Identification
- Summary
Maraviroc is a CCR5 co-receptor antagonist used with other antiretroviral medications to treat CCR5-tropic HIV-1 infection.
- Brand Names
- Celsentri, Selzentry
- Generic Name
- Maraviroc
- DrugBank Accession Number
- DB04835
- Background
Maraviroc (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.
- Type
- Small Molecule
- Groups
- Approved, Investigational
- Structure
Structure for Maraviroc (DB04835)
- Weight
- Average: 513.6655
Monoisotopic: 513.327917369 - Chemical Formula
- C29H41F2N5O
- Synonyms
- Maraviroc
- Maravirocum
Pharmacology
- Indication
Maraviroc is indicated in combination with other antiretroviral agents for the treatment of CCR5-tropic HIV-1 infection in adults and pediatric patients weighing at least 2kg.1 It is not recommended in patients with dual/mixed- or CXCR4-tropic HIV-1.
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Adjunct therapy in treatment of Ccr5-tropic human immunodeficiency virus type 1 (hiv-1) infection •••••••••••• ••••••••• •••••• •••• ••••••••• •••••• Adjunct therapy in treatment of Ccr5-tropic human immunodeficiency virus type 1 (hiv-1) infection •••••••••••• ••••• ••••••••• •••••• Used in combination to treat Hiv-1 infection •••••••••••• - Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Maraviroc 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 action
Maraviroc 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.
Target Actions Organism AC-C chemokine receptor type 5 antagonistinhibitorHumans - Absorption
The 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 binding
Approximately 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 elimination
Not Available
- Half-life
14-18 hours
- Clearance
Not Available
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- 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.
Drug Interaction Integrate drug-drug
interactions in your softwareAbametapir The serum concentration of Maraviroc can be increased when it is combined with Abametapir. Adagrasib The serum concentration of Maraviroc can be increased when it is combined with Adagrasib. Adenovirus type 7 vaccine live The therapeutic efficacy of Adenovirus type 7 vaccine live can be decreased when used in combination with Maraviroc. Amiodarone The metabolism of Maraviroc can be decreased when combined with Amiodarone. Amprenavir The metabolism of Maraviroc can be decreased when combined with Amprenavir. - Food Interactions
- Avoid St. John's Wort. This herb induces CYP3A metabolism and may reduce serum levels of maraviroc.
- Take with or without food.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Images
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Celsentri Tablet, film coated 150 mg Oral Vii V Healthcare B.V. 2016-09-08 Not applicable EU 
Celsentri Tablet, film coated 150 mg Oral Vii V Healthcare B.V. 2016-09-08 Not applicable EU Celsentri Tablet, film coated 75 mg Oral Vii V Healthcare B.V. 2020-12-16 Not applicable EU Celsentri Tablet, film coated 300 mg Oral Vii V Healthcare B.V. 2016-09-08 Not applicable EU Celsentri Tablet, film coated 300 mg Oral Vii V Healthcare B.V. 2016-09-08 Not applicable EU - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Maraviroc Tablet, film coated 300 mg/1 Oral XLCARE Pharmaceuticals INC. 2023-06-01 Not applicable US 
Maraviroc Tablet, film coated 150 mg/1 Oral Camber Pharmaceuticals, Inc. 2022-02-06 Not applicable US Maraviroc Tablet, film coated 300 mg/1 Oral i3 Pharmaceuticals, LLC 2023-09-15 Not applicable US Maraviroc Tablet, film coated 150 mg/1 Oral XLCARE Pharmaceuticals INC. 2023-06-01 Not applicable US Maraviroc Tablet, film coated 150 mg/1 Oral i3 Pharmaceuticals, LLC 2023-09-15 Not applicable US
Categories
- ATC Codes
- J05AX09 — Maraviroc
- Drug Categories
- Anti-HIV Agents
- Anti-Infective Agents
- Anti-Retroviral Agents
- Antiinfectives for Systemic Use
- Antiviral Agents
- Antivirals for Systemic Use
- CCR5 Co-receptor Antagonist
- CCR5 Receptor Antagonists
- Cyclohexanes
- Cycloparaffins
- Cytochrome P-450 CYP3A Substrates
- Cytochrome P-450 CYP3A4 Substrates
- Cytochrome P-450 Substrates
- Direct Acting Antivirals
- Hepatotoxic Agents
- HIV Fusion Inhibitors
- Triazoles
- Viral Fusion Protein Inhibitors
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound 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.
