Mafosfamide

Mafosfamide
Names


IUPAC name 2-{(2-[bis(2-chloroethyl)amino]-2-oxido-1,3,2-oxazaphosphinan-4-yl}thio)ethanesulfonic acid
Other names 2-{[2-[bis(2-chloroethyl)amino]-2-oxo-1-oxa-3-aza-2λ⁵-phosphacyclohex-4-yl}sulfanyl]ethanesulfonic acid
Identifiers
CAS Number	88859-04-5^N
3D model (Jmol)	Interactive image
ChemSpider	16736958^Y
MeSH	Mafosfamide
PubChem	104746
UNII	5970HH9923^Y
InChI 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-/m1/s1^Y Key: PBUUPFTVAPUWDE-AYLIAGHASA-N^Y 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 Key: PBUUPFTVAPUWDE-AYLIAGHABO
SMILES O=P1(N[C@@H](CCO1)SCCS(O)(=O)=O)N(CCCl)CCCl
Properties
Chemical formula	C₉H₁₉Cl₂N₂O₅PS₂
Molar mass	401.269 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is ^YN ?)
Infobox references

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.^[1]

Several Phase I trials have been completed.^[2]^[3]

References

↑ Ludeman SM. The chemistry of the metabolites of cyclophosphamide. Curr Pharm Des. 1999 Aug;5(8):627-43. PMID 10469895
↑ "Intrathecal Mafosfamide". ClinicalTrials.gov. U.S. National Institutes of Health. August 21, 2006. Retrieved 2007-07-13. ClinicalTrials.gov Identifier NCT00062881.
↑ "Mafosfamide in Treating Patients With Progressive or Refractory Meningeal Tumors". ClinicalTrials.gov. U.S. National Institutes of Health. February 20, 2007. Retrieved 2007-07-13. ClinicalTrials.gov Identifier NCT00031928.

Block microtubule assembly	Vinca alkaloids (Vinblastine^# Vincristine^# Vinflunine^§ Vindesine Vinorelbine)

Block microtubule disassembly	Taxanes (Cabazitaxel Docetaxel^# Larotaxel Ortataxel^† Paclitaxel^# Tesetaxel) Epothilones (Ixabepilone)

Folic acid	Dihydrofolate reductase inhibitor (Aminopterin Methotrexate^# Pemetrexed Pralatrexate) Thymidylate synthase inhibitor (Raltitrexed Pemetrexed)

Purine	Adenosine deaminase inhibitor (Pentostatin) Halogenated/ribonucleotide reductase inhibitors (Cladribine Clofarabine Fludarabine) Nelarabine Thiopurine (Thioguanine^# Mercaptopurine^#)

Pyrimidine	Thymidylate synthase inhibitor (Fluorouracil^# Capecitabine Tegafur (+gimeracil/oteracil) Carmofur Floxuridine) DNA polymerase inhibitor (Cytarabine^#) Ribonucleotide reductase inhibitor (Gemcitabine) Hypomethylating agent (Azacitidine Decitabine)

Deoxyribonucleotide	Ribonucleotide reductase inhibitor (Hydroxycarbamide)

I	Camptotheca (Camptothecin Cositecan^† Belotecan Gimatecan Exatecan Irinotecan Lurtotecan^‡ Silatecan^§ Topotecan Rubitecan^‡)

II	Podophyllum (Etoposide^# Teniposide)

II+Intercalation	Anthracyclines (Aclarubicin Daunorubicin^# Doxorubicin^# Epirubicin Idarubicin Amrubicin^† Pirarubicin Valrubicin Zorubicin) Anthracenediones (Mitoxantrone Pixantrone)

Alkylating	Nitrogen mustards: Mechlorethamine Cyclophosphamide^# (Ifosfamide Trofosfamide) Chlorambucil^# (Melphalan Prednimustine) Bendamustine Uramustine Estramustine Nitrosoureas: Carmustine Lomustine (Semustine) Fotemustine Nimustine Ranimustine Streptozocin Alkyl sulfonates: Busulfan (Mannosulfan Treosulfan) Aziridines: Carboquone ThioTEPA Triaziquone Triethylenemelamine

Platinum-based	Carboplatin Cisplatin Dicycloplatin Nedaplatin Oxaliplatin Satraplatin

Nonclassical	Hydrazines (Procarbazine^#) Triazenes (Dacarbazine^# Temozolomide) Altretamine Mitobronitol Pipobroman

Intercalation	Streptomyces (Actinomycin^# Bleomycin^# Mitomycin Plicamycin)

Other

Enzyme inhibitors	FI (Tipifarnib^§) CDK inhibitors (Alvocidib^† Seliciclib^† Palbociclib) PrI Bortezomib Carfilzomib Ixazomib PhI (Anagrelide) IMPDI (Tiazofurin^§) LI (Masoprocol) PARP inhibitor (Olaparib) HDAC (Belinostat Panobinostat Romidepsin Vorinostat) PIKI (Idelalisib)

Receptor antagonists	ERA (Atrasentan) Retinoid X receptor (Bexarotene) Sex steroid (Testolactone)

Other/ungrouped	Amsacrine Trabectedin Retinoids (Alitretinoin Tretinoin) Arsenic trioxide Asparagine depleters (Asparaginase^#/Pegaspargase) Celecoxib Demecolcine Elesclomol^§ Elsamitrucin Etoglucid Lonidamine Lucanthone Mitoguazone Mitotane Oblimersen^† Omacetaxine mepesuccinate Eribulin

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