Target intelligence / Profile preview

DNA (cyclophosphamide-induced DNA adducts and crosslinks)

Molecular classification
Other, Structural molecule
01

Overview

Cyclophosphamide is an alkylating agent used in oncology and immunosuppression. It is metabolized to active forms that chemically modify DNA, primarily by attaching alkyl groups to guanine bases, resulting in monoadducts and the formation of DNA crosslinks (both interstrand and intrastrand). These changes disrupt DNA replication and transcription, inducing cell death, particularly in rapidly dividing cells. The DNA damage provides the basis for cyclophosphamide’s efficacy against cancer and immune disease, but also causes adverse effects such as mutagenesis, secondary cancers, infertility, and hemorrhagic cystitis.

Other names
DNA adducts (from cyclophosphamide)DNA crosslinks (cyclophosphamide-induced)Interstrand and intrastrand DNA crosslinks
02

Mechanism of action

Alkylation of DNA bases at the N-7 position of guanine; Formation of DNA crosslinks (interstrand and intrastrand); Irreversible DNA damage, blocking replication and transcription, ultimately leading to cell death

03

Biological functions

Blockage of DNA replicationInduction of cell death/apoptosisInduction of genotoxicity (chromosome breaks, DNA strand breaks)
04

Disease associations

Cancer (cyclophosphamide is used to induce DNA damage in cancer cells, leading to cell death)Immunosuppression (via effects on rapidly dividing immune cells)
05

Safety considerations

Genotoxicity (mutation, cancer risk)Hemorrhagic cystitis (from the acrolein metabolite)Infertility, immunosuppression, bone marrow toxicityChromosomal aberrations
06

Interacting drugs

Cyclophosphamide

1 more in the full profile.

07

Biomarkers

γH2AX (phosphorylated histone H2AX, a marker of double-strand breaks due to cyclophosphamide-induced DNA damage)

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