Identification
- Generic Name
- gamma-Aminobutyric acid
- DrugBank Accession Number
- DB02530
- Background
The most common inhibitory neurotransmitter in the central nervous system.
- Type
- Small Molecule
- Groups
- Approved, Investigational
- Structure
Structure for gamma-Aminobutyric acid (DB02530)
- Weight
- Average: 103.1198
Monoisotopic: 103.063328537 - Chemical Formula
- C4H9NO2
- Synonyms
- 4-aminobutanoic acid
- 4-aminobutyric acid
- 4Abu
- GABA
- gamma-Aminobutyric acid
- piperidic acid
- piperidinic acid
- γ-amino-n-butyric acid
- γ-aminobutanoic acid
- γ-Aminobuttersäure
- γ-aminobutyric acid
- ω-aminobutyric acid
Pharmacology
- Indication
Not Available
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Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Maintenance of Brain health •••••••••••• ••••••• •••••• - Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism UGamma-aminobutyric acid type B receptor subunit 1 Not Available Humans UGamma-aminobutyric acid type B receptor subunit 2 Not Available Humans UGlycine amidinotransferase, mitochondrial Not Available Humans - 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
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- Pathways
Pathway Category Homocarnosinosis Disease Glutamate Metabolism Metabolic Hyperinsulinism-Hyperammonemia Syndrome Disease 2-Hydroxyglutric Aciduria (D and L Form) Disease 4-Hydroxybutyric Aciduria/Succinic Semialdehyde Dehydrogenase Deficiency Disease Succinic Semialdehyde Dehydrogenase Deficiency Disease - 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
- No interactions found.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Gamma-Aminobutyric Acid Hydrochloride 0S3LEB8Q58 5959-35-3 QPGLUEKHBNOAHG-UHFFFAOYSA-N - Over the Counter Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Gongjinhyang Qi and Jin Eye Cream 0.022 mL/100mL Topical Lg Household & Health Care Ltd. 2010-05-24 Not applicable US 
เบนโต Tablet, coated 250 mg Oral บริษัท ที.พี.ดรัก แลบบอราทอรี่ส์ (1969) จำกัด 2013-11-14 Not applicable Thailand 
- Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Gongjinhyang Qi and Jin Eye gamma-Aminobutyric acid (0.022 mL/100mL) Cream Topical Lg Household & Health Care Ltd. 2010-05-24 Not applicable US Medi-doze Rx Sleep Aid gamma-Aminobutyric acid (30 mg/1) + Melatonin (6 mg/1) + Valerian (50 mg/1) Tablet Oral Two Hip Consulting, Llc 2013-02-20 2016-04-11 US Prazolamine gamma-Aminobutyric acid (100 mg/1) + Carisoprodol (350 mg/1) Kit Oral Physician Therapeutics Llc 2011-07-07 Not applicable US Therabenzaprine-60 gamma-Aminobutyric acid (100 mg/1) + Cyclobenzaprine hydrochloride (10 mg/1) Kit Oral Physician Therapeutics Llc 2011-05-15 Not applicable US Therabenzaprine-90 gamma-Aminobutyric acid (100 mg/1) + Cyclobenzaprine hydrochloride (10 mg/1) Kit Oral Physician Therapeutics Llc 2011-02-16 Not applicable US
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as gamma amino acids and derivatives. These are amino acids having a (-NH2) group attached to the gamma carbon atom.
- Kingdom
- Organic compounds
- Super Class
- Organic acids and derivatives
- Class
- Carboxylic acids and derivatives
- Sub Class
- Amino acids, peptides, and analogues
- Direct Parent
- Gamma amino acids and derivatives
- Alternative Parents
- Amino fatty acids / Straight chain fatty acids / Amino acids / Monocarboxylic acids and derivatives / Carboxylic acids / Organopnictogen compounds / Organic oxides / Monoalkylamines / Hydrocarbon derivatives / Carbonyl compounds
- Substituents
- Aliphatic acyclic compound / Amine / Amino acid / Amino fatty acid / Carbonyl group / Carboxylic acid / Fatty acid / Fatty acyl / Gamma amino acid or derivatives / Hydrocarbon derivative
- Molecular Framework
- Aliphatic acyclic compounds
- External Descriptors
- monocarboxylic acid, gamma-amino acid (CHEBI:16865) / Amino fatty acids, Other amino acids, Biogenic amines (C00334) / Amino fatty acids (LMFA01100039)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- 2ACZ6IPC6I
- CAS number
- 56-12-2
- InChI Key
- BTCSSZJGUNDROE-UHFFFAOYSA-N
- InChI
- InChI=1S/C4H9NO2/c5-3-1-2-4(6)7/h1-3,5H2,(H,6,7)
- IUPAC Name
- 4-aminobutanoic acid
- SMILES
- NCCCC(O)=O
References
- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0000112
- KEGG Drug
- D00058
- KEGG Compound
- C00334
- PubChem Compound
- 119
- PubChem Substance
- 46507841
- ChemSpider
- 116
- BindingDB
- 24183
- 4617
- ChEBI
- 59888
- ChEMBL
- CHEMBL96
- ZINC
- ZINC000001532620
- Guide to Pharmacology
- GtP Drug Page
- PDBe Ligand
- ABU
- Wikipedia
- Gamma-Aminobutyric_acid
- PDB Entries
- 1m19 / 1m1a / 1qur / 1s32 / 2jt9 / 2okj / 2okk / 2yoe / 3usu / 3v5a … show 69 more
