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MedKoo Cat#: 584274 | Name: Bromebrate sodium

Description:

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

Bromebrate sodium, also known as Cytembena, is a nonmyelosuppressive drug that has received phase I--II trials.

Chemical Structure

Bromebrate sodium
Bromebrate sodium
CAS#21739-91-3 (sodium)

Theoretical Analysis

MedKoo Cat#: 584274

Name: Bromebrate sodium

CAS#: 21739-91-3 (sodium)

Chemical Formula: C11H8BrNaO4

Exact Mass: 305.9504

Molecular Weight: 307.07

Elemental Analysis: C, 43.03; H, 2.63; Br, 26.02; Na, 7.49; O, 20.84

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.
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Related CAS #
5711-40-0 (free acid) 21739-91-3 (sodium)
Synonym
Bromebric acid sodium salt; Cytembena; NSC 104801;
IUPAC/Chemical Name
2-Butenoic acid, 3-bromo-4-(4-methoxyphenyl)-4-oxo-, sodium salt, (2E)-
InChi Key
DVDCIQWIGOVWEX-MLBSPLJJSA-M
InChi Code
InChI=1S/C11H9BrO4.Na/c1-16-8-4-2-7(3-5-8)11(15)9(12)6-10(13)14;/h2-6H,1H3,(H,13,14);/q;+1/p-1/b9-6+;
SMILES Code
O=C([O-])/C=C(Br)\C(C1=CC=C(OC)C=C1)=O.[Na+]
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
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 307.07 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
1: Havlík I, Janků I. Studium kinetiky 14C-cytembeny po nitrozilním podání u králíků s pouzitím autoradiografie na tenké vrstvĕ [A study of the kinetics of 14C-cytembena after intravenous administration in rabbits using thin-layer autoradiography]. Cesk Farm. 1983 Sep;32(7):241-4. Czech. PMID: 6688969. 2: Georgoulias V, Misset JL, Ribaud P, Machover D, De Vassal F, Dorval T, Musset M, Schwarzenberg L, Reizenstein P, Mathe G, Gaget H. Doxorubicin, vincristine, bleomycin, cytembena and cisplatin as combination chemotherapy for squamous cell lung cancer. Anticancer Res. 1983 Mar-Apr;3(2):107-10. PMID: 6189445. 3: Huff J. Cytembena: Condensation of the Carcinogenesis Bioassay Technical Report. Environ Health Perspect. 1982 Nov;45:201-3. PMID: 17539167; PMCID: PMC1568995. 4: Mayo JR, DeSouza JJ, Malspeis L, Feller DR. Evidence for the nonenzymatic and irreversible binding of cytembena to rat liver microsomes in vitro. Biochem Pharmacol. 1982 Oct 15;31(20):3201-5. doi: 10.1016/0006-2952(82)90550-0. PMID: 6897357. 5: Ronot X, Adolphe M, Kuch D, Jaffray P, Lechat P, Deysson G. Effect of sodium cis-beta-4-methoxybenzoyl-beta-bromacrylate (Cytembena) on HeLa cell kinetics. Cancer Res. 1982 Aug;42(8):3193-5. PMID: 6896468. 6: Cardone A, Tolino A, Di Serio C, Zarcone R, Borruto Caracciolo G, Ronsini S. Cytembena and cis-platinum in combination for advanced stage ovarian carcinoma treatment. Clin Exp Obstet Gynecol. 1982;9(2):84-94. PMID: 6897625. 7: National Toxicology Program. Carcinogenesis Bioassay of Cytembena (CAS No. 21739-91-3). Natl Toxicol Program Tech Rep Ser. 1981 May;207:1-113. PMID: 12778228. 