NAV

Aplaviroc

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Generic Name
Aplaviroc
DrugBank Accession Number
DB06497
Background

A spiro-diketo-piperazine; a potent noncompetitive allosteric antagonist of the CCR5 receptor with concomitantly potent antiviral effects for HIV-1.

Type
Small Molecule
Groups
Investigational
Structure
3D
Similar Structures
Weight
Average: 577.722
Monoisotopic: 577.315186117
Chemical Formula
C33H43N3O6
Synonyms
  • Aplaviroc
External IDs
  • AK 602
  • AK-602
  • GW 873140
  • GW-873140
  • GW873140
  • ONO-4128
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Pharmacology

Indication

Investigated for use/treatment in HIV infection.

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action

GW873140 is a novel CCR5 receptor antagonist that binds specifically to human CCR5. It binds to human CCR5 with a unique profile as evidenced by the selective inhibition of monoclonal antibody binding. One of the many ways in which CCR5 inhibitors differ from the currently available classes of HIV drugs is that they bind to the host (CCR5 receptor), the cell, target rather than to the viral enzymes in cells like the CD4 cell.

TargetActionsOrganism
UC-C chemokine receptor type 5
antagonist
Humans
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Products

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Product Ingredients
IngredientUNIICASInChI Key
Aplaviroc hydrochloride04D148Z3VR461023-63-2QNNBMSGFNQRUEH-PQQSRXGVSA-N

Categories

Drug Categories
Classification
Not classified
Affected organisms
Not Available

Chemical Identifiers

UNII
98B425P30V
CAS number
461443-59-4
InChI Key
GWNOTCOIYUNTQP-FQLXRVMXSA-N
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
IUPAC Name
4-(4-{[(3R)-1-butyl-3-[(R)-cyclohexyl(hydroxy)methyl]-2,5-dioxo-1,4,9-triazaspiro[5.5]undecan-9-yl]methyl}phenoxy)benzoic acid
SMILES
[H][C@@]1(NC(=O)C2(CCN(CC3=CC=C(OC4=CC=C(C=C4)C(O)=O)C=C3)CC2)N(CCCC)C1=O)[C@H](O)C1CCCCC1

References

General References
Not Available
ChemSpider
2272720
BindingDB
50336345
ChEMBL
CHEMBL1255794
ZINC
ZINC000003990418
Wikipedia
Aplaviroc

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
3TerminatedDiagnosticHuman Immunodeficiency Virus (HIV) Infections1
3TerminatedTreatmentHuman Immunodeficiency Virus (HIV) Infections2
3TerminatedTreatmentHuman Immunodeficiency Virus Type 1 (HIV-1) Infection1
2CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections1
2TerminatedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Human Immunodeficiency Virus Type 1 (HIV-1) Infection2

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0233 mg/mLALOGPS
logP3.77ALOGPS
logP1.48Chemaxon
logS-4.4ALOGPS
pKa (Strongest Acidic)4.3Chemaxon
pKa (Strongest Basic)7.94Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count6Chemaxon
Hydrogen Donor Count3Chemaxon
Polar Surface Area119.41 Å2Chemaxon
Rotatable Bond Count10Chemaxon
Refractivity159.43 m3·mol-1Chemaxon
Polarizability63.45 Å3Chemaxon
Number of Rings5Chemaxon
Bioavailability1Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-01t9-0000090000-5231159a15de1fd825d3
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-0000090000-be94e0731b19f03d26b7
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-03fr-0000390000-b90395b2b67eb59b9acf
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-020r-0000690000-247b023d36506d5c976b
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0f92-5407590000-b89aac8f8f6ad71daa3e
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-00b9-2101890000-af1d1a76a0e34c8abe90
Chromatographic Properties
Collision Cross Sections (CCS)
Not Available

Targets

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Details1. C-C chemokine receptor type 5
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
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 r...
Gene Name
CCR5
Uniprot ID
P51681
Uniprot Name
C-C chemokine receptor type 5
Molecular Weight
40523.645 Da
References
  1. De Clercq E: Emerging anti-HIV drugs. Expert Opin Emerg Drugs. 2005 May;10(2):241-73. [Article]

Drug created at March 19, 2008 16:35 / Updated at June 28, 2022 01:37