Basic information
- CAS
366-70-1- Standard SMILES
CNNCc1ccc(C(=O)NC(C)C)cc1.Cl- InChIKey
DERJYEZSLHIUKF-UHFFFAOYSA-N- Molecular formula
- C12H19N3O.ClH
- Average molar mass
- 257.76 g/mol
- Monoisotopic mass
- 257.12949
Overview
Procarbazine hydrochloride can cause cancer according to an independent committee of scientific and health experts. It can cause developmental toxicity according to state or federal government labeling requirements.
Names & identifiers
- Preferred name
- Procarbazine Hydrochloride
- IUPAC
- 4-[(2-methylhydrazinyl)methyl]-N-propan-2-ylbenzamide;hydrochloride
- English name
- Procarbazine hydrochloride
- Molecular formula
- C12H20ClN3O
- Molecular weight
- 257.76
Names & synonyms
Procarbazine hydrochloride366-70-1PROCARBAZINE HClNathulaneNatunalarMIH hydrochloridePCB hydrochlorideIbenzmethyzine hydrochlorideNatulan hydrochlorideIbenzmethyzin hydrochlorideNSC-77213Ro 4-6467/1
Show more names
ibzmatulaneMutulaneNatulan HClNSC-77213 HClnatulanhydrochlorideibenzmethyzinhydrochloride
NCI-C01810DTXSID3021190XH0NPH5ZX8p-(N'-Methylhydrazinomethyl)-N-isopropylbenzamide hydrochlorideNSC 77213DTXCID001190Ro 4 6467/1RO-4-6467 HYDROCHLORIDE
Database identifiers
- CAS
366-70-1- PubChem CID
- 9703
- DTXSID
DTXSID3021190- ChEMBL
CHEMBL1200410- ChEBI
CHEBI:71428- UNII
- XH0NPH5ZX8
- EC Number
Properties
Computed structural properties
- Topological polar surface area
- 53.2 Ų
- Hydrogen bond donors
- 4
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 5
- Heavy atoms
- 17
- Formal charge
- 0
- Complexity
- 210
Experimental & physicochemical properties
Solubilitygreater than or equal to 100 mg/mL at 70.7 °F (NTP, 1992)
Human Drugs
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Melting Point433 °F (decomposes) (NTP, 1992)
Physical DescriptionProcarbazine hydrochloride is a white to pale yellow crystalline powder with a slight odor. Acid to litmus. (NTP, 1992)
Physicochemical properties
- Melting point
- 223 °C · 223°C
- Density
- 8.3 g/cm3 · 8.3 g/cm3
- storage temp.
- 2 · Inert atmosphere,2-8°C
- solubility
- 18 mg/mL · DMSO: ≥18mg/mL
- form
- powder
- color
- white to tan
- Water Solubility
- 10 g/100 · >=10 g/100 mL at 21.5 ºC
- Merck
- 14 · 14,7758
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Danger
H302 (97.6%): Harmful if swallowed [Warning Acute toxicity, oral]
P203, P264, P270, P280, P301+P317, P318, P330, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 41 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory InformationHazard Traits - Carcinogenicity; Developmental Toxicity
Fire HazardsFlash point data for this chemical are not available; however, it is probably combustible. (NTP, 1992)
Health Hazards
SYMPTOMS: Symptoms of exposure to this compound may include nausea, vomiting, leukopenia and thrombocytopenia. Other symptoms include somnolence, lethargy, hallucinations, confusion, agitation, cerebellar ataxia, paresthesias, myalgia, decrease of deep tendon reflexes, hypotension and allergic skin reactions. Exposure may cause arthralgia, fever, weakness, dermatitis, coma, alopecia and convulsions. It may also cause anorexia, stomatitis, diarrhea, drowsiness and depression. Other symptoms include bone marrow depression, hemolysis, bleeding tendencies, psychoses, dizziness, peripheral neuropathy, tremors, flu-like syndrome, pulmonary reactions, tachycardia, ocular defects such as blurred vision and papilledema, impaired liver function, shortness of breath, pneumonitis and productive cough. It may also cause reversible depression of peripheral leukocyte and platelet counts, optic neuroretinitis and pulmonary eosinophilia. Other symptoms include hemolytic anemia, dry mouth, dysphagia, constipation, fatigue pruritus, herpes, hyperpigmentation, flushing, intercurrent infections, pleura effusion, edema, jaundice, headache, apprehension, nervousness, inability to focus, insomnia, pyrexia, hypersensitivity reactions, hemorrhage, pancytopenia eosinophilia, petechiae, purpura, epistaxis, hemoptysis, hematemesis, melena, nystagmus, urticaria, hearing loss, diaphoresis, chills, hoarseness, slurred speech, enteritis, nightmares, falling, unsteadiness, abdominal pain, syncope, retinal hemorrhage, photophobia, diplopia, hematuria, urinary frequency, nocturia, foot drop and fetal harm. Exposure to this compound and alcohol can cause flushing of the head and neck, palpitations, sweating, hypotension and dyspnea.
Chemistry & industry
Pharmacology
FDA Pharmacological Classification
PROCARBAZINE HYDROCHLORIDE
Alkylating Drug [EPC]; Alkylating Activity [MoA]
MeSH Pharmacological ClassificationSubstances that inhibit or prevent the proliferation of NEOPLASMS.
Applications
UsesProcarbazine hydrochloride USP is used to traet Hodgkin’s disease; non-Hodgkin’s lymphomas; lung cancer.
UsesAntineoplastic.
UsesAntineoplastic;DNA replication inhibitor
General DescriptionWhite to pale yellow crystalline powder with a slight odor. Acid to litmus.
General DescriptionProcarbazine is available in 50-mg tablets for oral administrationin the treatment of Hodgkin’s (part of MOPP) andnon-Hodgkin’s disease, brain cancer, and mycosis fungoides.The major mechanisms of resistance appear to beenhanced activity of DNA-repair enzymes including enhancedO-6-alkylguanine DNA transferase (AGAT),which removes the methyl group from the O-6 of guanine.The agent is rapidly and completely absorbed after oral administrationand extensively metabolized in the liver togive azo-procarbazine followed by further oxidation tomethyldiazine and the aldehyde. The parent drug andmetabolites cross the blood-brain barrier. Elimination occursin the urine mostly as metabolites with an eliminationhalf-life of 1 hour. Myelosuppression is dose limiting, generallypresenting as thrombocytopenia that may be followedby leucopenia. Glucose-6-phosphate dehydrogenasedeficient patients may develop hemolytic anemia duringprocarbazine therapy. Other adverse effects include nausea,vomiting, hypersensitivity, flulike symptoms, amenorrhea,and azoospermia. Central nervous symptom effectsmay be seen, including lethargy, confusion, neuropathies,and seizure.
Upstream & downstream products
Upstream raw materials
Related reactions
1 records
Compound notes
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