Procarbazine
Overview
Description
Procarbazine is a chemotherapy medication primarily used for the treatment of Hodgkin’s lymphoma and certain types of brain cancers, such as glioblastoma multiforme . It belongs to the class of alkylating agents, which work by adding alkyl groups to many electronegative groups under conditions present in cells . This compound was approved for medical use in the United States in 1969 and is included in the World Health Organization’s List of Essential Medicines .
Scientific Research Applications
Procarbazine has a wide range of scientific research applications, particularly in the fields of chemistry, biology, medicine, and industry. In medicine, it is used as part of combination chemotherapy regimens for treating Hodgkin’s lymphoma and brain cancers . In chemistry, this compound is studied for its unique alkylating properties and its interactions with various nanostructures for drug delivery systems . In biology, it is used to study the effects of alkylating agents on cellular processes and DNA synthesis . Industrial applications include its use in the synthesis of other pharmaceutical compounds and its role in developing environmentally friendly production methods .
Mechanism of Action
Target of Action
Procarbazine primarily targets the DNA in cells . It acts as an alkylating agent, adding alkyl groups to many electronegative groups under conditions present in cells .
Mode of Action
It is known that this compound works, in part, by methylating guanine at the o-6 position . Guanine is one of the four nucleotides that make up DNA. The methylated DNA is prone to breakage, and RNA and protein synthesis is inhibited .
Biochemical Pathways
This compound affects the biochemical pathways involved in DNA, RNA, and protein synthesis . By methylating guanine, a key component of DNA, this compound disrupts the normal function of DNA. This leads to DNA breakage and inhibition of RNA and protein synthesis, which can result in cell death .
Pharmacokinetics
This compound is typically taken orally . It is metabolized in the liver and kidneys, and has an elimination half-life of approximately 10 minutes . The drug’s ADME (Absorption, Distribution, Metabolism, and Excretion) properties impact its bioavailability, with metabolism in the liver and kidneys playing a key role .
Result of Action
The molecular and cellular effects of this compound’s action include DNA breakage and inhibition of RNA and protein synthesis . These effects can lead to cell death, particularly in rapidly dividing cells such as cancer cells .
Action Environment
The action, efficacy, and stability of this compound can be influenced by environmental factors. For example, the drug’s effectiveness can be affected by the patient’s liver and kidney function, as these organs play a key role in the drug’s metabolism . Additionally, research suggests that the chemical reactivity and adsorption properties of this compound can be influenced by factors such as pH .
Safety and Hazards
Procarbazine can increase the risk of bleeding or infection . It is classified as very toxic if swallowed, irritating to skin, risk of serious damages to eyes, toxic; danger of serious damage to health by prolonged exposure, possible risk of impaired fertility, and possible risk of harm to unborn child . It may cause anemia, cough, CNS depression, drowsiness, headache, heart damage, lassitude (weakness, exhaustion), liver damage, narcosis, reproductive effects, teratogenic effects .
Future Directions
Recent advances in molecular-based classification, imaging, and targeted therapies will hopefully improve survival and quality of life for patients with IDH-mutant low-grade gliomas, a type of brain cancer that procarbazine is used to treat . There is hope that improved neuroimaging biomarkers will allow better assessment of disease response to experimental therapies .
Biochemical Analysis
Biochemical Properties
Procarbazine plays a crucial role in biochemical reactions by inhibiting the synthesis of DNA, RNA, and proteins. It interacts with various enzymes and biomolecules, including cytochrome P450 oxidoreductase and mitochondrial monoamine oxidase. These interactions lead to the formation of active metabolites, such as azo- and methylazoxy-metabolites, which contribute to its antineoplastic effects . This compound also inhibits the transmethylation of methionine into transfer RNA, thereby preventing protein synthesis .
Cellular Effects
This compound exerts significant effects on various types of cells and cellular processes. It inhibits cell proliferation by interfering with DNA replication and transcription. This compound also affects cell signaling pathways, gene expression, and cellular metabolism. This compound’s impact on cell function includes the induction of apoptosis (programmed cell death) and the inhibition of mitosis . Additionally, it has been shown to cause free-radical damage to DNA, further contributing to its cytotoxic effects .
Molecular Mechanism
At the molecular level, this compound acts as an alkylating agent, methylating guanine at the O-6 position in DNA. This methylation leads to DNA strand breakage and inhibits RNA and protein synthesis . This compound also inhibits the transmethylation of methionine into transfer RNA, which is essential for protein synthesis . These molecular interactions result in the disruption of cellular processes and the eventual death of cancer cells.
Temporal Effects in Laboratory Settings
In laboratory settings, the effects of this compound change over time. The compound is rapidly metabolized, with a half-life of approximately 10 minutes . Its stability and degradation are influenced by various factors, including the presence of enzymes and the cellular environment. Long-term effects of this compound on cellular function have been observed in both in vitro and in vivo studies, with prolonged exposure leading to increased cytotoxicity and apoptosis .
