Details of the Drug-Related molecule(s) Interaction Atlas

General Information of Drug (ID: DMGV8QU)

Drug Name

Etravirine Drug Info

Synonyms

Intelence; DAPY deriv; Diaminopyrimidine deriv; R 165335; R165335; TMC 125; TMC125; Intelence (TN); Intelence(TM); R-165335; R165335-TMC125; TMC-125; Etravirine (JAN/USAN/INN); TMC-125/R-165335; 4-((6-amino-5-bromo-2-((4-cyanophenyl)amino)-4-pyrimidinyl)oxy)-3,5-dimethyl-benzonitrile; 4-({6-AMINO-5-BROMO-2-[(4-CYANOPHENYL)AMINO]PYRIMIDIN-4-YL}OXY)-3,5-DIMETHYLBENZONITRILE; 4-[6-amino-5-bromo-2-(4-cyanoanilino)pyrimidin-4-yl]oxy-3,5-dimethylbenzonitrile; 65B; ETR

Indication

Disease Entry	ICD 11	Status	REF
Human immunodeficiency virus-1 infection	1C62	Approved	[1]

Cross-matching ID

PubChem CID: 193962
ChEBI ID: CHEBI:63589
CAS Number: CAS 269055-15-4
TTD Drug ID: DMGV8QU
VARIDT Drug ID: DR00597
INTEDE Drug ID: DR0671
ACDINA Drug ID: D00259

Molecule-Related Drug Atlas

Molecule Type:

DTT

DTP

DME

Drug Status:

Approved Drug(s)

Download the Complete Related Drug List

Drug(s) Targeting Human immunodeficiency virus Reverse transcriptase (HIV RT)

Drug Name	Drug ID	Indication	ICD 11	Highest Status	REF
Zidovudine	DM4KI7O	Human immunodeficiency virus infection	1C62	Approved	[6]
Nevirapine	DM6HX9B	Human immunodeficiency virus infection	1C62	Approved	[7]
Zalcitabine	DMH7MUV	Human immunodeficiency virus infection	1C62	Approved	[8]
Tenofovir	DM1IS6U	Chronic hepatitis B virus infection		Approved	[6]
Lamivudine	DMI347A	Chronic HBV infection	1E51.0Z	Approved	[9]
Abacavir	DMMN36E	Human immunodeficiency virus infection	1C62	Approved	[10]
Delavirdine	DM3NF5G	Human immunodeficiency virus infection	1C62	Approved	[9]
Efavirenz	DMC0GSJ	Human immunodeficiency virus infection	1C62	Approved	[9]
Rilpivirine	DMJ0QOW	Human immunodeficiency virus infection	1C62	Approved	[1]
MK-1439	DM215WE	Human immunodeficiency virus infection	1C62	Approved	[11]
------------------------------------------------------------------------------------


⏷ Show the Full List of 10 Drug(s)

Drug(s) Transported By Multidrug resistance-associated protein 3 (ABCC3)

Drug Name	Drug ID	Indication	ICD 11	Highest Status	REF
Methotrexate	DM2TEOL	Anterior urethra cancer		Approved	[12]
Folic Acid	DMEMBJC	Colorectal carcinoma		Approved	[13]
Fluorouracil	DMUM7HZ	Adenocarcinoma	2D40	Approved	[14]
Etoposide	DMNH3PG	Acute myelogenous leukaemia	2A41	Approved	[15]
Ezetimibe	DM7A8TW	Atherosclerosis	BD40	Approved	[16]
Glibenclamide	DM8JXPZ	Diabetic complication	5A2Y	Approved	[17]
Morphine	DMRMS0L	Advanced cancer	2A00-2F9Z	Approved	[18]
Cefadroxil	DMMC345	Bacterial infection	1A00-1C4Z	Approved	[19]
Teniposide	DMLW57T	Acute lymphoblastic leukaemia	2A85	Approved	[20]
Fexofenadine	DM17ONX	Allergic rhinitis	CA08.0	Approved	[21]
------------------------------------------------------------------------------------


⏷ Show the Full List of 10 Drug(s)

Drug(s) Metabolized By Cytochrome P450 3A4 (CYP3A4)

