Raltegravir

Raltegravir
Clinical data
Pronunciation	/rælˈtɛɡrəvɪər/; ral-TEG-rə-veer
Trade names	Isentress
Other names	RAL
AHFS/Drugs.com	Monograph
MedlinePlus	a608004
License data	US DailyMed: Raltegravir;
Pregnancy; category	AU: B3;
Routes of; administration	By mouth
ATC code	J05AJ01 (WHO) ;
Legal status
Legal status	CA: ℞-only; UK: POM (Prescription only); US: ℞-only; EU: Rx-only;
Pharmacokinetic data
Bioavailability	60% (FDA)
Protein binding	83%
Metabolism	Liver (UGT1A1)
Elimination half-life	9 hours
Excretion	feces 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 ;
PubChem CID	54671008;
DrugBank	DB06817;
ChemSpider	16445111 ;
UNII	22VKV8053U;
KEGG	D06676; as salt: D07133;
ChEBI	CHEBI:82960;
ChEMBL	ChEMBL254316 ;
NIAID ChemDB	471309;
PDB ligand	RLT (PDBe, RCSB PDB);
CompTox Dashboard (EPA)	DTXSID2048660 ;
ECHA InfoCard	100.124.631
Chemical and physical data
Formula	C20H21FN6O5
Molar mass	444.423 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) ; Key:CZFFBEXEKNGXKS-UHFFFAOYSA-N ;

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]

^ "Product monograph brand safety updates". Health Canada. 7 July 2016. Retrieved 1 April 2024.
^ "Isentress 400 mg Film-coated Tablets - Summary of Product Characteristics (SmPC)". (emc). Retrieved 11 July 2021.
^ "Isentress- raltegravir tablet, film coated Isentress- raltegravir tablet, chewable Isentress- raltegravir granule, for suspension". DailyMed. Retrieved 11 July 2021.
^ "Isentress EPAR". European Medicines Agency (EMA). 17 September 2018. Retrieved 12 July 2021.
^ ^a ^b British national formulary : BNF 69 (69 ed.). British Medical Association. 2015. p. 429. ISBN 978-0-85711-156-2.
^ ^a ^b ^c ^d ^e ^f ^g "Raltegravir Potassium". The American Society of Health-System Pharmacists. Retrieved 8 December 2017.
^ 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.