Gavestinel

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
Thumb
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

Pharmacology
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Drug Discovery
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Contraindications & Blackbox Warnings
Contraindications
Contraindications & Blackbox Warnings
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Our Blackbox Warnings cover Risks, Contraindications, and Adverse Effects
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UGlutamate (NMDA) receptor
antagonist
Humans
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
Medicalerrors
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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.
DrugInteraction
AdenineThe metabolism of Gavestinel can be decreased when combined with Adenine.
AmitriptylineThe metabolism of Gavestinel can be decreased when combined with Amitriptyline.
AtazanavirThe metabolism of Gavestinel can be decreased when combined with Atazanavir.
CarbamazepineThe metabolism of Gavestinel can be increased when combined with Carbamazepine.
DacomitinibThe metabolism of Gavestinel can be decreased when combined with Dacomitinib.
DasabuvirThe metabolism of Gavestinel can be decreased when combined with Dasabuvir.
DeferasiroxThe metabolism of Gavestinel can be decreased when combined with Deferasirox.
DesogestrelThe metabolism of Gavestinel can be increased when combined with Desogestrel.
DiflunisalThe metabolism of Gavestinel can be decreased when combined with Diflunisal.
EfavirenzThe metabolism of Gavestinel can be increased when combined with Efavirenz.
Interactions
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Food Interactions
Not Available

Products

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Product Ingredients
IngredientUNIICASInChI Key
Gv 150526a80W7787JVB153436-38-5GRSDSTMFQHAESM-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
  1. 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]
PubChem Compound
6450546
PubChem Substance
347827789
ChemSpider
4953148
BindingDB
50010475
ChEMBL
CHEMBL44793
ZINC
ZINC000003797383
Wikipedia
Gavestinel
MSDS
Download (608 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

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
PropertyValueSource
Water Solubility0.0012 mg/mLALOGPS
logP4.18ALOGPS
logP4.45ChemAxon
logS-5.5ALOGPS
pKa (Strongest Acidic)5.04ChemAxon
pKa (Strongest Basic)-2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area82.19 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity99.17 m3·mol-1ChemAxon
Polarizability36.97 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Targets

Drugtargets
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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
  1. 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

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
  1. 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]
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
  1. 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]
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
  1. 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]
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
  1. 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 on August 31, 2010 21:30 / Updated on February 21, 2021 18:52