WARNING: This product is for research use only, not for human or veterinary use.
Hodoodo CAT#: H100190
CAS#: 6055-19-2 (hydrate)
Description: Cyclophosphamide, also known as cytophosphane among other, is used as chemotherapy and to suppress the immune system. As chemotherapy it is used to treat lymphoma, multiple myeloma, leukemia, ovarian cancer, breast cancer, small cell lung cancer, neuroblastoma, and sarcoma. As an immune suppressor it is used in nephrotic syndrome and following organ transplant. It is taken by mouth or injection into a vein. The main effect of cyclophosphamide is due to its metabolite phosphoramide mustard. This metabolite is only formed in cells that have low levels of ALDH. Phosphoramide mustard forms DNA crosslinks both between and within DNA strands at guanine N-7 positions (known as interstrand and intrastrand crosslinkages, respectively). This is irreversible and leads to cell apoptosis.
Hodoodo Cat#: H100190
Name: Cyclophosphamide monohydrate
CAS#: 6055-19-2 (hydrate)
Chemical Formula: C7H15Cl2N2O2P
Exact Mass: 0.00
Molecular Weight: 279.101
Elemental Analysis: C, 32.20; H, 5.79; Cl, 27.16; N, 10.73; O, 12.26; P, 11.86
Related CAS #: 6055-19-2 (hydrate) 50-18-0
Synonym: Ciclofosfamida; Ciclofosfamide; Cyclophosphamide monohydrate.
IUPAC/Chemical Name: 2-[bis(2-chloroethyl)amino]tetrahydro-2H-1,3,2-oxazaphosphorine 2-oxide monohydrate
InChi Key: PWOQRKCAHTVFLB-UHFFFAOYSA-N
InChi Code: InChI=1S/C7H15Cl2N2O2P.H2O/c8-2-5-11(6-3-9)14(12)10-4-1-7-13-14;/h1-7H2,(H,10,12);1H2
SMILES Code: ClCCN(P1(OCCCN1)=O)CCCl.[H]O[H]
Appearance: Solid powder
Purity: >98% (or refer to the Certificate of Analysis)
Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility: Soluble in DMSO, not in water
Shelf Life: >2 years if stored properly
Drug Formulation: This drug may be formulated in DMSO
Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code: 2934.99.9001
More Info: Related CAS# 6055-19-2 (Cyclophosphamide hydrate); 50-18-0 (Cyclophosphamide anhydrous)
| Biological target: | Cyclophosphamide (NSC-26271) Monohydrate is a nitrogen mustard alkylating agent, it attaches the alkyl group to the guanine base of DNA, shown to crosslink DNA, causing strand breakage and inducing mutations. |
| In vitro activity: | It is established that low-dose CY not only decreases cell number but leads to decreased functionality of T(REGs). CY treatment enhances apoptosis and decreases homeostatic proliferation of these cells. Expression of GITR and FoxP3, which are involved in the suppressive activity of T(REGs), is down-regulated after CY administration, though the level of expression varies depending on the time studied. Reference: Blood. 2005 Apr 1;105(7):2862-8. https://linkinghub.elsevier.com/retrieve/pii/S0006-4971(20)45685-X |
| In vivo activity: | Cyclophosphamide (CTX) is often used to create a "window" for more effective therapeutic tumor vaccination. According to a commonly applied protocol, 2 mg CTX was injected intraperitoneally to mice with small (2 to 3 mm diameter) or large (5 to 7 mm, and in one experiment 8 to 10 mm diameter) subcutaneously growing tumors from the SW1 clone of the K1735 melanoma, euthanized the mice 4 days later and studied the composition of lymphoid cells by flow cytometry in both spleens and tumors. Administration of CTX increased the percentage of CD3, CD4, and CD8 cells with the increase in tumors being significantly greater than in spleens, and it also increased the percentage of B cells in spleens and tumors. Furthermore, CTX dramatically increased the frequency of tumor-infiltrating CD4 and CD8 cells containing interferon gamma, of cells expressing NK1.1, and of cells expressing the dendritic cell markers CD11c, CD80, and CD86, with the greatest increases seen among tumor-infiltrating lymphoid cells (TIL) from mice with small tumors. Although CTX decreased the percentage of TIL that expressed CD4 or CD8 together with CD25 and FoxP3 and were therefore considered to be regulatory T cells, it increased the frequency of TIL that stained for Gr1/CD11b, a marker for myeloid-derived suppressor cells. It was concluded that the administration of CTX can favorably impact several cell populations that are involved in tumor rejection. However, since CTX has a limited effect on TIL from tumors larger than a few millimeter in diameter and in view of an increased percentage of myeloid-derived suppressor cells among TIL from mice given CTX there is a need for more effective ways to improve tumor vaccination. Reference: J Immunother. 2010 Jan;33(1):53-9. https://www.ncbi.nlm.nih.gov/pmc/articles/pmid/19952956/ |
| Solvent | Max Conc. mg/mL | Max Conc. mM | |
|---|---|---|---|
| Solubility | |||
| Ethanol | 56.0 | 200.64 | |
| Water | 7.0 | 25.08 |
The following data is based on the product molecular weight 279.10 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass | 1 mg | 5 mg | 10 mg |
|---|---|---|---|
| 1 mM | 1.15 mL | 5.76 mL | 11.51 mL |
| 5 mM | 0.23 mL | 1.15 mL | 2.3 mL |
| 10 mM | 0.12 mL | 0.58 mL | 1.15 mL |
| 50 mM | 0.02 mL | 0.12 mL | 0.23 mL |
| Formulation protocol: | |
| In vitro protocol: | 1. Lutsiak ME, Semnani RT, De Pascalis R, Kashmiri SV, Schlom J, Sabzevari H. Inhibition of CD4(+)25+ T regulatory cell function implicated in enhanced immune response by low-dose cyclophosphamide. Blood. 2005 Apr 1;105(7):2862-8. doi: 10.1182/blood-2004-06-2410. Epub 2004 Dec 9. PMID: 15591121. |
| In vivo protocol: | 1. Liu P, Jaffar J, Hellstrom I, Hellstrom KE. Administration of cyclophosphamide changes the immune profile of tumor-bearing mice. J Immunother. 2010 Jan;33(1):53-9. doi: 10.1097/CJI.0b013e3181b56af4. PMID: 19952956; PMCID: PMC2811714. |
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