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
Disease Entry ICD 11 Status REF
Hodgkin lymphoma 2B30 Approved [1]
Therapeutic Class
Anticancer Agents
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 221.3
Logarithm of the Partition Coefficient (xlogp) 0.1
Rotatable Bond Count (rotbonds) 5
Hydrogen Bond Donor Count (hbonddonor) 3
Hydrogen Bond Acceptor Count (hbondacc) 3
ADMET Property
Absorption
The drug is rapidly and completely absorbed []
Half-life
The concentration or amount of drug in body reduced by one-half in 10 minutes [2]
Metabolism
The drug is metabolized via the liver []
MRTD
The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 27.11194 micromolar/kg/day [3]
Chemical Identifiers
Formula
C12H19N3O
IUPAC Name
4-[(2-methylhydrazinyl)methyl]-N-propan-2-ylbenzamide
Canonical SMILES
CC(C)NC(=O)C1=CC=C(C=C1)CNNC
InChI
InChI=1S/C12H19N3O/c1-9(2)15-12(16)11-6-4-10(5-7-11)8-14-13-3/h4-7,9,13-14H,8H2,1-3H3,(H,15,16)
InChIKey
CPTBDICYNRMXFX-UHFFFAOYSA-N
Cross-matching ID
PubChem CID
4915
ChEBI ID
CHEBI:71417
CAS Number
671-16-9
DrugBank ID
DB01168
TTD ID
D08GYO
INTEDE ID
DR1344
ACDINA ID
D00558
Combinatorial Drugs (CBD) Click to Jump to the Detailed CBD Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Human Deoxyribonucleic acid (hDNA) TTUTN1I NOUNIPROTAC Not Available [4]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 1A1 (CYP1A1) DE6OQ3W CP1A1_HUMAN Substrate [5]
Cytochrome P450 1A2 (CYP1A2) DEJGDUW CP1A2_HUMAN Substrate [5]
Cytochrome P450 1B1 (CYP1B1) DE9QHP6 CP1B1_HUMAN Substrate [6]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Disease Different from Procarbazine (Comorbidity)
DDI Drug Name DDI Drug ID Severity Mechanism Comorbidity REF
Mepyramine DMB4SFH Moderate Additive CNS depression effects by the combination of Procarbazine and Mepyramine. Allergic/hypersensitivity disorder [4A80-4A8Z] [7]
Phenyltoloxamine DMKAEQW Moderate Additive CNS depression effects by the combination of Procarbazine and Phenyltoloxamine. Allergic/hypersensitivity disorder [4A80-4A8Z] [7]
Amyl nitrite DMJKO05 Moderate Additive hypotensive effects by the combination of Procarbazine and Amyl nitrite. Angina pectoris [BA40] [8]
Levalbuterol DM5YBO1 Moderate Additive hypertensive effects by the combination of Procarbazine and Levalbuterol. Asthma [CA23] [9]
Pirbuterol DMI5678 Moderate Additive hypertensive effects by the combination of Procarbazine and Pirbuterol. Asthma [CA23] [10]
Ephedrine DMMV0KW Major Additive hypertensive effects by the combination of Procarbazine and Ephedrine. Asthma [CA23] [8]
Roflumilast DMPGHY8 Moderate Additive immunosuppressive effects by the combination of Procarbazine and Roflumilast. Asthma [CA23] [11]
Lisdexamfetamine DM6W8V5 Major Increased risk of hyperpyrexia by the combination of Procarbazine and Lisdexamfetamine. Attention deficit hyperactivity disorder [6A05] [8]
Droxidopa DM5YF4M Moderate Additive hypertensive effects by the combination of Procarbazine and Droxidopa. Autonomic nervous system disorder [8D87] [12]
Sparfloxacin DMB4HCT Minor Decreased absorption of Procarbazine due to intestinal mucosa variation caused by Sparfloxacin. Bacterial infection [1A00-1C4Z] [13]
ABT-492 DMJFD2I Minor Decreased absorption of Procarbazine due to intestinal mucosa variation caused by ABT-492. Bacterial infection [1A00-1C4Z] [13]
Olodaterol DM62B78 Moderate Additive hypertensive effects by the combination of Procarbazine and Olodaterol. Chronic obstructive pulmonary disease [CA22] [10]
Vilanterol DMF5EK1 Moderate Additive hypertensive effects by the combination of Procarbazine and Vilanterol. Chronic obstructive pulmonary disease [CA22] [9]
Indacaterol DMQJHR7 Moderate Additive hypertensive effects by the combination of Procarbazine and Indacaterol. Chronic obstructive pulmonary disease [CA22] [10]
Arformoterol DMYM974 Moderate Additive hypertensive effects by the combination of Procarbazine and Arformoterol. Chronic obstructive pulmonary disease [CA22] [10]
Levomilnacipran DMV26S8 Major Additive serotonergic effects by the combination of Procarbazine and Levomilnacipran. Chronic pain [MG30] [14]
