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Details

Stereochemistry ABSOLUTE
Molecular Formula C27H30F6N2O2
Molecular Weight 528.5307
Optical Activity UNSPECIFIED
Defined Stereocenters 7 / 7
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DUTASTERIDE

SMILES

C[C@@]12CC[C@@]3([H])[C@@]([H])(CC[C@]4([H])[C@]3(C)C=CC(=N4)O)[C@]2([H])CC[C@]1([H])C(=Nc5cc(ccc5C(F)(F)F)C(F)(F)F)O

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 528.5307
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://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

Curator's Comment:: Avodart (Dutasteride) has been shown to cross the blood brain barrier but does not appear to distribute preferentially to the CSF.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
0.33 µM [EC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
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

1.00612801E12
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
8.91 ng/mL
0.5 mg single, oral
dose: 0.5 mg
route of administration: Oral
experiment type: SINGLE
co-administered: TAMSULOSIN
DUTASTERIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
56.85 ng × h/mL
0.5 mg single, oral
dose: 0.5 mg
route of administration: Oral
experiment type: SINGLE
co-administered: TAMSULOSIN
DUTASTERIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
5.71 h
0.5 mg single, oral
dose: 0.5 mg
route of administration: Oral
experiment type: SINGLE
co-administered: TAMSULOSIN
DUTASTERIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
35 day
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
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
0.5%
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
OverviewDrug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
no
no
no
no
no
no
no
no
no
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.
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.
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.
Page: 9.0
yes [IC50 50 uM]
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.
Page: 8.0
Drug as victim
PubMed

PubMed

TitleDatePubMed
[Dutasteride: main results in the treatment of benign prostatic hyperplasia].
2004 Dec
[Use of 5-alpha-reductase inhibitors in the prevention of prostate cancer].
2004 Dec
Eliciting preferences for drug treatment of lower urinary tract symptoms associated with benign prostatic hyperplasia.
2004 Dec
Preventing diseases of the prostate in the elderly using hormones and nutriceuticals.
2004 Jun
Gateways to clinical trials.
2004 Nov
Gateways to clinical trials.
2005 Apr
Chemoprevention of prostate cancer.
2005 Apr
RE: Effect of the dual 5alpha-reductase inhibitor dutasteride on markers of tumor regression in prostate cancer.
2005 Apr
Selecting therapy for maintaining sexual function in patients with benign prostatic hyperplasia.
2005 Aug
[Effect of dutasteride on reduction of plasma DHT following finasteride therapy in patients with benign prostatic hyperplasia].
2005 Dec
Gateways to clinical trials.
2005 Dec
Noninvasive management of lower urinary tract symptoms and sexual dysfunction associated with benign prostatic hyperplasia in the primary care setting.
2005 Fall
Dutasteride: a novel dual inhibitor of 5alpha-reductase for benign prostatic hyperplasia.
2005 Feb
The dual 5-alpha-reductase inhibitor dutasteride induces atrophic changes and decreases relative cancer volume in human prostate.
2005 Jan
Chemoprevention using dutasteride: the REDUCE trial.
2005 Jan
Combined inhibition of types I and II 5 alpha-reductase selectively augments the basal (nonpulsatile) mode of testosterone secretion in young men.
2005 Jul
Gateways to clinical trials.
2005 Jul-Aug
Gateways to clinical trials.
2005 Jun
Pharmacogenetic analysis of human steroid 5 alpha reductase type II: comparison of finasteride and dutasteride.
2005 Jun
Sexual dysfunction and lower urinary tract symptoms (LUTS) associated with benign prostatic hyperplasia (BPH).
2005 Jun
[Dutasteride (Avodart): a novel 5-alpha reductase inhibitor for treatment of benign prostate hypertrophy].
2005 Mar-Apr
Gateways to clinical trials.
2005 May
Oral testosterone in oil plus dutasteride in men: a pharmacokinetic study.
2005 May
Effect of dutasteride on the detection of prostate cancer in men with benign prostatic hyperplasia.
2005 Nov
Phase III prostate cancer prevention trials: are the costs justified?
2005 Nov 10
Evaluation and medical management of benign prostatic hyperplasia.
2005 Oct
Effect of dutasteride therapy on Doppler US evaluation of prostate: preliminary results.
2005 Oct
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 Oct
Gateways to clinical trials.
2005 Sep
[Novel therapeutics strategies in benign hypertrophy of prostate management].
2005 Sep
Long-term sustained improvement in symptoms of benign prostatic hyperplasia with the dual 5alpha-reductase inhibitor dutasteride: results of 4-year studies.
2005 Sep
[Prevention of prostate cancer].
2005 Sep 9
Effective treatment of female androgenic alopecia with dutasteride.
2005 Sep-Oct
Discovery and clinical development of dutasteride, a potent dual 5alpha-reductase inhibitor.
2006
Inhibitors of 5alpha-reductase in the treatment of benign prostatic hyperplasia.
2006
Treatment and pharmacologic management of BPH in the context of common comorbidities.
2006 Apr
BPH: epidemiology and comorbidities.
2006 Apr
Dutasteride: a dual 5-alpha reductase inhibitor for the treatment of symptomatic benign prostatic hyperplasia.
2006 Apr
Dutasteride, cantharidin, atopiclair, cetuximab, sirolimus, AC-11 and dimericine reviewed in brief.
2006 Feb
Treatment of lower urinary tract symptoms in benign prostatic hyperplasia and its impact on sexual function.
2006 Jan
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 Jan
Development of nomogram to predict acute urinary retention or surgical intervention, with or without dutasteride therapy, in men with benign prostatic hyperplasia.
2006 Jan
Long-term therapy with the dual 5alpha-reductase inhibitor dutasteride is well tolerated in men with symptomatic benign prostatic hyperplasia.
2006 Jan
Gateways to clinical trials.
2006 Jan-Feb
Oral testosterone in oil: pharmacokinetic effects of 5alpha reduction by finasteride or dutasteride and food intake in men.
2006 Jan-Feb
Effects of the dual 5 alpha-reductase inhibitor dutasteride on apoptosis in primary cultures of prostate cancer epithelial cells and cell lines.
2006 Jun 15
Update on prostate cancer chemoprevention.
2006 Mar
Gateways to clinical trials.
2006 May
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 May
Actions of 5alpha-reductase inhibitors on the epididymis.
2006 May 16
Patents

