Details of the Drug
General Information of Drug (ID: DMX4GND)
Drug Name |
Meperidine
|
|||||||||||||||||||
---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
Synonyms |
Demarol; Demerol; Dolcontral; Dolosal; Dolsin; Isonipecain; Isonipecaine; Lidol; Lydol; Meperidol; Nemerol; Pethanol; Pethidin; Pethidine; Pethidineter; Pethidinum; Petidina; Petydyna; Phetidine; Piperosal; Pipersal; Meperidine solution; Methyl phenylpiperidine carbonic acid ethyl ester; Operidine EPJ I; Pethidine DBL; Petydyna [Polish]; Demerol (TN); Operidine EPJ-I; Pethidine (INN); Pethidine DBL (TN); Pethidinum [INN-Latin]; Petidina [INN-Spanish]; Ethyl 1-methyl-4-phenylisonipecotate; Ethyl 1-methyl-4-phenylpiperidine-4-carboxylate; N-Methyl-4-phenyl-4-carbethoxypiperidine; Isonipecotic acid, 1-methyl-4-phenyl-, ethyl ester; YIsonipecotic acid, 1-methyl-4-phenyl-, ethyl ester (8CI); 1-Methyl-4-phenyl-4-piperidinecarboxylic acid ethyl ester; 1-Methyl-4-phenyl-piperidin-4-carbon-saeure-aethylester; 1-Methyl-4-phenyl-piperidin-4-carbon-saeure-aethylester [German]; 1-Methyl-4-phenylisonipecotic acid, ethyl ester;1-Methyl-4-phenylpiperidine-4-carboxylic acid ethyl ester; 4-Carbethoxy-1-methyl-4-phenylpiperidine; 4-Piperidinecarboxylic acid, 1-methyl-4-phenyl-, ethyl ester
|
|||||||||||||||||||
Indication |
|
|||||||||||||||||||
Therapeutic Class |
Anesthetics
|
|||||||||||||||||||
Drug Type |
Small molecular drug
|
|||||||||||||||||||
Structure | ||||||||||||||||||||
3D MOL | 2D MOL | |||||||||||||||||||
#Ro5 Violations (Lipinski): 0 | Molecular Weight (mw) | 247.33 | ||||||||||||||||||
Topological Polar Surface Area (xlogp) | 2.5 | |||||||||||||||||||
Rotatable Bond Count (rotbonds) | 4 | |||||||||||||||||||
Hydrogen Bond Donor Count (hbonddonor) | 0 | |||||||||||||||||||
Hydrogen Bond Acceptor Count (hbondacc) | 3 | |||||||||||||||||||
ADMET Property |
|
|||||||||||||||||||
Chemical Identifiers |
|
|||||||||||||||||||
Cross-matching ID | ||||||||||||||||||||
Molecular Interaction Atlas of This Drug
Drug Therapeutic Target (DTT) |
|
|||||||||||||||||||||||||||||||||||||||||
---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
Drug Transporter (DTP) |
|
|||||||||||||||||||||||||||||||||||||||||
Drug-Metabolizing Enzyme (DME) |
|
|||||||||||||||||||||||||||||||||||||||||
Molecular Interaction Atlas (MIA) | ||||||||||||||||||||||||||||||||||||||||||
Drug-Drug Interaction (DDI) Information of This Drug
Coadministration of a Drug Treating the Same Disease as Meperidine
Coadministration of a Drug Treating the Disease Different from Meperidine (Comorbidity)
|
Drug Inactive Ingredient(s) (DIG) and Formulation(s) of This Drug
References
1 | Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services. 2015 | ||||
---|---|---|---|---|---|
2 | BDDCS applied to over 900 drugs | ||||
3 | Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds | ||||
4 | FDA approval: ado-trastuzumab emtansine for the treatment of patients with HER2-positive metastatic breast cancer. Clin Cancer Res. 2014 Sep 1;20(17):4436-41. | ||||
5 | Estimating the safe starting dose in phase I clinical trials and no observed effect level based on QSAR modeling of the human maximum recommended daily dose | ||||
6 | Meperidine, remifentanil and tramadol but not sufentanil interact with alpha(2)-adrenoceptors in alpha(2A)-, alpha(2B)- and alpha(2C)-adrenoceptor ... Eur J Pharmacol. 2008 Mar 17;582(1-3):70-7. | ||||
7 | Meperidine exerts agonist activity at the alpha(2B)-adrenoceptor subtype. Anesthesiology. 2002 Jun;96(6):1420-6. | ||||
8 | Opioids and efflux transporters. Part 3: P-glycoprotein substrate activity of 3-hydroxyl addition to meperidine analogs. Bioorg Med Chem Lett. 2008 Jun 15;18(12):3638-40. | ||||
