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MedKoo Cat#: 206523 | Name: Caracemide

Description:

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

Caracemide is an agent derived from acetohydroxamic acid with potential antineoplastic activity. Caracemide inhibits ribonuclease reductase, resulting in decreased DNA synthesis and tumor growth; it also inhibits acetylcholinesterase. In vivo, caracemide contributes to the formation of the neurotoxin methyl isocyanate; this effect, along with the agent's acetylcholinesterase activity, may be responsible for the severe central nervous system toxicity observed in clinical trials.

Chemical Structure

Caracemide
Caracemide
CAS#81424-67-1

Theoretical Analysis

MedKoo Cat#: 206523

Name: Caracemide

CAS#: 81424-67-1

Chemical Formula: C6H11N3O4

Exact Mass: 189.0750

Molecular Weight: 189.17

Elemental Analysis: C, 38.10; H, 5.86; N, 22.21; O, 33.83

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
NSC-253272; NSC 253272; NSC253272; Caracemide
IUPAC/Chemical Name
N-(methylcarbamoyl)-N-((methylcarbamoyl)oxy)acetamide
InChi Key
JURAJLFHWXNPHG-UHFFFAOYSA-N
InChi Code
InChI=1S/C6H11N3O4/c1-4(10)9(5(11)7-2)13-6(12)8-3/h1-3H3,(H,7,11)(H,8,12)
SMILES Code
CC(=O)N(C(=O)NC)OC(=O)NC
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, not in water
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 189.17 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: Egan JA, Filer CN. Tritiation and characterization of several suicide substrate enzyme inactivators. Appl Radiat Isot. 2014 Dec;94:302-5. doi: 10.1016/j.apradiso.2014.08.022. Epub 2014 Sep 16. PubMed PMID: 25305521. 2: Witte RS, Lipsitz S, Goodman TL, Asbury RF, Wilding G, Strnad CM, Smith TJ, Haller DG. A phase II trial of homoharringtonine and caracemide in the treatment of patients with advanced large bowel cancer. Invest New Drugs. 1999;17(2):173-7. PubMed PMID: 10638488. 3: Witte RS, Hsieh P, Elson P, Oken MM, Trump DL. A phase II trial of amonafide, caracemide, and homoharringtonine in the treatment of patients with advanced renal cell cancer. Invest New Drugs. 1996;14(4):409-13. PubMed PMID: 9157078. 4: Slatter JG, Davis MR, Han DH, Pearson PG, Baillie TA. Studies on the metabolic fate of caracemide, an experimental antitumor agent, in the rat. Evidence for the release of methyl isocyanate in vivo. Chem Res Toxicol. 1993 May-Jun;6(3):335-40. PubMed PMID: 8318655. 5: Larsen IK, Cornett C, Karlsson M, Sahlin M, Sjöberg BM. Caracemide, a site-specific irreversible inhibitor of protein R1 of Escherichia coli ribonucleotide reductase. J Biol Chem. 1992 Jun 25;267(18):12627-31. PubMed PMID: 1618768. 6: Lad T, Schor J, Mullane M, Carroll R, Chernicoff D, Blough R, Weidner L. Phase II trial of caracemide (NSC 253272) in advanced unresectable non-small cell bronchogenic carcinoma. An Illinois Cancer Council study. Invest New Drugs. 1992 Apr;10(1):27-8. PubMed PMID: 1318870. 7: Buccafusco JJ, Smith MD. In vivo and in vitro cholinesterase inhibitor property of the antitumor agent caracemide. Res Commun Chem Pathol Pharmacol. 1990 Feb;67(2):219-27. PubMed PMID: 2333410. 8: Satyamoorthy K, Deshpande SS, Chitnis MP. Differential effect of collaterally sensitive antimetabolites on P388 murine leukemia sensitive and resistant to adriamycin in vitro. Neoplasma. 1989;36(6):673-83. PubMed PMID: 2515459. 9: Ho BT, Tansey LW, Feiffer R, Newman RA, Farquhar D, Fields WS, Krakoff IH. The effect of the experimental antitumor agent caracemide on brain choline acetyltransferase. J Neurosci Res. 1988;19(1):119-21. PubMed PMID: 3343703. 10: Satyamoorthy K, Chitnis MP, Advani SH. In vitro cytotoxicity of caracemide alone and in combination with hydroxyurea or iron-chelating agents in human chronic myeloid leukemia cells and murine tumors. Neoplasma. 1988;35(1):27-35. PubMed PMID: 3162554. 11: Pazdur R, Chabot GG, Baker LH. Phase I study and pharmacokinetics of caracemide (NSC-253272) administered as a short infusion. Invest New Drugs. 1987 Dec;5(4):365-71. PubMed PMID: 3436742. 12: Belani CP, Eisenberger M, Van Echo D, Hiponia D, Aisner J. Phase II study of caracemide in advanced or recurrent non-small cell lung cancer. Cancer Treat Rep. 1987 Nov;71(11):1099-100. PubMed PMID: 2824047. 13: Fan D, Ajani JA, Baker FL, Tomasovic B, Brock WA, Spitzer G. Comparison of antitumor activity of standard and investigational drugs at equivalent granulocyte-macrophage colony-forming cell inhibitory concentrations in the adhesive tumor cell culture system: an in vitro method of screening new drugs. Eur J Cancer Clin Oncol. 1987 Oct;23(10):1469-76. PubMed PMID: 2890527. 14: Raber MN, Adams F, Kavanagh J, Legha S, Dimery I, Krakoff I. Phase I trial of caracemide using bolus and infusion schedules. Cancer Treat Rep. 1987 Apr;71(4):349-52. PubMed PMID: 3548956. 15: Newman RA, Farquhar D. Release of methyl isocyanate from the antitumor agent caracemide (NSC-253272). Invest New Drugs. 1987;5(3):267-71. PubMed PMID: 3667162. 16: Lee MS, Lin DP, Wang CY. Mutagenicity of the anticancer drug, caracemide, and related compounds for salmonella. Mutat Res. 1986 Dec;172(3):199-209. PubMed PMID: 3537776. 17: Newman RA, Farquhar D, Lu K, Meyn R, Moore EC, Massia S, Korp JD, Wright JA, McKinney M. Biochemical pharmacology of N-acetyl-N-(methylcarbamoyloxy)-N'-methylurea (caracemide; NSC-253272). Biochem Pharmacol. 1986 Aug 15;35(16):2781-7. PubMed PMID: 3527174. 18: McKinney M, Pfenning M, Richelson E. Effect of the antitumor drug caracemide on the neurochemistry of murine neuroblastoma cells (clone N1E-115). Biochem Pharmacol. 1986 Aug 1;35(15):2615-22. PubMed PMID: 2874811. 19: Moore EC, Loo TL. Inhibition of ribonucleotide reductase by caracemide. Cancer Treat Rep. 1984 Oct;68(10):1293-4. PubMed PMID: 6395952.