Behaviour of Tetrabenazine in Acid Medium: Reassessment and Impact on Formulation.

LC-MS acid medium degradation impurities deuterated tetrabenazine deuteration orodispersible film stability synthesis tetrabenazine

Journal

Pharmaceutics
ISSN: 1999-4923
Titre abrégé: Pharmaceutics
Pays: Switzerland
ID NLM: 101534003

Informations de publication

Date de publication:
20 Jan 2019
Historique:
received: 14 12 2018
revised: 16 01 2019
accepted: 17 01 2019
entrez: 24 1 2019
pubmed: 24 1 2019
medline: 24 1 2019
Statut: epublish

Résumé

Thorough studies of previous analytical stress data of tetrabenazine, a dopamine depleting agent, showed a potential susceptibility to acidic conditions. Hence, the behavior of tetrabenazine acidic solutions was studied by LC-MS and NMR spectroscopy. Reverse-phase LC-MS analysis of tetrabenazine acidic aqueous solutions consistently showed a main lipophilic impurity in a proportion of 15 to 20%. NMR spectroscopy studies did not allow to completely ascertain its structure. However, we hypothesize an interconversion of

Identifiants

pubmed: 30669539
pii: pharmaceutics11010044
doi: 10.3390/pharmaceutics11010044
pmc: PMC6359103
pii:
doi:

Types de publication

Journal Article

Langues

eng

Déclaration de conflit d'intérêts

The authors declare no conflict of interest.

Références

J Org Chem. 2000 Sep 8;65(18):5739-44
pubmed: 10970318
J Pharm Sci. 2009 Dec;98(12):4711-23
pubmed: 19462469
J Control Release. 2009 Oct 15;139(2):94-107
pubmed: 19559740
Clin Ther. 2012 Jul;34(7):1487-504
pubmed: 22749259
Curr Drug Deliv. 2013 Feb;10(1):96-108
pubmed: 22920576
Int J Pharm Investig. 2013 Apr;3(2):67-76
pubmed: 24015378
Int J Pharm. 2013 Nov 30;457(1):310-22
pubmed: 24070789
J Pharm Biomed Anal. 2014 Mar;91:138-43
pubmed: 24457996
Eur J Pharm Sci. 2015 Apr 25;71:12-24
pubmed: 25686597
J Psychosoc Nurs Ment Health Serv. 2015 Sep;53(9):13-6
pubmed: 26325169
Nat Rev Drug Discov. 2016 Apr;15(4):219-21
pubmed: 27032821
J Pharm Pharmacol. 2017 May;69(5):582-592
pubmed: 27671542
Ann Neurosci. 2016 Sep;23(3):176-185
pubmed: 27721587
Expert Opin Investig Drugs. 2017 Feb;26(2):175-185
pubmed: 27927041
Int J Pharm. 2017 Feb 25;518(1-2):242-252
pubmed: 28007543
Drugs Today (Barc). 2017 Feb;53(2):89-102
pubmed: 28387387
Mov Disord Clin Pract. 2017 Jul-Aug;4(4):582-585
pubmed: 28920068
J Comp Eff Res. 2018 Feb;7(2):135-148
pubmed: 28965423
Expert Rev Neurother. 2017 Dec;17(12):1135-1144
pubmed: 28971695
Int J Clin Pract. 2017 Nov;71(11):null
pubmed: 29024264
Expert Rev Clin Pharmacol. 2018 Mar;11(3):209-217
pubmed: 29338466
Clin Schizophr Relat Psychoses. 2018 Jan;11(4):214-220
pubmed: 29341821
Drug Des Devel Ther. 2018 Feb 15;12:313-319
pubmed: 29497277

Auteurs

Laurent Ettouati (L)

EA 4446 Bioactive Molecules and Medicinal Chemistry, SFR Santé Lyon-Est CNRS UMS3453-INSERM US7, Faculté de Pharmacie⁻ISPB, Université Claude Bernard Lyon, Université de Lyon, 18 avenue Rockefeller, F-69373, Lyon Cedex 8, France. laurent.ettouati@univ-lyon1.fr.

Zoé Senta-Loys (Z)

LAGEP UMR 5007, CNRS, Université Claude Bernard Lyon 1, Université de Lyon, 43 bd du 11 novembre, F-69622 Villeurbanne, France. zoe.senta@gmail.com.

Sandrine Bourgeois (S)

LAGEP UMR 5007, CNRS, Université Claude Bernard Lyon 1, Université de Lyon, 43 bd du 11 novembre, F-69622 Villeurbanne, France. sandrine.bourgeois@univ-lyon1.fr.
ISPB-Faculté de Pharmacie, Université Claude Bernard-Lyon 1, Université de Lyon, 8 avenue Rockefeller, F-69373, Lyon Cedex 8, France. sandrine.bourgeois@univ-lyon1.fr.

Bernard Fenet (B)

Centre Commun de RMN, Université Lyon 1, Université de Lyon, 43 boulevard du 11 Novembre, F-69622 Villeurbanne Cedex, France. bernard.fenet@gmail.com.

Marc Le Borgne (ML)

EA 4446 Bioactive Molecules and Medicinal Chemistry, SFR Santé Lyon-Est CNRS UMS3453-INSERM US7, Faculté de Pharmacie⁻ISPB, Université Claude Bernard Lyon, Université de Lyon, 18 avenue Rockefeller, F-69373, Lyon Cedex 8, France. marc.le-borgne@univ-lyon1.fr.

Hatem Fessi (H)

LAGEP UMR 5007, CNRS, Université Claude Bernard Lyon 1, Université de Lyon, 43 bd du 11 novembre, F-69622 Villeurbanne, France. hatem.fessi@univ-lyon1.fr.

Classifications MeSH