Lapaquistat , CAS No.189059-71-0

CAS: 189059-71-0 Cat. No.: L648651 Molecular Weight: 603.10 PubChem CID: 9960389

Synonyms

SCHEMBL227295 | 2-(1-(2-((3R,5S)-1-(3-hydroxy-2,2-dimethylpropyl)-7-chloro-5-(2,3- dimethoxyphenyl)-2-oxo-1,2,3,5-tetrahydrobenzo(E)(1,4)oxazepin-3-yl)acetyl)piperidin-4-yl)acetic acid | 2-[1-[2-[(3R,5S)-7-chloro-5-(2,3-dimethoxyphenyl)-1-(3-hydroxy-2,2-d

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

Lapaquistat (T-91485), a cholesterol biosynthesis inhibitor, is the active metabolite of Lapaquistat acetate . Lapaquistat can decrease statin-induced myotoxicity in lipid-lowering therapy

In Vitro

Lapaquistat inhibits cholesterol biosynthesis in differentiated RD (rhabdomyosarcoma) cells, with an IC 50 of 36 nM. Lapaquistat potently inhibits cholesterol synthesis in RD cells, with an IC 25 exceeded 100 μM. Lapaquistat concentration-dependently inhibits cholesterol biosynthesis in human skeletal myocytes, with an IC 50 of 45 nM. MCE has not independently confirmed the accuracy of these methods. They are for reference only.

In Vivo

After oral administration to rats, Lapaquistat acetate is absorbed and rapidly hydrolyzed into a pharmacological active metabolite, Lapaquistat . MCE has not independently confirmed the accuracy of these methods. They are for reference only.

Form:Solid

IC50& Target:Cholesterol biosynthesis

Specifications

Synonyms

SCHEMBL227295 | 2-(1-(2-((3R, 5S)-1-(3-hydroxy-2, 2-dimethylpropyl)-7-chloro-5-(2, 3- dimethoxyphenyl)-2-oxo-1, 2, 3, 5-tetrahydrobenzo(E)(1, 4)oxazepin-3-yl)acetyl)piperidin-4-yl)acetic acid | 2-[1-[2-[(3R, 5S)-7-chloro-5-(2, 3-dimethoxyphenyl)-1-(3-hydroxy-2, 2-d

Biochemical and Physiological Mechanisms

Lapaquistat (T-91485), a cholesterol biosynthesis inhibitor, is the active metabolite of Lapaquistat acetate ( HY-16274 ). Lapaquistat can decrease statin-induced myotoxicity in lipid-lowering therapy.

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

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

Names and Identifiers

• Canonical Smiles: CC(C)(CN1C2=C(C=C(C=C2)Cl)C(OC(C1=O)CC(=O)N3CCC(CC3)CC(=O)O)C4=C(C(=CC=C4)OC)OC)CO
• IUPAC Name: 2-[1-[2-[(3R,5S)-7-chloro-5-(2,3-dimethoxyphenyl)-1-(3-hydroxy-2,2-dimethylpropyl)-2-oxo-5H-4,1-benzoxazepin-3-yl]acetyl]piperidin-4-yl]acetic acid
• InChIKey: HDGUKVZPMPJBFK-LEAFIULHSA-N
• INCHI: 1S/C31H39ClN2O8/c1-31(2,18-35)17-34-23-9-8-20(32)15-22(23)28(21-6-5-7-24(40-3)29(21)41-4)42-25(30(34)39)16-26(36)33-12-10-19(11-13-33)14-27(37)38/h5-9,15,19,25,28,35H,10-14,16-18H2,1-4H3,(H,37,38)/t25-,28-/m1/s1
• Isomeric SMILES: CC(C)(CN1C2=C(C=C(C=C2)Cl)[C@H](O[C@@H](C1=O)CC(=O)N3CCC(CC3)CC(=O)O)C4=C(C(=CC=C4)OC)OC)CO
• Alternate CAS: 189059-71-0
• PubChem CID: 9960389
• MeSH Entry Terms: (1-(2-(1-(2-carboxyoxy-1,1-dimethylethyl)-7-chloro-5-(2,3-dimethoxyphenyl)-2-oxo-1,2,3,5-tetrahydrobenzo(e)(1,4)oxazepin-3-yl)acetyl)piperidin-4-yl)acetic acid;1-((1-(3-acetoxy-2,2-dimethylpropyl)-7-chloro-5-(2,3-dimethoxyphenyl)-2-oxo-1,2,3,5-tetrahydro-
• Molecular Weight: 603.10

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Class Benzoxazepines

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Class: Benzoxazepines
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: Benzoxazepines
• Alternative Parents: Dimethoxybenzenes N-acylpiperidines Phenoxy compounds Anisoles Alkyl aryl ethers Aryl chlorides Tertiary carboxylic acid amides Lactams Oxacyclic compounds Azacyclic compounds Monocarboxylic acids and derivatives Carboxylic acids Dialkyl ethers Hydrocarbon derivatives Carbonyl compounds Organic oxides Organochlorides Organonitrogen compounds Primary alcohols
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Benzoxazepine - O-dimethoxybenzene - Dimethoxybenzene - N-acyl-piperidine - Phenoxy compound - Anisole - Methoxybenzene - Phenol ether - Alkyl aryl ether - Aryl chloride - Aryl halide - Monocyclic benzene moiety - Benzenoid - Piperidine - Tertiary carboxylic acid amide - Carboxamide group - Lactam - Oxacycle - Azacycle - Carboxylic acid derivative - Monocarboxylic acid or derivatives - Carboxylic acid - Ether - Dialkyl ether - Organooxygen compound - Organic nitrogen compound - Primary alcohol - Alcohol - Carbonyl group - Organohalogen compound - Organochloride - Hydrocarbon derivative - Organic oxide - Organic oxygen compound - Organonitrogen compound - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as benzoxazepines. These are organic compounds containing a benzene fused to an oxazepine ring (a seven-membered ring with four carbon atoms, one oxygen atom, and a nitrogen atom).
• External Descriptors: Not available

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

Associated Targets(Human)

FDFT1 Tchem Squalene synthase (2 Activities)

Discover Target: FDFT1

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

Associated Targets(non-human)

Fdft1 Squalene synthetase (34 Activities)

Discover Target: Fdft1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Rattus norvegicus (775804 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mechanisms of Action

Chemical and Physical Properties

• Solubility: DMSO : 25 mg/mL (41.45 mM; Need ultrasonic)
• Molecular Weight: 603.100 g/mol
• XLogP3: 3.200
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 10
• Exact Mass: 602.239 Da
• Monoisotopic Mass: 602.239 Da
• Topological Polar Surface Area: 126.000 Ų
• Heavy Atom Count: 42
• Formal Charge: 0
• Complexity: 942.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 2
• 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