Maraviroc (CHEM020166)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 06:51:54 UTC
Update Date2016-11-09 01:16:08 UTC
Accession NumberCHEM020166
Identification
Common NameMaraviroc
ClassSmall Molecule
DescriptionMaraviroc (brand-named Selzentry, or Celsentri outside the U.S.) is a chemokine receptor antagonist drug developed by the drug company Pfizer that is designed to act against HIV by interfering with the interaction between HIV and CCR5. It was originally labelled as UK-427857 during development but was assigned the Maraviroc name as it entered trials. It was approved for use by the FDA in August, 2007.
Contaminant Sources
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
MaravirocumChEBI
Chemical FormulaC29H41F2N5O
Average Molecular Mass513.666 g/mol
Monoisotopic Mass513.328 g/mol
CAS Registry Number376348-65-1
IUPAC Name4,4-difluoro-N-[(1S)-3-[(1R,3S,5S)-3-[3-methyl-5-(propan-2-yl)-4H-1,2,4-triazol-4-yl]-8-azabicyclo[3.2.1]octan-8-yl]-1-phenylpropyl]cyclohexane-1-carboximidic acid
Traditional Name4,4-difluoro-N-[(1S)-3-[(1R,3S,5S)-3-(3-isopropyl-5-methyl-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]octan-8-yl]-1-phenylpropyl]cyclohexane-1-carboximidic acid
SMILES[H][C@@](CCN1[C@@]2([H])CC[C@]1([H])C[C@]([H])(C2)N1C(C)=NN=C1C(C)C)(N=C(O)C1CCC(F)(F)CC1)C1=CC=CC=C1
InChI IdentifierInChI=1S/C29H41F2N5O/c1-19(2)27-34-33-20(3)36(27)25-17-23-9-10-24(18-25)35(23)16-13-26(21-7-5-4-6-8-21)32-28(37)22-11-14-29(30,31)15-12-22/h4-8,19,22-26H,9-18H2,1-3H3,(H,32,37)/t23-,24+,25-,26-/m0/s1
InChI KeyGSNHKUDZZFZSJB-QYOOZWMWSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as tropane alkaloids. These are organic compounds containing the nitrogenous bicyclic alkaloid parent N-Methyl-8-azabicyclo[3.2.1]octane.
KingdomOrganic compounds
Super ClassAlkaloids and derivatives
ClassTropane alkaloids
Sub ClassNot Available
Direct ParentTropane alkaloids
Alternative Parents
Substituents
  • Tropane alkaloid
  • Cyclohexyl halide
  • Aralkylamine
  • Monocyclic benzene moiety
  • Piperidine
  • N-alkylpyrrolidine
  • Benzenoid
  • Azole
  • Pyrrolidine
  • 1,2,4-triazole
  • Heteroaromatic compound
  • Amino acid or derivatives
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Tertiary amine
  • Tertiary aliphatic amine
  • Organoheterocyclic compound
  • Azacycle
  • Carboxylic acid derivative
  • Amine
  • Organooxygen compound
  • Organonitrogen compound
  • Organofluoride
  • Organohalogen compound
  • Organopnictogen compound
  • Alkyl halide
  • Carbonyl group
  • Organic oxygen compound
  • Organic nitrogen compound
  • Alkyl fluoride
  • Hydrocarbon derivative
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
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 Solubility0.0088 g/LALOGPS
logP4.39ALOGPS
logP1.89ChemAxon
logS-4.8ALOGPS
pKa (Strongest Acidic)7.02ChemAxon
pKa (Strongest Basic)10.13ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area66.54 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity143.4 m³·mol⁻¹ChemAxon
Polarizability56.84 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-0213190000-b44e5e5f2076bacbb413Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-016s-2933110000-477407c0d3e6b419f2b1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kf-8910000000-da512595573097f9526dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0100190000-f25bd7e6884a727e66dfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-02n9-1931430000-cb353facc26e16d7765eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-02vl-4922000000-44363667a2a78057f322Spectrum
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 IDDB04835
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 LinkMaraviroc
Chemspider IDNot Available
ChEBI ID63608
PubChem Compound IDNot Available
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=21134404
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=21383098
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=21393136
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=21505306
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=21595497
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=21692669
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=21987241
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=22017448
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=22034870
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=22064539
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=22090117
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=22118500
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=22174038
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=22236118
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=22247337
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=24419064
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=24651825
18. https://www.ncbi.nlm.nih.gov/pubmed/?term=24652492
19. https://www.ncbi.nlm.nih.gov/pubmed/?term=25017682