General Information of Drug (ID: DMM3L6Z)

Drug Name
Ketobemidone Drug Info
Synonyms
Ketobemidone hydrochloride; Cliradon hydrochloride; Ketobimedon hydrochloride; UNII-U9U6LTV80K; 5965-49-1; EINECS 227-749-8; U9U6LTV80K; 1-Methyl-4-(m-hydroxyphenyl)piperidine-4-ethylketone hydrochloride; Ketobemidone HCl; 1-Propanone, 1-(4-(m-hydroxyphenyl)-1-methyl-4-piperidyl)-, hydrochloride; Ketogan (TN); AC1L2YOJ; 1-[4-(3-hydroxyphenyl)-1-methylpiperidin-4-yl]propan-1-one hydrochloride(1:1); AC1Q5G7W; SCHEMBL9706814; 469-79-4 (Parent); DTXSID00208327; LS-123062; D08101
Indication
Disease Entry ICD 11 Status REF
Pain MG30-MG3Z Approved [1]
Cross-matching ID
PubChem CID
10101
ChEBI ID
CHEBI:6125
CAS Number
CAS 469-79-4
TTD Drug ID
DMM3L6Z
INTEDE Drug ID
DR0905

Molecule-Related Drug Atlas

Molecule-Related Drug Atlas
Molecule Type:
DTT
DME
Drug Status:
Approved Drug(s)
Drug(s) Targeting Opioid receptor (OPR)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Methadone DMTW6IU Advanced cancer 2A00-2F9Z Approved [5]
Oxymorphone DM65AGJ Pain MG30-MG3Z Approved [6]
Dextropropoxyphene DM23HCX Pain MG30-MG3Z Approved [7]
Sufentanil DMU7YEL Analgesia MB40.8 Approved [8]
Naltrexone DMUL45H Alcohol dependence 6C40.2 Approved [9]
Levorphanol DMGS80V Pain MG30-MG3Z Approved [10]
Pentazocine DM1XBHS Pain MG30-MG3Z Approved [11]
Nalmefene DM4YWCZ Opioid dependence 6C43.2Z Approved [12]
Tilidine DMJW0VS Pain MG30-MG3Z Approved [13]
Dihydrocodeine DMB0FWL Allergic rhinitis CA08.0 Phase 4 [14]
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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 [15]
Progesterone DMUY35B Amenorrhea GA20.0 Approved [16]
Tamoxifen DMLB0EZ Breast cancer 2C60-2C65 Approved [17]
Estradiol DMUNTE3 Acne vulgaris ED80 Approved [18]
Acetaminophen DMUIE76 Allergic rhinitis CA08.0 Approved [19]
Imatinib DM7RJXL Acute lymphoblastic leukaemia 2A85 Approved [20]
Etoposide DMNH3PG Acute myelogenous leukaemia 2A41 Approved [21]
Zidovudine DM4KI7O Human immunodeficiency virus infection 1C62 Approved [22]
Prasterone DM67VKL Chronic obstructive pulmonary disease CA22 Approved [16]
Verapamil DMA7PEW Angina pectoris BA40 Approved [4]
⏷ Show the Full List of 10 Drug(s)
Drug(s) Metabolized By Cytochrome P450 2C8 (CYP2C8)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Fluorouracil DMUM7HZ Adenocarcinoma 2D40 Approved [23]
Estradiol DMUNTE3 Acne vulgaris ED80 Approved [24]
Imatinib DM7RJXL Acute lymphoblastic leukaemia 2A85 Approved [24]
Zidovudine DM4KI7O Human immunodeficiency virus infection 1C62 Approved [25]
Verapamil DMA7PEW Angina pectoris BA40 Approved [26]
Diclofenac DMPIHLS Chronic renal failure GB61.Z Approved [27]
Sorafenib DMS8IFC Adenocarcinoma 2D40 Approved [28]
Quinine DMSWYF5 Malaria 1F40-1F45 Approved [24]
Mycophenolate mofetil DMPQAGE Hepatosplenic T-cell lymphoma Approved [29]
Propofol DMB4OLE Anaesthesia 9A78.6 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 [25]
Imatinib DM7RJXL Acute lymphoblastic leukaemia 2A85 Approved [34]
