Details of the Drug
General Information of Drug (ID: DM82Z30)
Drug Name |
Topiramate
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Synonyms |
Epitoma; Epitomax; TOR; Tipiramate; Tipiramato; Topamac; Topamax; Topimax; Topina; Topiramato; Topiramatum; Topomax; Cilag brandof topiramate; Janssen brand of topiramate; Ortho brand of topiramate; Tipiramate [French]; Tipiramato [Spanish]; Topamax Sprinkle; Topiramate tablet; Topiramatum [Latin]; Topiramic acid; McN 4853; RWJ 17021; KS-1122; KW-6485; McN-4853; RWJ-17021; Topamax (TN); Topamax, Topiramate; Topiramate (TPM); Topiramate / Placebo; Topiramato [INN-Spanish]; Topiramatum [INN-Latin]; USL-255; RWJ-17021-000; Topiramate [USAN:BAN:INN]; Topiramate (JAN/USAN/INN); Beta-D-Fructopyranose, 2,3:4,5-bis-O-(1-methylethylidene)-, sulfamate; Beta-D-Fructopyranose, 2,3:4,5-bis-O-(1-methylethylidene)-, sulfamate (9CI);Beta.-D-Fructopyranose, 2,3:4,5-bis-O-(1-methylethylidene)-, 1-sulfamate; [(3aS,5aR,8aR,8bS)-2,2,7,7-tetramethyltetrahydro-3aH-bis[1,3]dioxolo[4,5-b:4',5'-d]pyran-3a-yl]methyl sulfamate; 2,3-4,5-bis-O-(1-methylethylidene)-beta-D-fructopyranose sulfamate; 2,3:4,5-Bis-O-(1-methylethylidene) .beta.-D-fructopyranose sulfamate; 2,3:4,5-Bis-O-(1-methylethylidene)-36-D-fructo-pyranose sulfamate; 2,3:4,5-Bis-O-(1-methylethylidene)-beta-D-fructopyranose sulfamate; 2,3:4,5-Di-O-isopropylidene-(beta)-D-fructopyranose sulfamate; 2,3:4,5-Di-O-isopropylidene-beta-D-fructopyranose sulfamate; 5H-Bis[1,3]dioxolo[4,5-b:4',5'-d]pyran, beta
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Indication |
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Therapeutic Class |
Anticonvulsants
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Drug Type |
Small molecular drug
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Structure | ||||||||||||||||||||||||||||
3D MOL | 2D MOL | |||||||||||||||||||||||||||
#Ro5 Violations (Lipinski): 0 | Molecular Weight (mw) | 339.36 | ||||||||||||||||||||||||||
Topological Polar Surface Area (xlogp) | -0.8 | |||||||||||||||||||||||||||
Rotatable Bond Count (rotbonds) | 3 | |||||||||||||||||||||||||||
Hydrogen Bond Donor Count (hbonddonor) | 1 | |||||||||||||||||||||||||||
Hydrogen Bond Acceptor Count (hbondacc) | 9 | |||||||||||||||||||||||||||
ADMET Property |
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Chemical Identifiers |
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Cross-matching ID | ||||||||||||||||||||||||||||
Molecular Interaction Atlas of This Drug
Drug Therapeutic Target (DTT) |
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Drug Transporter (DTP) |
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Drug-Metabolizing Enzyme (DME) |
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Molecular Interaction Atlas (MIA) | |||||||||||||||||||||||||||
Drug-Drug Interaction (DDI) Information of This Drug
Coadministration of a Drug Treating the Disease Different from Topiramate (Comorbidity)
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Drug Inactive Ingredient(s) (DIG) and Formulation(s) of This Drug
References
1 | 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: 6849). | ||||
---|---|---|---|---|---|
2 | Use of second-generation antiepileptic drugs in the pediatric population. Paediatr Drugs. 2008;10(4):217-54. | ||||
3 | Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services. 2015 | ||||
4 | The ChEMBL database in 2017. Nucleic Acids Res. 2017 Jan 4;45(D1):D945-D954. | ||||
5 | Knauf H, Mutschler E: Clinical pharmacokinetics and pharmacodynamics of torasemide. Clin Pharmacokinet. 1998 Jan;34(1):1-24. doi: 10.2165/00003088-199834010-00001. | ||||
6 | BDDCS applied to over 900 drugs | ||||
7 | Clinical pharmacology of topiramate: a review. Epilepsia. 2000;41 Suppl 1:S61-5. | ||||
8 | Walker MC, Sander JW: Topiramate: a new antiepileptic drug for refractory epilepsy. Seizure. 1996 Sep;5(3):199-203. | ||||
9 | Murrell GA, Rapeport WG: Clinical pharmacokinetics of allopurinol. Clin Pharmacokinet. 1986 Sep-Oct;11(5):343-53. doi: 10.2165/00003088-198611050-00001. | ||||
10 | 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 | ||||
11 | Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds | ||||
