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

General Information of Drug (ID: DMH75KV)

Drug Name

Acenocoumarol Drug Info

Synonyms

Acenocoumarin; Acenocoumarolum; Acenocumarol; Acenocumarolo; Acenocumarolum; Acenokumarin; Ascumar; Minisintrom; Neositron;Nicoumalone; Nicumalon; Nitrovarfarian; Nitrowarfarin; Sincoumar; Sinkumar; Sinthrom; Sinthrome; Sintrom; Sintroma; Syncoumar; Syncumar; Synthrom; Syntrom; Zotil; Acenocoumarol Alliance Brand; Acenocoumarol Novartis Brand; Acenocoumarol [INN]; Acenocumarolo [DCIT]; Acenokumarin [Czech]; Alliance Brand of Acenocoumarol; Ciba Geigy Brand of Acenocoumarol; Mini Sintrom; Novartis Brand of Acenocoumarol; G 23350; Acenocoumarol (INN); Acenocoumarol Ciba-Geigy Brand; Acenocoumarolum [INN-Latin]; Ciba-Geigy Brand of Acenocoumarol; G-23350; Mini-sintrom; Sinthrome (TN); Sintrom (TN); AB-014/25000129; G-23,350; Mini-sintrom (TN); Nitrophenylacetylethyl-4-hydroxycoumarine; 2-hydroxy-3-[1-(4-nitrophenyl)-3-oxobutyl]-4h-chromen-4-one; 2-hydroxy-3-[1-(4-nitrophenyl)-3-oxobutyl]chromen-4-one; 3-(alpha-(4'-Nitrophenyl)-beta-acetylethyl)-4-hydroxycoumarin; 3-(alpha-(p-Nitrophenol)-beta-acetylethyl)-4-hydroxycoumarin; 3-(alpha-Acetonyl-4-nitrobenzyl)-4-hydroxycoumarin; 3-(alpha-Acetonyl-p-nitrobenzyl)-4-hydroxycoumarin; 3-(alpha-Acetonyl-para-nitrobenzyl)-4-hydroxy-coumarin; 3-(alpha-p-Nitrophenyl-beta-acetylethyl)-4-hydroxycoumarin; 4-Hydroxy-3-(1-(4-nitrophenyl)-3-oxobutyl)-2H-1-benzopyran-2-one;4-Hydroxy-3-[1-(4-nitrophenyl)-3-oxobutyl]-2H-chromen-2-one

Indication

Disease Entry	ICD 11	Status	REF
Thrombosis	DB61-GB90	Approved	[1]

Therapeutic Class

Anticoagulants

Cross-matching ID

PubChem CID: 54676537
ChEBI ID: CHEBI:53766
CAS Number: CAS 152-72-7
TTD Drug ID: DMH75KV
INTEDE Drug ID: DR0036

Molecule-Related Drug Atlas

Molecule Type:

DTT

DME

Drug Status:

Approved Drug(s)

Clinical Trial Drug(s)

Download the Complete Related Drug List

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

Drug Name	Drug ID	Indication	ICD 11	Highest Status	REF
Doxorubicin	DMVP5YE	Solid tumour/cancer	2A00-2F9Z	Approved	[8]
Progesterone	DMUY35B	Premature labour	JB00	Approved	[9]
Tamoxifen	DMLB0EZ	Breast cancer	2C60-2C65	Approved	[10]
Estradiol	DMUNTE3	Breast cancer	2C60-2C65	Approved	[11]
Acetaminophen	DMUIE76	Pain	MG30-MG3Z	Approved	[12]
Imatinib	DM7RJXL	Acute lymphoblastic leukaemia	2A85	Approved	[13]
Etoposide	DMNH3PG	Solid tumour/cancer	2A00-2F9Z	Approved	[14]
Zidovudine	DM4KI7O	Human immunodeficiency virus infection	1C62	Approved	[15]
Prasterone	DM67VKL	Chronic obstructive pulmonary disease	CA22	Approved	[9]
Verapamil	DMA7PEW	Hypertension	BA00-BA04	Approved	[7]
------------------------------------------------------------------------------------


⏷ Show the Full List of 10 Drug(s)

Drug(s) Metabolized By Cytochrome P450 1A2 (CYP1A2)

