Details of the Drug
General Information of Drug (ID: DM5PCS7)
Drug Name |
Bupropion
|
|||||||||||||||||||
---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
Synonyms |
bupropion; Amfebutamone; 34911-55-2; Amfebutamon; 2-(tert-butylamino)-1-(3-chlorophenyl)propan-1-one; amfebutamonum; Amfebutamona; (+-)-Bupropion; Wellbatrin; Bupropion [INN:BAN]; 34841-39-9; Elontril; Amfebutamonum [INN-Latin]; Zyban; Amfebutamona [INN-Spanish]; Bupropion SR; AMFEBUTAMONE HCl; alpha-(tert-butylamino)-m-chloropropiophenone; CHEMBL894; BRN 2101062; (+-)-1-(3-chlorophenyl)-2-((1,1-dimethylethyl)amino)-1-propanone; CHEBI:3219; SNPPWIUOZRMYNY-UHFFFAOYSA-N; 1-(3-chlorophenyl)-2-[(1,1-dimethylethyl)amino]propan-1-one; Amfebutamon; Amfebutamonum; Elont; Bupropion Hcl; Bupropion hydrocloride; Bupropion (INN); Bupropion (Old RN); Bupropion (USAN); Alpha-(tert-Butylamino)-m-chloropropiophenone; Alpha-(tert-butylamino)-m-chloropropiophenone; (-)-2-(tert-Butylamino)-3'-chloropropiophenone; (-)-2-(tert-Butylamino)-3'-chlorpropiophenon; 1-Propanone; 2-(Tert-Butylamino)-3'-chloropropiophenone
|
|||||||||||||||||||
Indication |
|
|||||||||||||||||||
Drug Type |
Small molecular drug
|
|||||||||||||||||||
Structure | ||||||||||||||||||||
3D MOL | 2D MOL | |||||||||||||||||||
#Ro5 Violations (Lipinski): 0 | Molecular Weight (mw) | 239.74 | ||||||||||||||||||
Topological Polar Surface Area (xlogp) | 3.2 | |||||||||||||||||||
Rotatable Bond Count (rotbonds) | 4 | |||||||||||||||||||
Hydrogen Bond Donor Count (hbonddonor) | 1 | |||||||||||||||||||
Hydrogen Bond Acceptor Count (hbondacc) | 2 | |||||||||||||||||||
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) | ||||||||||||||||||||||||||||||||||||||||||
Molecular Expression Atlas of This Drug
The Studied Disease | Smoking dependence | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
ICD Disease Classification | 6C4A.2 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
|
||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Molecular Expression Atlas (MEA) | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Drug-Drug Interaction (DDI) Information of This Drug
Coadministration of a Drug Treating the Disease Different from Bupropion (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 | 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. | ||||
3 | BDDCS applied to over 900 drugs | ||||
4 | Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds | ||||
5 | Nakamura K, Yokoi T, Inoue K, Shimada N, Ohashi N, Kume T, Kamataki T: CYP2D6 is the principal cytochrome P450 responsible for metabolism of the histamine H1 antagonist promethazine in human liver microsomes. Pharmacogenetics. 1996 Oct;6(5):449-57. | ||||
6 | 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 | ||||
7 | Clinically relevant drug interactions with new generation antidepressants and antipsychotics. Ther Umsch. 2009 Jun;66(6):485-92. | ||||
8 | Role of transporter-mediated efflux in the placental biodisposition of bupropion and its metabolite, OH-bupropion. Biochem Pharmacol. 2010 Oct 1;80(7):1080-6. | ||||
9 | Sertraline and its metabolite desmethylsertraline, but not bupropion or its three major metabolites, have high affinity for P-glycoprotein. Biol Pharm Bull. 2008 Feb;31(2):231-4. | ||||
10 | Validation of bupropion hydroxylation as a selective marker of human cytochrome P450 2B6 catalytic activity. Drug Metab Dispos. 2000 Oct;28(10):1222-30. | ||||
11 | In vitro to in vivo extrapolation of the complex drug-drug interaction of bupropion and its metabolites with CYP2D6; simultaneous reversible inhibition and CYP2D6 downregulation. Biochem Pharmacol. 2017 Jan 1;123:85-96. | ||||
12 | Product Monograph of Wellbutrin SR(Bupropion Hydrochloride). | ||||
13 | Laparoscopic Roux-en-Y gastric bypass surgery influenced pharmacokinetics of several drugs given as a cocktail with the highest impact observed for CYP1A2, CYP2C8 and CYP2E1 substrates. Basic Clin Pharmacol Toxicol. 2019 Aug;125(2):123-132. | ||||
