Gantacurium Chloride

Identification

Name
Gantacurium Chloride
Accession Number
DB05710
Type
Small Molecule
Groups
Investigational
Description

Gantacurium Chloride is a new, investigational, non-depolarizing ultra-short acting neuromuscular blocker. It is being developed by Avera Pharmaceuticals.

Structure
Thumb
Synonyms
  • AV430A
External IDs
AV-4430A / GW-280430 / GW-280430A / GW280430A
Categories
UNII
LEY8QK99UR
CAS number
213998-46-0
Weight
Average: 1064.49
Monoisotopic: 1062.381438
Chemical Formula
C53H69Cl3N2O14
InChI Key
SDIFKXLSGXCGEN-WJUBNSBASA-L
InChI
InChI=1S/C53H69ClN2O14.2ClH/c1-55(19-15-34-26-41(59-3)43(61-5)30-37(34)40(55)23-33-24-45(63-7)51(67-11)46(25-33)64-8)17-13-22-70-53(58)39(54)32-49(57)69-21-14-18-56(2)20-16-35-27-42(60-4)44(62-6)31-38(35)50(56)36-28-47(65-9)52(68-12)48(29-36)66-10;;/h24-32,40,50H,13-23H2,1-12H3;2*1H/q+2;;/p-2/b39-32-;;/t40-,50+,55-,56+;;/m1../s1
IUPAC Name
(1S,2R)-2-(3-{[(2Z)-3-chloro-4-{3-[(1R,2S)-6,7-dimethoxy-2-methyl-1-[(3,4,5-trimethoxyphenyl)methyl]-1,2,3,4-tetrahydroisoquinolin-2-ium-2-yl]propoxy}-4-oxobut-2-enoyl]oxy}propyl)-6,7-dimethoxy-2-methyl-1-(3,4,5-trimethoxyphenyl)-1,2,3,4-tetrahydroisoquinolin-2-ium dichloride
SMILES
[Cl-].[Cl-].COC1=CC(C[C@@H]2C3=CC(OC)=C(OC)C=C3CC[N@@+]2(C)CCCOC(=O)C(\Cl)=C\C(=O)OCCC[N@@+]2(C)CCC3=CC(OC)=C(OC)C=C3[C@@H]2C2=CC(OC)=C(OC)C(OC)=C2)=CC(OC)=C1OC

Pharmacology

Indication

Investigated for use/treatment in anesthesia (unspecified).

Pharmacodynamics

Gantacurium chloride administered to anesthetized and ventilated healthy volunteers, caused dose dependent transient decrease in arterial blood pressure, mild histamine release at higher doses and no consistent changes in pulmonary compliance.

Mechanism of action
TargetActionsOrganism
ANeuronal acetylcholine receptor subunit alpha-3
antagonist
Human
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism

The pharmacokinetic parameters are consistent with in situ rapid inactivation by plasma cysteine.

Route of elimination
Not Available
Half life

3.09±0.21 minutes

Clearance
Not Available
Toxicity
Not Available
Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
  1. Heerdt PM, Kang R, The' A, Hashim M, Mook RJ Jr, Savarese JJ: Cardiopulmonary effects of the novel neuromuscular blocking drug GW280430A (AV430A) in dogs. Anesthesiology. 2004 Apr;100(4):846-51. [PubMed:15087619]
  2. Savarese JJ, Belmont MR, Hashim MA, Mook RA Jr, Boros EE, Samano V, Patel SS, Feldman PL, Schultz JA, McNulty M, Spitzer T, Cohn DL, Morgan P, Wastila WB: Preclinical pharmacology of GW280430A (AV430A) in the rhesus monkey and in the cat: a comparison with mivacurium. Anesthesiology. 2004 Apr;100(4):835-45. [PubMed:15087618]
External Links
PubChem Compound
10772467
PubChem Substance
347827738
ChemSpider
8947782
ChEMBL
CHEMBL275321
Wikipedia
Gantacurium_chloride

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1, 2CompletedTreatmentHealthy Volunteers1

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 Solubility2.9e-05 mg/mLALOGPS
logP4.58ALOGPS
logP-1.3ChemAxon
logS-7.6ALOGPS
pKa (Strongest Acidic)17.91ChemAxon
pKa (Strongest Basic)-4.1ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area144.9 Å2ChemAxon
Rotatable Bond Count25ChemAxon
Refractivity290.33 m3·mol-1ChemAxon
Polarizability107.61 Å3ChemAxon
Number of Rings6ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
Not Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as benzylisoquinolines. These are organic compounds containing an isoquinoline to which a benzyl group is attached.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Isoquinolines and derivatives
Sub Class
Benzylisoquinolines
Direct Parent
Benzylisoquinolines
Alternative Parents
1-phenyltetrahydroisoquinolines / Phenoxy compounds / Anisoles / Methoxybenzenes / Alkyl aryl ethers / Aralkylamines / Fatty acid esters / Dicarboxylic acids and derivatives / Vinylogous halides / Tetraalkylammonium salts
show 12 more
Substituents
Benzylisoquinoline / 1-phenyltetrahydroisoquinoline / Tetrahydroisoquinoline / Phenoxy compound / Phenol ether / Anisole / Methoxybenzene / Alkyl aryl ether / Aralkylamine / Fatty acid ester
show 34 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Antagonist
General Function
Ligand-gated ion channel activity
Specific Function
After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane.
Gene Name
CHRNA3
Uniprot ID
P32297
Uniprot Name
Neuronal acetylcholine receptor subunit alpha-3
Molecular Weight
57479.54 Da
References
  1. Khirwadkar R, Hunter JM: Neuromuscular physiology and pharmacology: an update Continuing Education in Anaesthesia Critical Care & Pain. 2012 May 24;12(5):237–244.

Drug created on November 18, 2007 11:27 / Updated on July 02, 2018 18:28