Procarbazine
Übersicht
Beschreibung
Procarbazin ist ein Chemotherapeutikum, das hauptsächlich zur Behandlung des Hodgkin-Lymphoms und bestimmter Arten von Hirntumoren, wie Glioblastom multiforme, eingesetzt wird . Es gehört zur Klasse der alkylierenden Agenzien, die durch die Addition von Alkylgruppen an viele elektronegative Gruppen unter den in Zellen herrschenden Bedingungen wirken . Procarbazin wurde 1969 in den Vereinigten Staaten für die medizinische Verwendung zugelassen und ist in der Liste der unentbehrlichen Arzneimittel der Weltgesundheitsorganisation enthalten .
Herstellungsmethoden
Synthesewege und Reaktionsbedingungen: Die Synthese von Procarbazin erfolgt in mehreren Schritten ausgehend von p-Tolylaldehyd. Der Prozess umfasst die Zugabe von Dibromcyanuridsäure und Isopropylamin, um Tolylisopropylamin zu erhalten. Dieser Zwischenstoff wird dann in einem organischen Reagenz gelöst, gefolgt von der Zugabe von N-Bromsuccinimid und einem Initiator. Das Gemisch wird unter Rückfluss erhitzt und das Lösungsmittel entfernt. Acetonitril und ein hydrolytisches Beschleunigungsmittel werden hinzugefügt, und das Gemisch wird unter Rückfluss erhitzt, um Formylbenzoyl-isopropylamin zu bilden. Schließlich wird Formylbenzoyl-isopropylamin mit Methylhydraziniumsulfat und Triethylamin umgesetzt, gefolgt von der Zugabe von Natriumcyanoborhydrid, was zur Bildung von Procarbazin führt .
Industrielle Produktionsmethoden: Die industrielle Produktion von Procarbazin folgt ähnlichen Synthesewegen, ist aber für höhere Ausbeuten und Effizienz optimiert. Der Prozess vermeidet die Verwendung von starken Oxidationsmitteln und starken Säuren, wodurch er umweltfreundlicher wird. Die Gesamtrückgewinnungsrate des industriellen Verfahrens beträgt etwa 52,9% .
Vorbereitungsmethoden
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% .
Analyse Chemischer Reaktionen
Arten von Reaktionen: Procarbazin unterliegt verschiedenen chemischen Reaktionen, darunter Oxidation, Reduktion und Substitution. Eine bemerkenswerte Reaktion ist die Autooxidation zu einem Azo-Derivat, das sich dann zu einem Hydrazon isomerisiert. Dieses Hydrazon unterliegt einer Hydrolyse, wodurch ein Benzaldehyd-Derivat und Methylhydrazin entstehen .
Häufige Reagenzien und Bedingungen: Zu den in den Reaktionen mit Procarbazin verwendeten Reagenzien gehören N-Bromsuccinimid, Acetonitril, hydrolytische Beschleunigungsmittel, Methylhydraziniumsulfat und Natriumcyanoborhydrid . Die Reaktionsbedingungen beinhalten typischerweise das Erhitzen unter Rückfluss und die Verwendung von organischen Lösungsmitteln.
Hauptprodukte: Zu den Hauptprodukten, die bei den Reaktionen von Procarbazin entstehen, gehören Benzaldehyd-Derivate und Methylhydrazin .
Wissenschaftliche Forschungsanwendungen
Procarbazin hat ein breites Spektrum an Anwendungen in der wissenschaftlichen Forschung, insbesondere in den Bereichen Chemie, Biologie, Medizin und Industrie. In der Medizin wird es als Bestandteil von Kombinationschemotherapie-Regimen zur Behandlung des Hodgkin-Lymphoms und von Hirntumoren eingesetzt . In der Chemie wird Procarbazin wegen seiner einzigartigen alkylierenden Eigenschaften und seiner Wechselwirkungen mit verschiedenen Nanostrukturen für Medikamententrägersysteme untersucht . In der Biologie wird es zur Untersuchung der Auswirkungen alkylierender Agenzien auf zelluläre Prozesse und die DNA-Synthese eingesetzt . Industrielle Anwendungen umfassen die Verwendung bei der Synthese anderer pharmazeutischer Verbindungen und seine Rolle bei der Entwicklung umweltfreundlicher Produktionsmethoden .
