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Details

Stereochemistry ACHIRAL
Molecular Formula C25H26N7O8P.C4H11NO3
Molecular Weight 704.6248
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of FOSTEMSAVIR TROMETHAMINE

SMILES

NC(CO)(CO)CO.COC1=CN=C(N2C=NC(C)=N2)C3=C1C(=CN3COP(O)(O)=O)C(=O)C(=O)N4CCN(CC4)C(=O)C5=CC=CC=C5

InChI

InChIKey=RRGJSMBMTOKHTE-UHFFFAOYSA-N
InChI=1S/C25H26N7O8P.C4H11NO3/c1-16-27-14-32(28-16)23-21-20(19(39-2)12-26-23)18(13-31(21)15-40-41(36,37)38)22(33)25(35)30-10-8-29(9-11-30)24(34)17-6-4-3-5-7-17;5-4(1-6,2-7)3-8/h3-7,12-14H,8-11,15H2,1-2H3,(H2,36,37,38);6-8H,1-3,5H2

HIDE SMILES / InChI

Molecular Formula C4H11NO3
Molecular Weight 121.135
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C25H26N7O8P
Molecular Weight 583.4898
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Fostemsavir (BMS-663068) is an investigational attachment inhibitor with a unique mechanism of action. It is a prodrug of temsavir, which binds to HIV envelope glycoprotein 120 (gp120), thereby preventing viral attachment to the host CD4 cell surface receptor. In the absence of effective binding of HIV gp120 with the host CD4 receptor, HIV does not enter the host cell. Because fostemsavir has a novel mechanism of action, the drug should have full activity against HIV strains that have developed resistance to other classes of antiretroviral medications. In a phase 2b study of treatment-experienced individuals, fostemsavir appeared to be well tolerated. Phase 3 studies are ongoing.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
PubMed

PubMed

TitleDatePubMed
Safety and efficacy of the HIV-1 attachment inhibitor prodrug BMS-663068 in treatment-experienced individuals: 24 week results of AI438011, a phase 2b, randomised controlled trial.
2015 Oct
Model-Based Phase 3 Dose Selection for HIV-1 Attachment Inhibitor Prodrug BMS-663068 in HIV-1-Infected Patients: Population Pharmacokinetics/Pharmacodynamics of the Active Moiety, BMS-626529.
2016 May
Safety and efficacy of the HIV-1 attachment inhibitor prodrug fostemsavir in antiretroviral-experienced subjects: week 48 analysis of AI438011, a Phase IIb, randomized controlled trial.
2017
[What can new substances offer?]
2017 Jun
Current Status of the Pharmacokinetics and Pharmacodynamics of HIV-1 Entry Inhibitors and HIV Therapy.
2017 Oct 16
Patents

Sample Use Guides

In Vivo Use Guide
A phase 2b trial enrolled treatment-experienced adults with HIV infection and randomized study subjects to one of four doses of fostemsavir (400 mg twice daily, 800 mg twice daily, 600 mg once daily, or 1200 mg once daily).
Route of Administration: Oral
In Vitro Use Guide
BMS-626529 (an active moiety of BMS-663068) exhibits an average EC50 against LAI of 0.7 +/-0.4 nM.
Substance Class Chemical
Created
by admin
on Tue Oct 22 01:27:19 UTC 2019
Edited
by admin
on Tue Oct 22 01:27:19 UTC 2019
Record UNII
2X513P36U0
Record Status Validated (UNII)
Record Version
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Name Type Language
FOSTEMSAVIR TROMETHAMINE
USAN  
USAN  
Official Name English
(3-(2-(4-BENZOYLPIPERAZIN-1-YL)-2-OXOACETYL)-4-METHOXY-7-(3-METHYL-1H-1,2,4-TRIAZOL-1-YL)-1H-PYRROLO(2,3-C)PYRIDIN-1-YL)METHYL (ESTER) AND 1,3-DIHYDROXY-2-(HYDROXYMETHYL)PROPAN-2-AMINIUM (SALT) HYDROGEN PHOSPHATE
Systematic Name English
1,2-ETHANEDIONE, 1-(4-BENZOYL-1-PIPERAZINYL)-2-(4-METHOXY-7-(3-METHYL-1H-1,2,4-TRIAZOL-1-YL)-1-((PHOSPHONOOXY)METHYL)-1H-PYRROLO(2,3-C)PYRIDIN-3-YL)-, COMPD. WITH 2-AMINO-2-(HYDROXYMETHYL)-1,3-PROPANEDIOL (1:1)
Systematic Name English
FOSTEMSAVIR TROMETAMOL [WHO-DD]
Common Name English
BMS-663068-03
Code English
FOSTEMSAVIR TROMETHAMINE [USAN]
Common Name English
GSK3684934A
Code English
BMS-663068 TROMETHAMINE
Code English
GSK-3684934A
Code English
Code System Code Type Description
ChEMBL
CHEMBL3301594
Created by admin on Tue Oct 22 01:27:19 UTC 2019 , Edited by admin on Tue Oct 22 01:27:19 UTC 2019
PRIMARY
PUBCHEM
46892186
Created by admin on Tue Oct 22 01:27:19 UTC 2019 , Edited by admin on Tue Oct 22 01:27:19 UTC 2019
PRIMARY
CAS
864953-39-9
Created by admin on Tue Oct 22 01:27:19 UTC 2019 , Edited by admin on Tue Oct 22 01:27:19 UTC 2019
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY