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

Description
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/22950496

Lansoprazole is a proton pump inhibitor, which prevents the stomach from producing acid. Lansoprazole has been marketed for many years and is one of several proton-pump inhibitors (PPI's). It was used for the treatment of acid-reflux disorders (GERD), peptic ulcer disease, H. pylori eradication, and prevention of gastrointestinal bleeds with NSAID use. Lansoprazole belongs to a class of ant secretory compounds, the substituted benzimidazoles, that do not exhibit anticholinergic or histamine H2-receptor antagonist properties, but that suppress gastric acid secretion by specific inhibition of the (H+, K+ )-ATPase enzyme system at the secretory surface of the gastric parietal cell. Because this enzyme system is regarded as the acid (proton) pump within the parietal cell, lansoprazole has been characterized as a gastric acid-pump inhibitor, in that it blocks the final step of acid production. This effect is dose-related and leads to inhibition of both basal and stimulated gastric acid secretion irrespective of the stimulus. Lansoprazole is extensively metabolized in the liver. Two metabolites have been identified in measurable quantities in plasma (the hydroxylated sulfinyl and sulfone derivatives of lansoprazole). These metabolites have very little or no antisecretory activity. Lansoprazole is thought to be transformed into two active species which inhibit acid secretion by (H+, K+ )-ATPase within the parietal cell canaliculus, but are not present in the systemic circulation. The plasma elimination half-life of lansoprazole does not reflect its duration of suppression of gastric acid secretion. Thus, the plasma elimination half-life is less than two hours, while the acid inhibitory effect lasts more than 24 hours.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
PREVACID

Approved Use

Use •treats frequent heartburn (occurs 2 or more days a week) •not intended for immediate relief of heartburn; this drug may take 1 to 4 days for full effect

Launch Date

1.0306656E12
Primary
PREVACID

Approved Use

Use •treats frequent heartburn (occurs 2 or more days a week) •not intended for immediate relief of heartburn; this drug may take 1 to 4 days for full effect

Launch Date

1.0306656E12
Primary
PREVACID

Approved Use

Use •treats frequent heartburn (occurs 2 or more days a week) •not intended for immediate relief of heartburn; this drug may take 1 to 4 days for full effect

Launch Date

1.0306656E12
Primary
DEXILANT

Approved Use

DEXILANT is a proton pump inhibitor (PPI) indicated for: •Healing of all grades of erosive esophagitis (EE). (1.1) •Maintaining healing of EE and relief of heartburn. (1.2) •Treating heartburn associated with symptomatic non-erosive gastroesophageal reflux disease (GERD). (1.3) 1.1 Healing of Erosive Esophagitis DEXILANT is indicated for healing of all grades of erosive esophagitis (EE) for up to eight weeks. 1.2 Maintenance of Healed Erosive Esophagitis DEXILANT is indicated to maintain healing of EE and relief of heartburn for up to six months. 1.3 Symptomatic Non-Erosive Gastroesophageal Reflux Disease DEXILANT is indicated for the treatment of heartburn associated with symptomatic non-erosive gastroesophageal reflux disease (GERD) for four weeks.

Launch Date

1.23327362E12
Curative
DEXILANT

Approved Use

DEXILANT is a proton pump inhibitor (PPI) indicated for: •Healing of all grades of erosive esophagitis (EE). (1.1) •Maintaining healing of EE and relief of heartburn. (1.2) •Treating heartburn associated with symptomatic non-erosive gastroesophageal reflux disease (GERD). (1.3) 1.1 Healing of Erosive Esophagitis DEXILANT is indicated for healing of all grades of erosive esophagitis (EE) for up to eight weeks. 1.2 Maintenance of Healed Erosive Esophagitis DEXILANT is indicated to maintain healing of EE and relief of heartburn for up to six months. 1.3 Symptomatic Non-Erosive Gastroesophageal Reflux Disease DEXILANT is indicated for the treatment of heartburn associated with symptomatic non-erosive gastroesophageal reflux disease (GERD) for four weeks.

Launch Date

1.23327362E12
Primary
PREVACID

Approved Use

INDICATIONS AND USAGE. Short-Term Treatment of Active Duodenal Ulcer PREVACID is indicated for short-term treatment (up to 4 weeks) for healing and symptom relief of active duodenal ulcer. H. pylori Eradication to Reduce the Risk of Duodenal Ulcer Recurrence. Triple Therapy: PREVACID/amoxicillin/clarithromycin. PREVACID in combination with amoxicillin plus clarithromycin as triple therapy, is indicated for the treatment of patients with H. pylori infection and duodenal ulcer disease (active or one-year history of a duodenal ulcer) to eradicate H. pylori. Eradication of H. pylori has been shown to reduce the risk of duodenal ulcer recurrence. Dual Therapy: PREVACID/amoxicillin. PREVACID in combination with amoxicillin as dual therapy, is indicated for the treatment of patients with H. pylori infection and duodenal ulcer disease (active or one-year history of a duodenal ulcer) who are either allergic or intolerant to clarithromycin or in whom resistance to clarithromycin is known or suspected. Eradication of H. pylori has been shown to reduce the risk of duodenal ulcer recurrence. Maintenance of Healed Duodenal Ulcers PREVACID is indicated to maintain healing of duodenal ulcers. Controlled studies do not extend beyond 12 months. Short-Term Treatment of Active Benign Gastric Ulcer PREVACID is indicated for short-term treatment (up to 8 weeks) for healing and symptom relief of active benign gastric ulcer Healing of NSAID-Associated Gastric Ulcer PREVACID IS INDICATED FOR THE TREATMENT OF NSAID-ASSOCIATED GASTRIC ULCER IN PATIENTS WHO CONTINUE NSAID USE. CONTROLLED STUDIES DID NOT EXTEND BEYOND 8 WEEKS. Risk Reduction of NSAID-Associated Gastric Ulcer PREVACID is indicated for reducing the risk of NSAID-associated gastric ulcers in patients with a history of a documented gastric ulcer who require the use of an NSAID. Controlled studies did not extend beyond 12 weeks. Gastroesophageal Reflux Disease (GERD) Short-Term Treatment of Symptomatic GERD PREVACID is indicated for the treatment of heartburn and other symptoms associated with GERD. Short-Term Treatment of Erosive Esophagitis PREVACID is indicated for short-term treatment (up to 8 weeks) for healing and symptom relief of all grades of erosive esophagitis. For patients who do not heal with PREVACID for 8 weeks (5-10%), it may be helpful to give an additional 8 weeks of treatment. If there is a recurrence of erosive esophagitis an additional 8-week course of PREVACID may be considered. Maintenance of Healing of Erosive Esophagitis PREVACID is indicated to maintain healing of erosive esophagitis. Controlled studies did not extend beyond 12 months. Pathological Hypersecretory Conditions Including Zollinger-Ellison Syndrome PREVACID is indicated for the long-term treatment of pathological hypersecretory conditions, including Zollinger-Ellison syndrome.

Launch Date

1.03057922E12
Primary
PREVACID

Approved Use

INDICATIONS AND USAGE. Short-Term Treatment of Active Duodenal Ulcer PREVACID is indicated for short-term treatment (up to 4 weeks) for healing and symptom relief of active duodenal ulcer. H. pylori Eradication to Reduce the Risk of Duodenal Ulcer Recurrence. Triple Therapy: PREVACID/amoxicillin/clarithromycin. PREVACID in combination with amoxicillin plus clarithromycin as triple therapy, is indicated for the treatment of patients with H. pylori infection and duodenal ulcer disease (active or one-year history of a duodenal ulcer) to eradicate H. pylori. Eradication of H. pylori has been shown to reduce the risk of duodenal ulcer recurrence. Dual Therapy: PREVACID/amoxicillin. PREVACID in combination with amoxicillin as dual therapy, is indicated for the treatment of patients with H. pylori infection and duodenal ulcer disease (active or one-year history of a duodenal ulcer) who are either allergic or intolerant to clarithromycin or in whom resistance to clarithromycin is known or suspected. Eradication of H. pylori has been shown to reduce the risk of duodenal ulcer recurrence. Maintenance of Healed Duodenal Ulcers PREVACID is indicated to maintain healing of duodenal ulcers. Controlled studies do not extend beyond 12 months. Short-Term Treatment of Active Benign Gastric Ulcer PREVACID is indicated for short-term treatment (up to 8 weeks) for healing and symptom relief of active benign gastric ulcer Healing of NSAID-Associated Gastric Ulcer PREVACID IS INDICATED FOR THE TREATMENT OF NSAID-ASSOCIATED GASTRIC ULCER IN PATIENTS WHO CONTINUE NSAID USE. CONTROLLED STUDIES DID NOT EXTEND BEYOND 8 WEEKS. Risk Reduction of NSAID-Associated Gastric Ulcer PREVACID is indicated for reducing the risk of NSAID-associated gastric ulcers in patients with a history of a documented gastric ulcer who require the use of an NSAID. Controlled studies did not extend beyond 12 weeks. Gastroesophageal Reflux Disease (GERD) Short-Term Treatment of Symptomatic GERD PREVACID is indicated for the treatment of heartburn and other symptoms associated with GERD. Short-Term Treatment of Erosive Esophagitis PREVACID is indicated for short-term treatment (up to 8 weeks) for healing and symptom relief of all grades of erosive esophagitis. For patients who do not heal with PREVACID for 8 weeks (5-10%), it may be helpful to give an additional 8 weeks of treatment. If there is a recurrence of erosive esophagitis an additional 8-week course of PREVACID may be considered. Maintenance of Healing of Erosive Esophagitis PREVACID is indicated to maintain healing of erosive esophagitis. Controlled studies did not extend beyond 12 months. Pathological Hypersecretory Conditions Including Zollinger-Ellison Syndrome PREVACID is indicated for the long-term treatment of pathological hypersecretory conditions, including Zollinger-Ellison syndrome.

Launch Date

1.03057922E12
Primary
PREVACID

Approved Use

INDICATIONS AND USAGE. Short-Term Treatment of Active Duodenal Ulcer PREVACID is indicated for short-term treatment (up to 4 weeks) for healing and symptom relief of active duodenal ulcer. H. pylori Eradication to Reduce the Risk of Duodenal Ulcer Recurrence. Triple Therapy: PREVACID/amoxicillin/clarithromycin. PREVACID in combination with amoxicillin plus clarithromycin as triple therapy, is indicated for the treatment of patients with H. pylori infection and duodenal ulcer disease (active or one-year history of a duodenal ulcer) to eradicate H. pylori. Eradication of H. pylori has been shown to reduce the risk of duodenal ulcer recurrence. Dual Therapy: PREVACID/amoxicillin. PREVACID in combination with amoxicillin as dual therapy, is indicated for the treatment of patients with H. pylori infection and duodenal ulcer disease (active or one-year history of a duodenal ulcer) who are either allergic or intolerant to clarithromycin or in whom resistance to clarithromycin is known or suspected. Eradication of H. pylori has been shown to reduce the risk of duodenal ulcer recurrence. Maintenance of Healed Duodenal Ulcers PREVACID is indicated to maintain healing of duodenal ulcers. Controlled studies do not extend beyond 12 months. Short-Term Treatment of Active Benign Gastric Ulcer PREVACID is indicated for short-term treatment (up to 8 weeks) for healing and symptom relief of active benign gastric ulcer Healing of NSAID-Associated Gastric Ulcer PREVACID IS INDICATED FOR THE TREATMENT OF NSAID-ASSOCIATED GASTRIC ULCER IN PATIENTS WHO CONTINUE NSAID USE. CONTROLLED STUDIES DID NOT EXTEND BEYOND 8 WEEKS. Risk Reduction of NSAID-Associated Gastric Ulcer PREVACID is indicated for reducing the risk of NSAID-associated gastric ulcers in patients with a history of a documented gastric ulcer who require the use of an NSAID. Controlled studies did not extend beyond 12 weeks. Gastroesophageal Reflux Disease (GERD) Short-Term Treatment of Symptomatic GERD PREVACID is indicated for the treatment of heartburn and other symptoms associated with GERD. Short-Term Treatment of Erosive Esophagitis PREVACID is indicated for short-term treatment (up to 8 weeks) for healing and symptom relief of all grades of erosive esophagitis. For patients who do not heal with PREVACID for 8 weeks (5-10%), it may be helpful to give an additional 8 weeks of treatment. If there is a recurrence of erosive esophagitis an additional 8-week course of PREVACID may be considered. Maintenance of Healing of Erosive Esophagitis PREVACID is indicated to maintain healing of erosive esophagitis. Controlled studies did not extend beyond 12 months. Pathological Hypersecretory Conditions Including Zollinger-Ellison Syndrome PREVACID is indicated for the long-term treatment of pathological hypersecretory conditions, including Zollinger-Ellison syndrome.