14 | Inhibitory effects of anticancer drugs on dextromethorphan-O-demethylase activity in human liver microsomes. Cancer Chemother Pharmacol. 1993;32(6):491-5. | ||||
15 | 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. | ||||
16 | CYP2D6 polymorphisms and tamoxifen metabolism: clinical relevance. Curr Oncol Rep. 2010 Jan;12(1):7-15. | ||||
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 | 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. | ||||
19 | 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. | ||||
20 | Effects of propofol on human hepatic microsomal cytochrome P450 activities. Xenobiotica. 1998 Sep;28(9):845-53. | ||||
21 | Pharmacogenetics of schizophrenia. Am J Med Genet. 2000 Spring;97(1):98-106. | ||||
22 | Roles of CYP2A6 and CYP2B6 in nicotine C-oxidation by human liver microsomes. Arch Toxicol. 1999 Mar;73(2):65-70. | ||||
23 | Structure-activity relationship for human cytochrome P450 substrates and inhibitors. Drug Metab Rev. 2002 Feb-May;34(1-2):69-82. | ||||
24 | Chronic ethanol feeding and folate deficiency activate hepatic endoplasmic reticulum stress pathway in micropigs. Am J Physiol Gastrointest Liver Physiol. 2005 Jul;289(1):G54-63. | ||||
25 | Cytochrome P450 2E1 null mice provide novel protection against cisplatin-induced nephrotoxicity and apoptosis. Kidney Int. 2003 May;63(5):1687-96. | ||||
26 | Genotoxicity of tamoxifen, tamoxifen epoxide and toremifene in human lymphoblastoid cells containing human cytochrome P450s. Carcinogenesis. 1994 Jan;15(1):5-9. | ||||
27 | Acetaminophen induced acute liver failure via oxidative stress and JNK activation: protective role of taurine by the suppression of cytochrome P450 2E1. Free Radic Res. 2010 Mar;44(3):340-55. | ||||
28 | A study on the metabolism of etoposide and possible interactions with antitumor or supporting agents by human liver microsomes. J Pharmacol Exp Ther. 1998 Sep;286(3):1294-300. | ||||
29 | 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. | ||||
30 | Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448. | ||||
31 | Novel metabolic pathway of estrone and 17beta-estradiol catalyzed by cytochrome P-450. Drug Metab Dispos. 2000 Feb;28(2):110-2. | ||||
32 | Inhibition of cytochrome P450 2E1 by propofol in human and porcine liver microsomes. Biochem Pharmacol. 2002 Oct 1;64(7):1151-6. | ||||
33 | CYP2E1 and clinical features in alcoholics. Neuropsychobiology. 2003;47(2):86-9. | ||||
34 | 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. | ||||
35 | Tamoxifen inhibits cytochrome P450 2C9 activity in breast cancer patients. J Chemother. 2006 Aug;18(4):421-4. | ||||
36 | 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. | ||||
37 | Drug-drug interactions with imatinib: an observational study. Medicine (Baltimore). 2016 Oct;95(40):e5076. | ||||
38 | Drug interactions with calcium channel blockers: possible involvement of metabolite-intermediate complexation with CYP3A. Drug Metab Dispos. 2000 Feb;28(2):125-30. | ||||
39 | 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. | ||||
40 | A potential role for the estrogen-metabolizing cytochrome P450 enzymes in human breast carcinogenesis. Breast Cancer Res Treat. 2003 Dec;82(3):191-7. | ||||
41 | A mechanistic approach to antiepileptic drug interactions. Ann Pharmacother. 1998 May;32(5):554-63. | ||||
42 | Effect of tamoxifen on the enzymatic activity of human cytochrome CYP2B6. J Pharmacol Exp Ther. 2002 Jun;301(3):945-52. | ||||
43 | Hepatic metabolism of diclofenac: role of human CYP in the minor oxidative pathways. Biochem Pharmacol. 1999 Sep 1;58(5):787-96. | ||||
44 | Insights into CYP2B6-mediated drug-drug interactions. Acta Pharm Sin B. 2016 Sep;6(5):413-425. | ||||
45 | Drugs that may have potential CYP2B6 interactions. | ||||
