II. Mechanism
- Alkylating Agents are not Cell Cycle specific
- Exert cytotoxic effects via transfer of unstable alkyl group
- DNA alkylation (key to cellular lethality, esp. DNA cross linking)
- Chemically react with other cellular constituents (e.g. Proteins)
- Replicating cells and rapidly growing cells are most susceptible to agents (related to adverse effects)
- Blood cell precursors
- Hair cells
- Gastrointestinal cells
- Cancer resistance mechanisms
- Decreased Chemotherapeutic Drug uptake
- Repair of DNA damage
III. Medications
- Nitrogen Mustard Antineoplastic Compounds (Bis -chloroethyl- amines)
- Bendamustine
- Chlorambucil
- Cyclophosphamide (prodrug, activated in liver)
- Ifosfamide (prodrug, activated in liver)
- Mechlorethamine
- Melphalan
- Nitrosourea Compounds
- Carmustine (BCNU)
- Lomustine (CCNU)
- Semustine (Methyl-CCNU)
- Streptozocin
- Aziridines (Ethyleneimine)
- Thiotepa
- Triethylenemelamine
- Mesylate (Alkylsulfonate)
- Triazene Antineoplastic
- Procarbazine
- Dacarbazine
- Temozolamide
- Platinum Analogs
- Other drugs causing alkylation
- Hexamethylmelamine
- Trabectedin
IV. References
- Olson (2020) Clinical Pharmacology, Medmaster, Miami, Fl, p. 126
- Amjad (2023) Cancer Chemotherapy, StatPearls, Treasure Island, Fl, accessed 2/1/3/2024
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Related Studies
| Definition (CSP) | any compound of the type R-SO3-. |
| Definition (MSH) | Organic esters or salts of sulfonic acid derivatives containing an aliphatic hydrocarbon radical. |
| Concepts | Organic Chemical (T109) |
| MSH | D000476 |
| English | Alkyl Sulfonates, Sulfonates, Alkyl, alkyl sulfonate, Alkanesulfonates [Chemical/Ingredient], sulfonate, sulfonated, sulfonates, Alkanesulfonates, alkylsulfonate |
| Swedish | Alkansulfonater |
| Czech | alkylsulfonany |
| Finnish | Alkaanisulfonaatit |
| Italian | Alchilsolfonati, Alcansolfonati |
| Russian | ALKILSUL'FONATY, ALKANSUL'FONATY, АЛКАНСУЛЬФОНАТЫ, АЛКИЛСУЛЬФОНАТЫ |
| French | Alcanesulfonates |
| Croatian | Not Translated[Alkanesulfonates] |
| Polish | Alkanosulfoniany |
| Japanese | アルカンスルホン酸塩, アルカンスルホン酸エステル, アルカンスルホナート, アルキルスルホン酸エステル, アルキルスルホナート, アルキルスルホン酸塩 |
| German | Alkansulfonate, Alkylsulfonate |
| Portuguese | Alcanossulfonatos, Sulfonatos de Alquila |
| Spanish | Alcanosulfonatos, Sulfonatos de Alquilo |
Ontology: Alkylating Agents (C0002073)
| Definition (NCI) | Agents that replace hydrogen atom(s) in biologically active molecules with alky radical(s), hindering proper function. Alkylating agents exhibit cytotoxic effects through the alkylation of DNA, resulting in strand cross-linking, ultimately inhibiting DNA replication and cell growth. |
| Definition (NCI_NCI-GLOSS) | A type of drug that is used in the treatment of cancer. It interferes with the cell's DNA and inhibits cancer cell growth. |
| Definition (MSH) | Highly reactive chemicals that introduce alkyl radicals into biologically active molecules and thereby prevent their proper functioning. Many are used as antineoplastic agents, but most are very toxic, with carcinogenic, mutagenic, teratogenic, and immunosuppressant actions. They have also been used as components in poison gases. |
