WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 462818
CAS#: 92953-41-8 (free base)
Description: U 54494A is an anticonvulsant biochemical.
MedKoo Cat#: 462818
Name: U 54494A
CAS#: 92953-41-8 (free base)
Chemical Formula: C18H24Cl2N2O
Exact Mass: 354.1266
Molecular Weight: 355.303
Elemental Analysis: C, 60.85; H, 6.81; Cl, 19.95; N, 7.88; O, 4.50
This product is not in stock, which may be available by custom synthesis.
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Related CAS #: 92953-41-8 (free base); 112465-94-8 (hydrochloride)
Synonym: U-54494; U 54494; U-54494A;
IUPAC/Chemical Name: 3,4-dichloro-N-methyl-N-((1R,2R)-2-(pyrrolidin-1-yl)cyclohexyl)benzamide
InChi Key: JUBNVWGVNWIXMB-IAGOWNOFSA-N
InChi Code: InChI=1S/C18H24Cl2N2O/c1-21(18(23)13-8-9-14(19)15(20)12-13)16-6-2-3-7-17(16)22-10-4-5-11-22/h8-9,12,16-17H,2-7,10-11H2,1H3/t16-,17-/m1/s1
SMILES Code: CN(C(c1cc(Cl)c(Cl)cc1)=O)[C@@H]2CCCC[C@H]2N3CCCC3
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
The following data is based on the product molecular weight 355.303 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: Ochoa MC, Vogelsang GD, Lum JT, VonVoigtlander PF, Piercey MF. Effect of the anticonvulsant U-54494A on cortical neuron excitability: comparison to the kappa agonist U-50488H. Life Sci. 1992;50(17):1225-33. doi: 10.1016/0024-3205(92)90322-g. PMID: 1349150.
2: Camacho Ochoa M, Jackson TA, Aaron CS, Lahti RA, Strain GM, Von Voigtlander PF. Antagonism of kainic acid lesions in the mouse hippocampus by U-54494A and U-50488H. Life Sci. 1992;51(14):1135-43. doi: 10.1016/0024-3205(92)90515-q. PMID: 1325589.
3: De Sarro G, Trimarchi GR, Sinopoli S, Masuda Y, De Sarro A. Anticonvulsant effects of U-54494A and U-50488H in genetically epilepsy-prone rats and DBA/2 mice: a possible involvement of glycine/NMDA receptor complex. Gen Pharmacol. 1993 Mar;24(2):439-47. doi: 10.1016/0306-3623(93)90330-z. PMID: 8387056.
4: Proietti ML, Scotti de Carolis A, Frank C, Zeng YC, Sagratella S. In vitro depressant effects of U-54494A, an anticonvulsant related to kappa opioids, in the hippocampus. Neuropharmacology. 1991 Jun;30(6):637-42. doi: 10.1016/0028-3908(91)90084-o. PMID: 1656303.
5: Hudson CJ, Von Voigtlander PF, Althaus JS, Scherch HM, Means ED. The kappa opioid-related anticonvulsants U-50488H and U-54494A attenuate N-methyl-D- aspartate induced brain injury in the neonatal rat. Brain Res. 1991 Nov 15;564(2):261-7. doi: 10.1016/0006-8993(91)91462-a. PMID: 1725768.
6: Fischer W, Bodewei R, VonVoigtlander PF, Müller M. Anticonvulsant and related effects of U-54494A in various seizure tests. J Pharmacol Exp Ther. 1993 Oct;267(1):163-70. PMID: 8229743.
7: Zhu Y, Im HK, Im WB. Block of voltage-gated potassium currents by anticonvulsant U-54494A in mouse neuroblastoma cells. J Pharmacol Exp Ther. 1992 Oct;263(1):207-13. PMID: 1403785.
8: Camacho-Ochoa M, VonVoigtlander PF, Hoffmann WE, Piercey MP. U-54494A reduces 4-AP-induced afterdischarges of CA1 pyramidal cells in the hippocampal slice of the rat. Life Sci. 1992;50(6):457-63. doi: 10.1016/0024-3205(92)90381-x. PMID: 1310340.