Drug Name	Drug ID	Indication	ICD 11	Highest Status	REF
Fluorouracil	DMUM7HZ	Solid tumour/cancer	2A00-2F9Z	Approved	[16]
Dinoprostone	DMTYOPD	Medical abortion	JA00.1Z	Approved	[17]
Tamoxifen	DMLB0EZ	Breast cancer	2C60-2C65	Approved	[18]
Estradiol	DMUNTE3	Breast cancer	2C60-2C65	Approved	[19]
Acetaminophen	DMUIE76	Pain	MG30-MG3Z	Approved	[20]
Imatinib	DM7RJXL	Acute lymphoblastic leukaemia	2A85	Approved	[21]
Etoposide	DMNH3PG	Solid tumour/cancer	2A00-2F9Z	Approved	[14]
Oxaliplatin	DMQNWRD	Colorectal cancer	2B91.Z	Approved	[22]
Verapamil	DMA7PEW	Hypertension	BA00-BA04	Approved	[23]
Diclofenac	DMPIHLS	Osteoarthritis	FA00-FA05	Approved	[24]
------------------------------------------------------------------------------------


⏷ 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	Premature labour	JB00	Approved	[25]
Tamoxifen	DMLB0EZ	Breast cancer	2C60-2C65	Approved	[26]
Estradiol	DMUNTE3	Breast cancer	2C60-2C65	Approved	[27]
Acetaminophen	DMUIE76	Pain	MG30-MG3Z	Approved	[28]
Imatinib	DM7RJXL	Acute lymphoblastic leukaemia	2A85	Approved	[29]
Zidovudine	DM4KI7O	Human immunodeficiency virus infection	1C62	Approved	[28]
Verapamil	DMA7PEW	Hypertension	BA00-BA04	Approved	[30]
Diclofenac	DMPIHLS	Osteoarthritis	FA00-FA05	Approved	[31]
Estrone	DM5T6US	Menopausal and postmenopausal disorder	GA30	Approved	[32]
Valproate	DMCFE9I	Epilepsy	8A60-8A68	Approved	[33]
------------------------------------------------------------------------------------


⏷ 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	Bacterial infection	1A00-1C4Z	Approved	[34]
Progesterone	DMUY35B	Premature labour	JB00	Approved	[25]
Tamoxifen	DMLB0EZ	Breast cancer	2C60-2C65	Approved	[35]
Estradiol	DMUNTE3	Breast cancer	2C60-2C65	Approved	[36]
Zidovudine	DM4KI7O	Human immunodeficiency virus infection	1C62	Approved	[28]
Verapamil	DMA7PEW	Hypertension	BA00-BA04	Approved	[37]
Diclofenac	DMPIHLS	Osteoarthritis	FA00-FA05	Approved	[38]
Valproate	DMCFE9I	Epilepsy	8A60-8A68	Approved	[33]
Quinine	DMSWYF5	Malaria	1F40-1F45	Approved	[39]
Propofol	DMB4OLE	Anaesthesia	9A78.6	Approved	[40]
------------------------------------------------------------------------------------


⏷ Show the Full List of 10 Drug(s)

Drug(s) Targeting Vitamin K epoxide reductase complex 1 (VKORC1)

Drug Name	Drug ID	Indication	ICD 11	Highest Status	REF
Warfarin	DMJYCVW	Atrial fibrillation	BC81.3	Approved	[4]
Phenprocoumon	DMDO279	Thrombosis	DB61-GB90	Approved	[4]
Dicumarol	DMFQCB1	Bleeding disorder	GA20-GA21	Approved	[41]
Phenindione	DM2PYNR	Coagulation defect	3B10.0	Approved	[4]
Tecarfarin	DMTCR2O	Cerebrovascular ischaemia	8B1Z	Phase 3	[42]
------------------------------------------------------------------------------------

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
Vitamin K epoxide reductase complex 1 (VKORC1)	TTEUC8H	VKOR1_HUMAN	Inhibitor	[2] , [3] , [4]

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

Drug-Metabolizing Enzyme (DME)

DME Name	DME ID	UniProt ID	MOA	REF
Cytochrome P450 3A4 (CYP3A4)	DE4LYSA	CP3A4_HUMAN	Substrate	[5]
Cytochrome P450 2C9 (CYP2C9)	DE5IED8	CP2C9_HUMAN	Substrate	[6]
Mephenytoin 4-hydroxylase (CYP2C19)	DEGTFWK	CP2CJ_HUMAN	Substrate	[7]
Cytochrome P450 1A2 (CYP1A2)	DEJGDUW	CP1A2_HUMAN	Substrate	[7]

