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Identification
NameMaraviroc
Accession NumberDB04835
TypeSmall Molecule
GroupsApproved, Investigational
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
Thumb
SynonymsNot Available
External IDs Not Available
Product Ingredients Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
CelsentriTablet, film coated300 mgOralViiv Healthcare Ulc2007-09-18Not applicableEu
CelsentriTablet, film coated150 mgOralViiv Healthcare Ulc2007-09-18Not applicableEu
CelsentriTablet, film coated300 mgOralViiv Healthcare Ulc2007-09-18Not applicableEu
CelsentriTablet, film coated150 mgOralViiv Healthcare Ulc2007-09-18Not applicableEu
CelsentriTablet, film coated300 mgOralViiv Healthcare Ulc2007-09-18Not applicableEu
CelsentriTablet150 mgOralViiv Healthcare Ulc2007-09-26Not applicableCanada
CelsentriTablet, film coated150 mgOralViiv Healthcare Ulc2007-09-18Not applicableEu
CelsentriTablet, film coated300 mgOralViiv Healthcare Ulc2007-09-18Not applicableEu
CelsentriTablet300 mgOralViiv Healthcare Ulc2007-09-26Not applicableCanada
CelsentriTablet, film coated300 mgOralViiv Healthcare Ulc2007-09-18Not applicableEu
CelsentriTablet, film coated150 mgOralViiv Healthcare Ulc2007-09-18Not applicableEu
CelsentriTablet, film coated150 mgOralViiv Healthcare Ulc2007-09-18Not applicableEu
SelzentryTablet, film coated300 mg/1OralA S Medication Solutions2011-05-16Not applicableUs
SelzentryTablet, film coated150 mg/1OralRemedy Repack2013-02-182016-10-13Us
SelzentryTablet, film coated300 mg/1OralA S Medication Solutions2011-05-16Not applicableUs
SelzentryTablet, film coated300 mg/1OralPhysicians Total Care, Inc.2007-12-19Not applicableUs
SelzentryTablet, film coated25 mg/1OralViiv Healthcare Ulc2016-11-04Not applicableUs
SelzentryTablet, film coated75 mg/1OralViiv Healthcare Ulc2016-11-04Not applicableUs
SelzentryTablet, film coated150 mg/1OralViiv Healthcare Ulc2011-05-16Not applicableUs
SelzentrySolution20 mg/mLOralViiv Healthcare Ulc2016-11-04Not applicableUs
SelzentryTablet, film coated150 mg/1OralPfizer Laboratories Div Pfizer Inc.2007-08-06Not applicableUs
SelzentryTablet, film coated300 mg/1OralViiv Healthcare Ulc2011-05-16Not applicableUs
SelzentryTablet, film coated300 mg/1OralPfizer Laboratories Div Pfizer Inc.2007-08-06Not applicableUs
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
Categories
UNIIMD6P741W8A
CAS number376348-65-1
WeightAverage: 513.6655
Monoisotopic: 513.327917369
Chemical FormulaC29H41F2N5O
InChI KeyGSNHKUDZZFZSJB-QYOOZWMWSA-N
InChI
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
IUPAC Name
4,4-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
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
Pharmacology
IndicationFor treatment-experienced adult patients infected with only CCR5-tropic HIV-1 detectable, who have evidence of viral replication and HIV-1 strains resistant to multiple antiretroviral agents.
Structured Indications
PharmacodynamicsMaraviroc 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.
Mechanism of actionMaraviroc is an entry inhibitor and works by blocking HIV from entering human cells. Specifically maraviroc is a selective, slowly reversible, small molecule antagonist of the interaction between human CCR5 and HIV-1 gp120. Maraviroc selectively binds to the human chemokine receptor CCR5 present on the membrane of CD4 cells (T-cells), preventing the interaction of HIV-1 gp120 and CCR5 necessary for CCR5-tropic HIV-1 to enter cells.
TargetKindPharmacological actionActionsOrganismUniProt ID
C-C chemokine receptor type 5Proteinyes
antagonist
HumanP51681 details
Related Articles
AbsorptionThe absolute oral bioavailability of a 100 mg dose is 23% and is predicted to be 33% at 300 mg. Coadministration of a 300mg tablet with a high fat breakfast reduced maraviroc Cmax and AUC by 33% in healthy volunteers.
