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

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
Sotagliflozin as a potential treatment for type 2 diabetes mellitus.	2015	26548423
LX4211 therapy reduces postprandial glucose levels in patients with type 2 diabetes mellitus and renal impairment despite low urinary glucose excretion.	2015 Jan 1	25529979
Sotagliflozin, a Dual SGLT1 and SGLT2 Inhibitor, as Adjunct Therapy to Insulin in Type 1 Diabetes.	2015 Jul	26049551
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.

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