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Details

Stereochemistry ACHIRAL
Molecular Formula C24H23N7O4
Molecular Weight 473.4839
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TEMSAVIR

SMILES

COC1=CN=C(N2C=NC(C)=N2)C3=C1C(=CN3)C(=O)C(=O)N4CCN(CC4)C(=O)C5=CC=CC=C5

InChI

InChIKey=QRPZBKAMSFHVRW-UHFFFAOYSA-N
InChI=1S/C24H23N7O4/c1-15-27-14-31(28-15)22-20-19(18(35-2)13-26-22)17(12-25-20)21(32)24(34)30-10-8-29(9-11-30)23(33)16-6-4-3-5-7-16/h3-7,12-14,25H,8-11H2,1-2H3

HIDE SMILES / InChI

Molecular Formula C24H23N7O4
Molecular Weight 473.4839
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Temsavir (BMS-626529) is an attachment inhibitor (AI) in clinical development (administered as prodrug BMS-663068) that binds to HIV-1 gp120. Temsavir displays in vitro activity against HIV-1 envelopes with C-C chemokine receptor type 5 (CCR5-), C-X-C chemokine receptor type 4 (CXCR4), and dual tropism. It also is active against almost all HIV-1 subtypes tested except for subtype CRF01-AE and possibly group O. Temsavir can inhibit both CD4-induced and CD4-independent formation of the "open state" four-stranded gp120 bridging sheet, and the subsequent formation and exposure of the chemokine co-receptor binding site. This unique mechanism of action prevents the initial interaction of HIV-1 with the host CD4+ T cell, and subsequent HIV-1 binding and entry. Temsavir is administered as a phosphonooxymethyl ester prodrug (BMS-663068), which was developed to improve the solubility and dissolution of Temsavir. Temsavir is currently being investigated clinically through the use of the prodrug BMS-663068, and a Phase III study of BMS-663068 in HIV-1-infected treatment-experienced subjects is ongoing (NCT02362503).

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
2.26 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
PubMed

PubMed

TitleDatePubMed
Patents

Sample Use Guides

In Vivo Use Guide
Phase 1: BMS-663068 (a prodrug of temsavir) 600 mg tablets orally twice daily for 8 days Phase 2: BMS-663068 (a prodrug of temsavir) 600 mg tablets orally twice daily for 48 weeks or longer
Route of Administration: Oral
In Vitro Use Guide
Temsavir (BMS-626529) inhibits HIV-1 gp120 with IC50 values of 2.26 nM, 0.34 nM and 1.3 nM for HIV-1 subtype A, B, and C envelope, respectively.
Substance Class Chemical
Created
by admin
on Mon Oct 21 22:59:13 UTC 2019
Edited
by admin
on Mon Oct 21 22:59:13 UTC 2019
Record UNII
4B6J53W8N3
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TEMSAVIR
INN   USAN   WHO-DD  
INN   USAN  
Official Name English
1,2-ETHANEDIONE, 1-(4-BENZOYL-1-PIPERAZINYL)-2-(4-METHOXY-7-(3-METHYL-1H-1,2,4-TRIAZOL-1-YL)-1H-PYRROLO(2,3-C)PYRIDIN-3-YL)-
Systematic Name English
TEMSAVIR [INN]
Common Name English
TEMSAVIR [USAN]
Common Name English
BMS-626529
Code English
PIPERAZINE, 1-BENZOYL-4-((4-METHOXY-7-(3-METHYL-1H-1,2,4-TRIAZOL-1-YL)-1H-PYRROLO(2,3-C)PYRIDIN-3-YL)OXOACETYL)-
Systematic Name English
TEMSAVIR [WHO-DD]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C1660
Created by admin on Mon Oct 21 22:59:13 UTC 2019 , Edited by admin on Mon Oct 21 22:59:13 UTC 2019
Code System Code Type Description
ChEMBL
CHEMBL3301620
Created by admin on Mon Oct 21 22:59:13 UTC 2019 , Edited by admin on Mon Oct 21 22:59:13 UTC 2019
PRIMARY
CAS
701213-36-7
Created by admin on Mon Oct 21 22:59:13 UTC 2019 , Edited by admin on Mon Oct 21 22:59:13 UTC 2019
PRIMARY
EPA CompTox
701213-36-7
Created by admin on Mon Oct 21 22:59:13 UTC 2019 , Edited by admin on Mon Oct 21 22:59:13 UTC 2019
PRIMARY
PUBCHEM
11317439
Created by admin on Mon Oct 21 22:59:13 UTC 2019 , Edited by admin on Mon Oct 21 22:59:13 UTC 2019
PRIMARY
NCI_THESAURUS
C152553
Created by admin on Mon Oct 21 22:59:13 UTC 2019 , Edited by admin on Mon Oct 21 22:59:13 UTC 2019
PRIMARY
INN
9941
Created by admin on Mon Oct 21 22:59:13 UTC 2019 , Edited by admin on Mon Oct 21 22:59:13 UTC 2019
PRIMARY
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PRODRUG -> METABOLITE ACTIVE
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ACTIVE MOIETY