Cyclandelate DMO0R76 Moderate Additive hypotensive effects by the combination of Procarbazine and Cyclandelate. Dementia [6D80-6D8Z] [8]
Isocarboxazid DMAF1NB Major Additive hypertensive effects by the combination of Procarbazine and Isocarboxazid. Depression [6A70-6A7Z] [15]
Milnacipran DMBFE74 Major Additive serotonergic effects by the combination of Procarbazine and Milnacipran. Depression [6A70-6A7Z] [14]
Escitalopram DMFK9HG Major Additive serotonergic effects by the combination of Procarbazine and Escitalopram. Depression [6A70-6A7Z] [16]
Desvenlafaxine DMHD4PE Major Additive serotonergic effects by the combination of Procarbazine and Desvenlafaxine. Depression [6A70-6A7Z] [14]
Clomipramine DMINRKW Major Additive serotonergic effects by the combination of Procarbazine and Clomipramine. Depression [6A70-6A7Z] [17]
5-hydroxy-L-tryptophan DMDWZGJ Major Additive serotonergic effects by the combination of Procarbazine and 5-hydroxy-L-tryptophan. Discovery agent [N.A.] [18]
LEVONORDEFRIN DMWDJ0H Moderate Additive hypertensive effects by the combination of Procarbazine and LEVONORDEFRIN. Discovery agent [N.A.] [19]
Tetrabenazine DMYWQ0O Major Additive hypertensive effects by the combination of Procarbazine and Tetrabenazine. Dissociative neurological symptom disorder [6B60] [20]
Deutetrabenazine DMUPFLI Major Additive hypertensive effects by the combination of Procarbazine and Deutetrabenazine. Dystonic disorder [8A02] [20]
Guanethidine DM9NSWT Moderate Antagonize the effect of Procarbazine when combined with Guanethidine. Essential hypertension [BA00] [21]
Mephentermine DMFJH5Q Major Additive hypertensive effects by the combination of Procarbazine and Mephentermine. Essential hypertension [BA00] [8]
Nesiritide DMFOIA8 Moderate Additive hypotensive effects by the combination of Procarbazine and Nesiritide. Heart failure [BD10-BD1Z] [8]
Tetrahydrozoline DMT57WC Moderate Decreased metabolism of Procarbazine caused by Tetrahydrozoline mediated inhibition of non-CYP450 enzyme. Herpes simplex infection [1F00] [22]
Maraviroc DMTL94F Moderate Additive hypotensive effects by the combination of Procarbazine and Maraviroc. Human immunodeficiency virus disease [1C60-1C62] [8]
Teriflunomide DMQ2FKJ Major Additive immunosuppressive effects by the combination of Procarbazine and Teriflunomide. Hyper-lipoproteinaemia [5C80] [23]
Aliskiren DM1BV7W Moderate Additive hypotensive effects by the combination of Procarbazine and Aliskiren. Hypertension [BA00-BA04] [8]
Captopril DM458UM Moderate Additive hypotensive effects by the combination of Procarbazine and Captopril. Hypertension [BA00-BA04] [8]
Levamlodipine DM92S6N Moderate Additive hypotensive effects by the combination of Procarbazine and Levamlodipine. Hypertension [BA00-BA04] [8]
TAK-491 DMCF6SX Moderate Additive hypotensive effects by the combination of Procarbazine and TAK-491. Hypertension [BA00-BA04] [8]
Clevidipine butyrate DMW4M97 Moderate Additive hypotensive effects by the combination of Procarbazine and Clevidipine butyrate. Hypertension [BA00-BA04] [8]
Naphazoline DMJFZDL Moderate Decreased metabolism of Procarbazine caused by Naphazoline mediated inhibition of non-CYP450 enzyme. Itching [1F28-1G07] [22]
Denosumab DMNI0KO Moderate Additive myelosuppressive effects by the combination of Procarbazine and Denosumab. Low bone mass disorder [FB83] [24]
Allopregnanolone DMNLHAC Moderate Additive CNS depression effects by the combination of Procarbazine and Allopregnanolone. Mental/behavioural/neurodevelopmental disorder [6E20-6E8Z] [25]
Lasmiditan DMXLVDT Major Additive serotonergic effects by the combination of Procarbazine and Lasmiditan. Migraine [8A80] [14]
Tecfidera DM2OVDT Moderate Additive immunosuppressive effects by the combination of Procarbazine and Tecfidera. Multiple sclerosis [8A40] [26]
Siponimod DM2R86O Major Additive immunosuppressive effects by the combination of Procarbazine and Siponimod. Multiple sclerosis [8A40] [27]
Fingolimod DM5JVAN Major Additive immunosuppressive effects by the combination of Procarbazine and Fingolimod. Multiple sclerosis [8A40] [28]
