Details of Drug

Drug General Information (ID: D0515)
Drug Name	Dolutegravir
Drug Type	Small molecule
Drug Synonymous	1051375-16-6; GSK1349572; Tivicay; S/GSK1349572; Dolutegravir (GSK1349572); S-349572; GSK-1349572; GSK 1349572; UNII-DKO1W9H7M1; (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; CHEBI:76010; DKO1W9H7M1; Tivicay (TN); (4R,12aS)-N-[(2,4-Difluorophenyl)methyl]-3,4,6,8,12,12a-hexahydro-7-hydroxy-4-methyl-6,8-dioxo-2H-pyrido[1',2':4,5]pyrazino[2,1-b][1,3]oxazine-9-carboxamide; Dolutegravir Sodium ( Click to Show/Hide
Disease Class	1C60-1C62: Human immunodeficiency virus disease
Therapeutic Class	Antiviral Agents
Structure
Structure	3D Structure		2D Structure
Formula	C20H19F2N3O5
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
InChIKey	RHWKPHLQXYSBKR-BMIGLBTASA-N
Canonical SMILES	CC1CCOC2N1C(=O)C3=C(C(=O)C(=CN3C2)C(=O)NCC4=C(C=C(C=C4)F)F)O
External Link
	Pubchem ID	54726191
	CAS Number	1051375-16-6
	CHEBI ID	76010
	TTD ID	D00YZD
	VARIDT ID	DR00383

Drug-Drug Interaction Network
Sunburst Graph		Legend Information AM001 Affected gastrointestinal absorption AM002 Affected cellular transport AM004 Affected intra/extra-hepatic metabolism BM003 Complex formation BM009 Altered absorption (Unspecific) BM010 Transporter inhibition BM017 CYP450 enzyme inhibition BM019 UGT inhibition BM022 CYP450 enzyme induction BM023 UGT induction
Relation Graph

Full list of drugs interacting with Dolutegravir
Affected gastrointestinal absorption
	Complex formation					Drug Num: 31
Drug ID		Drug Name	Formula	Pubchem ID	Severity Level		Interaction Detail	REF
D0049		Aluminum hydroxide	AlH3O3	10176082	Major		Inter Info	[1]
D0125		Attapulgite	Al2H29Mg2O15Si4-	56842194	Major		Inter Info	[1]
D0235		Calcium acetate	C4H6CaO4	6116	Major		Inter Info	[1]
D0236		Calcium carbonate	CCaO3	10112	Major		Inter Info	[1]
D0483		Didanosine	C10H12N4O3	135398739	Major		Inter Info	[1], [6]
D0238		Calcium citrate	C12H10Ca3O14	13136	Major		Inter Info	[1]
D0239		Calcium glubionate anhydrous	C18H32CaO19	64776	Major		Inter Info	[1], [8]
D0241		Calcium gluconate	C12H22CaO14	9290	Major		Inter Info	[1]
D0242		Calcium glycerophosphate	C3H7CaO6P	120096	Major		Inter Info	[1]
D0243		Calcium lactate	C6H10CaO6	13144	Major		Inter Info	[1]
D0244		Calcium Phosphate	Ca3O8P2	24456	Major		Inter Info	[1], [8]
D0649		Ferrous fumarate	C4H2FeO4	6433164	Major		Inter Info	[1]
D0650		Ferrous gluconate	C12H22FeO14	23616740	Major		Inter Info	[1]
D0651		Ferrous sulfate anhydrous	FeO4S	24393	Major		Inter Info	[1], [8]
D0849		Iron protein succinylate	NA	NA	Major		Inter Info	[1]
D0967		Magaldrate	AlHMgO5S+2	3086011	Major		Inter Info	[1]
D0968		Magnesium carbonate	CMgO3	11029	Major		Inter Info	[1]
D0969		Magnesium chloride	Cl2H12MgO6	643991	Major		Inter Info	[1]
D0970		Magnesium citrate	C12H10Mg3O14	6099959	Major		Inter Info	[1]
D0971		Magnesium gluconate	C12H22MgO14	11418570	Major		Inter Info	[1]
D0972		Magnesium glycinate	C4H8MgN2O4	84645	Major		Inter Info	[1]
D0973		Magnesium hydroxide	H2MgO2	14791	Major		Inter Info	[1]
D1566		Tetraferric tricitrate decahydrate	C18H32Fe4O31	90478690	Major		Inter Info	[1], [8]
D1724		Zinc gluconate	C12H22O14Zn	443445	Major		Inter Info	[9], [1], [10]
D1725		Zinc sulfate	O4SZn	24424	Major		Inter Info	[9], [1], [10]
