DEXLANSOPRAZOLE

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

SMILES

CC1=C(C[S@@+]([O-])C2=NC3=C(N2)C=CC=C3)N=CC=C1OCC(F)(F)F

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

Molecular Formula	C16H14F3N3O2S
Molecular Weight	369.361
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

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.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Potassium-transporting ATPase 31	Inhibitor 8,297
Potassium-transporting ATPase 31	Inhibitor 8,297
Potassium-transporting ATPase 31	Inhibitor 8,297	5.2 µM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Active duodenal ulcer 6	Primary	Approved 8,429	PREVACID
Gastric ulcer 67	Primary	Approved 8,429	PREVACID
Gastroesophageal reflux disease 59	Primary	Approved 8,429	PREVACID
Erosive esophagitis 7	Primary	Approved 8,429	DEXILANT
Heartburn 24	Curative	Approved 8,429	DEXILANT
Active duodenal ulcer 6	Primary	Approved 8,429	PREVACID
Gastric ulcer 67	Primary	Approved 8,429	PREVACID
Gastroesophageal reflux disease 59	Primary	Approved 8,429	PREVACID

C_max

Value	Dose	Analyte	Population
1705 ng/mL	30 mg single, intravenous	LANSOPRAZOLE plasma	Homo sapiens
691 ng/mL	30 mg 1 times / day multiple, oral	DEXLANSOPRAZOLE plasma	Homo sapiens
1136 ng/mL	60 mg 1 times / day multiple, oral	DEXLANSOPRAZOLE plasma	Homo sapiens
37.3 ng/mL/(mg dose)	15 mg 1 times / day multiple, oral	DEXLANSOPRAZOLE plasma	Homo sapiens
559 ng/mL	15 mg 1 times / day multiple, oral	DEXLANSOPRAZOLE plasma	Homo sapiens
33.5 ng/mL/(mg dose)	30 mg 1 times / day multiple, oral	DEXLANSOPRAZOLE plasma	Homo sapiens
1005 ng/mL	30 mg 1 times / day multiple, oral	DEXLANSOPRAZOLE plasma	Homo sapiens
16.1 ng/mL/(mg dose)	60 mg 1 times / day multiple, oral	DEXLANSOPRAZOLE plasma	Homo sapiens
964 ng/mL	60 mg 1 times / day multiple, oral	DEXLANSOPRAZOLE plasma	Homo sapiens
658 ng/mL	30 mg 1 times / day multiple, oral	DEXLANSOPRAZOLE plasma	Homo sapiens
1397 ng/mL	60 mg 1 times / day multiple, oral	DEXLANSOPRAZOLE plasma	Homo sapiens
0.36 μg/mL	30 mg single, oral	LEVOLANSOPRAZOLE serum	Homo sapiens
337 ng/mL	60 mg single, oral	LEVOLANSOPRAZOLE plasma	Homo sapiens
528 ng/mL	60 mg single, oral	LEVOLANSOPRAZOLE plasma	Homo sapiens
1156 ng/mL	60 mg single, oral	LEVOLANSOPRAZOLE plasma	Homo sapiens
167 ng/mL	30 mg 1 times / day multiple, oral	LEVOLANSOPRAZOLE plasma	Homo sapiens
848.13 ng/mL	30 mg 2 times / day multiple, intravenous	LEVOLANSOPRAZOLE plasma	Homo sapiens
811.63 ng/mL	30 mg 2 times / day multiple, intravenous	LEVOLANSOPRAZOLE plasma	Homo sapiens

