Identification
- Summary
Cabotegravir is an HIV-1 integrase inhibitor used for treatment and pre-exposure prophylaxis of HIV-1 infection.
- Brand Names
- Apretude, Vocabria
- Generic Name
- Cabotegravir
- DrugBank Accession Number
- DB11751
- Background
Cabotegravir, or GSK1265744, is an HIV-1 integrase inhibitor that is prescribed with the non-nucleoside reverse transcriptase inhibitor, rilpivirine.4,6,7 Early research into cabotegravir showed it had lower oral bioavailability than dolutegravir,4 which resulted in the development of long acting monthly intramuscular injection formulation for cabotegravir.4,7
Cabotegravir was granted FDA approval on 21 January 2021 in combination with rilpivirine to treat HIV-1 infection in virologically suppressed individuals.8 While previously administered once monthly only, this combination product was granted FDA approval for dosing every two months on February 01, 2022 11 and without the need for an oral lead-in period prior.7
- Type
- Small Molecule
- Groups
- Approved, Investigational
- Structure
Structure for Cabotegravir (DB11751)
- Weight
- Average: 405.358
Monoisotopic: 405.113626985 - Chemical Formula
- C19H17F2N3O5
- Synonyms
- Cabotegravir
- External IDs
- 744 LA
- GSK 1265744
- GSK 744
- GSK-1265744A
- GSK1265744
- GSK1265744A
- GSK744
- GSK744 LA
- GSK744 LAP
- S-265744
- S/GSK1265744
Pharmacology
- Indication
Oral cabotegravir is indicated in combination with rilpivirine for the short-term treatment of HIV-1 in virologically suppressed adults with no history of treatment failure to assess tolerability of cabotegravir or who have missed an injected dose of cabotegravir.6 Intramuscular extended-release cabotegravir in combination with rilpivirine is indicated as a complete regimen for the treatment of HIV-1 infection in adults and adolescents 12 years of age and older weighing at least 35 kg to replace the current antiretroviral regimen in those who are virologically suppressed (HIV-1 RNA <50 copies/mL) on a stable antiretroviral regimen with no history of treatment failure and with no known or suspected resistance to either cabotegravir or rilpivirine.7
An extended-release injectable suspension formulation of cabotegravir is also indicated for the prevention of sexually-acquired HIV-1 infection (i.e. for pre-exposure prophylaxis, PrEP) in at-risk adults and adolescents weighing at least 35kg.10
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 Used in combination to treat Human immunodeficiency virus type 1 (hiv-1) Combination Product in combination with: Rilpivirine (DB08864) •••••••••••• ••••••••••• ••••• •• ••••••• •• ••••••••• •••••••• •••••••••••••••••••••••• •••••• •• ••••• •• •• Used in combination to treat Human immunodeficiency virus type 1 (hiv-1) Regimen in combination with: Rilpivirine (DB08864) •••••••••••• ••••• •••••••••••••••••••••••• •• ••••••• •• ••••••••• ••••••• •••••• Treatment of Human immunodeficiency virus type 1 (hiv-1) infection •••••••••••• Prevention of Human immunodeficiency virus type 1 (hiv-1) infection •••••••••••• ••••••••••• ••••• ••• •••• ••••••••• •••••• •• ••••• •• •• •••••••••• ••••••••••• •••••••• ••••••• - Associated Therapies
- 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
Cabotegravir is an inhibitor of HIV integrase, which reduces viral replication.6,7 It has a long duration of action as the oral tablet is given daily and the intramuscular suspension is given monthly.6,7 Patients should be counselled regarding the risk of hypersensitivity, hepatotoxicity, and depression.6,7
- Mechanism of action
Cabotegravir binds to the active site of HIV integrase, preventing strand transfer of the viral genome into the host genome, and preventing replication of the virus.6,7
Target Actions Organism AIntegrase inhibitorHuman immunodeficiency virus 1 - Absorption
