Cabotegravir

Cabotegravir
Clinical data
Trade namesVocabria, Apretude
Other namesS/GSK1265744, GSK744
AHFS/Drugs.comMonograph
MedlinePlusa621010
License data
Pregnancy
category
Routes of
administration		By mouth, intramuscular
ATC code
Legal status
Legal status
Pharmacokinetic data
Protein binding>99%
MetabolismUGT1A1
Metabolitesglucuronide
Elimination half-lifetablets: 41 hours
injection: 5.6–11.5 weeks
Excretion47% via feces, 27% via urine
Identifiers
IUPAC name
  • N-((2,4-Difluorophenyl)methyl)-6-hydroxy-3-methyl-5,7-dioxo-2,3,5,7,11,11a-hexahydro(1,3)oxazolo(3,2-a)pyrido(1,2-d)pyrazine-8-carboxamide
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.306.452
Chemical and physical data
FormulaC19H17F2N3O5
Molar mass405.358 g·mol−1
3D model (JSmol)
SMILES
  • C[C@H]1CO[C@H]2N1C(=O)c3c(c(=O)c(cn3C2)C(=O)NCc4ccc(cc4F)F)O

  • as salt: [Na+].C[C@H]1CO[C@@H]2CN3C=C(C(=O)NCC4=CC=C(F)C=C4F)C(=O)C([O-])=C3C(=O)N12
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
  • Key:WCWSTNLSLKSJPK-LKFCYVNXSA-N

  • as salt: InChI=1S/C19H17F2N3O5.Na/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);/q;+1/p-1/t9-,14+;/m0./s1
  • Key:AEZBWGMXBKPGFP-KIUAEZIZSA-M

Cabotegravir, sold under the brand name Vocabria among others, is an antiretroviral medication used for the treatment and prevention of HIV/AIDS. It is available in the form of tablets and as an intramuscular injection, as well as in an injectable combination with rilpivirine under the brand name Cabenuva.[7][13]

It is an integrase inhibitor with a carbamoyl pyridone structure similar to that of dolutegravir.[14]

In December 2021, the U.S. Food and Drug Administration approved cabotegravir for pre-exposure prophylaxis (PrEP) in at-risk people under the brand name Apretude.[15] In September 2023, it was approved for pre-exposure prophylaxis in the European Union.[11]

  1. ^ a b "Vocabria (cabotegravir) film-coated tablets Product Information". TGA eBS. 12 June 2021. Archived from the original on 13 June 2021. Retrieved 12 June 2021.
  2. ^ a b "Vocabria". Therapeutic Goods Administration (TGA). 26 February 2021. Archived from the original on 9 September 2021. Retrieved 8 September 2021.
  3. ^ "Summary for ARTG Entry: 323721 VOCABRIA cabotegravir (as sodium) 30 mg film-coated tablet, bottle". Therapeutic Goods Administration. The Government of Australia. 13 August 2021.
  4. ^ "Vocabria Product information". Health Canada. 25 April 2012. Archived from the original on 24 February 2021. Retrieved 22 January 2021.
  5. ^ "Regulatory Decision Summary for Apretude". Drug and Health Products Portal. 10 May 2024. Retrieved 27 December 2024.
  6. ^ "Vocabria- cabotegravir sodium tablet, film coated". DailyMed. Archived from the original on 15 June 2021. Retrieved 12 June 2021.
  7. ^ a b "FDA Approves First Extended-Release, Injectable Drug Regimen for Adults Living with HIV". U.S. Food and Drug Administration (FDA) (Press release). 21 January 2021. Archived from the original on 21 January 2021. Retrieved 21 January 2021. This article incorporates text from this source, which is in the public domain.
  8. ^ "Apretude- cabotegravir kit". DailyMed. Archived from the original on 25 December 2021. Retrieved 24 December 2021.
  9. ^ "Vocabria EPAR". European Medicines Agency (EMA). 13 October 2020. Archived from the original on 14 July 2021. Retrieved 22 January 2021. Text was copied from this source which is copyright European Medicines Agency. Reproduction is authorized provided the source is acknowledged.
  10. ^ "Vocabria Product information". Union Register of medicinal products. Archived from the original on 5 March 2023. Retrieved 3 March 2023.
  11. ^ a b "Apretude EPAR". European Medicines Agency. 20 September 2023. Archived from the original on 6 October 2023. Retrieved 20 September 2023.
  12. ^ "Apretude Product information". Union Register of medicinal products. 20 September 2023. Archived from the original on 6 October 2023. Retrieved 1 October 2023.
  13. ^ Cite error: The named reference EPAR was invoked but never defined (see the help page).
  14. ^ Borrell B (March 2014). "Long-acting shot prevents infection with HIV analogue". Nature News. doi:10.1038/nature.2014.14819. S2CID 184399045.
  15. ^ "FDA Approves First Injectable Treatment for HIV Pre-Exposure Prevention". U.S. Food and Drug Administration (FDA) (Press release). 20 December 2021. Archived from the original on 22 April 2022. Retrieved 21 December 2021. This article incorporates text from this source, which is in the public domain.
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