| Definition (CSP) | chemical agent that can add alkyl groups (for example, ethyl or methyl groups) to another molecule; many mutagens act through alkylation. |
| Concepts | Pharmacologic Substance (T121) , Hazardous or Poisonous Substance (T131) |
| MSH | D000477 |
| SnomedCT | 19768003, 372669002 |
| English | Agents, Alkylating, Alkylators, alkylating agents, alkylating agents (medication), Alkylating Agents, alkylating drug, alkylating drugs, agents alkylating, ALKYLATING AGENTS, Alkylating agents, Alkylating drugs, Alkylating agent (product), Alkylating agent (substance), Alkylating agent, alkylating agent, Alkylating agent, NOS, Alkylating Agent, Alkylator |
| French | Alkylants, Agents alkoylants, Agents alkylants, Alcoylants, Agents alcoylants |
| Swedish | Alkylerande medel |
| Czech | alkylační látky |
| Finnish | Alkyloivat aineet |
| Russian | ALKILIRUIUSHCHIE SREDSTVA, АЛКИЛИРУЮЩИЕ СРЕДСТВА |
| Japanese | アルキル化剤, アルキル化薬 |
| Croatian | ALKILIRAJUĆA SREDSTVA |
| Polish | Leki alkilujące |
| Spanish | Alquilantes, Agentes Alquilantes, Agentes Alcoylantes, agente alquilante (producto), agente alquilante (sustancia), agente alquilante |
| Italian | Alchilanti, Agenti alchilanti |
| Portuguese | Agentes Alquilantes, Agentes Alcoilantes, Alquilantes |
| German | Alkylierende Stoffe |
Ontology: Mesylates (C0025619)
| Definition (MSH) | Organic salts or esters of methanesulfonic acid. |
| Definition (CSP) | corrosive, toxic acid or its salts or esters, used as a catalyst and as a solvent. |
| Concepts | Organic Chemical (T109) |
| MSH | D008698 |
| English | Methanesulfonates, Methylenesulfonates, Mesylates, methane sulfonate, Mesylates [Chemical/Ingredient], mesylate, mesylates, mesilate, Mesilates, Mesylate, Mesilate |
| Swedish | Mesylater |
| Czech | methansulfonáty |
| Finnish | Mesylaatit |
| Russian | METANSUL'FONATY, METILSUL'FONATY, METILENSUL'FONATY, MEZILATY, МЕЗИЛАТЫ, МЕТАНСУЛЬФОНАТЫ, МЕТИЛЕНСУЛЬФОНАТЫ, МЕТИЛСУЛЬФОНАТЫ |
| Croatian | Not Translated[Mesylates] |
| Polish | Metylosulfoniany, Mesylates |
| Japanese | メシラート, メシル酸塩, メタンスルホナート, メチレンスルフォネート, メシレート, メタンスルホネート, メタンスルホン酸塩, メチレンスルホネート, メチレンスルホン酸塩 |
| French | Mésylates, Mésilates, Méthanesulfonates |
| German | Mesylate, Methansulfonate, Mesilat |
| Italian | Mesilati |
| Portuguese | Mesilato, Mesilatos, Metanossulfonatos |
| Spanish | Mesilato, Mesilatos, Metanosulfonatos |
Ontology: Nitrosourea Compounds (C0028210)
| Definition (NCI) | Any of a class of alkylating agents that contain both a nitroso group and a urea. They are lipophilic and can cross the blood-brain barrier. |
| Definition (NCI_NCI-GLOSS) | An anticancer drug that can cross the blood-brain barrier. Carmustine and lomustine are nitrosoureas. |
| Concepts | Organic Chemical (T109) , Pharmacologic Substance (T121) |
| MSH | D009607 |
| SnomedCT | 349843000, 372610009 |
| English | Compounds, Nitrosourea, Nitrosourea Compounds, NITROSOUREA CPDS, Nitrosourea Compounds [Chemical/Ingredient], nitrosoureas, nitrosurea, nitrosureas, Nitrosureas, Nitrosureas (product), Nitrosureas (substance), nitrosourea, Nitrosoureas, Nitrosourea Compound |
| Swedish | Nitrosureaföreningar |
| Czech | nitrosomočovinové sloučeniny |
