ATIGLIFLOZIN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C18H22O7S
Molecular Weight	382.428
Optical Activity	UNSPECIFIED
Defined Stereocenters	5 / 5
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COC1=CC=C(CC2=C(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)C=CS2)C=C1

InChI

InChIKey=BUXGTLNOWLNUKF-SOVHRIKKSA-N

InChI=1S/C18H22O7S/c1-23-11-4-2-10(3-5-11)8-14-12(6-7-26-14)24-18-17(22)16(21)15(20)13(9-19)25-18/h2-7,13,15-22H,8-9H2,1H3/t13-,15-,16+,17-,18-/m1/s1

HIDE SMILES / InChI

Molecular Formula	C18H22O7S
Molecular Weight	382.428
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	5 / 5
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/19137908 | https://www.ncbi.nlm.nih.gov/pubmed/25230708

Atigliflozin (also known as AVE2268), a substituted glycopyranoside, is a selective inhibitor of sodium-dependent glucose transporter 2. This drug reached phase II clinical trials as a new antidiabetic drug for the treatment of type 2 diabetes but further development was discontinued.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Sodium/glucose cotransporter 2 25 Target ID: P31639 Gene ID: 6524.0 Gene Symbol: SLC5A2 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/19137908	Inhibitor 8297		13.0 nM [IC50]

PubMed

Title	Date	PubMed
Effects of AVE2268, a substituted glycopyranoside, on urinary glucose excretion and blood glucose in mice and rats.	2008	19137908
Sodium-glucose cotransport inhibitors: mechanisms, metabolic effects and implications for the treatment of diabetic patients with chronic kidney disease.	2015 Aug	25230708

Substance Class	Chemical Created by `admin` on `Fri Dec 15 17:18:45 GMT 2023` Edited by `admin` on `Fri Dec 15 17:18:45 GMT 2023`
Record UNII	Y0H7UPE4WJ
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ATIGLIFLOZIN

Official Name

English

AVE-2268

Code

English

Atigliflozin [WHO-DD]

Common Name

English

AVE2268

Code

English

2-((4-METHOXYPHENYL)METHYL)THIOPHEN-3-YL-.BETA.-D-GLUCOPYRANOSIDE

Common Name

English

atigliflozin [INN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C98083