Acotiamide - 10mM in DMSO , CAS No.185106-16-5

CAS: 185106-16-5 Cat. No.: A422268 Molecular Weight: 450.55

GRADE & PURITY 10mM in DMSO

Synonyms

N-(2-(BIS(1-METHYLETHYL)AMINO)ETHYL)-2-((2-HYDROXY-4,5-DIMETHOXYBENZOYL)AMINO)THIAZOLE-4-CARBOXAMIDE | UNII-D42OWK5383 | YM443; YM-443; YM 443; Z338; Z-338; Z 338 | AC-27642 | AC1NQZWJ | HY-121467 | N-[2-(diisopropylamino)ethyl]-2-[(2-hydroxy-4,5-dimethox

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

Overview

Information

Acotiamide (Acofide, Z388) is a novelacetylcholinesteraseinhibitor with fundus-relaxing and gastroprokinetic properties.

Targets

AChE 3 μM

In vitro

Acotiamide inhibited recombinant human and canine stomach-derived acetylcholinesterase (AChE) activity in vitro. The mode of the AChE inhibitory action of acotiamide was selective and reversible. It shows a mixed-type inhibition toward recombinant human AChE activity. Ki1 (competitive inhibition) and Ki2 values (noncompetitive inhibition) of acotiamide were 610 nM and 2.7 μM, respectively. IC50 values for AChE of acotiamide is 3 μM. IC50 value for BuChE of acotiamide is >1.0 × 10⁻³ M. Acotiamide inhibited AChE selectively, and the ratio of the IC50 value for BuChE to AChE was more than 330. Acotiamide has no affinity for α2-adrenoceptor, dopamine D2S receptor, or serotonin 5-HT4 receptors, including 5-HT4c, 5-HT4d, or 5-HT4e receptors. In in vitro studies, acotiamide enhanced acetylcholine- but not carbachol-induced contractile responses of guinea pig gastric antrum strips.

In vivo

Acotiamide stimulates gastric motility and improves gastric motility dysfunction in rats by inhibiting AChE activity. It improves stress-induced delayed gastric emptying in rats. Acotiamide also enhances gastric motility by inhibiting AChE activity without affecting QT interval in dogs.

Specifications

Synonyms

N-(2-(BIS(1-METHYLETHYL)AMINO)ETHYL)-2-((2-HYDROXY-4, 5-DIMETHOXYBENZOYL)AMINO)THIAZOLE-4-CARBOXAMIDE | UNII-D42OWK5383 | YM443; YM-443; YM 443; Z338; Z-338; Z 338 | AC-27642 | AC1NQZWJ | HY-121467 | N-[2-(diisopropylamino)ethyl]-2-[(2-hydroxy-4, 5-dimethox

Specifications & Purity

10mM in DMSO

Biochemical and Physiological Mechanisms

Acotiamide (Acofide, Z388) is a novel acetylcholinesterase inhibitor with fundus-relaxing and gastroprokinetic properties.

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

This product requires cold chain shipping. Ground and other economy services are not available.

Product Properties

• ALogP: 2.565
• hba_count: 5
• HBD Count: 3
• Rotatable Bond: 10

Names and Identifiers

• Canonical Smiles: CC(C)N(CCNC(=O)C1=CSC(=N1)NC(=O)C2=CC(=C(C=C2O)OC)OC)C(C)C
• IUPAC Name: N-[2-[di(propan-2-yl)amino]ethyl]-2-[(2-hydroxy-4,5-dimethoxybenzoyl)amino]-1,3-thiazole-4-carboxamide
• InChIKey: TWHZNAUBXFZMCA-UHFFFAOYSA-N
• INCHI: 1S/C21H30N4O5S/c1-12(2)25(13(3)4)8-7-22-20(28)15-11-31-21(23-15)24-19(27)14-9-17(29-5)18(30-6)10-16(14)26/h9-13,26H,7-8H2,1-6H3,(H,22,28)(H,23,24,27)
• Isomeric SMILES: CC(C)N(CCNC(=O)C1=CSC(=N1)NC(=O)C2=CC(=C(C=C2O)OC)OC)C(C)C
• Molecular Weight: 450.55
• Reaxy-Rn: 10117732
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=10117732&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Class Benzene and substituted derivatives
      • Subclass Benzoic acids and derivatives
        • Level5 Hydroxybenzoic acid derivatives
          • Level6 Salicylic acid and derivatives
            • Level7 Salicylamides

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Class: Benzene and substituted derivatives
• Subclass: Benzoic acids and derivatives
• Intermediate Tree Nodes: Hydroxybenzoic acid derivatives - Salicylic acid and derivatives
• Direct Parent: Salicylamides
• Alternative Parents: Methoxyphenols Dimethoxybenzenes 4-alkoxyphenols Benzamides Thiazolecarboxamides Phenoxy compounds 2-heteroaryl carboxamides Benzoyl derivatives Anisoles 1-hydroxy-2-unsubstituted benzenoids 2,4-disubstituted thiazoles Alkyl aryl ethers Vinylogous acids Heteroaromatic compounds Trialkylamines Secondary carboxylic acid amides Amino acids and derivatives Azacyclic compounds Organic oxides Hydrocarbon derivatives Organopnictogen compounds
• Molecular Framework: Aromatic heteromonocyclic compounds
• Substituents: Salicylamide - Dimethoxybenzene - O-dimethoxybenzene - Methoxyphenol - Benzamide - 4-alkoxyphenol - Anisole - Thiazolecarboxylic acid or derivatives - Benzoyl - Phenol ether - Methoxybenzene - Phenoxy compound - 2-heteroaryl carboxamide - Thiazolecarboxamide - 1-hydroxy-2-unsubstituted benzenoid - 2,4-disubstituted 1,3-thiazole - Phenol - Alkyl aryl ether - Azole - Heteroaromatic compound - Vinylogous acid - Thiazole - Amino acid or derivatives - Tertiary aliphatic amine - Tertiary amine - Secondary carboxylic acid amide - Carboxamide group - Organoheterocyclic compound - Azacycle - Ether - Carboxylic acid derivative - Amine - Hydrocarbon derivative - Organic oxide - Organic nitrogen compound - Organopnictogen compound - Organic oxygen compound - Organonitrogen compound - Organooxygen compound - Aromatic heteromonocyclic compound
• Description: This compound belongs to the class of organic compounds known as salicylamides. These are carboxamide derivatives of salicylic acid. Salicylic acid is the ortho-hydroxylated derivative of benzoic acid.
• External Descriptors: salicylamides

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Chemical and Physical Properties

• DMSO(mg / mL) Max Solubility: 90
• DMSO(mM) Max Solubility: 199.755854
• Water(mg / mL) Max Solubility: ＜1
• Molecular Weight: 450.600 g/mol
• XLogP3: 3.500
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 10
• Exact Mass: 450.194 Da
• Monoisotopic Mass: 450.194 Da
• Topological Polar Surface Area: 141.000 Ų
• Heavy Atom Count: 31
• Formal Charge: 0
• Complexity: 586.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1