MAFOSFAMIDE LYSINE

Investigational

Details

Stereochemistry	RACEMIC
Molecular Formula	C9H19Cl2N2O5PS2.C6H14N2O2
Molecular Weight	547.455
Optical Activity	UNSPECIFIED
Defined Stereocenters	3 / 3
E/Z Centers	0
Charge	0
Stereo Comments	C9 H19 Cl2 N2 O5 P S2

SHOW SMILES / InChI

Structure Search

SMILES

NCCCC[C@H](N)C(O)=O.OS(=O)(=O)CCS[C@H]1CCO[P@@](=O)(N1)N(CCCl)CCCl

InChI

InChIKey=DYLRFXGKCIFZAH-NNDOHRJVSA-N

InChI=1S/C9H19Cl2N2O5PS2.C6H14N2O2/c10-2-4-13(5-3-11)19(14)12-9(1-6-18-19)20-7-8-21(15,16)17;7-4-2-1-3-5(8)6(9)10/h9H,1-8H2,(H,12,14)(H,15,16,17);5H,1-4,7-8H2,(H,9,10)/t9-,19-;5-/m00/s1

HIDE SMILES / InChI

Molecular Formula	C6H14N2O2
Molecular Weight	146.1876
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

Molecular Formula	C9H19Cl2N2O5PS2
Molecular Weight	401.267
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.cancer.gov/publications/dictionaries/cancer-drug/def/mafosfamide | https://www.ncbi.nlm.nih.gov/pubmed/22753738 | https://adisinsight.springer.com/drugs/800000886

Mafosfamide is a synthetic oxazaphosphorine derivative with antineoplastic properties. Mafosfamide alkylates DNA, forming DNA cross-links and inhibiting DNA synthesis. The effects of mafosfamide on various types of cancer cells were determined during preclinical investigations and clinical trials. Its development has been discontinued.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Apoptosis 156 Target ID: map04210 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18289623	Activator 1447
DNA 282 Target ID: CHEMBL2311221 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22753738	Inhibitor 8504

PubMed

Title	Date	PubMed
The γH2AX assay for genotoxic and nongenotoxic agents: comparison of H2AX phosphorylation with cell death response.	2014-07	24743697
Phase I clinical trial of mafosfamide in infants and children aged 3 years or younger with newly diagnosed embryonal tumors: a pediatric brain tumor consortium study (PBTC-001).	2005-01-20	15659498
Cyclophosphamide induces caspase 9-dependent apoptosis in 9L tumor cells.	2001-12	11723234
Protection of mammalian cells against chemotherapeutic agents thiotepa, 1,3-N,N'-bis(2-chloroethyl)-N-nitrosourea, and mafosfamide using the DNA base excision repair genes Fpg and alpha-hOgg1: implications for protective gene therapy applications.	2001-03	11181913
De novo expression of transfected human class 1 aldehyde dehydrogenase (ALDH) causes resistance to oxazaphosphorine anti-cancer alkylating agents in hamster V79 cell lines. Elevated class 1 ALDH activity is closely correlated with reduction in DNA interstrand cross-linking and lethality.	1996-05-17	8662658
Phase I study of cyclohexylamine and lysine salt of mafosfamide.	1986	3512115
Cause and prevention of mafosfamide-induced venous pain.	1986	3108189

Patents

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:07:24 GMT 2025` Edited by `admin` on `Mon Mar 31 18:07:24 GMT 2025`
Record UNII	HAC3DQ8PMS
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

MAFOSFAMIDE LYSINE

Common Name

English

CIS-2-((2-(BIS(2-CHLOROETHYL)AMINO)TETRAHYDRO-2H-1,3,2-OXAZAPHOSPHORIN-4-YL)THIO)ETHANE SULFONATE P-OXIDE L-LYSINE

Preferred Name

English

NSC-626122

Code

English

Code System Code Type Description

CAS

98845-64-8