D0847		Iron	Fe	23925	Major		Inter Info	[1], [8]
D0877		Kaolin	Al2H4O9Si2	56841936	Major		Inter Info	[1]
D0974		Magnesium oxide	MgO	14792	Major		Inter Info	[1]
D0975		Magnesium sulfate	MgO4S	24083	Major		Inter Info	[1]
D1480		Sodium bicarbonate	CHNaO3	516892	Major		Inter Info	[1]
D1511		Sucralfate	C12H54Al9O55S8	121494085	Major		Inter Info	[1]
	Altered absorption (Unspecific)					Drug Num: 1
Drug ID		Drug Name	Formula	Pubchem ID	Severity Level		Interaction Detail	REF
D1187		Orlistat	C29H53NO5	3034010	Moderate		Inter Info	[14]
Affected cellular transport
	Transporter inhibition					Drug Num: 7
Drug ID		Drug Name	Formula	Pubchem ID	Severity Level		Interaction Detail	REF
D0513		Dofetilide	C19H27N3O5S2	71329	Major		Inter Info	[7], [1]
D0357		Clofarabine	C10H11ClFN5O3	119182	Moderate		Inter Info	[11], [1]
D0412		Dalfampridine	C5H6N2	1727	Moderate		Inter Info	[2], [12], [13]
D1591		Tipiracil	C9H11ClN4O2	6323266	Moderate		Inter Info	[11], [1]
D0745		Guanfacine	C9H9Cl2N3O	3519	Moderate		Inter Info	[11], [1]
D1015		Metformin	C4H11N5	4091	Moderate		Inter Info	[2], [3], [5]
D1919		Varenicline	C13H13N3	170361	Moderate		Inter Info	[11], [1]
Affected intra/extra-hepatic metabolism
	CYP450 enzyme inhibition					Drug Num: 50
Drug ID		Drug Name	Formula	Pubchem ID	Severity Level		Interaction Detail	REF
D0116		Atazanavir	C38H52N6O7	148192	Moderate		Inter Info	[1]
D0066		Amiodarone	C25H29I2NO3	2157	Minor		Inter Info	[1]
D0080		Amprenavir	C25H35N3O6S	65016	Minor		Inter Info	[1]
D0100		Aprepitant	C23H21F7N4O3	135413536	Minor		Inter Info	[1]
D0192		Boceprevir	C27H45N5O5	10324367	Minor		Inter Info	[1]
D0313		Chloramphenicol	C11H12Cl2N2O5	5959	Minor		Inter Info	[1]
D0337		Cimetidine	C10H16N6S	2756	Minor		Inter Info	[1]
D0341		Ciprofloxacin	C17H18FN3O3	2764	Minor		Inter Info	[1]
D0349		Clarithromycin	C38H69NO13	84029	Minor		Inter Info	[1]
D0367		Clotrimazole	C22H17ClN2	2812	Minor		Inter Info	[1]
D0386		Conivaptan	C32H26N4O2	151171	Minor		Inter Info	[1]
D0393		Crizotinib	C21H22Cl2FN5O	11626560	Minor		Inter Info	[1]
D0402		Cyclosporine	C62H111N11O12	5284373	Minor		Inter Info	[1]
D0413		Dalfopristin	C34H50N4O9S	6323289	Minor		Inter Info	[1]
D0416		Danazol	C22H27NO2	28417	Minor		Inter Info	[1]
D0428		Dasatinib	C22H26ClN7O2S	3062316	Minor		Inter Info	[1]
D0439		Delavirdine	C22H28N6O3S	5625	Minor		Inter Info	[1]
D0497		Diltiazem	C22H26N2O4S	39186	Minor		Inter Info	[1]
D0375		Cobicistat	C40H53N7O5S2	25151504	Minor		Inter Info	[1]
D0735		Goldenseal	NA	NA	Minor		Inter Info	[1]
D1505		Stiripentol	C14H18O3	5311454	Minor		Inter Info	[1]
D1653		Troleandomycin	C41H67NO15	202225	Minor		Inter Info	[1]
D0534		Dronedarone	C31H44N2O5S	208898	Minor		Inter Info	[1]
D0597		Erythromycin	C37H67NO13	12560	Minor		Inter Info	[1]
D0667		Fluconazole	C13H12F2N6O	3365	Minor		Inter Info	[1]
D0687		Fluvoxamine	C15H21F3N2O2	5324346	Minor		Inter Info	[1]
D0693		Fosaprepitant	C23H22F7N4O6P	135413538	Minor		Inter Info	[1]
D0740		Grepafloxacin	C19H22FN3O3	72474	Minor		Inter Info	[1]
D0793		Imatinib	C29H31N7O	5291	Minor		Inter Info	[1]
D0799		Indinavir	C36H47N5O4	5362440	Minor		Inter Info	[1]
D0858		Isoniazid	C6H7N3O	3767	Minor		Inter Info	[1]
D0867		Itraconazole	C35H38Cl2N8O4	55283	Minor		Inter Info	[1]
D0869		Ivacaftor	C24H28N2O3	16220172	Minor		Inter Info	[1]
