Dolutegravir

Dolutegravir
Clinical data
Trade names	Tivicay, Tivicay PD
Other names	GSK572, S-349572
AHFS/Drugs.com	Monograph
MedlinePlus	a613043
License data	US DailyMed: Dolutegravir;
Pregnancy; category	AU: B1;
Routes of; administration	By mouth
ATC code	J05AJ03 (WHO) J05AR13 (WHO) J05AR21 (WHO);
Legal status
Legal status	AU: S4 (Prescription only); CA: ℞-only; UK: POM (Prescription only); US: ℞-only; EU: Rx-only; In general: ℞ (Prescription only);
Pharmacokinetic data
Bioavailability	n/a
Protein binding	≥98.9%
Metabolism	UGT1A1 and CYP3A
Elimination half-life	~14 hours
Excretion	Feces (53%) and urine (18.9%)
Identifiers
	IUPAC name (4R,12aS)-N-(2,4-difluorobenzyl)-7-hydroxy-4-methyl-6,8-dioxo-3,4,6,8,12,12a-hexahydro-2H-pyrido[1',2':4,5]pyrazino[2,1-b] [1,3]oxazine-9-carboxamide;
CAS Number	1051375-16-6 ;
PubChem CID	54726191;
IUPHAR/BPS	7365;
DrugBank	DB08930;
ChemSpider	25051637 ;
UNII	DKO1W9H7M1;
KEGG	D10066;
ChEBI	CHEBI:76010;
ChEMBL	ChEMBL1229211 ;
PDB ligand	DLU (PDBe, RCSB PDB);
CompTox Dashboard (EPA)	DTXSID90909356 ;
ECHA InfoCard	100.237.735
Chemical and physical data
Formula	C20H19F2N3O5
Molar mass	419.385 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C[C@@H]1CCO[C@@H]2N1C(=O)c3c(c(=O)c(cn3C2)C(=O)NCc4ccc(cc4F)F)O;
	InChI InChI=1S/C20H19F2N3O5/c1-10-4-5-30-15-9-24-8-13(17(26)18(27)16(24)20(29)25(10)15)19(28)23-7-11-2-3-12(21)6-14(11)22/h2-3,6,8,10,15,27H,4-5,7,9H2,1H3,(H,23,28)/t10-,15+/m1/s1 ; Key:RHWKPHLQXYSBKR-BMIGLBTASA-N ;
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Dolutegravir (DTG), sold under the brand name Tivicay, is an antiretroviral medication used, together with other medication, to treat HIV/AIDS. It may also be used, as part of post exposure prophylaxis, to prevent HIV infection following potential exposure. It is taken by mouth.

Common side effects include trouble sleeping, feeling tired, diarrhea, high blood sugar, and headache. Severe side effects may include allergic reactions and liver problems. Concerns that usage during pregnancy can result in harm to the baby have been refuted by further studies that show there is no statistical difference in neural tube defects from the usage of dolutegravir compared to other antiretrovirals. It is unclear if use during breastfeeding is safe. Dolutegravir is an HIV integrase strand transfer inhibitor which blocks the functioning of HIV integrase which is needed for viral replication.

Dolutegravir was approved for medical use in the United States in 2013. It is on the World Health Organization's List of Essential Medicines. Abacavir/dolutegravir/lamivudine, a combination with abacavir and lamivudine is also available. As of 2019, the World Health Organization (WHO) recommends DTG as the first- and second-line treatment for all persons with HIV.