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Details

Stereochemistry ACHIRAL
Molecular Formula C25H26N7O8P.2H2O
Molecular Weight 619.5204
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of FOSTEMSAVIR DIHYDRATE

SMILES

O.O.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=IHIJOICKAIGEIR-UHFFFAOYSA-N
InChI=1S/C25H26N7O8P.2H2O/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;;/h3-7,12-14H,8-11,15H2,1-2H3,(H2,36,37,38);2*1H2

HIDE SMILES / InChI

Molecular Formula H2O
Molecular Weight 18.0153
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 12:33:48 UTC 2019
Edited
by admin
on Tue Oct 22 12:33:48 UTC 2019
Record UNII
Z3P1PLZ348
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
FOSTEMSAVIR DIHYDRATE
Common 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)-, HYDRATE (1:2)
Systematic Name English
BMS-663068 DIHYDRATE
Common Name English
Code System Code Type Description
PUBCHEM
76956413
Created by admin on Tue Oct 22 12:33:48 UTC 2019 , Edited by admin on Tue Oct 22 12:33:48 UTC 2019
PRIMARY
CAS
942117-71-7
Created by admin on Tue Oct 22 12:33:48 UTC 2019 , Edited by admin on Tue Oct 22 12:33:48 UTC 2019
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY