Cenicriviroc

Category	Human immunodeficiency Virus (HIV)
CAS	497223-25-3
Description	Cenicriviroc is an inhibitor of CCR2 and CCR5 receptors, allowing it to function as an entry inhibitor which prevents the virus from entering into a human cell as an experimental drug candidate for the treatment of HIV infection.

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Product Information

Synonyms	(S,E)-8-(4-(2-Butoxyethoxy)phenyl)-1-isobutyl-N-(4-(((1-propyl-1H-imidazol-5-yl)methyl)sulfinyl)phenyl)-1,2,3,4-tetrahydrobenzo[b]azocine-5-carboxamide; TAK-652; TAK652; TAK 652; TBR-652; TBR 652; TBR652; Cenicriviroc
IUPAC Name	(5E)-8-[4-(2-butoxyethoxy)phenyl]-1-(2-methylpropyl)-N-[4-[(S)-(3-propylimidazol-4-yl)methylsulfinyl]phenyl]-3,4-dihydro-2H-1-benzazocine-5-carboxamide
Molecular Weight	696.95
Molecular Formula	C41H52N4O4S
Canonical SMILES	O=C(/C1=C/C2=CC(C3=CC=C(OCCOCCCC)C=C3)=CC=C2N(CC(C)C)CCC1)NC4=CC=C([S@](CC5=CN=CN5CCC)=O)C=C4
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
InChIKey	PNDKCRDVVKJPKG-WHERJAGFSA-N
Boiling Point	913.5±65.0 °C at 760 mmHg
Flash Point	506.3±34.3 °C
Purity	≥98%
Density	1.2±0.1 g/cm3
Solubility	Soluble in DMSO
Appearance	Solid powder
Application	CCR2 receptor antagonists; CCR5 receptor antagonists
Shelf Life	As supplied, 2 years from the QC date provided on the Certificate of Analysis, when stored properly.
Storage	Store at -20 °C
Animal Admin	Assign male C57BL/6 mice (n=44; 8-10 weeks of age) on days 1-5 received treatment by oral gavage (PO) in the following groups: non-disease control, vehicle-controlled twice daily (BID), Cenicriviroc 5 mg / kg / day (Cenicriviroc5) BID, Cenicriviroc 20 mg / kg / day (Cenicriviroc20) BID, Cenicriviroc 100 mg / kg / Day (Cenicriviroc100 BID, Cenicriviroc20 QD) and positive control dexamethasone (a corticosteroid known to reduce inflammation in various animal models) 1 mg/kg QD. Evaluate differential cell counts in peritoneal lavage samples using multiple classes of software and analysis software designed for mouse peritoneal fluid. A blood sample of a 0.3 mL aliquot was processed into plasma for PK analysis.
Complexity	1060
Exact Mass	696.37092733
Index Of Refraction	1.603
In Vitro	Cenicriviroc prevents the entry of human immunodeficiency virus type 1 (HIV-1) into cells. Regarding the 4 R5 HIV-2 clinical isolates tested, the effective concentrations for cenicriviroc 50% EC50 were 0.03, 0.33, 0.45 and 0.98 nM. Bidirectional tropical and X4-tropic HIV-2 strains are resistant to cenicriviroc with EC50>1000 nM and MPIs of 33% and 4%, respectively.
In Vivo	Cenicriviroc (≥20 mg / kg / day) significantly reduces the recruitment of monocytes / macrophages in vivo. At these doses, cenicriviroc showed anti-fibrotic effects, significant reduction in collagen deposition, collagen type 1 protein and mRNA expression in three animal models of fibrosis. In the NASH model, cenicriviroc significantly reduced nonalcoholic fatty liver disease activity scores. Cenicriviroc treatment has no significant effect on body or liver/kidney weight.
Target	CCR5:0.29 nM (IC50) CCR2:5.9 nM (IC50) R5 HIV-1:0.024-0.08 nM (IC50, in PBMCs) R5 HIV-2:0.03-0.98 nM (IC50, in PBMCs)
Vapor Pressure	0.0±0.3 mmHg at 25°C
XLogP3-AA	7.5