12 | Development of medications for alcohol use disorders: recent advances and ongoing challenges. Expert Opin Emerg Drugs. 2005 May;10(2):323-43. | ||||
13 | The antiepileptic drug topiramate is a substrate for human P-glycoprotein but not multidrug resistance proteins. Pharm Res. 2009 Nov;26(11):2464-70. | ||||
14 | Dose-dependent induction of cytochrome P450 (CYP) 3A4 and activation of pregnane X receptor by topiramate. Epilepsia. 2003 Dec;44(12):1521-8. | ||||
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 | 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. | ||||
24 | Human intestinal transporter database: QSAR modeling and virtual profiling of drug uptake, efflux and interactions. Pharm Res. 2013 Apr;30(4):996-1007. | ||||
25 | MDR1 (ABCB1) G1199A (Ser400Asn) polymorphism alters transepithelial permeability and sensitivity to anticancer agents. Cancer Chemother Pharmacol. 2009 Jun;64(1):183-8. | ||||
26 | 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. | ||||
27 | Folate transporter expression decreases in the human placenta throughout pregnancy and in pre-eclampsia. Pregnancy Hypertens. 2012 Apr;2(2):123-31. | ||||
28 | Comparative studies on in vitro methods for evaluating in vivo function of MDR1 P-glycoprotein. Pharm Res. 2001 Dec;18(12):1660-8. | ||||
29 | Antiestrogens and steroid hormones: substrates of the human P-glycoprotein. Biochem Pharmacol. 1994 Jul 19;48(2):287-92. | ||||
30 | 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. | ||||
31 | Pharmacogenetics of new analgesics. Br J Pharmacol. 2011 Jun;163(3):447-60. | ||||
32 | The efficacy of the AMPA receptor antagonist NS1209 and lidocaine in nerve injury pain: a randomized, double-blind, placebo-controlled, three-way crossover study. Anesth Analg. 2009 Apr;108(4):1311-9. | ||||
33 | 4,10-Dihydro-4-oxo-4H-imidazo[1,2-a]indeno[1,2-e]pyrazin-2-carboxylic acid derivatives: highly potent and selective AMPA receptors antagonists with... Bioorg Med Chem Lett. 2000 May 15;10(10):1133-7. | ||||
34 | 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. (Target id: 450). | ||||
35 | Chemo-enzymatic synthesis of a series of 2,4-syn-functionalized (S)-glutamate analogues: new insight into the structure-activity relation of ionotr... J Med Chem. 2008 Jul 24;51(14):4093-103. | ||||
36 | Synthesis of chiral 1-(2'-amino-2'-carboxyethyl)-1,4-dihydro-6,7-quinoxaline-2,3-diones: alpha-amino-3-hydroxy-5-methyl-4-isoxazolepropionate recep... J Med Chem. 1996 Oct 25;39(22):4430-8. | ||||
37 | Cerner Multum, Inc. "UK Summary of Product Characteristics.". | ||||
38 | Product Information. Topamax (topiramate). Ortho Pharmaceutical Corporation, Raritan, NJ. | ||||
39 | Mendelson J, Jones RT, Upton R, Jacob P 3rd "Methamphetamine and ethanol interactions in humans." Clin Pharmacol Ther 57 (1995): 559-68. [PMID: 7768079] | ||||
40 | Belcastro V, Costa C, Striano P "Levetiracetam-associated hyponatremia." Seizure 17 (2008): 389-90. [PMID: 18584781] | ||||
41 | Warrington SJ, Ankier SI, Turner P "Evaluation of possible interactions between ethanol and trazodone or amitriptyline." Neuropsychobiology 15 (1986): 31-7. [PMID: 3725002] | ||||
42 | Cerner Multum, Inc. "Australian Product Information.". | ||||
43 | Bourgeois BF "Drug interaction profile of topiramate." Epilepsia 37(suppl 2 (1996): s14-7. [PMID: 8641241] | ||||
44 | Product Information. Alphagan (brimonidine ophthalmic). Allergan Inc, Irvine, CA. | ||||
45 | Product Information. Zulresso (brexanolone). Sage Therapeutics, Inc., Cambridge, MA. | ||||
46 | Product Information. Reyvow (lasmiditan). Lilly, Eli and Company, Indianapolis, IN. | ||||
47 | Product Information. Addyi (flibanserin). Sprout Pharmaceuticals, Raleigh, NC. | ||||
48 | Product Information. Thalomid (thalidomide). Celgene Corporation, Warren, NJ. | ||||
49 | 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] | ||||
50 | Sekar M, Mimpriss TJ "Buprenorphine, benzodiazepines and prolonged respiratory depression." Anaesthesia 42 (1987): 567-8. [PMID: 3592200] | ||||
51 | 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] | ||||
52 | Product Information. Zanaflex (tizanidine). Acorda Therapeutics, Hawthorne, NY. | ||||
53 | Product Information. Zyrtec (cetirizine). Pfizer US Pharmaceuticals, New York, NY. | ||||