Aplaviroc hydrochloride (CHEM019486)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 06:09:52 UTC
Update Date2016-11-09 01:16:00 UTC
Accession NumberCHEM019486
Identification
Common NameAplaviroc hydrochloride
ClassSmall Molecule
DescriptionAplaviroc (INN, codenamed AK602 and GSK-873140) is a CCR5 entry inhibitor that belongs to a class of 2,5-diketopiperazines developed for the treatment of HIV infection. It was developed by GlaxoSmithKline. In October 2005, all studies of aplaviroc were discontinued due to liver toxicity concerns. Some authors have claimed that evidence of poor efficacy may have contributed to termination of the drug's development; the ASCENT study, one of the discontinued trials, showed aplaviroc to be under-effective in many patients even at high concentrations.
Contaminant Sources
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
GW873140aChEMBL
Aplaviroc HCLChEMBL
4-[4-[[(3R)-1-Butyl-3-[(R)-cyclohexyl(hydroxy)methyl]-2,5-dioxo-1,4,9-triazaspiro[5.5]undecan-9-yl]methyl]phenoxy]benzoate;hydrochlorideGenerator
Chemical FormulaC33H44ClN3O6
Average Molecular Mass614.180 g/mol
Monoisotopic Mass613.292 g/mol
CAS Registry Number461023-63-2
IUPAC Name4-(4-{[(3R)-1-butyl-3-[(R)-cyclohexyl(hydroxy)methyl]-5-hydroxy-2-oxo-1,4,9-triazaspiro[5.5]undec-4-en-9-yl]methyl}phenoxy)benzoic acid hydrochloride
Traditional Nameaplaviroc hydrochloride
SMILESCl.[H][C@@](O)(C1CCCCC1)[C@@]1([H])N=C(O)C2(CCN(CC3=CC=C(OC4=CC=C(C=C4)C(O)=O)C=C3)CC2)N(CCCC)C1=O
InChI IdentifierInChI=1S/C33H43N3O6.ClH/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);1H/t28-,29-;/m1./s1
InChI KeyQNNBMSGFNQRUEH-PQQSRXGVSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as phenylpiperazines. Phenylpiperazines are compounds containing a phenylpiperazine skeleton, which consists of a piperazine bound to a phenyl group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassDiazinanes
Sub ClassPiperazines
Direct ParentPhenylpiperazines
Alternative Parents
Substituents
  • N-arylpiperazine
  • Phenylpiperazine
  • Phenoxyacetate
  • Trifluoromethylbenzene
  • Methoxyaniline
  • Aminophenyl ether
  • Thiophenol ether
  • 2,4,5-trisubstituted 1,3-thiazole
  • Dialkylarylamine
  • Aniline or substituted anilines
  • Phenoxy compound
  • Methoxybenzene
  • Anisole
  • Phenol ether
  • Aryl thioether
  • Tertiary aliphatic/aromatic amine
  • N-alkylpiperazine
  • Alkyl aryl ether
  • Alkylarylthioether
  • Aralkylamine
  • Benzenoid
  • Monocyclic benzene moiety
  • Azole
  • Heteroaromatic compound
  • Thiazole
  • Tertiary amine
  • Tertiary aliphatic amine
  • Amino acid
  • Amino acid or derivatives
  • Sulfenyl compound
  • Azacycle
  • Thioether
  • Carboxylic acid derivative
  • Carboxylic acid
  • Ether
  • Monocarboxylic acid or derivatives
  • Alkyl fluoride
  • Organohalogen compound
  • Organofluoride
  • Organonitrogen compound
  • Organooxygen compound
  • Carbonyl group
  • Organic oxide
  • Organic nitrogen compound
  • Organopnictogen compound
  • Organosulfur compound
  • Amine
  • Alkyl halide
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.014 g/LALOGPS
logP4.27ALOGPS
logP2ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)3.99ChemAxon
pKa (Strongest Basic)8.11ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area122.9 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity159.95 m³·mol⁻¹ChemAxon
Polarizability63.58 ųChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0000009000-1d1cc377479d5d0fd47cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0000009000-1d1cc377479d5d0fd47cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-0000009000-1d1cc377479d5d0fd47cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0000009000-6823a05453bf4299643fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0000009000-6823a05453bf4299643fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03di-0000009000-6823a05453bf4299643fSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkAplaviroc
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID6918686
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available