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

References

1	Drug information of Acenocoumarol, 2008. eduDrugs.
2	Evaluation of a reverse-hybridization StripAssay for the detection of genetic polymorphisms leading to acenocoumarol sensitivity. Mol Biol Rep. 2010 Apr;37(4):1693-7.
3	Genotypes associated with reduced activity of VKORC1 and CYP2C9 and their modification of acenocoumarol anticoagulation during the initial treatmen... Clin Pharmacol Ther. 2009 Apr;85(4):379-86.
4	[Oral anticoagulation and pharmacogenetics: importance in the clinical setting]. Rev Med Suisse. 2007 Sep 12;3(124):2030, 2033-4, 2036.
5	Possible interaction between topical terbinafine and acenocoumarol. Ann Pharmacother. 2009 Nov;43(11):1911-2.
6	Prediction of pharmacokinetic drug/drug interactions from In vitro data: interactions of the nonsteroidal anti-inflammatory drug lornoxicam with oral anticoagulants. Drug Metab Dispos. 2000 Feb;28(2):161-8.
7	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.
8	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.
9	Contribution of human hepatic cytochrome P450 isoforms to regioselective hydroxylation of steroid hormones. Xenobiotica. 1998 Jun;28(6):539-47.
10	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.
11	Isoform-specific regulation of cytochromes P450 expression by estradiol and progesterone. Drug Metab Dispos. 2013 Feb;41(2):263-9.
12	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.
13	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.
14	Effects of morin on the pharmacokinetics of etoposide in rats. Biopharm Drug Dispos. 2007 Apr;28(3):151-6.
15	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.
16	Roles of cytochromes P450 1A2, 2A6, and 2C8 in 5-fluorouracil formation from tegafur, an anticancer prodrug, in human liver microsomes. Drug Metab Dispos. 2000 Dec;28(12):1457-63.
17	Effects of polyunsaturated fatty acids on prostaglandin synthesis and cyclooxygenase-mediated DNA adduct formation by heterocyclic aromatic amines in human adenocarcinoma colon cells. Mol Carcinog. 2004 Jul;40(3):180-8.
18	Endoxifen and other metabolites of tamoxifen inhibit human hydroxysteroid sulfotransferase 2A1 (hSULT2A1). Drug Metab Dispos. 2014 Nov;42(11):1843-50.
19	Cytochrome P450 1A2 (CYP1A2) activity and risk factors for breast cancer: a cross-sectional study. Breast Cancer Res. 2004;6(4):R352-65.
20	PharmGKB summary: pathways of acetaminophen metabolism at the therapeutic versus toxic doses. Pharmacogenet Genomics. 2015 Aug;25(8):416-26.
21	The effect of apigenin on pharmacokinetics of imatinib and its metabolite N-desmethyl imatinib in rats. Biomed Res Int. 2013;2013:789184.
22	The influence of metabolic gene polymorphisms on urinary 1-hydroxypyrene concentrations in Chinese coke oven workers. Sci Total Environ. 2007 Aug 1;381(1-3):38-46.
23	Identification of P450 enzymes involved in metabolism of verapamil in humans. Naunyn Schmiedebergs Arch Pharmacol. 1993 Sep;348(3):332-7.
24	Metabolism and metabolic inhibition of xanthotoxol in human liver microsomes. Evid Based Complement Alternat Med. 2016;2016:5416509.
25	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.
26	Tamoxifen inhibits cytochrome P450 2C9 activity in breast cancer patients. J Chemother. 2006 Aug;18(4):421-4.
27	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.
28	Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448.
29	Drug-drug interactions with imatinib: an observational study. Medicine (Baltimore). 2016 Oct;95(40):e5076.
30	Drug interactions with calcium channel blockers: possible involvement of metabolite-intermediate complexation with CYP3A. Drug Metab Dispos. 2000 Feb;28(2):125-30.
31	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.
32	A potential role for the estrogen-metabolizing cytochrome P450 enzymes in human breast carcinogenesis. Breast Cancer Res Treat. 2003 Dec;82(3):191-7.
33	A mechanistic approach to antiepileptic drug interactions. Ann Pharmacother. 1998 May;32(5):554-63.
34	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.
35	Cytochrome P450 pharmacogenetics and cancer. Oncogene. 2006 Mar 13;25(11):1679-91.
36	CYP2C19*17 is associated with decreased breast cancer risk. Breast Cancer Res Treat. 2009 May;115(2):391-6.
37	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.
38	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.
39	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.
40	Possible involvement of multiple human cytochrome P450 isoforms in the liver metabolism of propofol. Br J Anaesth. 1998 Jun;80(6):788-95.
41	Vitamin K antagonism of coumarin intoxication in the rat. Thromb Haemost. 1986 Apr 30;55(2):235-9.
42	Tecarfarin, a novel vitamin K reductase antagonist, is not affected by CYP2C9 and CYP3A4 inhibition following concomitant administration of fluconazole in healthy participants. J Clin Pharmacol. 2011Apr;51(4):561-74.