Volume of distribution
  • 194 L
Protein bindingApproximately 76% bound to human plasma proteins, with moderate affinity for albumin and alpha-1 acid glycoprotein.
Metabolism

In vitro studies indicate that CYP3A is the major enzyme responsible for maraviroc metabolism.

Route of eliminationNot Available
Half life14-18 hours
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Human Immunodeficiency Virus
PathwaysNot Available
Pharmacogenomic Effects/ADRs Not Available
Interactions
Drug Interactions
DrugInteractionDrug group
AmiodaroneThe serum concentration of Maraviroc can be increased when it is combined with Amiodarone.Approved, Investigational
AprepitantThe serum concentration of Maraviroc can be increased when it is combined with Aprepitant.Approved, Investigational
AtazanavirThe serum concentration of Maraviroc can be increased when it is combined with Atazanavir.Approved, Investigational
AtomoxetineThe metabolism of Maraviroc can be decreased when combined with Atomoxetine.Approved
BexaroteneThe serum concentration of Maraviroc can be decreased when it is combined with Bexarotene.Approved, Investigational
BoceprevirThe serum concentration of Maraviroc can be increased when it is combined with Boceprevir.Approved
BortezomibThe metabolism of Maraviroc can be decreased when combined with Bortezomib.Approved, Investigational
BosentanThe serum concentration of Maraviroc can be decreased when it is combined with Bosentan.Approved, Investigational
CarbamazepineThe serum concentration of Maraviroc can be decreased when it is combined with Carbamazepine.Approved, Investigational
CeritinibThe serum concentration of Maraviroc can be increased when it is combined with Ceritinib.Approved
ClarithromycinThe serum concentration of Maraviroc can be increased when it is combined with Clarithromycin.Approved
ClemastineThe metabolism of Maraviroc can be decreased when combined with Clemastine.Approved
ClotrimazoleThe metabolism of Maraviroc can be decreased when combined with Clotrimazole.Approved, Vet Approved
CobicistatThe serum concentration of Maraviroc can be increased when it is combined with Cobicistat.Approved
ConivaptanThe serum concentration of Maraviroc can be increased when it is combined with Conivaptan.Approved, Investigational
CrizotinibThe metabolism of Maraviroc can be decreased when combined with Crizotinib.Approved
CyclosporineThe metabolism of Maraviroc can be decreased when combined with Cyclosporine.Approved, Investigational, Vet Approved
DabrafenibThe serum concentration of Maraviroc can be decreased when it is combined with Dabrafenib.Approved
DarunavirThe serum concentration of Maraviroc can be increased when it is combined with Darunavir.Approved
DasatinibThe serum concentration of Maraviroc can be increased when it is combined with Dasatinib.Approved, Investigational
DeferasiroxThe serum concentration of Maraviroc can be decreased when it is combined with Deferasirox.Approved, Investigational
DelavirdineThe metabolism of Maraviroc can be decreased when combined with Delavirdine.Approved
DexamethasoneThe serum concentration of Maraviroc can be decreased when it is combined with Dexamethasone.Approved, Investigational, Vet Approved
DihydroergotamineThe metabolism of Maraviroc can be decreased when combined with Dihydroergotamine.Approved
DiltiazemThe metabolism of Maraviroc can be decreased when combined with Diltiazem.Approved
DoxycyclineThe metabolism of Maraviroc can be decreased when combined with Doxycycline.Approved, Investigational, Vet Approved
DronedaroneThe metabolism of Maraviroc can be decreased when combined with Dronedarone.Approved
EfavirenzThe serum concentration of Maraviroc can be decreased when it is combined with Efavirenz.Approved, Investigational
EnzalutamideThe serum concentration of Maraviroc can be decreased when it is combined with Enzalutamide.Approved
ErythromycinThe metabolism of Maraviroc can be decreased when combined with Erythromycin.Approved, Vet Approved
