Gavestinel
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Identification
- Generic Name
- Gavestinel
- DrugBank Accession Number
- DB06741
- Background
Highly potent and selective non-competitive antagonist acting at the strychnine-insensitive glycine binding site of the NMDA receptor-channel complex (Kd = 0.8 nM). Gavestinel displays > 1000-fold selectivity over NMDA, AMPA and kainate binding sites and is orally bioavailable and active in vivo.
- Type
- Small Molecule
- Groups
- Investigational
- Structure
- Weight
- Average: 375.21
Monoisotopic: 374.0224977 - Chemical Formula
- C18H12Cl2N2O3
- Synonyms
- Gavestinel
- External IDs
- GV 150526X
- GV-150,526A
- GV-150526X
Pharmacology
- Indication
Not Available
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- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism UGlutamate (NMDA) receptor antagonistHumans - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
Hover over products below to view reaction partners
- 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
- 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.
Drug Interaction Integrate drug-drug
interactions in your softwareAdenine The metabolism of Gavestinel can be decreased when combined with Adenine. Amitriptyline The metabolism of Gavestinel can be decreased when combined with Amitriptyline. Asciminib The metabolism of Gavestinel can be decreased when combined with Asciminib. Atazanavir The metabolism of Gavestinel can be decreased when combined with Atazanavir. Cannabidiol The metabolism of Gavestinel can be decreased when combined with Cannabidiol. - Food Interactions
- Not Available
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 Gv 150526a 80W7787JVB 153436-38-5 GRSDSTMFQHAESM-UHDJGPCESA-M
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as indolecarboxylic acids and derivatives. These are compounds containing a carboxylic acid group (or a derivative thereof) linked to an indole.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Indoles and derivatives
- Sub Class
- Indolecarboxylic acids and derivatives
- Direct Parent
- Indolecarboxylic acids and derivatives
- Alternative Parents
- Indoles / Anilides / Pyrrole 2-carboxylic acids / N-arylamides / Substituted pyrroles / Aryl chlorides / Heteroaromatic compounds / Secondary carboxylic acid amides / Carboxylic acids / Azacyclic compounds show 4 more
- Substituents
- Anilide / Aromatic heteropolycyclic compound / Aryl chloride / Aryl halide / Azacycle / Benzenoid / Carbonyl group / Carboxamide group / Carboxylic acid / Carboxylic acid derivative show 18 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- 318X4QY113
- CAS number
- 153436-22-7
- InChI Key
- WZBNEZWCNKUOSM-VOTSOKGWSA-N
- InChI
- InChI=1S/C18H12Cl2N2O3/c19-10-8-13(20)16-12(17(18(24)25)22-14(16)9-10)6-7-15(23)21-11-4-2-1-3-5-11/h1-9,22H,(H,21,23)(H,24,25)/b7-6+
- IUPAC Name
- 4,6-dichloro-3-[(1E)-2-(phenylcarbamoyl)eth-1-en-1-yl]-1H-indole-2-carboxylic acid
- SMILES
- OC(=O)C1=C(\C=C\C(=O)NC2=CC=CC=C2)C2=C(Cl)C=C(Cl)C=C2N1
References
- General References
- Warach S, Kaufman D, Chiu D, Devlin T, Luby M, Rashid A, Clayton L, Kaste M, Lees KR, Sacco R, Fisher M: Effect of the Glycine Antagonist Gavestinel on cerebral infarcts in acute stroke patients, a randomized placebo-controlled trial: The GAIN MRI Substudy. Cerebrovasc Dis. 2006;21(1-2):106-11. Epub 2005 Dec 9. [Article]
- External Links
- PubChem Compound
- 6450546
- PubChem Substance
- 347827789
- ChemSpider
- 4953148
- BindingDB
- 50010475
- ChEMBL
- CHEMBL44793
- ZINC
- ZINC000003797383
- Wikipedia
- Gavestinel
- MSDS
- Download (608 KB)
Clinical Trials
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.0012 mg/mL ALOGPS logP 4.18 ALOGPS logP 4.45 Chemaxon logS -5.5 ALOGPS pKa (Strongest Acidic) 5.04 Chemaxon pKa (Strongest Basic) -2 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 3 Chemaxon Hydrogen Donor Count 3 Chemaxon Polar Surface Area 82.19 Å2 Chemaxon Rotatable Bond Count 4 Chemaxon Refractivity 99.17 m3·mol-1 Chemaxon Polarizability 36.97 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-06rl-2129000000-25acb70c567f43292ce3 Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-056r-0009000000-49f07545e774b130ac7e Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-0a4i-0092000000-be88ac3caf4518e30e21 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-0fb9-1029000000-9e255ff71748b2eab180 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-0a6r-0079000000-86c5752dd4d696cae115 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-0zfr-0079000000-b353b3271810bd5446f6 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-08mj-0096000000-a6878f8dfbd76474ede9 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]- 176.56148 predictedDeepCCS 1.0 (2019) [M+H]+ 178.91948 predictedDeepCCS 1.0 (2019) [M+Na]+ 185.97278 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein group
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Antagonist
- General Function
- Voltage-gated cation channel activity
- Specific Function
- NMDA receptor subtype of glutamate-gated ion channels with high calcium permeability and voltage-dependent sensitivity to magnesium. Mediated by glycine. This protein plays a key role in synaptic p...
Components:
References
- Warach S, Kaufman D, Chiu D, Devlin T, Luby M, Rashid A, Clayton L, Kaste M, Lees KR, Sacco R, Fisher M: Effect of the Glycine Antagonist Gavestinel on cerebral infarcts in acute stroke patients, a randomized placebo-controlled trial: The GAIN MRI Substudy. Cerebrovasc Dis. 2006;21(1-2):106-11. Epub 2005 Dec 9. [Article]
Enzymes
1. DetailsUDP-glucuronosyltransferase 1-1
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Steroid binding
- Specific Function
- UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the...
- Gene Name
- UGT1A1
- Uniprot ID
- P22309
- Uniprot Name
- UDP-glucuronosyltransferase 1-1
- Molecular Weight
- 59590.91 Da
References
- Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [Article]
2. DetailsUDP-glucuronosyltransferase 1-3
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Retinoic acid binding
- Specific Function
- UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. Isoform 2 lacks transferase activity but acts as a negative reg...
- Gene Name
- UGT1A3
- Uniprot ID
- P35503
- Uniprot Name
- UDP-glucuronosyltransferase 1-3
- Molecular Weight
- 60337.835 Da
References
- Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [Article]
3. DetailsUDP-glucuronosyltransferase 1-9
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Retinoic acid binding
- Specific Function
- UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform has specificity for phenols. Isoform 2 lacks trans...
- Gene Name
- UGT1A9
- Uniprot ID
- O60656
- Uniprot Name
- UDP-glucuronosyltransferase 1-9
- Molecular Weight
- 59940.495 Da
References
- Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [Article]
4. DetailsUDP-glucuronosyltransferase 2B4
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Glucuronosyltransferase activity
- Specific Function
- UDPGTs are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isozyme is active on polyhydroxylated estrogens (such as...
- Gene Name
- UGT2B4
- Uniprot ID
- P06133
- Uniprot Name
- UDP-glucuronosyltransferase 2B4
- Molecular Weight
- 60512.035 Da
References
- Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [Article]
Drug created at August 31, 2010 21:30 / Updated at February 21, 2021 18:52