9: VonVoigtlander PF, Hall ED, Ochoa MC, Lewis RA, Triezenberg HJ. U-54494A: a unique anticonvulsant related to kappa opioid agonists. J Pharmacol Exp Ther. 1987 Nov;243(2):542-7. PMID: 2824750.
10: Conner-Kerr TA, Terrian DM. Inhibition of glutamate release: a potential mechanism of action for the anticonvulsant U-54494A in the guinea pig hippocampus. Brain Res Bull. 1993;31(5):573-80. doi: 10.1016/0361-9230(93)90125-u. PMID: 8098655.
11: Zhu Y, Im WB, Lewis RA, Althaus JS, Cazers AR, Nielsen JW, Palmer JR, Von Voigtlander PF. Two metabolites of anticonvulsant U-54494A: their anticonvulsant activity and interaction with sodium channel. Brain Res. 1993 Mar 19;606(1):50-5. doi: 10.1016/0006-8993(93)91568-d. PMID: 8384924.
12: Zhu Y, Im WB. Block of sodium channel current by anticonvulsant U-54494A in mouse neuroblastoma cells. J Pharmacol Exp Ther. 1992 Jan;260(1):110-6. PMID: 1309869.
13: Sethy VH, Sage GP. Modulation of release of acetylcholine from the striatum by a proposed excitatory amino acid antagonist U-54494A: comparison with known antagonists, diazepam and phenytoin. Neuropharmacology. 1992 Feb;31(2):111-4. doi: 10.1016/0028-3908(92)90019-l. PMID: 1348110.
14: Zhong WZ, Williams MG, Cook KJ, VandeGiessen TL, Jones BW, Rousch KE. First- pass effect of cis-3,4-dichloro-N-methyl-N-(2-(1-pyrrolidinyl)- cyclohexyl)-benzamide (U-54494) in rats--a model with multiple cannulas for investigation of gastrointestinal and hepatic metabolism. Pharm Res. 1994 Nov;11(11):1524-9. doi: 10.1023/a:1018985015596. PMID: 7870665.
15: Zhong WZ, Williams MG, Schuette MR, Vandegiessen TL, Jones BW. Pharmacokinetics of the individual enantiomers of cis-3,4-dichloro-N- methyl-N-[2-(1-pyrrolidinyl)-cyclohexyl]-benzamide monohydrochloride (U-54494A) in the dog. Enantiomer. 1996;1(2):89-96. PMID: 9676281.
16: Zhu Y, Im WB, Lewis RA, VonVoigtlander PF. Comparison of pyrrolidinyl and piperidinyl benzamides for their anticonvulsant activity and inhibitory action on sodium channel. Br J Pharmacol. 1992 May;106(1):49-54. doi: 10.1111/j.1476-5381.1992.tb14291.x. PMID: 1324068; PMCID: PMC1907445.
17: Yonekawa WD, Kapetanovic IM, Kupferberg HJ. The effects of anticonvulsant agents on 4-aminopyridine induced epileptiform activity in rat hippocampus in vitro. Epilepsy Res. 1995 Feb;20(2):137-50. doi: 10.1016/0920-1211(94)00077-a. PMID: 7750510.
18: De Sarro G, Ascioti C, di Paola ED, Vidal MJ, De Sarro A. Effects of antiepileptic drugs, calcium channel blockers and other compounds on seizures induced by activation of voltage-dependent L calcium channel in DBA/2 mice. Gen Pharmacol. 1992 Nov;23(6):1205-16. doi: 10.1016/0306-3623(92)90313-9. PMID: 1283140.
19: Massotti M, D'Amore A, Lorenzini P, Brusa L. Area tempestas modulates the behavioural responses to nociceptive stimuli in rats. Ann Ist Super Sanita. 1993;29(3):401-7. PMID: 8172458.
20: Zhong WZ, Williams MG. Quantitative determination of cis-3,4-dichloro-N- methyl-N-(2-(1-pyrrolidinyl)-cyclohexyl)-benzamide and three of its metabolites in plasma by high-performance liquid chromatography. J Pharm Sci. 1993 Oct;82(10):1049-53. PMID: 8254491.
