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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:52 UTC
Update Date2021-09-14 15:40:04 UTC
HMDB IDHMDB0015584
Secondary Accession Numbers
  • HMDB15584
Metabolite Identification
Common NameMaraviroc
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.
Structure
Data?1582753313
Synonyms
ValueSource
SelzentryHMDB
Pfizer brand OF maravirocHMDB
4,4-Difluoro-N-((1S)-3-(exo-3-(3-isopropyl-5-methyl-4H-1,2,4-triazol-4-yl)-8-azabicyclo(3.2.1)oct-8-yl)-1-phenylpropyl)cyclohexanecarboxamideHMDB
4,4-Difluoro-N-[(1S)-3-[(1R,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-carboximidateGenerator
MaravirocMeSH
Chemical FormulaC29H41F2N5O
Average Molecular Weight513.6655
Monoisotopic Molecular Weight513.327917369
IUPAC Name4,4-difluoro-N-[(1S)-3-[(1R,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-carboxamide
Traditional Nameselzentry
CAS Registry Number376348-65-1
SMILES
[H][C@]12CC[C@]([H])(CC(C1)N1C(C)=NN=C1C(C)C)N2CC[C@H](NC(=O)C1CCC(F)(F)CC1)C1=CC=CC=C1
InChI Identifier
InChI=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-HLMSNRGBSA-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 DescriptorsNot Available
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.011 g/LNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.011 g/LALOGPS
logP10(4.3) g/LALOGPS
logP10(3.63) g/LChemAxon
logS10(-4.7) g/LALOGPS
pKa (Strongest Acidic)14.5ChemAxon
pKa (Strongest Basic)9.38ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area63.05 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity142.88 m³·mol⁻¹ChemAxon
Polarizability55.59 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Maraviroc[H][C@]12CC[C@]([H])(CC(C1)N1C(C)=NN=C1C(C)C)N2CC[C@H](NC(=O)C1CCC(F)(F)CC1)C1=CC=CC=C13917.6Standard polar33892256
Maraviroc[H][C@]12CC[C@]([H])(CC(C1)N1C(C)=NN=C1C(C)C)N2CC[C@H](NC(=O)C1CCC(F)(F)CC1)C1=CC=CC=C13859.1Standard non polar33892256
Maraviroc[H][C@]12CC[C@]([H])(CC(C1)N1C(C)=NN=C1C(C)C)N2CC[C@H](NC(=O)C1CCC(F)(F)CC1)C1=CC=CC=C14096.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Maraviroc,1TMS,isomer #1CC1=NN=C(C(C)C)N1C1C[C@@H]2CC[C@H](C1)N2CC[C@@H](C1=CC=CC=C1)N(C(=O)C1CCC(F)(F)CC1)[Si](C)(C)C3651.2Semi standard non polar33892256
Maraviroc,1TMS,isomer #1CC1=NN=C(C(C)C)N1C1C[C@@H]2CC[C@H](C1)N2CC[C@@H](C1=CC=CC=C1)N(C(=O)C1CCC(F)(F)CC1)[Si](C)(C)C3654.0Standard non polar33892256
Maraviroc,1TMS,isomer #1CC1=NN=C(C(C)C)N1C1C[C@@H]2CC[C@H](C1)N2CC[C@@H](C1=CC=CC=C1)N(C(=O)C1CCC(F)(F)CC1)[Si](C)(C)C4578.5Standard polar33892256
Maraviroc,1TBDMS,isomer #1CC1=NN=C(C(C)C)N1C1C[C@@H]2CC[C@H](C1)N2CC[C@@H](C1=CC=CC=C1)N(C(=O)C1CCC(F)(F)CC1)[Si](C)(C)C(C)(C)C3860.2Semi standard non polar33892256
Maraviroc,1TBDMS,isomer #1CC1=NN=C(C(C)C)N1C1C[C@@H]2CC[C@H](C1)N2CC[C@@H](C1=CC=CC=C1)N(C(=O)C1CCC(F)(F)CC1)[Si](C)(C)C(C)(C)C3855.2Standard non polar33892256
Maraviroc,1TBDMS,isomer #1CC1=NN=C(C(C)C)N1C1C[C@@H]2CC[C@H](C1)N2CC[C@@H](C1=CC=CC=C1)N(C(=O)C1CCC(F)(F)CC1)[Si](C)(C)C(C)(C)C4626.2Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Maraviroc GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udj-5789500000-c1fbb569f8817687c0fb2017-09-01Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Maraviroc 10V, Positive-QTOFsplash10-03di-1411090000-7a0ec5b8cdb242a77d7e2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Maraviroc 20V, Positive-QTOFsplash10-004j-4932110000-8239e50aff7b5b3853482017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Maraviroc 40V, Positive-QTOFsplash10-002g-9700000000-e3fbb3c26ff2f159ba122017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Maraviroc 