# Alkylating agents and antimetabolites

Source: https://onco.cc/terms/alkylating-agent/  
OnCo record `alkylating-agent` (Term). Data CC BY-NC 4.0, attribute "Data from OnCo (onco.cc)"; commercial use needs a licence.

## TL;DR

The two oldest chemotherapy families: alkylators (cyclophosphamide, temozolomide, melphalan) glue DNA strands together so cells cannot copy them; antimetabolites (5-FU, capecitabine, methotrexate, gemcitabine) are fake building blocks that jam DNA synthesis.

## Summary

Alkylating agents descend from mustard gas (nitrogen mustard, 1946): cyclophosphamide anchors lymphoma and breast regimens and lymphodepletion, temozolomide treats glioblastoma, melphalan and busulfan are transplant conditioning, and platinum drugs act similarly. Antimetabolites include fluoropyrimidines (5-FU, capecitabine, S-1) in gastrointestinal and breast cancer, methotrexate and cytarabine in leukaemia, gemcitabine in pancreatic and bladder cancer and pemetrexed in non-squamous lung cancer. Alkylators are mutagenic and cause secondary leukaemia and infertility; antimetabolite toxicity depends on enzymes such as DPD (5-FU) and can be reduced by pre-treatment genotyping.

## Fields

- Kind: Term
- Last checked: 2026-09-09
- Also known as: alkylating; alkylator; alkylators; alkylating agent; alkylating agents; alkylating chemotherapy; antimetabolite; antimetabolites; fluoropyrimidine; fluoropyrimidines; nucleoside analogue; purine analogue; vinca alkaloid; vinca alkaloids; vinca; 5-FU; purine analogues

## Sources

- Wikipedia: https://en.wikipedia.org/wiki/Alkylating_antineoplastic_agent
- Wikipedia: https://en.wikipedia.org/wiki/Alkylating_antineoplastic_agent

## Connected records

- terms: [Conditioning regimen (myeloablative, reduced-intensity)](https://onco.cc/terms/conditioning-regimen/), [FOLFOX, FOLFIRI, FOLFIRINOX and CAPOX](https://onco.cc/terms/folfox-family/), [Lymphodepletion before CAR-T](https://onco.cc/terms/lymphodepletion/), [Secondary malignancy (therapy-related cancer)](https://onco.cc/terms/secondary-malignancy/)
- fronts: [Chemotherapy](https://onco.cc/fronts/chemotherapy/)
- technologies: [Cytotoxic chemotherapy](https://onco.cc/technologies/cytotoxic-chemotherapy/)
- drugs: [Cyclophosphamide](https://onco.cc/drugs/cyclophosphamide/), [Fluorouracil (5-FU)](https://onco.cc/drugs/fluorouracil/), [Gemcitabine](https://onco.cc/drugs/gemcitabine/), [Melphalan (including hepatic delivery system)](https://onco.cc/drugs/melphalan/), [Methotrexate](https://onco.cc/drugs/methotrexate/), [Temozolomide](https://onco.cc/drugs/temozolomide/)
- biomarkers: [MGMT promoter methylation](https://onco.cc/biomarkers/mgmt-promoter-methylation/)

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