procarbazine Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
2272 671-16-9

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • procarbazine
  • ibenzmethyzine
  • procarbazine hydrochloride
  • procarbazine HCl
An antineoplastic agent used primarily in combination with mechlorethamine, vincristine, and prednisone (the MOPP protocol) in the treatment of Hodgkin's disease.
  • Molecular weight: 221.30
  • Formula: C12H19N3O
  • CLOGP: -0.08
  • LIPINSKI: 0
  • HAC: 4
  • HDO: 3
  • TPSA: 53.16
  • ALOGS: -2.99
  • ROTB: 5

  • Status: OFP

  • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

None

ADMET properties:

PropertyValueReference
MRTD (Maximum Recommended Therapeutic Daily Dose) 27.11 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD

Approvals:

DateAgencyCompanyOrphan
July 22, 1969 FDA SIGMA TAU

FDA Adverse Event Reporting System (Female)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Nausea 145.39 29.61 190 2614 687264 45995994
Blood count abnormal 102.44 29.61 39 2765 17839 46665419
Fatigue 67.93 29.61 126 2678 608571 46074687
Maternal exposure before pregnancy 66.50 29.61 20 2784 4461 46678797
Disease progression 64.14 29.61 49 2755 91251 46592007
Neutropenia 57.92 29.61 56 2748 143148 46540110
Hepatocellular injury 51.16 29.61 28 2776 29494 46653764
Platelet count decreased 47.89 29.61 43 2761 99981 46583277
Psychiatric decompensation 45.13 29.61 11 2793 1112 46682146
Persecutory delusion 40.49 29.61 12 2792 2543 46680715
Meningoencephalitis herpetic 40.48 29.61 10 2794 1068 46682190
Necrotising gastritis 40.38 29.61 6 2798 38 46683220
Febrile neutropenia 40.07 29.61 38 2766 94589 46588669
Rectal adenoma 37.77 29.61 6 2798 62 46683196
Malignant neoplasm progression 37.30 29.61 31 2773 64895 46618363
Aplasia 36.52 29.61 12 2792 3564 46679694
White blood cell count decreased 36.39 29.61 39 2765 112192 46571066
Second primary malignancy 36.36 29.61 14 2790 6570 46676688
Central nervous system lymphoma 34.14 29.61 9 2795 1245 46682013
Thrombocytopenia 32.55 29.61 39 2765 126542 46556716
Hepatitis B reactivation 32.46 29.61 9 2795 1505 46681753
Constipation 31.35 29.61 45 2759 174052 46509206
Myelodysplastic syndrome 30.27 29.61 16 2788 15695 46667563

FDA Adverse Event Reporting System (Male)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Acute myeloid leukaemia 211.63 31.27 81 3696 17925 29930776
Nausea 169.28 31.27 196 3581 296761 29651940
Second primary malignancy 157.79 31.27 50 3727 6306 29942395
Myelodysplastic syndrome 123.90 31.27 56 3721 18722 29929979
Malignant transformation 121.52 31.27 26 3751 687 29948014
Fatigue 90.04 31.27 151 3626 320522 29628179
Blood count abnormal 87.25 31.27 38 3739 11614 29937087
Blood stem cell transplant failure 86.80 31.27 18 3759 407 29948294
Azoospermia 81.12 31.27 17 3760 405 29948296
Neutropenia 77.78 31.27 88 3689 128452 29820249
Hepatocellular injury 59.26 31.27 38 3739 25433 29923268
Testicular disorder 58.73 31.27 14 3763 606 29948095
Myositis 50.13 31.27 25 3752 10352 29938349
Angiodysplasia 46.44 31.27 11 3766 463 29948238
Transformation to acute myeloid leukaemia 43.06 31.27 11 3766 635 29948066
Malignant neoplasm progression 41.06 31.27 48 3729 72239 29876462
Premature ageing 37.91 31.27 7 3770 84 29948617
Heart disease congenital 35.80 31.27 11 3766 1247 29947454
Osteonecrosis 34.87 31.27 23 3754 16112 29932589
Bone marrow failure 34.12 31.27 29 3748 29756 29918945

Pharmacologic Action:

SourceCodeDescription
ATC L01XB01 ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
ANTINEOPLASTIC AGENTS
OTHER ANTINEOPLASTIC AGENTS
Methylhydrazines
FDA MoA N0000000236 Alkylating Activity
FDA EPC N0000175558 Alkylating Drug
MeSH PA D000970 Antineoplastic Agents
CHEBI has role CHEBI:35610 cytostatic

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Hodgkin's disease indication 118599009
Astrocytoma, anaplastic off-label use 55353007 DOID:3078
Diffuse non-Hodgkin's lymphoma, large cell off-label use 109969005
Polycythemia vera off-label use 109992005
Mycosis fungoides off-label use 118618005
Glioblastoma multiforme of brain off-label use 276828006 DOID:3073
Malignant neoplasm of brain off-label use 428061005 DOID:1319
Mycosis contraindication 3218000 DOID:1564
Alcoholism contraindication 7200002
Viral disease contraindication 34014006 DOID:934
Acute nephropathy contraindication 58574008
Hepatic failure contraindication 59927004
Blood coagulation disorder contraindication 64779008 DOID:1247
Leukopenia contraindication 84828003 DOID:615
Bacterial infectious disease contraindication 87628006
Kidney disease contraindication 90708001 DOID:557
Disease of liver contraindication 235856003 DOID:409
Anemia contraindication 271737000 DOID:2355
Pregnancy, function contraindication 289908002
Thrombocytopenic disorder contraindication 302215000 DOID:1588
Peripheral nerve disease contraindication 302226006
Bone marrow depression contraindication 307762000
Breastfeeding (mother) contraindication 413712001
Smokes tobacco daily contraindication 449868002
Protozoal Infection contraindication

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 12.29 acidic
pKa2 7.0 Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
DNA DNA OTHER CHEMBL CHEMBL

External reference:

IDSource
4019906 VUID
N0000147991 NUI
D00478 KEGG_DRUG
366-70-1 SECONDARY_CAS_RN
4017789 VANDF
4019906 VANDF
C0033223 UMLSCUI
CHEBI:71417 CHEBI
CHEMBL1321 ChEMBL_ID
CHEMBL1200410 ChEMBL_ID
D011344 MESH_DESCRIPTOR_UI
DB01168 DRUGBANK_ID
7278 IUPHAR_LIGAND_ID
2147 INN_ID
35S93Y190K UNII
4915 PUBCHEM_CID
66925 RXNORM
5360 MMSL
d00354 MMSL
002672 NDDF
004827 NDDF
10174003 SNOMEDCT_US
387474003 SNOMEDCT_US
81583003 SNOMEDCT_US

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Matulane HUMAN PRESCRIPTION DRUG LABEL 1 54482-054 CAPSULE 50 mg ORAL NDA 23 sections