Carbetimer

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

MedKoo CAT#: 412298

CAS#: 82230-03-3

Description: Carbetimer is a partially imidized copolymer of ethylene & maleic anhydride with average MW approx 1,200 daltons; capable of specific stimulation of immune response. Carbetimer is a low molecular weight polymer derived from ethylene and maleic anhydride with potent antineoplastic activity. Preclinical studies have shown antitumor effects against many tumor cell lines including B 16 melanoma. Its antitumor actions are felt to include both reduction of uridine and cytidine nucleoside triphosphate as well as the diminution of pyrimidine salvage by inhibiting uridine, cytidine, and thymidine kinase. Besides direct antiproliferative effects, Carbetimer could act through immunomodulation, as suggested by the induction of cytotoxic T-cells in mice and the discordant in vitro and in vivo activities against the Lewis lung carcinoma model.


Chemical Structure

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Carbetimer
CAS# 82230-03-3

Theoretical Analysis

MedKoo Cat#: 412298
Name: Carbetimer
CAS#: 82230-03-3
Chemical Formula: C24H37N5O8
Exact Mass: 523.2642
Molecular Weight: 523.59
Elemental Analysis: C, 55.06; H, 7.12; N, 13.38; O, 24.45

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: Carbetimer; N137; N 137; N-137

IUPAC/Chemical Name: diazanium;2-[1-amino-4-[2,5-dioxo-4-(1-phenylethyl)pyrrolidin-3-yl]-1-oxobutan-2-yl]-5-carbamoylheptanedioate

InChi Key: InChI=1S/C24H31N3O8.2H3N/c1-12(13-5-3-2-4-6-13)19-17(22(32)27-23(19)33)10-9-15(21(26)31)16(24(34)35)8-7-14(20(25)30)11-18(28)29;;/h2-6,12,14-17,19H,7-11H2,1H3,(H2,25,30)(H2,26,31)(H,28,29)(H,34,35)(H,27,32,33);2*1H3

SMILES Code: CC(C1=CC=CC=C1)C2C(CCC(C(N)=O)C(C([O-])=O)CCC(C(N)=O)CC([O-])=O)C(NC2=O)=O.[NH4+].[NH4+]

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: >3 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 523.59 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: Quan WD Jr, Mitchell MS. Phase II trial of carbetimer in metastatic melanoma. Invest New Drugs. 1993 May-Aug;11(2-3):231-3. doi: 10.1007/BF00874162. PMID: 8262738.

2: Ardalan B, Hussein AM, Shanahan WR Jr, Shields MJ. Carbetimer: a re- evaluation of a drug with a novel mechanism of action. Cancer Treat Rev. 1991 Mar;18(1):73-83. doi: 10.1016/0305-7372(91)90005-k. PMID: 1933912.

3: Body JJ, Nejai S, Fernandez G, Glibert F, O'Bryan-Tear G. Effects of Carbetimer, a new antineoplastic drug, on bone metabolism. Bone. 1991;12(3):139-42. doi: 10.1016/8756-3282(91)90035-h. PMID: 1910954.

4: Brown TD, Burris HA, Havlin KA, O'Rourke TJ, Rodriguez GI, Wall JG, Weiss GR. New anticancer agents. Cancer Chemother Biol Response Modif. 1991;12:111-46. PMID: 1718374.

5: Keaton M, Brown T, Craig J, Fries G, Harmon G, Zaloznik A, Orczyk G, Von Hoff D. Phase II study of carbetimer in non-small cell lung cancer. Invest New Drugs. 1990 Nov;8(4):385-6. doi: 10.1007/BF00198596. PMID: 1964676.

6: Audeh MW, Jacobs CD, Davis TE, Carlson RW. A phase II trial of carbetimer for the treatment of colorectal cancer. A trial of the Northern California Oncology Group. Am J Clin Oncol. 1990 Aug;13(4):324-6. doi: 10.1097/00000421-199008000-00012. PMID: 2198795.

