Tiagabine hydrochloride - ≥98%(HPLC) , GABA transporter 1 inhibitor, CAS No.145821-59-6, GABA transporter 1 inhibitor

CAS: 145821-59-6 Cat. No.: T134804 Molecular Weight: 412 EC Number: 127-535-3 PubChem CID: 91274

GRADE & PURITY ≥98%(HPLC)

Synonyms

Gabitril | KS-1217 | Tiagabine hydrochloride (USAN:USP) | UNII-DQH6T6D8OY | Tiagabine (hydrochloride) | Abbott 70569.HCl | CEP-6671 | Ethanone, 1-imidazo[1,2-b]pyridazin-3-yl- | s4661 | TIAGABINE HCl | Tox21_112245_1 | (3R)-1-[4,4-bis(3-methylthiophen-2-y

Storage

Store at 2-8°C

Shipped In

Wet ice

Overview

Tiagabine hydrochloride(NO328 hydrochloride) is a selective gamma-aminobutyric acid (GABA) reuptake inhibitor.
Tiagabine hydrochloride was used to study serotoninergic transmission in G1 cells.

Specifications

Synonyms

Gabitril | KS-1217 | Tiagabine hydrochloride (USAN:USP) | UNII-DQH6T6D8OY | Tiagabine (hydrochloride) | Abbott 70569.HCl | CEP-6671 | Ethanone, 1-imidazo[1, 2-b]pyridazin-3-yl- | s4661 | TIAGABINE HCl | Tox21_112245_1 | (3R)-1-[4, 4-bis(3-methylthiophen-2-y

Specifications & Purity

≥98%(HPLC)

Biochemical and Physiological Mechanisms

GABA uptake inhibitor (IC50= 67 nMin vivo). Exhibits high affinity and selectivity for the GAT-1 GABA transporter. Anticonvulsant; also attenuates established dynorphin-induced allodynia in a mouse model after systemic administration.

Storage

Store at 2-8°C

Shipped In

Wet ice

This product requires cold chain shipping. Ground and other economy services are not available.

Action Type

INHIBITOR

Mechanism of action

GABA transporter 1 inhibitor

Purity

≥98%(HPLC)

Names and Identifiers

• Pubchem Sid: 504756054
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504756054
• Canonical Smiles: CC1=C(SC=C1)C(=CCCN2CCCC(C2)C(=O)O)C3=C(C=CS3)C.Cl
• IUPAC Name: (3R)-1-[4,4-bis(3-methylthiophen-2-yl)but-3-enyl]piperidine-3-carboxylic acid;hydrochloride
• InChIKey: YUKARLAABCGMCN-PKLMIRHRSA-N
• 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
• Isomeric SMILES: CC1=C(SC=C1)C(=CCCN2CCC[C@H](C2)C(=O)O)C3=C(C=CS3)C.Cl
• WGK Germany: 3
• PubChem CID: 91274
• Molecular Weight: 412

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Class Piperidines
      • Subclass Piperidinecarboxylic acids and derivatives

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Class: Piperidines
• Subclass: Piperidinecarboxylic acids and derivatives
• Intermediate Tree Nodes: Not available
• Direct Parent: Piperidinecarboxylic acids
• Alternative Parents: Thiophenes Heteroaromatic compounds Trialkylamines Amino acids Monocarboxylic acids and derivatives Carboxylic acids Azacyclic compounds Organopnictogen compounds Organic oxides Hydrochlorides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aromatic heteromonocyclic compounds
• Substituents: Piperidinecarboxylic acid - Thiophene - Heteroaromatic compound - Amino acid or derivatives - Tertiary amine - Amino acid - Tertiary aliphatic amine - Carboxylic acid derivative - Carboxylic acid - Monocarboxylic acid or derivatives - Azacycle - Organopnictogen compound - Organic oxygen compound - Organooxygen compound - Organonitrogen compound - Organic nitrogen compound - Amine - Organic oxide - Hydrocarbon derivative - Hydrochloride - Carbonyl group - Aromatic heteromonocyclic compound
• Description: This compound belongs to the class of organic compounds known as piperidinecarboxylic acids. These are compounds containing a piperidine ring which bears a carboxylic acid group.
• External Descriptors: hydrochloride

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

SLC6A1 Tclin Sodium- and chloride-dependent GABA transporter 1 (1 Activities)

Discover Target: SLC6A1

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

SLC6A1 Tclin GABA transporter 1 (308 Activities)

Discover Target: SLC6A1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

TDP1 Tchem Tyrosyl-DNA phosphodiesterase 1 (345557 Activities)

Discover Target: TDP1

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GMNN Tbio Geminin (128009 Activities)

Discover Target: GMNN

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Associated Targets(non-human)

Pseudomonas aeruginosa (123386 Activities)

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Klebsiella pneumoniae (43867 Activities)

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Staphylococcus aureus (210822 Activities)

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Acinetobacter baumannii (41033 Activities)

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Escherichia coli (133304 Activities)

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Cryptococcus neoformans (21258 Activities)

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Candida albicans (78123 Activities)

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Mus musculus (284745 Activities)

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rep Replicase polyprotein 1ab (378 Activities)

Discover Target: rep

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Slc6a11 GABA transporter (190 Activities)

Discover Target: Slc6a11

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Mechanisms of Action

Chemical and Physical Properties

• Solubility: Solvent:water, Max Conc. mg/mL: 20.6, Max Conc. mM: 50; Solvent:DMSO, Max Conc. mg/mL: 41.2, Max Conc. mM: 100
• Sensitivity: Hygroscopic,Heat Sensitive
• Specific Rotation[α]: -11° (C=1.0,H2O)
• Melt Point(°C): 193 °C
• Molecular Weight: 412.000 g/mol
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 411.109 Da
• Monoisotopic Mass: 411.109 Da
• Topological Polar Surface Area: 97.000 Ų
• Heavy Atom Count: 26
• Formal Charge: 0
• Complexity: 474.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 1
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 2

XLogP3

References

1. Zhen Zou, Xiaodou Liao, Le Yang, Ziyun Huang, Hua Yang, Qi Yan, Yufei Zhang, Zhihe Qing, Lihua Zhang, Feng Feng, Ronghua Yang.  (2020)  Human Serum Albumin-Occupying-Based Fluorescence Turn-On Analysis of Antiepileptic Drug Tiagabine Hydrochloride.  ANALYTICAL CHEMISTRY,      [PMID:32008316] [10.1021/acs.analchem.9b03507]