Sample Use Guides

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
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 Fri Jun 25 21:06:59 UTC 2021
Edited
by admin
on Fri Jun 25 21:06:59 UTC 2021
Record UNII
O0J6XJN02I
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DUTASTERIDE
INN   JAN   MART.   MI   ORANGE BOOK   USAN   USP-RS   VANDF   WHO-DD  
USAN   INN  
Official Name English
GI 198745
Code English
AVOLVE
Common Name English
DUASTRIDE
Brand 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
DUTASTERIDE COMPONENT OF JALYN
Brand Name English
JALYN COMPONENT DUTASTERIDE
Brand Name English
DUTASTERIDE [USAN]
Common Name English
DUTASTERIDE [INN]
Common Name English
DUTASTERIDE [MI]
Common Name English
AVODART
Brand 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
DUTASTERIDE [WHO-DD]
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 336
Created by admin on Fri Jun 25 21:06:59 UTC 2021 , Edited by admin on Fri Jun 25 21:06:59 UTC 2021
WHO-VATC QG04CA52
Created by admin on Fri Jun 25 21:06:59 UTC 2021 , Edited by admin on Fri Jun 25 21:06:59 UTC 2021
WHO-ATC G04CB02
Created by admin on Fri Jun 25 21:06:59 UTC 2021 , Edited by admin on Fri Jun 25 21:06:59 UTC 2021
NDF-RT N0000175836
Created by admin on Fri Jun 25 21:06:59 UTC 2021 , Edited by admin on Fri Jun 25 21:06:59 UTC 2021
NCI_THESAURUS C2319
Created by admin on Fri Jun 25 21:06:59 UTC 2021 , Edited by admin on Fri Jun 25 21:06:59 UTC 2021
NDF-RT N0000000126
Created by admin on Fri Jun 25 21:06:59 UTC 2021 , Edited by admin on Fri Jun 25 21:06:59 UTC 2021
WHO-VATC QG04CB02
Created by admin on Fri Jun 25 21:06:59 UTC 2021 , Edited by admin on Fri Jun 25 21:06:59 UTC 2021
WHO-ATC G04CA52
Created by admin on Fri Jun 25 21:06:59 UTC 2021 , Edited by admin on Fri Jun 25 21:06:59 UTC 2021
Code System Code Type Description
EPA CompTox
164656-23-9
Created by admin on Fri Jun 25 21:06:59 UTC 2021 , Edited by admin on Fri Jun 25 21:06:59 UTC 2021
PRIMARY
INN
7586
Created by admin on Fri Jun 25 21:06:59 UTC 2021 , Edited by admin on Fri Jun 25 21:06:59 UTC 2021
PRIMARY
USP_CATALOG
1229922
Created by admin on Fri Jun 25 21:06:59 UTC 2021 , Edited by admin on Fri Jun 25 21:06:59 UTC 2021
PRIMARY USP-RS
PUBCHEM
6918296
Created by admin on Fri Jun 25 21:06:59 UTC 2021 , Edited by admin on Fri Jun 25 21:06:59 UTC 2021
PRIMARY
RXCUI
228790
Created by admin on Fri Jun 25 21:06:59 UTC 2021 , Edited by admin on Fri Jun 25 21:06:59 UTC 2021
PRIMARY RxNorm
CAS
164656-23-9
Created by admin on Fri Jun 25 21:06:59 UTC 2021 , Edited by admin on Fri Jun 25 21:06:59 UTC 2021
PRIMARY
WIKIPEDIA
DUTASTERIDE
Created by admin on Fri Jun 25 21:06:59 UTC 2021 , Edited by admin on Fri Jun 25 21:06:59 UTC 2021
PRIMARY
IUPHAR
7457
Created by admin on Fri Jun 25 21:06:59 UTC 2021 , Edited by admin on Fri Jun 25 21:06:59 UTC 2021
