WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 318867
CAS#: 145821-59-6 (HCl)
Description: Tiagabine is an anti-convulsive medication. The medication is also utilized in the treatment of panic disorder, as are a few other anticonvulsants. Tiagabine increases the level of gamma aminobutyric acid (GABA), the major inhibitory neurotransmitter in the central nervous system by blocking the GABA transporter and hence is classified as a GABA reuptake inhibitor.
MedKoo Cat#: 318867
Name: Tiagabine hydrochloride
CAS#: 145821-59-6 (HCl)
Chemical Formula: C20H26ClNO2S2
Exact Mass:
Molecular Weight: 412.003
Elemental Analysis: C, 58.31; H, 6.36; Cl, 8.60; N, 3.40; O, 7.77; S, 15.56
Related CAS #: 115103-54-3 (free base) 145821-59-6 (HCl)
Synonym: NO-329; NO329; NO 329; NNC-05-0328; NO-05-0328; Tiagabine hydrochloride; brand name Gabitril
IUPAC/Chemical Name: (R)-1-(4,4-bis(3-methylthiophen-2-yl)but-3-en-1-yl)piperidine-3-carboxylic acid hydrochloride
InChi Key: YUKARLAABCGMCN-PKLMIRHRSA-N
InChi Code: InChI=1S/C20H25NO2S2.ClH/c1-14-7-11-24-18(14)17(19-15(2)8-12-25-19)6-4-10-21-9-3-5-16(13-21)20(22)23;/h6-8,11-12,16H,3-5,9-10,13H2,1-2H3,(H,22,23);1H/t16-;/m1./s1
SMILES Code: CC1=C(SC=C1)C(=CCCN2CCC[C@H](C2)C(=O)O)C3=C(C=CS3)C.Cl
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
The following data is based on the product molecular weight 412.003 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 |
1: Pulman J, Hutton JL, Marson AG. Tiagabine add-on for drug-resistant partial epilepsy. Cochrane Database Syst Rev. 2014 Feb 5;2:CD001908. doi: 10.1002/14651858.CD001908.pub3. Review. PubMed PMID: 24500879.
2: Błaszczyk B. [Tiagabine--own experience in the refractory epilepsy treatment]. Wiad Lek. 2013;66(2 Pt 2):175-9. Review. Polish. PubMed PMID: 25775813.
3: Vasudev A, Macritchie K, Rao SK, Geddes J, Young AH. Tiagabine for acute affective episodes in bipolar disorder. Cochrane Database Syst Rev. 2012 Dec 12;12:CD004694. doi: 10.1002/14651858.CD004694.pub3. Review. PubMed PMID: 23235614.
4: Pulman J, Marson AG, Hutton JL. Tiagabine add-on for drug-resistant partial epilepsy. Cochrane Database Syst Rev. 2012 May 16;5:CD001908. doi: 10.1002/14651858.CD001908.pub2. Review. Update in: Cochrane Database Syst Rev. 2014;2:CD001908. PubMed PMID: 22592677; PubMed Central PMCID: PMC4058679.
5: Vasudev A, Macritchie K, Rao SN, Geddes J, Young AH. Tiagabine in the maintenance treatment of bipolar disorder. Cochrane Database Syst Rev. 2011 Dec 7;(12):CD005173. doi: 10.1002/14651858.CD005173.pub3. Review. PubMed PMID: 22161389.
6: Bentué-Ferrer D, Tribut O, Verdier MC; le groupe Suivi Thérapeutique Pharmacologique de la Société Française de Pharmacologie et de Thérapeutique. [Therapeutic drug monitoring of tiagabine]. Therapie. 2010 Jan-Feb;65(1):51-5. doi: 10.2515/therapie/2009065. Epub 2010 Mar 8. Review. French. PubMed PMID: 20205996.
7: Schwartz TL, Nihalani N. Tiagabine in anxiety disorders. Expert Opin Pharmacother. 2006 Oct;7(14):1977-87. Review. PubMed PMID: 17020423.
8: Young AH, Geddes JR, Macritchie K, Rao SN, Vasudev A. Tiagabine in the maintenance treatment of bipolar disorders. Cochrane Database Syst Rev. 2006 Jul 19;(3):CD005173. Review. Update in: Cochrane Database Syst Rev. 2011;(12):CD005173. PubMed PMID: 16856081.
9: Young AH, Geddes JR, Macritchie K, Rao SN, Watson S, Vasudev A. Tiagabine in the treatment of acute affective episodes in bipolar disorder: efficacy and acceptability. Cochrane Database Syst Rev. 2006 Jul 19;(3):CD004694. Review. Update in: Cochrane Database Syst Rev. 2012;12:CD004694. PubMed PMID: 16856056.
10: Spiller HA, Winter ML, Ryan M, Krenzelok EP, Anderson DL, Thompson M, Kumar S. Retrospective evaluation of tiagabine overdose. Clin Toxicol (Phila). 2005;43(7):855-9. Review. PubMed PMID: 16440513.
11: Stahl SM. Anticonvulsants as anxiolytics, part 1: tiagabine and other anticonvulsants with actions on GABA. J Clin Psychiatry. 2004 Mar;65(3):291-2. Review. PubMed PMID: 15096065.
12: de Borchgrave V, Lienard F, Willemart T, van Rijckevorsel K. Clinical and EEG findings in six patients with altered mental status receiving tiagabine therapy. Epilepsy Behav. 2003 Jun;4(3):326-37. Review. PubMed PMID: 12791336.
13: Sills GJ. Pre-clinical studies with the GABAergic compounds vigabatrin and tiagabine. Epileptic Disord. 2003 Mar;5(1):51-6. Review. PubMed PMID: 12773297.
14: Angehagen M, Ben-Menachem E, Rönnbäck L, Hansson E. Novel mechanisms of action of three antiepileptic drugs, vigabatrin, tiagabine, and topiramate. Neurochem Res. 2003 Feb;28(2):333-40. Review. PubMed PMID: 12608706.
15: Casas-Fernández C, Domingo-Jiménez R. [Characteristics and indications of tiagabine]. Rev Neurol. 2002 Sep;35 Suppl 1:S96-S100. Review. Spanish. PubMed PMID: 12373661.
16: Pereira J, Marson AG, Hutton JL. Tiagabine add-on for drug-resistant partial epilepsy. Cochrane Database Syst Rev. 2002;(3):CD001908. Review. Update in: Cochrane Database Syst Rev. 2012;5:CD001908. PubMed PMID: 12137637.
17: Kellinghaus C, Dziewas R, Lüdemann P. Tiagabine-related non-convulsive status epilepticus in partial epilepsy: three case reports and a review of the literature. Seizure. 2002 Jun;11(4):243-9. Review. PubMed PMID: 12027571.
18: Carta MG, Hardoy MC, Grunze H, Carpiniello B. The use of tiagabine in affective disorders. Pharmacopsychiatry. 2002 Jan;35(1):33-4. Review. PubMed PMID: 11819159.
19: Genton P, Guerrini R, Perucca E. Tiagabine in clinical practice. Epilepsia. 2001;42 Suppl 3:42-5. Review. PubMed PMID: 11520322.
20: Schachter SC. Pharmacology and clinical experience with tiagabine. Expert Opin Pharmacother. 2001 Jan;2(1):179-87. Review. PubMed PMID: 11336578.
Related CAS#
CAS#145821-59-6 ( Tiagabine HCl salt).
CAS#115103-54-3 ( Tiagabine free base).
