Details of the Drug

General Information of Drug (ID: DMMLXA9)

Drug Name
LX-4211
Synonyms
Sotagliflozin; 1018899-04-1; LX-4211; LX4211; UNII-6B4ZBS263Y; 6B4ZBS263Y; AK170751; (2s,3r,4r,5s,6r)-2-(4-chloro-3-(4-ethoxybenzyl)phenyl)-6-(methylthio)tetrahydro-2h-pyran-3,4,5-triol; b-L-Xylopyranoside, methyl 5-C-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-1-thio-, (5S)-;b-L-Xylopyranoside, methyl 5-C-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-1-thio-, (5S)-; Sotagliflozin [USAN:INN]; beta-l-Xylopyranoside, methyl 5-C-(4-chloro-3-((4-ethoxyphenyl)methyl)phenyl)-1-thio-, (5S)-; LX 4211; Tube103; LP 802034
Indication
Disease Entry ICD 11 Status REF
Cardiovascular disease BA00-BE2Z Phase 3 [1]
Type-1 diabetes 5A10 Phase 3 [2], [3]
Type-2 diabetes 5A11 Phase 3 [3]
Drug Type
Small molecular drug
Structure
3D MOL is unavailable 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 424.9
Topological Polar Surface Area (xlogp) 3.2
Rotatable Bond Count (rotbonds) 6
Hydrogen Bond Donor Count (hbonddonor) 3
Hydrogen Bond Acceptor Count (hbondacc) 6
Chemical Identifiers
Formula
C21H25ClO5S
IUPAC Name
(2S,3R,4R,5S,6R)-2-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-6-methylsulfanyloxane-3,4,5-triol
Canonical SMILES
CCOC1=CC=C(C=C1)CC2=C(C=CC(=C2)[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)SC)O)O)O)Cl
InChI
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
InChIKey
QKDRXGFQVGOQKS-CRSSMBPESA-N
Cross-matching ID
PubChem CID
24831714
CAS Number
1018899-04-1
DrugBank ID
DB12713
TTD ID
D0U7IL
VARIDT ID
DR01138

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Sodium/glucose cotransporter 1 (SGLT1) TT2UE56 SC5A1_HUMAN Modulator [4]
Sodium/glucose cotransporter 2 (SGLT2) TTLWPVF SC5A2_HUMAN Modulator [4], [5]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease Cardiovascular disease
ICD Disease Classification BA00-BE2Z
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Sodium/glucose cotransporter 1 (SGLT1) DTT SLC5A1 9.67E-01 0.08 0.42
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

References

1 Clinical pipeline report, company report or official report of the Pharmaceutical Research and Manufacturers of America (PhRMA)
2 Clinical pipeline report, company report or official report of the Pharmaceutical Research and Manufacturers of America (PhRMA)
3 Clinical pipeline report, company report or official report of the Pharmaceutical Research and Manufacturers of America (PhRMA)
4 LX4211, a dual SGLT1/SGLT2 inhibitor, improved glycemic control in patients with type 2 diabetes in a randomized, placebo-controlled trial. Clin Pharmacol Ther. 2012 Aug;92(2):158-69.
5 Risk factors for post-traumatic pneumonia in patients with retained haemothorax: results of a prospective, observational AAST study.Injury.2013 Sep;44(9):1159-64.
6 2014 FDA drug approvals. Nat Rev Drug Discov. 2015 Feb;14(2):77-81.
7 Radium 223 dichloride for prostate cancer treatment. Drug Des Devel Ther. 2017 Sep 6;11:2643-2651.
8 Dose-ranging efficacy and safety study of ertugliflozin, a sodium-glucose co-transporter 2 inhibitor, in patients with type 2 diabetes on a background of metformin.Diabetes Obes Metab.2015 Jun;17(6):591-8.
9 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services.
10 Ipragliflozin: A novel sodium-glucose cotransporter 2 inhibitor developed in Japan.World J Diabetes.2015 Feb 15;6(1):136-44.
11 Effects of AVE2268, a substituted glycopyranoside, on urinary glucose excretion and blood glucose in mice and rats. Arzneimittelforschung. 2008;58(11):574-80.
12 Pharmacological Characterization of YM543, a Newly Synthesized, Orally Active SGLT2 Selective Inhibitor. Endocr Res. 2013 Aug;38(3):168-183.
13 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Target id: 915).
14 Clinical pipeline report, company report or official report of GlaxoSmithKline (2009).
15 Clinical pipeline report, company report or official report of Lexicon Pharmaceuticals.
16 T-1095, an inhibitor of renal Na+-glucose cotransporters, may provide a novel approach to treating diabetes. Diabetes. 1999 Sep;48(9):1794-800.
17 Na+-glucose cotransporter (SGLT) inhibitory flavonoids from the roots of Sophora flavescens. Bioorg Med Chem. 2007 May 15;15(10):3445-9.
18 Alstiphyllanines E-H, picraline and ajmaline-type alkaloids from Alstonia macrophylla inhibiting sodium glucose cotransporter. Bioorg Med Chem. 2010 Mar 15;18(6):2152-2158.