WARNING: This product is for research use only, not for human or veterinary use.
Hodoodo CAT#: H318891
CAS#: 97240-79-4 (free base)
Description: Topiramate (brand name Topamax) is an anticonvulsant (antiepilepsy) drug. In late 2012, topiramate was approved by the United States Food and Drug Administration (FDA) in combination with phentermine for weight loss. The drug had previously been used off-label for this purpose. Topiramate is used to treat epilepsy in children and adults, and it was originally used as an anticonvulsant. In children, it is indicated for the treatment of Lennox-Gastaut syndrome, a disorder that causes seizures and developmental delay.
Hodoodo Cat#: H318891
Name: Topiramate
CAS#: 97240-79-4 (free base)
Chemical Formula: C12H21NO8S
Exact Mass: 339.10
Molecular Weight: 339.359
Elemental Analysis: C, 42.47; H, 6.24; N, 4.13; O, 37.72; S, 9.45
Related CAS #: 488127-53-3 (lithium) 97240-79-4 (free base)
Synonym: HSDB-7531; HSDB 7531; HSDB7531; Topiramate; Tipiramato; Topax
IUPAC/Chemical Name: ((3aS,5aR,8aR,8bS)-2,2,7,7-tetramethyltetrahydro-3aH-bis([1,3]dioxolo)[4,5-b:4',5'-d]pyran-3a-yl)methyl sulfamate
InChi Key: KJADKKWYZYXHBB-XBWDGYHZSA-N
InChi Code: InChI=1S/C12H21NO8S/c1-10(2)18-7-5-16-12(6-17-22(13,14)15)9(8(7)19-10)20-11(3,4)21-12/h7-9H,5-6H2,1-4H3,(H2,13,14,15)/t7-,8-,9+,12+/m1/s1
SMILES Code: CC1(O[C@H]([C@@H](CO[C@@]2(COS(=O)(N)=O)O3)O1)[C@@H]2OC3(C)C)C
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:
| Biological target: | Topiramate is a GluR5 receptor antagonist. |
| In vitro activity: | Indeed, this study found that SOX9 expression is increased following topiramate treatment (Fig 3A and 3B), which is consistent with a role for TGFβ1 in stabilizing SOX9 protein. Expression of another SOXE transcription factor group member associated with orofacial clefts, SOX10, is not altered upon topiramate treatment (Fig 3A and 3C), showing specificity for SOX9 upregulation. These results with topiramate suggest that TGFβ1-mediated altered expression of SOX9 underlies the teratogenicity of this antiepileptic drug. Reference: PLoS One. 2021; 16(2): e0246989. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7880431/ |
| In vivo activity: | AAA (Abdominal Aortic Aneurysm) incidence had a dose-dependent decline after topiramate treatment. In the high-dose group (6 mg/day per mouse), the AAA incidence was significantly reduced from 75% (control group, 12 of 16) to 37.5% (6 of 16). The AAA incidence in the low-dose group (3 mg/day per mouse) was higher than that in the high-dose group (50%, 8 of 16) (Figure 3C). In accordance to the reduced AAA incidence, high-dose topiramate treatment elevated the survival ratio from 62.5% to 81.25% compared with the control group (Figure 3E). These results indicate that topiramate effectively ameliorates AngII-induced AAA formation in mice. Studies have shown topiramate lowed blood pressure in some degree. Reference: Front Pharmacol. 2020; 11: 565461. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7485436/ |
| Solvent | Max Conc. mg/mL | Max Conc. mM | |
|---|---|---|---|
| Solubility | |||
| DMSO | 54.2 | 159.83 | |
| DMF | 25.0 | 73.67 | |
| Ethanol | 40.7 | 119.78 | |
| PBS (pH 7.2) | 0.2 | 0.44 | |
| Water | 4.0 | 11.79 |