7: Grunberg SM, Ehler E, Francis RB Jr, Mitchell MS. Phase I trial of a 5-day course of carbetimer. Invest New Drugs. 1990;8 Suppl 1:S41-9. doi: 10.1007/BF00171983. PMID: 2380016.

8: Body JJ, Magritte A, Cleeren A, Borkowski A, Dodion P. Short-term effects of Carbetimer on calcium and bone metabolism in man. Eur J Cancer Clin Oncol. 1989 Dec;25(12):1831-5. doi: 10.1016/0277-5379(89)90355-6. PMID: 2632264.

9: Dodion P, de Valeriola D, Body JJ, Houa M, Noel P, Abrams J, Crespeigne N, Wery F, Kenis Y. Phase I clinical trial with carbetimer. Eur J Cancer Clin Oncol. 1989 Feb;25(2):279-86. doi: 10.1016/0277-5379(89)90020-5. PMID: 2539292.

10: Hanauske AR, Melink TJ, Harman GS, Clark GM, Craig JB, Koeller JM, Boldt DH, Kantor B, Kisner DL, Orczyk G, et al. Phase I clinical trial of carbetimer. Cancer Res. 1988 Sep 15;48(18):5353-7. PMID: 2842047.

11: Fromm M, Berdel WE, Schick HD, Danhauser-Riedl S, Fink U, Remy W, Reichert A, Ankele A, Präuer HW, Siewert JR, et al. Phase I trial of the polyelectrolyte carbetimer administered i.v. once every four weeks. Invest New Drugs. 1988 Sep;6(3):189-94. doi: 10.1007/BF00175396. PMID: 3192384.

12: Weiss GR, Arteaga CL, Brown TD, Craig JB, Harman GS, Havlin KA, Koeller JM, Kuhn JG, Von Hoff DD. New anticancer agents. Cancer Chemother Biol Response Modif. 1988;10:85-116. PMID: 2484323.

13: Ardalan B, Paget GE. Mechanism of action of a new antitumor agent, carbetimer. Cancer Res. 1986 Nov;46(11):5473-6. PMID: 3756894.

14: Harris GJ, Turner JN, Von Hoff DD. Growth of carcinoma of the esophagus and gastroesophageal junction in a human tumor cloning assay. Cancer Drug Deliv. 1986 Fall;3(4):273-8. doi: 10.1089/cdd.1986.3.273. PMID: 3567847.

15: Kisner DL, Mehta P, Paget GE, Von Hoff DD. Activity of Carbetimer in a human tumor cloning system. Invest New Drugs. 1984;2(1):55-8. doi: 10.1007/BF00173787. PMID: 6469499.

16: Teodorczyk-Injeyan JA, Filion L, Falk J, Falk R, Makowka L. Mechanism of enhanced humoral response in rodents by a synthetic polymer. J Immunopharmacol. 1983;5(3):147-72. doi: 10.3109/08923978309039103. PMID: 6655252.

17: Fields JE, Asculai SS, Johnson JH, Johnson RK. Carboxyimamidate, a low- molecular-weight polyelectrolyte with antitumor properties and low toxicity. J Med Chem. 1982 Sep;25(9):1060-4. doi: 10.1021/jm00351a011. PMID: 7131485.

18: Rees RC, Potter CW, Clegg A, Hall JM. Studies on the antitumour effects of N-137. Chemotherapy. 1982;28(4):283-90. doi: 10.1159/000238091. PMID: 7116980.

19: Teodorczyk-Injeyan JA, Makowka L, Falk RE, Falk JA. Mechanisms of altered in vitro antibody response in the rat by a small synthetic polymer. Scand J Immunol. 1982 Jan;15(1):9-16. doi: 10.1111/j.1365-3083.1982.tb00616.x. PMID: 7041246.

20: Falk RE, Makowka L, Bugala R, Falk JA, Rotstein LE, Ambus U. Clinical evaluation of a synthetic low molecular weight polymer for advanced gastrointestinal cancer. Clin Invest Med. 1981;4(3-4):155-9. PMID: 7337985.