Wirkmechanismus
Der genaue Wirkmechanismus von Procarbazin ist nicht vollständig geklärt. Es ist bekannt, dass er die Synthese von Proteinen, RNA und DNA hemmt, indem er die Transmethylierung von Methylgruppen von Methionin in Transfer-RNA stört . Procarbazin wirkt auch als alkylierendes Agens, das Guanin an der O-6-Position methyliert, was zu einem DNA-Bruch und einer Hemmung der RNA- und Proteinsynthese führt .
Wirkmechanismus
The precise mechanism of action of procarbazine is not fully understood. it is known to inhibit the synthesis of protein, RNA, and DNA by interfering with the transmethylation of methyl groups of methionine into transfer RNA . This compound also works as an alkylating agent, methylating guanine at the O-6 position, which leads to DNA breakage and inhibition of RNA and protein synthesis .
Vergleich Mit ähnlichen Verbindungen
Ähnliche Verbindungen: Ähnliche Verbindungen zu Procarbazin sind Dacarbazin, Bleomycin und Nivolumab . Diese Verbindungen werden ebenfalls zur Behandlung verschiedener Krebsarten eingesetzt und haben ähnliche Wirkmechanismen wie alkylierende Agenzien oder antineoplastische Agenzien.
Eindeutigkeit: Procarbazin ist einzigartig in seiner Fähigkeit, in Kombination mit anderen Chemotherapeutika, wie Chlormethine, Vincristin und Prednison, zur Behandlung des Hodgkin-Lymphoms eingesetzt zu werden . Es zeichnet sich auch durch seine Wechselwirkung mit Nanostrukturen für Medikamententrägersysteme aus, was seine Wirksamkeit bei der gezielten Behandlung von Krebszellen erhöht .
Eigenschaften
IUPAC Name |
4-[(2-methylhydrazinyl)methyl]-N-propan-2-ylbenzamide |
Source
|
|---|---|---|
| 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
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
InChI Key |
CPTBDICYNRMXFX-UHFFFAOYSA-N |
Source
|
| 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
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Molecular Formula |
C12H19N3O |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Related CAS |
366-70-1 (mono-hydrochloride) |
Source
|
| Record name | Procarbazine [INN:BAN] | |
| Source | ChemIDplus | |
| URL | https://pubchem.ncbi.nlm.nih.gov/substance/?source=chemidplus&sourceid=0000671169 | |
| Description | ChemIDplus is a free, web search system that provides access to the structure and nomenclature authority files used for the identification of chemical substances cited in National Library of Medicine (NLM) databases, including the TOXNET system. | |
DSSTOX Substance ID |
DTXSID4021189 |
Source
|
| Record name | Procarbazine | |
| Source | EPA DSSTox | |
| URL | https://comptox.epa.gov/dashboard/DTXSID4021189 | |
| Description | DSSTox provides a high quality public chemistry resource for supporting improved predictive toxicology. | |
Molecular Weight |
221.30 g/mol |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Physical Description |
Solid |
Source
|
| 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. | |
| 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. | |
Solubility |
In water, 1,400 mg/L @ 25 °C /Estimated/, 2.28e-01 g/L |
Source
|
| Record name | Procarbazine | |
| Source | DrugBank | |
| URL | https://www.drugbank.ca/drugs/DB01168 | |
| Description | The DrugBank database is a unique bioinformatics and cheminformatics resource that combines detailed drug (i.e. chemical, pharmacological and pharmaceutical) data with comprehensive drug target (i.e. sequence, structure, and pathway) information. | |
| Explanation | Creative Common's Attribution-NonCommercial 4.0 International License (http://creativecommons.org/licenses/by-nc/4.0/legalcode) | |
| Record name | PROCARBAZINE | |
| Source | Hazardous Substances Data Bank (HSDB) | |
| URL | https://pubchem.ncbi.nlm.nih.gov/source/hsdb/3250 | |
| Description | The Hazardous Substances Data Bank (HSDB) is a toxicology database that focuses on the toxicology of potentially hazardous chemicals. It provides information on human exposure, industrial hygiene, emergency handling procedures, environmental fate, regulatory requirements, nanomaterials, and related areas. The information in HSDB has been assessed by a Scientific Review Panel. | |
