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14-September-2008 11:27:25 - Cyclophosphamide Cyclophosphamide Systematic IUPAC name N,N-bis2-chloroethyl-1,3,2-oxazaphosphinan-2-amine 2-oxide Identifiers CAS number 50-18-0 ATC code L01AA01 PubChem 2907 DrugBank APRD00408 Chemical data Formula C7H15Cl2N2O2P Mol. mass 261.085 g/mol SMILES eMolecules PubChem Physical data Melt. point 2 °C 36 °F Pharmacokinetic data Bioavailability 75% oral Protein binding 60% Metabolism Hepatic Half life 3-12 hours Excretion Renal Therapeutic considerations Pregnancy cat. DAU DUS Legal status â„ž Prescription only Routes Oral, intravenous Cyclophosphamide the generic name for Cytoxan, Neosar, Revimmune, also known as cytophosphane, is a nitrogen mustard alkylating agent, from the oxazophorines group. It is used to treat various types of cancer and some autoimmune disorders. It is a prodrug; it is converted in the liver to active forms that have chemotherapeutic activity. Contents 1 Uses 2 Pharmacokinetics/Pharmacodynamics 3 Mode of action 4 Side-effects 5 History 6 References Uses The main use of cyclophosphamide is together with other chemotherapy agents in the treatment of lymphomas, some forms of leukemia and some solid tumors. It is a chemotherapy drug that works by slowing or stopping cell growth. It also works by decreasing the immune system's response to various diseases. Its use is becoming more common in autoimmune diseases where disease-modifying antirheumatic drugs DMARDs have been ineffective. Systemic lupus erythematosus SLE with severe lupus nephritis, for example, may respond to pulsed cyclophosphamide. In 2005, however, standard treatment for lupus nephritis changed to mycophenolic acid MMF from cyclophosphamide. Cyclophosphamide is also used to treat Minimal Change Disease and rheumatoid arthritis. It is still used for Wegener's granulomatosis, with trade name Cytoxan. For multiple sclerosis the trade name is Revimmune. Pharmacokinetics/Pharmacodynamics Cyclophosphamide is converted by mixed function oxidase enzymes in the liver to active metabolites. The main active metabolite is 4-hydroxycyclophosphamide. 4-hydroxycyclophosphamide exists in equilibrium with its tautomer, aldophosphamide. Most of the aldophosphamide is oxidised by the enzyme aldehyde dehydrogenase ALDH to make carboxyphosphamide. A small proportion of aldophosphamide is converted into phosphoramide mustard and acrolein. Acrolein is toxic to the bladder epithelium and can lead to hemorrhagic cystitis. This can be prevented through the use of aggressive hydration and/or Mesna. Recent clinical studies have shown that cyclophosphamide induce beneficial immunomodulatory effects in the context of adoptive immunotherapy. Although the mechanisms underlying these effects are not fully understood, several mechanisms have been suggested based on potential modulation of the host environment, includingcitation needed: Elimination of T regulatory cells CD4+CD25+ T cells in naive and tumor-bearing hosts Induction of T cell growth factors such as type I IFNs, and/or Enhanced grafting of adoptively transferred tumor-reactive effector T cells by the creation of an immunologic space niche. Thus, cyclophosphamide pre-conditioning of recipient hosts for donor T cells has been used to enhance immunity in naïve hosts, and to enhance adoptive T cell immunotherapy regimens as well as active vaccination strategies, inducing objective anti-tumor immunity. Mode of action The main effect of cyclophosphamide is due to its metabolite phosphoramide mustard. This metabolite is only formed in cells which have low levels of ALDH. Phosphoramide mustard forms DNA crosslinks between interstrand crosslinkages and within intrastrand crosslinkages DNA strands at guanine N-7 positions. This leads to cell death. Cyclophosphamide has relatively little typical chemotherapy toxicity as ALDHs are present in relatively large concentrations in bone marrow stem cells, liver and intestinal epithelium. ALDHs protect these actively proliferating tissues against toxic effects phosphoramide mustard and acrolein by converting aldophosphamide to carboxyphosphamide that does not give rise to the toxic metabolites phosphoramide mustard and acrolein. Side-effects Many people taking cyclophosphamide do not have serious side effects. Side-effects include chemotherapy-induced nausea and vomiting CINV, bone marrow suppression, stomach ache, diarrhea, darkening of the skin/nails, alopecia hair loss, changes in color and texture of the hair, and lethargy. Hemorrhagic cystitis is a frequent complication, but this is prevented by adequate fluid intake and Mesna sodium 2-mercaptoethane sulfonate. Mesna is a sulfhydryl donor and binds acrolein. Cyclophosphamide is itself carcinogenic, potentially causing transitional cell carcinoma of the bladder as a long-term complication. It can lower the body's ability to fight an infection. It can cause temporary or rarely permanent sterility. Although it is used to treat cancer, it