Sarmustine

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

MedKoo CAT#: 206758

CAS#: 81965-43-7

Description: Sarmustine, also known as SarCNU, is an alkylating agent potentially for the treatment of recurrent malignant glioma. SarCNU inhibits prostate carcinoma cell growth via p53-dependent and p53-independent pathways. SarCNU mediates selection of P140K methylguanine-DNA-methyltransferase transduced human CD34(+) cells in vitro.


Chemical Structure

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Sarmustine
CAS# 81965-43-7

Theoretical Analysis

MedKoo Cat#: 206758
Name: Sarmustine
CAS#: 81965-43-7
Chemical Formula: C6H11ClN4O3
Exact Mass: 222.052
Molecular Weight: 222.629
Elemental Analysis: C, 32.37; H, 4.98; Cl, 15.92; N, 25.17; O, 21.56

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

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Synonym: Sarmustine; SarCNU; NSC-364432; NSC 364432; NSC364432; Sarcosinamide; chloroethyl nitrosourea; Sarcosinamide; chloroethylnitrosourea.

IUPAC/Chemical Name: 1-(Carbamoylmethyl)-3-(2-chloroethyl)-1-methyl-3-nitrosourea

InChi Key: HYHJFNXFVPGMBI-UHFFFAOYSA-N

InChi Code: InChI=1S/C6H11ClN4O3/c1-10(4-5(8)12)6(13)11(9-14)3-2-7/h2-4H2,1H3,(H2,8,12)

SMILES Code: O=C(N(CCCl)N=O)N(CC(N)=O)C

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

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

Preparing Stock Solutions

The following data is based on the product molecular weight 222.629 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.

Recalculate based on batch purity %
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

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1: Wong RP, Baetz T, Krahn MJ, Biagi J, Wainman N, Eisenhauer E; National Cancer Institute of Canada Clinical Trials Group.. SarCNU in recurrent or metastatic colorectal cancer: a phase II study of the National Cancer Institute of Canada Clinical Trials Group. Invest New Drugs. 2006 Jul;24(4):347-51. PubMed PMID: 16502354.

2: Nguyen TH, Ong CK, Wong E, Leong CT, Panasci L, Huynh H. 2-Chloroethyl-3-sarcosinamide-1-nitrosourea (SarCNU) exhibits p53-dependent and -independent antiproliferative activity in human nasopharyngeal carcinoma cells in vitro and in vivo. Int J Oncol. 2005 Oct;27(4):1131-40. PubMed PMID: 16142332.

3: Webster M, Cairncross G, Gertler S, Perry J, Wainman N, Eisenhauer E. Phase II trial of SarCNU in malignant glioma: unexpected pulmonary toxicity with a novel nitrosourea: a phase II trial of the national cancer institute of canada clinical trials group. Invest New Drugs. 2005 Dec;23(6):591-6. PubMed PMID: 16034522.

4: Hung H, Pierce CK, Chee SK, Lawrence P, Hung NT. SarCNU-induced G2/M arrest in hepatoma cells is mediated by a p53-independent phosphorylation of cdc-2 at Tyr15. J Cell Physiol. 2005 Sep;204(3):785-91. PubMed PMID: 15754328.

5: Huynh H, Nguyen TH, Panasci L, Do P. 2-Chloroethyl-3-sarcosinamide-1-nitrosourea (SarCNU) inhibits prostate carcinoma cell growth via p53-dependent and p53-independent pathways. Cancer. 2004 Dec 15;101(12):2881-91. PubMed PMID: 15529313.

6: Zielske SP, Gerson SL. SarCNU mediates selection of P140K methylguanine-DNA-methyltransferase transduced human CD34(+) cells in vitro. Blood Cells Mol Dis. 2003 Jul-Aug;31(1):48-50. PubMed PMID: 12850483.

7: Panasci L, Stinson SF, Melnychuk D, Sandor V, Miller WH Jr, Batist G, Patenaude F, Bangash N, Panarello L, Alaoui-Jamali M, Sausville E. SarCNU, a nitrosourea analog on a day 1, 5, and 9 oral schedule: a phase I and pharmacokinetic study in patients with advanced solid tumors. J Clin Oncol. 2003 Jan 15;21(2):232-40. PubMed PMID: 12525514.

