Cenicriviroc

Cenicriviroc (INN,^[1] code names TAK-652, TBR-652, commonly abbreviated as CVC) is an experimental drug candidate for the treatment of HIV infection^[2] and in combination with Tropifexor for non-alcoholic steatohepatitis.^[3] It is being developed by Takeda and Tobira Therapeutics.^{[citation needed]}

Cenicriviroc

Names
Preferred IUPAC name (5E)-8-[4-(2-Butoxyethoxy)phenyl]-1-(2-methylpropyl)-N-{4-[(S)-(1-propyl-1H-imidazol-5-yl)methanesulfinyl]phenyl}-1,2,3,4-tetrahydro-1-benzazocine-5-carboxamide
Other names TAK-652; TBR-652
Identifiers
CAS Number	497223-25-3 Y 497223-28-6 (mesylate) Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:149636
ChEMBL	ChEMBL2110727 N
ChemSpider	9460783 N
IUPHAR/BPS	801
KEGG	D09878
PubChem CID	11285792 11285792
UNII	15C116UA4Y Y R96TV84T21 (mesylate) Y
CompTox Dashboard (EPA)	DTXSID80964373
InChI 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 N Key: PNDKCRDVVKJPKG-WHERJAGFSA-N N InChI=1/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 Key: PNDKCRDVVKJPKG-WHERJAGFBH
SMILES O=S(c1ccc(cc1)NC(=O)\C4=C\c3c(ccc(c2ccc(OCCOCCCC)cc2)c3)N(CCC4)CC(C)C)Cc5cncn5CCC
Properties
Chemical formula	C41H52N4O4S
Molar mass	696.95 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is YN ?) Infobox references

Cenicriviroc is an inhibitor of CCR2 and CCR5 receptors,^[4] allowing it to function as an entry inhibitor which prevents the virus from entering into a human cell. Inhibition of CCR2 may have an anti-inflammatory effect.^{[citation needed]}

A double-blind, randomized, placebo-controlled clinical study to assess the antiviral activity, safety, and tolerability of cenicriviroc was conducted in 2010. HIV-infected patients taking cenicriviroc had significant reductions in viral load, with the effect persisting up to two weeks after discontinuation of treatment.^[5] Additional Phase II clinical trials are underway.^[6][when?]

Cenicriviroc is also in two separate clinical trials for COVID-19: the ACTIV-I trial run by the National Center for Advancing Translational Sciences, where it is compared with a number of other immunomodulatory agents,^[7] and the Charité Trial of Cenicriviroc at the Charité Hospital in Berlin.^[8] As of 2 July 2021^[update], both trials are recruiting participants, and are expected to complete in September 2021.^{[citation needed]}

Phase IIb data presented at the 20th Conference on Retroviruses and Opportunistic Infections (CROI) in March 2013 showed similar viral suppression rates of 76% for patients taking 100 mg cenicriviroc, 73% with 200 mg cenicriviroc, and 71% with efavirenz. Non-response rates were higher with cenicriviroc, however, largely due to greater drop-out of patients. A new tablet formulation with lower pill burden may improve adherence. Looking at immune and inflammatory biomarkers, levels of MCP-1 increased and soluble CD14 decreased in the cenicriviroc arms.^[9]

See also

• Discovery and development of CCR5-receptor antagonists
• Maraviroc
• Vicriviroc