NAV

Vicriviroc

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

Identification

Generic Name
Vicriviroc
DrugBank Accession Number
DB06652
Background

Vicriviroc, also known as SCH 417690 and SCH-D, is currently in clinical trials for the management of HIV-1. This pyrimidine based drug inhibits the interaction of HIV-1 with CCR5, preventing viral entry into cells. This drug was developed by Schering-Plough.

Type
Small Molecule
Groups
Investigational
Structure
3D
Similar Structures
Weight
Average: 533.6288
Monoisotopic: 533.2977601
Chemical Formula
C28H38F3N5O2
Synonyms
  • Vicriviroc
External IDs
  • MK-4176
  • SCH 417690
  • SCH-417690
  • SCH-D
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Pharmacology

Indication

Investigated for use/treatment in HIV infection and viral infection.

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action

Vicriviroc is a once daily oral inhibitor of CCR5. It noncompetitively binds to a hydrophobic pocket between transmembrance helices by the extracellular side of CCR5. This allosteric antagonism causes a conformational change in the protein preventing binding of gp120 to CCR5. This prevents the entry of HIV into the cell.

TargetActionsOrganism
UC-C chemokine receptor type 5
antagonist
Humans
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism

Metabolised primarily by the CYP3A4 system

Hover over products below to view reaction partners

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 Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
Not Available

Interactions

Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
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.
DrugInteraction
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interactions in your software
AbametapirThe serum concentration of Vicriviroc can be increased when it is combined with Abametapir.
AbataceptThe metabolism of Vicriviroc can be increased when combined with Abatacept.
AbrocitinibThe metabolism of Abrocitinib can be decreased when combined with Vicriviroc.
AcalabrutinibThe metabolism of Vicriviroc can be decreased when combined with Acalabrutinib.
AcenocoumarolThe metabolism of Vicriviroc can be decreased when combined with Acenocoumarol.
Food Interactions
Not Available

Products

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Product Ingredients
IngredientUNIICASInChI Key
Vicriviroc Hydrochloride25SS1WQB7W541503-48-4ULGCLTGMZKAFMX-RIAYWLAYSA-N
Vicriviroc MaleateEP3QG127N9599179-03-0GXINKQQWHLIBJA-UCIBKFKQSA-N

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as trifluoromethylbenzenes. These are organofluorine compounds that contain a benzene ring substituted with one or more trifluoromethyl groups.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Trifluoromethylbenzenes
Direct Parent
Trifluoromethylbenzenes
Alternative Parents
Pyrimidinecarboxylic acids and derivatives / N-acylpiperidines / Aminopiperidines / Aralkylamines / N-alkylpiperazines / Tertiary carboxylic acid amides / Heteroaromatic compounds / Trialkylamines / Amino acids and derivatives / Azacyclic compounds
show 6 more
Substituents
1,4-diazinane / 4-aminopiperidine / Alkyl fluoride / Alkyl halide / Amine / Amino acid or derivatives / Aralkylamine / Aromatic heteromonocyclic compound / Azacycle / Carboxamide group
show 24 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
TL515DW4QS
CAS number
306296-47-9
InChI Key
CNPVJJQCETWNEU-CYFREDJKSA-N
InChI
InChI=1S/C28H38F3N5O2/c1-19-16-35(14-15-36(19)24(17-38-5)22-6-8-23(9-7-22)28(29,30)31)27(4)10-12-34(13-11-27)26(37)25-20(2)32-18-33-21(25)3/h6-9,18-19,24H,10-17H2,1-5H3/t19-,24-/m0/s1
IUPAC Name
5-{4-[(3S)-4-[(1R)-2-methoxy-1-[4-(trifluoromethyl)phenyl]ethyl]-3-methylpiperazin-1-yl]-4-methylpiperidine-1-carbonyl}-4,6-dimethylpyrimidine
SMILES
COC[C@H](N1CCN(C[C@@H]1C)C1(C)CCN(CC1)C(=O)C1=C(C)N=CN=C1C)C1=CC=C(C=C1)C(F)(F)F