Drug Name	Drug ID	Indication	ICD 11	Highest Status	REF
Doxorubicin	DMVP5YE	Acute myelogenous leukaemia	2A41	Approved	[22]
Progesterone	DMUY35B	Amenorrhea	GA20.0	Approved	[23]
Tamoxifen	DMLB0EZ	Breast cancer	2C60-2C65	Approved	[24]
Estradiol	DMUNTE3	Acne vulgaris	ED80	Approved	[25]
Acetaminophen	DMUIE76	Allergic rhinitis	CA08.0	Approved	[26]
Imatinib	DM7RJXL	Acute lymphoblastic leukaemia	2A85	Approved	[27]
Etoposide	DMNH3PG	Acute myelogenous leukaemia	2A41	Approved	[28]
Zidovudine	DM4KI7O	Human immunodeficiency virus infection	1C62	Approved	[29]
Prasterone	DM67VKL	Chronic obstructive pulmonary disease	CA22	Approved	[23]
Verapamil	DMA7PEW	Angina pectoris	BA40	Approved	[30]
------------------------------------------------------------------------------------


⏷ Show the Full List of 10 Drug(s)

Drug(s) Metabolized By Cytochrome P450 2C9 (CYP2C9)

Drug Name	Drug ID	Indication	ICD 11	Highest Status	REF
Progesterone	DMUY35B	Amenorrhea	GA20.0	Approved	[31]
Tamoxifen	DMLB0EZ	Breast cancer	2C60-2C65	Approved	[32]
Estradiol	DMUNTE3	Acne vulgaris	ED80	Approved	[33]
Acetaminophen	DMUIE76	Allergic rhinitis	CA08.0	Approved	[34]
Imatinib	DM7RJXL	Acute lymphoblastic leukaemia	2A85	Approved	[35]
Zidovudine	DM4KI7O	Human immunodeficiency virus infection	1C62	Approved	[34]
Verapamil	DMA7PEW	Angina pectoris	BA40	Approved	[36]
Diclofenac	DMPIHLS	Chronic renal failure	GB61.Z	Approved	[37]
Estrone	DM5T6US	Acne vulgaris	ED80	Approved	[38]
Valproate	DMCFE9I	Epilepsy	8A60-8A68	Approved	[39]
------------------------------------------------------------------------------------


⏷ Show the Full List of 10 Drug(s)

Drug(s) Metabolized By Mephenytoin 4-hydroxylase (CYP2C19)

Drug Name	Drug ID	Indication	ICD 11	Highest Status	REF
Amoxicillin	DMUYNEI	Acute otitis media	AB00	Approved	[40]
Progesterone	DMUY35B	Amenorrhea	GA20.0	Approved	[31]
Tamoxifen	DMLB0EZ	Breast cancer	2C60-2C65	Approved	[41]
Estradiol	DMUNTE3	Acne vulgaris	ED80	Approved	[42]
Zidovudine	DM4KI7O	Human immunodeficiency virus infection	1C62	Approved	[34]
Verapamil	DMA7PEW	Angina pectoris	BA40	Approved	[43]
Diclofenac	DMPIHLS	Chronic renal failure	GB61.Z	Approved	[44]
Valproate	DMCFE9I	Epilepsy	8A60-8A68	Approved	[39]
Quinine	DMSWYF5	Malaria	1F40-1F45	Approved	[45]
Propofol	DMB4OLE	Anaesthesia	9A78.6	Approved	[46]
------------------------------------------------------------------------------------


⏷ Show the Full List of 10 Drug(s)

Molecular Interaction Atlas of This Drug

Molecular Interaction Atlas

Download the Complete Interaction Atlas for Visualization in Cytoscape

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Human immunodeficiency virus Reverse transcriptase (HIV RT)	TT84ETX	POL_HV1B1	Modulator	[2]

------------------------------------------------------------------------------------

Drug Transporter (DTP)

DTP Name	DTP ID	UniProt ID	MOA	REF
Multidrug resistance-associated protein 3 (ABCC3)	DTQ3ZHF	MRP3_HUMAN	Substrate	[3]

