U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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#N)C(=C2)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

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

Approval Year

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Modulator
828
 3.8 nM [Ki]
Modulator
828
 3.8 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Phase II
1132
Unknown

Approved Use

Unknown
Primary
Phase III
656
Unknown

Approved Use

Unknown
Primary
Phase II
1132
Unknown

Approved Use

Unknown
Primary
Phase III
656
Unknown

Approved Use

Unknown
Primary
Phase II
1132
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
Page: p.155
healthy, ADULT
n = 24
Health Status: healthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Population Size: 24
Sources:
https://pubmed.ncbi.nlm.nih.gov/22031847
Page: p.155
Disc. AE: ALT increased...
AEs leading to
discontinuation/dose reduction:
ALT increased (4.2%)
Sources:
https://pubmed.ncbi.nlm.nih.gov/22031847
Page: p.155
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
Page: p.7
unhealthy, ADULT
n = 54
Health Status: unhealthy
Condition: cancer
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Population Size: 54
Sources:
https://pubmed.ncbi.nlm.nih.gov/23499390
Page: p.7
Sources:
https://pubmed.ncbi.nlm.nih.gov/23499390
Page: p.7
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
Page: p.155
healthy, ADULT
n = 24
Health Status: healthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Population Size: 24
Sources:
https://pubmed.ncbi.nlm.nih.gov/22031847
Page: p.155
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG
inhibitor
1587

substrate
1737
inhibitor
1767

substrate
1037
inhibitor
1852

substrate
1217

OverviewOther

Other InhibitorOther SubstrateOther Inducer
CYP1A2
1524

CYP2C19
1478

BCRP
699

OATP1B1
788
UGT1A8
283

CYP2C19
991

CYP1A2
1054

UGT2B7
389

UGT1A4
347

UGT1A6
307

UGT2B15
203

UGT1A10
291

UGT1A1
418

P-gp
1537
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
CYP1A2
1692
 no [IC50 >10 uM]
CYP2D6
1891
 no [IC50 >10 uM]
CYP3A4
1925
 no [IC50 >10 uM]
OATP1B1
803
 no
BCRP
773
 yes [IC50 1.31 uM]
yes (co-administration study)
Comment: Increased rosubastatin Cmax and AUCinf by 29% and 18%.
CYP2C9
1819
 yes [IC50 1.6 uM]
yes (co-administration study)
Comment: Decreased celecoxib Cmax and AUCinf by 13% and 10%.
CYP2C19
1553
 yess [IC50 0.7 uM]
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
CYP3A4
1737
 major
yes (co-administration study)
Comment: Rifampicin decreased Cmax and AUCinf by 23% and 43%.
UGT1A1
418
 major
yes (co-administration study)
Comment: Probenecid increased AUCinf by 50% and decreased Cmax by 6.7%.
UGT2B7
389
 major
yes (co-administration study)
Comment: Probenecid increased AUCinf by 50% and decreased Cmax by 6.7%.
CYP2C19
991
 minor
CYP2D6
1217
 minor
UGT1A10
291
 minor
UGT1A4
347
 minor
UGT1A6
307
 minor
UGT1A8
283
 minor
UGT2B15
203
 minor
CYP1A2
1054
 no
CYP2C9
1037
 no
P-gp
1537
 no
PubMed

PubMed

TitleDatePubMed
Nonsteroidal selective androgen receptor modulator Ostarine in cancer cachexia.
2009 Oct
Effects of enobosarm on muscle wasting and physical function in patients with cancer: a double-blind, randomised controlled phase 2 trial.
2013 Apr
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 Nov
Enobosarm (GTx-024, S-22): a potential treatment for cachexia.
2014 Feb
Enobosarm (GTx-024) Modulates Adult Skeletal Muscle Mass Independently of the Androgen Receptor in the Satellite Cell Lineage.
2015 Dec
Study Design and Rationale for the Phase 3 Clinical Development Program of Enobosarm, a Selective Androgen Receptor Modulator, for the Prevention and Treatment of Muscle Wasting in Cancer Patients (POWER Trials).
2016 Jun
Analytical strategies to detect enobosarm administration in bovines.
2017 Apr
Patents

Patents

US2014018433
1
US2014134274
1
US6569896
1
US8741951
1

Sample Use Guides

In Vivo Use Guide
Enobosarm dosage of three soft gels once daily to equal 9mg
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.
Name Type Language
ENOBOSARM
INN   USAN   WHO-DD  
USAN   INN  
Official 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 [INN]
Common Name 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 Sat Dec 16 16:56:23 GMT 2023 , Edited by admin on Sat Dec 16 16:56:23 GMT 2023
WIKIPEDIA Designer-drugs-Enobosarm
Created by admin on Sat Dec 16 16:56:23 GMT 2023 , Edited by admin on Sat Dec 16 16:56:23 GMT 2023
NCI_THESAURUS C147920
Created by admin on Sat Dec 16 16:56:23 GMT 2023 , Edited by admin on Sat Dec 16 16:56:23 GMT 2023
Code System Code Type Description
EPA CompTox
DTXSID30233006
Created by admin on Sat Dec 16 16:56:23 GMT 2023 , Edited by admin on Sat Dec 16 16:56:23 GMT 2023
PRIMARY
FDA UNII
O3571H3R8N
Created by admin on Sat Dec 16 16:56:23 GMT 2023 , Edited by admin on Sat Dec 16 16:56:23 GMT 2023
PRIMARY
INN
9596
Created by admin on Sat Dec 16 16:56:23 GMT 2023 , Edited by admin on Sat Dec 16 16:56:23 GMT 2023
PRIMARY
SMS_ID
100000168546
Created by admin on Sat Dec 16 16:56:23 GMT 2023 , Edited by admin on Sat Dec 16 16:56:23 GMT 2023
PRIMARY
ChEMBL
CHEMBL1738889
Created by admin on Sat Dec 16 16:56:23 GMT 2023 , Edited by admin on Sat Dec 16 16:56:23 GMT 2023
PRIMARY
CAS
841205-47-8
Created by admin on Sat Dec 16 16:56:23 GMT 2023 , Edited by admin on Sat Dec 16 16:56:23 GMT 2023
PRIMARY
USAN
YY-84
Created by admin on Sat Dec 16 16:56:23 GMT 2023 , Edited by admin on Sat Dec 16 16:56:23 GMT 2023
PRIMARY
WIKIPEDIA
ENOBOSARM
Created by admin on Sat Dec 16 16:56:23 GMT 2023 , Edited by admin on Sat Dec 16 16:56:23 GMT 2023
PRIMARY
PUBCHEM
11326715
Created by admin on Sat Dec 16 16:56:23 GMT 2023 , Edited by admin on Sat Dec 16 16:56:23 GMT 2023
PRIMARY
DRUG BANK
DB12078
Created by admin on Sat Dec 16 16:56:23 GMT 2023 , Edited by admin on Sat Dec 16 16:56:23 GMT 2023
PRIMARY
EVMPD
SUB182072
Created by admin on Sat Dec 16 16:56:23 GMT 2023 , Edited by admin on Sat Dec 16 16:56:23 GMT 2023
PRIMARY
RXCUI
2168587
Created by admin on Sat Dec 16 16:56:23 GMT 2023 , Edited by admin on Sat Dec 16 16:56:23 GMT 2023
PRIMARY
NCI_THESAURUS
C69161
Created by admin on Sat Dec 16 16:56:23 GMT 2023 , Edited by admin on Sat Dec 16 16:56:23 GMT 2023
PRIMARY
ACTIVE MOIETY
Structure of ENOBOSARM
NIH
NCATS
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