PERFOSFAMIDE

Investigational

Details

Stereochemistry	RACEMIC
Molecular Formula	C7H15Cl2N2O4P
Molecular Weight	293.085
Optical Activity	( + / - )
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=VPAWVRUHMJVRHU-VGDKGRGNSA-N

InChI=1S/C7H15Cl2N2O4P/c8-2-4-11(5-3-9)16(13)10-7(15-12)1-6-14-16/h7,12H,1-6H2,(H,10,13)/t7-,16-/m1/s1

HIDE SMILES / InChI

Molecular Formula	C7H15Cl2N2O4P
Molecular Weight	293.085
Charge	0
Count

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

Description
Sources: https://adisinsight.springer.com/drugs/800001660 | https://www.cancer.gov/publications/dictionaries/cancer-drug/def/perfosfamide | https://www.ncbi.nlm.nih.gov/pubmed/12060130 | https://www.ncbi.nlm.nih.gov/pubmed/6214268

Perfosfamide is the active metabolite of the nitrogen mustard cyclophosphamide with potent antineoplastic and immunosuppressive properties. Perfosfamide alkylates DNA, thereby inhibiting DNA replication and RNA and protein synthesis. The incubation of normal human marrow cells with perfosfamide has a toxic effect on granulocyte-macrophage progenitor cells that is dose as well as white blood cell concentration dependent. It is likely that this dependency of the perfosfamide stem cell effect is caused not only by the target white blood cell concentration but by the suspension’s total protein concentration. Autologous bone marrow transplantation with perfosfamide purging in patients with acute myeloid leukemia in second complete remission produced results similar to that reported with allogeneic bone marrow transplantation. Perfosfamide had been in phase III clinical trial for the treatment of acute myeloid leukemia. However, this development was discontinued.

Originator

Approval Year

PubMed

Title	Date	PubMed
The enzymatic activity of human aldehyde dehydrogenases 1A2 and 2 (ALDH1A2 and ALDH2) is detected by Aldefluor, inhibited by diethylaminobenzaldehyde and has significant effects on cell proliferation and drug resistance.	2012-01-05	22079344
Effects of exposure to a DNA damaging agent on the hypoxia inducible factors in organogenesis stage mouse limbs.	2012	23251655
Teratogen responsive signaling pathways in organogenesis stage mouse limbs.	2009-04	19429390
The gene expression profiles of medulloblastoma cell lines resistant to preactivated cyclophosphamide.	2008-05	18473730
4-hydroperoxy-cyclophosphamide mediates caspase-independent T-cell apoptosis involving oxidative stress-induced nuclear relocation of mitochondrial apoptogenic factors AIF and EndoG.	2008-02	18034189
Cyclophosphamide-induced apoptosis in COV434 human granulosa cells involves oxidative stress and glutathione depletion.	2007-07	17434952
Teratogen-induced activation of p53 in early postimplantation mouse embryos.	2007-01	17068108
RNAi-mediated knockdown of aldehyde dehydrogenase class-1A1 and class-3A1 is specific and reveals that each contributes equally to the resistance against 4-hydroperoxycyclophosphamide.	2007-01	16614850
Cyclophosphamide enhances TNF-alpha-induced apoptotic cell death in murine vascular endothelial cell.	2006-03-06	16488414
Interleukin-12 enhances the sensitivity of human osteosarcoma cells to 4-hydroperoxycyclophosphamide by a mechanism involving the Fas/Fas-ligand pathway.	2004-01-15	14760101
Effect of O6-benzylguanine on alkylating agent-induced toxicity and mutagenicity. In Chinese hamster ovary cells expressing wild-type and mutant O6-alkylguanine-DNA alkyltransferases.	2000-10-01	11034089
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
Immediate hypersensitivity reaction to cyclophosphamide.	1994-07	8024619
Intrathecal 4-hydroperoxycyclophosphamide: neurotoxicity, cerebrospinal fluid pharmacokinetics, and antitumor activity in a rabbit model of VX2 leptomeningeal carcinomatosis.	1992-11-15	1423260
Studies on the urotoxicity of oxazaphosphorine cytostatics and its prevention--I. Experimental studies on the urotoxicity of alkylating compounds.	1981-06	7308258

Patents

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:56:05 GMT 2025` Edited by `admin` on `Mon Mar 31 18:56:05 GMT 2025`
Record UNII	U880A4FUDA
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

PERGAMID

Preferred Name

English

PERFOSFAMIDE

Official Name

English

4-HC

Code

English

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

Common Name

English

NSC-181815

Code

English

perfosfamide [INN]

Common Name

English

2H-1,3,2-OXAZAPHOSPHORIN-2-AMINE, N,N-BIS(2-CHLOROETHYL)TETRAHYDRO-4-HYDROPEROXY-, 2-OXIDE, (2R,4R)-REL-

Common Name

English

PERFOSFAMIDE [MI]

Common Name

English

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

Common Name

English

4-HYDROPEROXYCYCLOPHOSPHAMIDE

Common Name

English

PERFOSFAMIDE [USAN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C697