AG-001859

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NCATS

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C27H33N3O5S
Molecular Weight	511.633
Optical Activity	UNSPECIFIED
Defined Stereocenters	3 / 3
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure of AG-001859

Structure Search

SMILES

[H][C@@]1(N(CSC1(C)C)C(=O)[C@@H](O)[C@H](CC2=CC=CC=C2)NC(=O)C3=C(C)C(O)=CC=C3)C(=O)NCC=C

InChI

InChIKey=LXRNKYYBEZMYNM-ACIOBRDBSA-N

InChI=1S/C27H33N3O5S/c1-5-14-28-25(34)23-27(3,4)36-16-30(23)26(35)22(32)20(15-18-10-7-6-8-11-18)29-24(33)19-12-9-13-21(31)17(19)2/h5-13,20,22-23,31-32H,1,14-16H2,2-4H3,(H,28,34)(H,29,33)/t20-,22-,23+/m0/s1

HIDE SMILES / InChI

Molecular Formula	C27H33N3O5S
Molecular Weight	511.633
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	3 / 3
E/Z Centers	0
Optical Activity	UNSPECIFIED

Approval Year

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:38:07 UTC 2023` Edited by `admin` on `Fri Dec 15 15:38:07 UTC 2023`
Record UNII	USI577N9VE
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

AG-001859

Code

English

(4R)-3-((2S,3S)-2-HYDROXY-3-((3-HYDROXY-2-METHYLBENZOYL)AMINO)-1-OXO-4-PHENYLBUTYL)-5,5-DIMETHYL-N-2-PROPENYL-4-THIAZOLIDINECARBOXAMIDE

Systematic Name

English

AG-1859

Code

English

AG 1859

Code

English

AG 001859

Code

English

(4R)-3-((2S,3S)-2-HYDROXY-3-(3-HYDROXY-2-METHYLBENZOYLAMINO)-4-PHENYL-BUTYRYL)-5,5 DIMETHYL-THIAZOLIDINE-4-CARBOXYLIC ACID ALLYLAMIDE

Systematic Name

English

Code System Code Type Description

SMS_ID

300000042363

Created by admin on Fri Dec 15 15:38:07 UTC 2023 , Edited by admin on Fri Dec 15 15:38:07 UTC 2023

PRIMARY

FDA UNII

USI577N9VE

Created by admin on Fri Dec 15 15:38:07 UTC 2023 , Edited by admin on Fri Dec 15 15:38:07 UTC 2023

PRIMARY

CAS

478410-84-3

Created by admin on Fri Dec 15 15:38:07 UTC 2023 , Edited by admin on Fri Dec 15 15:38:07 UTC 2023

PRIMARY

EPA CompTox

DTXSID90460038

Created by admin on Fri Dec 15 15:38:07 UTC 2023 , Edited by admin on Fri Dec 15 15:38:07 UTC 2023

PRIMARY

PUBCHEM

11249242

Created by admin on Fri Dec 15 15:38:07 UTC 2023 , Edited by admin on Fri Dec 15 15:38:07 UTC 2023

PRIMARY

Related Record Type Details


					USI577N9VE

AG-001859

ACTIVE MOIETY

Comments:

Class: Antiretroviral; Mechanism of Action: Peptide hydrolase inhibitor; Highest Development Phase: Discontinued for HIV infections; Most Recent Events: 11 Mar 2005 Data presented at the 12th Conference on Retroviruses and Opportunistic Infections (CROI-2005) have been added to the Viral Infections antimicrobial activity section, 06 Jan 2005 Phase-II clinical trials in HIV infections treatment in USA (unspecified route)


					USI577N9VE

AG-001859

ACTIVE MOIETY


					USI577N9VE

AG-001859

ACTIVE MOIETY

Comments:

Hammond reports AG-001859 is a potent, tight binding inhibitor of both wild-type HIV protease and an I84V/L90M mutant HIV protease, exhibiting a Ki of <0.1 nM against both enzymes. In cell-based assays, AG-001859 demonstrated potent antiviral activity against several strains of wild-type HIV, including laboratory adapted and primary isolates, with EC50 values ranging from 14 to 60 nM. The median IC50 (amount of drug to suppress replication) for AG-001859 against the 80% of the viruses was 75 nM, but it was higher for the other drugs: 278 Nm for nelfinavir, 119 nM for Kaletra, 92 nM for saquinavir, 130 nM for amprenavir, and 323 nM for indinavir.