AUC

Value	Dose	Analyte	Population
3192 ng × h/mL	30 mg single, intravenous	LANSOPRAZOLE plasma	Homo sapiens
128 μg × h/L/(mg dose)	15 mg 1 times / day multiple, oral	DEXLANSOPRAZOLE plasma	Homo sapiens
143.2 μg × h/L/(mg dose)	15 mg 1 times / day multiple, oral	DEXLANSOPRAZOLE plasma	Homo sapiens
1914 ng × h/mL	15 mg 1 times / day multiple, oral	DEXLANSOPRAZOLE plasma	Homo sapiens
2149 ng × h/mL	15 mg 1 times / day multiple, oral	DEXLANSOPRAZOLE plasma	Homo sapiens
96 μg × h/L/(mg dose)	30 mg 1 times / day multiple, oral	DEXLANSOPRAZOLE plasma	Homo sapiens
87.6 μg × h/L/(mg dose)	30 mg 1 times / day multiple, oral	DEXLANSOPRAZOLE plasma	Homo sapiens
2892 ng*h/mL	30 mg 1 times / day multiple, oral	DEXLANSOPRAZOLE plasma	Homo sapiens
2628 ng*h/mL	30 mg 1 times / day multiple, oral	DEXLANSOPRAZOLE plasma	Homo sapiens
62 μg × h/L/(mg dose)	60 mg 1 times / day multiple, oral	DEXLANSOPRAZOLE plasma	Homo sapiens
55.5 μg × h/L/(mg dose)	60 mg 1 times / day multiple, oral	DEXLANSOPRAZOLE plasma	Homo sapiens
3747 ng × h/mL	60 mg 1 times / day multiple, oral	DEXLANSOPRAZOLE plasma	Homo sapiens
3330 ng × h/mL	60 mg 1 times / day multiple, oral	DEXLANSOPRAZOLE plasma	Homo sapiens
3275 ng × h/mL	30 mg 1 times / day multiple, oral	DEXLANSOPRAZOLE plasma	Homo sapiens
6529 ng × h/mL	60 mg 1 times / day multiple, oral	DEXLANSOPRAZOLE plasma	Homo sapiens
1.56 μg × h/mL	30 mg single, oral	LEVOLANSOPRAZOLE serum	Homo sapiens
524 ng × h/mL	60 mg single, oral	LEVOLANSOPRAZOLE plasma	Homo sapiens
967 ng × h/mL	60 mg single, oral	LEVOLANSOPRAZOLE plasma	Homo sapiens
3892 ng × h/mL	60 mg single, oral	LEVOLANSOPRAZOLE plasma	Homo sapiens
451 ng × h/mL	30 mg 1 times / day multiple, oral	LEVOLANSOPRAZOLE plasma	Homo sapiens
1161.07 ng × h/mL	30 mg 2 times / day multiple, intravenous	LEVOLANSOPRAZOLE plasma	Homo sapiens
1180.29 ng × h/mL	30 mg 2 times / day multiple, intravenous	LEVOLANSOPRAZOLE plasma	Homo sapiens

T_1/2

Value	Dose	Analyte	Population
1.3 h	30 mg single, intravenous	LANSOPRAZOLE plasma	Homo sapiens
1.66 h	30 mg 1 times / day multiple, oral	DEXLANSOPRAZOLE plasma	Homo sapiens
2.59 h	60 mg 1 times / day multiple, oral	DEXLANSOPRAZOLE plasma	Homo sapiens
0.6 h	60 mg single, oral	LEVOLANSOPRAZOLE plasma	Homo sapiens
0.7 h	60 mg single, oral	LEVOLANSOPRAZOLE plasma	Homo sapiens
1.6 h	60 mg single, oral	LEVOLANSOPRAZOLE plasma	Homo sapiens
1.2 h	30 mg 1 times / day multiple, oral	LEVOLANSOPRAZOLE plasma	Homo sapiens
1.02 h	30 mg 2 times / day multiple, intravenous	LEVOLANSOPRAZOLE plasma	Homo sapiens
0.87 h	30 mg 2 times / day multiple, intravenous	LEVOLANSOPRAZOLE plasma	Homo sapiens

F_unbound

Value	Dose	Co-administered	Analyte	Population
5.8%	30 mg single, oral		LEVOLANSOPRAZOLE serum	Homo sapiens

Doses

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Dose	Population	Adverse events
30 mg 2 times / day multiple, intravenous	healthy, 18-29 years
90 mg single, intravenous	healthy, 18-29 years
300 mg single, oral Highest studied dose	healthy, 35 years (range: 18 - 50 years)
60 mg 1 times / day steady, oral Recommended	unhealthy, 48 years (range: 18-90 years)	Disc. AE: Diarrhea...
60 mg 1 times / day steady, oral Recommended	unhealthy, 48 years (range: 18-90 years)	Disc. AE: Abdominal pain...