D0880		Ketoconazole	C26H28Cl2N4O4	456201	Minor		Inter Info	[1]
D0944		Lomitapide	C39H37F6N3O2	9853053	Minor		Inter Info	[1]
D1057		Miconazole	C18H14Cl4N2O	4189	Minor		Inter Info	[1]
D1063		Mifepristone	C29H35NO2	55245	Minor		Inter Info	[1]
D1117		Nefazodone	C25H32ClN5O2	4449	Minor		Inter Info	[1]
D1119		Nelfinavir	C32H45N3O4S	64143	Minor		Inter Info	[1]
D1134		Nifedipine	C17H18N2O6	4485	Minor		Inter Info	[1]
D1136		Nilotinib	C28H22F3N7O	644241	Minor		Inter Info	[1]
D1315		Posaconazole	C37H42F2N8O4	468595	Minor		Inter Info	[1]
D1387		Regorafenib	C21H15ClF4N4O3	11167602	Minor		Inter Info	[1]
D1415		Ritonavir	C37H48N6O5S2	392622	Minor		Inter Info	[1]
D1444		Saquinavir	C38H50N6O5	441243	Minor		Inter Info	[1]
D1541		Telaprevir	C36H53N7O6	3010818	Minor		Inter Info	[1]
D1544		Telithromycin	C43H65N5O10	3002190	Minor		Inter Info	[1]
D1579		Ticagrelor	C23H28F2N6O4S	9871419	Minor		Inter Info	[1]
D1690		Verapamil	C27H38N2O4	2520	Minor		Inter Info	[1]
D1706		Voriconazole	C16H14F3N5O	71616	Minor		Inter Info	[1]
	UGT inhibition					Drug Num: 1
Drug ID		Drug Name	Formula	Pubchem ID	Severity Level		Interaction Detail	REF
D1497		Sorafenib	C21H16ClF3N4O3	216239	Minor		Inter Info	[1]
	CYP450 enzyme induction					Drug Num: 42
Drug ID		Drug Name	Formula	Pubchem ID	Severity Level		Interaction Detail	REF
D0255		Carbamazepine	C15H12N2O	2554	Major		Inter Info	[2], [3], [4], [1], [5]
D0095		Apalutamide	C21H15F4N5O2S	24872560	Major		Inter Info	[2], [3], [4], [1], [5]
D0554		Efavirenz	C14H9ClF3NO2	64139	Major		Inter Info	[4], [1], [5]
D0628		Etravirine	C20H15BrN6O	193962	Major		Inter Info	[2], [3], [4], [1], [5]
D0692		Fosamprenavir	C25H36N3O9PS	131536	Major		Inter Info	[1], [5]
D0697		Fosphenytoin	C16H15N2O6P	56339	Major		Inter Info	[2], [3], [4], [1], [5]
D1128		Nevirapine	C15H14N4O	4463	Major		Inter Info	[4], [1], [5]
D1198		Oxcarbazepine	C15H12N2O2	34312	Major		Inter Info	[2], [3], [4], [1], [5]
D1265		Phenobarbital	C12H12N2O3	4763	Major		Inter Info	[2], [3], [4], [1], [5]
D1283		Phenytoin	C15H12N2O2	1775	Major		Inter Info	[2], [3], [4], [1], [5]
D1340		Primidone	C12H14N2O2	4909	Major		Inter Info	[2], [3], [4], [1], [5]
D1400		Rifampicin	C43H58N4O12	135398735	Major		Inter Info	[4], [1], [5]
D1502		St. John's Wort	NA	NA	Major		Inter Info	[2], [3], [4], [1], [5]
D1592		Tipranavir	C31H33F3N2O5S	54682461	Major		Inter Info	[4], [1], [5]
D0061		Aminoglutethimide	C13H16N2O2	2145	Minor		Inter Info	[1]
D0106		Armodafinil	C15H15NO2S	9690109	Minor		Inter Info	[15], [16], [17], [18], [19]
D0178		Bexarotene	C24H28O2	82146	Minor		Inter Info	[1]
D0194		Bosentan	C27H29N5O6S	104865	Minor		Inter Info	[1]
D0224		Butabarbital	C10H16N2O3	2479	Minor		Inter Info	[1]
D0225		Butalbital	C11H16N2O3	2481	Minor		Inter Info	[1]
D0300		Cenobamate	C10H10ClN5O2	11962412	Minor		Inter Info	[1]
D0432		Deferasirox	C21H15N3O4	214348	Minor		Inter Info	[1]
D0453		Dexamethasone	C22H29FO5	5743	Minor		Inter Info	[1]
D0555		Elagolix	C32H30F5N3O5	11250647	Minor		Inter Info	[1]
D0872		Ivosidenib	C28H22ClF3N6O3	71657455	Minor		Inter Info	[1]
D0953		Lorlatinib	C21H19FN6O2	71731823	Minor		Inter Info	[1]
D1258		Pexidartinib	C20H15ClF3N5	25151352	Minor		Inter Info	[1]
D0578		Enzalutamide	C21H16F4N4O2S	15951529	Minor		Inter Info	[1]
D0639		Felbamate	C11H14N2O4	3331	Minor		Inter Info	[1]
