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SMB01361

Sigma-Aldrich

Phosphoramide mustard cyclohexylamine

≥95% (HPLC)

Synonym(s):

N,N-Bis(2-Chloroethyl)phosphorodiamidic acid, cyclohexylamine, Friedman acid, cyclohexylamine, PAM cyclohexylamine, PM cyclohexylamine, PMC, Phosphamide mustard, Cyclohexylamine, Phosphorodiamidic mustard, Cyclohexylamine

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About This Item

Linear Formula:
C4H11Cl2N2O2P · C6H13N
CAS Number:
1566-15-0
MDL number:
MFCD00866429
UNSPSC Code:
12352209
NACRES:
NA.22

Quality Level

200

assay

≥95% (HPLC)

form

solid

storage temp.

-10 to -25°C

SMILES string

ClCCN(P(N)(O)=O)CCCl.NC1CCCCC1

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

General description

Phosphoramide mustard cyclohexanamine, a potent cytotoxic metabolite derived from the anticancer drug cyclophosphamide, acts as a remarkable alkylating agent. It is generated from cyclophosphamide through the ring-opened tautomer of the cytochrome P450 (CYP) isoform-formed intermediate 4-hydroxycyclophosphamide. This metabolite exerts its cytotoxic effects by inducing DNA crosslinking, guanine alkylation, and the formation of DNA-protein conjugates. In a concentration-dependent manner, it specifically targets HT-1080 human fibrosarcoma cells, triggering DNA damage. An essential contributor to Cyclophosphamide′s anticancer activity, Phosphoramide Mustard Cyclohexanamine exhibits great promise for cancer research, as it has the potential to induce DNA adduct formation and activate the ovarian DNA repair response in granulosa cells.

Application

Used in the development of chemotherapeutic drugs that are known to treat cancer.

Biochem/physiol Actions

Phosphoramide mustard cyclohexanamine induces cytotoxicity by forming cross-linked DNA adducts that hinder DNA strand separation during replication. This compound destroys rapidly dividing cells and leads to DNA damage. In a study with rat ovarian granulosa cells (SIGCs), it reduced cell viability and increased DNA damage response (DDR) gene expression and protein levels. In animal models, it exhibited significant anticancer activity by inhibiting tumor growth. These findings highlight the potential of Phosphoramide mustard cyclohexanamine in cancer research

Features and Benefits

  • High quality compound suitable for multiple research applications
  • Compatible with a wide variety of chromatographic and spectrometry techniques

Other Notes

For additional information on our range of Biochemicals, please complete this form.
This product is intended for research purposes only, and it is not meant for human consumption.

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Kendra L Clark et al.
Biology of reproduction, 102(1), 248-260 (2019-08-23)
Ataxia-telangiectasia-mutated (ATM) protein recognizes and repairs DNA double strand breaks through activation of cell cycle checkpoints and DNA repair proteins. Atm gene mutations increase female reproductive cancer risk. Phosphoramide mustard (PM) induces ovarian DNA damage and destroys primordial follicles, and
S A M Gernaat et al.
Scientific reports, 11(1), 2707-2707 (2021-02-03)
Cyclophosphamide (CPA) dosing by body surface area (BSA, m2) has been questioned as a predictor for individual drug exposure. This study investigated phosphoramide mustard-hemoglobin (PAM-Hb, pmol g-1 Hb) as a biomarker of CPA exposure in 135 female breast cancer patients
Julia Delahousse et al.
Journal for immunotherapy of cancer, 8(2) (2020-08-14)
Oxazaphosphorines (cyclophosphamide (CPA), ifosfamide (IFO)) are major alkylating agents of polychemotherapy protocols but limiting their toxicity and increasing their efficacy could be of major interest. Oxazaphosphorines are prodrugs that require an activation by cytochrome P450 (CYP). CPA is mainly metabolized

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