Details of the Drug
General Information of Drug (ID: DMIK367)
Drug Name |
Procarbazine
|
|||||||||||||||||||
---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
Synonyms |
Ibenzmethyzin; Ibenzmethyzine; MBH; MIH; Natulan; Natulanar; PCX; Procarbazin; Procarbazina; Procarbazinum; Procarbazin [German]; Procarbazine Monohydrochloride; CB 400-497; Indicarb (TN); Matulane (TN); Natulan (TN); Procarbazina [INN-Spanish]; Procarbazine (INN); Procarbazine [INN:BAN]; Procarbazinum [INN-Latin];Ro 4-6467; SRI-10847; Ro 4-6467/1; N-4-Isopropylcarbamoylbenzyl-N'-methylhydrazine; N-Isopropyl-4-[(2-methylhydrazino)methyl]benzamide; P-(2-Methylhydrazinomethyl)-N-isopropylbenzamide; N-Isopropyl-p-(2-methylhydrazinomethyl)-benzamide; P-(N'-Methylhydrazinomethyl)-N-isopropylbenzamide; N-(1-Methylethyl)-4-[(2-methylhydrazino)methyl]benzamide; N-Isopropyl-alpha-(2-methylhydrazino)-p-toluamide; N-(1-Methylethyl)-4-((2-methylhydrazino)methyl)benzamide; Benzamide, N-(1-methylethyl)-4-((2-methylhydrazino)methyl)-(9CI); 1-Methyl-2-(p-(isopropylcarbamoyl)benzyl)hydrazine; 2-(p-Isopropylcarbamoylbenzyl)-1-methylhydrazine; 4-((2-Methylhydrazino)methyl)-N-isopropylbenzamide; 4-[(2-methylhydrazinyl)methyl]-N-propan-2-ylbenzamide
|
|||||||||||||||||||
Indication |
|
|||||||||||||||||||
Therapeutic Class |
Anticancer Agents
|
|||||||||||||||||||
Drug Type |
Small molecular drug
|
|||||||||||||||||||
Structure | ||||||||||||||||||||
3D MOL | 2D MOL | |||||||||||||||||||
#Ro5 Violations (Lipinski): 0 | Molecular Weight (mw) | 221.3 | ||||||||||||||||||
Topological Polar Surface Area (xlogp) | 0.1 | |||||||||||||||||||
Rotatable Bond Count (rotbonds) | 5 | |||||||||||||||||||
Hydrogen Bond Donor Count (hbonddonor) | 3 | |||||||||||||||||||
Hydrogen Bond Acceptor Count (hbondacc) | 3 | |||||||||||||||||||
ADMET Property |
|
|||||||||||||||||||
Chemical Identifiers |
|
|||||||||||||||||||
Cross-matching ID | ||||||||||||||||||||
Molecular Interaction Atlas of This Drug
Drug Therapeutic Target (DTT) |
|
||||||||||||||||||||||||||||||||||||
---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
Drug-Metabolizing Enzyme (DME) |
|
||||||||||||||||||||||||||||||||||||
Molecular Interaction Atlas (MIA) | |||||||||||||||||||||||||||||||||||||
Drug-Drug Interaction (DDI) Information of This Drug
Coadministration of a Drug Treating the Disease Different from Procarbazine (Comorbidity)
|
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: 7278). | ||||
---|---|---|---|---|---|
2 | FDA Approved Drug Products from FDA Official Website. 2009. Application Number: (NDA) 016785. | ||||
3 | 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. | ||||
4 | Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds | ||||
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 | Brca2/Xrcc2 dependent HR, but not NHEJ, is required for protection against O(6)-methylguanine triggered apoptosis, DSBs and chromosomal aberrations... DNA Repair (Amst). 2009 Jan 1;8(1):72-86. | ||||
7 | In vitro and in vivo evidence for the formation of methyl radical from procarbazine: a spin-trapping study. Carcinogenesis. 1992 May;13(5):799-805. | ||||
8 | Tumour cytochrome P450 and drug activation. Curr Pharm Des. 2002;8(15):1335-47. | ||||
9 | 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. | ||||
10 | 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. | ||||
11 | Endoxifen and other metabolites of tamoxifen inhibit human hydroxysteroid sulfotransferase 2A1 (hSULT2A1). Drug Metab Dispos. 2014 Nov;42(11):1843-50. | ||||
12 | Cytochrome P450 1A2 (CYP1A2) activity and risk factors for breast cancer: a cross-sectional study. Breast Cancer Res. 2004;6(4):R352-65. | ||||
13 | PharmGKB summary: pathways of acetaminophen metabolism at the therapeutic versus toxic doses. Pharmacogenet Genomics. 2015 Aug;25(8):416-26. | ||||
14 | The effect of apigenin on pharmacokinetics of imatinib and its metabolite N-desmethyl imatinib in rats. Biomed Res Int. 2013;2013:789184. | ||||
15 | Effects of morin on the pharmacokinetics of etoposide in rats. Biopharm Drug Dispos. 2007 Apr;28(3):151-6. | ||||
16 | 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. | ||||
