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Details

Stereochemistry ABSOLUTE
Molecular Formula C19H14F3N3O3
Molecular Weight 389.328
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ENOBOSARM

SMILES

C[C@](O)(COC1=CC=C(C=C1)C#N)C(=O)NC2=CC(=C(C=C2)C#N)C(F)(F)F

InChI

InChIKey=JNGVJMBLXIUVRD-SFHVURJKSA-N
InChI=1S/C19H14F3N3O3/c1-18(27,11-28-15-6-2-12(9-23)3-7-15)17(26)25-14-5-4-13(10-24)16(8-14)19(20,21)22/h2-8,27H,11H2,1H3,(H,25,26)/t18-/m0/s1

HIDE SMILES / InChI
Molecular Formula C19H14F3N3O3
Molecular Weight 389.328
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: Description was created using several sources including: https://www.ncbi.nlm.nih.gov/pubmed/23499390 | https://www.ncbi.nlm.nih.gov/pubmed/24490605 | https://www.ncbi.nlm.nih.gov/pubmed/24633910 | https://www.ncbi.nlm.nih.gov/pubmed/26393303

MK-2866 (Gtx-024) is a selective androgen receptor modulator (SARM) for treatment of conditions such as muscle wasting and osteoporosis. It is a non-steroidal agent with anabolic activity designed to work like testosterone, thus promoting and/or maintaining libido, fertility, prostate growth, and muscle growth and strength. Mimicking testosterone's action, this agent may increase lean body mass, thereby ameliorating muscle wasting in the hypermetabolic state of cancer cachexia.

Originator

GTx|Merck
1
Curator's Comment: # GTx and Merck & Co., Inc.

Approval Year

Unknown
149124
Targets

Targets

Primary TargetPharmacologyConditionPotency
Modulator
846
 3.8 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Phase II
1147
Unknown

Approved Use

Unknown
Primary
Phase III
665
Unknown

Approved Use

Unknown
Primary
Phase II
1147
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
57.6 ng/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/27105861
3 mg 1 times / day single, oral
dose: 3 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ENOBOSARM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
779.5 ng × h/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/27105861
3 mg 1 times / day single, oral
dose: 3 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ENOBOSARM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
22 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/27105861
3 mg 1 times / day single, oral
dose: 3 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ENOBOSARM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
3 mg 1 times / day multiple, oral
Highest studied dose
Dose: 3 mg, 1 times / day
Route: oral
Route: multiple
Dose: 3 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/22031847
healthy, ADULT
Health Status: healthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/22031847
Disc. AE: ALT increased...
AEs leading to
discontinuation/dose reduction:
ALT increased (4.2%)
Sources:
https://pubmed.ncbi.nlm.nih.gov/22031847
3 mg 1 times / day multiple, oral
Highest studied dose
Dose: 3 mg, 1 times / day
Route: oral
Route: multiple
Dose: 3 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/23499390
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/23499390
Sources:
https://pubmed.ncbi.nlm.nih.gov/23499390
AEs

AEs

AESignificanceDosePopulation
ALT increased 4.2%
Disc. AE
3 mg 1 times / day multiple, oral
Highest studied dose
Dose: 3 mg, 1 times / day
Route: oral
Route: multiple
Dose: 3 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/22031847
healthy, ADULT
Health Status: healthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/22031847
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG
inhibitor
2252

substrate
1946
inhibitor
2438

substrate
1193
inhibitor
2507

substrate
1388

OverviewOther

Other InhibitorOther SubstrateOther Inducer
CYP2C19
2057

CYP1A2
2153

BCRP
910

OATP1B1
1079
UGT1A8
323

CYP2C19
1119

CYP1A2
1197

UGT2B7
456

UGT1A4
399

UGT1A6
343

UGT2B15
236

UGT1A10
331

UGT1A1
479

P-gp
2052
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
CYP1A2
2333
 no [IC50 >10 uM]
CYP2D6
2546
 no [IC50 >10 uM]
CYP3A4
2633
 no [IC50 >10 uM]
OATP1B1
1095
 no
CYP2C19
2141
 yes [IC50 0.7 uM]
BCRP
985
 yes [IC50 1.31 uM]
yes (co-administration study)
Comment: Increased rosubastatin Cmax and AUCinf by 29% and 18%.
CYP2C9
2497
 yes [IC50 1.6 uM]
yes (co-administration study)
Comment: Decreased celecoxib Cmax and AUCinf by 13% and 10%.
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
CYP3A4
1946
 major
yes (co-administration study)
Comment: Rifampicin decreased Cmax and AUCinf by 23% and 43%.
UGT1A1
479
 major
yes (co-administration study)
Comment: Probenecid increased AUCinf by 50% and decreased Cmax by 6.7%.
UGT2B7
456
 major
yes (co-administration study)
Comment: Probenecid increased AUCinf by 50% and decreased Cmax by 6.7%.
CYP2C19
1119
 minor
CYP2D6
1388
 minor
UGT1A10
331
 minor
UGT1A4
399
 minor
UGT1A6
343
 minor
UGT1A8
323
 minor
UGT2B15
236
 minor
CYP1A2
1197
 no
CYP2C9
1193
 no
P-gp
2052
 no
PubMed