Dosage Effects in Animal Models
The effects of this compound vary with different dosages in animal models. At lower doses, it has been shown to be an effective immunosuppressant, prolonging the survival of skin grafts in mice, rats, and rabbits . At higher doses, this compound can cause significant toxicity, including genomic damage and infertility . These dose-dependent effects highlight the importance of careful dosage management in therapeutic settings.
Metabolic Pathways
This compound is metabolized primarily in the liver and kidneys. The drug undergoes auto-oxidation to form an azo derivative, which is further metabolized to a hydrazone. This hydrazone is hydrolyzed to produce a benzylaldehyde derivative and methylhydrazine . The metabolic activation of this compound involves cytochrome P450 enzymes, which facilitate the formation of reactive intermediates that bind covalently to cellular macromolecules .
Transport and Distribution
This compound is readily absorbed and distributed throughout the body. It crosses the blood-brain barrier and equilibrates between plasma and cerebrospinal fluid following oral administration . The compound is also distributed into the liver, kidneys, intestinal wall, and skin. This compound’s distribution is influenced by its interactions with transporters and binding proteins, which affect its localization and accumulation within tissues .
Subcellular Localization
This compound’s subcellular localization is critical for its activity and function. It is distributed rapidly within cells, including the liver, kidneys, and intestinal wall . The compound’s localization is influenced by targeting signals and post-translational modifications that direct it to specific compartments or organelles. These factors play a role in this compound’s ability to inhibit DNA, RNA, and protein synthesis, ultimately leading to its cytotoxic effects .
Preparation Methods
Synthetic Routes and Reaction Conditions: The synthesis of procarbazine involves several steps starting from p-tolyl aldehyde. The process includes the addition of dibromo cyanuric acid and isopropylamine to obtain toluyl isopropylamine. This intermediate is then dissolved in an organic reagent, followed by the addition of N-bromo-succinimide and an initiator. The mixture is heated to reflux, and the solvent is removed. Acetonitrile and a hydrolytic accelerating agent are added, and the mixture is heated to reflux to form formoxyl benzoyl isopropyl amine. Finally, formoxyl benzoyl isopropyl amine is reacted with methylhydrazinium sulphate and triethylamine, followed by the addition of sodium cyanoborohydride, resulting in the formation of this compound .
Industrial Production Methods: Industrial production of this compound follows similar synthetic routes but is optimized for higher yields and efficiency. The process avoids the use of strong oxidizers and strong acids, making it more environmentally friendly. The total recovery rate of the industrial method is approximately 52.9% .
Chemical Reactions Analysis
Types of Reactions: Procarbazine undergoes various chemical reactions, including oxidation, reduction, and substitution. One notable reaction is its auto-oxidation to form an azo derivative, which then isomerizes to a hydrazone. This hydrazone undergoes hydrolysis to produce a benzylaldehyde derivative and methylhydrazine .
Common Reagents and Conditions: Common reagents used in the reactions involving this compound include N-bromo-succinimide, acetonitrile, hydrolytic accelerating agents, methylhydrazinium sulphate, and sodium cyanoborohydride . Reaction conditions typically involve heating to reflux and the use of organic solvents.
Major Products: The major products formed from the reactions of this compound include benzylaldehyde derivatives and methylhydrazine .
Comparison with Similar Compounds
Similar Compounds: Similar compounds to procarbazine include dacarbazine, bleomycin, and nivolumab . These compounds are also used in the treatment of various cancers and have similar mechanisms of action as alkylating agents or antineoplastic agents.
Uniqueness: This compound is unique in its ability to be used in combination with other chemotherapeutic agents, such as chlormethine, vincristine, and prednisone, for the treatment of Hodgkin’s lymphoma . It is also distinct in its interaction with nanostructures for drug delivery systems, which enhances its effectiveness in targeting cancer cells .
