Aplaviroc

Aplaviroc (INN, codenamed AK602 and GSK-873140) is a CCR5 entry inhibitor that belongs to a class of 2,5-diketopiperazines^[1] developed for the treatment of HIV infection.^[2][3] It was developed by GlaxoSmithKline.

Routes of
administrationOral

ATC code

• none

Legal status

• Development terminated

CAS Number

• 461443-59-4 ^Y
• HCl: 461023-63-2 ^Y

Quick facts Clinical data, Routes ofadministration ...

Aplaviroc

Clinical data
Routes of administration	Oral
ATC code	none
Legal status
Legal status	Development terminated
Identifiers
IUPAC name 4-(4-{[(3R)-1-butyl-3-[(R)-cyclohexylhydroxymethyl]-2,5-dioxo- 1,4,9-triazaspiro[5.5]undecan-9-yl]methyl}phenoxy)benzoic acid
CAS Number	461443-59-4 Y HCl: 461023-63-2 Y
PubChem CID	3001322
IUPHAR/BPS	805
ChemSpider	2272720 Y
UNII	98B425P30V HCl: 04D148Z3VR Y
KEGG	D06557 Y
ChEMBL	ChEMBL1255794
CompTox Dashboard (EPA)	DTXSID6047317
Chemical and physical data
Formula	C33H43N3O6
Molar mass	577.722 g·mol−1
3D model (JSmol)	Interactive image
SMILES CCCCN1C(=O)[C@H](NC(=O)C12CCN(CC2)CC3=CC=C(C=C3)OC4=CC=C(C=C4)C(=O)O)[C@@H](C5CCCCC5)O
InChI InChI=1S/C33H43N3O6/c1-2-3-19-36-30(38)28(29(37)24-7-5-4-6-8-24)34-32(41)33(36)17-20-35(21-18-33)22-23-9-13-26(14-10-23)42-27-15-11-25(12-16-27)31(39)40/h9-16,24,28-29,37H,2-8,17-22H2,1H3,(H,34,41)(H,39,40)/t28-,29-/m1/s1 Y Key:GWNOTCOIYUNTQP-FQLXRVMXSA-N Y
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In October 2005, all studies of aplaviroc were discontinued due to liver toxicity concerns.^[4][5] Some authors have claimed that evidence of poor efficacy may have contributed to termination of the drug's development;^[6] the ASCENT study, one of the discontinued trials, showed aplaviroc to be under-effective in many patients even at high concentrations.^[7]