| Finnish | Nitrosoureayhdisteet |
| Russian | NITROZOMOCHEVINY SOEDINENIIA, НИТРОЗОМОЧЕВИНЫ СОЕДИНЕНИЯ |
| Croatian | NITROZOUREJA SPOJEVI |
| Spanish | nitrosureas, nitrosureas (sustancia), nitrosoureas (sustancia), nitrosoureas (producto), nitrosoureas, Compuestos de Nitrosourea |
| Polish | Nitrozomocznika związki |
| French | Nitrosourées, Nitroso-urées |
| Portuguese | Compostos de Nitrosoureia |
| German | Nitrosoharnstoffverbindungen |
| Italian | Composti della nitrosourea |
Ontology: aziridine (C0052794)
| Definition (NCI) | A monofunctional alkylating agent with potential antineoplastic activity. Reacting with DNA mainly at guanine and adenine residues, ethylenimine alkylates DNA, thereby producing DNA interstrand crosslinks and DNA breaks, and interfering with DNA replication and cell division. (NCI04) |
| Definition (CSP) | saturated, 3-membered organic ring system with 1 nitrogen heteroatom. |
| Concepts | Organic Chemical (T109) |
| MSH | C033132 |
| SnomedCT | 84212004 |
| LNC | LP34809-1, MTHU017187 |
| English | aziridine, ethyleneimine, ethylenimine, azacyclopropane, Ethyleneimine, ETHYLENEIMINE, Azacyclopropane, Aziridine, Ethylenimine, Ethylenimine (substance), Azirane, Dimethyleneimine, Dimethylenimine, Ethylimine, Aminoethylene |
| Spanish | azaciclopropano, aziridina, etilenimina (sustancia), etilenimina |
Ontology: Triazene antineoplastic (C0360111)
| Concepts | Pharmacologic Substance (T121) , Organic Chemical (T109) |
| SnomedCT | 349844006, 372611008 |
| English | Triazene antineoplastic, Triazene antineoplastic (product), Triazene antineoplastic (substance) |
| Spanish | antineoplásico del grupo triazeno (sustancia), antineoplásico del grupo triazeno, triaceno, agente antineoplásico (producto), triaceno, agente antineoplásico (sustancia), triaceno, agente antineoplásico, triazeno, agente antineoplásico |
Ontology: Platinum Antineoplastic Compound (C3536920)
| Definition (NCI) | A chemotherapy compound that contains a platinum atom. Platinum compounds do not contain alkyl groups but do cause DNA crosslinks and adducts similar to alkylating agents. DNA crosslinks and adducts ultimately lead to the induction of apoptosis. |
| Concepts | Pharmacologic Substance (T121) |
| English | Platinum Antineoplastic Compound, Platinum compounds, antineoplastic drugs, Platinum compounds, Platinum Agents, Platinum Compound |
Ontology: Nitrogen Mustard Antineoplastic Compounds (C3537003)
| Definition (NCI) | A mustard agent containing nitrogen and chlorine atoms. |
| Concepts | Organic Chemical (T109) , Pharmacologic Substance (T121) |
| SnomedCT | 349842005, 372609004 |
| English | nitrogen mustards (medication), nitrogen mustard compound, nitrogen mustards, Nitrogen Mustard Compounds [Chemical/Ingredient], Nitrogen Mustard Compounds, Nitrogen Mustard Antineoplastic Compounds, Nitrogen mustard derivative, Nitrogen mustard derivative (product), Nitrogen mustard derivative (substance), Nitrogen Mustard Compound |
| Spanish | derivado de la mostaza nitrogenada (producto), derivado de la mostaza nitrogenada (sustancia), derivado de la mostaza nitrogenada, derivado de mostaza nitrogenada (sustancia), derivado de mostaza nitrogenada |