Ocrelizumab DMEZ2KH Moderate Additive immunosuppressive effects by the combination of Procarbazine and Ocrelizumab. Multiple sclerosis [8A40] [29]
Ozanimod DMT6AM2 Major Decreased metabolism of Procarbazine caused by Ozanimod mediated inhibition of non-CYP450 enzyme. Multiple sclerosis [8A40] [30]
Omacetaxine mepesuccinate DMPU2WX Moderate Additive immunosuppressive effects by the combination of Procarbazine and Omacetaxine mepesuccinate. Myeloproliferative neoplasm [2A20] [31]
Dextroamphetamine DMMIHVP Major Increased risk of hyperpyrexia by the combination of Procarbazine and Dextroamphetamine. Narcolepsy [7A20] [8]
Phenindamine DMDTC7R Moderate Additive CNS depression effects by the combination of Procarbazine and Phenindamine. Nasopharyngitis [CA00] [7]
Cyclizine DM9G7BS Moderate Additive CNS depression effects by the combination of Procarbazine and Cyclizine. Nausea/vomiting [MD90] [7]
Metoclopramide DMFA5MY Moderate Additive hypertensive effects by the combination of Procarbazine and Metoclopramide. Nausea/vomiting [MD90] [32]
Phendimetrazine DM6TS1N Major Increased risk of hyperpyrexia by the combination of Procarbazine and Phendimetrazine. Obesity [5B80-5B81] [8]
Lorcaserin DMG6OYJ Major Additive serotonergic effects by the combination of Procarbazine and Lorcaserin. Obesity [5B80-5B81] [33]
Dexfenfluramine DMJ7YDS Major Additive serotonergic effects by the combination of Procarbazine and Dexfenfluramine. Obesity [5B80-5B81] [14]
Propylhexedrine DMTBW2O Moderate Decreased metabolism of Procarbazine caused by Propylhexedrine mediated inhibition of non-CYP450 enzyme. Obesity [5B80-5B81] [22]
Polythiazide DMCH80F Moderate Additive hypotensive effects by the combination of Procarbazine and Polythiazide. Oedema [MG29] [8]
Lofexidine DM1WXA6 Moderate Additive hypotensive effects by the combination of Procarbazine and Lofexidine. Opioid use disorder [6C43] [8]
Methamphetamine DMPM4SK Major Increased risk of hyperpyrexia by the combination of Procarbazine and Methamphetamine. Pain [MG30-MG3Z] [34]
Levodopa DMN3E57 Major Additive hypertensive effects by the combination of Procarbazine and Levodopa. Parkinsonism [8A00] [8]
Silodosin DMJSBT6 Moderate Additive hypotensive effects by the combination of Procarbazine and Silodosin. Prostate hyperplasia [GA90] [8]
Levomepromazine DMIKFEL Moderate Additive hypotensive effects by the combination of Procarbazine and Levomepromazine. Psychotic disorder [6A20-6A25] [8]
Selexipag DMAHSU0 Moderate Additive hypotensive effects by the combination of Procarbazine and Selexipag. Pulmonary hypertension [BB01] [8]
Epoprostenol DMUTYR2 Moderate Additive hypotensive effects by the combination of Procarbazine and Epoprostenol. Pulmonary hypertension [BB01] [8]
Canakinumab DM8HLO5 Moderate Additive immunosuppressive effects by the combination of Procarbazine and Canakinumab. Rheumatoid arthritis [FA20] [35]
Rilonacept DMGLUQS Moderate Additive immunosuppressive effects by the combination of Procarbazine and Rilonacept. Rheumatoid arthritis [FA20] [35]
Golimumab DMHZV7X Major Additive immunosuppressive effects by the combination of Procarbazine and Golimumab. Rheumatoid arthritis [FA20] [36]
Anthrax vaccine DM9GSWY Moderate Antagonize the effect of Procarbazine when combined with Anthrax vaccine. Sepsis [1G40-1G41] [37]
Avanafil DM75CXN Moderate Additive hypotensive effects by the combination of Procarbazine and Avanafil. Sexual dysfunction [HA00-HA01] [8]
Trimeprazine DMEMV9D Moderate Additive hypotensive effects by the combination of Procarbazine and Trimeprazine. Vasomotor/allergic rhinitis [CA08] [19]
Xylometazoline DMKV32D Moderate Decreased metabolism of Procarbazine caused by Xylometazoline mediated inhibition of non-CYP450 enzyme. Vasomotor/allergic rhinitis [CA08] [22]
Acrivastine DMTIGA0 Moderate Additive CNS depression effects by the combination of Procarbazine and Acrivastine. Vasomotor/allergic rhinitis [CA08] [7]
Valganciclovir DMS2IUH Moderate Additive myelosuppressive effects by the combination of Procarbazine and Valganciclovir. Virus infection [1A24-1D9Z] [27]