Oral cabotegravir has a Tmax of 3 hours, reaches a Cmax of 8.0 µg/mL, and has an AUC of 145 µg*h/mL.6 Intramuscular extended-release cabotegravir has a Tmax of 7 days, reaches a Cmax of 8.0 µg/mL, and has an AUC of 1591 µg*h/mL.7
- Volume of distribution
Data regarding the volume of distribution of cabotegravir is not readily available.3,7,9
- Protein binding
Cabotegravir is >99.8% bound to proteins in plasma, usually alubmin.5,6
- Metabolism
Cabotegravir is O-glucuronidated to the M1 and M2 metabolites, with 67% of glucuronidation performed by UGT1A1, and 33% by UGT1A9.1,2
Hover over products below to view reaction partners
- Route of elimination
An oral radiolabelled dose of cabotegravir is 58.5% recovered in the feces and 26.8% recovered in the urine.1,2,6
- Half-life
The mean half life of oral cabotegravir is 41 hours.6 The mean half life of intramuscular extended-release cabotegravir is 5.6-11.5 weeks.7
- Clearance
Data regarding the clearance of cabotegravir is not readily available.3,7,9 Clearance in dogs was 0.34 mL/min/kg and in cynomolgus monkeys was 0.32 mL/min/kg.4
- 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
Data regarding the toxicity of cabotegravir is not readily available.6,7,9 In the event of overdose, patients should have their vital signs monitored, including an ECG to monitor the QT interval.6,7 Treat patients symptomatically and supportively.6,7 As cabotegravir is highly protein bound, dialysis is not expected to remove a significant amount of the drug from plasma.6,7
- 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 softwareAcamprosate The excretion of Acamprosate can be decreased when combined with Cabotegravir. Acyclovir The excretion of Acyclovir can be decreased when combined with Cabotegravir. Adefovir dipivoxil The excretion of Adefovir dipivoxil can be decreased when combined with Cabotegravir. Adenine The metabolism of Cabotegravir can be decreased when combined with Adenine. Adenovirus type 7 vaccine live The therapeutic efficacy of Adenovirus type 7 vaccine live can be decreased when used in combination with Cabotegravir. - Food Interactions
- Take at the same time every day. Take the oral tablets at the same time every day.
- Take with food. Take the oral tablets with a meal.
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 Ingredients
Ingredient UNII CAS InChI Key Cabotegravir sodium 3L12PT535M 1051375-13-3 AEZBWGMXBKPGFP-KIUAEZIZSA-M - International/Other Brands
- Vocabria (ViiV Healthcare)
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Apretude Injection, suspension, extended release; Kit 200 mg/1mL Intramuscular ViiV Healthcare Company 2021-12-20 Not applicable US 
Vocabria Injection 400 mg Intramuscular Vii V Healthcare B.V. 2021-02-08 Not applicable EU 
Vocabria Tablet 30 mg Oral ViiV Healthcare ULC 2020-09-21 Not applicable Canada 
Vocabria Tablet, film coated 30 mg Oral Vii V Healthcare B.V. 2021-02-08 Not applicable EU Vocabria Tablet, film coated 30 mg/1 Oral ViiV Healthcare Company 2021-01-21 Not applicable US - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Cabenuva Cabotegravir (200 mg/1mL) + Rilpivirine (300 mg/1mL) Injection, suspension, extended release; Kit Intramuscular ViiV Healthcare Company 2021-01-21 Not applicable US Cabenuva Cabotegravir (200 mg / mL) + Rilpivirine (300 mg / mL) Kit; Suspension, extended release Intramuscular ViiV Healthcare ULC 2020-09-21 Not applicable Canada Cabenuva Cabotegravir (200 mg/1mL) + Rilpivirine (300 mg/1mL) Injection, suspension, extended release; Kit Intramuscular ViiV Healthcare Company 2021-01-21 Not applicable US Cabenuva Cabotegravir (200 mg / mL) + Rilpivirine (300 mg / mL) Kit; Suspension, extended release Intramuscular ViiV Healthcare ULC 2020-09-21 Not applicable Canada