46 | Involvement of human cytochrome P450 2B6 in the omega- and 4-hydroxylation of the anesthetic agent propofol. Xenobiotica. 2007 Jul;37(7):717-24. | ||||
47 | Nicotine and 4-(methylnitrosamino)-1-(3-pyridyl)-butanone metabolism by cytochrome P450 2B6. Drug Metab Dispos. 2005 Dec;33(12):1760-4. | ||||
48 | PharmGKB summary: phenytoin pathway. Pharmacogenet Genomics. 2012 Jun;22(6):466-70. | ||||
49 | 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. | ||||
50 | Human intestinal transporter database: QSAR modeling and virtual profiling of drug uptake, efflux and interactions. Pharm Res. 2013 Apr;30(4):996-1007. | ||||
51 | MDR1 (ABCB1) G1199A (Ser400Asn) polymorphism alters transepithelial permeability and sensitivity to anticancer agents. Cancer Chemother Pharmacol. 2009 Jun;64(1):183-8. | ||||
52 | 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. | ||||
53 | Folate transporter expression decreases in the human placenta throughout pregnancy and in pre-eclampsia. Pregnancy Hypertens. 2012 Apr;2(2):123-31. | ||||
54 | Comparative studies on in vitro methods for evaluating in vivo function of MDR1 P-glycoprotein. Pharm Res. 2001 Dec;18(12):1660-8. | ||||
55 | Antiestrogens and steroid hormones: substrates of the human P-glycoprotein. Biochem Pharmacol. 1994 Jul 19;48(2):287-92. | ||||
56 | 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. | ||||
57 | Doxorubicin transport by RALBP1 and ABCG2 in lung and breast cancer. Int J Oncol. 2007 Mar;30(3):717-25. | ||||
58 | Wild-type breast cancer resistance protein (BCRP/ABCG2) is a methotrexate polyglutamate transporter. Cancer Res. 2003 Sep 1;63(17):5538-43. | ||||
59 | The effect of low pH on breast cancer resistance protein (ABCG2)-mediated transport of methotrexate, 7-hydroxymethotrexate, methotrexate diglutamate, folic acid, mitoxantrone, topotecan, and resveratrol in in vitro drug transport models. Mol Pharmacol. 2007 Jan;71(1):240-9. | ||||
60 | Role of BCRP as a biomarker for predicting resistance to 5-fluorouracil in breast cancer. Cancer Chemother Pharmacol. 2009 May;63(6):1103-10. | ||||
61 | Inhibiting the function of ABCB1 and ABCG2 by the EGFR tyrosine kinase inhibitor AG1478. Biochem Pharmacol. 2009 Mar 1;77(5):781-93. | ||||
62 | Sterol transport by the human breast cancer resistance protein (ABCG2) expressed in Lactococcus lactis. J Biol Chem. 2003 Jun 6;278(23):20645-51. | ||||
63 | The phytoestrogen genistein enhances multidrug resistance in breast cancer cell lines by translational regulation of ABC transporters. Cancer Lett. 2016 Jun 28;376(1):165-72. | ||||
64 | Curcumin inhibits the activity of ABCG2/BCRP1, a multidrug resistance-linked ABC drug transporter in mice. Pharm Res. 2009 Feb;26(2):480-7. | ||||
65 | Imatinib mesylate (STI571) is a substrate for the breast cancer resistance protein (BCRP)/ABCG2 drug pump. Blood. 2004 Nov 1;104(9):2940-2. | ||||
66 | Augmentation effect of combination therapy of aripiprazole and antidepressants on forced swimming test in mice. Psychopharmacology (Berl). 2009 Sep;206(1):97-107. | ||||
67 | Treatment of comorbid pain with serotonin norepinephrine reuptake inhibitors. CNS Spectr. 2008 Jul;13(7 Suppl 11):22-6. | ||||
68 | Invivo antioxidant status: a putative target of antidepressant action. Prog Neuropsychopharmacol Biol Psychiatry. 2009 Mar 17;33(2):220-8. | ||||
69 | Differential involvement of the norepinephrine, serotonin and dopamine reuptake transporter proteins in cocaine-induced taste aversion. Pharmacol Biochem Behav. 2009 Jul;93(1):75-81. | ||||
70 | 2008 FDA drug approvals. Nat Rev Drug Discov. 2009 Feb;8(2):93-6. | ||||
71 | Antidepressants suppress production of the Th1 cytokine interferon-gamma, independent of monoamine transporter blockade. Eur Neuropsychopharmacol. 2006 Oct;16(7):481-90. | ||||