Zidovudine DM4KI7O Human immunodeficiency virus infection 1C62 Approved [25]
Verapamil DMA7PEW Angina pectoris BA40 Approved [35]
Diclofenac DMPIHLS Chronic renal failure GB61.Z Approved [36]
Estrone DM5T6US Acne vulgaris ED80 Approved [37]
Valproate DMCFE9I Epilepsy 8A60-8A68 Approved [38]
⏷ Show the Full List of 10 Drug(s)
Drug(s) Metabolized By Cytochrome P450 2B6 (CYP2B6)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Tamoxifen DMLB0EZ Breast cancer 2C60-2C65 Approved [39]
Verapamil DMA7PEW Angina pectoris BA40 Approved [25]
Diclofenac DMPIHLS Chronic renal failure GB61.Z Approved [40]
Estrone DM5T6US Acne vulgaris ED80 Approved [33]
Valproate DMCFE9I Epilepsy 8A60-8A68 Approved [41]
Irinotecan DMP6SC2 Adenocarcinoma 2D40 Approved [42]
Propofol DMB4OLE Anaesthesia 9A78.6 Approved [43]
Nicotine DMWX5CO Lung cancer 2C25.0 Approved [44]
Phenytoin DMNOKBV Epilepsy 8A60-8A68 Approved [45]
Amitriptyline DMK7F9S Depression 6A70-6A7Z Approved [46]
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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 [47]
Progesterone DMUY35B Amenorrhea GA20.0 Approved [31]
Tamoxifen DMLB0EZ Breast cancer 2C60-2C65 Approved [48]
Estradiol DMUNTE3 Acne vulgaris ED80 Approved [49]
Zidovudine DM4KI7O Human immunodeficiency virus infection 1C62 Approved [25]
Verapamil DMA7PEW Angina pectoris BA40 Approved [50]
Diclofenac DMPIHLS Chronic renal failure GB61.Z Approved [51]
Valproate DMCFE9I Epilepsy 8A60-8A68 Approved [38]
Quinine DMSWYF5 Malaria 1F40-1F45 Approved [52]
Propofol DMB4OLE Anaesthesia 9A78.6 Approved [30]
⏷ Show the Full List of 10 Drug(s)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Acetaminophen DMUIE76 Allergic rhinitis CA08.0 Approved [53]
Diclofenac DMPIHLS Chronic renal failure GB61.Z Approved [54]
Sorafenib DMS8IFC Adenocarcinoma 2D40 Approved [55]
Valproate DMCFE9I Epilepsy 8A60-8A68 Approved [4]
Mycophenolate mofetil DMPQAGE Hepatosplenic T-cell lymphoma Approved [56]
Propofol DMB4OLE Anaesthesia 9A78.6 Approved [4]
Ibuprofen DM8VCBE Dysmenorrhea GA34.3 Approved [4]
Troglitazone DM3VFPD Diabetic complication 5A2Y Approved [57]
Nateglinide DMLK2QH Diabetic complication 5A2Y Approved [4]
Haloperidol DM96SE0 Delirium Approved [4]
⏷ Show the Full List of 10 Drug(s)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Imatinib DM7RJXL Acute lymphoblastic leukaemia 2A85 Approved [4]
Etoposide DMNH3PG Acute myelogenous leukaemia 2A41 Approved [58]
Valproate DMCFE9I Epilepsy 8A60-8A68 Approved [4]
Diazepam DM08E9O Alcohol withdrawal Approved [4]
Dapsone DM4LT8A Acne vulgaris ED80 Approved [4]
Ifosfamide DMCT3I8 Adult central nervous system germ cell tumor Approved [4]
Nateglinide DMLK2QH Diabetic complication 5A2Y Approved [4]
Thalidomide DM70BU5 Adult T-cell leukemia/lymphoma Approved [4]
Irbesartan DMTP1DC Diabetic kidney disease GB61.Z Approved [4]
Terbinafine DMI6HUW Fungal infection 1F29-1F2F Approved [4]
⏷ Show the Full List of 10 Drug(s)

