Levetiracetam | CAS#102767-28-2

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

MedKoo CAT#: 318094

CAS#: 102767-28-2

Description: Levetiracetam is a medication used to treat epilepsy. It is the S-enantiomer of etiracetam. Levetiracetam is used for partial onset, myoclonic, or tonic-clonic seizures.

Chemical Structure

Levetiracetam

CAS# 102767-28-2

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 318094
Name: Levetiracetam
CAS#: 102767-28-2
Chemical Formula: C8H14N2O2
Exact Mass: 170.11
Molecular Weight: 170.209
Elemental Analysis: C, 56.45; H, 8.29; N, 16.46; O, 18.80

Price and Availability

Size	Price	Availability
1g	USD 250	Ready to ship
5g	USD 450	2 Weeks
10g	USD 650	2 Weeks
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: Levetiracetam, Keppra, Etiracetam, UCB 6474

IUPAC/Chemical Name: (S)-2-(2-oxopyrrolidin-1-yl)butanamide

InChi Key: HPHUVLMMVZITSG-LURJTMIESA-N

InChi Code: InChI=1S/C8H14N2O2/c1-2-6(8(9)12)10-5-3-4-7(10)11/h6H,2-5H2,1H3,(H2,9,12)/t6-/m0/s1

SMILES Code: O=C(N)[C@H](CC)N1C(CCC1)=O

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:

Product Data:

Product Data

Certificate of Analysis:

View CoA: current batch, Lot#T8C12I07

Safety Data Sheet (SDS):

View Safety Data Sheet (SDS)

Instruction:

View handling instruction

Biological target:	Levetiracetam (UCB L059) is a selective M2 muscarinic acetylcholine receptors (mAChR) inhibitor.
In vitro activity:	MCs can release several soluble mediators by granule exocytosis in response to activation, this study tested whether levetiracetam hampered this function in BMMCs subjected to different stimuli. Notably, this drug significantly inhibited the release of beta-hexosaminidase in both IgE/Ag- and Ionomycin-activated BMMCs, in a concentration dependent manner (Figure 4B). Moreover, levetiracetam decreased the IgE/Ag crosslink-mediated release of newly formed lipid mediators as demonstrated by the reduced amounts of leukotrienes C4, D4, and E4 measured in cell supernatants. Reference: Front Immunol. 2021; 12: 622001. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7960782/
In vivo activity:	To evaluate the effect of LEV (Levetiracetam) on the surviving neurons and the functional state of the brain, the Morris water maze was used to assess learning and memory in the rats. The rats in the control group reached the hidden platform in a short time during training. In contrast, rats in the saline group showed obvious functional defects. The time required to reach the platform for LEV-treated rats was shorter than that in the saline group but not differ from that of the control group (Figure 4A). On day 14 after MACO (middle cerebral artery occlusion), the time the rats were able to stay on the accelerating rotarod was significantly shortened (Figure 4B). LEV treatment after ischemia effectively improved this motor function defect by prolonging the rotarod retention time. Reference: Front Pharmacol. 2021; 12: 638209. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8161206/

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. mM
Solubility
	DMSO	39.0	229.13
	DMF	20.0	117.50
	Ethanol	25.4	148.93
	PBS (pH 7.2)	10.0	58.75
	Water	45.3	266.38

