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Identification
NameProcarbazine
Accession NumberDB01168  (APRD00695)
TypeSmall Molecule
GroupsApproved
DescriptionAn antineoplastic agent used primarily in combination with mechlorethamine, vincristine, and prednisone (the MOPP protocol) in the treatment of Hodgkin's disease.
Structure
Thumb
Synonyms
1-Methyl-2-(p-(isopropylcarbamoyl)benzyl)hydrazine
2-(p-Isopropylcarbamoylbenzyl)-1-methylhydrazine
4-((2-Methylhydrazino)methyl)-N-isopropylbenzamide
N-(1-Methylethyl)-4-((2-methylhydrazino)methyl)benzamide
N-4-Isopropylcarbamoylbenzyl-N'-methylhydrazine
N-isopropyl-4-[(2-methylhydrazino)methyl]benzamide
N-Isopropyl-p-(2-methylhydrazinomethyl)-benzamide
N-Isopropyl-α-(2-methylhydrazino)-p-toluamide
p-(2-Methylhydrazinomethyl)-N-isopropylbenzamide
Procarbazin
Procarbazina
Procarbazinum
External Identifiers Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
MatulaneCapsule50 mg/1OralSigma Tau Pharmaceuticals, Inc.1985-12-27Not applicableUs
MatulaneCapsule50 mgOralSigma Tau Pharmaceuticals Inc1970-12-31Not applicableCanada
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
IndicarbNot Available
NatulanNot Available
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Procarbazine hydrochloride
Thumb
  • InChI Key: OCSSHHHAHMCFDV-UHFFFAOYSA-N
  • Monoisotopic Mass: 293.106167723
  • Average Mass: 294.221
DBSALT000731
Categories
UNII35S93Y190K
CAS number671-16-9
WeightAverage: 221.2988
Monoisotopic: 221.152812245
Chemical FormulaC12H19N3O
InChI KeyCPTBDICYNRMXFX-UHFFFAOYSA-N
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)
IUPAC Name
4-[(2-methylhydrazin-1-yl)methyl]-N-(propan-2-yl)benzamide
SMILES
CNNCC1=CC=C(C=C1)C(=O)NC(C)C
Pharmacology
IndicationFor use with other anticancer drugs for the treatment of stage III and stage IV Hodgkin's disease.
Structured Indications
PharmacodynamicsProcarbazine is an antineoplastic in the class of alkylating agents and is used to treat various forms of cancer. Alkylating agents are so named because of their ability to add alkyl groups to many electronegative groups under conditions present in cells. They stop tumor growth by cross-linking guanine bases in DNA double-helix strands - directly attacking DNA. This makes the strands unable to uncoil and separate. As this is necessary in DNA replication, the cells can no longer divide. In addition, these drugs add methyl or other alkyl groups onto molecules where they do not belong which in turn inhibits their correct utilization by base pairing and causes a miscoding of DNA. Procarbazine is cell-phase specific for the S phase of cell division.
Mechanism of actionThe 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.
TargetKindPharmacological actionActionsOrganismUniProt ID
DNANucleotideyes
cross-linking/alkylation
Humannot applicabledetails
Monoamine oxidaseProtein groupyes
inhibitor
Humannot applicabledetails
Related Articles
AbsorptionProcarbazine is rapidly and completely absorbed.
Volume of distributionNot Available
Protein bindingNot Available
Metabolism

Procarbazine is metabolized primarily in the liver and kidneys. The drug appears to be auto-oxidized to the azo derivative with the release of hydrogen peroxide. The azo derivative isomerizes to the hydrazone, and following hydrolysis splits into a benzylaldehyde derivative and methylhydrazine. The methylhydrazine is further degraded to CO2 and CH4 and possibly hydrazine, whereas the aldehyde is oxidized to N-isopropylterephthalamic acid, which is excreted in the urine.

