TMC-310911

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NCATS

Investigational

Investigational

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C38H53N5O7S2
Molecular Weight	755.987
Optical Activity	UNSPECIFIED
Defined Stereocenters	5 / 5
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure of TMC-310911

Structure Search

SMILES

[H][C@]12OCC[C@@]1([H])[C@H](CO2)OC(=O)N[C@@H](CC3=CC=CC=C3)[C@H](O)CN(CC(C)C)S(=O)(=O)C4=CC=C5N=C(NC6CCN(CC6)C7CCCC7)SC5=C4

InChI

InChIKey=JQUNFHFWXCXPRK-AMMMHQJVSA-N

InChI=1S/C38H53N5O7S2/c1-25(2)22-43(23-33(44)32(20-26-8-4-3-5-9-26)41-38(45)50-34-24-49-36-30(34)16-19-48-36)52(46,47)29-12-13-31-35(21-29)51-37(40-31)39-27-14-17-42(18-15-27)28-10-6-7-11-28/h3-5,8-9,12-13,21,25,27-28,30,32-34,36,44H,6-7,10-11,14-20,22-24H2,1-2H3,(H,39,40)(H,41,45)/t30-,32-,33+,34-,36+/m0/s1

HIDE SMILES / InChI

Molecular Formula	C38H53N5O7S2
Molecular Weight	755.987
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	5 / 5
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://clinicaltrials.gov/ct2/show/NCT00838162 | https://adisinsight.springer.com/drugs/800031712

ASC-09 orTMC-310911, a HIV protease inhibitor, participated in phase II clinical for the treatment of Human Immunodeficiency Virus Type 1. However, no recent development has been reported.

Originator

Approval Year

Sample Use Guides

In Vivo Use Guide

75 mg twice daily orally (by mouth) on Days 1 to 14.

Route of Administration: Oral

Substance Class	Chemical Created by `admin` on `Sat Dec 16 10:14:55 GMT 2023` Edited by `admin` on `Sat Dec 16 10:14:55 GMT 2023`
Record UNII	0151W500HP
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

TMC-310911

Code

English

((3AS,4R,6AR)-2,3,3A,4,5,6A-HEXAHYDROFURO(2,3-B)FURAN-4-YL) N-((1S,2R)-1-BENZYL-3-((2-((1-CYCLOPENTYL-4-PIPERIDYL)AMINO)-1,3-BENZOTHIAZOL-6-YL)SULFONYL-ISOBUTYL-AMINO)-2-HYDROXY-PROPYL)CARBAMATE

Systematic Name

English

CARBAMIC ACID, N-((1S,2R)-3-(((2-((1-CYCLOPENTYL-4-PIPERIDINYL)AMINO)-6-BENZOTHIAZOLYL)SULFONYL)(2-METHYLPROPYL)AMINO)-2-HYDROXY-1-(PHENYLMETHYL)PROPYL)-, (3R,3AS,6AR)-HEXAHYDROFURO(2,3-B)FURAN-3-YL ESTER

Systematic Name

English

ASC 09 [WHO-DD]

Common Name

English

ASC-09

Code

English

ASC09

Code

English

TMC310911

Code

English

Code System Code Type Description

SMS_ID

300000021735

Created by admin on Sat Dec 16 10:14:56 GMT 2023 , Edited by admin on Sat Dec 16 10:14:56 GMT 2023

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NCI_THESAURUS

C172635

Created by admin on Sat Dec 16 10:14:56 GMT 2023 , Edited by admin on Sat Dec 16 10:14:56 GMT 2023

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FDA UNII

0151W500HP

Created by admin on Sat Dec 16 10:14:56 GMT 2023 , Edited by admin on Sat Dec 16 10:14:56 GMT 2023

PRIMARY

WIKIPEDIA

TMC-310911

Created by admin on Sat Dec 16 10:14:56 GMT 2023 , Edited by admin on Sat Dec 16 10:14:56 GMT 2023

PRIMARY

PUBCHEM

53361968

Created by admin on Sat Dec 16 10:14:56 GMT 2023 , Edited by admin on Sat Dec 16 10:14:56 GMT 2023

PRIMARY

DRUG BANK

DB15623

Created by admin on Sat Dec 16 10:14:56 GMT 2023 , Edited by admin on Sat Dec 16 10:14:56 GMT 2023

PRIMARY

EPA CompTox

DTXSID001028122

Created by admin on Sat Dec 16 10:14:56 GMT 2023 , Edited by admin on Sat Dec 16 10:14:56 GMT 2023

PRIMARY

CAS

1000287-05-7

Created by admin on Sat Dec 16 10:14:56 GMT 2023 , Edited by admin on Sat Dec 16 10:14:56 GMT 2023

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Related Record Type Details


					859A956UY8

HUMAN IMMUNODEFICIENCY VIRUS TYPE 1

TARGET ORGANISM->INHIBITOR

Amount:

Related Record Type Details


					0151W500HP

ACTIVE MOIETY

Comments:

Originator: Tibotec Pharmaceuticals; Developer: Janssen R&D Ireland; Class: Antiretroviral; Mechanism of Action: HIV protease inhibitor; New Molecular Entity: Yes; Highest Development Phase: No development reported for HIV-1 infections; Most Recent Events: 10 Aug 2015 No recent reports on development identified - Phase-II for HIV-1 infections (Monotherapy, Treatment-naive) in Germany (PO), 10 Aug 2015 No recent reports on development identified - Phase-I for HIV-1 infections (Combination therapy) in Ireland (PO), 30 Apr 2013 TMC 310911 licensed to Ascletis in Greater China, including Macau and China

Amount:


					0151W500HP

ACTIVE MOIETY

Comments:

TMC310911 is a novel human immunodeficiency virus type 1 (HIV-1) protease inhibitor (PI) structurally closely related to darunavir (DRV) but with improved virological characteristics. TMC310911 has potent activity against wild-type (WT) HIV-1 (median 50% effective concentration (EC50), 14 nM) and a wide spectrum of recombinant HIV-1 clinical isolates, including multiple-PI-resistant strains with decreased susceptibility to currently approved PIs (fold change (FC) in EC50, >10). For a panel of 2,011 recombinant clinical isolates with decreased susceptibility to at least one of the currently approved PIs, the FC in TMC310911 EC50 was 4 for 82% of isolates and 10 for 96% of isolates. In vitro resistance selection (IVRS) experiments with WT virus and TMC310911 selected for mutations R41G or R41E, but selection of resistant virus required a longer time than IVRS performed with WT virus and DRV. IVRS performed with r13025, a multiple-PI-resistant recombinant clinical isolate, and TMC310911 selected for mutations L10F, I47V, and L90M (FC in TMC310911 EC50 = 16).

Amount: