SOTAGLIFLOZIN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C21H25ClO5S
Molecular Weight	424.938
Optical Activity	UNSPECIFIED
Defined Stereocenters	5 / 5
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCOC1=CC=C(CC2=C(Cl)C=CC(=C2)[C@@H]3O[C@H](SC)[C@@H](O)[C@H](O)[C@H]3O)C=C1

InChI

InChIKey=QKDRXGFQVGOQKS-CRSSMBPESA-N

InChI=1S/C21H25ClO5S/c1-3-26-15-7-4-12(5-8-15)10-14-11-13(6-9-16(14)22)20-18(24)17(23)19(25)21(27-20)28-2/h4-9,11,17-21,23-25H,3,10H2,1-2H3/t17-,18-,19+,20+,21-/m1/s1

HIDE SMILES / InChI

Molecular Formula	C21H25ClO5S
Molecular Weight	424.938
Charge	0
Count

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

Description
Sources: http://www.lexpharma.com/pipeline/sotagliflozin | https://www.ncbi.nlm.nih.gov/pubmed/25690134

Sotagliflozin (LX4211) is an orally-delivered small molecule compound that is currently in development for the treatment of type 1 and type 2 diabetes mellitus. Sotagliflozin (LX4211) inhibits both sodium-glucose cotransporter type 2, or SGLT2, a transporter responsible for most of the glucose reabsorption performed by the kidney, and sodium-glucose cotransporter type 1, or SGLT1, a transporter responsible for glucose and galactose absorption in the gastrointestinal tract, and to a lesser extent than SGLT2, glucose reabsorption in the kidney. Combining SGLT1 and SGLT2 inhibition in a single molecule would provide complementary insulin-independent mechanisms to treat diabetes.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Sodium/glucose cotransporter 1 7 Target ID: CHEMBL4979 Sources: http://www.lexpharma.com/pipeline/sotagliflozin	Inhibitor 8297		36.0 nM [IC50]
Sodium/glucose cotransporter 2 25 Target ID: CHEMBL3884 Sources: http://www.lexpharma.com/pipeline/sotagliflozin	Inhibitor 8297		1.8 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Type 1 diabetes mellitus 17 Sources: http://www.lexpharma.com/pipeline/sotagliflozin	Primary		Phase III 656	SOTAGLIFLOZIN Approved Use Unknown
Type 2 diabetes mellitus 259 Sources: http://www.lexpharma.com/pipeline/sotagliflozin	Primary		Phase III 656	SOTAGLIFLOZIN Approved Use Unknown

C_max

Value	Dose	Analyte	Population
274 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25529979/	400 mg 1 times / day multiple, oral dose: 400 mg route of administration: Oral experiment type: MULTIPLE co-administered:	SOTAGLIFLOZIN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
180 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25529979/	400 mg 1 times / day multiple, oral dose: 400 mg route of administration: Oral experiment type: MULTIPLE co-administered:	SOTAGLIFLOZIN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
291 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22739142/	300 mg 1 times / day steady-state, oral dose: 300 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	SOTAGLIFLOZIN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
113 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22739142/	150 mg 1 times / day steady-state, oral dose: 150 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	SOTAGLIFLOZIN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

AUC

Value	Dose	Analyte	Population
2879 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25529979/	400 mg 1 times / day multiple, oral dose: 400 mg route of administration: Oral experiment type: MULTIPLE co-administered:	SOTAGLIFLOZIN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
2213 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25529979/	400 mg 1 times / day multiple, oral dose: 400 mg route of administration: Oral experiment type: MULTIPLE co-administered:	SOTAGLIFLOZIN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
1752 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22739142/	300 mg 1 times / day steady-state, oral dose: 300 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	SOTAGLIFLOZIN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
732 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22739142/	150 mg 1 times / day steady-state, oral dose: 150 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	SOTAGLIFLOZIN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
18.1 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25529979/	400 mg 1 times / day multiple, oral dose: 400 mg route of administration: Oral experiment type: MULTIPLE co-administered:		SOTAGLIFLOZIN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
16.6 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25529979/	400 mg 1 times / day multiple, oral dose: 400 mg route of administration: Oral experiment type: MULTIPLE co-administered:		SOTAGLIFLOZIN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

