MAFOSFAMIDE

Details

Stereochemistry	RACEMIC
Molecular Formula	C9H19Cl2N2O5PS2
Molecular Weight	401.267
Optical Activity	( + / - )
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=PBUUPFTVAPUWDE-UGZDLDLSSA-N

InChI=1S/C9H19Cl2N2O5PS2/c10-2-4-13(5-3-11)19(14)12-9(1-6-18-19)20-7-8-21(15,16)17/h9H,1-8H2,(H,12,14)(H,15,16,17)/t9-,19-/m0/s1

HIDE SMILES / InChI

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 155 Target ID: map04210 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18289623	Activator 1430
DNA 278 Target ID: CHEMBL2311221 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22753738	Inhibitor 8297

PubMed

Title	Date	PubMed
Phase I study of cyclohexylamine and lysine salt of mafosfamide.	1986	3512115
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 May 17	8662658

Patents

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:31:34 GMT 2023` Edited by `admin` on `Fri Dec 15 15:31:34 GMT 2023`
Record UNII	5970HH9923
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

MAFOSFAMIDE

Official Name

English

MAFOSFAMIDE [MART.]

Common Name

English

(±)-2-((2-(BIS(2-CHLOROETHYL)AMINO)TETRAHYDRO-2H-1,3,2-OXAZAPHOSPHORIN-4-YL)THIO)ETHANESULFONIC ACID P-CIS-OXIDE

Common Name

English

mafosfamide [INN]

Common Name

English

Mafosfamide [WHO-DD]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C697