SubstrateEnzymesProduct
Procarbazine
Not Available
HydrazineDetails
Procarbazine
Not Available
N-isopropylterephthalamic acidDetails
Route of eliminationNot Available
Half life10 minutes
ClearanceNot Available
ToxicityLD50=785 mg/kg (orally in rats)
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
Interactions
Drug Interactions
DrugInteractionDrug group
AcepromazineThe risk or severity of adverse effects can be increased when Procarbazine is combined with Acepromazine.Approved, Vet Approved
AceprometazineThe risk or severity of adverse effects can be increased when Procarbazine is combined with Aceprometazine.Approved
AcetophenazineThe risk or severity of adverse effects can be increased when Procarbazine is combined with Acetophenazine.Approved
AcetyldigitoxinAcetyldigitoxin may decrease the cardiotoxic activities of Procarbazine.Approved
AlmotriptanThe risk or severity of adverse effects can be increased when Almotriptan is combined with Procarbazine.Approved, Investigational
ALT-110The risk or severity of adverse effects can be increased when Procarbazine is combined with ALT-110.Investigational
AmisulprideThe risk or severity of adverse effects can be increased when Procarbazine is combined with Amisulpride.Approved, Investigational
AmitriptylineThe risk or severity of adverse effects can be increased when Amitriptyline is combined with Procarbazine.Approved
AmoxapineThe risk or severity of adverse effects can be increased when Amoxapine is combined with Procarbazine.Approved
AmperozideThe risk or severity of adverse effects can be increased when Procarbazine is combined with Amperozide.Experimental
AnvirzelAnvirzel may decrease the cardiotoxic activities of Procarbazine.Investigational
AripiprazoleThe risk or severity of adverse effects can be increased when Procarbazine is combined with Aripiprazole.Approved, Investigational
AsenapineThe risk or severity of adverse effects can be increased when Procarbazine is combined with Asenapine.Approved
AzaperoneThe risk or severity of adverse effects can be increased when Procarbazine is combined with Azaperone.Vet Approved
BcgThe therapeutic efficacy of Bcg can be decreased when used in combination with Procarbazine.Investigational
BenperidolThe risk or severity of adverse effects can be increased when Procarbazine is combined with Benperidol.Investigational
BevacizumabBevacizumab may increase the cardiotoxic activities of Procarbazine.Approved, Investigational
BifeprunoxThe risk or severity of adverse effects can be increased when Procarbazine is combined with Bifeprunox.Investigational
BrexpiprazoleThe risk or severity of adverse effects can be increased when Procarbazine is combined with Brexpiprazole.Approved
BromocriptineThe risk or severity of adverse effects can be increased when Procarbazine is combined with Bromocriptine.Approved, Investigational
BromperidolThe risk or severity of adverse effects can be increased when Procarbazine is combined with Bromperidol.Investigational
BuspironeThe risk or severity of adverse effects can be increased when Buspirone is combined with Procarbazine.Approved, Investigational
CabazitaxelThe risk or severity of adverse effects can be increased when Cabazitaxel is combined with Procarbazine.Approved
CabergolineThe risk or severity of adverse effects can be increased when Cabergoline is combined with Procarbazine.Approved
CarbocisteineThe risk or severity of adverse effects can be increased when Procarbazine is combined with Carbocisteine.Approved
CariprazineThe risk or severity of adverse effects can be increased when Procarbazine is combined with Cariprazine.Approved
CDX-110The risk or severity of adverse effects can be increased when Procarbazine is combined with CDX-110.Investigational
ChlorpromazineThe risk or severity of adverse effects can be increased when Procarbazine is combined with Chlorpromazine.Approved, Vet Approved
ChlorprothixeneThe risk or severity of adverse effects can be increased when Procarbazine is combined with Chlorprothixene.Approved, Withdrawn
CitalopramThe risk or severity of adverse effects can be increased when Citalopram is combined with Procarbazine.Approved
