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Details

Stereochemistry ABSOLUTE
Molecular Formula C16H14F3N3O2S
Molecular Weight 369.361
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DEXLANSOPRAZOLE

SMILES

CC1=C(OCC(F)(F)F)C=CN=C1C[S@@+]([O-])C2=NC3=C(N2)C=CC=C3

InChI

InChIKey=MJIHNNLFOKEZEW-RUZDIDTESA-N
InChI=1S/C16H14F3N3O2S/c1-10-13(20-7-6-14(10)24-9-16(17,18)19)8-25(23)15-21-11-4-2-3-5-12(11)22-15/h2-7H,8-9H2,1H3,(H,21,22)/t25-/m1/s1

HIDE SMILES / InChI

Description

Dexlansoprazole (trade names Kapidex, Dexilant) is a proton pump inhibitor (PPI) that is marketed by Takeda Pharmaceuticals for the treatment of erosive esophagitis and gastro-oesophageal reflux disease. Dexlansoprazole is used to heal and maintain healing of erosive esophagitis and to treat heartburn associated with gastroesophageal reflux disease (GERD). It lasts longer than lansoprazole, to which it is chemically related, and needs to be taken less often. Dexlansoprazole is supplied for oral administration as a dual delayed-release formulation in capsules and orally disintegrating tablets. The capsules and tablets contain dexlansoprazole in a mixture of two types of enteric-coated granules with different pH-dependent dissolution profiles. The most significant adverse reactions (≥2%) reported in clinical trials were diarrhea, abdominal pain, nausea, upper respiratory tract infection, vomiting, and flatulence.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
DEXILANT
Primary
DEXILANT
PubMed

PubMed

TitleDatePubMed
Enantioselective disposition of lansoprazole in relation to CYP2C19 genotypes in the presence of fluvoxamine.
2005 Jul
Effect of clarithromycin on the enantioselective disposition of lansoprazole in relation to CYP2C19 genotypes.
2005 Jun
Comparison of enantioselective disposition of rabeprazole versus lansoprazole in renal-transplant recipients who are CYP2C19 extensive metabolizers.
2005 May
Influence of ABCB1 C3435T polymorphism on the pharmacokinetics of lansoprazole and gastroesophageal symptoms in Japanese renal transplant recipients classified as CYP2C19 extensive metabolizers and treated with tacrolimus.
2006 Dec
Intestinal CYP3A4 is not involved in the enantioselective disposition of lansoprazole.
2006 Jan
Enantioselective disposition of lansoprazole and rabeprazole in human plasma.
2006 Jun
Estimation of the area under the concentration-time curve of racemic lansoprazole by using limited plasma concentration of lansoprazole enantiomers.
2008 May
Delayed release dexlansoprazole in the treatment of GERD and erosive esophagitis.
2009
Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development.
2009
New insights into the structural features and functional relevance of human cytochrome P450 2C9. Part II.
2009 Dec
Patents

