Explore a selection of our essential drug information below, or:
Identification
- Generic Name
- Guvacine
- DrugBank Accession Number
- DB08848
- Background
Guvacine is a pyridine alkaloid found in the Areca nut (also known as the Betel nut). It is an experimental drug with no approved indication. Experimental studies are still being investigated to determine all of the physiological effects and mechanisms of action of guvacine. Currently it has been determined that guvacine is a specific GABA reuptake inhibitor with no significant affinity at GABA receptors.
- Type
- Small Molecule
- Groups
- Experimental
- Structure
Structure for Guvacine (DB08848)
- Weight
- Average: 127.1412
Monoisotopic: 127.063328537 - Chemical Formula
- C6H9NO2
- Synonyms
- Not Available
Pharmacology
- Indication
There is no approved indication for guvacine.
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Experimental studies are still being investigated to determine all of the physiological effects of guvacine.
- Mechanism of action
Experimental studies are still being investigated to determine the exact mechanisms of action of guvacine. What is known is that guvacine binds selectively to presynaptic GABA reuptake transporters and prevents the reuptake of GABA, but has no affinity for GABA postsynaptic receptors.
Target Actions Organism USodium- and chloride-dependent GABA transporter 2 inhibitorHumans USodium- and chloride-dependent GABA transporter 1 inhibitorHumans USodium- and chloride-dependent GABA transporter 3 inhibitorHumans USodium- and chloride-dependent betaine transporter inhibitorHumans - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
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Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.Not Available
- Food Interactions
- Not Available
Products
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Ingredient UNII CAS InChI Key Guvacine hydrochloride Not Available Not Available FGNUNVVTHHKDAM-UHFFFAOYSA-N
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as alkaloids and derivatives. These are naturally occurring chemical compounds that contain mostly basic nitrogen atoms. This group also includes some related compounds with neutral and even weakly acidic properties. Also some synthetic compounds of similar structure are attributed to alkaloids. In addition to carbon, hydrogen and nitrogen, alkaloids may also contain oxygen, sulfur and more rarely other elements such as chlorine, bromine, and phosphorus.
- Kingdom
- Organic compounds
- Super Class
- Alkaloids and derivatives
- Class
- Not Available
- Sub Class
- Not Available
- Direct Parent
- Alkaloids and derivatives
- Alternative Parents
- Hydropyridines / Amino acids / Monocarboxylic acids and derivatives / Dialkylamines / Carboxylic acids / Azacyclic compounds / Organopnictogen compounds / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
- Substituents
- Aliphatic heteromonocyclic compound / Alkaloid or derivatives / Amine / Amino acid / Amino acid or derivatives / Azacycle / Carbonyl group / Carboxylic acid / Carboxylic acid derivative / Hydrocarbon derivative
- Molecular Framework
- Aliphatic heteromonocyclic compounds
- External Descriptors
- secondary amino compound, alpha,beta-unsaturated monocarboxylic acid, beta-amino acid, tetrahydropyridine, pyridine alkaloid (CHEBI:5576) / Pyridine alkaloids (C10149)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- 41538P325K
- CAS number
- 498-96-4
- InChI Key
- QTDZOWFRBNTPQR-UHFFFAOYSA-N
- InChI
- InChI=1S/C6H9NO2/c8-6(9)5-2-1-3-7-4-5/h2,7H,1,3-4H2,(H,8,9)
- IUPAC Name
- 1,2,5,6-tetrahydropyridine-3-carboxylic acid
- SMILES
- OC(=O)C1=CCCNC1
References
- Synthesis Reference
McELVAIN SM, STORK G: Piperidine derivatives; the preparation of l-benzoyl-3-carbethoxy-4-piperidone; a synthesis of guvacine. J Am Chem Soc. 1946 Jun;68:1049-53.