PubMed

TitleDatePubMed
Enobosarm (GTx-024) Modulates Adult Skeletal Muscle Mass Independently of the Androgen Receptor in the Satellite Cell Lineage.
2015-12
Enobosarm (GTx-024, S-22): a potential treatment for cachexia.
2014-02
Absorption, distribution, metabolism and excretion of the novel SARM GTx-024 [(S)-N-(4-cyano-3-(trifluoromethyl)phenyl)-3-(4-cyanophenoxy)-2-hydroxy-2-methylpropanamide] in rats.
2013-11
Effects of enobosarm on muscle wasting and physical function in patients with cancer: a double-blind, randomised controlled phase 2 trial.
2013-04
Nonsteroidal selective androgen receptor modulator Ostarine in cancer cachexia.
2009-10
Patents

Patents

US2014134274
1
US6569896
1

Sample Use Guides

In Vivo Use Guide
1 or 3 mg Gtx-024 once daily for 16 weeks in patients with cancer induced muscle loss, (cancer cachexia)
Route of Administration: Oral
In Vitro Use Guide
Enobosarm at the concentration of 10 nM modulates the transcriptional activity of AR in CV-1 cells cotransfected with a human AR expression vector, a luciferase reporter vector, and a control β-galactosidase vector, with 94%-100% relative activity of the transcriptional activation observed for 1 nM DHT.
Substance Class Chemical
Created
by admin
on Wed Apr 02 08:34:28 GMT 2025
Edited
by admin
on Wed Apr 02 08:34:28 GMT 2025
Record UNII
O3571H3R8N
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ENOBOSARM
INN   USAN   WHO-DD  
USAN   INN  
Official Name English
enobosarm [INN]
Preferred Name English
PROPANAMIDE, 3-(4-CYANOPHENOXY)-N-(4-CYANO-3-(TRIFLUOROMETHYL)PHENYL)-2-HYDROXY-2-METHYL-, (2S)-
Systematic Name English
ENOBOSARM [USAN]
Common Name English
GTX-024
Code English
Enobosarm [WHO-DD]
Common Name English
OSTARINE
Brand Name English
MK-2866
Code English
Classification Tree Code System Code
DSLD 3985 (Number of products:13)
Created by admin on Wed Apr 02 08:34:28 GMT 2025 , Edited by admin on Wed Apr 02 08:34:28 GMT 2025
WIKIPEDIA Designer-drugs-Enobosarm
Created by admin on Wed Apr 02 08:34:28 GMT 2025 , Edited by admin on Wed Apr 02 08:34:28 GMT 2025
NCI_THESAURUS C147920
Created by admin on Wed Apr 02 08:34:28 GMT 2025 , Edited by admin on Wed Apr 02 08:34:28 GMT 2025
Code System Code Type Description
EPA CompTox
DTXSID30233006
Created by admin on Wed Apr 02 08:34:28 GMT 2025 , Edited by admin on Wed Apr 02 08:34:28 GMT 2025
PRIMARY
FDA UNII
O3571H3R8N
Created by admin on Wed Apr 02 08:34:28 GMT 2025 , Edited by admin on Wed Apr 02 08:34:28 GMT 2025
PRIMARY
INN
9596
Created by admin on Wed Apr 02 08:34:28 GMT 2025 , Edited by admin on Wed Apr 02 08:34:28 GMT 2025
PRIMARY
SMS_ID
100000168546
Created by admin on Wed Apr 02 08:34:28 GMT 2025 , Edited by admin on Wed Apr 02 08:34:28 GMT 2025
PRIMARY
ChEMBL
CHEMBL1738889
Created by admin on Wed Apr 02 08:34:28 GMT 2025 , Edited by admin on Wed Apr 02 08:34:28 GMT 2025
PRIMARY
CAS
841205-47-8
Created by admin on Wed Apr 02 08:34:28 GMT 2025 , Edited by admin on Wed Apr 02 08:34:28 GMT 2025
PRIMARY
USAN
YY-84
Created by admin on Wed Apr 02 08:34:28 GMT 2025 , Edited by admin on Wed Apr 02 08:34:28 GMT 2025
PRIMARY
WIKIPEDIA
ENOBOSARM
Created by admin on Wed Apr 02 08:34:28 GMT 2025 , Edited by admin on Wed Apr 02 08:34:28 GMT 2025
PRIMARY
PUBCHEM
11326715
Created by admin on Wed Apr 02 08:34:28 GMT 2025 , Edited by admin on Wed Apr 02 08:34:28 GMT 2025
PRIMARY
DRUG BANK
DB12078
Created by admin on Wed Apr 02 08:34:28 GMT 2025 , Edited by admin on Wed Apr 02 08:34:28 GMT 2025
PRIMARY
EVMPD
SUB182072
Created by admin on Wed Apr 02 08:34:28 GMT 2025 , Edited by admin on Wed Apr 02 08:34:28 GMT 2025
PRIMARY
RXCUI
2168587
Created by admin on Wed Apr 02 08:34:28 GMT 2025 , Edited by admin on Wed Apr 02 08:34:28 GMT 2025
PRIMARY
NCI_THESAURUS
C69161
Created by admin on Wed Apr 02 08:34:28 GMT 2025 , Edited by admin on Wed Apr 02 08:34:28 GMT 2025
PRIMARY
Related Record Type Details
ANDROGEN RECEPTOR
TARGET -> AGONIST
SARM
BINDING
Ki
Related Record Type Details
Structure of ENOBOSARM
ACTIVE MOIETY
NIH
NCATS
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ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
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