9 | Is meperidine the drug that just won't die? J Pediatr Pharmacol Ther. 2011 Jul;16(3):167-9. | ||||
10 | CYP2B6, CYP3A4, and CYP2C19 are responsible for the in vitro N-demethylation of meperidine in human liver microsomes. Drug Metab Dispos. 2004 Sep;32(9):930-6. | ||||
11 | Impact of cytochrome P450 variation on meperidine N-demethylation to the neurotoxic metabolite normeperidine. Xenobiotica. 2020 Feb;50(2):209-222. | ||||
12 | Insights into CYP2B6-mediated drug-drug interactions. Acta Pharm Sin B. 2016 Sep;6(5):413-425. | ||||
13 | 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. | ||||
14 | Contribution of human hepatic cytochrome P450 isoforms to regioselective hydroxylation of steroid hormones. Xenobiotica. 1998 Jun;28(6):539-47. | ||||
15 | 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. | ||||
16 | Isoform-specific regulation of cytochromes P450 expression by estradiol and progesterone. Drug Metab Dispos. 2013 Feb;41(2):263-9. | ||||
17 | 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. | ||||
18 | 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. | ||||
19 | Effects of morin on the pharmacokinetics of etoposide in rats. Biopharm Drug Dispos. 2007 Apr;28(3):151-6. | ||||
20 | 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. | ||||
21 | 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. | ||||
22 | Inhibitory effects of anticancer drugs on dextromethorphan-O-demethylase activity in human liver microsomes. Cancer Chemother Pharmacol. 1993;32(6):491-5. | ||||
23 | Effect of genetic polymorphism on the metabolism of endogenous neuroactive substances, progesterone and p-tyramine, catalyzed by CYP2D6. Brain Res Mol Brain Res. 2004 Oct 22;129(1-2):117-23. | ||||
24 | CYP2D6 polymorphisms and tamoxifen metabolism: clinical relevance. Curr Oncol Rep. 2010 Jan;12(1):7-15. | ||||
25 | Inhibition of cytochrome P450 2D6: structure-activity studies using a series of quinidine and quinine analogues. Chem Res Toxicol. 2003 Apr;16(4):450-9. | ||||
26 | Effects of propofol on human hepatic microsomal cytochrome P450 activities. Xenobiotica. 1998 Sep;28(9):845-53. | ||||
27 | Pharmacogenetics of schizophrenia. Am J Med Genet. 2000 Spring;97(1):98-106. | ||||
28 | Roles of CYP2A6 and CYP2B6 in nicotine C-oxidation by human liver microsomes. Arch Toxicol. 1999 Mar;73(2):65-70. | ||||
29 | Structure-activity relationship for human cytochrome P450 substrates and inhibitors. Drug Metab Rev. 2002 Feb-May;34(1-2):69-82. | ||||
30 | Effect of tamoxifen on the enzymatic activity of human cytochrome CYP2B6. J Pharmacol Exp Ther. 2002 Jun;301(3):945-52. | ||||
31 | Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448. | ||||
32 | Hepatic metabolism of diclofenac: role of human CYP in the minor oxidative pathways. Biochem Pharmacol. 1999 Sep 1;58(5):787-96. | ||||
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 | Drugs that may have potential CYP2B6 interactions. | ||||
35 | Involvement of human cytochrome P450 2B6 in the omega- and 4-hydroxylation of the anesthetic agent propofol. Xenobiotica. 2007 Jul;37(7):717-24. | ||||
36 | Nicotine and 4-(methylnitrosamino)-1-(3-pyridyl)-butanone metabolism by cytochrome P450 2B6. Drug Metab Dispos. 2005 Dec;33(12):1760-4. | ||||
37 | PharmGKB summary: phenytoin pathway. Pharmacogenet Genomics. 2012 Jun;22(6):466-70. | ||||
38 | 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. | ||||
39 | 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. | ||||
40 | 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. | ||||
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 | A mechanistic approach to antiepileptic drug interactions. Ann Pharmacother. 1998 May;32(5):554-63. | ||||
46 | 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. | ||||