- General References
- Krogsgaard-Larsen P, Frolund B, Frydenvang K: GABA uptake inhibitors. Design, molecular pharmacology and therapeutic aspects. Curr Pharm Des. 2000 Aug;6(12):1193-209. [Article]
- O'Neil, Maryadele J. (2013). The Merck Index : An Encyclopedia of Chemicals, Drugs, and Biologicals (15th ed.). Royal Society of Chemistry, The. [ISBN:978-1849736701]
- External Links
- KEGG Compound
- C10149
- PubChem Compound
- 3532
- PubChem Substance
- 175427121
- ChemSpider
- 3412
- BindingDB
- 90787
- ChEBI
- 5576
- ChEMBL
- CHEMBL76768
- ZINC
- ZINC000003872753
- Wikipedia
- Guvacine
- MSDS
- Download (39.8 KB)
Clinical Trials
- Clinical Trials
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Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 306 - 309 °C From MSDS. water solubility Soluble in water, and almost insoluble in 100% alcohol, ether, chloroform, and benzene. From The Merck Index monographs. - Predicted Properties
Property Value Source Water Solubility 30.8 mg/mL ALOGPS logP -2.2 ALOGPS logP -2.6 Chemaxon logS -0.62 ALOGPS pKa (Strongest Acidic) 3.57 Chemaxon pKa (Strongest Basic) 9.77 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 3 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 49.33 Å2 Chemaxon Rotatable Bond Count 1 Chemaxon Refractivity 33.8 m3·mol-1 Chemaxon Polarizability 12.85 Å3 Chemaxon Number of Rings 1 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9325 Blood Brain Barrier + 0.5447 Caco-2 permeable - 0.5696 P-glycoprotein substrate Substrate 0.6572 P-glycoprotein inhibitor I Non-inhibitor 0.9704 P-glycoprotein inhibitor II Non-inhibitor 0.9782 Renal organic cation transporter Non-inhibitor 0.6481 CYP450 2C9 substrate Non-substrate 0.8893 CYP450 2D6 substrate Non-substrate 0.8182 CYP450 3A4 substrate Non-substrate 0.7338 CYP450 1A2 substrate Non-inhibitor 0.9045 CYP450 2C9 inhibitor Non-inhibitor 0.9071 CYP450 2D6 inhibitor Non-inhibitor 0.958 CYP450 2C19 inhibitor Non-inhibitor 0.9114 CYP450 3A4 inhibitor Non-inhibitor 0.9888 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9907 Ames test Non AMES toxic 0.8368 Carcinogenicity Non-carcinogens 0.9492 Biodegradation Ready biodegradable 0.9306 Rat acute toxicity 1.9903 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.5 hERG inhibition (predictor II) Non-inhibitor 0.9056
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-0560-9200000000-d8c5ef9e7cf51eb4bd41 Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-01t9-0900000000-fec9fb797ff02855ad37 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-004i-2900000000-ff9f318ae43e5692ff86 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-0fsi-9200000000-4574d78feb81075666ee Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-001i-9000000000-576721b99bea03f3a59c Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0uyi-9000000000-20dcc5ec330432512744 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-001i-9000000000-84c3b604d7146ae71be7 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 123.5721275 predictedDarkChem Lite v0.1.0 [M-H]- 123.645905 predictedDeepCCS 1.0 (2019) [M+H]+ 124.2751275 predictedDarkChem Lite v0.1.0 [M+H]+ 126.383514 predictedDeepCCS 1.0 (2019) [M+Na]+ 123.9271275 predictedDarkChem Lite v0.1.0 [M+Na]+ 135.15416 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Mediates sodium- and chloride-dependent transport of gamma-aminobutyric acid (GABA) (PubMed:17502375, PubMed:22932902). Mediates transport of beta-alanine (PubMed:17502375). Can also mediate transport of taurine and hypotaurine (By similarity)
- Specific Function
- amino acid transmembrane transporter activity
- Gene Name
- SLC6A13
- Uniprot ID
- Q9NSD5
- Uniprot Name
- Sodium- and chloride-dependent GABA transporter 2
- Molecular Weight
- 68008.205 Da
References