ClomipramineThe risk or severity of adverse effects can be increased when Procarbazine is combined with Clomipramine.Approved, Vet Approved
ClozapineThe risk or severity of adverse effects can be increased when Procarbazine is combined with Clozapine.Approved
CyamemazineThe risk or severity of adverse effects can be increased when Procarbazine is combined with Cyamemazine.Approved
CyclobenzaprineThe risk or severity of adverse effects can be increased when Cyclobenzaprine is combined with Procarbazine.Approved
CyclophosphamideCyclophosphamide may increase the cardiotoxic activities of Procarbazine.Approved, Investigational
DapiprazoleThe risk or severity of adverse effects can be increased when Procarbazine is combined with Dapiprazole.Approved
DapoxetineThe risk or severity of adverse effects can be increased when Dapoxetine is combined with Procarbazine.Investigational
DenosumabThe risk or severity of adverse effects can be increased when Denosumab is combined with Procarbazine.Approved
DesipramineThe risk or severity of adverse effects can be increased when Desipramine is combined with Procarbazine.Approved
DeslanosideDeslanoside may decrease the cardiotoxic activities of Procarbazine.Approved
DesvenlafaxineThe risk or severity of adverse effects can be increased when Procarbazine is combined with Desvenlafaxine.Approved
DextromethorphanThe risk or severity of adverse effects can be increased when Dextromethorphan is combined with Procarbazine.Approved
DigitoxinDigitoxin may decrease the cardiotoxic activities of Procarbazine.Approved
DigoxinDigoxin may decrease the cardiotoxic activities of Procarbazine.Approved
DihydroergotamineThe risk or severity of adverse effects can be increased when Dihydroergotamine is combined with Procarbazine.Approved
DocetaxelThe risk or severity of adverse effects can be increased when Docetaxel is combined with Procarbazine.Approved, Investigational
DolasetronDolasetron may increase the serotonergic activities of Procarbazine.Approved
DoxepinThe risk or severity of adverse effects can be increased when Doxepin is combined with Procarbazine.Approved
DroperidolThe risk or severity of adverse effects can be increased when Procarbazine is combined with Droperidol.Approved, Vet Approved
DuloxetineThe risk or severity of adverse effects can be increased when Duloxetine is combined with Procarbazine.Approved
EcopipamThe risk or severity of adverse effects can be increased when Procarbazine is combined with Ecopipam.Investigational
EletriptanThe risk or severity of adverse effects can be increased when Eletriptan is combined with Procarbazine.Approved, Investigational
Ergoloid mesylateThe risk or severity of adverse effects can be increased when Ergoloid mesylate is combined with Procarbazine.Approved
ErgonovineThe risk or severity of adverse effects can be increased when Procarbazine is combined with Ergonovine.Approved
ErgotamineThe risk or severity of adverse effects can be increased when Ergotamine is combined with Procarbazine.Approved
EscitalopramThe risk or severity of adverse effects can be increased when Procarbazine is combined with Escitalopram.Approved, Investigational
FencamfamineThe risk or severity of adverse effects can be increased when Procarbazine is combined with Fencamfamine.Approved, Illicit, Withdrawn
FentanylThe risk or severity of adverse effects can be increased when Fentanyl is combined with Procarbazine.Approved, Illicit, Investigational, Vet Approved
FingolimodProcarbazine may increase the immunosuppressive activities of Fingolimod.Approved, Investigational
FluoxetineThe risk or severity of adverse effects can be increased when Fluoxetine is combined with Procarbazine.Approved, Vet Approved
FlupentixolThe risk or severity of adverse effects can be increased when Procarbazine is combined with Flupentixol.Approved, Withdrawn
FluphenazineThe risk or severity of adverse effects can be increased when Procarbazine is combined with Fluphenazine.Approved
FluspirileneThe risk or severity of adverse effects can be increased when Procarbazine is combined with Fluspirilene.Approved
FluvoxamineThe risk or severity of adverse effects can be increased when Fluvoxamine is combined with Procarbazine.Approved, Investigational
