Procarbazine

Common Name

Procarbazine Description

Procarbazine is only found in individuals that have used or taken this drug. It is an antineoplastic agent used primarily in combination with mechlorethamine, vincristine, and prednisone (the MOPP protocol) in the treatment of Hodgkins disease. [PubChem]The precise mode of cytotoxic action of procarbazine has not been clearly defined. There is evidence that the drug may act by inhibition of protein, RNA and DNA synthesis. Studies have suggested that procarbazine may inhibit transmethylation of methyl groups of methionine into t-RNA. The absence of functional t-RNA colid cause the cessation of protein synthesis and consequently DNA and RNA synthesis. In addition, procarbazine may directly damage DNA. Hydrogen peroxide, formed during the auto-oxidation of the drug, may attack protein slifhydryl groups contained in residual protein which is tightly bound to DNA. Structure

Synonyms

Value Source 1-Methyl-2-(P-(isopropylcarbamoyl)benzyl)hydrazineChEBI 2-(P-Isopropylcarbamoylbenzyl)-1-methylhydrazineChEBI 4-((2-methylhydrazino)Methyl)-N-isopropylbenzamideChEBI N-(1-Methylethyl)-4-((2-methylhydrazino)methyl)benzamideChEBI N-4-Isopropylcarbamoylbenzyl-n'-methylhydrazineChEBI N-Isopropyl-4-[(2-methylhydrazino)methyl]benzamideChEBI N-Isopropyl-alpha-(2-methylhydrazino)-P-toluamideChEBI N-Isopropyl-P-(2-methylhydrazinomethyl)-benzamideChEBI P-(2-Methylhydrazinomethyl)-N-isopropylbenzamideChEBI ProcarbazinChEBI ProcarbazinaChEBI ProcarbazinumChEBI N-Isopropyl-a-(2-methylhydrazino)-P-toluamideGenerator N-Isopropyl-α-(2-methylhydrazino)-P-toluamideGenerator IbenzmethyzinHMDB IbenzmethyzineHMDB IBZHMDB MBHHMDB MIHHMDB PCXHMDB Cambridge laboratories brand OF procarbazine hydrochlorideMeSH Procarbazine monohydrobromideMeSH Procarbazine monohydrochlorideMeSH Monohydrochloride, procarbazineMeSH MatlianeMeSH Monohydrobromide, procarbazineMeSH NatlianMeSH Roche brand OF procarbazine hydrochlorideMeSH Hydrochloride, procarbazineMeSH Procarbazine hydrochlorideMeSH Sigma tau brand OF procarbazine hydrochlorideMeSH Sigma-tau brand OF procarbazineMeSH Sigma-tau brand OF procarbazine hydrochlorideMeSH

Chemical Formlia

C₁₂H₁₉N₃O Average Molecliar Weight

221.2988 Monoisotopic Molecliar Weight

221.152812245 IUPAC Name

4-[(2-methylhydrazin-1-yl)methyl]-N-(propan-2-yl)benzamide Traditional Name

procarbazine CAS Registry Number

671-16-9 SMILES

InChI Identifier

InChI Key

CPTBDICYNRMXFX-UHFFFAOYSA-N Chemical Taxonomy Description

This compound belongs to the class of organic compounds known as benzamides. These are organic compounds containing a carboxamido substituent attached to a benzene ring. Kingdom

Organic compounds Super Class

Benzenoids Class

Benzene and substituted derivatives Sub Class

Benzoic acids and derivatives Direct Parent

Benzamides Alternative Parents

Benzoyl derivatives

Secondary carboxylic acid amides

Alkylhydrazines

Organopnictogen compounds

Organooxygen compounds

Organic oxides

Hydrocarbon derivatives

Substituents

Benzamide

Benzoyl

Secondary carboxylic acid amide

Carboxamide group

Alkylhydrazine

Carboxylic acid derivative

Organic nitrogen compound

Organic oxygen compound

Organopnictogen compound

Organic oxide

Hydrocarbon derivative

Organooxygen compound

Organonitrogen compound

Hydrazine derivative

Aromatic homomonocyclic compound

Molecliar Framework

Aromatic homomonocyclic compounds External Descriptors

benzamides (CHEBI:71417 )

hydrazines (CHEBI:71417 )