Categories
- ATC Codes
- J05AJ04 — Cabotegravir
- Drug Categories
- Anti-HIV Agents
- Anti-Infective Agents
- Anti-Retroviral Agents
- Antiinfectives for Systemic Use
- Antiviral Agents
- Antivirals for Systemic Use
- BCRP/ABCG2 Substrates
- Direct Acting Antivirals
- Enzyme Inhibitors
- HIV Integrase Inhibitors
- Human Immunodeficiency Virus Integrase Strand Transfer Inhibitor
- Integrase Inhibitors
- OAT1/SLC22A6 inhibitors
- OAT3/SLC22A8 Inhibitors
- Organic Anion Transporter 1 Inhibitors
- P-glycoprotein substrates
- Piperazines
- Pyridines
- UGT1A1 Substrates
- UGT1A9 Substrates
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as pyridinecarboxylic acids and derivatives. These are compounds containing a pyridine ring bearing a carboxylic acid group or a derivative thereof.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Pyridines and derivatives
- Sub Class
- Pyridinecarboxylic acids and derivatives
- Direct Parent
- Pyridinecarboxylic acids and derivatives
- Alternative Parents
- 2-heteroaryl carboxamides / Fluorobenzenes / Hydroxypyridines / Aryl fluorides / Vinylogous amides / Vinylogous acids / Tertiary carboxylic acid amides / Heteroaromatic compounds / Oxazolidines / Lactams show 8 more
- Substituents
- 2-heteroaryl carboxamide / Aromatic heteropolycyclic compound / Aryl fluoride / Aryl halide / Azacycle / Benzenoid / Carboxamide group / Carboxylic acid derivative / Cyclic ketone / Fluorobenzene show 20 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- HMH0132Z1Q
- CAS number
- 1051375-10-0
- InChI Key
- WCWSTNLSLKSJPK-LKFCYVNXSA-N
- InChI
- InChI=1S/C19H17F2N3O5/c1-9-8-29-14-7-23-6-12(16(25)17(26)15(23)19(28)24(9)14)18(27)22-5-10-2-3-11(20)4-13(10)21/h2-4,6,9,14,26H,5,7-8H2,1H3,(H,22,27)/t9-,14+/m0/s1
- IUPAC Name
- (3R,6S)-N-[(2,4-difluorophenyl)methyl]-10-hydroxy-6-methyl-8,11-dioxo-4-oxa-1,7-diazatricyclo[7.4.0.0^{3,7}]trideca-9,12-diene-12-carboxamide
- SMILES
- [H][C@@]12CN3C=C(C(=O)NCC4=C(F)C=C(F)C=C4)C(=O)C(O)=C3C(=O)N1[C@@H](C)CO2
References
- General References
- Bowers GD, Culp A, Reese MJ, Tabolt G, Moss L, Piscitelli S, Huynh P, Wagner D, Ford SL, Gould EP, Pan R, Lou Y, Margolis DA, Spreen WR: Disposition and metabolism of cabotegravir: a comparison of biotransformation and excretion between different species and routes of administration in humans. Xenobiotica. 2016;46(2):147-62. doi: 10.3109/00498254.2015.1060372. Epub 2015 Jul 1. [Article]
- Patel M, Eberl HC, Wolf A, Pierre E, Polli JW, Zamek-Gliszczynski MJ: Mechanistic Basis of Cabotegravir-Glucuronide Disposition in Humans. J Pharmacol Exp Ther. 2019 Aug;370(2):269-277. doi: 10.1124/jpet.119.258384. Epub 2019 Jun 7. [Article]
- Spreen W, Min S, Ford SL, Chen S, Lou Y, Bomar M, St Clair M, Piscitelli S, Fujiwara T: Pharmacokinetics, safety, and monotherapy antiviral activity of GSK1265744, an HIV integrase strand transfer inhibitor. HIV Clin Trials. 2013 Sep-Oct;14(5):192-203. doi: 10.1310/hct1405-192. [Article]
- Johns BA, Kawasuji T, Weatherhead JG, Taishi T, Temelkoff DP, Yoshida H, Akiyama T, Taoda Y, Murai H, Kiyama R, Fuji M, Tanimoto N, Jeffrey J, Foster SA, Yoshinaga T, Seki T, Kobayashi M, Sato A, Johnson MN, Garvey EP, Fujiwara T: Carbamoyl pyridone HIV-1 integrase inhibitors 3. A diastereomeric approach to chiral nonracemic tricyclic ring systems and the discovery of dolutegravir (S/GSK1349572) and (S/GSK1265744). J Med Chem. 2013 Jul 25;56(14):5901-16. doi: 10.1021/jm400645w. Epub 2013 Jul 11. [Article]
- Shaik JSB, Ford SL, Lou Y, Zhang Z, Bakshi KK, Tenorio AR, Trezza C, Spreen WR, Patel P: A Phase 1 Study to Evaluate the Pharmacokinetics and Safety of Cabotegravir in Patients With Hepatic Impairment and Healthy Matched Controls. Clin Pharmacol Drug Dev. 2019 Jul;8(5):664-673. doi: 10.1002/cpdd.655. Epub 2019 Feb 27. [Article]