Eslicarbazepine acetateThe serum concentration of Maraviroc can be decreased when it is combined with Eslicarbazepine acetate.Approved
EtravirineThe serum concentration of Maraviroc can be decreased when it is combined with Etravirine.Approved
FluconazoleThe metabolism of Maraviroc can be decreased when combined with Fluconazole.Approved
FluvoxamineThe metabolism of Maraviroc can be decreased when combined with Fluvoxamine.Approved, Investigational
FosamprenavirThe metabolism of Maraviroc can be decreased when combined with Fosamprenavir.Approved
FosaprepitantThe serum concentration of Maraviroc can be increased when it is combined with Fosaprepitant.Approved
FosphenytoinThe serum concentration of Maraviroc can be decreased when it is combined with Fosphenytoin.Approved
Fusidic AcidThe serum concentration of Maraviroc can be increased when it is combined with Fusidic Acid.Approved
IdelalisibThe serum concentration of Maraviroc can be increased when it is combined with Idelalisib.Approved
ImatinibThe metabolism of Maraviroc can be decreased when combined with Imatinib.Approved
IndinavirThe serum concentration of Maraviroc can be increased when it is combined with Indinavir.Approved
IsavuconazoniumThe metabolism of Maraviroc can be decreased when combined with Isavuconazonium.Approved, Investigational
IsradipineThe metabolism of Maraviroc can be decreased when combined with Isradipine.Approved
ItraconazoleThe serum concentration of Maraviroc can be increased when it is combined with Itraconazole.Approved, Investigational
IvacaftorThe serum concentration of Maraviroc can be increased when it is combined with Ivacaftor.Approved
KetoconazoleThe serum concentration of Maraviroc can be increased when it is combined with Ketoconazole.Approved, Investigational
LopinavirThe serum concentration of Maraviroc can be increased when it is combined with Lopinavir.Approved
LovastatinThe metabolism of Maraviroc can be decreased when combined with Lovastatin.Approved, Investigational
LuliconazoleThe serum concentration of Maraviroc can be increased when it is combined with Luliconazole.Approved
LumacaftorThe serum concentration of Maraviroc can be decreased when it is combined with Lumacaftor.Approved
MifepristoneThe serum concentration of Maraviroc can be increased when it is combined with Mifepristone.Approved, Investigational
MitotaneThe serum concentration of Maraviroc can be decreased when it is combined with Mitotane.Approved
ModafinilThe serum concentration of Maraviroc can be decreased when it is combined with Modafinil.Approved, Investigational
NafcillinThe serum concentration of Maraviroc can be decreased when it is combined with Nafcillin.Approved
NefazodoneThe serum concentration of Maraviroc can be increased when it is combined with Nefazodone.Approved, Withdrawn
NelfinavirThe serum concentration of Maraviroc can be increased when it is combined with Nelfinavir.Approved
NetupitantThe serum concentration of Maraviroc can be increased when it is combined with Netupitant.Approved
NevirapineThe serum concentration of Maraviroc can be decreased when it is combined with Nevirapine.Approved
NilotinibThe metabolism of Maraviroc can be decreased when combined with Nilotinib.Approved, Investigational
OlaparibThe metabolism of Maraviroc can be decreased when combined with Olaparib.Approved
OsimertinibThe serum concentration of Maraviroc can be increased when it is combined with Osimertinib.Approved
PalbociclibThe serum concentration of Maraviroc can be increased when it is combined with Palbociclib.Approved
PentobarbitalThe serum concentration of Maraviroc can be decreased when it is combined with Pentobarbital.Approved, Vet Approved
PhenobarbitalThe serum concentration of Maraviroc can be decreased when it is combined with Phenobarbital.Approved
PhenytoinThe serum concentration of Maraviroc can be decreased when it is combined with Phenytoin.Approved, Vet Approved
