Carbetimer | CAS# 82230-03-3 | immune response

MedKoo Cat#: 412298 | Name: Carbetimer

Description:

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

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

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 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 #

No Data

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

InChi Code

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

More Info

Instruction

View handling instruction

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.

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: 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.