FrovatriptanThe risk or severity of adverse effects can be increased when Frovatriptan is combined with Procarbazine.Approved, Investigational
G17DTThe risk or severity of adverse effects can be increased when Procarbazine is combined with G17DT.Investigational
GI-5005The risk or severity of adverse effects can be increased when Procarbazine is combined with GI-5005.Investigational
GranisetronGranisetron may increase the serotonergic activities of Procarbazine.Approved, Investigational
HaloperidolThe risk or severity of adverse effects can be increased when Procarbazine is combined with Haloperidol.Approved
IloperidoneThe risk or severity of adverse effects can be increased when Procarbazine is combined with Iloperidone.Approved
ImipramineThe risk or severity of adverse effects can be increased when Imipramine is combined with Procarbazine.Approved
INGN 201The risk or severity of adverse effects can be increased when Procarbazine is combined with INGN 201.Investigational
INGN 225The risk or severity of adverse effects can be increased when Procarbazine is combined with INGN 225.Investigational
IsocarboxazidThe risk or severity of adverse effects can be increased when Procarbazine is combined with Isocarboxazid.Approved
LeflunomideThe risk or severity of adverse effects can be increased when Procarbazine is combined with Leflunomide.Approved, Investigational
LevomilnacipranThe risk or severity of adverse effects can be increased when Procarbazine is combined with Levomilnacipran.Approved
LinezolidThe risk or severity of adverse effects can be increased when Linezolid is combined with Procarbazine.Approved, Investigational
LithiumThe risk or severity of adverse effects can be increased when Procarbazine is combined with Lithium.Approved
LorcaserinThe risk or severity of adverse effects can be increased when Procarbazine is combined with Lorcaserin.Approved
LoxapineThe risk or severity of adverse effects can be increased when Procarbazine is combined with Loxapine.Approved
LurasidoneThe risk or severity of adverse effects can be increased when Procarbazine is combined with Lurasidone.Approved
MaprotilineThe risk or severity of adverse effects can be increased when Maprotiline is combined with Procarbazine.Approved
MelperoneThe risk or severity of adverse effects can be increased when Procarbazine is combined with Melperone.Approved
MesoridazineThe risk or severity of adverse effects can be increased when Procarbazine is combined with Mesoridazine.Approved
MetamizoleThe risk or severity of adverse effects can be increased when Metamizole is combined with Procarbazine.Withdrawn
MethadoneThe risk or severity of adverse effects can be increased when Methadone is combined with Procarbazine.Approved
MethotrimeprazineThe risk or severity of adverse effects can be increased when Procarbazine is combined with Methotrimeprazine.Approved
MetoclopramideThe risk or severity of adverse effects can be increased when Procarbazine is combined with Metoclopramide.Approved, Investigational
MilnacipranThe risk or severity of adverse effects can be increased when Procarbazine is combined with Milnacipran.Approved
MirtazapineThe risk or severity of adverse effects can be increased when Mirtazapine is combined with Procarbazine.Approved
MoclobemideThe risk or severity of adverse effects can be increased when Procarbazine is combined with Moclobemide.Approved
MolindoneThe risk or severity of adverse effects can be increased when Procarbazine is combined with Molindone.Approved
NaratriptanThe risk or severity of adverse effects can be increased when Naratriptan is combined with Procarbazine.Approved, Investigational
NatalizumabThe risk or severity of adverse effects can be increased when Procarbazine is combined with Natalizumab.Approved, Investigational
NefazodoneThe risk or severity of adverse effects can be increased when Nefazodone is combined with Procarbazine.Approved, Withdrawn
NortriptylineThe risk or severity of adverse effects can be increased when Nortriptyline is combined with Procarbazine.Approved
OlanzapineThe risk or severity of adverse effects can be increased when Procarbazine is combined with Olanzapine.Approved, Investigational
