WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 406153
Description: Hepsulfam is a bisulfamic ester which is similar in structure to busulfan and belongs to the family of drugs known as alkylsulfonate alkylating agents. Hepsulfam forms covalent linkages with nucleophilic centers in DNA, resulting in depurination, base miscoding, strand scission, DNA-DNA and DNA-protein cross-linking, and cytotoxicity. Check for active clinical trials or closed clinical trials using this agent. (NCI Thesaurus)
MedKoo Cat#: 406153
Chemical Formula: C7H18N2O6S2
Exact Mass: 290.06063
Molecular Weight: 290.36
Elemental Analysis: C, 28.96; H, 6.25; N, 9.65; O, 33.06; S, 22.09
IUPAC/Chemical Name: heptane-1,7-diyl bis(sulfamate)
InChi Key: GOJJWDOZNKBUSR-UHFFFAOYSA-N
InChi Code: InChI=1S/C7H18N2O6S2/c8-16(10,11)14-6-4-2-1-3-5-7-15-17(9,12)13/h1-7H2,(H2,8,10,11)(H2,9,12,13)
SMILES Code: O=S(OCCCCCCCOS(=O)(N)=O)(N)=O
Appearance: solid powder
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: >5 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
The following data is based on the product molecular weight 290.36 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: Je KH, Son JK, O'Connor TR, Lee CS. Hepsulfam induced DNA adducts and its excision repair by bacterial and mammalian 3-methyladenine DNA glycosylases. Mol Cells. 1998 Dec 31;8(6):691-7. PubMed PMID: 9895121.
2: Streeper RT, Cotter RJ, Colvin ME, Hilton J, Colvin OM. Molecular pharmacology of hepsulfam, NSC 3296801: identification of alkylated nucleosides, alkylation site, and site of DNA cross-linking. Cancer Res. 1995 Apr 1;55(7):1491-8. PubMed PMID: 7882358.
3: Larson RA, Geller RB, Janisch L, Milton J, Grochow LB, Ratain MJ. Encephalopathy is the dose-limiting toxicity of intravenous hepsulfam: results of a phase I trial in patients with advanced hematological malignancies. Cancer Chemother Pharmacol. 1995;36(3):204-10. PubMed PMID: 7781139.
4: Marshall MV, Carey KD, Von Hoff DD, Kuhn JG. Hepsulfam distribution in blood, plasma and cerebrospinal fluid of baboons. Invest New Drugs. 1995;13(1):33-6. PubMed PMID: 7499105.
5: Marshall MV, Marshall MH, Degen DR, Roodman GD, Kuhn JG, Ross ME, Von Hoff DD. In vitro cytotoxicity of hepsulfam against human tumor cell lines and primary human tumor colony forming units. Stem Cells. 1993 Jan;11(1):62-9. PubMed PMID: 8457783.
6: Berger DP, Winterhalter BR, Dengler WA, Fiebig HH. Preclinical activity of hepsulfam and busulfan in solid human tumor xenografts and human bone marrow. Anticancer Drugs. 1992 Oct;3(5):531-9. PubMed PMID: 1450448.
7: Armstrong DK, Gordon GB, Hilton J, Streeper RT, Colvin OM, Davidson NE. Hepsulfam sensitivity in human breast cancer cell lines: the role of glutathione and glutathione S-transferase in resistance. Cancer Res. 1992 Mar 15;52(6):1416-21. PubMed PMID: 1540950.
8: Ravdin PM, Havlin KA, Marshall MV, Brown TD, Koeller JM, Kuhn JG, Rodriguez G, Von Hoff DD. A phase I clinical and pharmacokinetic trial of hepsulfam. Cancer Res. 1991 Dec 1;51(23 Pt 1):6268-72. PubMed PMID: 1933887.
9: Hendricks CB, Grochow LB, Rowinsky EK, Forastiere AA, McGuire WP, Ettinger DS, Sartorius S, Lubejko B, Donehower RC. Phase I and pharmacokinetic study of hepsulfam (NSC 329680). Cancer Res. 1991 Nov 1;51(21):5781-5. PubMed PMID: 1933848.
10: Du DL, Volpe DA, Grieshaber CK, Murphy MJ Jr. Comparative toxicity of fostriecin, hepsulfam and pyrazine diazohydroxide to human and murine hematopoietic progenitor cells in vitro. Invest New Drugs. 1991 May;9(2):149-57. PubMed PMID: 1874599.
11: Hincks JR, Adlakha A, Cook CA, Johnson CS, Furmanski P, Gibson NW. In vitro studies on the mechanism of action of hepsulfam in chronic myelogenous leukemia patients. Cancer Res. 1990 Dec 1;50(23):7559-63. PubMed PMID: 2253205.
12: Pacheco DY, Cook C, Hincks JR, Gibson NW. Mechanisms of toxicity of hepsulfam in human tumor cell lines. Cancer Res. 1990 Dec 1;50(23):7555-8. PubMed PMID: 2253204.
13: Pacheco DY, Stratton NK, Gibson NW. Comparison of the mechanism of action of busulfan with hepsulfam, a new antileukemic agent, in the L1210 cell line. Cancer Res. 1989 Sep 15;49(18):5108-10. PubMed PMID: 2766282.