Dutasteride (CED0004622)

Record Information

Version

1.0

Creation Date

2016-05-22 05:45:07 UTC

Update Date

2026-08-22 07:27:30 UTC

Accession Number

CHEM019002

Identification

Common Name

Dutasteride

Class

Small Molecule

Description

Dutasteride belongs to the androstane steroids, a subclass of steroids and steroid derivatives within the organic compounds. With an average molecular weight of 528.53 g/mol, Dutasteride is a heavy molecule. Its chemical formula is C27H30F6N2O2. This compound is found in healthcare, pharmaceuticals, and veterinary products, where it is used as a drug for benign prostatic hypertrophy. It is administered via oral or topical exposure routes. Dutasteride acts as an inhibitor of three protein targets: 3-oxo-5-alpha-steroid 4-dehydrogenase 1 (SRD5A1), 3-oxo-5-alpha-steroid 4-dehydrogenase 2 (SRD5A2), and Polyprenal reductase (SRD5A3).

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(5alpha,17beta)-N-(2,5-Bis(trifluoromethyl)phenyl)-3-oxo-4-azaandrost-1-ene-17-carboxamide	ChEBI
alpha,alpha,alpha,Alpha',alpha',alpha'-hexafluoro-3-oxo-4-aza-5alpha-androst-1-ene-17beta-carboxy-2',5'-xylidide	ChEBI
Avodart	Kegg
(5a,17b)-N-(2,5-Bis(trifluoromethyl)phenyl)-3-oxo-4-azaandrost-1-ene-17-carboxamide	Generator
(5Α,17β)-N-(2,5-bis(trifluoromethyl)phenyl)-3-oxo-4-azaandrost-1-ene-17-carboxamide	Generator
a,a,a,Alpha',alpha',alpha'-hexafluoro-3-oxo-4-aza-5a-androst-1-ene-17b-carboxy-2',5'-xylidide	Generator
Α,α,α,alpha',alpha',alpha'-hexafluoro-3-oxo-4-aza-5α-androst-1-ene-17β-carboxy-2',5'-xylidide	Generator
17beta-N-(2,5-Bis(trifluoromethyl))phenyl-carbamoyl-4-aza-5alpha-androst-1-en-3-one	HMDB
745, GG	HMDB

Chemical Formula

C₂₇H₃₀F₆N₂O₂

Average Molecular Mass

528.530 g/mol

Monoisotopic Mass

528.221 g/mol

CAS Registry Number

164656-23-9

IUPAC Name

(1S,2R,7R,10S,11S,14S,15S)-N-[2,5-bis(trifluoromethyl)phenyl]-2,15-dimethyl-5-oxo-6-azatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-3-ene-14-carboxamide

Traditional Name

dutasteride

SMILES

[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC[C@@]4([H])NC(=O)C=C[C@]4(C)[C@@]3([H])CC[C@]12C)C(=O)NC1=CC(=CC=C1C(F)(F)F)C(F)(F)F

InChI Identifier

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

InChI Key

JWJOTENAMICLJG-QWBYCMEYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as androgens and derivatives. These are 3-hydroxylated C19 steroid hormones. They are known to favor the development of masculine characteristics. They also show profound effects on scalp and body hair in humans.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Androstane steroids

Direct Parent

Androgens and derivatives

Alternative Parents

Substituents

Androgen-skeleton
3-oxosteroid
3-oxo-4-azasteroid
3-oxo-5-alpha-steroid
Oxosteroid
4-azasteroid
Azasteroid
Trifluoromethylbenzene
Anilide
N-arylamide
Monocyclic benzene moiety
Benzenoid
Carboxamide group
Lactam
Secondary carboxylic acid amide
Azacycle
Carboxylic acid derivative
Organoheterocyclic compound
Organohalogen compound
Alkyl halide
Alkyl fluoride
Organic nitrogen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organofluoride
Organonitrogen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

delta-lactam (CHEBI:521033 )
aza-steroid (CHEBI:521033 )
(trifluoromethyl)benzenes (CHEBI:521033 )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Organoleptic Effects