- FDA Approved Drug Products: Vocabria (Cabotegravir) Oral Tablets [Link]
- FDA Approved Drug Products: Cabenuva (Cabotegravir and Rilpivirine) Intramuscular Extended-Release Suspension [Link]
- FDA News Release: FDA Approves First Extended-Release, Injectable Drug Regimen for Adults Living with HIV [Link]
- Cayman Chemical: Cabotegravir MSDS [Link]
- FDA Approved Drug Products: Apretude (cabotegravir) extended-release suspension for intramuscular injection [Link]
- BioSpace News: ViiV Healthcare Announces US FDA Approval of Cabenuva (cabotegravir, rilpivirine) for Use Every Two Months, Expanding the Label of the First and Only Complete Long-Acting HIV Treatment [Link]
- FDA Approved Drug Products: APRETUDE (cabotegravir extended-release injectable suspension), for intramuscular use (Jan 2024) [Link]
- External Links
- PubChem Compound
- 54713659
- PubChem Substance
- 347828108
- ChemSpider
- 30829503
- BindingDB
- 50492496
- 2475077
- ChEBI
- 172944
- ChEMBL
- CHEMBL2403238
- ZINC
- ZINC000096927633
- Wikipedia
- Cabotegravir
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 Active Not Recruiting Treatment Human Immunodeficiency Virus (HIV) Infections 1 4 Recruiting Prevention Breastfeeding / Pre-Exposure Prophylaxis (PrEP) 1 4 Recruiting Prevention Coronavirus Disease 2019 (COVID‑19) / Human Immunodeficiency Virus (HIV) Infections / STI 1 4 Recruiting Prevention Human Immunodeficiency Virus (HIV) Infections 2 4 Recruiting Treatment Human Immunodeficiency Virus (HIV) Infections 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Injection, suspension, extended release; kit Intramuscular 200 mg/1mL Injection, suspension, extended release; kit Intramuscular Kit; suspension, extended release Intramuscular Injection Intramuscular 400 mg Injection Intramuscular 600 mg Injection, suspension Intramuscular 400 MG Injection, suspension Intramuscular 600 MG Suspension Intramuscular 600.000 mg Tablet Oral 30 mg Tablet Oral 31.620 mg Tablet, film coated Oral 30 MG Tablet, film coated Oral 30 mg/1 - Prices
- Not Available
- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US7125879 No 2006-10-24 2022-08-09 US US6838464 No 2005-01-04 2021-02-26 US US8080551 No 2011-12-20 2023-04-11 US US8410103 No 2013-04-02 2026-04-28 US US10927129 No 2021-02-23 2026-04-28 US US11224597 No 2011-09-15 2031-09-15 US US11389447 No 2007-06-30 2027-06-30 US
Properties
- State
- Liquid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source logP 1.04 Chemaxon pKa (Strongest Acidic) 10.04 Chemaxon pKa (Strongest Basic) -0.7 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 6 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 99.18 Å2 Chemaxon Rotatable Bond Count 3 Chemaxon Refractivity 97.9 m3·mol-1 Chemaxon Polarizability 38.11 Å3 Chemaxon Number of Rings 4 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 191.01923 predictedDeepCCS 1.0 (2019) [M-H]- 191.01923 predictedDeepCCS 1.0 (2019) [M-H]- 191.01923 predictedDeepCCS 1.0 (2019) [M+H]+ 193.37724 predictedDeepCCS 1.0 (2019) [M+H]+ 193.37724 predictedDeepCCS 1.0 (2019) [M+H]+ 193.37724 predictedDeepCCS 1.0 (2019) [M+Na]+ 199.50215 predictedDeepCCS 1.0 (2019) [M+Na]+ 199.50215 predictedDeepCCS 1.0 (2019) [M+Na]+ 199.50215 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Human immunodeficiency virus 1
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Zinc ion binding
- Specific Function
- Not Available
- Gene Name
- pol
- Uniprot ID
- Q7ZJM1
- Uniprot Name
- Integrase
- Molecular Weight
- 32226.645 Da
References
- FDA Approved Drug Products: Vocabria (Cabotegravir) Oral Tablets [Link]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Steroid binding
- Specific Function
- UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the...