- Kingdom
- Organic compounds
- Super Class
- Alkaloids and derivatives
- Class
- Tropane alkaloids
- Sub Class
- Not Available
- Direct Parent
- Tropane alkaloids
- Alternative Parents
- Aralkylamines / Cyclohexyl halides / Piperidines / N-alkylpyrrolidines / Benzene and substituted derivatives / Triazoles / Heteroaromatic compounds / Trialkylamines / Secondary carboxylic acid amides / Amino acids and derivatives show 7 more
- Substituents
- 1,2,4-triazole / Alkyl fluoride / Alkyl halide / Amine / Amino acid or derivatives / Aralkylamine / Aromatic heteropolycyclic compound / Azacycle / Azole / Benzenoid show 23 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- organofluorine compound, azabicycloalkane, monocarboxylic acid amide, triazoles (CHEBI:63608)
- Affected organisms
- Human Immunodeficiency Virus
Chemical Identifiers
- UNII
- MD6P741W8A
- CAS number
- 376348-65-1
- InChI Key
- GSNHKUDZZFZSJB-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-carboxamide
- SMILES
- CC(C)C1=NN=C(C)N1[C@H]1C[C@@H]2CC[C@H](C1)N2CC[C@H](NC(=O)C1CCC(F)(F)CC1)C1=CC=CC=C1
References
- Synthesis Reference
- US020013337
- General References
- FDA Approved Drug Products: Selzentry (maraviroc) for oral use [Link]
- External Links
- PubChem Compound
- 3002977
- PubChem Substance
- 46508040
- ChemSpider
- 20078004
- BindingDB
- 50334986
- 620216
- ChEBI
- 63608
- ChEMBL
- CHEMBL1201187
- ZINC
- ZINC000100003902
- Therapeutic Targets Database
- DNC001487
- PharmGKB
- PA164768835
- Guide to Pharmacology
- GtP Drug Page
- PDBe Ligand
- MRV
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Maraviroc
- PDB Entries
- 4mbs
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 4 Completed Not Available Healthy Subjects (HS) 1 4 Completed Not Available Human Immunodeficiency Virus (HIV) Infections / Proteinuria 1 4 Completed Basic Science Human Immunodeficiency Virus (HIV) Infections 1 4 Completed Other Human Immunodeficiency Virus Infection(HIV)/Acquired Immunodeficiency Syndrome (AIDS) 1 4 Completed Prevention Human Immunodeficiency Virus (HIV) Infections 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Goedecke GmbH
- Lake Erie Medical and Surgical Supply
- Pfizer Inc.
- Physicians Total Care Inc.
- ViiV Healthcare ULC
- Dosage Forms
Form Route Strength Solution Oral 20 MG/ML Tablet Oral 150 mg Tablet Oral 300 mg Tablet, film coated Oral 25 MG Tablet, film coated Oral 75 MG Tablet, coated Oral 150 mg Tablet, coated Oral 300 mg Tablet, coated Oral Tablet, film coated Oral 150 mg Tablet, film coated Oral 300 mg Kit; solution Oral 20 mg/1mL Solution Oral 20 mg/1mL Tablet Oral 150.000 mg Tablet, film coated Oral 150 mg/1 Tablet, film coated Oral 25 mg/1 Tablet, film coated Oral 300 mg/1 Tablet, film coated Oral 75 mg/1 - Prices
Unit description Cost Unit Selzentry 150 mg tablet 18.36USD tablet Selzentry 300 mg tablet 18.36USD tablet DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region CA2350073 No 2007-04-17 2019-12-23 Canada 
CA2408909 No 2006-06-27 2021-05-09 Canada US6586430 No 2003-07-01 2019-12-01 US US6667314 Yes 2003-12-23 2022-02-06 US US7368460 Yes 2008-05-06 2023-05-25 US US7576097 Yes 2009-08-18 2021-11-25 US
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.0106 mg/mL ALOGPS logP 4.3 ALOGPS logP 3.63 Chemaxon logS -4.7 ALOGPS pKa (Strongest Acidic) 13.98 Chemaxon pKa (Strongest Basic) 9.65 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 4 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 63.05 Å2 Chemaxon Rotatable Bond Count 8 Chemaxon Refractivity 142.88 m3·mol-1 Chemaxon Polarizability 56.02 Å3 Chemaxon Number of Rings 5 Chemaxon Bioavailability 1 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.997 Blood Brain Barrier + 0.8329 Caco-2 permeable - 0.8957 P-glycoprotein substrate Substrate 0.6716 P-glycoprotein inhibitor I Inhibitor 0.8931 P-glycoprotein inhibitor II Inhibitor 0.9431 Renal organic cation transporter Non-inhibitor 0.5695 CYP450 2C9 substrate Non-substrate 0.8308 CYP450 2D6 substrate Non-substrate 0.7344 CYP450 3A4 substrate Substrate 0.8199 CYP450 1A2 substrate Non-inhibitor 0.8616 CYP450 2C9 inhibitor Inhibitor 0.6028 CYP450 2D6 inhibitor Non-inhibitor 0.8331 CYP450 2C19 inhibitor Inhibitor 0.5684 CYP450 3A4 inhibitor Inhibitor 0.6066 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.7814 Ames test Non AMES toxic 0.63 Carcinogenicity Non-carcinogens 0.706 Biodegradation Not ready biodegradable 1.0 Rat acute toxicity 2.7115 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9864 hERG inhibition (predictor II) Inhibitor 0.8971
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 219.8899 predictedDeepCCS 1.0 (2019) [M+H]+ 221.7853 predictedDeepCCS 1.0 (2019) [M+Na]+ 227.6039 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- AntagonistInhibitor
- 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
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- 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. [Article]
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
- Levy JA: HIV pathogenesis: 25 years of progress and persistent challenges. AIDS. 2009 Jan 14;23(2):147-60. doi: 10.1097/QAD.0b013e3283217f9f. [Article]
- 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. [Article]
- 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. [Article]
- Clark IA, Vissel B: Neurodegenerative disease treatments by direct TNF reduction, SB623 cells, maraviroc and irisin and MCC950, from an inflammatory perspective - a Commentary. Expert Rev Neurother. 2019 Jun;19(6):535-543. doi: 10.1080/14737175.2019.1618710. Epub 2019 May 24. [Article]
Enzymes
- 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
- Abel S, Back DJ, Vourvahis M: Maraviroc: pharmacokinetics and drug interactions. Antivir Ther. 2009;14(5):607-18. [Article]
- 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. [Article]
- 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. [Article]
Drug created at September 12, 2007 01:14 / Updated at February 20, 2024 23:54