The following data is based on the product molecular weight 339.36 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: | 1. Rafi SK, Goering JP, Olm-Shipman AJ, Hipp LA, Ernst NJ, Wilson NR, Hall EG, Gunewardena S, Saadi I. Anti-epileptic drug topiramate upregulates TGFβ1 and SOX9 expression in primary embryonic palatal mesenchyme cells: Implications for teratogenicity. PLoS One. 2021 Feb 12;16(2):e0246989. doi: 10.1371/journal.pone.0246989. PMID: 33577554; PMCID: PMC7880431. 2. Xu G, Fang Z, Clark LH, Sun W, Yin Y, Zhang R, Sullivan SA, Tran AQ, Kong W, Wang J, Zhou C, Bae-Jump VL. Topiramate exhibits anti-tumorigenic and metastatic effects in ovarian cancer cells. Am J Transl Res. 2018 Jun 15;10(6):1663-1676. PMID: 30018708; PMCID: PMC6038080. 3. Chen X, Li Y, Xiao J, Zhang H, Yang C, Wei Z, Chen W, Du X, Liu J. Modulating Neuro-Immune-Induced Macrophage Polarization With Topiramate Attenuates Experimental Abdominal Aortic Aneurysm. Front Pharmacol. 2020 Aug 28;11:565461. doi: 10.3389/fphar.2020.565461. PMID: 32982758; PMCID: PMC7485436. 4. Chen C, Lang S, Xu G, Liu X, Zuo P. Effects of topiramate on seizure susceptibility in kainate-kindled rats: involvement of peripheral-type benzodiazepine receptors. Seizure. 2008 Jun;17(4):358-63. doi: 10.1016/j.seizure.2007.11.021. Epub 2007 Dec 27. PMID: 18164215. |
| In vitro protocol: | 1. Rafi SK, Goering JP, Olm-Shipman AJ, Hipp LA, Ernst NJ, Wilson NR, Hall EG, Gunewardena S, Saadi I. Anti-epileptic drug topiramate upregulates TGFβ1 and SOX9 expression in primary embryonic palatal mesenchyme cells: Implications for teratogenicity. PLoS One. 2021 Feb 12;16(2):e0246989. doi: 10.1371/journal.pone.0246989. PMID: 33577554; PMCID: PMC7880431. 2. Xu G, Fang Z, Clark LH, Sun W, Yin Y, Zhang R, Sullivan SA, Tran AQ, Kong W, Wang J, Zhou C, Bae-Jump VL. Topiramate exhibits anti-tumorigenic and metastatic effects in ovarian cancer cells. Am J Transl Res. 2018 Jun 15;10(6):1663-1676. PMID: 30018708; PMCID: PMC6038080. |
| In vivo protocol: | 1. Chen X, Li Y, Xiao J, Zhang H, Yang C, Wei Z, Chen W, Du X, Liu J. Modulating Neuro-Immune-Induced Macrophage Polarization With Topiramate Attenuates Experimental Abdominal Aortic Aneurysm. Front Pharmacol. 2020 Aug 28;11:565461. doi: 10.3389/fphar.2020.565461. PMID: 32982758; PMCID: PMC7485436. 2. Chen C, Lang S, Xu G, Liu X, Zuo P. Effects of topiramate on seizure susceptibility in kainate-kindled rats: involvement of peripheral-type benzodiazepine receptors. Seizure. 2008 Jun;17(4):358-63. doi: 10.1016/j.seizure.2007.11.021. Epub 2007 Dec 27. PMID: 18164215. |
1: Singh M, Keer D, Klimas J, Wood E, Werb D. Topiramate for Cocaine Dependence: A Systematic Review and Meta-Analysis of Randomized Control Trials. Addiction. 2016 Jan 30. doi: 10.1111/add.13328. [Epub ahead of print] Review. PubMed PMID: 26826006.
2: Liu J, Wang LN, Wang YP. Topiramate monotherapy for juvenile myoclonic epilepsy. Cochrane Database Syst Rev. 2015 Dec 23;12:CD010008. doi: 10.1002/14651858.CD010008.pub2. Review. PubMed PMID: 26695884.
3: Donegan S, Dixon P, Hemming K, Tudur-Smith C, Marson A. A systematic review of placebo-controlled trials of topiramate: How useful is a multiple-indications review for evaluating the adverse events of an antiepileptic drug? Epilepsia. 2015 Dec;56(12):1910-20. doi: 10.1111/epi.13209. Epub 2015 Oct 8. Review. PubMed PMID: 26662191.
4: Alfaris N, Minnick AM, Hopkins CM, Berkowitz RI, Wadden TA. Combination phentermine and topiramate extended release in the management of obesity. Expert Opin Pharmacother. 2015 Jun;16(8):1263-74. doi: 10.1517/14656566.2015.1041505. Review. PubMed PMID: 25958964.
5: Chung SS. A review of the efficacy and safety of extended-release topiramate in the adjunctive treatment for refractory partial-onset seizures. Ther Adv Neurol Disord. 2015 May;8(3):131-6. doi: 10.1177/1756285615578406. Review. PubMed PMID: 25941540; PubMed Central PMCID: PMC4409552.