8: Ronot X, Kuch D, Hecquet C, Adolphe M, Lechat P, Deysson G. Effet inhibiteur du Cytembena (cis-beta-methoxybenzoyl-beta-bromacrylate de sodium) sur la cinétique des cellules HeLa en culture [Inhibitory effect of cytembena (sodium- cis-beta-methoxybenzoyl-beta-bromoacrylate) on the cell kinetics of HeLa cells in culture]. C R Seances Acad Sci D. 1980 Dec 8;291(12):961-4. French. PMID: 6784949. 9: Matĕjková E, Jandová A, Pezlarová A, Rezábek K. Vliv cytembeny cyklofosfamidu a jejich kombinace na katalytickou aktivitu plazmatických enzymů krys zdravých a krys s Yoshidovým sarkomem [Effect of cytembena, cyclophosphamide and their combination on the catalytic activity of plasma enzymes of healthy rats and rats with Yoshida's sarcoma (author's transl)]. Sb Lek. 1980;82(11-12):356-62. Czech. PMID: 6894040. 10: Neidhart JA, Staubus AE, Young D, Balcerzak SP, Malspes IL. Oral cytembena absorption and phase I--II studies. Cancer Treat Rep. 1978 Mar;62(3):401-4. PMID: 348307. 11: Edmonson JH, Decker DG, Malkasian GD, Webb MJ, Jorgensen EO. Phase II evaluation of cytembena (NSC-104801) in patients with advanced ovarian carcinoma resistant to alkylating agents: brief communication. J Natl Cancer Inst. 1977 Dec;59(6):1619-20. doi: 10.1093/jnci/59.6.1619. PMID: 579188. 12: A phase II clinical trial of cytembena. Clinical screening group of E.O.R.T.C. Biomedicine. 1977 Dec;26(6):392-5. PMID: 342004. 13: Von Hoff DD, Rozencweig M, Muggia FM. Cytembena: an anticancer drug with an unique structure. Biomedicine. 1977 Dec;26(6):388-92. PMID: 342003. 14: Berger NA, Weber G. Description of a permeable eukaryotic cell system to study agents affecting DNA synthesis: demonstration that cytembena is a direct inhibitor of replicative DNA synthesis. J Natl Cancer Inst. 1977 Apr;58(4):1167-9. doi: 10.1093/jnci/58.4.1167. PMID: 576624. 15: Mitoma C, Saito T, Howd RA. Metabolic disposition of cytembena in rats and dogs. Xenobiotica. 1977 Mar;7(3):165-79. doi: 10.3109/00498257709036248. PMID: 576751. 16: Berndt WO. A further characterization of cytembena-induced nephrotoxicity. Toxicol Appl Pharmacol. 1977 Feb;39(2):207-17. doi: 10.1016/0041-008x(77)90154-5. PMID: 576748. 17: Novotná J, Jandová A, Janousková M, Laurová L, Skoda V. Hladiny DNA a RNA v tkáni karcinomů colli uteri pred a po podání Cytembeny [Levels of DNA and RNA in the carcinomatous tissue of the collum uteri before and after application of Cytembena (author's transl)]. Cesk Gynekol. 1976 Dec;41(10):733-4. Czech. PMID: 1036977. 18: Falkson HC, Falkson G. Phase II trial of cytembena in patients with advanced ovarian and breast cancer. Cancer Treat Rep. 1976 Nov;60(11):1655-8. PMID: 1037286. 19: Goetz P, Srám RJ, Kodýková I, Dohnalová J, Dostálová O, Bartova J. Relationship between experimental results in mammals and man. II. Cytogenetic analysis of bone-marrow cells after treatment of cytembena and cyclophosphamide- cytembena combination. Mutat Res. 1976 Nov 1;41(1 spel. no):143-52. doi: 10.1016/0027-5107(76)90084-1. PMID: 1037016. 20: Baker LH, Samson MK, Izbicki RM. Phase I and II evaluation of cytembena in disseminated epithelial ovarian cancers and sarcomas. Cancer Treat Rep. 1976 Sep;60(9):1389-91. PMID: 189923.