D0741		Griseofulvin	C17H17ClO6	441140	Minor		Inter Info	[1]
D1040		Methylphenobarbital	C13H14N2O3	8271	Minor		Inter Info	[1], [20]
D1081		Modafinil	C15H15NO2S	4236	Minor		Inter Info	[15], [16], [17], [18], [19]
D1099		Nafcillin	C21H22N2O5S	8982	Minor		Inter Info	[1]
D1248		Pentobarbital	C11H18N2O3	4737	Minor		Inter Info	[1]
D1274		Phenylbutazone	C19H20N2O2	4781	Minor		Inter Info	[1]
D1399		Rifabutin	C46H62N4O11	135398743	Minor		Inter Info	[1]
D1401		Rifapentine	C47H64N4O12	135403821	Minor		Inter Info	[1]
D1433		Rufinamide	C10H8F2N4O	129228	Minor		Inter Info	[1]
D1453		Secobarbital	C12H18N2O3	5193	Minor		Inter Info	[1]
D1518		Sulfinpyrazone	C23H20N2O3S	5342	Minor		Inter Info	[1]
D1652		Troglitazone	C24H27NO5S	5591	Minor		Inter Info	[1]
D1687		Vemurafenib	C23H18ClF2N3O3S	42611257	Minor		Inter Info	[1]
	UGT induction					Drug Num: 1
Drug ID		Drug Name	Formula	Pubchem ID	Severity Level		Interaction Detail	REF
D0426		Darunavir	C27H37N3O7S	213039	Minor		Inter Info	[1]

References
1	Product Information. Tivicay (dolutegravir). ViiV Healthcare, Research Triangle Park, NC.
2	Cerner Multum, Inc. "Australian Product Information.".
3	Cerner Multum, Inc. "UK Summary of Product Characteristics.".
4	Product Information. Dovato (dolutegravir-lamivudine). ViiV Healthcare, Research Triangle Park, NC.
5	Product Information. Triumeq (abacavir/dolutegravir/lamiVUDine). ViiV Healthcare, Research Triangle Park, NC.
6	Product Information. Videx (didanosine). Bristol-Myers Squibb, Princeton, NJ.
7	Product Information. Tikosyn (dofetilide) Pfizer US Pharmaceuticals, Atlanta, GA.
8	Wohlt PD, Zheng L, Gunderson S, Balzar SA, Johnson BD, Fish JT "Recommendations for the use of medications with continuous enteral nutrition." Am J Health Syst Pharm 66 (2009): 1438-67. [PMID: 19667002]
9	Product Information. Biktarvy (bictegravir/emtricitabine/tenofovir). Gilead Sciences, Foster City, CA.
10	US National Library of Medicine "Guidelines for the use of antiretroviral agents in adults and adolescents with HIV.".
11	Product Information. Lonsurf (tipiracil-trifluridine). Taiho Oncology, Inc., Princeton, NJ.
12	EMEA. European Medicines Agency "EPARs. European Union Public Assessment Reports.".
13	Cerner Multum, Inc "ANVISA Bulario Eletrnico." .
14	MHRA. Medicines and Healthcare Products Regulatory Agency "Orlistat: theoretical interaction with antiretroviral HIV medicines.".
15	Doherty MM, Charman WN "The mucosa of the small intestine: how clinically relevant as an organ of drug metabolism?" Clin Pharmacokinet 41 (2002): 235-53. [PMID: 11978143]
16	Product Information. Nuvigil (armodafinil). Cephalon Inc, West Chester, PA.
17	Product Information. Provigil (modafinil). Cephalon, Inc, West Chester, PA.
18	Robertson P Jr, Hellriegel ET, Arora S, Nelson M "Effect of modafinil on the pharmacokinetics of ethinyl estradiol and triazolam in healthy volunteers." Clin Pharmacol Ther 71 (2002): 46-56. [PMID: 11823757]
19	Robertson P, Decory HH, Madan A, Parkinson A "In vitro inhibition and induction of human hepatic cytochrome P450 enzymes by modafinil." Drug Metab Dispos 28 (2000): 664-71. [PMID: 10820139]
20	Product Information. Turalio (pexidartinib). Daiichi Sankyo, Inc., Parsippany, NJ.

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