6: Alsaad AM, Chaudhry SA, Koren G. First trimester exposure to topiramate and the risk of oral clefts in the offspring: A systematic review and meta-analysis. Reprod Toxicol. 2015 Jun;53:45-50. doi: 10.1016/j.reprotox.2015.03.003. Epub 2015 Mar 20. Review. PubMed PMID: 25797654.
7: Signorelli MS, Cinconze M, Nasca MR, Marino M, Martinotti G, Di Giannantonio M, Aguglia E. Can topiramate induce pruritus? A case report and review of literature. CNS Neurol Disord Drug Targets. 2015;14(3):309-12. Review. PubMed PMID: 25714980.
8: Yun SH, Lavin PJ, Schatz MP, Lesser RL. Topiramate-induced palinopsia: a case series and review of the literature. J Neuroophthalmol. 2015 Jun;35(2):148-51. doi: 10.1097/WNO.0000000000000216. Review. PubMed PMID: 25634739.
9: Jion YI, Raff A, Grosberg BM, Evans RW. The risk and management of kidney stones from the use of topiramate and zonisamide in migraine and idiopathic intracranial hypertension. Headache. 2015 Jan;55(1):161-6. doi: 10.1111/head.12480. Epub 2014 Dec 9. Review. PubMed PMID: 25486999.
10: Harshman H, Kovach F. Clinical inquiries: is immediate-release topiramate an effective treatment for adult obesity? J Fam Pract. 2014 Dec;63(12):745-6. Review. PubMed PMID: 25486315.
11: In brief: topiramate extended-release capsules (Qudexy XR). Med Lett Drugs Ther. 2014 Dec 8;56(1457):e126. Review. PubMed PMID: 25461233.
12: Chung S. USL255 extended-release topiramate for the treatment of epilepsy. Expert Rev Neurother. 2014 Oct;14(10):1127-37. doi: 10.1586/14737175.2014.958470. Epub 2014 Sep 13. Review. PubMed PMID: 25220748.
13: Marmura MJ. Safety of topiramate for treating migraines. Expert Opin Drug Saf. 2014 Sep;13(9):1241-7. doi: 10.1517/14740338.2014.934669. Epub 2014 Aug 6. Review. PubMed PMID: 25096056.
14: Cohen J, Dervaux A, Laqueille X. [Topiramate in substance-related and addictive disorders]. Presse Med. 2014 Sep;43(9):892-901. doi: 10.1016/j.lpm.2014.02.030. Epub 2014 Jul 11. Review. French. PubMed PMID: 25027463.
15: Rapoport Y, Benegas N, Kuchtey RW, Joos KM. Acute myopia and angle closure glaucoma from topiramate in a seven-year-old: a case report and review of the literature. BMC Pediatr. 2014 Apr 9;14:96. doi: 10.1186/1471-2431-14-96. Review. PubMed PMID: 24712825; PubMed Central PMCID: PMC3991910.
16: Xiong GL, Gadde KM. Combination phentermine/topiramate for obesity treatment in primary care: a review. Postgrad Med. 2014 Mar;126(2):110-6. doi: 10.3810/pgm.2014.03.2746. Review. PubMed PMID: 24685974.
17: Jordan J, Astrup A, Engeli S, Narkiewicz K, Day WW, Finer N. Cardiovascular effects of phentermine and topiramate: a new drug combination for the treatment of obesity. J Hypertens. 2014 Jun;32(6):1178-88. doi: 10.1097/HJH.0000000000000145. Review. PubMed PMID: 24621808; PubMed Central PMCID: PMC4011567.
18: Pulman J, Jette N, Dykeman J, Hemming K, Hutton JL, Marson AG. Topiramate add-on for drug-resistant partial epilepsy. Cochrane Database Syst Rev. 2014 Feb 25;2:CD001417. doi: 10.1002/14651858.CD001417.pub3. Review. PubMed PMID: 24570033.
19: Deaton TL, Mauro LS. Topiramate for migraine prophylaxis in pediatric patients. Ann Pharmacother. 2014 May;48(5):638-43. doi: 10.1177/1060028014521128. Epub 2014 Feb 24. Review. PubMed PMID: 24566461.
20: Sweeting AN, Tabet E, Caterson ID, Markovic TP. Management of obesity and cardiometabolic risk - role of phentermine/extended release topiramate. Diabetes Metab Syndr Obes. 2014 Feb 12;7:35-44. doi: 10.2147/DMSO.S38979. eCollection 2014. Review. PubMed PMID: 24550678; PubMed Central PMCID: PMC3926768.