47 | Possible involvement of multiple human cytochrome P450 isoforms in the liver metabolism of propofol. Br J Anaesth. 1998 Jun;80(6):788-95. | ||||
48 | Human intestinal transporter database: QSAR modeling and virtual profiling of drug uptake, efflux and interactions. Pharm Res. 2013 Apr;30(4):996-1007. | ||||
49 | MDR1 (ABCB1) G1199A (Ser400Asn) polymorphism alters transepithelial permeability and sensitivity to anticancer agents. Cancer Chemother Pharmacol. 2009 Jun;64(1):183-8. | ||||
50 | Mammalian drug efflux transporters of the ATP binding cassette (ABC) family in multidrug resistance: A review of the past decade. Cancer Lett. 2016 Jan 1;370(1):153-64. | ||||
51 | Folate transporter expression decreases in the human placenta throughout pregnancy and in pre-eclampsia. Pregnancy Hypertens. 2012 Apr;2(2):123-31. | ||||
52 | Comparative studies on in vitro methods for evaluating in vivo function of MDR1 P-glycoprotein. Pharm Res. 2001 Dec;18(12):1660-8. | ||||
53 | Antiestrogens and steroid hormones: substrates of the human P-glycoprotein. Biochem Pharmacol. 1994 Jul 19;48(2):287-92. | ||||
54 | Association of genetic polymorphisms in the influx transporter SLCO1B3 and the efflux transporter ABCB1 with imatinib pharmacokinetics in patients with chronic myeloid leukemia. Ther Drug Monit. 2011 Apr;33(2):244-50. | ||||
55 | Noradrenergic alpha-2 receptor agonists reverse working memory deficits induced by the anxiogenic drug, FG7142, in rats. Pharmacol Biochem Behav. 2000 Nov;67(3):397-403. | ||||
56 | Clinical pharmacokinetics of lofexidine, the alpha 2-adrenergic receptor agonist, in opiate addicts plasma using a highly sensitive liquid chromatography tandem mass spectrometric analysis. Am J DrugAlcohol Abuse. 2008;34(5):611-6. | ||||
57 | Emerging drugs for attention-deficit/hyperactivity disorder. Expert Opin Emerg Drugs. 2007 Sep;12(3):423-34. | ||||
58 | Dexmedetomidine in intensive care unit: a study of hemodynamic changes. Middle East J Anesthesiol. 2002 Oct;16(6):587-95. | ||||
59 | Acute neurotoxicity after yohimbine ingestion by a body builder. Clin Toxicol (Phila). 2009 Sep;47(8):827-9. | ||||
60 | Centrally acting sympathetic inhibitors for therapy of patients with hypertension. Nippon Rinsho. 1997 Aug;55(8):2081-5. | ||||
61 | Tizanidine. A review of its pharmacology, clinical efficacy and tolerability in the management of spasticity associated with cerebral and spinal disorders. Drugs. 1997 Mar;53(3):435-52. | ||||
62 | Potent alpha(2A)-adrenoceptor-mediated vasoconstriction by brimonidine in porcine ciliary arteries. Invest Ophthalmol Vis Sci. 2001 Aug;42(9):2049-55. | ||||
63 | Increased alpha2-adrenergic constriction of isolated arterioles in diffuse scleroderma. Arthritis Rheum. 2000 Aug;43(8):1886-90. | ||||
64 | Product Information. Buprenex (buprenorphine). Reckitt and Colman Pharmaceutical, Richmond, VA. | ||||
65 | Hansen BS, Dam M, Brandt J, et al "Influence of dextropropoxyphene on steady state serum levels and protein binding of three anti-epileptic drugs in man." Acta Neurol Scand 61 (1980): 357-67. [PMID: 6998251] | ||||
66 | US Food and Drug Administration "FDA warns about serious risks and death when combining opioid pain or cough medicines with benzodiazepines requires its strongest warning.". | ||||
67 | Product Information. Apadaz (acetaminophen-benzhydrocodone). KemPharm, Inc, Coralville, IA. | ||||
68 | Browne B, Linter S "Monoamine oxidase inhibitors and narcotic analgesics: a critical review of the implications for treatment." Br J Psychiatry 151 (1987): 210-2. [PMID: 2891392] | ||||
69 | Lambertsen CJ, Wendel H, Longenhagen JB "The separate and combined respiratory effects of chlorpromazine and meperidine in normal men controlled at 46 mm Hg alveolar pCO2." J Pharmacol Exp Ther 131 (1961): 381-93. [PMID: 13758472] | ||||
