Raxatrigine free base | Vixotrigine | GSK1014802 | CNV-1014802 | CAS#934240-30-9 | 934240-31-0

MedKoo Cat#: 510347 | Name: Raxatrigine free base

Description:

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

Raxatrigine, also known as vixotrigine, GSK1014802, and CNV1014802, is a small molecule state-dependent sodium channel blocker; Nav1.7 sodium channel inhibitor.

Chemical Structure

Raxatrigine free base

CAS#934240-30-9 (free base)

Theoretical Analysis

MedKoo Cat#: 510347

Name: Raxatrigine free base

CAS#: 934240-30-9 (free base)

Chemical Formula: C18H19FN2O2

Exact Mass: 314.1431

Molecular Weight: 314.36

Elemental Analysis: C, 68.77; H, 6.09; F, 6.04; N, 8.91; O, 10.18

Price and Availability

Size	Price	Availability
25mg	USD 750.00	2 weeks
50mg	USD 1,250.00	2 weeks
100mg	USD 1,950.00	2 weeks
1g	USD 4,850.00	2 weeks

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Related CAS #

934240-31-0 (HCl) 934240-30-9 (free base) 934240-35-4 (mesylate)

Synonym

GSK1014802; GSK 1014802; GSK-1014802; CNV1014802; CNV-1014802; CNV 1014802; Raxatrigine; Raxatrigine free base; Vixotrigine;

IUPAC/Chemical Name

(2S,5R)-5-(4-((2-fluorobenzyl)oxy)phenyl)pyrrolidine-2-carboxamide

InChi Key

JESCETIFNOFKEU-SJORKVTESA-N

InChi Code

InChI=1S/C18H19FN2O2/c19-15-4-2-1-3-13(15)11-23-14-7-5-12(6-8-14)16-9-10-17(21-16)18(20)22/h1-8,16-17,21H,9-11H2,(H2,20,22)/t16-,17+/m1/s1

SMILES Code

O=C(N)[C@H]1N[C@@H](C2=CC=C(OCC3=CC=CC=C3F)C=C2)CC1

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

>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

Related CAS# CAS#934240-31-0 ( Raxatrigine hydrochloride) CAS#934240-30-9 ( Raxatrigine free).

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Raxatrigine is a sodium channel blocker and a Nav1.7 sodium channel inhibitor.

In vitro activity:

This study demonstrates that raxatrigine enhances the inactivation but does not reduce the activation of Nav1.7 channels. Reference: Acta Pharmacol Sin. 2018 Apr;39(4):587-596. https://pubmed.ncbi.nlm.nih.gov/29094728/

In vivo activity:

Orally administered raxatrigine for neuropathic pain is well-tolerated when administered as single doses up to 825 mg and multiple doses up to 450 mg twice daily. Reference: Clin Transl Sci. 2021 Jul;14(4):1272-1279. https://pubmed.ncbi.nlm.nih.gov/33278330/

	Solvent	mg/mL	mM
Solubility
	DMSO	83.0	264.04

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 314.36 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. Zheng YM, Wang WF, Li YF, Yu Y, Gao ZB. Enhancing inactivation rather than reducing activation of Nav1.7 channels by a clinically effective analgesic CNV1014802. Acta Pharmacol Sin. 2018 Apr;39(4):587-596. doi: 10.1038/aps.2017.151. Epub 2017 Nov 2. PMID: 29094728; PMCID: PMC5888685. 2. Naik H, Steiner DJ, Versavel M, Palmer J, Fong R. Safety, Tolerability and Pharmacokinetics of Single and Repeat Doses of Vixotrigine in Healthy Volunteers. Clin Transl Sci. 2021 Jul;14(4):1272-1279. doi: 10.1111/cts.12935. Epub 2020 Dec 13. PMID: 33278330; PMCID: PMC8301589. 3. Witty DR, Alvaro G, Derjean D, Giblin GMP, Gunn K, Large C, Macpherson DT, Morisset V, Owen D, Palmer J, Rugiero F, Tate S, Hinckley CA, Naik H. Discovery of Vixotrigine: A Novel Use-Dependent Sodium Channel Blocker for the Treatment of Trigeminal Neuralgia. ACS Med Chem Lett. 2020 Jul 16;11(9):1678-1687. doi: 10.1021/acsmedchemlett.0c00263. PMID: 32945812; PMCID: PMC7488392.

In vitro protocol:

In vivo protocol:

1. Naik H, Steiner DJ, Versavel M, Palmer J, Fong R. Safety, Tolerability and Pharmacokinetics of Single and Repeat Doses of Vixotrigine in Healthy Volunteers. Clin Transl Sci. 2021 Jul;14(4):1272-1279. doi: 10.1111/cts.12935. Epub 2020 Dec 13. PMID: 33278330; PMCID: PMC8301589. 2. Witty DR, Alvaro G, Derjean D, Giblin GMP, Gunn K, Large C, Macpherson DT, Morisset V, Owen D, Palmer J, Rugiero F, Tate S, Hinckley CA, Naik H. Discovery of Vixotrigine: A Novel Use-Dependent Sodium Channel Blocker for the Treatment of Trigeminal Neuralgia. ACS Med Chem Lett. 2020 Jul 16;11(9):1678-1687. doi: 10.1021/acsmedchemlett.0c00263. PMID: 32945812; PMCID: PMC7488392.

1: Pergolizzi JV Jr, LeQuang JA, El-Tallawy SN, Wagner M, Ahmed RS, Varrassi G. An update on pharmacotherapy for trigeminal neuralgia. Expert Rev Neurother. 2024 Aug;24(8):773-786. doi: 10.1080/14737175.2024.2365946. Epub 2024 Jun 13. PMID: 38870050. 2: Rana MH, Khan AAG, Khalid I, Ishfaq M, Javali MA, Baig FAH, Kota MZ, Khader MA, Hameed MS, Shaik S, Das G. Therapeutic Approach for Trigeminal Neuralgia: A Systematic Review. Biomedicines. 2023 Sep 22;11(10):2606. doi: 10.3390/biomedicines11102606. PMID: 37892981; PMCID: PMC10604820. 3: Wu Q, Huang J, Fan X, Wang K, Jin X, Huang G, Li J, Pan X, Yan N. Structural mapping of Nav1.7 antagonists. Nat Commun. 2023 Jun 3;14(1):3224. doi: 10.1038/s41467-023-38942-3. PMID: 37270609; PMCID: PMC10239435. 4: Faber CG, Attal N, Lauria G, Dworkin RH, Freeman R, Dawson KT, Finnigan H, Hajihosseini A, Naik H, Serenko M, Morris CJ, Kotecha M. Efficacy and safety of vixotrigine in idiopathic or diabetes-associated painful small fibre neuropathy (CONVEY): a phase 2 placebo-controlled enriched-enrolment randomised withdrawal study. EClinicalMedicine. 2023 Apr 27;59:101971. doi: 10.1016/j.eclinm.2023.101971. PMID: 37152360; PMCID: PMC10154969. 5: Zhao Y, Kotecha M, Finnigan H, Serenko M, Naik H. Evaluation of the Effect of Uridine Diphosphate-Glucuronosyltransferases (UGT) Inhibition by Valproic Acid on Vixotrigine Pharmacokinetics in Healthy Volunteers. Clin Drug Investig. 2022 Oct;42(10):829-837. doi: 10.1007/s40261-022-01194-y. Epub 2022 Aug 31. PMID: 36045316. 6: Pergolizzi JV Jr, Gharibo C, Magnusson P, Breve F, LeQuang JA, Varrassi G. Pharmacotherapeutic management of trigeminal neuropathic pain: an update. Expert Opin Pharmacother. 2022 Jul;23(10):1155-1164. doi: 10.1080/14656566.2022.2087507. Epub 2022 Jun 23. PMID: 35695796. 7: Alles SRA, Smith PA. Peripheral Voltage-Gated Cation Channels in Neuropathic Pain and Their Potential as Therapeutic Targets. Front Pain Res (Lausanne). 2021 Dec 13;2:750583. doi: 10.3389/fpain.2021.750583. PMID: 35295464; PMCID: PMC8915663. 8: Johnson JL, Huang J, Rooney M, Gu C. Optimal pH 8.5 to 9 for the hydrolysis of vixotrigine and other basic substrates of carboxylesterase-1 in human liver microsomes. Xenobiotica. 2022 Feb;52(2):105-112. doi: 10.1080/00498254.2021.2018629. Epub 2022 Mar 16. PMID: 34904522. 9: Khadilkar SV, Patil VA. Medical Management of Trigeminal Neuralgia. Neurol India. 2021 Mar-Apr;69(Supplement):S199-S205. doi: 10.4103/0028-3886.315996. PMID: 34003166. 