PosaconazoleThe serum concentration of Maraviroc can be increased when it is combined with Posaconazole.Approved, Investigational, Vet Approved
PrimidoneThe serum concentration of Maraviroc can be decreased when it is combined with Primidone.Approved, Vet Approved
RanolazineThe metabolism of Maraviroc can be decreased when combined with Ranolazine.Approved, Investigational
RifabutinThe serum concentration of Maraviroc can be decreased when it is combined with Rifabutin.Approved
RifampicinThe serum concentration of Maraviroc can be decreased when it is combined with Rifampicin.Approved
RifapentineThe serum concentration of Maraviroc can be decreased when it is combined with Rifapentine.Approved
RitonavirThe serum concentration of Maraviroc can be increased when it is combined with Ritonavir.Approved, Investigational
SaquinavirThe serum concentration of Maraviroc can be increased when it is combined with Saquinavir.Approved, Investigational
SildenafilThe metabolism of Maraviroc can be decreased when combined with Sildenafil.Approved, Investigational
SiltuximabThe serum concentration of Maraviroc can be decreased when it is combined with Siltuximab.Approved
SimeprevirThe serum concentration of Maraviroc can be increased when it is combined with Simeprevir.Approved
St. John's WortThe serum concentration of Maraviroc can be decreased when it is combined with St. John's Wort.Nutraceutical
StiripentolThe serum concentration of Maraviroc can be increased when it is combined with Stiripentol.Approved
SulfisoxazoleThe metabolism of Maraviroc can be decreased when combined with Sulfisoxazole.Approved, Vet Approved
TelaprevirThe serum concentration of Maraviroc can be increased when it is combined with Telaprevir.Approved
TelithromycinThe serum concentration of Maraviroc can be increased when it is combined with Telithromycin.Approved
TiclopidineThe metabolism of Maraviroc can be decreased when combined with Ticlopidine.Approved
TocilizumabThe serum concentration of Maraviroc can be decreased when it is combined with Tocilizumab.Approved
VenlafaxineThe metabolism of Maraviroc can be decreased when combined with Venlafaxine.Approved
VerapamilThe metabolism of Maraviroc can be decreased when combined with Verapamil.Approved
VoriconazoleThe serum concentration of Maraviroc can be increased when it is combined with Voriconazole.Approved, Investigational
ZiprasidoneThe metabolism of Maraviroc can be decreased when combined with Ziprasidone.Approved
Food InteractionsNot Available
References
Synthesis Reference

DrugSyn.org

US020013337
General ReferencesNot Available
External Links
ATC CodesJ05AX09
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelDownload (241 KB)
MSDSNot Available
Clinical Trials
Clinical Trials
PhaseStatusPurposeConditionsCount
0TerminatedTreatmentHIV-1 Infections1
1CompletedNot AvailableHIV Disease1
1CompletedNot AvailableHIV-1 Infections / Human Immunodeficiency Virus (HIV) Infections / Mycobacterium avium complex infection1
1CompletedNot AvailableHuman Immunodeficiency Virus (HIV) Infections1
1CompletedNot AvailableInfection, Human Immunodeficiency Virus I1
1CompletedBasic ScienceCytochrome P450 CYP3A5 Enzyme Polymorphism / Healthy Volunteers / Pharmacokinetics of Maraviroc1
1CompletedBasic ScienceHIV/AIDS1
1CompletedBasic ScienceHealthy Volunteers1
1CompletedHealth Services ResearchHIV Disease1
1CompletedPreventionHIV Disease1
1CompletedPreventionHealthy Adult Females1
1CompletedTreatmentHIV/AIDS1
1CompletedTreatmentHealthy Volunteers3
1CompletedTreatmentHealthy Volunteers / Human Immunodeficiency Virus (HIV) Infections1
1CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections3
1CompletedTreatmentHypertriglyceridemias1
1Not Yet RecruitingPreventionHuman Immunodeficiency Virus (HIV) Infections1
1TerminatedScreeningHuman Immunodeficiency Virus (HIV) Infections1
1TerminatedTreatmentHealthy Volunteers1
1Unknown StatusBasic ScienceHealthy Volunteers1
1WithdrawnPreventionHuman Immunodeficiency Virus (HIV) Infections1
