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Raltegravir information


Raltegravir
2
Clinical data
Trade namesIsentress
Other namesRAL
AHFS/Drugs.comMonograph
MedlinePlusa608004
License data
  • US DailyMed: Raltegravir
Pregnancy
category
  • AU: B3
Routes of
administration
By mouth
ATC code
  • J05AJ01 (WHO)
Legal status
Legal status
  • CA: ℞-only[1]
  • UK: POM (Prescription only)[2]
  • US: ℞-only[3]
  • EU: Rx-only[4]
Pharmacokinetic data
Bioavailability60% (FDA)
Protein binding83%
MetabolismLiver (UGT1A1)
Elimination half-life9 hours
Excretionfeces and urine
Identifiers
IUPAC name
  • N-(4-Fluorobenzyl)-5-hydroxy-1-methyl-2-(2-{[(5-methyl-1,3,4-oxadiazol-2-yl)carbonyl]amino}-2-propanyl)-6-oxo-1,6-dihydro-4-pyrimidinecarboxamide
CAS Number
  • 518048-05-0 checkY
PubChem CID
  • 54671008
DrugBank
  • DB06817
ChemSpider
  • 16445111 checkY
UNII
  • 22VKV8053U
KEGG
  • D06676
  • as salt: D07133
ChEBI
  • CHEBI:82960
ChEMBL
  • ChEMBL254316 checkY
NIAID ChemDB
  • 471309
PDB ligand
  • RLT (PDBe, RCSB PDB)
CompTox Dashboard (EPA)
  • DTXSID2048660 Edit this at Wikidata
ECHA InfoCard100.124.631 Edit this at Wikidata
Chemical and physical data
FormulaC20H21FN6O5
Molar mass444.423 g·mol−1
3D model (JSmol)
  • Interactive image
SMILES
  • Cc1nnc(o1)C(=O)NC(C)(C)C\3=N\C(C(=O)NCc2ccc(F)cc2)=C(\O)C(=O)N/3C
InChI
  • InChI=1S/C20H21FN6O5/c1-10-25-26-17(32-10)16(30)24-20(2,3)19-23-13(14(28)18(31)27(19)4)15(29)22-9-11-5-7-12(21)8-6-11/h5-8,28H,9H2,1-4H3,(H,22,29)(H,24,30) checkY
  • Key:CZFFBEXEKNGXKS-UHFFFAOYSA-N checkY

Raltegravir, sold under the brand name Isentress, is an antiretroviral medication used, together with other medication, to treat HIV/AIDS.[5] It may also be used, as part of post exposure prophylaxis, to prevent HIV infection following potential exposure.[6] It is taken by mouth.[5]

Common side effects include trouble sleeping, feeling tired, nausea, high blood sugar, and headaches.[6] Severe side effects may include allergic reactions including Stevens–Johnson syndrome, muscle breakdown, and liver problems.[6] It is unclear if use during pregnancy or breastfeeding is safe.[6] Raltegravir is an HIV integrase strand transfer inhibitor which blocks the functioning of HIV integrase which is needed for viral replication.[6]

Raltegravir was approved for medical use in the United States in 2007.[6] It is on the World Health Organization's List of Essential Medicines.[7] Lamivudine/raltegravir, a combination with lamivudine, is also available.[6]

  1. ^ "Product monograph brand safety updates". Health Canada. 7 July 2016. Retrieved 1 April 2024.
  2. ^ "Isentress 400 mg Film-coated Tablets - Summary of Product Characteristics (SmPC)". (emc). Retrieved 11 July 2021.
  3. ^ "Isentress- raltegravir tablet, film coated Isentress- raltegravir tablet, chewable Isentress- raltegravir granule, for suspension". DailyMed. Retrieved 11 July 2021.
  4. ^ "Isentress EPAR". European Medicines Agency (EMA). 17 September 2018. Retrieved 12 July 2021.
  5. ^ a b British national formulary : BNF 69 (69 ed.). British Medical Association. 2015. p. 429. ISBN 978-0-85711-156-2.
  6. ^ a b c d e f g "Raltegravir Potassium". The American Society of Health-System Pharmacists. Retrieved 8 December 2017.
  7. ^ World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.

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