70 | Gilman AG, Rall TW, Nies AS, Taylor P, eds. "Goodman and Gilman's the Pharmacological Basis of Therapeutics. 8th ed." New York, NY: Pergamon Press Inc. (1990):. | ||||
71 | US Food and Drug Administration "FDA warns about serious risks and death when combining opioid pain or cough medicines with benzodiazepines requires its strongest warning.". | ||||
72 | Achamallah NS "Visual hallucinations after combining fluoxetine and dextromethorphan ." Am J Psychiatry 149 (1992): 1406. [PMID: 1530079] | ||||
73 | Bergeron L, Boule M, Perreault S "Serotonin toxicity associated with concomitant use of linezolid." Ann Pharmacother 39 (2005): 956-61. [PMID: 15827071] | ||||
74 | Cerner Multum, Inc. "UK Summary of Product Characteristics.". | ||||
75 | Product Information. Piqray (alpelisib). Novartis Pharmaceuticals, East Hanover, NJ. | ||||
76 | Ghoneim MM, Pandya H "Plasma protein binding of bupivacaine and its interaction with other drugs in man." Br J Anaesth 46 (1974): 435-8. [PMID: 4458761] | ||||
77 | Gill SS, Wright EM, Reilly CS "Pharmacokinetic interaction of propofol and fentanyl: single bolus injection study." Br J Anaesth 65 (1990): 760-5. [PMID: 2265045] | ||||
78 | Sturner WQ, Garriott JC "Deaths involving propoxyphene: a study of 41 cases over a two-year period." JAMA 223 (1973): 1125-30. [PMID: 4739371] | ||||
79 | Cerner Multum, Inc. "Australian Product Information.". | ||||
80 | Pond SM, Kretschzmar KM "Effect of phenytoin on meperidine clearance and normeperidine formation." Clin Pharmacol Ther 30 (1981): 680-6. [PMID: 7297025] | ||||
81 | Eckhardt K, Ammon S, Hofmann U, Riebe A, Gugeler N, Mikus G "Gabapentin enhances the analgesic effect of morphine in healthy volunteers." Anesth Analg 91 (2000): 185-91. [PMID: 10866910] | ||||
82 | Guay DR, Meatherall RC, Chalmers JL, Grahame GR "Cimetidine alters pethidine disposition in man." Br J Clin Pharmacol 18 (1984): 907-14. [PMID: 6529532] | ||||
83 | Product Information. Alphagan (brimonidine ophthalmic). Allergan Inc, Irvine, CA. | ||||
84 | Gannon RG, Pearsall W, Rowley R "Isoniazid, meperidine, and hypotension." Ann Intern Med 99 (1983): 415. [PMID: 6614704] | ||||
85 | Product Information. Suprep Bowel Prep Kit (magnesium/potassium/sodium sulfates). Braintree Laboratories, Braintree, MA. | ||||
86 | Product Information. Zulresso (brexanolone). Sage Therapeutics, Inc., Cambridge, MA. | ||||
87 | Product Information. Thalomid (thalidomide). Celgene Corporation, Warren, NJ. | ||||
88 | Agencia Espaola de Medicamentos y Productos Sanitarios Healthcare "Centro de informacion online de medicamentos de la AEMPS - CIMA.". | ||||
89 | Product Information. Reglan (metoclopramide). Wyeth-Ayerst Laboratories, Philadelphia, PA. | ||||
90 | Canadian Pharmacists Association. | ||||
91 | Product Information. Wellbutrin XL (buPROPion). GlaxoSmithKline, Philadelphia, PA. | ||||
92 | Chan BSH, Graudins A, Whyte IM, Dawson AH, Braitberg G, Duggin GG "Serotonin syndrome resulting from drug interactions." Med J Aust 169 (1998): 523-5. [PMID: 9861909] | ||||
93 | Product Information. Belviq (lorcaserin). Eisai Inc, Teaneck, NJ. | ||||
94 | Product Information. Artane (trihexyphenidyl). Lederle Laboratories, Wayne, NJ. | ||||
95 | Product Information. Xeglyze (abametapir topical). Dr. Reddy's Laboratories Inc, Upper Saddle River, NJ. | ||||
96 | Cerner Multum, Inc. "Canadian Product Information.". | ||||
97 | Product Information. Tavalisse (fostamatinib). Rigel Pharmaceuticals, South San Francisco, CA. | ||||
98 | Hoffman JC, Smith TC "The respiratory effects of meperidine and propiomazine in man." Anesthesiology 32 (1970): 325-31. [PMID: 4392394] | ||||