366-70-1

Basic information

• Product Name: Procarbazine hydrochloride
• Synonyms: n-(1-methylethyl)-4-((2-methylhydrazino)methyl)benzamide hydrochloride;PROCARBAZINE HCL;PROCARBAZINE HYDROCHLORIDE;1-(p-isopropylcarbamoylbenzyl)-2-methylhydrazinehydrochloride;1-methyl-2-(p-isopropylcarbamoylbenzyl)hydrazinehydrochloride;1-methyl-2-p-(isopropylcarbamyol)benzohydrazinehydrochloride;2-(p-(isopropylcarbamoyl)benzyl)-1-methylhydrazinehydrochloride;chlorhydratede1-methyl2p(isopropylcarbamoyl)benzyl-hydrazine
• CAS NO: 366-70-1
• Molecular Formula: C₁₂H₁₉N₃O*ClH
• Molecular Weight: 257.76
• EINECS: 206-678-6
• Product Categories: Intermediates & Fine Chemicals;Pharmaceuticals;API;Matulane
• Mol File: 366-70-1.mol
• Article Data: 2

Chemical Properties

• Melting Point: 223°C
• Boiling Point: 384.6 °C at 760 mmHg
• Flash Point: 148.9 °C
• Appearance: white to tan/
• Density: 8.3 g/cm3
• Vapor Pressure: 4.05E-06mmHg at 25°C
• Storage Temp.: -20°C Freezer
• Solubility: DMSO: ≥18mg/mL
• Water Solubility: >=10 g/100 mL at 21.5 ºC
• Merck: 14,7758
• CAS DataBase Reference: Procarbazine hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: Procarbazine hydrochloride(366-70-1)
• EPA Substance Registry System: Procarbazine hydrochloride(366-70-1)

Safety Data

• Hazard Codes: T
• Statements: 45-61-22-68
• Safety Statements: 53-36/37-45
• WGK Germany: 3
• RTECS: XS4725000
• Hazardous Substances Data: 366-70-1(Hazardous Substances Data)

Usage

Description

Procarbazine hydrochloride, also known as Matulane, is a white to pale yellow crystalline powder with a slight odor. It is an antineoplastic chemotherapy drug that is used for the treatment of various types of cancer, including Hodgkin's lymphoma. It works by inhibiting DNA replication and has a rapid and complete absorption after oral administration. The drug is metabolized in the liver and crosses the blood-brain barrier. The major mechanisms of resistance to procarbazine hydrochloride include enhanced activity of DNA-repair enzymes. Adverse effects of the drug may include myelosuppression, nausea, vomiting, hypersensitivity, flu-like symptoms, amenorrhea, azoospermia, and central nervous system effects such as lethargy, confusion, neuropathies, and seizures.

Uses

1. Used in Anticancer Applications:
Procarbazine hydrochloride is used as an antineoplastic agent for the treatment of Hodgkin's disease, non-Hodgkin's lymphomas, and lung cancer. It is particularly effective against solid malignancies and works by inhibiting DNA replication, leading to the breaking of DNA strands and preventing tumor growth and progression.
2. Used in Hodgkin's Lymphoma Treatment:
Procarbazine hydrochloride is used as a component of the MOPP (mechlorethamine, vincristine, procarbazine, and prednisone) regimen, which is a standard chemotherapy treatment for Hodgkin's lymphoma. It is effective in treating this type of cancer due to its antineoplastic properties and ability to inhibit DNA replication.
3. Used in Brain Cancer Treatment:
Procarbazine hydrochloride is used as an antineoplastic agent for the treatment of brain cancer. Its ability to cross the blood-brain barrier makes it a valuable drug in this application, as it can directly target cancer cells in the brain and inhibit their growth.
4. Used in Mycosis Fungoides Treatment:
Procarbazine hydrochloride is used as an antineoplastic agent for the treatment of mycosis fungoides, a rare type of skin cancer. Its antineoplastic properties and DNA replication inhibition make it an effective treatment option for this condition.
5. Used in DNA Repair Inhibition:
Procarbazine hydrochloride is used as a DNA replication inhibitor, which contributes to its antineoplastic effects. By inhibiting DNA replication, the drug prevents cancer cells from dividing and proliferating, ultimately leading to the suppression of tumor growth.

Air & Water Reactions

In the presence of moisture or in aqueous solution undergoes oxidation by atmospheric oxygen. Water soluble.

Reactivity Profile

Procarbazine hydrochloride is very sensitive to light. Stability is highest in aqueous acid and decreases with increasing pH. Degrades rapidly in alcoholic media and more slowly in aqueous media .

Fire Hazard

Flash point data for Procarbazine hydrochloride are not available; however, Procarbazine hydrochloride is probably combustible.

Safety Profile

Confirmed carcinogen with experimental carcinogenic, neoplastigenic, tumorigenic, and teratogenic data. Poison by an unspecified route. Moderately toxic by ingestion, subcutaneous, intravenous, and intraperitoneal routes. Experimental reproductive effects. Mutation data reported. When heated to decomposition it emits very toxic fumes of NOx and HCl. Used as a chemotherapeutic agent.

Potential Exposure

Procarbazine is available in capsule form. The primary use of this drug is as an antineoplastic agent in the treatment of advanced Hodgkin’s disease, and oat-cell carcinoma of the lung. The hydrochloride com- pound is used in treatment. The FDA approved use of pro- carbazine hydrochloride in 1969 and indicated that the drug should be used as an adjunct to standard therapy. Possible exposure occurs during manufacture of the drug and direct exposure during its subsequent administration to patients. Some of the metabolites of procarbazine hydrochloride are both carcinostatic and carcinogenic.

Veterinary Drugs and Treatments

In veterinary medicine, procarbazine is used as part of MOPP protocols (mechlorethamine, vincristine, procarbazine, prednisone) to treat lymphomas in dogs and cats. It may be of benefit in treating granulomatous meningoencephalitis (GME) in dogs.

Shipping

UN2811 Toxic solids, organic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name Required.

Incompatibilities

Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides.

Waste Disposal

It is inappropriate and possibly dangerous to the environment to dispose of expired or waste drugs and pharmaceuticals by flushing them down the toilet or discarding them to the trash. Household quantities of expired or waste pharmaceuticals may be mixed with wet cat litter or coffee grounds, double-bagged in plastic, discard in trash. Larger quanti- ties shall carefully take into consideration applicable DEA, EPA, and FDA regulations. If possible return the pharmaceutical to the manufacturer for proper disposal being careful to properly label and securely package the material. Alternatively, the waste pharmaceutical shall be labeled, securely packaged and transported by a state licensed medical waste contractor to dispose by burial in a licensed hazardous or toxic waste landfill or incinerator.

InChI:InChI=1/C12H19N3O.ClH/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);1H

Relevant articles and documents

Method of treating nausea and vomiting with certain substituted-phenylalkylamino (and aminoacid) derivatives and other serotonin depleting agents

A method for the treatment of emesis in a mammal, which method comprises administering to said mammal an emesis inhibiting amount of a compound which depletes serotonin in the brain of mammals; among which are compounds having the formula: STR1 wherein, R is selected from hydrogen, loweralkyl, trifluoromethyl, carboxyl, or loweralkoxycarbonyl; R1 and R2 are hydrogen or loweralkyl; Z is trifluoromethyl or halogen; the optical isomers and pharmaceutically acceptable salts thereof; two of the preferred compounds of the invention are fenfluramine and norfenfluramine.