NAV

Guvacine

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
 3D
Similar Structures
Weight
Average: 127.1412
Monoisotopic: 127.063328537
Chemical Formula
C6H9NO2
Synonyms
没有t Available

Pharmacology

Indication

There is no approved indication for guvacine.

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Contraindications & Blackbox Warnings
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Pharmacodynamics

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
inhibitor
 Humans
USodium- and chloride-dependent GABA transporter 1
inhibitor
 Humans
USodium- and chloride-dependent GABA transporter 3
inhibitor
 Humans
USodium- and chloride-dependent betaine transporter
inhibitor
 Humans
Absorption

没有t Available

Volume of distribution

没有t Available

Protein binding

没有t Available

Metabolism
没有t Available
Route of elimination

没有t Available

Half-life

没有t Available

Clearance

没有t Available

Adverse Effects
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Toxicity

没有t Available

Pathways
没有t Available
Pharmacogenomic Effects/ADRsBrowse all" title="" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
没有t Available

Interactions

Drug InteractionsLearn More" title="" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
这些信息不应该被解释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.
没有t Available
Food Interactions
没有t Available

Products

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Product Ingredients
Ingredient UNII CAS InChI Key
Guvacine hydrochloride 没有t Available 没有t Available FGNUNVVTHHKDAM-UHFFFAOYSA-N

Categories

Drug Categories
Chemical TaxonomyProvided byClassyfire
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
没有t Available
子课
没有t 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.
一般引用
  1. 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]
  2. 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]
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 TrialsLearn More" title="" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count

Pharmacoeconomics

Manufacturers
没有t Available
Packagers
没有t Available
Dosage Forms
没有t Available
Prices
没有t Available
Patents
没有t 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 没有 Chemaxon
Veber's Rule 没有 Chemaxon
MDDR-like Rule 没有 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 没有n-inhibitor 0.9704
P-glycoprotein inhibitor II 没有n-inhibitor 0.9782
Renal organic cation transporter 没有n-inhibitor 0.6481
CYP450 2C9 substrate 没有n-substrate 0.8893
CYP450 2D6 substrate 没有n-substrate 0.8182
CYP450 3A4 substrate 没有n-substrate 0.7338
CYP450 1A2 substrate 没有n-inhibitor 0.9045
CYP450 2C9 inhibitor 没有n-inhibitor 0.9071
CYP450 2D6 inhibitor 没有n-inhibitor 0.958
CYP450 2C19 inhibitor 没有n-inhibitor 0.9114
CYP450 3A4 inhibitor 没有n-inhibitor 0.9888
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9907
Ames test 没有n AMES toxic 0.8368
Carcinogenicity 没有n-carcinogens 0.9492
Biodegradation Ready biodegradable 0.9306
Rat acute toxicity 1.9903 LD50, mol/kg 没有t applicable
hERG inhibition (predictor I) Weak inhibitor 0.5
hERG inhibition (predictor II) 没有n-inhibitor 0.9056
ADMET data is predicted usingadmetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
没有t Available
Spectra
Spectrum Spectrum Type Splash Key
Predicted GC-MS Spectrum - GC-MS Predicted GC-MS 没有t Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS 没有t Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS 没有t Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS 没有t Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS 没有t Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS 没有t Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS 没有t Available

Targets

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Details 1.Sodium- and chloride-dependent GABA transporter 2
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Neurotransmitter:sodium symporter activity
Specific Function
Sodium-dependent GABA and taurine transporter. In presynaptic terminals, regulates GABA signaling termination through GABA uptake. May also be involved in beta-alanine transport.
Gene Name
SLC6A13
Uniprot ID
Q9NSD5
Uniprot Name
Sodium- and chloride-dependent GABA transporter 2
分子量
68008.205 Da
References
  1. 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]
  2. 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]
  3. 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]
Details 2.Sodium- and chloride-dependent GABA transporter 1
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Neurotransmitter:sodium symporter activity
Specific Function
Terminates the action of GABA by its high affinity sodium-dependent reuptake into presynaptic terminals.
Gene Name
SLC6A1
Uniprot ID
P30531
Uniprot Name
Sodium- and chloride-dependent GABA transporter 1
分子量
67073.0 Da
References
  1. 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]
Details 3.Sodium- and chloride-dependent GABA transporter 3
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Neurotransmitter:sodium symporter activity
Specific Function
Terminates the action of GABA by its high affinity sodium-dependent reuptake into presynaptic terminals.
Gene Name
SLC6A11
Uniprot ID
P48066
Uniprot Name
Sodium- and chloride-dependent GABA transporter 3
分子量
70605.145 Da
References
  1. 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]
Details 4.Sodium- and chloride-dependent betaine transporter
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Neurotransmitter:sodium symporter activity
Specific Function
Transports betaine and GABA. 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.
Gene Name
SLC6A12
Uniprot ID
P48065
Uniprot Name
Sodium- and chloride-dependent betaine transporter
分子量
69367.655 Da
References
  1. 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 April 07, 2023 13:27