10: Naik H, Zhao Y, Forrestal F, Cleall S, Bockbrader H, Chapel S. Population Pharmacokinetics of Vixotrigine in Healthy Volunteers and Subjects with Trigeminal Neuralgia, Painful Lumbosacral Radiculopathy and Erythromelalgia. Eur J Drug Metab Pharmacokinet. 2021 May;46(3):395-404. doi: 10.1007/s13318-021-00678-0. PMID: 33782834. 11: Hinckley CA, Kuryshev Y, Sers A, Barre A, Buisson B, Naik H, Hajos M. Characterization of Vixotrigine, a Broad-Spectrum Voltage-Gated Sodium Channel Blocker. Mol Pharmacol. 2021 Jan;99(1):49-59. doi: 10.1124/molpharm.120.000079. PMID: 33298520. 12: Naik H, Steiner DJ, Versavel M, Palmer J, Fong R. Safety, Tolerability and Pharmacokinetics of Single and Repeat Doses of Vixotrigine in Healthy Volunteers. Clin Transl Sci. 2021 Jul;14(4):1272-1279. doi: 10.1111/cts.12935. Epub 2020 Dec 13. PMID: 33278330; PMCID: PMC8301589. 13: Witty DR, Alvaro G, Derjean D, Giblin GMP, Gunn K, Large C, Macpherson DT, Morisset V, Owen D, Palmer J, Rugiero F, Tate S, Hinckley CA, Naik H. Discovery of Vixotrigine: A Novel Use-Dependent Sodium Channel Blocker for the Treatment of Trigeminal Neuralgia. ACS Med Chem Lett. 2020 Jul 16;11(9):1678-1687. doi: 10.1021/acsmedchemlett.0c00263. PMID: 32945812; PMCID: PMC7488392. 14: Kotecha M, Cheshire WP, Finnigan H, Giblin K, Naik H, Palmer J, Tate S, Zakrzewska JM. Design of Phase 3 Studies Evaluating Vixotrigine for Treatment of Trigeminal Neuralgia. J Pain Res. 2020 Jul 1;13:1601-1609. doi: 10.2147/JPR.S247182. PMID: 32669869; PMCID: PMC7335847. 15: Zhao Y, Versavel M, Tidemann-Miller B, Christmann R, Naik H. Evaluation of the Potential Pharmacokinetic Interactions Between Vixotrigine and an Oral Contraceptive. Clin Drug Investig. 2020 Aug;40(8):737-746. doi: 10.1007/s40261-020-00931-5. PMID: 32564301; PMCID: PMC7359159. 16: Gambeta E, Chichorro JG, Zamponi GW. Trigeminal neuralgia: An overview from pathophysiology to pharmacological treatments. Mol Pain. 2020 Jan- Dec;16:1744806920901890. doi: 10.1177/1744806920901890. PMID: 31908187; PMCID: PMC6985973. 17: Dunbar J, Versavel M, Zhao Y, Tate S, Morisset V, Giblin GMP, Palmer J, Tidemann-Miller B, Naik H. Evaluation of the Pharmacokinetic Interaction Between the Voltage- and Use-Dependent Nav1.7 Channel Blocker Vixotrigine and Carbamazepine in Healthy Volunteers. Clin Pharmacol Drug Dev. 2020 Jan;9(1):62-73. doi: 10.1002/cpdd.739. Epub 2019 Oct 24. PMID: 31650711. 18: Obermann M. Recent advances in understanding/managing trigeminal neuralgia. F1000Res. 2019 Apr 17;8:F1000 Faculty Rev-505. doi: 10.12688/f1000research.16092.1. PMID: 31069052; PMCID: PMC6480942. 19: Zakrzewska JM, Palmer J, Bendtsen L, Di Stefano G, Ettlin DA, Maarbjerg S, Obermann M, Morisset V, Steiner D, Tate S, Cruccu G. Challenges recruiting to a proof-of-concept pharmaceutical trial for a rare disease: the trigeminal neuralgia experience. Trials. 2018 Dec 27;19(1):704. doi: 10.1186/s13063-018-3045-1. PMID: 30587219; PMCID: PMC6307274. 20: Di Stefano G, Truini A, Cruccu G. Current and Innovative Pharmacological Options to Treat Typical and Atypical Trigeminal Neuralgia. 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