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MedKoo Cat#: 591098 | Name: Ameltolide
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Description:

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

Ameltolide is a synthetic compound with anticonvulsant properties, originally developed as a potential treatment for epilepsy. It functions primarily by modulating voltage-gated sodium channels, thereby stabilizing neuronal membranes and reducing the hyperexcitability that leads to seizures. Though it showed promise in preclinical models, ameltolide has not progressed to widespread clinical use, and its precise mechanism of action and pharmacological profile remain under further investigation.

Chemical Structure

Ameltolide
Ameltolide
CAS#787-93-9

Theoretical Analysis

MedKoo Cat#: 591098

Name: Ameltolide

CAS#: 787-93-9

Chemical Formula: C15H16N2O

Exact Mass: 240.1263

Molecular Weight: 240.31

Elemental Analysis: C, 74.97; H, 6.71; N, 11.66; O, 6.66

Price and Availability

Size Price Availability Quantity
250mg USD 350.00 2 Weeks
500mg USD 550.00 2 Weeks
1g USD 850.00 2 Weeks
2g USD 1,250.00 2 Weeks
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Related CAS #
No Data
Synonym
Ameltolide;
IUPAC/Chemical Name
2',6'-Benzoxylidide, 4-amino-
InChi Key
HZIWGOAXOBPQGY-UHFFFAOYSA-N
InChi Code
InChI=1S/C15H16N2O/c1-10-4-3-5-11(2)14(10)17-15(18)12-6-8-13(16)9-7-12/h3-9H,16H2,1-2H3,(H,17,18)
SMILES Code
O=C(NC1=C(C)C=CC=C1C)C2=CC=C(N)C=C2
Appearance
Solid powder
Purity
>95% (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
>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 240.31 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: Taghizad S, Behbahaninia K, Jahromy MH, Davood A. Pyrrolopyridine and Isoindole as Potential Anticonvulsant Agents: Design, Synthesis, and Pharmacological Evaluation. Curr Comput Aided Drug Des. 2022;18(3):159-167. doi: 10.2174/1573409918666220512000247. PMID: 35546772. 2: Iman M, Fakhari S, Jahanpanah M, Naderi N, Davood A. Design and Synthesis of 4-flurophthalimides as potential anticonvulsant agents. Iran J Pharm Res. 2018 Summer;17(3):896-905. PMID: 30127813; PMCID: PMC6094442. 3: Iman M, Saadabadi A, Davood A, Shafaroodi H, Nikbakht A, Ansari A, Abedini M. Docking, Synthesis and Anticonvulsant Activity of N-substituted Isoindoline-1,3-dione. Iran J Pharm Res. 2017 Spring;16(2):586-595. PMID: 29721024; PMCID: PMC5603866. 4: Iman M, Saadabadi A, Davood A. Docking studies of phthalimide pharmacophore as a sodium channel blocker. Iran J Basic Med Sci. 2013 Sep;16(9):1016-21. PMID: 24171082; PMCID: PMC3804840. 5: Territo PR, Shannon HE, Newhall K, Barnhart SD, Peters SC, Engleking DR, Bin T, Burnett TJ, Rodewald JM, Abdul-Karim B, Freise KJ. Nonlinear mixed effects pharmacokinetic/pharmacodynamic analysis of the anticonvulsant ameltolide (LY201116) in a canine seizure model. J Vet Pharmacol Ther. 2008 Dec;31(6):562-70. doi: 10.1111/j.1365-2885.2008.00995.x. PMID: 19000280. 6: Yogeeswari P, Sriram D, Sahitya P, Ragavendran JV, Ranganadh V. Synthesis and anticonvulsant activity of 4-(2-(2,6-dimethylphenylamino)-2-oxoethylamino)-N-(substituted)butanamides: a pharmacophoric hybrid approach. Bioorg Med Chem Lett. 2007 Jul 1;17(13):3712-5. doi: 10.1016/j.bmcl.2007.04.032. Epub 2007 Apr 13. PMID: 17481896. 7: Yogeeswari P, Sriram D, Thirumurugan R, Raghavendran JV, Sudhan K, Pavana RK, Stables J. Discovery of N-(2,6-dimethylphenyl)-substituted semicarbazones as anticonvulsants: hybrid pharmacophore-based design. J Med Chem. 2005 Oct 6;48(20):6202-11. doi: 10.1021/jm050283b. PMID: 16190747. 