17 | Identification of P450 enzymes involved in metabolism of verapamil in humans. Naunyn Schmiedebergs Arch Pharmacol. 1993 Sep;348(3):332-7. | ||||
18 | Metabolism and metabolic inhibition of xanthotoxol in human liver microsomes. Evid Based Complement Alternat Med. 2016;2016:5416509. | ||||
19 | Allelic variants of human cytochrome P450 1A1 (CYP1A1): effect of T461N and I462V substitutions on steroid hydroxylase specificity. Pharmacogenetics. 2000 Aug;10(6):519-30. | ||||
20 | Metabolism of tamoxifen by recombinant human cytochrome P450 enzymes: formation of the 4-hydroxy, 4'-hydroxy and N-desmethyl metabolites and isomerization of trans-4-hydroxytamoxifen. Drug Metab Dispos. 2002 Aug;30(8):869-74. | ||||
21 | Cytochrome P450 isoforms catalyze formation of catechol estrogen quinones that react with DNA. Metabolism. 2007 Jul;56(7):887-94. | ||||
22 | Preferred orientations in the binding of 4'-hydroxyacetanilide (acetaminophen) to cytochrome P450 1A1 and 2B1 isoforms as determined by 13C- and 15N-NMR relaxation studies. J Med Chem. 1994 Mar 18;37(6):860-7. | ||||
23 | 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. | ||||
24 | A common CYP1B1 polymorphism is associated with 2-OHE1/16-OHE1 urinary estrone ratio. Clin Chem Lab Med. 2005;43(7):702-6. | ||||
25 | Cytochromes P450 in crustacea. Comp Biochem Physiol C Pharmacol Toxicol Endocrinol. 1998 Nov;121(1-3):157-72. | ||||
26 | Disruption of endogenous regulator homeostasis underlies the mechanism of rat CYP1A1 mRNA induction by metyrapone. Biochem J. 1998 Apr 1;331 ( Pt 1):273-81. | ||||
27 | Pharmacogenomics in drug-metabolizing enzymes catalyzing anticancer drugs for personalized cancer chemotherapy. Curr Drug Metab. 2007 Aug;8(6):554-62. | ||||
28 | Catalytic properties of polymorphic human cytochrome P450 1B1 variants. Carcinogenesis. 1999 Aug;20(8):1607-13. | ||||
29 | Pharmacokinetics of rosuvastatin when coadministered with rifampicin in healthy males: a randomized, single-blind, placebo-controlled, crossover study. Clin Ther. 2008 Jul;30(7):1283-9. | ||||
30 | Metabolism of retinoids and arachidonic acid by human and mouse cytochrome P450 1b1. Drug Metab Dispos. 2004 Aug;32(8):840-7. | ||||
31 | Oxidation of xenobiotics by recombinant human cytochrome P450 1B1. Drug Metab Dispos. 1997 May;25(5):617-22. | ||||
32 | Metabolism of melatonin by human cytochromes p450. Drug Metab Dispos. 2005 Apr;33(4):489-94. | ||||
33 | Cisplatin and DNA repair in cancer chemotherapy.Trends Biochem Sci.1995 Oct;20(10):435-9. | ||||
34 | Structures of oxaliplatin-oligonucleotide adducts from DNA.J Mass Spectrom.2012 Oct;47(10):1282-93. | ||||
35 | 31P NMR spectra of ethidium, quinacrine, and daunomycin complexes with poly(adenylic acid).poly(uridylic acid) RNA duplex and calf thymus DNA. Biochemistry. 1989 Apr 4;28(7):2804-12. | ||||
36 | Pharmacokinetics and metabolism of ifosfamide in relation to DNA damage assessed by the COMET assay in children with cancer. Br J Cancer. 2005 May 9;92(9):1626-35. | ||||
37 | O6-methylguanine-DNA methyltransferase activity and sensitivity to cyclophosphamide and cisplatin in human lung tumor xenografts. Int J Cancer. 1998 Sep 11;77(6):919-22. | ||||
38 | Inhibition of carboplatin-induced DNA interstrand cross-link repair by gemcitabine in patients receiving these drugs for platinum-resistant ovarian cancer.Clin Cancer Res.2010 Oct 1;16(19):4899-905. | ||||
39 | DNA intrastrand cross-link at the 5'-GA-3' sequence formed by busulfan and its role in the cytotoxic effect. Cancer Sci. 2004 May;95(5):454-8. | ||||
40 | Structural studies of atom-specific anticancer drugs acting on DNA. Pharmacol Ther. 1999 Sep;83(3):181-215. | ||||
41 | Predicting the myelotoxicity of chemotherapy: the use of pretreatment O6-methylguanine-DNA methyltransferase determination in peripheral blood mono... Melanoma Res. 2011 Dec;21(6):502-8. | ||||
42 | Alkylation of DNA by melphalan in relation to immunoassay of melphalan-DNA adducts: characterization of mono-alkylated and cross-linked products fr... Chem Biol Interact. 1990;73(2-3):183-94. | ||||
43 | Canadian Pharmacists Association. | ||||