PRIMARY
DRUG BANK
DB01126
Created by admin on Fri Jun 25 21:06:59 UTC 2021 , Edited by admin on Fri Jun 25 21:06:59 UTC 2021
PRIMARY
MESH
C108373
Created by admin on Fri Jun 25 21:06:59 UTC 2021 , Edited by admin on Fri Jun 25 21:06:59 UTC 2021
PRIMARY
EVMPD
SUB06430MIG
Created by admin on Fri Jun 25 21:06:59 UTC 2021 , Edited by admin on Fri Jun 25 21:06:59 UTC 2021
PRIMARY
FDA UNII
O0J6XJN02I
Created by admin on Fri Jun 25 21:06:59 UTC 2021 , Edited by admin on Fri Jun 25 21:06:59 UTC 2021
PRIMARY
NCI_THESAURUS
C47503
Created by admin on Fri Jun 25 21:06:59 UTC 2021 , Edited by admin on Fri Jun 25 21:06:59 UTC 2021
PRIMARY
ChEMBL
CHEMBL1200969
Created by admin on Fri Jun 25 21:06:59 UTC 2021 , Edited by admin on Fri Jun 25 21:06:59 UTC 2021
PRIMARY
DRUG CENTRAL
973
Created by admin on Fri Jun 25 21:06:59 UTC 2021 , Edited by admin on Fri Jun 25 21:06:59 UTC 2021
PRIMARY
MERCK INDEX
M4788
Created by admin on Fri Jun 25 21:06:59 UTC 2021 , Edited by admin on Fri Jun 25 21:06:59 UTC 2021
PRIMARY Merck Index
Related Record Type Details
EXCRETED UNCHANGED
AMOUNT EXCRETED
FECAL
METABOLIC ENZYME -> SUBSTRATE
BINDER->LIGAND
BINDING
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METABOLITE -> PARENT
PLASMA
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IMPURITY -> PARENT
Limit of Residual Solvents
CHROMATOGRAPHIC PURITY (GC)
USP
IMPURITY -> PARENT
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CHROMATOGRAPHIC PURITY (GC)
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IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (GC)
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IMPURITY -> PARENT
Limit of Residual Solvents
CHROMATOGRAPHIC PURITY (GC)
USP
IMPURITY -> PARENT
Limit of Residual Solvents
CHROMATOGRAPHIC PURITY (GC)
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IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (GC)
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IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (GC)
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IMPURITY -> PARENT
Limit of Residual Solvents
CHROMATOGRAPHIC PURITY (GC)
USP
IMPURITY -> PARENT
Limit of Residual Solvents
CHROMATOGRAPHIC PURITY (GC)
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IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (GC)
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IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (GC)
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IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (GC)
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Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Volume of Distribution PHARMACOKINETIC
Biological Half-life PHARMACOKINETIC
Tmax PHARMACOKINETIC ORAL ADMINISTRATION