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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:51 UTC
Update Date2018-05-20 20:17:02 UTC
HMDB IDHMDB0015299
Secondary Accession Numbers
  • HMDB15299
Metabolite Identification
Common NameProcarbazine
DescriptionProcarbazine 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 Hodgkin's 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 could 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 sulfhydryl groups contained in residual protein which is tightly bound to DNA.
Structure
Thumb
Synonyms
ValueSource
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
MatulaneMeSH
Monohydrobromide, procarbazineMeSH
NatulanMeSH
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 FormulaC12H19N3O
Average Molecular Weight221.2988
Monoisotopic Molecular Weight221.152812245
IUPAC Name4-[(2-methylhydrazin-1-yl)methyl]-N-(propan-2-yl)benzamide
Traditional Nameprocarbazine
CAS Registry Number671-16-9
SMILES
CNNCC1=CC=C(C=C1)C(=O)NC(C)C
InChI Identifier
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)
InChI KeyCPTBDICYNRMXFX-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as benzamides. These are organic compounds containing a carboxamido substituent attached to a benzene ring.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct ParentBenzamides
Alternative Parents
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
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Source:

Biological location:

Role

Indirect biological role:

Environmental role:

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point223 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.23 g/LNot Available
LogP2.6Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.23 g/LALOGPS
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
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-07c6-7920000000-3801345089023dd56325View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0096-0910000000-161c214dc9eb9c75895bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-1960000000-9fa182eac5a77441bb8aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03fr-0900000000-ff9288484ea9ffb99146View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a59-2900000000-bc0369114d1004e57e00View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00dl-5890000000-78c039ed3aeb234794acView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00fs-9540000000-bbeb52cfbb2f51e65f4aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a6s-9300000000-ff5f840e133b25fca3e8View in MoNA
MSMass Spectrum (Electron Ionization)splash10-016u-6900000000-6488b097a4640e8af61aView in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01168 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01168 details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01168
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4746
KEGG Compound IDC07402
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkProcarbazine
METLIN IDNot Available
PubChem Compound4915
PDB IDNot Available
ChEBI ID71417
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot 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 ]