44 | Ban TA "Drug interactions with psychoactive drugs." Dis Nerv Syst 36 (1975): 164-6. [PMID: 1116424] | ||||
45 | Boakes AJ, Laurence DR, Teoh PC, Barar FS, Benedikter LT, Prichard BN "Interactions between sympathomimetic amines and antidepressant agents in man." Br Med J 1 (1973): 311-5. [PMID: 4685619] | ||||
46 | Adverse effects and complications of treatment with beta-adrenergic agonist drugs. Committee on drugs, the American Academy of Allergy and Immunology. J Allergy Clin Immunol 75 (1985): 443-9. [PMID: 2858503] | ||||
47 | Cerner Multum, Inc. "UK Summary of Product Characteristics.". | ||||
48 | Product Information. Northera (droxidopa). Chelsea Therapeutics Inc, Charlotte, NC. | ||||
49 | Johnson EJ, MacGowan AP, Potter MN, et al "Reduced absorption of oral ciprofloxacin after chemotherapy for haematological malignancy." J Antimicrob Chemother 25 (1990): 837-42. [PMID: 2373666] | ||||
50 | Alvine G, Black DW, Tsuang D "Case of delirium secondary to phenelzine/L-tryptophan combination." J Clin Psychiatry 51 (1990): 311. [PMID: 2365671] | ||||
51 | Bazire SR "Sudden death associated with switching monoamine oxidase inhibitors." Drug Intell Clin Pharm 20 (1986): 954-6. [PMID: 3816543] | ||||
52 | Beasley CM Jr, Masica DN, Heiligenstein JH, Wheadon DE, Zerbe RL "Possible monoamine oxidase inhibitor-serotonin uptake inhibitor interaction: fluoxetine clinical data and preclinical findings." J Clin Psychopharmacol 13 (1993): 312-20. [PMID: 8227489] | ||||
53 | Boyer EW, Shannon M "The serotonin syndrome." N Engl J Med 352 (2005): 1112-20. [PMID: 15784664] | ||||
54 | Graber MA, Hoehns TB, Perry PJ "Sertraline-phenelzine drug interaction: a serotonin syndrome reaction." Ann Pharmacother 28 (1994): 732-5. [PMID: 7919561] | ||||
55 | Goldberg LI "Monoamine oxidase inhibitors: adverse reactions and possible mechanisms." JAMA 190 (1964): 456-62. [PMID: 14197995] | ||||
56 | Product Information. Austedo (deutetrabenazine). Teva Pharmaceuticals USA, North Wales, PA. | ||||
57 | Darcy PF, Griffin JP "Interactions with drugs used in the treatment of depressive illness." Adverse Drug React Toxicol Rev 14 (1995): 211-31. [PMID: 8845455] | ||||
58 | Cusson JR, Goldenberg E, Larochelle P "Effect of a novel monoamine-oxidase inhibitor, moclobemide on the sensitivity to intravenous tyramine and norepinephrine in humans." J Clin Pharmacol 31 (1991): 462-7. [PMID: 2050833] | ||||
59 | Product Information. Arava (leflunomide). Hoechst Marion-Roussel Inc, Kansas City, MO. | ||||
60 | Product Information. Prolia (denosumab). Amgen USA, Thousand Oaks, CA. | ||||
61 | Product Information. Zulresso (brexanolone). Sage Therapeutics, Inc., Cambridge, MA. | ||||
62 | Product Information. Vumerity (diroximel fumarate). Alkermes, Inc, Cambridge, MA. | ||||
63 | Cerner Multum, Inc. "Australian Product Information.". | ||||
64 | Product Information. Gilenya (fingolimod). Novartis Pharmaceuticals, East Hanover, NJ. | ||||
65 | Product Information. Ocrevus (ocrelizumab). Genentech, South San Francisco, CA. | ||||
66 | Product Information. Zeposia (ozanimod). Celgene Corporation, Summit, NJ. | ||||
67 | Product Information. Synribo (omacetaxine). Teva Pharmaceuticals USA, North Wales, PA. | ||||
68 | Filibeck DJ, Grimm D, Forman WB, Leidner BA "Metoclopramide-induced hypertensive crisis." Clin Pharm 3 (1984): 548-9. [PMID: 6541544] | ||||
69 | Product Information. Belviq (lorcaserin). Eisai Inc, Teaneck, NJ. | ||||
70 | Boakes AJ, Laurence DR, Teoh PC, Barar FS, Benedikter LT, Pritchard BN "Interactions between sympathomimetic amines and antidepressant agents in man." Br Med J 1 (1973): 311-5. [PMID: 4685619] | ||||
71 | Product Information. Arcalyst (rilonacept). Regeneron Pharmaceuticals Inc, Tarrytown, NY. | ||||
72 | Product Information. Cimzia (certolizumab). UCB Pharma Inc, Smyrna, GA. | ||||
73 | CDC. Centers for Disease Control and Prevention/ "Recommendations of the advisory committtee on immunization practices (ACIP): use of vaccines and immune globulins in persons with altered immunocompetence." MMWR Morb Mortal Wkly Rep 42(RR-04) (1993): 1-18. [PMID: 20300058] | ||||