8: Ni N, Sanghvi T, Yalkowsky SH. Stabilization and preformulation of anticancer drug--SarCNU. Int J Pharm. 2002 Dec 5;249(1-2):257-64. PubMed PMID: 12433453.

9: Chen Z, Panasci LC, Carter CA. [Expression of extraneuronal monoamine transporter gene and DNA repair gene vis-à-vis with antitumor efficacy of SarCNU in human tumor xenografts]. Zhonghua Zhong Liu Za Zhi. 2001 Mar;23(2):122-4. Chinese. PubMed PMID: 11783015.

10: Chen ZP, Pan J, Huang Q, Sun ZF, Zhou LY, Wang AD. Antitumor efficacy of SarCNU in a human glioma xenograft model expressing both MGMT and extraneuronal monoamine transporter. J Neurooncol. 2001 Jan;51(1):19-24. PubMed PMID: 11349876.

11: Chen ZP, Wang G, Huang Q, Sun ZF, Zhou LY, Wang AD, Panasci LC. Enhanced antitumor activity of sarCNU in comparison to BCNU in an extraneuronal monoamine transporter positive human glioma xenograft model. J Neurooncol. 1999 Aug;44(1):7-14. PubMed PMID: 10582663.

12: Takeda N, Diksic M. Relationship between drug delivery and the intra-arterial infusion rate of SarCNU in C6 rat brain tumor model. J Neurooncol. 1999 Feb;41(3):235-46. PubMed PMID: 10359143.

13: Noë AJ, Marcantonio D, Barton J, Malapetsa A, Panasci LC. Characterization of the catecholamine extraneuronal uptake2 carrier in human glioma cell lines SK-MG-1 and SKI-1 in relation to (2-chloroethyl)-3-sarcosinamide-1-nitrosourea (SarCNU) selective cytotoxicity. Biochem Pharmacol. 1996 Jun 28;51(12):1639-48. PubMed PMID: 8687479.

14: Panasci LC, Marcantonio D, Noë AJ. SarCNU (2-chloroethyl-3-sarcosinamide-1-nitrosourea): a novel analogue of chloroethylnitrosourea that is transported by the catecholamine uptake2 carrier, which mediates increased cytotoxicity. Cancer Chemother Pharmacol. 1996;37(6):505-8. PubMed PMID: 8612302.

15: Mitsuki S, Diksic M, Conway T, Yamamoto YL, Villemure JG, Feindel W. Pharmacokinetics of 11C-labelled BCNU and SarCNU in gliomas studied by PET. J Neurooncol. 1991 Feb;10(1):47-55. PubMed PMID: 1902507.

16: Skalski V, Yarosh DB, Batist G, Gros P, Feindel W, Kopriva D, Panasci LC. Mechanisms of resistance to (2-chloroethyl)-3-sarcosinamide-1-nitrosourea (SarCNU) in sensitive and resistant human glioma cells. Mol Pharmacol. 1990 Sep;38(3):299-305. PubMed PMID: 2402223.

17: Schipper HM, Skalski V, Panasci LC, Wang E. Statin expression in the untreated and SarCNU-exposed human glioma cell line, SK-MG-1. Cancer Chemother Pharmacol. 1990;26(5):383-6. PubMed PMID: 2208582.

18: Conway T, Diksic M. Synthesis of "no-carrier-added" carbon-11 SarCNU: the sarcosinamide analog of the chemotherapeutic agent BCNU. J Nucl Med. 1988 Dec;29(12):1957-60. PubMed PMID: 3193209.

19: Skalski V, Rivas J, Panasci L, McQuillan A, Feindel W. The cytotoxicity of sarcosinamide chloroethylnitrosourea (SarCNU) and BCNU in primary gliomas and glioma cell lines: analysis of data in reference to theoretical peak plasma concentrations in man. Cancer Chemother Pharmacol. 1988;22(2):137-40. PubMed PMID: 3409444.