- Schousboe A, Thorbek P, Hertz L, Krogsgaard-Larsen P: Effects of GABA analogues of restricted conformation on GABA transport in astrocytes and brain cortex slices and on GABA receptor binding. J Neurochem. 1979 Jul;33(1):181-9. [Article]
- Krogsgaard-Larsen P, Frolund B, Frydenvang K: GABA uptake inhibitors. Design, molecular pharmacology and therapeutic aspects. Curr Pharm Des. 2000 Aug;6(12):1193-209. [Article]
- Sunol C, Babot Z, Cristofol R, Sonnewald U, Waagepetersen HS, Schousboe A: A possible role of the non-GAT1 GABA transporters in transfer of GABA from GABAergic to glutamatergic neurons in mouse cerebellar neuronal cultures. Neurochem Res. 2010 Sep;35(9):1384-90. doi: 10.1007/s11064-010-0196-1. Epub 2010 May 30. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Mediates transport of gamma-aminobutyric acid (GABA) together with sodium and chloride and is responsible for the reuptake of GABA from the synapse (PubMed:30132828). The translocation of GABA, however, may also occur in the reverse direction leading to the release of GABA (By similarity). The direction and magnitude of GABA transport is a consequence of the prevailing thermodynamic conditions, determined by membrane potential and the intracellular and extracellular concentrations of Na(+), Cl(-) and GABA (By similarity). Can also mediate sodium- and chloride-dependent transport of hypotaurine but to a much lower extent as compared to GABA (By similarity)
- Specific Function
- gamma-aminobutyric acid transmembrane transporter activity
- Gene Name
- SLC6A1
- Uniprot ID
- P30531
- Uniprot Name
- Sodium- and chloride-dependent GABA transporter 1
- Molecular Weight
- 67073.0 Da
References
- Sunol C, Babot Z, Cristofol R, Sonnewald U, Waagepetersen HS, Schousboe A: A possible role of the non-GAT1 GABA transporters in transfer of GABA from GABAergic to glutamatergic neurons in mouse cerebellar neuronal cultures. Neurochem Res. 2010 Sep;35(9):1384-90. doi: 10.1007/s11064-010-0196-1. Epub 2010 May 30. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Mediates sodium- and chloride-dependent transport of gamma-aminobutyric acid (GABA) (PubMed:7874447). Can also mediate transport of beta-alanine and to a lower extent that of taurine and hypotaurine (By similarity)
- Specific Function
- amino acid binding
- Gene Name
- SLC6A11
- Uniprot ID
- P48066
- Uniprot Name
- Sodium- and chloride-dependent GABA transporter 3
- Molecular Weight
- 70605.145 Da
References
- Sunol C, Babot Z, Cristofol R, Sonnewald U, Waagepetersen HS, Schousboe A: A possible role of the non-GAT1 GABA transporters in transfer of GABA from GABAergic to glutamatergic neurons in mouse cerebellar neuronal cultures. Neurochem Res. 2010 Sep;35(9):1384-90. doi: 10.1007/s11064-010-0196-1. Epub 2010 May 30. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Transporter that mediates cellular uptake of betaine and GABA in a sodium- and chloride-dependent process (PubMed:7589472). May have a role in regulation of GABAergic transmission in the brain through the reuptake of GABA into presynaptic terminals, as well as in osmotic regulation. Probably also involved in renal and hepatic osmotic regulation (By similarity)
- Specific Function
- amino acid transmembrane transporter activity
- Gene Name
- SLC6A12
- Uniprot ID
- P48065
- Uniprot Name
- Sodium- and chloride-dependent betaine transporter
- Molecular Weight
- 69367.655 Da
References
- Ruiz-Tachiquin ME, Sanchez-Lemus E, Soria-Jasso LE, Arias-Montano JA, Ortega A: Gamma-aminobutyric acid transporter (BGT-1) expressed in human astrocytoma U373 MG cells: pharmacological and molecular characterization and phorbol ester-induced inhibition. J Neurosci Res. 2002 Jul 1;69(1):125-32. [Article]
Drug created at March 02, 2013 01:48 / Updated at August 02, 2024 07:32