- Gene Name
- UGT1A1
- Uniprot ID
- P22309
- Uniprot Name
- UDP-glucuronosyltransferase 1-1
- Molecular Weight
- 59590.91 Da
References
- FDA Approved Drug Products: Vocabria (Cabotegravir) Oral Tablets [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Retinoic acid binding
- Specific Function
- UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform has specificity for phenols. Isoform 2 lacks trans...
- Gene Name
- UGT1A9
- Uniprot ID
- O60656
- Uniprot Name
- UDP-glucuronosyltransferase 1-9
- Molecular Weight
- 59940.495 Da
References
- FDA Approved Drug Products: Vocabria (Cabotegravir) Oral Tablets [Link]
Carriers
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Binder
- General Function
- Toxic substance binding
- Specific Function
- Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
- Gene Name
- ALB
- Uniprot ID
- P02768
- Uniprot Name
- Serum albumin
- Molecular Weight
- 69365.94 Da
References
- Shaik JSB, Ford SL, Lou Y, Zhang Z, Bakshi KK, Tenorio AR, Trezza C, Spreen WR, Patel P: A Phase 1 Study to Evaluate the Pharmacokinetics and Safety of Cabotegravir in Patients With Hepatic Impairment and Healthy Matched Controls. Clin Pharmacol Drug Dev. 2019 Jul;8(5):664-673. doi: 10.1002/cpdd.655. Epub 2019 Feb 27. [Article]
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Sodium-independent organic anion transmembrane transporter activity
- Specific Function
- Involved in the renal elimination of endogenous and exogenous organic anions. Functions as organic anion exchanger when the uptake of one molecule of organic anion is coupled with an efflux of one ...
- Gene Name
- SLC22A6
- Uniprot ID
- Q4U2R8
- Uniprot Name
- Solute carrier family 22 member 6
- Molecular Weight
- 61815.78 Da
References
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Sodium-independent organic anion transmembrane transporter activity
- Specific Function
- Plays an important role in the excretion/detoxification of endogenous and exogenous organic anions, especially from the brain and kidney. Involved in the transport basolateral of steviol, fexofenad...
- Gene Name
- SLC22A8
- Uniprot ID
- Q8TCC7
- Uniprot Name
- Solute carrier family 22 member 8
- Molecular Weight
- 59855.585 Da
References
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Xenobiotic-transporting atpase activity
- Specific Function
- Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
- Gene Name
- ABCB1
- Uniprot ID
- P08183
- Uniprot Name
- Multidrug resistance protein 1
- Molecular Weight
- 141477.255 Da
References
- FDA Approved Drug Products: Vocabria (Cabotegravir) Oral Tablets [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Xenobiotic-transporting atpase activity
- Specific Function
- High-capacity urate exporter functioning in both renal and extrarenal urate excretion. Plays a role in porphyrin homeostasis as it is able to mediates the export of protoporhyrin IX (PPIX) both fro...
- Gene Name
- ABCG2
- Uniprot ID
- Q9UNQ0
- Uniprot Name
- ATP-binding cassette sub-family G member 2
- Molecular Weight
- 72313.47 Da
References
- FDA Approved Drug Products: Vocabria (Cabotegravir) Oral Tablets [Link]
Drug created at October 20, 2016 20:45 / Updated at February 01, 2024 01:51