OndansetronOndansetron may increase the serotonergic activities of Procarbazine.Approved
OsanetantThe risk or severity of adverse effects can be increased when Procarbazine is combined with Osanetant.Investigational
OuabainOuabain may decrease the cardiotoxic activities of Procarbazine.Approved
PaclitaxelThe risk or severity of adverse effects can be increased when Paclitaxel is combined with Procarbazine.Approved, Vet Approved
PaliperidoneThe risk or severity of adverse effects can be increased when Procarbazine is combined with Paliperidone.Approved
PalonosetronPalonosetron may increase the serotonergic activities of Procarbazine.Approved, Investigational
ParoxetineThe risk or severity of adverse effects can be increased when Paroxetine is combined with Procarbazine.Approved, Investigational
PerazineThe risk or severity of adverse effects can be increased when Procarbazine is combined with Perazine.Investigational
PerospironeThe risk or severity of adverse effects can be increased when Procarbazine is combined with Perospirone.Approved
PerphenazineThe risk or severity of adverse effects can be increased when Procarbazine is combined with Perphenazine.Approved
PethidineThe risk or severity of adverse effects can be increased when Pethidine is combined with Procarbazine.Approved
PhenelzineThe risk or severity of adverse effects can be increased when Phenelzine is combined with Procarbazine.Approved
PimecrolimusThe risk or severity of adverse effects can be increased when Pimecrolimus is combined with Procarbazine.Approved, Investigational
PimozideThe risk or severity of adverse effects can be increased when Procarbazine is combined with Pimozide.Approved
PipamperoneThe risk or severity of adverse effects can be increased when Procarbazine is combined with Pipamperone.Approved
PipotiazineThe risk or severity of adverse effects can be increased when Procarbazine is combined with Pipotiazine.Approved
ProchlorperazineThe risk or severity of adverse effects can be increased when Procarbazine is combined with Prochlorperazine.Approved, Vet Approved
PromazineThe risk or severity of adverse effects can be increased when Procarbazine is combined with Promazine.Approved, Vet Approved
PromethazineThe risk or severity of adverse effects can be increased when Promethazine is combined with Procarbazine.Approved
PropericiazineThe risk or severity of adverse effects can be increased when Procarbazine is combined with Propericiazine.Approved
ProthipendylThe risk or severity of adverse effects can be increased when Procarbazine is combined with Prothipendyl.Investigational
ProtriptylineThe risk or severity of adverse effects can be increased when Protriptyline is combined with Procarbazine.Approved
QuetiapineThe risk or severity of adverse effects can be increased when Procarbazine is combined with Quetiapine.Approved
Rabies vaccineThe risk or severity of adverse effects can be increased when Procarbazine is combined with Rabies vaccine.Approved
Rabies vaccineThe therapeutic efficacy of Rabies vaccine can be decreased when used in combination with Procarbazine.Approved
RacloprideThe risk or severity of adverse effects can be increased when Procarbazine is combined with Raclopride.Investigational
RasagilineThe risk or severity of adverse effects can be increased when Procarbazine is combined with Rasagiline.Approved
RemoxiprideThe risk or severity of adverse effects can be increased when Procarbazine is combined with Remoxipride.Approved, Withdrawn
ReserpineThe risk or severity of adverse effects can be increased when Procarbazine is combined with Reserpine.Approved
RisperidoneThe risk or severity of adverse effects can be increased when Procarbazine is combined with Risperidone.Approved, Investigational
RitanserinThe risk or severity of adverse effects can be increased when Procarbazine is combined with Ritanserin.Investigational
RizatriptanThe risk or severity of adverse effects can be increased when Rizatriptan is combined with Procarbazine.Approved
RoflumilastRoflumilast may increase the immunosuppressive activities of Procarbazine.Approved
SelegilineThe risk or severity of adverse effects can be increased when Selegiline is combined with Procarbazine.Approved, Investigational, Vet Approved