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AEs

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AE	Significance	Dose	Population
Diarrhea	0.7% Disc. AE	60 mg 1 times / day steady, oral Recommended	unhealthy, 48 years (range: 18-90 years)
Abdominal pain	0.5% Disc. AE	60 mg 1 times / day steady, oral Recommended	unhealthy, 48 years (range: 18-90 years)
Diarrhea	0.2% Disc. AE	30 mg 1 times / day steady, oral	unhealthy, 48 years (range: 18-90 years)
Abdominal pain	0.6% Disc. AE	90 mg 1 times / day steady, oral	unhealthy, 48 years (range: 18-90 years)
Diarrhea	0.7% Disc. AE	90 mg 1 times / day steady, oral	unhealthy, 48 years (range: 18-90 years)

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Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1,737 inhibitor 1,587	inhibitor 1,767	inhibitor 1,852

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A1 110 CYP1A2 1,524 CYP2A6 707 CYP2B6 810 CYP2C8 911 CYP2E1 882 CYP2C19 1,478	CYP2C19 991

Drug as perpetrator

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Target	Modality	Activity
CYP1A1 218	inhibitor 3,277	unlikely
CYP2A6 739	inhibitor 3,277	unlikely
CYP2B6 1,001	inhibitor 3,277	unlikely
CYP2C8 965	inhibitor 3,277	unlikely
CYP2D6 1,891	inhibitor 3,277	unlikely

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Drug as victim

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Target	Modality	Activity	Metabolite	Clinical evidence
CYP3A4 1,737	substrate 3,367	yes
CYP2C19 991	substrate 3,367	yes		yes (pharmacogenomic study)

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Sourcing

Sourcing

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Vendor/Aggregator	ID	URL
ChEBI	CHEBI:6375	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:6375
ChemicalBook	CB6396972	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB6396972
eMolecules	902018	https://www.emolecules.com/cgi-bin/more?vid=902018
MolPort	MolPort-003-666-508	https://www.molport.com/shop/molecule-link/MolPort-003-666-508
Selleck Chemicals	Lansoprazole	http://www.selleckchem.com/products/Lansoprazole.html

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PubMed

Show entries

Title	Date	PubMed
Prostacyclin analog prevents stress-induced expression of immediate early genes and gastric mucosal lesions in the rat stomach.	1999	10353594
Rational prescribing: practice audit and drug switch in dyspepsia management.	1999 Dec	10692753
Double-blind comparison of lansoprazole 15 mg, lansoprazole 30 mg and placebo as maintenance therapy in patients with healed duodenal ulcers resistant to H2-receptor antagonists.	1999 Jul	10383532
Ultrasonographic evaluation of lansoprazole-induced improvement of submucosal injury in patients with gastroesophageal reflux.	2000 Feb	10685739
Advantage of expressing the variations in some digestive parameters as a function of gastric emptying instead of time.	2001	11549836

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Patents

Sample Use Guides

In Vivo Use Guide

Duodenal Ulcers: 15 mg Once daily for 4 weeks Gastroesophageal Reflux: 30 mg Once daily for up to 8 weeks

Route of Administration: Oral

In Vitro Use Guide

Lansoprazole is a gastric parietal cell proton pump inhibitor that is also active against Helicobacter pylori in vitro. The antimicrobial activity of lansoprazole and of its sulfenamide, a rearrangement product occurring spontaneously in acid environments, was studied by determining the MICs and MBCs for 11 cytotoxic and eight non-cytotoxic H. pylori strains and by measuring the rapidity of bacterial killing. The MIC90 and MBC90 were 2.5 mg/L and 10 mg/L, respectively, both for lansoprazole and for its sulfenamide.