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

Stem definition	Drug id	CAS RN
	2272	671-16-9

Description:

Molecule	Description
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

Molecule

Description

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:

Property	Value	Reference
MRTD (Maximum Recommended Therapeutic Daily Dose)	27.11 µM/kg/day	Contrera JF, Matthews EJ, Kruhlak NL, Benz RD

Approvals:

Date	Agency	Company	Orphan
July 22, 1969	FDA	SIGMA TAU

FDA Adverse Event Reporting System (Female)

MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients 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 term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients 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:

Source	Code	Description
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)

Disease	Relation	SNOMED_ID	DOID
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 level	Dissociation constant	Type (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:

Target	Class	Pharos	UniProt	Action	Type	Activity value (-log[M])	Mechanism action	Bioact source	MoA source
DNA	DNA			OTHER				CHEMBL	CHEMBL

External reference:

ID	Source
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:

Product	Category	Ingredients	NDC	Form	Quantity	Route	Marketing	Label
Matulane	HUMAN PRESCRIPTION DRUG LABEL	1	54482-054	CAPSULE	50 mg	ORAL	NDA	23 sections