Ontology Status

Expected but not Quantified Origin

Drug

Biofunction

Antineoplastic Agents

Application

Pharmaceutical

Cellliar locations

Cytoplasm

Membrane

Physical Properties State

Solid Experimental Properties

Property Value Reference Melting Point223 °CNot Available Boiling PointNot AvailableNot Available Water Solubility2.28e-01 g/LNot Available LogP2.6Not Available

Predicted Properties

Property Value Source Water Solubility0.23 mg/mLALOGPS logP0.53ALOGPS logP0.99ChemAxon logS-3ALOGPS pKa (Strongest Acidic)15.03ChemAxon pKa (Strongest Basic)5.6ChemAxon Physiological Charge0ChemAxon Hydrogen Acceptor Count3ChemAxon Hydrogen Donor Count3ChemAxon Polar Surface Area53.16 ŲChemAxon Rotatable Bond Count5ChemAxon Refractivity86.98 m³·mol^-1ChemAxon Polarizability25.88 ųChemAxon Number of Rings1ChemAxon Bioavailability1ChemAxon Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon

Spectra Spectra

Spectrum Type Description Splash Key LC-MS/MS

LC-MS/MS Spectrum – , positivesplash10-0096-0910000000-161c214dc9eb9c75895bView in MoNA Predicted LC-MS/MS

Predicted LC-MS/MS Spectrum – 10V, PositiveNot Available Predicted LC-MS/MS

Predicted LC-MS/MS Spectrum – 20V, PositiveNot Available Predicted LC-MS/MS

Predicted LC-MS/MS Spectrum – 40V, PositiveNot Available Predicted LC-MS/MS

Predicted LC-MS/MS Spectrum – 10V, NegativeNot Available Predicted LC-MS/MS

Predicted LC-MS/MS Spectrum – 20V, NegativeNot Available Predicted LC-MS/MS

Predicted LC-MS/MS Spectrum – 40V, NegativeNot Available MS

Mass Spectrum (Electron Ionization)splash10-016u-6900000000-6488b097a4640e8af61aView in MoNA

Biological Properties Cellliar Locations

Cytoplasm

Membrane

Biofluid Locations

Blood

Urine

Tissue Location

Not Available Pathways

Not Available Normal Concentrations

Biofluid Status Value Age Sex Condition Reference Details BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01168

21059682

details UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01168

21059682

details

Abnormal Concentrations

Not Available Predicted Concentrations

Biofluid Value Original age Original sex Original condition Comments Blood0-5 uMAdlit (>18 years old)BothNormalPredicted based on drug qualities Blood0-2 umol/mmol creatinineAdlit (>18 years old)BothNormalPredicted based on drug qualities

Associated Disorders and Diseases Disease References

None Associated OMIM IDs

None External Links DrugBank ID

DB01168 DrugBank Metabolite ID

Not Available Phenol Explorer Compound ID

Not Available Phenol Explorer Metabolite ID

Not Available FoodDB ID

Not Available KNApSAcK ID

Not Available Chemspider ID

4746 KEGG Compound ID

C07402 BioCyc ID

Not Available BiGG ID

Not Available Wikipedia Link

Procarbazine NuGOwiki Link

HMDB15299 Metagene Link

HMDB15299 METLIN ID

Not Available PubChem Compound

4915 PDB ID

Not Available ChEBI ID

366225

Product: AMPPD

References Synthesis Reference Not Available Material Safety Data Sheet (MSDS) Not Available General References Not Available

Enzymes

General function:

Involved in oxidoreductase activity

Specific function:

Key enzyme in purine degradation. Catalyzes the oxidation of hypoxanthine to xanthine. Catalyzes the oxidation of xanthine to uric acid. Contributes to the generation of reactive oxygen species. Has also low oxidase activity towards aldehydes (in vitro).

Gene Name:

XDH

Uniprot ID:

P47989

Molecular weight:

146422.99

General function:

Involved in monooxygenase activity

Specific function:

Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.Participates in the metabolism of an as-yet-unknown biologically active molecule that is a participant in eye development.

Gene Name:

CYP1B1

Uniprot ID:

Q16678

Molecular weight:

60845.33

References

1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

PMID: 11118147

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