Sample Use Guides

In Vivo Use Guide
For erosive esophagitis: One 60 mg capsule once daily for up to 8 weeks Relief of Heartburn: One 30 mg capsule once daily
Route of Administration: Oral
In Vitro Use Guide
A stably transfected gene reporter cell line AZ-AHR, derived from human hepatoma HepG2 cells transfected with a construct containing several AhR binding sites upstream of a luciferase reporter gene, was used for assessment of AhR transcriptional activity. Cells were incubated for 24 h with DEXLANSOPRAZOLE and/or vehicle (DMSO; 0.1% v/v), in the presence or absence of TCDD (10 nM; AZ-AHR cells) or DEX (100 nM; AZ-GR cells). After the treatments, cells were lysed and luciferase activity was measured. In parallel, cell viability was determined by conventional MTT test.
Name Type Language
DEXLANSOPRAZOLE
INN   MART.   ORANGE BOOK   USAN   VANDF   WHO-DD  
USAN   INN  
Official Name English
TAK-390
Code English
1H-BENZIMIDAZOLE, 2-((R)-((3-METHYL-4-(2,2,2-TRIFLUOROETHOXY)-2-PYRIDINYL)METHYL)SULFINYL)-
Systematic Name English
DEXILANT
Brand Name English
T-168390
Code English
DEXLANSOPRAZOLE [INN]
Common Name English
LANSOPRAZOLE, (R)-
Common Name English
DEXLANSOPRAZOLE [VANDF]
Common Name English
DEXILANT SOLUTAB
Brand Name English
DEXLANSOPRAZOLE [WHO-DD]
Common Name English
KAPIDEX
Brand Name English
2-((R)-((3-METHYL-4-(2,2,2-TRIFLUOROETHOXY)-2-PYRIDINYL)METHYL)SULFINYL)-1H-BENZIMIDAZOLE
Systematic Name English
DEXLANSOPRAZOLE [MART.]
Common Name English
LANSOPRAZOLE R-FORM
MI  
Common Name English
LANSOPRAZOLE R-FORM [MI]
Common Name English
(+)-2-((R)-((3-METHYL-4-(2,2,2-TRIFLUOROETHOXY)PYRIDIN-2-YL)METHYL)SULFINYL)-1H-BENZIMIDAZOLE
Systematic Name English
DEXLANSOPRAZOLE [USAN]
Common Name English
(R)-LANSOPRAZOLE
Common Name English
DEXLANSOPRAZOLE [ORANGE BOOK]
Common Name English
Classification Tree Code System Code
NDF-RT N0000000147
Created by admin on Tue Mar 06 11:23:02 UTC 2018 , Edited by admin on Tue Mar 06 11:23:02 UTC 2018
WHO-VATC QA02BC06
Created by admin on Tue Mar 06 11:23:02 UTC 2018 , Edited by admin on Tue Mar 06 11:23:02 UTC 2018
WHO-ATC A02BC06
NDF-RT N0000175525
Created by admin on Tue Mar 06 11:23:02 UTC 2018 , Edited by admin on Tue Mar 06 11:23:02 UTC 2018
LIVERTOX 290
Created by admin on Tue Mar 06 11:23:02 UTC 2018 , Edited by admin on Tue Mar 06 11:23:02 UTC 2018
Code System Code Type Description
PUBCHEM
9578005
Created by admin on Tue Mar 06 11:23:02 UTC 2018 , Edited by admin on Tue Mar 06 11:23:02 UTC 2018
PRIMARY SWITZERF
RXCUI
816346
Created by admin on Tue Mar 06 11:23:02 UTC 2018 , Edited by admin on Tue Mar 06 11:23:02 UTC 2018
PRIMARY RxNorm
EVMPD
SUB31929
Created by admin on Tue Mar 06 11:23:02 UTC 2018 , Edited by admin on Tue Mar 06 11:23:02 UTC 2018
PRIMARY
CAS
138530-94-6
Created by admin on Tue Mar 06 11:23:02 UTC 2018 , Edited by admin on Tue Mar 06 11:23:02 UTC 2018
PRIMARY
MERCK INDEX
M6683
Created by admin on Tue Mar 06 11:23:02 UTC 2018 , Edited by admin on Tue Mar 06 11:23:02 UTC 2018
PRIMARY Merck Index
NCI_THESAURUS
C73192
Created by admin on Tue Mar 06 11:23:02 UTC 2018 , Edited by admin on Tue Mar 06 11:23:02 UTC 2018
PRIMARY
ChEMBL
CHEMBL1201863
Created by admin on Tue Mar 06 11:23:02 UTC 2018 , Edited by admin on Tue Mar 06 11:23:02 UTC 2018
PRIMARY
IUPHAR
5487
Created by admin on Tue Mar 06 11:23:02 UTC 2018 , Edited by admin on Tue Mar 06 11:23:02 UTC 2018
PRIMARY
INN
8524
Created by admin on Tue Mar 06 11:23:02 UTC 2018 , Edited by admin on Tue Mar 06 11:23:02 UTC 2018
PRIMARY
LactMed
138530-94-6
Created by admin on Tue Mar 06 11:23:02 UTC 2018 , Edited by admin on Tue Mar 06 11:23:02 UTC 2018
PRIMARY
WIKIPEDIA
DEXLANSOPRAZOLE
Created by admin on Tue Mar 06 11:23:02 UTC 2018 , Edited by admin on Tue Mar 06 11:23:02 UTC 2018
PRIMARY