Caracemide

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

MedKoo CAT#: 206523

CAS#: 81424-67-1

Description: 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

CAS# 81424-67-1

Instruction

Theoretical Analysis

MedKoo Cat#: 206523
Name: Caracemide
CAS#: 81424-67-1
Chemical Formula: C6H11N3O4
Exact Mass: 189.08
Molecular Weight: 189.171
Elemental Analysis: C, 38.10; H, 5.86; N, 22.21; O, 33.83

Price and Availability

Size	Price	Availability	Quantity
10mg	USD -2
25mg	USD -2
50mg	USD -2
100mg	USD -2
200mg	USD -2
500mg	USD -2
10g	USD -1
20g	USD -1
50g	USD -1
1g	USD -1
2g	USD -1
5g	USD -1
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

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:

Instruction:

View handling instruction

Biological target:
In vitro activity:
In vivo activity:

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.

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

Formulation protocol:
In vitro protocol:
In vivo protocol:

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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.

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