Preparing Stock Solutions

The following data is based on the product molecular weight 170.21 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. Sulsenti R, Frossi B, Bongiovanni L, Cancila V, Ostano P, Fischetti I, Enriquez C, Guana F, Chiorino G, Tripodo C, Pucillo CE, Colombo MP, Jachetti E. Repurposing of the Antiepileptic Drug Levetiracetam to Restrain Neuroendocrine Prostate Cancer and Inhibit Mast Cell Support to Adenocarcinoma. Front Immunol. 2021 Mar 2;12:622001. doi: 10.3389/fimmu.2021.622001. PMID: 33737929; PMCID: PMC7960782. 2. Yao X, Yang W, Ren Z, Zhang H, Shi D, Li Y, Yu Z, Guo Q, Yang G, Gu Y, Zhao H, Ren K. Neuroprotective and Angiogenesis Effects of Levetiracetam Following Ischemic Stroke in Rats. Front Pharmacol. 2021 May 14;12:638209. doi: 10.3389/fphar.2021.638209. PMID: 34054520; PMCID: PMC8161206.
In vitro protocol:	1. Sulsenti R, Frossi B, Bongiovanni L, Cancila V, Ostano P, Fischetti I, Enriquez C, Guana F, Chiorino G, Tripodo C, Pucillo CE, Colombo MP, Jachetti E. Repurposing of the Antiepileptic Drug Levetiracetam to Restrain Neuroendocrine Prostate Cancer and Inhibit Mast Cell Support to Adenocarcinoma. Front Immunol. 2021 Mar 2;12:622001. doi: 10.3389/fimmu.2021.622001. PMID: 33737929; PMCID: PMC7960782.
In vivo protocol:	1. Yao X, Yang W, Ren Z, Zhang H, Shi D, Li Y, Yu Z, Guo Q, Yang G, Gu Y, Zhao H, Ren K. Neuroprotective and Angiogenesis Effects of Levetiracetam Following Ischemic Stroke in Rats. Front Pharmacol. 2021 May 14;12:638209. doi: 10.3389/fphar.2021.638209. PMID: 34054520; PMCID: PMC8161206.

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1: Pourzitaki C, Tsaousi G, Apostolidou E, Karakoulas K, Kouvelas D, Amaniti E. Efficacy and safety of prophylactic levetiracetam in supratentorial brain tumour surgery: a systematic review and meta-analysis. Br J Clin Pharmacol. 2016 Mar 5. doi: 10.1111/bcp.12926. [Epub ahead of print] Review. PubMed PMID: 26945547.

2: Yuan Y, Peizhi Z, Maling G, Wu L, Yunhe M, Xiang W, Qing M, Yanhui L, Ruofei L, Jiewen L. The efficacy of levetiracetam for patients with supratentorial brain tumors. J Clin Neurosci. 2015 Aug;22(8):1227-31. doi: 10.1016/j.jocn.2015.01.025. Epub 2015 Jun 6. Review. PubMed PMID: 26051171.

3: Mruk AL, Garlitz KL, Leung NR. Levetiracetam in neonatal seizures: a review. J Pediatr Pharmacol Ther. 2015 Mar-Apr;20(2):76-89. doi: 10.5863/1551-6776-20.2.76. Review. PubMed PMID: 25964725; PubMed Central PMCID: PMC4418685.

4: Lewis JC, Albertson TE, Walsh MJ. An 11-year review of levetiracetam ingestions in children less than 6 years of age. Clin Toxicol (Phila). 2014 Nov;52(9):964-8. doi: 10.3109/15563650.2014.965828. Epub 2014 Oct 6. Review. PubMed PMID: 25283254.

5: Halma E, de Louw AJ, Klinkenberg S, Aldenkamp AP, IJff DM, Majoie M. Behavioral side-effects of levetiracetam in children with epilepsy: a systematic review. Seizure. 2014 Oct;23(9):685-91. doi: 10.1016/j.seizure.2014.06.004. Epub 2014 Jun 12. Review. PubMed PMID: 24981629.

6: Mbizvo GK, Dixon P, Hutton JL, Marson AG. The adverse effects profile of levetiracetam in epilepsy: a more detailed look. Int J Neurosci. 2014 Sep;124(9):627-34. doi: 10.3109/00207454.2013.866951. Epub 2013 Dec 18. Review. PubMed PMID: 24256446.

7: Wiffen PJ, Derry S, Moore RA, Lunn MP. Levetiracetam for neuropathic pain in adults. Cochrane Database Syst Rev. 2014 Jul 7;7:CD010943. doi: 10.1002/14651858.CD010943.pub2. Review. PubMed PMID: 25000215.

8: Chaudhry SA, Jong G, Koren G. The fetal safety of Levetiracetam: a systematic review. Reprod Toxicol. 2014 Jul;46:40-5. doi: 10.1016/j.reprotox.2014.02.004. Epub 2014 Mar 3. Review. PubMed PMID: 24602560.