| 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. | |
| 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. | |
Vapor Pressure |
8.4X10-7 mm Hg @ 25 °C /Estimated/ |
Source
|
| Record name | PROCARBAZINE | |
| Source | Hazardous Substances Data Bank (HSDB) | |
| URL | https://pubchem.ncbi.nlm.nih.gov/source/hsdb/3250 | |
| Description | The Hazardous Substances Data Bank (HSDB) is a toxicology database that focuses on the toxicology of potentially hazardous chemicals. It provides information on human exposure, industrial hygiene, emergency handling procedures, environmental fate, regulatory requirements, nanomaterials, and related areas. The information in HSDB has been assessed by a Scientific Review Panel. | |
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. |
Source
|
| Record name | Procarbazine | |
| Source | DrugBank | |
| URL | https://www.drugbank.ca/drugs/DB01168 | |
| Description | The DrugBank database is a unique bioinformatics and cheminformatics resource that combines detailed drug (i.e. chemical, pharmacological and pharmaceutical) data with comprehensive drug target (i.e. sequence, structure, and pathway) information. | |
| Explanation | Creative Common's Attribution-NonCommercial 4.0 International License (http://creativecommons.org/licenses/by-nc/4.0/legalcode) | |
| Record name | PROCARBAZINE | |
| Source | Hazardous Substances Data Bank (HSDB) | |
| URL | https://pubchem.ncbi.nlm.nih.gov/source/hsdb/3250 | |
| Description | The Hazardous Substances Data Bank (HSDB) is a toxicology database that focuses on the toxicology of potentially hazardous chemicals. It provides information on human exposure, industrial hygiene, emergency handling procedures, environmental fate, regulatory requirements, nanomaterials, and related areas. The information in HSDB has been assessed by a Scientific Review Panel. | |
CAS No. |
671-16-9, 366-70-1 |
Source
|
| Record name | Procarbazine | |
| Source | CAS Common Chemistry | |
| URL | https://commonchemistry.cas.org/detail?cas_rn=671-16-9 | |
| Description | CAS Common Chemistry is an open community resource for accessing chemical information. Nearly 500,000 chemical substances from CAS REGISTRY cover areas of community interest, including common and frequently regulated chemicals, and those relevant to high school and undergraduate chemistry classes. This chemical information, curated by our expert scientists, is provided in alignment with our mission as a division of the American Chemical Society. | |
| Explanation | The data from CAS Common Chemistry is provided under a CC-BY-NC 4.0 license, unless otherwise stated. | |
| Record name | Procarbazine [INN:BAN] | |
| Source | ChemIDplus | |
| URL | https://pubchem.ncbi.nlm.nih.gov/substance/?source=chemidplus&sourceid=0000671169 | |
| Description | ChemIDplus is a free, web search system that provides access to the structure and nomenclature authority files used for the identification of chemical substances cited in National Library of Medicine (NLM) databases, including the TOXNET system. | |
| Record name | Procarbazine | |
| Source | DrugBank | |
| URL | https://www.drugbank.ca/drugs/DB01168 | |
| Description | The DrugBank database is a unique bioinformatics and cheminformatics resource that combines detailed drug (i.e. chemical, pharmacological and pharmaceutical) data with comprehensive drug target (i.e. sequence, structure, and pathway) information. | |
| Explanation | Creative Common's Attribution-NonCommercial 4.0 International License (http://creativecommons.org/licenses/by-nc/4.0/legalcode) | |
| Record name | Procarbazine hydrochloride | |
| Source | DTP/NCI | |
| URL | https://dtp.cancer.gov/dtpstandard/servlet/dwindex?searchtype=NSC&outputformat=html&searchlist=759626 | |
| Description | The NCI Development Therapeutics Program (DTP) provides services and resources to the academic and private-sector research communities worldwide to facilitate the discovery and development of new cancer therapeutic agents. | |
