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| ln Vitro |
By covalently altering the substrate binding site, caracemide renders R1 inactive and generates the hazardous metabolite methyl isocyanate (MIC) in vivo [1][2].
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| ln Vivo |
After intraperitoneal injection of a single dose (6.6 mg/kg) of caracemide (NSC-253272), rats' urine was found to contain the thiol acid derivative AMCC [1]. The infiltration of PAF-induced conjunctival eosinophils was significantly inhibited by bepotastine (10 g/L); eye drops applied three times to one eye, separated by twenty minutes [1]. When compared to the control group, bepotastine (3 mg/kg; oral; once) nearly equally inhibited scratching behavior, with a frequency of 59.0 and a duration of 14.57 seconds [3]. Serum LTB 4 levels in rash-ridden NC/Nga mice were markedly suppressed by bepotastine (10 mg/kg; oral; once), reaching 711.3 pg/mL at one hour and 858.8 pg/mL at two hours [3].
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| Toxicity/Toxicokinetics |
Toxicity Data
Mouse(po): LD50: 388 mg/kg Mouse(ip): L50:D 167 mg/kg Mouse(iv): LD50: 238 mg/kg |
| References |
[1]. Slatter JG, et al. 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.
[2]. Larsen IK, et al. Caracemide, a site-specific irreversible inhibitor of protein R1 of Escherichia coli ribonucleotide reductase. J Biol Chem. 1992 Jun 25;267(18):12627-31. |
| Additional Infomation |
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. (NCI04)
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| Molecular Formula |
C6H11N3O4
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|---|---|
| Molecular Weight |
189.16924
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| Exact Mass |
189.075
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| CAS # |
81424-67-1
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| PubChem CID |
54747
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| Appearance |
White to off-white solid powder
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| Density |
1.259g/cm3
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| Index of Refraction |
1.479
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| LogP |
0.227
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| Hydrogen Bond Donor Count |
2
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| Hydrogen Bond Acceptor Count |
4
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| Rotatable Bond Count |
2
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| Heavy Atom Count |
13
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| Complexity |
228
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| Defined Atom Stereocenter Count |
0
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| SMILES |
O=C(NC)ON(C(C)=O)C(NC)=O
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| InChi Key |
JURAJLFHWXNPHG-UHFFFAOYSA-N
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| 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)
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| Chemical Name |
[acetyl(methylcarbamoyl)amino] N-methylcarbamate
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
DMSO : ~100 mg/mL (~528.63 mM)
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|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (13.22 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (13.22 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. View More
Solubility in Formulation 3: ≥ 2.5 mg/mL (13.22 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 5.2863 mL | 26.4313 mL | 52.8625 mL | |
| 5 mM | 1.0573 mL | 5.2863 mL | 10.5725 mL | |
| 10 mM | 0.5286 mL | 2.6431 mL | 5.2863 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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