Cyclophosphamide
Cyclophosphamide is a cyclic phosphoramide mustard containing a six-membered phosphorin ring substituted with a 2-chloroethylamino group and a phosphate ester moiety. The molecule exhibits a prodrug configuration, metabolizing to phosphoramide mustard via hepatic oxidation. Key structural features include a chiral ethylene bridge and a labile phosphate ester linkage. Its alkylating activity arises from the chloroethyl side chain, which undergoes metabolic cleavage. This compound serves as the direct API precursor for antineoplastic formulations and is utilized as an HPLC reference standard for quantitative analysis in pharmaceutical quality control.
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Molecular Formula
C7H15Cl2N2O2P
Molecular Weight
261.0800
CAS Number
50-18-0
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PubChem CID
2907 ↗
IUPAC Name
N,N-bis(2-chloroethyl)-2-oxo-1,3,2lambda5-oxazaphosphinan-2-amine
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📝 Synonyms
cyclophosphamide
50-18-0
Cytoxan
Cyclophosphamid
Cyclophosphane
Clafen
Endoxan
Cyclophosphan
Cytophosphan
Procytox
🔬 Chemical Identifiers
C1CNP(=O)(OC1)N(CCCl)CCCl
InChI=1S/C7H15Cl2N2O2P/c8-2-5-11(6-3-9)14(12)10-4-1-7-13-14/h1-7H2,(H,10,12)
CMSMOCZEIVJLDB-UHFFFAOYSA-N
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