Mafosfamide

Mafosfamide: Mafosfamide

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

PubChem 104746

ChemSpider 16736958^Y

MeSH Mafosfamide

Jmol-3D images Image 1

SMILES

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

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

Properties

Molecular formula C₉H₁₉Cl₂N₂O₅PS₂

Molar mass 401.269 g/mol

Y (verify) (what is: Y/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)

Infobox references

Mafosfamide (INN) is an oxazaphosphorine (cyclophosphamide-like) alkylating agent under investigation as a chemotherapeutic. Several Phase I trials have been completed.^[1]^[2]

References

^ "Intrathecal Mafosfamide". ClinicalTrials.gov. U.S. National Institutes of Health. August 21, 2006. http://www.clinicaltrials.gov/ct/show/NCT00062881?order=1. 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. http://www.clinicaltrials.gov/ct/show/NCT00031928?order=2. Retrieved 2007-07-13. ClinicalTrials.gov Identifier NCT00031928.

v · d · eIntracellular chemotherapeutic agents/antineoplastic agents (L01)

SPs/MIs
(M phase)

Block microtubule assembly

Vinca alkaloids (Vinblastine, Vincristine, Vinflunine, Vindesine, Vinorelbine)

Block microtubule disassembly

Taxanes (Cabazitaxel, Docetaxel, Larotaxel, Ortataxel, Paclitaxel, Tesetaxel) • Epothilones (Ixabepilone)

DNA replication
inhibitor

DNA precursors/
antimetabolites
(S phase)

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)
thiopurine (Thioguanine, Mercaptopurine)

Pyrimidine

thymidylate synthase inhibitor (Fluorouracil, Capecitabine, Tegafur, Carmofur, Floxuridine)

DNA polymerase inhibitor (Cytarabine)

ribonucleotide reductase inhibitor (Gemcitabine)
hypomethylating agent (Azacitidine, Decitabine)

Deoxyribonucleotide

ribonucleotide reductase inhibitor (Hydroxycarbamide)

Topoisomerase inhibitors
(S phase)

I

Camptotheca (Camptothecin, Topotecan, Irinotecan, Rubitecan, Belotecan)

II

Podophyllum (Etoposide, Teniposide)

II+Intercalation

Anthracyclines (Aclarubicin, Daunorubicin, Doxorubicin, Epirubicin, Idarubicin, Amrubicin, Pirarubicin, Valrubicin, Zorubicin) • Anthracenediones (Mitoxantrone, Pixantrone)

Crosslinking of DNA
(CCNS)

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

Alkylating-like

Platinum (Carboplatin, Cisplatin, Nedaplatin, Oxaliplatin, Triplatin tetranitrate, Satraplatin)

Nonclassical

Hydrazines (Procarbazine) • Triazenes (Dacarbazine, Temozolomide) • Altretamine • Mitobronitol

Intercalation

Streptomyces (Actinomycin, Bleomycin, Mitomycin, Plicamycin)

Photosensitizers/PDT
Aminolevulinic acid/Methyl aminolevulinate • Efaproxiral • Porphyrin derivatives (Porfimer sodium, Talaporfin, Temoporfin, Verteporfin)

Other

Enzyme inhibitors

FI (Tipifarnib) • CDK inhibitors (Alvocidib, Seliciclib) • PrI (Bortezomib) • PhI (Anagrelide) • IMPDI (Tiazofurine) • LI (Masoprocol) • PARP inhibitor (Olaparib) • HDAC (Vorinostat, Romidepsin)

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 • HAMLET (human alpha-lactalbumin made lethal to tumor cells) • Lucanthone • Mitoguazone • Mitotane • Oblimersen • Omacetaxine mepesuccinate • mTOR inhibitors (Everolimus, Temsirolimus)

M: NEO

tsoc, mrkr

tumr, epon, para

drug (L1i/1e/V03)

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Mafosfamide

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Mafosfamide

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
PubChem	104746
ChemSpider	16736958^Y
MeSH	Mafosfamide
Jmol-3D images	Image 1
SMILES O=P1(N[C@@H](CCO1)SCCS(O)(=O)=O)N(CCCl)CCCl
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
Properties
Molecular formula	C₉H₁₉Cl₂N₂O₅PS₂
Molar mass	401.269 g/mol
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

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Mafosfamide

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