Molecular Interaction Atlas of This Drug

Molecular Interaction Atlas

Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Opioid receptor (OPR) TTN4QDT NOUNIPROTAC Modulator [2]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 3A4 (CYP3A4) DE4LYSA CP3A4_HUMAN Substrate [3]
Cytochrome P450 2C9 (CYP2C9) DE5IED8 CP2C9_HUMAN Substrate [3]
Mephenytoin 4-hydroxylase (CYP2C19) DEGTFWK CP2CJ_HUMAN Substrate [3]
Cytochrome P450 2B6 (CYP2B6) DEPKLMQ CP2B6_HUMAN Substrate [3]
Cytochrome P450 2C8 (CYP2C8) DES5XRU CP2C8_HUMAN Substrate [3]
Prostaglandin G/H synthase 1 (COX-1) DE073H6 PGH1_HUMAN Substrate [4]
UDP-glucuronosyltransferase 1A9 (UGT1A9) DE85D2P UD19_HUMAN Substrate [4]

References

1 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services. 2015
2 The mu1 and mu2 opioid receptor binding of ketobemidone, norketobemidone and 3-dimethylamino-1,1-diphenylbutene. Pharmacol Toxicol. 1996 Aug;79(2):103-4.
3 Ketobemidone is a substrate for cytochrome P4502C9 and 3A4, but not for P-glycoprotein. Xenobiotica. 2005 Aug;35(8):785-96.
4 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.
5 Methadone treatment and its dangers. Medicina (Kaunas). 2009;45(5):419-25.
6 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 7094).
7 Retrospective diagnosis of an adverse drug reaction in a breastfed neonate: liquid chromatography-tandem mass spectrometry quantification of dextropropoxyphene and norpropoxyphene in newborn and maternal hair. J Anal Toxicol. 2008 Nov-Dec;39(9):787-9.
8 mu-opioid receptor-stimulated synthesis of reactive oxygen species is mediated via phospholipase D2. J Neurochem. 2009 Aug;110(4):1288-96.
9 An evaluation of mu-opioid receptor (OPRM1) as a predictor of naltrexone response in the treatment of alcohol dependence: results from the Combined Pharmacotherapies and Behavioral Interventions for Alcohol Dependence (COMBINE) study. Arch Gen Psychiatry. 2008 Feb;65(2):135-44.
10 Comparison of the effects of dextromethorphan, dextrorphan, and levorphanol on the hypothalamo-pituitary-adrenal axis. J Pharmacol Exp Ther. 2004 May;309(2):515-22.
11 Functional characterization of a sigma receptor and its gene expression by haloperidol. Nippon Yakurigaku Zasshi. 1999 Jul;114(1):61-8.
12 Unconditioned behavioral effects of the powerful kappa-opioid hallucinogen salvinorin A in nonhuman primates: fast onset and entry into cerebrospin... J Pharmacol Exp Ther. 2009 Feb;328(2):588-97.
13 Actions of tilidine and nortilidine on cloned opioid receptors. Eur J Pharmacol. 2005 Jan 4;506(3):205-8.
14 Affinities of dihydrocodeine and its metabolites to opioid receptors. Pharmacol Toxicol. 2002 Aug;91(2):57-63.
15 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.
16 Contribution of human hepatic cytochrome P450 isoforms to regioselective hydroxylation of steroid hormones. Xenobiotica. 1998 Jun;28(6):539-47.
17 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.
18 Isoform-specific regulation of cytochromes P450 expression by estradiol and progesterone. Drug Metab Dispos. 2013 Feb;41(2):263-9.
19 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.
20 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.
21 Effects of morin on the pharmacokinetics of etoposide in rats. Biopharm Drug Dispos. 2007 Apr;28(3):151-6.
22 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.
23 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.
24 Role of cytochrome P450 2C8 in drug metabolism and interactions. Pharmacol Rev. 2016 Jan;68(1):168-241.
25 Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448.
26 Differential expression and function of CYP2C isoforms in human intestine and liver. Pharmacogenetics. 2003 Sep;13(9):565-75.