10V, Negative-QTOFsplash10-03di-0100090000-0e449cf10d4204b39ea52017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Maraviroc 20V, Negative-QTOFsplash10-0459-1932530000-4b2b3bf87eab8b4ea67c2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Maraviroc 40V, Negative-QTOFsplash10-016r-3922000000-8e4bd2a074ad53969a062017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Maraviroc 10V, Positive-QTOFsplash10-03di-0000090000-396f6c6cc48f4b58c5802021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Maraviroc 20V, Positive-QTOFsplash10-03di-0032290000-6567eec1e19f082e1b002021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Maraviroc 40V, Positive-QTOFsplash10-01r2-1900110000-60c11a36c4f938f71cf92021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Maraviroc 10V, Negative-QTOFsplash10-03di-0301090000-42af13f3f4888f175f962021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Maraviroc 20V, Negative-QTOFsplash10-03k9-3830590000-f63b8373e1a88dacc74d2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Maraviroc 40V, Negative-QTOFsplash10-01xx-4840920000-a408d897f59b74eddc6b2021-10-11Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB04835 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB04835 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID2273675
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMaraviroc
METLIN IDNot Available
PubChem Compound3002977
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular weight:
57255.585
References
  1. Abel S, Back DJ, Vourvahis M: Maraviroc: pharmacokinetics and drug interactions. Antivir Ther. 2009;14(5):607-18. [PubMed:19704163 ]
  2. Abel S, Jenkins TM, Whitlock LA, Ridgway CE, Muirhead GJ: Effects of CYP3A4 inducers with and without CYP3A4 inhibitors on the pharmacokinetics of maraviroc in healthy volunteers. Br J Clin Pharmacol. 2008 Apr;65 Suppl 1:38-46. doi: 10.1111/j.1365-2125.2008.03134.x. [PubMed:18333864 ]
  3. Mannu J, Jenardhanan P, Mathur PP: A computational study of CYP3A4 mediated drug interaction profiles for anti-HIV drugs. J Mol Model. 2011 Aug;17(8):1847-54. doi: 10.1007/s00894-010-0890-6. Epub 2010 Nov 16. [PubMed:21080015 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
Receptor for a number of inflammatory CC-chemokines including MIP-1-alpha, MIP-1-beta and RANTES and subsequently transduces a signal by increasing the intracellular calcium ion level. May play a role in the control of granulocytic lineage proliferation or differentiation. Acts as a coreceptor (CD4 being the primary receptor) for HIV-1 R5 isolates
Gene Name:
CCR5
Uniprot ID:
P51681
Molecular weight:
40523.6
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
  4. Levy JA: HIV pathogenesis: 25 years of progress and persistent challenges. AIDS. 2009 Jan 14;23(2):147-60. doi: 10.1097/QAD.0b013e3283217f9f. [PubMed:19098484 ]
  5. Agrawal-Gamse C, Lee FH, Haggarty B, Jordan AP, Yi Y, Lee B, Collman RG, Hoxie JA, Doms RW, Laakso MM: Adaptive mutations in a human immunodeficiency virus type 1 envelope protein with a truncated V3 loop restore function by improving interactions with CD4. J Virol. 2009 Nov;83(21):11005-15. doi: 10.1128/JVI.01238-09. Epub 2009 Aug 19. [PubMed:19692476 ]
  6. Napier C, Sale H, Mosley M, Rickett G, Dorr P, Mansfield R, Holbrook M: Molecular cloning and radioligand binding characterization of the chemokine receptor CCR5 from rhesus macaque and human. Biochem Pharmacol. 2005 Dec 19;71(1-2):163-72. Epub 2005 Nov 18. [PubMed:16298345 ]