------------------------------------------------------------------------------------

Drug-Metabolizing Enzyme (DME)

DME Name	DME ID	UniProt ID	MOA	REF
Cytochrome P450 3A4 (CYP3A4)^{Main DME}	DE4LYSA	CP3A4_HUMAN	Substrate	[4]
Cytochrome P450 2C9 (CYP2C9)^{Main DME}	DE5IED8	CP2C9_HUMAN	Substrate	[4]
Mephenytoin 4-hydroxylase (CYP2C19)^{Main DME}	DEGTFWK	CP2CJ_HUMAN	Substrate	[5]

------------------------------------------------------------------------------------

References

1	Emerging antiviral drugs. Expert Opin Emerg Drugs. 2008 Sep;13(3):393-416.
2	2008 FDA drug approvals. Nat Rev Drug Discov. 2009 Feb;8(2):93-6.
3	Interaction potential of etravirine with drug transporters assessed in vitro. Antimicrob Agents Chemother. 2011 Mar;55(3):1282-4.
4	Pharmacokinetic interactions between etravirine and non-antiretroviral drugs. Clin Pharmacokinet. 2011 Jan;50(1):25-39.
5	Biotransformation of the antiretroviral drug etravirine: metabolite identification, reaction phenotyping, and characterization of autoinduction of cytochrome P450-dependent metabolism. Drug Metab Dispos. 2012 Apr;40(4):803-14.
6	Antiviral drugs in current clinical use. J Clin Virol. 2004 Jun;30(2):115-33.
7	HIV-1 reverse transcriptase complex with DNA and nevirapine reveals non-nucleoside inhibition mechanism.Nat Struct Mol Biol.2012 Jan 22;19(2):253-9.
8	A peptide inhibitor of HIV-1 reverse transcriptase using alpha,beta-dehydro residues: a structure-based computer model. J Biomol Struct Dyn. 1998 Oct;16(2):347-54.
9	Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services.
10	Quadruple nucleos(t)ide reverse transcriptase inhibitors-only regimen of tenofovir plus zidovudine/lamivudine/abacavir in heavily pre-treated HIV-1 infected patients: salvage therapy or backbone only Curr HIV Res. 2009 May;7(3):320-6.
11	2018 FDA drug approvals.Nat Rev Drug Discov. 2019 Feb;18(2):85-89.
12	Multidrug resistance protein (MRP) 1 and MRP3 attenuate cytotoxic and transactivating effects of the cyclopentenone prostaglandin, 15-deoxy-Delta(12,14)prostaglandin J2 in MCF7 breast cancer cells. Biochemistry. 2003 May 13;42(18):5429-37.
13	Transport of methotrexate (MTX) and folates by multidrug resistance protein (MRP) 3 and MRP1: effect of polyglutamylation on MTX transport. Cancer Res. 2001 Oct 1;61(19):7225-32.
14	ATP-binding cassette C transporters in human pancreatic carcinoma cell lines. Upregulation in 5-fluorouracil-resistant cells. Pancreatology. 2009;9(1-2):136-44.
15	Functional reconstitution of human ABCC3 into proteoliposomes reveals a transport mechanism with positive cooperativity. Biochemistry. 2009 May 26;48(20):4423-30.
16	Complex pharmacokinetic behavior of ezetimibe depends on abcc2, abcc3, and abcg2. Drug Metab Dispos. 2009 Aug;37(8):1698-702.
17	Transport of glyburide by placental ABC transporters: implications in fetal drug exposure. Placenta. 2006 Nov-Dec;27(11-12):1096-102.
18	Multidrug resistance-associated proteins 3, 4, and 5. Pflugers Arch. 2007 Feb;453(5):661-73.
19	Oral availability of cefadroxil depends on ABCC3 and ABCC4. Drug Metab Dispos. 2012 Mar;40(3):515-21.
20	Characterization of drug transport by the human multidrug resistance protein 3 (ABCC3). J Biol Chem. 2001 Dec 7;276(49):46400-7.
21	Involvement of multiple efflux transporters in hepatic disposition of fexofenadine. Mol Pharmacol. 2008 May;73(5):1474-83.
22	Expression levels and activation of a PXR variant are directly related to drug resistance in osteosarcoma cell lines. Cancer. 2007 Mar 1;109(5):957-65.