⏷ Show the Full List of 72 DDI Information of This Drug

Drug Inactive Ingredient(s) (DIG) and Formulation(s) of This Drug

DIG
DIG Name DIG ID PubChem CID Functional Classification
Mannitol E00103 6251 Diluent; Flavoring agent; Lyophilization aid; Plasticizing agent; Tonicity agent
methylparaben E00149 7456 Antimicrobial preservative
Propyl 4-hydroxybenzoate E00141 7175 Antimicrobial preservative
Quinoline yellow WS E00309 24671 Colorant
Sunset yellow FCF E00255 17730 Colorant
Gelatin E00630 Not Available Other agent
Potassium sorbate E00566 23676745 Antimicrobial preservative
Talc E00520 16211421 Anticaking agent; Diluent; Glidant; lubricant
Titanium dioxide E00322 26042 Coating agent; Colorant; Opacifying agent
⏷ Show the Full List of 9 Pharmaceutical Excipients of This Drug
Pharmaceutical Formulation
Formulation Name Drug Dosage Dosage Form Route
Procarbazine 50 mg capsule 50 mg Oral Capsule Oral
Procarbazine Hydrochloride 50mg capsule 50mg Capsule Oral
Jump to Detail Pharmaceutical Formulation Page 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 Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
3 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
4 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.
5 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.
6 Tumour cytochrome P450 and drug activation. Curr Pharm Des. 2002;8(15):1335-47.
7 Canadian Pharmacists Association.
8 Ban TA "Drug interactions with psychoactive drugs." Dis Nerv Syst 36 (1975): 164-6. [PMID: 1116424]
9 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]
10 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]
11 Cerner Multum, Inc. "UK Summary of Product Characteristics.".
12 Product Information. Northera (droxidopa). Chelsea Therapeutics Inc, Charlotte, NC.
13 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]
14 Alvine G, Black DW, Tsuang D "Case of delirium secondary to phenelzine/L-tryptophan combination." J Clin Psychiatry 51 (1990): 311. [PMID: 2365671]
15 Bazire SR "Sudden death associated with switching monoamine oxidase inhibitors." Drug Intell Clin Pharm 20 (1986): 954-6. [PMID: 3816543]
16 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]
17 Boyer EW, Shannon M "The serotonin syndrome." N Engl J Med 352 (2005): 1112-20. [PMID: 15784664]
18 Graber MA, Hoehns TB, Perry PJ "Sertraline-phenelzine drug interaction: a serotonin syndrome reaction." Ann Pharmacother 28 (1994): 732-5. [PMID: 7919561]
19 Goldberg LI "Monoamine oxidase inhibitors: adverse reactions and possible mechanisms." JAMA 190 (1964): 456-62. [PMID: 14197995]
20 Product Information. Austedo (deutetrabenazine). Teva Pharmaceuticals USA, North Wales, PA.
21 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]
22 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]
23 Product Information. Arava (leflunomide). Hoechst Marion-Roussel Inc, Kansas City, MO.
24 Product Information. Prolia (denosumab). Amgen USA, Thousand Oaks, CA.
25 Product Information. Zulresso (brexanolone). Sage Therapeutics, Inc., Cambridge, MA.
26 Product Information. Vumerity (diroximel fumarate). Alkermes, Inc, Cambridge, MA.
27 Cerner Multum, Inc. "Australian Product Information.".
28 Product Information. Gilenya (fingolimod). Novartis Pharmaceuticals, East Hanover, NJ.
29 Product Information. Ocrevus (ocrelizumab). Genentech, South San Francisco, CA.
30 Product Information. Zeposia (ozanimod). Celgene Corporation, Summit, NJ.
31 Product Information. Synribo (omacetaxine). Teva Pharmaceuticals USA, North Wales, PA.
32 Filibeck DJ, Grimm D, Forman WB, Leidner BA "Metoclopramide-induced hypertensive crisis." Clin Pharm 3 (1984): 548-9. [PMID: 6541544]
33 Product Information. Belviq (lorcaserin). Eisai Inc, Teaneck, NJ.
34 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]
35 Product Information. Arcalyst (rilonacept). Regeneron Pharmaceuticals Inc, Tarrytown, NY.
36 Product Information. Cimzia (certolizumab). UCB Pharma Inc, Smyrna, GA.
37 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]