SertindoleThe risk or severity of adverse effects can be increased when Procarbazine is combined with Sertindole.Approved, Withdrawn
SertralineThe risk or severity of adverse effects can be increased when Sertraline is combined with Procarbazine.Approved
Sipuleucel-TThe therapeutic efficacy of Sipuleucel-T can be decreased when used in combination with Procarbazine.Approved
SRP 299The risk or severity of adverse effects can be increased when Procarbazine is combined with SRP 299.Investigational
SulpirideThe risk or severity of adverse effects can be increased when Procarbazine is combined with Sulpiride.Approved
SumatriptanThe risk or severity of adverse effects can be increased when Sumatriptan is combined with Procarbazine.Approved, Investigational
TacrolimusThe risk or severity of adverse effects can be increased when Tacrolimus is combined with Procarbazine.Approved, Investigational
TapentadolThe risk or severity of adverse effects can be increased when Procarbazine is combined with Tapentadol.Approved
Tedizolid PhosphateTedizolid Phosphate may increase the serotonergic activities of Procarbazine.Approved
TG4010The risk or severity of adverse effects can be increased when Procarbazine is combined with TG4010.Investigational
ThioproperazineThe risk or severity of adverse effects can be increased when Procarbazine is combined with Thioproperazine.Approved
ThioridazineThe risk or severity of adverse effects can be increased when Procarbazine is combined with Thioridazine.Approved
ThiothixeneThe risk or severity of adverse effects can be increased when Procarbazine is combined with Thiothixene.Approved
TiaprideThe risk or severity of adverse effects can be increased when Procarbazine is combined with Tiapride.Investigational
TofacitinibProcarbazine may increase the immunosuppressive activities of Tofacitinib.Approved, Investigational
TramadolThe risk or severity of adverse effects can be increased when Tramadol is combined with Procarbazine.Approved, Investigational
TranylcypromineThe risk or severity of adverse effects can be increased when Tranylcypromine is combined with Procarbazine.Approved
TrastuzumabTrastuzumab may increase the cardiotoxic activities of Procarbazine.Approved, Investigational
TrazodoneThe risk or severity of adverse effects can be increased when Trazodone is combined with Procarbazine.Approved, Investigational
TrifluoperazineThe risk or severity of adverse effects can be increased when Procarbazine is combined with Trifluoperazine.Approved
TriflupromazineThe risk or severity of adverse effects can be increased when Procarbazine is combined with Triflupromazine.Approved, Vet Approved
TrimipramineThe risk or severity of adverse effects can be increased when Trimipramine is combined with Procarbazine.Approved
TropisetronTropisetron may increase the serotonergic activities of Procarbazine.Investigational
VenlafaxineThe risk or severity of adverse effects can be increased when Venlafaxine is combined with Procarbazine.Approved
VilazodoneThe risk or severity of adverse effects can be increased when Procarbazine is combined with Vilazodone.Approved
VortioxetineThe risk or severity of adverse effects can be increased when Procarbazine is combined with Vortioxetine.Approved
ZiprasidoneThe risk or severity of adverse effects can be increased when Procarbazine is combined with Ziprasidone.Approved
ZolmitriptanThe risk or severity of adverse effects can be increased when Zolmitriptan is combined with Procarbazine.Approved, Investigational
ZotepineThe risk or severity of adverse effects can be increased when Procarbazine is combined with Zotepine.Approved
ZuclopenthixolThe risk or severity of adverse effects can be increased when Procarbazine is combined with Zuclopenthixol.Approved, Investigational
Food InteractionsNot Available
References
Synthesis Reference

DrugSyn.org

US3520926
General ReferencesNot Available
External Links
ATC CodesL01XB01
AHFS Codes
  • 10:00.00
PDB EntriesNot Available
FDA labelNot Available
MSDSDownload (63.2 KB)
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9954
Blood Brain Barrier+0.9855
Caco-2 permeable+0.6013