Properties
IUPAC Name |
4-[(2-methylhydrazinyl)methyl]-N-propan-2-ylbenzamide | |
---|---|---|
Source | PubChem | |
URL | https://pubchem.ncbi.nlm.nih.gov | |
Description | Data deposited in or computed by PubChem | |
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) | |
Source | PubChem | |
URL | https://pubchem.ncbi.nlm.nih.gov | |
Description | Data deposited in or computed by PubChem | |
InChI Key |
CPTBDICYNRMXFX-UHFFFAOYSA-N | |
Source | PubChem | |
URL | https://pubchem.ncbi.nlm.nih.gov | |
Description | Data deposited in or computed by PubChem | |
Canonical SMILES |
CC(C)NC(=O)C1=CC=C(C=C1)CNNC | |
Source | PubChem | |
URL | https://pubchem.ncbi.nlm.nih.gov | |
Description | Data deposited in or computed by PubChem | |
Molecular Formula |
C12H19N3O | |
Source | PubChem | |
URL | https://pubchem.ncbi.nlm.nih.gov | |
Description | Data deposited in or computed by PubChem | |
Related CAS |
366-70-1 (mono-hydrochloride) | |
Record name | Procarbazine [INN:BAN] | |
Source | ChemIDplus | |
URL | https://pubchem.ncbi.nlm.nih.gov/substance/?source=chemidplus&sourceid=0000671169 | |
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DSSTOX Substance ID |
DTXSID4021189 | |
Record name | Procarbazine | |
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Molecular Weight |
221.30 g/mol | |
Source | PubChem | |
URL | https://pubchem.ncbi.nlm.nih.gov | |
Description | Data deposited in or computed by PubChem | |
Physical Description |
Solid | |
Record name | Procarbazine | |
Source | Human Metabolome Database (HMDB) | |
URL | http://www.hmdb.ca/metabolites/HMDB0015299 | |
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Solubility |
In water, 1,400 mg/L @ 25 °C /Estimated/, 2.28e-01 g/L | |
Record name | Procarbazine | |
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Record name | Procarbazine | |
Source | Human Metabolome Database (HMDB) | |
URL | http://www.hmdb.ca/metabolites/HMDB0015299 | |
Description | The Human Metabolome Database (HMDB) is a freely available electronic database containing detailed information about small molecule metabolites found in the human body. | |
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Vapor Pressure |
8.4X10-7 mm Hg @ 25 °C /Estimated/ | |
Record name | PROCARBAZINE | |
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Mechanism of Action |
The 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., Procarbazine is an alkylating agent. The exact mechanism of antineoplastic action is unknown but is thought to resemble that of the alkylating agents; procarbazine is cell cycle-specific for the S phase of cell division. Procarbazine is thought to inhibit DNA, RNA, and protein synthesis., O-6-Methylguanine was measured in blood leukocyte DNA of seven patients with Hodgkin's or non-Hodgkin's lymphoma during therapeutic exposure to procarbazine involving three daily p.o. doses (50 mg each) for 10 days (corresponding to 2.1 mg/kg/day for a 70-kg human). Adduct accumulation was observed in all seven cases, reaching levels up to 0.28 fmol/microgram of DNA (0.45 umol/mol of guanine). In one individual, maximal levels of adduct were reached after 7 days of exposure, followed by a steady decline, whereas in all other individuals continuous accumulation was observed throughout the exposure period. In four individuals for which data were available for day 11 (12 to 16 hr after the final intake of procarbazine), decreased amounts of O-6-methylguanine were observed relative to the last previous measurements. The accumulation of O-6-methylguanine was linearly correlated with the cumulative dose of procarbazine, with a slope of 0.011 fmol of O-6-methylguanine/microgram of DNA per mg/kg of body weight or 2.68x10-4 fmol of O-6-methylguanine DNA per mg/sq m. Two hr after the administration of single p.o. doses of l to 10 mg/kg of procarbazine to rats, O-6-methylguanine formation in leukocyte DNA was just under half that in liver DNA and showed a linear relationship with dose with a slope of 0.017 fmol/microgram of DNA per mg/kg of body weight or 5.67x10-4 fmol of O-6-methylguanine/microgram of DNA per mg/sq m. A negative correlation between the rate of accumulation of O-6-methylguanine in different individuals and lymphocyte O-6-alkylguanine-DNA alkyltransferase was observed, demonstrating a probable protective effect of O-6-alkylguanine-DNA alkyltransferase against the accumulation of O-6-methylguanine during exposure to methylating agents. This observation supports the suggestion of a possible role of procarbazine-induced O-6-methylguanine in the pathogenesis of acute nonlymphocytic leukemia appearing after treatment with chemotherapeutic protocols which include procarbazine, based on the finding of low lymphocyte O-6-alkylguanine-DNA alkyltransferase levels in patients with such therapy-related neoplastic disease. Lymphocyte O-6-alkylguanine-DNA alkyltransferase levels were mainly in the range of 5 to 10 fmol/micrograms of DNA and showed no consistent variation during procarbazine exposure., Procarbazine causes weak inhibition of monoamine oxidase (MAO). MAO inhibitors prevent the inactivation of tyramine by hepatic and gastrointestinal monoamine oxidase. Tyramine in the bloodstream releases norepinephrine from the sympathetic nerve terminals and produces a sudden increase in blood pressure. | |
Record name | Procarbazine | |
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CAS No. |
671-16-9, 366-70-1 | |
Record name | Procarbazine | |
Source | CAS Common Chemistry | |
URL | https://commonchemistry.cas.org/detail?cas_rn=671-16-9 | |
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Record name | Procarbazine [INN:BAN] | |
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Record name | Procarbazine | |
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Record name | Procarbazine | |
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Melting Point |
223 °C | |
Record name | Procarbazine | |
Source | DrugBank | |
URL | https://www.drugbank.ca/drugs/DB01168 | |
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Record name | Procarbazine | |
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URL | http://www.hmdb.ca/metabolites/HMDB0015299 | |
Description | The Human Metabolome Database (HMDB) is a freely available electronic database containing detailed information about small molecule metabolites found in the human body. | |
Explanation | HMDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (HMDB) and the original publication (see the HMDB citing page). We ask that users who download significant portions of the database cite the HMDB paper in any resulting publications. | |
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