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Details

Stereochemistry ABSOLUTE
Molecular Formula C19H14F3N3O3
Molecular Weight 389.3287
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ENOBOSARM

SMILES

C[C@](COc1ccc(cc1)C#N)(C(=Nc2ccc(C#N)c(c2)C(F)(F)F)O)O

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 389.3287
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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
3.8 nM [Ki]
3.8 nM [Ki]
Conditions
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
57.6 ng/mL
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
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
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: Page: p.155
healthy, ADULT
n = 24
Health Status: healthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Population Size: 24
Sources: Page: p.155
Disc. AE: ALT increased...
AEs leading to
discontinuation/dose reduction:
ALT increased (4.2%)
Sources: 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: 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: 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: Page: p.155
healthy, ADULT
n = 24
Health Status: healthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Population Size: 24
Sources: Page: p.155
OverviewDrug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
no [IC50 >10 uM]
no [IC50 >10 uM]
no [IC50 >10 uM]
no
yes [IC50 1.31 uM]
yes (co-administration study)
Comment: Increased rosubastatin Cmax and AUCinf by 29% and 18%.
yes [IC50 1.6 uM]
yes (co-administration study)
Comment: Decreased celecoxib Cmax and AUCinf by 13% and 10%.
yess [IC50 0.7 uM]
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
major
yes (co-administration study)
Comment: Rifampicin decreased Cmax and AUCinf by 23% and 43%.
major
yes (co-administration study)
Comment: Probenecid increased AUCinf by 50% and decreased Cmax by 6.7%.
major
yes (co-administration study)
Comment: Probenecid increased AUCinf by 50% and decreased Cmax by 6.7%.
minor
minor
minor
minor
minor
minor
minor
no
no
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

Sample Use Guides

Enobosarm dosage of three soft gels once daily to equal 9mg
Route of Administration: Oral
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 Sat Jun 26 10:18:16 UTC 2021
Edited
by admin
on Sat Jun 26 10:18:16 UTC 2021
Record UNII
O3571H3R8N
Record Status Validated (UNII)
Record Version
  • Download
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 [WHO-DD]
Common Name English
ENOBOSARM [INN]
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 Jun 26 10:18:16 UTC 2021 , Edited by admin on Sat Jun 26 10:18:16 UTC 2021
NCI_THESAURUS C147920
Created by admin on Sat Jun 26 10:18:16 UTC 2021 , Edited by admin on Sat Jun 26 10:18:16 UTC 2021
Code System Code Type Description
EPA CompTox
841205-47-8
Created by admin on Sat Jun 26 10:18:16 UTC 2021 , Edited by admin on Sat Jun 26 10:18:16 UTC 2021
PRIMARY
FDA UNII
O3571H3R8N
Created by admin on Sat Jun 26 10:18:16 UTC 2021 , Edited by admin on Sat Jun 26 10:18:16 UTC 2021
PRIMARY
INN
9596
Created by admin on Sat Jun 26 10:18:16 UTC 2021 , Edited by admin on Sat Jun 26 10:18:16 UTC 2021
PRIMARY
ChEMBL
CHEMBL1738889
Created by admin on Sat Jun 26 10:18:16 UTC 2021 , Edited by admin on Sat Jun 26 10:18:16 UTC 2021
PRIMARY
CAS
841205-47-8
Created by admin on Sat Jun 26 10:18:16 UTC 2021 , Edited by admin on Sat Jun 26 10:18:16 UTC 2021
PRIMARY
WIKIPEDIA
ENOBOSARM
Created by admin on Sat Jun 26 10:18:16 UTC 2021 , Edited by admin on Sat Jun 26 10:18:16 UTC 2021
PRIMARY
PUBCHEM
11326715
Created by admin on Sat Jun 26 10:18:16 UTC 2021 , Edited by admin on Sat Jun 26 10:18:16 UTC 2021
PRIMARY
DRUG BANK
DB12078
Created by admin on Sat Jun 26 10:18:16 UTC 2021 , Edited by admin on Sat Jun 26 10:18:16 UTC 2021
PRIMARY
EVMPD
SUB182072
Created by admin on Sat Jun 26 10:18:16 UTC 2021 , Edited by admin on Sat Jun 26 10:18:16 UTC 2021
PRIMARY
RXCUI
2168587
Created by admin on Sat Jun 26 10:18:16 UTC 2021 , Edited by admin on Sat Jun 26 10:18:16 UTC 2021
PRIMARY
NCI_THESAURUS
C69161
Created by admin on Sat Jun 26 10:18:16 UTC 2021 , Edited by admin on Sat Jun 26 10:18:16 UTC 2021
PRIMARY
Related Record Type Details
TARGET -> AGONIST
BINDING AFFINITY
BINDING
Ki
Related Record Type Details
ACTIVE MOIETY