72 | Multi-target therapeutics: when the whole is greater than the sum of the parts. Drug Discov Today. 2007 Jan;12(1-2):34-42. | ||||
73 | Hughes B: 2009 FDA drug approvals. Nat Rev Drug Discov. 2010 Feb;9(2):89-92. | ||||
74 | Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services. | ||||
75 | Radium 223 dichloride for prostate cancer treatment. Drug Des Devel Ther. 2017 Sep 6;11:2643-2651. | ||||
76 | Psychopharmacological treatment of dermatological patients--when simply talking does not help. J Dtsch Dermatol Ges. 2007 Dec;5(12):1101-6. | ||||
77 | Cerner Multum, Inc. "Australian Product Information.". | ||||
78 | Boyer EW, Shannon M "The serotonin syndrome." N Engl J Med 352 (2005): 1112-20. [PMID: 15784664] | ||||
79 | Product Information. Wellbutrin XL (buPROPion). GlaxoSmithKline, Philadelphia, PA. | ||||
80 | Product Information. Olinvyk (oliceridine). Trevena Inc, Chesterbrook, PA. | ||||
81 | Product Information. Sirturo (bedaquiline). Janssen Pharmaceuticals, Titusville, NJ. | ||||
82 | Sheehan DV, Welch JB, Fishman SM "A case of bupropion-induced seizure." J Nerv Ment Dis 174 (1986): 496-8. [PMID: 3090199] | ||||
83 | Product Information. Turalio (pexidartinib). Daiichi Sankyo, Inc., Parsippany, NJ. | ||||
84 | Cerner Multum, Inc. "UK Summary of Product Characteristics.". | ||||
85 | Agencia Espaola de Medicamentos y Productos Sanitarios Healthcare "Centro de informacion online de medicamentos de la AEMPS - CIMA.". | ||||
86 | Cerner Multum, Inc. "Canadian Product Information.". | ||||
87 | Product Information. Brintellix (vortioxetine). Takeda Pharmaceuticals America, Lincolnshire, IL. | ||||
88 | De Vita VT, Hahn MA, Oliverio VT "Monoamine oxidase inhibition by a new carcinostatic agent, n-isopropyl-a-(2-methylhydrazino)-p-toluamide (MIH). (30590)." Proc Soc Exp Biol Med 120 (1965): 561-5. [PMID: 4379192] | ||||
89 | Product Information. Rexulti (brexpiprazole). Otsuka American Pharmaceuticals Inc, Rockville, MD. | ||||
90 | Canadian Pharmacists Association. | ||||
91 | Product Information. Xenazine (tetrabenazine). Prestwick Pharmaceuticals Inc, Washington DC, VA. | ||||
92 | Product Information. Austedo (deutetrabenazine). Teva Pharmaceuticals USA, North Wales, PA. | ||||
93 | Product Information. Ingrezza (valbenazine). Neurocrine Biosciences, Inc., San Diego, CA. | ||||
94 | Product Information. Xcopri (cenobamate). SK Life Science, Inc., Paramus, NJ. | ||||
95 | James WA, Lippmann S "Bupropion: overview and prescribing guidelines in depression." South Med J 84 (1991): 222-4. [PMID: 1899294] | ||||
96 | Product Information. Adcetris (brentuximab vedotin). Seattle Genetics Inc, Bothell, WA. | ||||
97 | Product Information. Juxtapid (lomitapide). Aegerion Pharmaceuticals Inc, Cambridge, MA. | ||||
98 | Dufresne RL, Weber SS, Becker RE "Bupropion hydrochloride." Drug Intell Clin Pharm 18 (1984): 957-64. [PMID: 6439541] | ||||
99 | Product Information. Suprep Bowel Prep Kit (magnesium/potassium/sodium sulfates). Braintree Laboratories, Braintree, MA. | ||||
100 | Product Information. Viberzi (eluxadoline). Actavis Pharma, Inc., Parsippany, NJ. | ||||
101 | Al-Nawakil C, Willems L, Mauprivez C, et.al "Successful treatment of l-asparaginase-induced severe acute hepatotoxicity using mitochondrial cofactors." Leuk Lymphoma 55 (2014): 1670-4. [PMID: 24090500] | ||||
102 | Product Information. Zydelig (idelalisib). Gilead Sciences, Foster City, CA. | ||||
103 | Product Information. Zulresso (brexanolone). Sage Therapeutics, Inc., Cambridge, MA. | ||||
104 | Product Information. Reyvow (lasmiditan). Lilly, Eli and Company, Indianapolis, IN. | ||||
105 | Product Information. Addyi (flibanserin). Sprout Pharmaceuticals, Raleigh, NC. | ||||
106 | Product Information. Belviq (lorcaserin). Eisai Inc, Teaneck, NJ. | ||||
107 | Product Information. Xeglyze (abametapir topical). Dr. Reddy's Laboratories Inc, Upper Saddle River, NJ. | ||||