References

General References
  1. Idemyor V: Human immunodeficiency virus (HIV) entry inhibitors (CCR5 specific blockers) in development: are they the next novel therapies? HIV Clin Trials. 2005 Sep-Oct;6(5):272-7. [Article]
  2. Emmelkamp JM, Rockstroh JK: CCR5 antagonists: comparison of efficacy, side effects, pharmacokinetics and interactions--review of the literature. Eur J Med Res. 2007 Oct 15;12(9):409-17. [Article]
  3. Ghosal A, Ramanathan R, Yuan Y, Hapangama N, Chowdhury SK, Kishnani NS, Alton KB: Identification of human liver cytochrome P450 enzymes involved in biotransformation of vicriviroc, a CCR5 receptor antagonist. Drug Metab Dispos. 2007 Dec;35(12):2186-95. Epub 2007 Sep 7. [Article]
ChemSpider
2278662
BindingDB
50145685
ChEBI
94843
ChEMBL
CHEMBL82301
ZINC
ZINC000022010579
Wikipedia
Vicriviroc

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
PhaseStatusPurposeConditionsCount
3CompletedTreatmentAcquired Immune Deficiency Syndrome (AIDS) / Human Immunodeficiency Virus (HIV) Infections2
3WithdrawnTreatmentAcquired Immune Deficiency Syndrome (AIDS) / Human Immunodeficiency Virus (HIV) Infections1
2CompletedTreatmentAcquired Immune Deficiency Syndrome (AIDS) / Human Immunodeficiency Virus (HIV) Infections1
2CompletedTreatmentColorectal Neoplasms1
2CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections4

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 Solubility0.0362 mg/mLALOGPS
logP3.29ALOGPS
logP2.8Chemaxon
logS-4.2ALOGPS
pKa (Strongest Basic)8.44Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count6Chemaxon
Hydrogen Donor Count0Chemaxon
Polar Surface Area61.8 Å2Chemaxon
Rotatable Bond Count7Chemaxon
Refractivity142.64 m3·mol-1Chemaxon
Polarizability56.3 Å3Chemaxon
Number of Rings4Chemaxon
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/MSsplash10-0f89-0000090000-98331b1c0632095e8e84
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-0000690000-a2ca9df85cbe80a59b8f
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0f89-0111190000-f7fe3757f1c371a57b24
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0gc9-0309880000-2552194422bb55b0443d
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-052r-0932770000-5b6b4a9c9b8d3aa4cf4c
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-00gi-0367980000-af17ef6f70c5756e1db1
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-223.32796
predicted
DeepCCS 1.0 (2019)
[M+H]+225.53995
predicted
DeepCCS 1.0 (2019)
[M+Na]+231.45247
predicted
DeepCCS 1.0 (2019)

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. Wilkin TJ, Su Z, Kuritzkes DR, Hughes M, Flexner C, Gross R, Coakley E, Greaves W, Godfrey C, Skolnik PR, Timpone J, Rodriguez B, Gulick RM: HIV type 1 chemokine coreceptor use among antiretroviral-experienced patients screened for a clinical trial of a CCR5 inhibitor: AIDS Clinical Trial Group A5211. Clin Infect Dis. 2007 Feb 15;44(4):591-5. Epub 2007 Jan 17. [Article]
  2. Tsibris AM, Sagar M, Gulick RM, Su Z, Hughes M, Greaves W, Subramanian M, Flexner C, Giguel F, Leopold KE, Coakley E, Kuritzkes DR: In vivo emergence of vicriviroc resistance in a human immunodeficiency virus type 1 subtype C-infected subject. J Virol. 2008 Aug;82(16):8210-4. doi: 10.1128/JVI.00444-08. Epub 2008 May 21. [Article]
  3. De Clercq E: Emerging anti-HIV drugs. Expert Opin Emerg Drugs. 2005 May;10(2):241-73. [Article]

Enzymes

Details1. Cytochrome P450 3A4
Kind
Protein
Organism
Humans
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 react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [Article]
Details2. Cytochrome P450 3A5
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Oxygen binding
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 oxidizes a variety of structurally un...
Gene Name
CYP3A5
Uniprot ID
P20815
Uniprot Name
Cytochrome P450 3A5
Molecular Weight
57108.065 Da
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [Article]
Details3. Cytochrome P450 2C9
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid 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 oxidizes a variety of structurally un...
Gene Name
CYP2C9
Uniprot ID
P11712
Uniprot Name
Cytochrome P450 2C9
Molecular Weight
55627.365 Da
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [Article]

Drug created at March 19, 2008 16:44 / Updated at June 28, 2022 01:35