common Name

English

DUASTRIDE

Brand Name

English

Dutasteride [WHO-DD]

Common Name

English

(5.ALPHA.,17.BETA.)-N-(2,5-BIS(TRIFLUOROMETHYL)PHENYL)-3-OXO-4-AZAANDROST-1-ENE-17-CARBOXAMIDE

Common Name

English

GG-745

Code

English

.ALPHA.,.ALPHA.,.ALPHA.,.ALPHA.',.ALPHA.',.ALPHA.'-HEXAFLUORO-3-OXO-4-AZA-5.ALPHA.-ANDROST-1-ENE-17.BETA.-CARBOXY-2',5'-XYLIDIDE

Common Name

English

JALYN COMPONENT DUTASTERIDE

Brand Name

English

DUTASTERIDE [USAN]

Common Name

English

dutasteride [INN]

Common Name

English

DUTASTERIDE [MI]

Common Name

English

DUTASTERIDE [VANDF]

Common Name

English

DUTASTERIDE [USP MONOGRAPH]

Common Name

English

DUTASTERIDE [USP-RS]

Common Name

English

DUTASTERIDE [ORANGE BOOK]

Common Name

English

NSC-740477

Code

English

DUTASTERIDE [MART.]

Common Name

English

DUTASTERIDE [EP MONOGRAPH]

Common Name

English

NSC-759880

Code

English

DUTASTERIDE [JAN]

Common Name

English

GI-198745

Code

English

Classification Tree Code System Code

LIVERTOX

NBK548058