27 Analysis of human cytochrome P450 2C8 substrate specificity using a substrate pharmacophore and site-directed mutants. Biochemistry. 2004 Dec 14;43(49):15379-92.
28 Interaction of sorafenib and cytochrome P450 isoenzymes in patients with advanced melanoma: a phase I/II pharmacokinetic interaction study. Cancer Chemother Pharmacol. 2011 Nov;68(5):1111-8.
29 PharmGKB summary: mycophenolic acid pathway. Pharmacogenet Genomics. 2014 Jan;24(1):73-9.
30 Possible involvement of multiple human cytochrome P450 isoforms in the liver metabolism of propofol. Br J Anaesth. 1998 Jun;80(6):788-95.
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 Drug-drug interactions with imatinib: an observational study. Medicine (Baltimore). 2016 Oct;95(40):e5076.
35 Drug interactions with calcium channel blockers: possible involvement of metabolite-intermediate complexation with CYP3A. Drug Metab Dispos. 2000 Feb;28(2):125-30.
36 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.
37 A potential role for the estrogen-metabolizing cytochrome P450 enzymes in human breast carcinogenesis. Breast Cancer Res Treat. 2003 Dec;82(3):191-7.
38 A mechanistic approach to antiepileptic drug interactions. Ann Pharmacother. 1998 May;32(5):554-63.
39 Effect of tamoxifen on the enzymatic activity of human cytochrome CYP2B6. J Pharmacol Exp Ther. 2002 Jun;301(3):945-52.
40 Hepatic metabolism of diclofenac: role of human CYP in the minor oxidative pathways. Biochem Pharmacol. 1999 Sep 1;58(5):787-96.
41 Insights into CYP2B6-mediated drug-drug interactions. Acta Pharm Sin B. 2016 Sep;6(5):413-425.
42 Drugs that may have potential CYP2B6 interactions.
43 Involvement of human cytochrome P450 2B6 in the omega- and 4-hydroxylation of the anesthetic agent propofol. Xenobiotica. 2007 Jul;37(7):717-24.
44 Nicotine and 4-(methylnitrosamino)-1-(3-pyridyl)-butanone metabolism by cytochrome P450 2B6. Drug Metab Dispos. 2005 Dec;33(12):1760-4.
45 PharmGKB summary: phenytoin pathway. Pharmacogenet Genomics. 2012 Jun;22(6):466-70.
46 Application of the relative activity factor approach in scaling from heterologously expressed cytochromes p450 to human liver microsomes: studies on amitriptyline as a model substrate. J Pharmacol Exp Ther. 2001 Apr;297(1):326-37.
47 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.
48 Cytochrome P450 pharmacogenetics and cancer. Oncogene. 2006 Mar 13;25(11):1679-91.
49 CYP2C19*17 is associated with decreased breast cancer risk. Breast Cancer Res Treat. 2009 May;115(2):391-6.
50 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.
51 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.
52 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.
53 Polymorphic expression of UGT1A9 is associated with variable acetaminophen glucuronidation in neonates: a population pharmacokinetic and pharmacogenetic study. Clin Pharmacokinet. 2018 Oct;57(10):1325-1336.
54 Glucuronidation of nonsteroidal anti-inflammatory drugs: identifying the enzymes responsible in human liver microsomes. Drug Metab Dispos. 2005 Jul;33(7):1027-35.
55 Pharmacokinetic interaction involving sorafenib and the calcium-channel blocker felodipine in a patient with hepatocellular carcinoma. Invest New Drugs. 2011 Dec;29(6):1511-4.
56 The evolution of population pharmacokinetic models to describe the enterohepatic recycling of mycophenolic acid in solid organ transplantation and autoimmune disease. Clin Pharmacokinet. 2011 Jan;50(1):1-24.
57 The UDP-glucuronosyltransferase 1A9 enzyme is a peroxisome proliferator-activated receptor alpha and gamma target gene. J Biol Chem. 2003 Apr 18;278(16):13975-83.
58 Peroxidative free radical formation and O-demethylation of etoposide(VP-16) and teniposide(VM-26). Biochem Biophys Res Commun. 1986 Feb 26;135(1):215-20.