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Details

Stereochemistry ABSOLUTE
Molecular Formula C41H52N4O4S
Molecular Weight 696.9436
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CENICRIVIROC

SMILES

CCCCOCCOc1ccc(cc1)-c2ccc3c(c2)/C(/[H])=C(\CCCN3CC(C)C)/C(=O)Nc4ccc(cc4)[S@@](=O)Cc5cncn5CCC

InChI

InChIKey=PNDKCRDVVKJPKG-WHERJAGFSA-N
InChI=1S/C41H52N4O4S/c1-5-7-22-48-23-24-49-38-15-10-32(11-16-38)33-12-19-40-35(25-33)26-34(9-8-21-44(40)28-31(3)4)41(46)43-36-13-17-39(18-14-36)50(47)29-37-27-42-30-45(37)20-6-2/h10-19,25-27,30-31H,5-9,20-24,28-29H2,1-4H3,(H,43,46)/b34-26+/t50-/m0/s1

HIDE SMILES / InChI

Molecular Formula C41H52N4O4S
Molecular Weight 696.9436
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Cenicriviroc (also referred to as TBR-652 and TAK-652) is an orally active, potent inhibitor of ligand binding to C-C chemokine receptor type 2 (CCR2) and C-C chemokine receptor type 5 (CCR5). Cenicriviroc does not inhibit ligand binding to CCR1 (an alternative target of CCR5 ligands). The mean half-life in healthy volunteers is 35 to 40 hours, which allows daily dosing of the drug. Due to its CCR5 blocking activity, Cenicriviroc has initially been tested as a drug against CCR5-tropic HIV infection. In a double-blind placebo-controlled trial involving 54 HIV infected participants, Cenicriviroc monotherapy at different doses (25, 50, 75, 100, or 150 mg) led to a dose-dependent reduction in HIV-1 RNA levels and concomitant increases in circulating levels of the CCR2 ligand monocyte chemoattractant protein 1 (MCP-1, or CCL2), suggesting potent CCR2 and CCR5 inhibition in vivo. According to clinical trials, Cenicriviroc is a very safe drug with a wide therapeutic range and fairly low pharmacokinetic variability. In animal models of liver diseases, Cenicriviroc potently inhibits macrophage accumulation in the liver and ameliorates fibrosis. In a phase 2b clinical trial on 289 patients with NASH and fibrosis, Cenicriviroc consistently demonstrated liver fibrosis improvement after 1 year of therapy and had an excellent safety profile.

Approval Year

PubMed

PubMed

TitleDatePubMed
Stereoselective synthesis of [L-Arg-L/D-3-(2-naphthyl)alanine]-type (E)-alkene dipeptide isosteres and its application to the synthesis and biological evaluation of pseudopeptide analogues of the CXCR4 antagonist FC131.
2005 Jan 27
TAK-652 inhibits CCR5-mediated human immunodeficiency virus type 1 infection in vitro and has favorable pharmacokinetics in humans.
2005 Nov
Highly potent and orally active CCR5 antagonists as anti-HIV-1 agents: synthesis and biological activities of 1-benzazocine derivatives containing a sulfoxide moiety.
2006 Mar 23
Isolation and characterization of human immunodeficiency virus type 1 resistant to the small-molecule CCR5 antagonist TAK-652.
2007 Feb
The relative activity of "function sparing" HIV-1 entry inhibitors on viral entry and CCR5 internalization: is allosteric functional selectivity a valuable therapeutic property?
2009 Mar
Novel 4,4-disubstituted piperidine-based C-C chemokine receptor-5 inhibitors with high potency against human immunodeficiency virus-1 and an improved human ether-a-go-go related gene (hERG) profile.
2011 Jun 9
Patents

Sample Use Guides

150 mg/day cenicriviroc
Route of Administration: Oral
Substance Class Chemical
Created
by admin
on Sat Jun 26 05:41:27 UTC 2021
Edited
by admin
on Sat Jun 26 05:41:27 UTC 2021
Record UNII
15C116UA4Y
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CENICRIVIROC
INN   USAN   WHO-DD  
INN   USAN  
Official Name English
1-BENZAZOCINE-5-CARBOXAMIDE, 8-(4-(2-BUTOXYETHOXY)PHENYL)-1,2,3,4-TETRAHYDRO-1-(2- METHYLPROPYL)-N-(4-((S)-((1-PROPYL-1H-IMIDAZOL-5-YL)METHYL)SULFINYL)PHENYL)-
Common Name English
CENICRIVIROC [INN]
Common Name English
(-)-8-(4-(2-BUTOXYETHOXY)PHENYL)-1-ISOBUTYL-N-(4-(((1-PROPYL-1H-IMIDAZOL-5-YL)METHYL)SULFINYL)PHENYL)-1,2,3,4-TETRAHYDRO-1-BENZAZOCINE-5-CARBOXAMIDE
Systematic Name English
(S)-8-(4-(2-BUTOXYETHOXY)PHENYL)-1-(2-METHYLPROPYL)-N-(4-(((1-PROPYL-1H-IMIDAZOL-5- YL)METHYL)SULFINYL)PHENYL)-1,2,3,4-TETRAHYDRO-1-BENZAZOCINE-5-CARBOXAMIDE
Systematic Name English
CENICRIVIROC [USAN]
Common Name English
CENICRIVIROC [WHO-DD]
Common Name English
8-(4-(2-(BUTOXY)ETHOXY)PHENYL)-1-(2-METHYLPROPYL)-N-(4-((S)-((1-PROPYL-1H-IMIDAZOL-5-YL)METHYL)SULFINYL)PHENYL)-1,2,3,4-TETRAHYDRO-1-BENZAZOCINE-5-CARBOXAMIDE
Systematic Name English
Code System Code Type Description
NCI_THESAURUS
C166464
Created by admin on Sat Jun 26 05:41:27 UTC 2021 , Edited by admin on Sat Jun 26 05:41:27 UTC 2021
PRIMARY
ChEMBL
CHEMBL2110727
Created by admin on Sat Jun 26 05:41:27 UTC 2021 , Edited by admin on Sat Jun 26 05:41:27 UTC 2021
PRIMARY
FDA UNII
15C116UA4Y
Created by admin on Sat Jun 26 05:41:27 UTC 2021 , Edited by admin on Sat Jun 26 05:41:27 UTC 2021
PRIMARY
CAS
497223-25-3
Created by admin on Sat Jun 26 05:41:27 UTC 2021 , Edited by admin on Sat Jun 26 05:41:27 UTC 2021
PRIMARY
DRUG BANK
DB11758
Created by admin on Sat Jun 26 05:41:27 UTC 2021 , Edited by admin on Sat Jun 26 05:41:27 UTC 2021
PRIMARY
INN
9294
Created by admin on Sat Jun 26 05:41:27 UTC 2021 , Edited by admin on Sat Jun 26 05:41:27 UTC 2021
PRIMARY
WIKIPEDIA
CENICRIVIROC
Created by admin on Sat Jun 26 05:41:27 UTC 2021 , Edited by admin on Sat Jun 26 05:41:27 UTC 2021
PRIMARY
EVMPD
SUB180680
Created by admin on Sat Jun 26 05:41:27 UTC 2021 , Edited by admin on Sat Jun 26 05:41:27 UTC 2021
PRIMARY
PUBCHEM
11285792
Created by admin on Sat Jun 26 05:41:27 UTC 2021 , Edited by admin on Sat Jun 26 05:41:27 UTC 2021
PRIMARY
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