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.00091 g/L	ALOGPS
logP	5.45	ALOGPS
logP	5.79	ChemAxon
logS	-5.8	ALOGPS
pKa (Strongest Acidic)	12.56	ChemAxon
pKa (Strongest Basic)	2.17	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	58.2 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	127.9 m³·mol⁻¹	ChemAxon
Polarizability	50.13 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-0r00-0695380000-37d765dda5ec5e49b0fd	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-004i-0010190000-3420a2295d7f96d1d3c8	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0w4i-0566290000-0b4c4c43a1363f4cde3c	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0fka-2490010000-583fa26158a6ee3f69db	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-004i-0000090000-6590720379fb16a92f43	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-004i-1050090000-ceadcb8345b10a444f0f	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0kbf-2190000000-a71ffb6ab0e5ccfce59b	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-004i-0001090000-69b701f7be2c2462c87c	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00b9-0594370000-8a9228b409aa1db36766	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00xr-0590000000-e41abf0c7f5b9d8fd56d	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-004i-0000090000-754362aa78fcb9885806	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-004i-1020090000-9af76f2aa77fb2cdadf5	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-004i-0040090000-5354ee6cb84f313f4a81	Not Available	View Spectrum

Toxicity Profile

Mechanism of Toxicity

Not Available

Carcinogenicity (IARC Classification)

Not Available

Minimum Risk Level

Not Available

Symptoms

Not Available

Treatment

Not Available

Toxicity Values

Toxicity Value	Unit	Value Range	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Reference
216.0	Log mg/kg	[120:380]	Rat	LD50	oral	predicted	Not Available

Health Effects

Health Effect	Relationship	Direction	Reference

Exposure Sources

Source ID	Source	Sector	Reference
327	Drugs used in benign prostatic hypertrophy	Healthcare, pharmaceuticals & veterinary products	Not Available

Pathways

2 pathways

Dutasteride Action Pathway

Dutasteride Drug Metabolism Action Pathway

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	Macrophage metalloelastase	P39900	Humans	Predicted (SEA)	786.355
Click to view 3D structure	A disintegrin and metalloproteinase with thrombospondin motifs 5	Q9UNA0	Humans	Predicted (SEA)	233.937
Click to view 3D structure	A disintegrin and metalloproteinase with thrombospondin motifs 4	O75173	Humans	Predicted (SEA)	291.701
Click to view 3D structure	Progesterone receptor	Q690N0	Bos taurus	Predicted (SEA)	32.2296
Click to view 3D structure	Estrogen receptor	P03372	Humans	Predicted (SEA)	445.22
Click to view 3D structure	Voltage-gated inwardly rectifying potassium channel KCNH2	Q12809	Humans	Predicted (SEA)	5046.19
Click to view 3D structure	Progesterone receptor	P06401	Humans	Predicted (SEA)	286.407
Click to view 3D structure	3-oxo-5-alpha-steroid 4-dehydrogenase 2	P31213	Humans	Predicted (SEA)	0.0778492
Click to view 3D structure	3-oxo-5-alpha-steroid 4-dehydrogenase 1	P18405	Humans	Predicted (SEA)	0.0778492
Click to view 3D structure	3-oxo-5-alpha-steroid 4-dehydrogenase 1	P24008	Rattus norvegicus	Predicted (SEA)	0.0778492
Click to view 3D structure	3-oxo-5-alpha-steroid 4-dehydrogenase 2	P31214	Rattus norvegicus	Predicted (SEA)	0.0778492
Click to view 3D structure	3 beta-hydroxysteroid dehydrogenase/Delta 5-->4-isomerase type 1	P14060	Humans	Predicted (SEA)	1.32344
Click to view 3D structure	Cytochrome P450 2C9	P11712	Humans	Predicted (SEA)	478.851
Click to view 3D structure	Glycine receptor subunit alpha-1	P23415	Humans	Predicted (SEA)	0.700643
Click to view 3D structure	Cytochrome P450 2C19	P33261	Humans	Predicted (SEA)	432.063
Click to view 3D structure	Gamma-aminobutyric acid type B receptor subunit 1	Q9Z0U4	Rattus norvegicus	Predicted (SEA)	5.91654
Click to view 3D structure	Sex hormone-binding globulin	P04278	Humans	Predicted (SEA)	27.0915
Click to view 3D structure	Corticosteroid-binding globulin	P08185	Humans	Predicted (SEA)	23.744
Click to view 3D structure	Androgen receptor	P15207	Rattus norvegicus	Predicted (SEA)	51.7697
Click to view 3D structure	Androgen receptor	P19091	Mus musculus	Predicted (SEA)	18.9952
Click to view 3D structure	G-protein coupled bile acid receptor 1	Q8TDU6	Humans	Predicted (SEA)	66.7946
Click to view 3D structure	Androgen receptor	P10275	Humans	Predicted (SEA)	163.561
Click to view 3D structure	Glucocorticoid receptor	P04150	Humans	Predicted (SEA)	125.571
Click to view 3D structure	Aldo-keto reductase family 1 member B10	O60218	Humans	Predicted (SEA)	115.528
Click to view 3D structure	Mineralocorticoid receptor	P08235	Humans	Predicted (SEA)	81.7417