9: Deshpande LS, Delorenzo RJ. Mechanisms of levetiracetam in the control of status epilepticus and epilepsy. Front Neurol. 2014 Jan 31;5:11. doi: 10.3389/fneur.2014.00011. eCollection 2014. Review. PubMed PMID: 24550884; PubMed Central PMCID: PMC3907711.

10: Wright C, Downing J, Mungall D, Khan O, Williams A, Fonkem E, Garrett D, Aceves J, Kirmani B. Clinical pharmacology and pharmacokinetics of levetiracetam. Front Neurol. 2013 Dec 4;4:192. doi: 10.3389/fneur.2013.00192. Review. PubMed PMID: 24363651; PubMed Central PMCID: PMC3850169.

11: Benge JF, Phenis RA, Bernett A, Cruz-Laureano D, Kirmani BF. Neurobehavioral effects of levetiracetam in patients with traumatic brain injury. Front Neurol. 2013 Dec 2;4:195. doi: 10.3389/fneur.2013.00195. Review. PubMed PMID: 24348459; PubMed Central PMCID: PMC3845013.

12: Shetty AK. Prospects of levetiracetam as a neuroprotective drug against status epilepticus, traumatic brain injury, and stroke. Front Neurol. 2013 Nov 4;4:172. doi: 10.3389/fneur.2013.00172. Review. PubMed PMID: 24204362; PubMed Central PMCID: PMC3816384.

13: Kirmani BF, Mungall D, Ling G. Role of intravenous levetiracetam in seizure prophylaxis of severe traumatic brain injury patients. Front Neurol. 2013 Nov 1;4:170. doi: 10.3389/fneur.2013.00170. Review. PubMed PMID: 24198810; PubMed Central PMCID: PMC3814517.

14: Fonkem E, Bricker P, Mungall D, Aceves J, Ebwe E, Tang W, Kirmani B. The role of levetiracetam in treatment of seizures in brain tumor patients. Front Neurol. 2013 Oct 7;4:153. doi: 10.3389/fneur.2013.00153. Review. PubMed PMID: 24109474; PubMed Central PMCID: PMC3791389.

15: Larkin TM, Cohen-Oram AN, Catalano G, Catalano MC. Overdose with levetiracetam: a case report and review of the literature. J Clin Pharm Ther. 2013 Feb;38(1):68-70. doi: 10.1111/j.1365-2710.2012.01361.x. Epub 2012 Jun 21. Review. PubMed PMID: 22725831.

16: Rösche J, Pohley I, Rantsch K, Walter U, Benecke R. [Experience with levetiracetam in the treatment of status epilepticus]. Fortschr Neurol Psychiatr. 2013 Jan;81(1):21-7. doi: 10.1055/s-0032-1312951. Epub 2012 Aug 13. Review. German. PubMed PMID: 22890440.

17: Mbizvo GK, Dixon P, Hutton JL, Marson AG. Levetiracetam add-on for drug-resistant focal epilepsy: an updated Cochrane Review. Cochrane Database Syst Rev. 2012 Sep 12;9:CD001901. doi: 10.1002/14651858.CD001901.pub2. Review. PubMed PMID: 22972056.

18: Babtain FA. Levetiracetam may worsen myoclonus in patients with juvenile myoclonic epilepsy: case reports. Clin Neuropharmacol. 2012 Jul-Aug;35(4):201-2. doi: 10.1097/WNF.0b013e31825eed8c. Review. PubMed PMID: 22805231.

19: Zelano J, Kumlien E. Levetiracetam as alternative stage two antiepileptic drug in status epilepticus: a systematic review. Seizure. 2012 May;21(4):233-6. doi: 10.1016/j.seizure.2012.01.008. Epub 2012 Feb 8. Review. PubMed PMID: 22321334.

20: Lyseng-Williamson KA. Spotlight on levetiracetam in epilepsy. CNS Drugs. 2011 Oct 1;25(10):901-5. doi: 10.2165/11208340-000000000-00000. Review. PubMed PMID: 21936590.

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