P-glycoprotein substrateNon-substrate0.5748
P-glycoprotein inhibitor INon-inhibitor0.8839
P-glycoprotein inhibitor IINon-inhibitor0.9771
Renal organic cation transporterNon-inhibitor0.7974
CYP450 2C9 substrateNon-substrate0.8293
CYP450 2D6 substrateNon-substrate0.702
CYP450 3A4 substrateNon-substrate0.5484
CYP450 1A2 substrateInhibitor0.9107
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorInhibitor0.8994
CYP450 3A4 inhibitorNon-inhibitor0.8308
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9414
Ames testNon AMES toxic0.9132
CarcinogenicityCarcinogens 0.6428
BiodegradationNot ready biodegradable0.9741
Rat acute toxicity2.4348 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9785
hERG inhibition (predictor II)Non-inhibitor0.9287
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage forms
FormRouteStrength
CapsuleOral50 mg/1
CapsuleOral50 mg
Prices
Unit descriptionCostUnit
Matulane 50 mg capsule55.68USD capsule
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point223 °CNot Available
water solubility1420 mg/LNot Available
logP0.06HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility0.228 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 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity86.98 m3·mol-1ChemAxon
Polarizability25.88 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
MSMass Spectrum (Electron Ionization)splash10-016u-6900000000-6488b097a4640e8af61aView in MoNA
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 ClassBenzamides
Direct ParentBenzamides
Alternative Parents
Substituents
  • Benzoic acid or derivatives
  • Benzamide
  • Phenylmethylamine
  • Benzylamine
  • Benzoyl
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Hydrazine derivative
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors

Targets

1. DNA
Kind
Nucleotide
Organism
Human
Pharmacological action
yes
Actions
cross-linking/alkylation
General Function:
Used for biological information storage.
Specific Function:
DNA contains the instructions needed for an organism to develop, survive and reproduce.
Molecular Weight:
2.15 x 1012 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Ogawa K, Hiraku Y, Oikawa S, Murata M, Sugimura Y, Kawamura J, Kawanishi S: Molecular mechanisms of DNA damage induced by procarbazine in the presence of Cu(II). Mutat Res. 2003 Aug 5;539(1-2):145-55. [PubMed:12948823 ]
  4. Kyrtopoulos SA, Anderson LM, Chhabra SK, Souliotis VL, Pletsa V, Valavanis C, Georgiadis P: DNA adducts and the mechanism of carcinogenesis and cytotoxicity of methylating agents of environmental and clinical significance. Cancer Detect Prev. 1997;21(5):391-405. [PubMed:9307842 ]
Kind
Protein group
Organism
Human
Pharmacological action
yes
Actions
inhibitor
General Function:
Serotonin binding
Specific Function:
Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues. MAOA preferentially oxidizes biogenic amines such as 5-hydroxytryptamine (5-HT), norepinephrine and epinephrine.
Components:
NameUniProt IDDetails
Amine oxidase [flavin-containing] AP21397 Details
Amine oxidase [flavin-containing] BP27338 Details
References
  1. Holt A, Sharman DF, Callingham BA, Kettler R: Characteristics of procarbazine as an inhibitor in-vitro of rat semicarbazide-sensitive amine oxidase. J Pharm Pharmacol. 1992 Jun;44(6):487-93. [PubMed:1359073 ]
  2. Kraft SL, Baker NM, Carpenter J, Bostwick JR: Procarbazine and antidepressants: a retrospective review of the risk of serotonin toxicity. Psychooncology. 2014 Jan;23(1):108-13. doi: 10.1002/pon.3378. Epub 2013 Aug 29. [PubMed:24038727 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Xanthine oxidase 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 Da
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Oxygen binding
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, retinoid and xenobiotics. Preferentially oxidizes 17beta-estradiol to the carcinogenic 4-hydroxy derivative, and a variety of procarcinogenic compou...
Gene Name:
CYP1B1
Uniprot ID:
Q16678
Molecular Weight:
60845.33 Da
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 ]
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Drug created on June 13, 2005 07:24 / Updated on October 27, 2016 09:48