23	Contribution of human hepatic cytochrome P450 isoforms to regioselective hydroxylation of steroid hormones. Xenobiotica. 1998 Jun;28(6):539-47.
24	Comprehensive evaluation of tamoxifen sequential biotransformation by the human cytochrome P450 system in vitro: prominent roles for CYP3A and CYP2D6. J Pharmacol Exp Ther. 2004 Sep;310(3):1062-75.
25	Isoform-specific regulation of cytochromes P450 expression by estradiol and progesterone. Drug Metab Dispos. 2013 Feb;41(2):263-9.
26	Metabolic interactions between acetaminophen (paracetamol) and two flavonoids, luteolin and quercetin, through in-vitro inhibition studies. J Pharm Pharmacol. 2017 Dec;69(12):1762-1772.
27	Potent mechanism-based inhibition of CYP3A4 by imatinib explains its liability to interact with CYP3A4 substrates. Br J Pharmacol. 2012 Apr;165(8):2787-98.
28	Effects of morin on the pharmacokinetics of etoposide in rats. Biopharm Drug Dispos. 2007 Apr;28(3):151-6.
29	The metabolism of zidovudine by human liver microsomes in vitro: formation of 3'-amino-3'-deoxythymidine. Biochem Pharmacol. 1994 Jul 19;48(2):267-76.
30	Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675.
31	Progesterone and testosterone hydroxylation by cytochromes P450 2C19, 2C9, and 3A4 in human liver microsomes. Arch Biochem Biophys. 1997 Oct 1;346(1):161-9.
32	Tamoxifen inhibits cytochrome P450 2C9 activity in breast cancer patients. J Chemother. 2006 Aug;18(4):421-4.
33	Characterization of the oxidative metabolites of 17beta-estradiol and estrone formed by 15 selectively expressed human cytochrome p450 isoforms. Endocrinology. 2003 Aug;144(8):3382-98.
34	Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448.
35	Drug-drug interactions with imatinib: an observational study. Medicine (Baltimore). 2016 Oct;95(40):e5076.
36	Drug interactions with calcium channel blockers: possible involvement of metabolite-intermediate complexation with CYP3A. Drug Metab Dispos. 2000 Feb;28(2):125-30.
37	New insights into the structural features and functional relevance of human cytochrome P450 2C9. Part I. Curr Drug Metab. 2009 Dec;10(10):1075-126.
38	A potential role for the estrogen-metabolizing cytochrome P450 enzymes in human breast carcinogenesis. Breast Cancer Res Treat. 2003 Dec;82(3):191-7.
39	A mechanistic approach to antiepileptic drug interactions. Ann Pharmacother. 1998 May;32(5):554-63.
40	High-dose rabeprazole/amoxicillin therapy as the second-line regimen after failure to eradicate H. pylori by triple therapy with the usual doses of a proton pump inhibitor, clarithromycin and amoxicillin. Hepatogastroenterology. 2003 Nov-Dec;50(54):2274-8.
41	Cytochrome P450 pharmacogenetics and cancer. Oncogene. 2006 Mar 13;25(11):1679-91.
42	CYP2C19*17 is associated with decreased breast cancer risk. Breast Cancer Res Treat. 2009 May;115(2):391-6.
43	Cytochromes of the P450 2C subfamily are the major enzymes involved in the O-demethylation of verapamil in humans. Naunyn Schmiedebergs Arch Pharmacol. 1995 Dec;353(1):116-21.
44	Diclofenac and its derivatives as tools for studying human cytochromes P450 active sites: particular efficiency and regioselectivity of P450 2Cs. Biochemistry. 1999 Oct 26;38(43):14264-70.
45	Organic anion-transporting polypeptide B (OATP-B) and its functional comparison with three other OATPs of human liver. Gastroenterology. 2001 Feb;120(2):525-33.
46	Possible involvement of multiple human cytochrome P450 isoforms in the liver metabolism of propofol. Br J Anaesth. 1998 Jun;80(6):788-95.