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 4 Completed Treatment Pain 1 4 Completed Treatment Vertigo 1 1, 2 Completed Treatment Type 1 Diabetes Mellitus 1 Not Available Completed Not Available Type 1 Diabetes Mellitus 1 Not Available Completed Other Sleep disorders and disturbances 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Cream Topical 0.022 mL/100mL Tablet Oral Kit Oral Tablet, coated Oral 250 mg - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 365.0 mg/mL ALOGPS logP -3 ALOGPS logP -2.9 Chemaxon logS 0.55 ALOGPS pKa (Strongest Acidic) 4.53 Chemaxon pKa (Strongest Basic) 10.22 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 3 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 63.32 Å2 Chemaxon Rotatable Bond Count 3 Chemaxon Refractivity 25.46 m3·mol-1 Chemaxon Polarizability 10.62 Å3 Chemaxon Number of Rings 0 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 + 0.9258 Blood Brain Barrier + 0.9117 Caco-2 permeable - 0.6516 P-glycoprotein substrate Non-substrate 0.7407 P-glycoprotein inhibitor I Non-inhibitor 0.9819 P-glycoprotein inhibitor II Non-inhibitor 0.9677 Renal organic cation transporter Non-inhibitor 0.8182 CYP450 2C9 substrate Non-substrate 0.8751 CYP450 2D6 substrate Non-substrate 0.7724 CYP450 3A4 substrate Non-substrate 0.7728 CYP450 1A2 substrate Non-inhibitor 0.9495 CYP450 2C9 inhibitor Non-inhibitor 0.9641 CYP450 2D6 inhibitor Non-inhibitor 0.9786 CYP450 2C19 inhibitor Non-inhibitor 0.9777 CYP450 3A4 inhibitor Non-inhibitor 0.942 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9821 Ames test Non AMES toxic 0.8858 Carcinogenicity Non-carcinogens 0.7416 Biodegradation Ready biodegradable 0.9414 Rat acute toxicity 1.1546 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9362 hERG inhibition (predictor II) Non-inhibitor 0.9322
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 117.1838019 predictedDarkChem Lite v0.1.0 [M-H]- 117.2559019 predictedDarkChem Lite v0.1.0 [M-H]- 117.1606019 predictedDarkChem Lite v0.1.0 [M-H]- 130.9198 predictedDeepCCS 1.0 (2019) [M+H]+ 118.1164019 predictedDarkChem Lite v0.1.0 [M+H]+ 117.9935019 predictedDarkChem Lite v0.1.0 [M+H]+ 118.2127019 predictedDarkChem Lite v0.1.0 [M+H]+ 133.68158 predictedDeepCCS 1.0 (2019) [M+Na]+ 117.6179019 predictedDarkChem Lite v0.1.0 [M+Na]+ 117.6420019 predictedDarkChem Lite v0.1.0 [M+Na]+ 117.6317019 predictedDarkChem Lite v0.1.0 [M+Na]+ 141.82634 predictedDeepCCS 1.0 (2019)
Targets
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Use our structured and evidence-based datasets to unlock newinsights and accelerate drug research.
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- G-protein coupled gaba receptor activity
- Specific Function
- Component of a heterodimeric G-protein coupled receptor for GABA, formed by GABBR1 and GABBR2. Within the heterodimeric GABA receptor, only GABBR1 seems to bind agonists, while GABBR2 mediates coup...
- Gene Name
- GABBR1
- Uniprot ID
- Q9UBS5
- Uniprot Name
- Gamma-aminobutyric acid type B receptor subunit 1
- Molecular Weight
- 108319.4 Da
References
- Olianas MC, Ambu R, Garau L, Onali P: Allosteric modulation of GABA(B) receptor function in human frontal cortex. Neurochem Int. 2005 Jan;46(2):149-58. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- G-protein coupled gaba receptor activity
- Specific Function
- Component of a heterodimeric G-protein coupled receptor for GABA, formed by GABBR1 and GABBR2. Within the heterodimeric GABA receptor, only GABBR1 seems to bind agonists, while GABBR2 mediates coup...
- Gene Name
- GABBR2
- Uniprot ID
- O75899
- Uniprot Name
- Gamma-aminobutyric acid type B receptor subunit 2
- Molecular Weight
- 105820.52 Da
References
- Olianas MC, Ambu R, Garau L, Onali P: Allosteric modulation of GABA(B) receptor function in human frontal cortex. Neurochem Int. 2005 Jan;46(2):149-58. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Glycine amidinotransferase activity
- Specific Function
- Catalyzes the biosynthesis of guanidinoacetate, the immediate precursor of creatine. Creatine plays a vital role in energy metabolism in muscle tissues. May play a role in embryonic and central ner...
- Gene Name
- GATM
- Uniprot ID
- P50440
- Uniprot Name
- Glycine amidinotransferase, mitochondrial
- Molecular Weight
- 48455.01 Da
References
- Fritsche E, Humm A, Huber R: The ligand-induced structural changes of human L-Arginine:Glycine amidinotransferase. A mutational and crystallographic study. J Biol Chem. 1999 Jan 29;274(5):3026-32. [Article]
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- L-proline transmembrane transporter activity
- Specific Function
- Neutral amino acid/proton symporter. Has a pH-dependent electrogenic transport activity for small amino acids such as glycine, alanine and proline. Besides small apolar L-amino acids, it also recog...
- Gene Name
- SLC36A1
- Uniprot ID
- Q7Z2H8
- Uniprot Name
- Proton-coupled amino acid transporter 1
- Molecular Weight
- 53075.045 Da
References
- Thwaites DT, Basterfield L, McCleave PM, Carter SM, Simmons NL: Gamma-Aminobutyric acid (GABA) transport across human intestinal epithelial (Caco-2) cell monolayers. Br J Pharmacol. 2000 Feb;129(3):457-64. [Article]
Drug created at June 13, 2005 13:24 / Updated at February 21, 2021 18:51