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• Perfosfamide abstract "Perfosfamide, or 4-hydroperoxycyclophosphamide (trade name Pergamid).In the live cells perfosfamide (hydroperoxycyclophosphamide) rapidly metabolizes to its redox metabolite - 4-hydroxycyclophosphamide, which is also the main hepatic active metabolite of another anticancer drug, cyclophosphamide. The 4-hydroxycyclophosphamide, in turn, partially tautomerizes into aldophosphamide, with which it exists in chemical equilibrium. The active tautomer, aldophosphamide is then mostly metabolized into inactive carboxycyclophosphamide by the enzyme called ALDH (aldehyde dehydrogenase), but some of the aldophosphamide molecules are hydrolyzed by phosphatases (phosphoramidases), giving rise to the two directly cytotoxic metabolites - phosphoramide mustard and acrolein.Perfosfamide has several uses in oncology and hematology that are different from the use of its parent compound, cyclophosphamide. First, it is used to "purge" the collected bone marrow or hematopoietic stem cells off of lymphocytes and their predecessors while preserving myeloid predecessors (CD34-positive cells). It is done to decrease the likelihood for the recipient to suffer from severe GVHD (Graft Versus Host Disease), which results from donor lymphocytes attacking normal host cells and tissues. It works for that purpose because lymphocytes are more sensitive to it than myeloid predecessor cells (which are, then, preserved after such a treatment). But, while decreasing the likelihood for severe GVHD, this purging practice also decreases the needed GVL (Graft Versus Leukemia/Lymphoma) or GVT (Graft Versus Tumor) effect. It also decreases the chances for the "purged" graft to successfully engraft in the host. For successful engrafting, there must be some donor lymphocytes in the graft, to suppress the host ones, protect the donor ones and decrease the chances for the graft to be rejected by host's immunity. Thus, this "purging" donor stem cells off of lymphocytes is not often done nowadays, and is not recommended as a standard, routine transplant practice. But it may be still used where the risk of developing post-transplant GVHD is high (for example, for only partially - not completely - MHC compatible transplant).Perfosfamide is also sometimes used to "purge" patient's own (autologous) collected hematopoietic stem cells off of any malignant cells it may still contain at the time of harvesting. It works for that purpose because malignant cells are more sensitive to the DNA-alkylating and DNA-destroying effects of perfosfamide than normal ones, and have less DNA repair capabilities. Also malignant cells contain more phosphatase enzymes which convert perfosfamide to its active intracellular metabolites - 4-hydroxycyclophosphamide / aldophosphamide and then phosphoramide mustard and acrolein. This enables some degree of "selective antitumor purging" of collected patient's stem cells.Because most human cells, unlike hepatic cells, do not contain active enzymes that are needed for the conversion of cyclophosphamide to its main hepatic active metabolite - 4-hydroxycyclophosphamide - the parent compound, cyclophosphamide, cannot be used directly for the extracorporal anticancer cell treatment or "purging". That's why 4-hydroperoxycyclophosphamide is used for that's purpose. It effectively "bypasses" the needed hepatic metabolism step in the cyclophosphamide metabolic activation pathway. Next steps, which lead to the 4-hydroxycyclophosphamide and finally to the active alkylating agent phosphoramide mustard and acrolein - are done intracellularly (in the cell).".
• Perfosfamide atcPrefix "L01".
• Perfosfamide casNumber "39800-16-3".
• Perfosfamide chEBI "196991".
• Perfosfamide iupacName "(2S,4S)-N,N-Bis(2-chloroethyl)-4-hydroperoxy-2-oxo-1,3,2λ5-oxazaphosphinan-2-amine".
• Perfosfamide pubchem "38347".
• Perfosfamide thumbnail Perfosfamide_chemical_structure.png?width=300.
• Perfosfamide wikiPageID "30793795".
• Perfosfamide wikiPageRevisionID "599347068".
• Perfosfamide atcPrefix "L01".
• Perfosfamide c "7".
• Perfosfamide casNumber "39800".
• Perfosfamide chebi "196991".
• Perfosfamide chembl "61511".
• Perfosfamide chemicalFormula "C7H15Cl2N2O4P".
• Perfosfamide chemspiderid "35147".
• Perfosfamide cl "2".
• Perfosfamide dependencyLiability "none".
• Perfosfamide drugName "Perfosfamide".
• Perfosfamide emolecules "7498013".
• Perfosfamide h "15".
• Perfosfamide imagename "Perfosfamide".
• Perfosfamide iupacName "-N,N-Bis-4-hydroperoxy-2-oxo-1,3,2λ5-oxazaphosphinan-2-amine".
• Perfosfamide legalStatus "Rx-only".
• Perfosfamide molecularWeight "293.084762".
• Perfosfamide n "2".
• Perfosfamide o "4".
• Perfosfamide p "1".
• Perfosfamide pubchem "38347".
• Perfosfamide routesOfAdministration "extracorporal treatment of cellular masses; intravenously".
• Perfosfamide smiles "C1COPNCCCl".
• Perfosfamide stdinchi "1".
• Perfosfamide stdinchikey "VPAWVRUHMJVRHU-GYKQLYQFSA-N".
• Perfosfamide synonyms "Perfosfamide".
• Perfosfamide tradename "Pergamid".
• Perfosfamide verifiedfields "changed".
• Perfosfamide verifiedrevid "457654634".
• Perfosfamide subject Category:IARC_Group_1_carcinogens.
• Perfosfamide subject Category:Nitrogen_mustards.
• Perfosfamide subject Category:Organochlorides.
• Perfosfamide subject Category:Oxazaphosphinans.
• Perfosfamide subject Category:Phosphorodiamidates.
• Perfosfamide type Drug.
• Perfosfamide type FunctionalSubstance.
• Perfosfamide comment "Perfosfamide, or 4-hydroperoxycyclophosphamide (trade name Pergamid).In the live cells perfosfamide (hydroperoxycyclophosphamide) rapidly metabolizes to its redox metabolite - 4-hydroxycyclophosphamide, which is also the main hepatic active metabolite of another anticancer drug, cyclophosphamide. The 4-hydroxycyclophosphamide, in turn, partially tautomerizes into aldophosphamide, with which it exists in chemical equilibrium.".
• Perfosfamide label "4-Hidroperoxiciclofosfamida".
• Perfosfamide label "Perfosfamide".
• Perfosfamide label "Перфосфамид".
• Perfosfamide sameAs 4-Hidroperoxiciclofosfamida.
• Perfosfamide sameAs m.0gfgfcd.
• Perfosfamide sameAs Q4637151.
• Perfosfamide sameAs Q4637151.
• Perfosfamide wasDerivedFrom Perfosfamide?oldid=599347068.
• Perfosfamide depiction Perfosfamide_chemical_structure.png.
• Perfosfamide isPrimaryTopicOf Perfosfamide.
• Perfosfamide name "Perfosfamide".