4-Hydroxycyclophosphamide

Tetrahydro-2-(bis(2-chloroethyl)amino)-2H-1,3,2-oxazaphosphorin-4-ol 2-oxide

Formula: C7H15Cl2N2O3P (276.0197)
Chinese Name: (R,S)-4-羟基环磷酰胺
BioDeep ID: BioDeep_00000006562 ( View LC/MS Profile)
SMILES: O=P1(N(CCCl)CCCl)NC(O)CCO1



Found 5 Sample Hits

m/z Adducts Species Organ Scanning Sample
294.0499 [M+NH4]+
PPM:12.4		 Homo sapiens Liver MALDI (DHB)
20171107_FIT4_DHBpos_p70_s50 - Rappez et al (2021) SpaceM reveals metabolic states of single cells
Resolution: 50μm, 70x70

Description

241.0017 [M+H-2H2O]+
PPM:17.3		 Homo sapiens esophagus DESI ()
LNTO22_1_9 - MTBLS385
Resolution: 75μm, 89x74

Description

259.0134 [M+H-H2O]+
PPM:11.7		 Homo sapiens esophagus DESI ()
LNTO22_1_9 - MTBLS385
Resolution: 75μm, 89x74

Description

241.0015 [M+H-2H2O]+
PPM:18.2		 Homo sapiens esophagus DESI ()
LNTO22_1_7 - MTBLS385
Resolution: 75μm, 69x54

Description

259.0132 [M+H-H2O]+
PPM:12.5		 Homo sapiens esophagus DESI ()
LNTO22_1_7 - MTBLS385
Resolution: 75μm, 69x54

Description


4-Hydroxycyclophosphamide is a primary activation metabolite of cyclophosphamide and of mafosfamide (an experimental drug) after they partially metabolized by cytochrome P450 (PMID: 12021633). Cyclophosphamide is a chemotherapeutic used to suppress the immune system and to treat several cancers including lymphoma, multiple myeloma, leukemia, ovarian cancer, breast cancer and small cell lung cancer. After cyclphosphamide is converted to 4-hydroxycyclophosphamide it is then partially tautomerized into aldophosphamide, which easily enters live cells whereupon it is partially detoxified into inactive carboxycyclophosphamide by the enzyme ALDH. 4-Hydroxycyclophosphamide is also an intermediate metabolite in the formation of phosphoramide mustard, the active metabolite, and acrolein, the metabolite responsible for much of the toxicity associated with cyclophosphamides (PMID: 7059981). 4-Hydroxycyclophosphamide is not cytotoxic at physiologic pH, readily diffuses into cells and spontaneously decomposes into the active phosphoramide mustard. In human liver microsomes, 4-Hydroxycyclophosphamide formation correlates with known phenotypic markers of CYP2B6 activity, specifically formation of (S)-2-ethyl-1,5-dimethyl-3,3-diphenyl pyrrolidine and hydroxybupropion. In addition, it is reported that the CYP2B6 genotype is not consistently related to 4-Hydroxycyclophosphamide formation in vitro or in vivo (PMID: 21976622). 4-Hydroxycyclophosphamide is only found in individuals who have consumed the drug cyclophosphamide. D000970 - Antineoplastic Agents > D018906 - Antineoplastic Agents, Alkylating > D009588 - Nitrogen Mustard Compounds D000970 - Antineoplastic Agents > D018906 - Antineoplastic Agents, Alkylating > D010752 - Phosphoramide Mustards