An alkylating agent and active metabolite of cyclophosphamide
Related Products
Isomer(s)
29887Palifosfamide
Pro-drug Form(s)
13849Cyclophosphamide (hydrate)
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Phosphoramide Mustard (cyclohexylammonium salt)

Item No. 34078

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N,N-bis(2-chloroethyl)-phosphorodiamidic acid, compd. with cyclohexanamine
CAS Number
1566-15-0
Synonyms
  • NSC 69945
  • PMC
Molecular Formula
C4H11Cl2N2O2P • C6H13N
Formula Weight
320.2
Purity
≥95%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
Chloroform: slightly solubleMethanol: slightly soluble
SMILES
O=P(N)(N(CCCl)CCCl)O.NC1CCCCC1
InChi Code
InChI=1S/C6H13N.C4H11Cl2N2O2P/c7-6-4-2-1-3-5-6;5-1-3-8(4-2-6)11(7,9)10/h6H,1-5,7H2;1-4H2,(H3,7,9,10)
InChi Key
BGTIPRUDEMNRIP-UHFFFAOYSA-N
Origin
Synthetic
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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Certificates of Analysis & Batch Specific Data

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    1 mg

    $121

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    5 mg

    $388

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    Product Description

    Phosphoramide mustard is an alkylating agent and active metabolite of cyclophosphamide (Item No. 13849).1 It is formed from cyclophosphamide via the ring-opened tautomer of the cytochrome P450 (CYP) isoform-formed intermediate 4-hydroxycyclophosphamide.2 Phosphoramide mustard induces DNA crosslinking, alkylates guanine in DNA, and increases the production of covalent DNA-protein conjugates in, and is cytotoxic to, HT-1080 human fibrosarcoma cells in a concentration-dependent manner. It is toxic to adult mice and teratogenic to embryos when administered to pregnant dams at a dose of 154 mg/kg on day 11 of gestation.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Groehler, A., IV, Villalta, P.W., Campbell, C., et al. Covalent DNA-protein cross-linking by phosphoramide mustard and nornitrogen mustard in human cells. Chem. Res. Toxicol. 29(2), 190-202 (2016).

    2. Huitema, A.D., Mathôt, R.A., Tibben, M.M., et al. A mechanism-based pharmacokinetic model for the cytochrome P450 drug-drug interaction between cyclophosphamide and thioTEPA and the autoinduction of cyclophosphamide. J. Pharmacokinetic. Pharmacodyn. 28(3), 211-230 (2001).

    3. Gibson, J.E., and Becker, B.A. Teratogenicity of structural truncates of cyclophosphamide in mice. Teratology 4(2), 141-150 (1971).