Cystemustine | CAS#79955-36-5 | biochemical

MedKoo Cat#: 146246 | Name: Cystemustine

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Cystemustine is a chloroethyl nitrosourea (CENU) compound used primarily as an experimental chemotherapeutic agent for treating malignant brain tumors, particularly gliomas. It works by alkylating DNA, forming interstrand cross-links that interfere with DNA replication and transcription, ultimately leading to cancer cell death. Cystemustine's lipophilic nature allows it to cross the blood-brain barrier, making it effective for targeting central nervous system malignancies.

Chemical Structure

Cystemustine

CAS#79955-36-5

Theoretical Analysis

MedKoo Cat#: 146246

Name: Cystemustine

CAS#: 79955-36-5

Chemical Formula: C6H12ClN3O4S

Exact Mass: 257.0237

Molecular Weight: 257.69

Elemental Analysis: C, 27.97; H, 4.69; Cl, 13.76; N, 16.31; O, 24.83; S, 12.44

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.

Bulk Inquiry

Related CAS #

No Data

Synonym

Cystemustine;

IUPAC/Chemical Name

1-(2-chloroethyl)-3-(2-(methylsulfonyl)ethyl)-1-nitrosourea

InChi Key

IUOVOJHLRFQQNS-UHFFFAOYSA-N

InChi Code

1S/C6H12ClN3O4S/c1-15(13,14)5-3-8-6(11)10(9-12)4-2-7/h2-5H2,1H3,(H,8,11)

SMILES Code

CS(=O)(=O)CCNC(=O)N(CCCl)N=O

Appearance

To be determined

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

To be determined

Shelf Life

>2 years if stored properly

Drug Formulation

To be determined

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

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 257.69 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