1, 2Active Not RecruitingTreatmentGraft Versus Host Disease (GVHD) / Hematopoietic Stem Cell Transplantation (HSCT)1
1, 2CompletedTreatmentAcute HIV Infection1
1, 2RecruitingPreventionDiagnoses That Require Stem Cell Transplant / Graft Versus Host Disease (GVHD)1
2Active Not RecruitingPreventionChronic Lymphocytic Leukaemia (CLL) / Chronic Myelogenous Leukemia (CML) / Follicular Lymphoma (FL) / Leukaemia, Acute / Lymphoma, B-Cell / Lymphoma, Hodgkins / Lymphoma, Large B-Cell, Diffuse / Myelodysplasia / Small Lymphocytic Lymphoma (SLL)1
2Active Not RecruitingTreatmentHIV Disease1
2Active Not RecruitingTreatmentHematologic Malignancy Requiring Allogeneic Stem-cell Transplantation1
2Active Not RecruitingTreatmentHuman Immunodeficiency Virus (HIV)1
2CompletedNot AvailableHealthy Volunteers1
2CompletedBasic ScienceHuman Immunodeficiency Virus Type 1 (HIV-1)1
2CompletedPreventionHuman Immunodeficiency Virus (HIV) Infections1
2CompletedTreatmentHIV Disease1
2CompletedTreatmentHIV-1 Infections1
2CompletedTreatmentHIV-1 Infections / Human Immunodeficiency Virus (HIV) Infections1
2CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections3
2CompletedTreatmentHuman Immunodeficiency Virus Type 1 (HIV-1)1
2RecruitingPreventionGraft Versus Host Disease (GVHD) / Hematopoietic Stem Cell Transplantation (HSCT)1
2RecruitingTreatmentHuman Immunodeficiency Virus (HIV) Infections1
2TerminatedTreatmentHuman Immunodeficiency Virus (HIV) / Lipohypertrophy1
2TerminatedTreatmentRheumatoid Arthritis1
2Unknown StatusTreatmentHuman Immunodeficiency Virus (HIV) Infections1
2, 3CompletedTreatmentAcute HIV Infection1
2, 3CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections4
2, 3RecruitingTreatmentAIDS Dementia Complex1
3CompletedTreatmentAcquired Immunodeficiency Syndromes / Human Immunodeficiency Virus (HIV) Infections1
3CompletedTreatmentAdvanced HIV Infection / Human Immunodeficiency Virus (HIV) Infections1
3CompletedTreatmentAids / HIV-1 Infections1
3CompletedTreatmentCardiovascular Diseases / Human Immunodeficiency Virus (HIV) Infections / Inflammatory processes1
3CompletedTreatmentHIV-1 Infections1
3CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections3
3CompletedTreatmentHuman Immunodeficiency Virus Type 1 (HIV-1)1
3No Longer AvailableNot AvailableHIV Disease1
3No Longer AvailableNot AvailableHuman Immunodeficiency Virus (HIV)1
3RecruitingTreatmentAcute HIV Infection1
3TerminatedTreatmentHuman Immunodeficiency Virus (HIV) Infections1
3TerminatedTreatmentHuman Immunodeficiency Virus Type 1 (HIV-1)1
3WithdrawnTreatmentHuman Immunodeficiency Virus Type 1 (HIV-1)1
4CompletedNot AvailableHIV Disease / Proteinuria1
4CompletedNot AvailableHealthy Volunteers1
4CompletedPreventionHuman Immunodeficiency Virus (HIV) Infections1
4CompletedTreatmentAids1
4CompletedTreatmentAids / Human Immunodeficiency Virus (HIV)1
4CompletedTreatmentHIV Associated Neurocognitive Disorders (HAND) / Human Immunodeficiency Virus (HIV)1
4CompletedTreatmentHIV Coinfection1
4CompletedTreatmentHIV Disease3
4CompletedTreatmentHIV Disease / Human Immunodeficiency Virus (HIV) Infections1
4CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections8
4Not Yet RecruitingTreatmentCCR5 / HIV Disease / HIV Reservoir / Transplant, Kidney1
4Not Yet RecruitingTreatmentHepatitis C / Human Immunodeficiency Virus (HIV)1
4RecruitingTreatmentHuman Immunodeficiency Virus (HIV) Infections1
4TerminatedTreatmentAcquired Immunodeficiency Syndromes / Human Immunodeficiency Virus (HIV) Infections1
4TerminatedTreatmentHuman Immunodeficiency Virus (HIV) Infections2
4Unknown StatusTreatmentAids / HIV-1 Adults Patients / Triple Class Failure1
4Unknown StatusTreatmentEndothelial Dysfunction1
4Unknown StatusTreatmentHIV-1 Infections1
4WithdrawnTreatmentHepatitis B / Hepatitis C, Chronic / Human Immunodeficiency Virus (HIV)1
Not AvailableActive Not RecruitingNot AvailableCCR5-tropic HIV-1 Infection1