may increase the risk of developing another form of cancer, sometimes months to years after treatment. Other serious side effects include: pink/bloody urine, unusual decrease in the amount of urine, mouth sores, unusual tiredness or weakness, joint pain, easy bruising/bleeding, stopping of menstrual periods, infertility existing wounds that are slow healing. History Cyclophosphamide and the related nitrogen mustard-derived alkylating agent ifosfamide were developed by Norbert Brock and ASTA now Baxter Oncology. Brock and his team synthesised and screened more than 1,000 candidate oxazaphosphorine compounds.1 They converted the base nitrogen mustard into a non-toxic transport form. This transport form was a pro-drug, subsequently actively transported into the cancer cells. Once in the cells, the pro-drug was enzymatically converted into the active, toxic form. The first clinical trials were published at the end of the 1950s.234 References ^ Brock N 1996. The history of the oxazaphosphorine cytostatics. Cancer 78 3: 542-7. doi:10.1002/SICI1097-01421996080178:3542::AID-CNCR233.0.CO;2-Y. PMID 8697402. ^ Wilmanns, H. 1958. title. Asta-Forschung und Therapie. ^ Gross, R., and Wulf, G. 1959. Klinische und experimentelle Erfahrungen mit zyk lischen und nichtzyklischen Phosphamidestern des N-Losl in der Chemotherapie von Tumoren. Strahlentherapie 41 Sonderband III: 361-367. ^ Brock N 1989. Oxazaphosphorine cytostatics: past-present-future. Seventh Cain Memorial Award lecture PDF. Cancer Res. 49 1: 1-7. PMID 2491747. v d e Chemotherapeutic agents/Antineoplastic agents L01 Purine+pyrimidine/ Ribonucleotides/ Deoxyribonucleotides Antimetabolites Folic acid Aminopterin, Methotrexate, Pemetrexed, Raltitrexed Purine Cladribine, Clofarabine, Fludarabine, Mercaptopurine, Pentostatin, Thioguanine Pyrimidine Cytarabine, Decitabine, Fluorouracil/Capecitabine, Floxuridine, Gemcitabine, Enocitabine, Sapacitabine DNA Alkylating/alkylating-like Nitrogen mustards Chlorambucil, Chlormethine, Cyclophosphamide, Ifosfamide, Melphalan, Bendamustine, Trofosfamide, Uramustine Nitrosoureas Carmustine, Fotemustine, Lomustine, Nimustine, Prednimustine, Ranimustine, Semustine, Streptozocin Platinum alkylating-like Carboplatin, Cisplatin, Nedaplatin, Oxaliplatin, Triplatin tetranitrate, Satraplatin Alkyl sulfonates Busulfan, Mannosulfan, Treosulfan Hydrazines Procarbazine Triazenes Dacarbazine, Temozolomide Aziridines Carboquone, ThioTEPA, Triaziquone, Triethylenemelamine Spindle poisons/mitotic inhibitors Taxanes Docetaxel, Larotaxel, Ortataxel, Paclitaxel, Tesetaxel · Vinca alkaloids Vinblastine, Vincristine, Vinflunine, Vindesine, Vinorelbine · Ixabepilone Cytotoxic/antitumor antibiotics Anthracyclines Aclarubicin, Daunorubicin, Doxorubicin, Epirubicin, Idarubicin, Amrubicin, Pirarubicin, Valrubicin, Zorubicin Anthracenediones Mitoxantrone, Pixantrone Streptomyces Actinomycin, Bleomycin, Mitomycin, Plicamycin · Hydroxyurea Topoisomerase inhibitors Camptotheca Camptothecin, Topotecan, Irinotecan, Rubitecan, Belotecan · Podophyllum Etoposide, Teniposide Other Altretamine · Amsacrine · Bexarotene · Estramustine · Irofulven · Trabectedin Cellular CI monoclonal antibodies Receptor tyrosine kinase Cetuximab, Panitumumab, Trastuzumab · CD20 Rituximab, Tositumomab · other Alemtuzumab, Bevacizumab, Edrecolomab, Gemtuzumab Tyrosine kinase inhibitors Axitinib · Bosutinib · Cediranib · Dasatinib · Erlotinib · Gefitinib · Imatinib · Lapatinib · Lestaurtinib · Nilotinib · Semaxanib · Sorafenib · Sunitinib · Vandetanib Cyclin-dependent kinase inhibitors Alvocidib · Seliciclib Other Fusion protein Aflibercept · Denileukin diftitox Other/ungrouped Photosensitizers Aminolevulinic acid/Methyl aminolevulinate · Efaproxiral · Porphyrin derivatives Porfimer sodium, Talaporfin, Temoporfin, Verteporfin Other Retinoids Alitretinoin, Tretinoin · Anagrelide · Arsenic trioxide · Asparaginase/Pegaspargase · Atrasentan · Bortezomib · Carmofur · Celecoxib · Demecolcine · Elesclomol · Elsamitrucin · Etoglucid · Lonidamine · Lucanthone · Masoprocol · Mitobronitol · Mitoguazone · Mitotane · Oblimersen · Omacetaxine · Sitimagene ceradenovec · Tegafur · Testolactone · Tiazofurine · Tipifarnib · Vorinostat Retrieved from http://en..org/wiki/Cyclophosphamide Categories: Chemotherapeutic agents | Organochlorides | Phosphorus compounds | Prodrugs | IARC Group 1 carcinogensHidden categories: All articles with statements | Articles with statements since February 2007 Views Article Discussion this page History Personal tools Log in / create account Navigation Main page Contents Featured content Current events Random article Search Go Search Interaction Community portal Recent changes Contact Donate to Help Toolbox What links here Related changes Upload file Special pages Printable version Permanent link Cite this page Languages Deutsch 日本語 Polski Português РуÑ?Ñ?кий SlovenÅ¡Ä?ina This page was last modified on 13 September 2008, at 00:03
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