mafosfamide

{{chembox

| Verifiedfields = changed

| verifiedrevid = 477499263

| ImageFile = Mafosfamide.svg

| ImageSize = 175

| ImageAlt = Skeletal formula

| ImageFile1 = Mafosfamide-3D-balls.png

| ImageSize1 = 230

| ImageAlt1 = Ball-and-stick model

| IUPACName=2-{(2-[bis(2-chloroethyl)amino]-2-oxido-1,3,2-oxazaphosphinan-4-yl}thio)ethanesulfonic acid

| OtherNames=2-{[2-[bis(2-chloroethyl)amino]-2-oxo-1-oxa-3-aza-2λ⁵-phosphacyclohex-4-yl}sulfanyl]ethanesulfonic acid

| Section1 = {{Chembox Identifiers

| InChI = 1/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-/m1/s1

| InChIKey = PBUUPFTVAPUWDE-AYLIAGHABO

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 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-/m1/s1

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = PBUUPFTVAPUWDE-AYLIAGHASA-N

| CASNo_Ref = {{cascite|changed|??}}

| CASNo = 88859-04-5

| PubChem = 104746

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 16736958

| SMILES = O=P1(N[C@@H](CCO1)SCCS(O)(=O)=O)N(CCCl)CCCl

| MeSHName = Mafosfamide

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 5970HH9923

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| Section2 = {{Chembox Properties

| Formula = C₉H₁₉Cl₂N₂O₅PS₂

| MolarMass = 401.269 g/mol

| Appearance =

| Density =

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| Section3 = {{Chembox Hazards

| MainHazards =

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Mafosfamide (INN) is an oxazaphosphorine (cyclophosphamide-like) alkylating agent under investigation as a chemotherapeutic. It is metabolized by cytochrome P450 into 4-hydroxycyclophosphamide, which is then converted into aldophosphamide, which, in turn yields the cytotoxic metabolites phosphoramide mustard and acrolein. Ludeman SM. The chemistry of the metabolites of cyclophosphamide. Curr Pharm Des. 1999 Aug;5(8):627-43. {{PMID|10469895}}

Several Phase I trials have been completed.{{cite web | url = http://www.clinicaltrials.gov/ct/show/NCT00062881?order=1 | title = Intrathecal Mafosfamide | accessdate = 2007-07-13 | date = August 21, 2006 | publisher = U.S. National Institutes of Health | work = ClinicalTrials.gov}} ClinicalTrials.gov Identifier NCT00062881.{{cite web | url =http://www.clinicaltrials.gov/ct/show/NCT00031928?order=2 | title = Mafosfamide in Treating Patients With Progressive or Refractory Meningeal Tumors | accessdate = 2007-07-13 | date = February 20, 2007 | publisher = U.S. National Institutes of Health | work = ClinicalTrials.gov}} ClinicalTrials.gov Identifier NCT00031928.