Not AvailableActive Not RecruitingNot AvailableHuman Immunodeficiency Virus (HIV)1
Not AvailableActive Not RecruitingTreatmentChronic Infection / HIV Disease1
Not AvailableCompletedNot AvailableAids / Human Immunodeficiency Virus (HIV) Infections1
Not AvailableCompletedNot AvailableCardiovascular Diseases1
Not AvailableCompletedNot AvailableColorectal Cancers / Liver Metastases / Neoplasms Metastasis1
Not AvailableCompletedNot AvailableHIV-1 Infections1
Not AvailableCompletedNot AvailableHuman Immunodeficiency Virus (HIV) Infections1
Not AvailableCompletedNot AvailableHuman Immunodeficiency Virus Type 1 (HIV-1)1
Not AvailableCompletedBasic ScienceSarcoidosis1
Not AvailableCompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections3
Not AvailableRecruitingPreventionHIV Disease1
Not AvailableUnknown StatusPreventionHIV Disease / Human Immunodeficiency Virus (HIV) Infections / Immune Reconstitution Inflammatory Syndrome1
Not AvailableUnknown StatusTreatmentHuman Immunodeficiency Virus (HIV) Infections1
Not AvailableUnknown StatusTreatmentKaposi s Sarcoma (KS)1
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage forms
FormRouteStrength
TabletOral150 mg
TabletOral300 mg
Tablet, film coatedOral150 mg
Tablet, film coatedOral300 mg
SolutionOral20 mg/mL
Tablet, film coatedOral150 mg/1
Tablet, film coatedOral25 mg/1
Tablet, film coatedOral300 mg/1
Tablet, film coatedOral75 mg/1
Prices
Unit descriptionCostUnit
Selzentry 150 mg tablet18.36USD tablet
Selzentry 300 mg tablet18.36USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
CA2350073 No2007-04-172019-12-23Canada
CA2408909 No2006-06-272021-05-09Canada
US6586430 No1999-12-012019-12-01Us
US6667314 No2001-08-062021-08-06Us
US7368460 No2002-11-252022-11-25Us
US7576097 No2001-05-252021-05-25Us
Properties
StateSolid
Experimental PropertiesNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.00883 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count8ChemAxon
Refractivity143.4 m3·mol-1ChemAxon
Polarizability56.84 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.997
Blood Brain Barrier+0.8329
Caco-2 permeable-0.8957
P-glycoprotein substrateSubstrate0.6716
P-glycoprotein inhibitor IInhibitor0.8931
P-glycoprotein inhibitor IIInhibitor0.9431
Renal organic cation transporterNon-inhibitor0.5695
CYP450 2C9 substrateNon-substrate0.8308
CYP450 2D6 substrateNon-substrate0.7344
CYP450 3A4 substrateSubstrate0.8199
CYP450 1A2 substrateNon-inhibitor0.8616
CYP450 2C9 inhibitorInhibitor0.6028
CYP450 2D6 inhibitorNon-inhibitor0.8331
CYP450 2C19 inhibitorInhibitor0.5684
CYP450 3A4 inhibitorInhibitor0.6066
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.7814
Ames testNon AMES toxic0.63
CarcinogenicityNon-carcinogens0.706
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.7115 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9864
hERG inhibition (predictor II)Inhibitor0.8971
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as tropane alkaloids. These are organic compounds containing the nitrogenous bicyclic alkaloid parent N-Methyl-8-azabicyclo[3.2.1]octane.
KingdomChemical entities
Super ClassOrganic compounds
ClassAlkaloids and derivatives
Sub ClassTropane alkaloids
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

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
antagonist
General Function:
Virus receptor activity
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.(Microbial infection) Acts as a receptor for hu...
Gene Name:
CCR5
Uniprot ID:
P51681
Molecular Weight:
40523.645 Da
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 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Vitamin d3 25-hydroxylase 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 xenobiot...
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular Weight:
57342.67 Da
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 ]
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Drug created on September 11, 2007 19:14 / Updated on April 22, 2017 04:12