1: Durando X, Thivat E, Roché H, Bay JO, Lemaire JJ, Verrelle P, Chazal J, Curé H, Chollet P. Cystemustine in recurrent high grade glioma. J Neurooncol. 2006 Aug;79(1):33-7. doi: 10.1007/s11060-005-9096-7. Epub 2006 Mar 31. Erratum in: J Neurooncol. 2006 Aug;79(1):39. Lentz, MA [removed]. PMID: 16575534. 2: Palmer B. Cystemustine INSERM. IDrugs. 1998 May;1(1):129-35. PMID: 18465517. 3: Demidem A, Morvan D, Papon J, De Latour M, Madelmont JC. Cystemustine induces redifferentiation of primary tumors and confers protection against secondary tumor growth in a melanoma murine model. Cancer Res. 2001 Mar 1;61(5):2294-300. PMID: 11280801. 4: Cellarier E, Terret C, Labarre P, Ouabdesselam R, Curé H, Marchenay C, Maurizis JC, Madelmont JC, Cholle P, Armand JP. Pharmacokinetic study of cystemustine, administered on a weekly schedule in cancer patients. Ann Oncol. 2002 May;13(5):760-9. doi: 10.1093/annonc/mdf098. PMID: 12075746. 5: Martineau-Pivoteau N, Levi F, Rolhion C, Kwiatkowski F, Lemaigre G, Filipski E, Chollet P. Circadian rhythm in toxic effects of cystemustine in mice: relevance for chronomodulated delivery. Int J Cancer. 1996 Nov 27;68(5):669-74. doi: 10.1002/(SICI)1097-0215(19961127)68:5<669::AID-IJC18>3.0.CO;2-X. PMID: 8938151. 6: Thivat E, Durando X, D'Incan M, Cure H, Mouret-Reynier MA, Madelmont JC, Souteyrand P, Chollet P. Second-line chemotherapy of disseminated malignant melanoma with cystemustine at 60 mg/m2: a phase II trial. Anticancer Drugs. 2005 Oct;16(9):1003-7. doi: 10.1097/01.cad.0000176506.71304.ca. PMID: 16162977. 7: Thivat E, Farges MC, Bacin F, D'Incan M, Mouret-Reynier MA, Cellarier E, Madelmont JC, Vasson MP, Chollet P, Durando X. Phase II trial of the association of a methionine-free diet with cystemustine therapy in melanoma and glioma. Anticancer Res. 2009 Dec;29(12):5235-40. PMID: 20044642. 8: Samuels SE, Knowles AL, Tilignac T, Debiton E, Madelmont JC, Attaix D. Protein metabolism in the small intestine during cancer cachexia and chemotherapy in mice. Cancer Res. 2000 Sep 1;60(17):4968-74. PMID: 10987314. 9: Cussac C, Rapp M, Mounetou E, Madelmont JC, Maurizis JC, Godeneche D, Dupuy JM, Sauzieres J, Baudry JP, Veyre A. Enhancement by O6-benzyl-N-acetylguanosine derivatives of chloroethylnitrosourea antitumor action in chloroethylnitrosourea-resistant human malignant melanocytes. J Pharmacol Exp Ther. 1994 Dec;271(3):1353-8. PMID: 7996446. 10: Roche H, Cure H, Adenis A, Fargeot P, Terret C, Lentz MA, Madelmont JC, Fumoleau P, Hanausk A, Chollet P. Phase II trial of cystemustine, a new nitrosourea, as treatment of high-grade brain tumors in adults. J Neurooncol. 2000 Sep;49(2):141-5. doi: 10.1023/a:1026524825573. PMID: 11206009. 11: Buchdahl C, Rolhion C, Glasser AL, Debiton E, Mounetou E, Madelmont JC, Laval F. Melanoma-cell toxicity of cystemustine combined with O6-benzyl-N2-acetylguanosine. Melanoma Res. 1998 Apr;8(2):123-30. doi: 10.1097/00008390-199804000-00004. PMID: 9610864. 12: Rapp M, Maurizis JC, Papon J, Labarre P, Wu TD, Croisy A, Guerquin-Kern JL, Madelmont JC, Mounetou E. A new O6-alkylguanine-DNA alkyltransferase inhibitor associated with a nitrosourea (cystemustine) validates a strategy of melanoma- targeted therapy in murine B16 and human-resistant M4Beu melanoma xenograft models. J Pharmacol Exp Ther. 2008 Jul;326(1):171-7. doi: 10.1124/jpet.108.137737. Epub 2008 Apr 14. PMID: 18411412. 13: Morvan D, Demidem A, Papon J, De Latour M, Madelmont JC. Melanoma tumors acquire a new phospholipid metabolism phenotype under cystemustine as revealed by high-resolution magic angle spinning proton nuclear magnetic resonance spectroscopy of intact tumor samples. Cancer Res. 2002 Mar 15;62(6):1890-7. PMID: 11912170. 14: Debiton E, Cussac-Buchdhal C, Mounetou E, Rapp M, Dupuy JM, Maurizis JC, Veyre A, Madelmont JC. Enhancement by O6-benzyl-N2-acetylguanosine of N'-[2-chloroethyl]-N-[2-(methylsulphonyl)ethyl]-N'-nitrosourea therapeutic index on nude mice bearing resistant human melanoma. Br J Cancer. 1997;76(9):1157-62. doi: 10.1038/bjc.1997.527. PMID: 9365163; PMCID: PMC2228110. 15: Durando X, Thivat E, Farges MC, Cellarier E, D'Incan M, Demidem A, Vasson MP, Barthomeuf C, Chollet P. Optimal methionine-free diet duration for nitrourea treatment: a Phase I clinical trial. Nutr Cancer. 2008;60(1):23-30. doi: 10.1080/01635580701525877. PMID: 18444132. 16: Merle P, Morvan D, Caillaud D, Demidem A. Chemotherapy-induced bystander effect in response to several chloroethylnitrosoureas: an origin independent of DNA damage? Anticancer Res. 2008 Jan-Feb;28(1A):21-7. PMID: 18383820. 17: Cure H, Souteyrand P, Ouabdesselam R, Roche H, Ravaud A, D'incan M, Viens P, Fargeot P, Lentz MA, Fumoleau P, Hanauske A, Chollet P. Results of a phase II trial with cystemustine at 90 mg/m(2) as a first- or second-line treatment in advanced malignant melanoma: a trial of the EORTC Clinical Studies Group. Melanoma Res. 1999 Dec;9(6):607-10. doi: 10.1097/00008390-199912000-00011. PMID: 10661773. 18: Bayés M, Rabasseda X, Prous JR. Gateways to clinical trials. Methods Find Exp Clin Pharmacol. 2007 Jan-Feb;29(1):53-71. PMID: 17344945. 19: Mathé G, Misset JL, Triana BK, Godenèche D, Madelmont JC, Meyniel G. Phase I trial of cystemustine, a new cysteamine (2-chloroethyl) nitrosourea: an intrapatient escalation scheme. Drugs Exp Clin Res. 1992;18(4):155-8. PMID: 1451646. 20: Curé H, Krakowski I, Adenis A, Tubiana N, Kerbrat P, Roché H, Chevallier B, Lentz MA, Fumoleau P, Chollet P. Results of a phase II trial with second-line cystemustine at 60 mg/m2 in advanced soft tissue sarcoma: a trial of the EORTC Early Clinical Studies Group. Eur J Cancer. 1998 Feb;34(3):422-3. doi: 10.1016/s0959-8049(97)00357-2. PMID: 9640234.