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| Record name | Procarbazine | |
| Source | EPA DSSTox | |
| URL | https://comptox.epa.gov/dashboard/DTXSID4021189 | |
| Description | DSSTox provides a high quality public chemistry resource for supporting improved predictive toxicology. | |
| Record name | Procarbazine | |
| Source | European Chemicals Agency (ECHA) | |
| URL | https://echa.europa.eu/substance-information/-/substanceinfo/100.010.531 | |
| Description | The European Chemicals Agency (ECHA) is an agency of the European Union which is the driving force among regulatory authorities in implementing the EU's groundbreaking chemicals legislation for the benefit of human health and the environment as well as for innovation and competitiveness. | |
| Explanation | Use of the information, documents and data from the ECHA website is subject to the terms and conditions of this Legal Notice, and subject to other binding limitations provided for under applicable law, the information, documents and data made available on the ECHA website may be reproduced, distributed and/or used, totally or in part, for non-commercial purposes provided that ECHA is acknowledged as the source: "Source: European Chemicals Agency, http://echa.europa.eu/". Such acknowledgement must be included in each copy of the material. ECHA permits and encourages organisations and individuals to create links to the ECHA website under the following cumulative conditions: Links can only be made to webpages that provide a link to the Legal Notice page. | |
| Record name | PROCARBAZINE | |
| Source | FDA Global Substance Registration System (GSRS) | |
| URL | https://gsrs.ncats.nih.gov/ginas/app/beta/substances/35S93Y190K | |
| Description | The FDA Global Substance Registration System (GSRS) enables the efficient and accurate exchange of information on what substances are in regulated products. Instead of relying on names, which vary across regulatory domains, countries, and regions, the GSRS knowledge base makes it possible for substances to be defined by standardized, scientific descriptions. | |
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| Record name | PROCARBAZINE | |
| Source | Hazardous Substances Data Bank (HSDB) | |
| URL | https://pubchem.ncbi.nlm.nih.gov/source/hsdb/3250 | |
| Description | The Hazardous Substances Data Bank (HSDB) is a toxicology database that focuses on the toxicology of potentially hazardous chemicals. It provides information on human exposure, industrial hygiene, emergency handling procedures, environmental fate, regulatory requirements, nanomaterials, and related areas. The information in HSDB has been assessed by a Scientific Review Panel. | |
| 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. | |
| 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. | |
Melting Point |
223 °C |
Source
|
| Record name | Procarbazine | |
| Source | DrugBank | |
| URL | https://www.drugbank.ca/drugs/DB01168 | |
| Description | The DrugBank database is a unique bioinformatics and cheminformatics resource that combines detailed drug (i.e. chemical, pharmacological and pharmaceutical) data with comprehensive drug target (i.e. sequence, structure, and pathway) information. | |
| Explanation | Creative Common's Attribution-NonCommercial 4.0 International License (http://creativecommons.org/licenses/by-nc/4.0/legalcode) | |
| 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. | |
| 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. | |
Retrosynthesis Analysis
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Strategy Settings
| Precursor scoring | Relevance Heuristic |
|---|---|
| Min. plausibility | 0.01 |
| Model | Template_relevance |
| Template Set | Pistachio/Bkms_metabolic/Pistachio_ringbreaker/Reaxys/Reaxys_biocatalysis |
| Top-N result to add to graph | 6 |
Feasible Synthetic Routes
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