Sourcing

Vendor/Aggregator	ID	URL
001 Chemical	DY34062	https://www.001chemical.com/chem/search?q=DY34062
1PlusChem LLC	1P0006AV	https://www.1pchem.com/search?query=1P0006AV
AChemBlock	G-5684	http://www.achemblock.com/catalogsearch/result/?q=G-5684
AK Scientific	3792AH	https://aksci.com/item_detail.php?cat=3792AH
Ambeed	A225622	http://www.ambeed.com/search/Search.html?keyword=A225622
Angene	AGN-PC-0WAJQS	http://www.angenechemical.com/productshow/AGN-PC-0WAJQS.html
AstaTech	42259	http://astatechinc.com/CPSResult.php?CRNO=42259
BLD Pharm	BD300361	http://www.bldpharm.com/search/Search.html?keyword=BD300361
Capot Chemical	28207	https://www.capotchem.com/search.do?q=28207
Cayman Chemical	19141	http://www.caymanchem.com/app/template/Product.vm/catalog/19141
Chem Scene	CS-1069	http://www.chemscene.com/goproductList/searchProductList?productObj=CS-1069
ChemShuttle	139084	https://www.chemshuttle.com/catalogsearch/result/?q=139084
Combi-Blocks	QJ-8153	http://www.combi-blocks.com/cgi-bin/find.cgi?QJ-8153
Coresyn	CM11080	http://www.coresyn.com/search.do?q=CM11080
KeyOrganics	AS-35202	http://www.keyorganicsinc.com/bionet/catalogsearch/result?q=AS-35202
Lab Seeker	SC-94335	http://www.labseeker.com/search.php?keywords=SC-94335&category=0
LabSeeker	SC-94335	http://www.labseeker.com/search.php?keywords=SC-94335&category=0
MedChem Express	HY-15516	https://www.medchemexpress.com/search.html?q=HY-15516&ft=&fa=&fp=
MolPort	MolPort-038-387-811	https://www.molport.com/shop/molecule-link/MolPort-038-387-811
Molcore	MC34062	http://www.molcore.com/CatMC34062.html
Molnova	M10090	https://www.molnova.com/en/serch-list.html?keywords=M10090
Selleck Chemicals	S8103	http://www.selleckchem.com/search.html?searchDTO.searchParam=S8103
Synthonix	10525	https://synthonix.com/catalogsearch/result/?q=10525
TargetMol	T3547	https://www.targetmol.com/search?keyword=T3547
Tetrahedron	TS87955	http://www.thsci.com/search.do?q=TS87955
eMolecules	44811286	https://orderbb.emolecules.com/search/#?query=44811286
eNovation Chemicals	D495893	https://www.enovationchem.com/Products.asp?SEARCHTEXT=D495893&searchbtn.x=0&searchbtn.y=0
mcule	MCULE-1909586706	https://mcule.com/MCULE-1909586706/
mcule	MCULE-8895935983	https://mcule.com/MCULE-8895935983/

PubMed

Title	Date	PubMed
LX4211, a dual SGLT1/SGLT2 inhibitor, improved glycemic control in patients with type 2 diabetes in a randomized, placebo-controlled trial.	2012 Aug	22739142
Development of sotagliflozin, a dual sodium-dependent glucose transporter 1/2 inhibitor.	2015 Mar	25690134

Patents

Sample Use Guides

In Vivo Use Guide

Sotagliflozin (LX4211) at 400 mg once daily for 7 days.

Route of Administration: Oral

In Vitro Use Guide

The ability of sotagliflozin in vitro to inhibit sodium-dependent glucose transporters 1 and 2 (SGLT1 and SGLT2) was established. Sotagliflozin inhibited SGLT2 with an IC50 of 0.0018 uΜ, and it inhibited SGLT1 with an IC50 of 0.036 uM.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 01:31:17 GMT 2023` Edited by `admin` on `Sat Dec 16 01:31:17 GMT 2023`
Record UNII	6B4ZBS263Y
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

SOTAGLIFLOZIN

Official Name

English

SOTAGLIFLOZIN [MI]

Common Name

English

LP-802034

Code

English

LX-4211

Code

English

INPEFA

Brand Name

English

Sotagliflozin [WHO-DD]

Common Name

English

SAR-439954

Common Name

English

sotagliflozin [INN]

Common Name

English

METHYL (5S)-5-C-(4-CHLORO-3-((4-ETHOXYPHENYL)METHYL)PHENYL)-1-THIO-.BETA.-L-XYLOPYRANOSIDE

Systematic Name

English

SAR439954

Common Name

English

.BETA.-L-XYLOPYRANOSIDE, METHYL 5-C-(4-CHLORO-3-((4-ETHOXYPHENYL)METHYL)PHENYL)-1-THIO-, (5S)-

Common Name

English

LX4211

Code

English

SOTAGLIFLOZIN [USAN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C98083