8: Askwith CC, Wemmie JA, Price MP, Rokhlina T, Welsh MJ. Acid-sensing ion channel 2 (ASIC2) modulates ASIC1 H+-activated currents in hippocampal neurons. J Biol Chem. 2004 Apr 30;279(18):18296-305. doi: 10.1074/jbc.M312145200. Epub 2004 Feb 11. PMID: 14960591. 9: Bourhim M, Poupaert JH, Stables JP, Vallée L, Vamecq J. Design, anticonvulsive and neurotoxic properties of retrobenzamides. N-(Nitrophenyl)benzamides and N-(aminophenyl)benzamides. Arzneimittelforschung. 1999 Feb;49(2):81-7. doi: 10.1055/s-0031-1300365. PMID: 10083974. 10: Vamecq J, Lambert D, Poupaert JH, Masereel B, Stables JP. Anticonvulsant activity and interactions with neuronal voltage-dependent sodium channel of analogues of ameltolide. J Med Chem. 1998 Aug 27;41(18):3307-13. doi: 10.1021/jm9608772. PMID: 9719582. 11: Kanyonyo MR, Poupaert JH, Lambert DM. Anticonvulsant profile of 4-amino-(2-methyl-4-aminophenyl)benzamide in mice and rats. Pharmacol Toxicol. 1998 Jan;82(1):47-50. doi: 10.1111/j.1600-0773.1998.tb01397.x. PMID: 9527647. 12: Bourhim M, Kanyonyo MD, Lambert DM, Poupaert JH, Stables JP, Vamecq J. Conception rationnelle, synthèse et évaluation d'agents anticonvulsivants originaux à potentialité phénytoïnergique. La série des rétrobenzamides: les N-(nitrophényl) benzamides et les N-(aminophényl)benzamides [Rational conception, synthesis and evaluation of phenytoinergic potential anticonvulsants. A series ofretrobenzamides: N-(nitrophenyl) benzamides and N-(aminophenyl) benzamides]. J Pharm Belg. 1997 Sep-Oct;52(5):181-9. French. PMID: 9432526. 13: Van Derpoorten K, Balzarini J, De Clercq E, Poupaert JH. Anti-HIV activity of N-1-adamantyl-4-aminophthalimide. Biomed Pharmacother. 1997;51(10):464-8. doi: 10.1016/s0753-3322(97)82327-x. PMID: 9863507. 14: Diouf O, Bourhim M, Lambert DM, Poupaert JH, Stables JP, Vamecq J. Anticonvulsant and neurotoxicological properties of 4-amino-N-(2-ethylphenyl)benzamide, a potent ameltolide analogue. Biomed Pharmacother. 1997;51(3):131-6. doi: 10.1016/s0753-3322(97)86911-9. PMID: 9181049. 15: Engelhardt JA, Parli CJ, Kovach PM, Shoufler JR, Emmerson JL, Leander JD. Subchronic toxicity, metabolism, and pharmacokinetics of the aminobenzamide anticonvulsant ameltolide (LY201116) in rhesus monkeys. Fundam Appl Toxicol. 1992 Aug;19(2):197-201. doi: 10.1016/0272-0590(92)90151-7. PMID: 1516775. 16: Leander JD. Interaction of the anticonvulsant ameltolide with standard anticonvulsants. Epilepsia. 1992 Jul-Aug;33(4):705-11. doi: 10.1111/j.1528-1157.1992.tb02351.x. PMID: 1628588. 17: Leander JD, Parli CJ, Potts B, Lodge D. Relation of plasma and brain concentrations of the anticonvulsant ameltolide to its pharmacologic effects. Epilepsia. 1992 Jul-Aug;33(4):696-704. doi: 10.1111/j.1528-1157.1992.tb02350.x. PMID: 1628587. 18: Leander JD. Fluoxetine, a selective serotonin-uptake inhibitor, enhances the anticonvulsant effects of phenytoin, carbamazepine, and ameltolide (LY201116). Epilepsia. 1992 May-Jun;33(3):573-6. doi: 10.1111/j.1528-1157.1992.tb01712.x. PMID: 1534297. 19: Pohland RC, Vavrek MT. Ameltolide. II: Placental transfer of radiocarbon following the oral administration of a novel anticonvulsant in rats. Teratology. 1991 Jul;44(1):45-9. doi: 10.1002/tera.1420440108. PMID: 1957262. 20: Higdon GL, McKinley ER, Markham JK. Ameltolide. I: Developmental toxicology studies of a novel anticonvulsant. Teratology. 1991 Jul;44(1):37-44. doi: 10.1002/tera.1420440107. PMID: 1957261.