Launch Date

1.03057922E12
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
1705 ng/mL
30 mg single, intravenous
dose: 30 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
LANSOPRAZOLE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
1136 ng/mL
60 mg 1 times / day multiple, oral
dose: 60 mg
route of administration: oral
experiment type: multiple
co-administered:
DEXLANSOPRAZOLE plasma
Homo sapiens
population: unhealthy
age: Adolescents
sex:
food status:
691 ng/mL
30 mg 1 times / day multiple, oral
dose: 30 mg
route of administration: oral
experiment type: multiple
co-administered:
DEXLANSOPRAZOLE plasma
Homo sapiens
population: unhealthy
age: Adolescents
sex:
food status:
16.1 (ng/mL)/mg
60 mg 1 times / day multiple, oral
dose: 60 mg
route of administration: oral
experiment type: multiple
co-administered:
DEXLANSOPRAZOLE plasma
Homo sapiens
population: unhealthy
age: Children
sex:
food status:
33.5 (ng/mL)/mg
30 mg 1 times / day multiple, oral
dose: 30 mg
route of administration: oral
experiment type: multiple
co-administered:
DEXLANSOPRAZOLE plasma
Homo sapiens
population: unhealthy
age: Children
sex:
food status:
37.3 (ng/mL)/mg
15 mg 1 times / day multiple, oral
dose: 15 mg
route of administration: oral
experiment type: multiple
co-administered:
DEXLANSOPRAZOLE plasma
Homo sapiens
population: unhealthy
age: Children
sex:
food status:
1005 ng/mL
30 mg 1 times / day multiple, oral
dose: 30 mg
route of administration: oral
experiment type: multiple
co-administered:
DEXLANSOPRAZOLE plasma
Homo sapiens
population: unhealthy
age: Children
sex:
food status:
559 ng/mL
15 mg 1 times / day multiple, oral
dose: 15 mg
route of administration: oral
experiment type: multiple
co-administered:
DEXLANSOPRAZOLE plasma
Homo sapiens
population: unhealthy
age: Children
sex:
food status:
964 ng/mL
60 mg 1 times / day multiple, oral
dose: 60 mg
route of administration: oral
experiment type: multiple
co-administered:
DEXLANSOPRAZOLE plasma
Homo sapiens
population: unhealthy
age: Children
sex:
food status:
658 ng/mL
30 mg 1 times / day multiple, oral
dose: 30 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
DEXLANSOPRAZOLE plasma
Homo sapiens
population: HEALTHY
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
1397 ng/mL
60 mg 1 times / day multiple, oral
dose: 60 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
DEXLANSOPRAZOLE plasma
Homo sapiens
population: HEALTHY
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
3192 ng × h/mL
30 mg single, intravenous
dose: 30 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
LANSOPRAZOLE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
143.2 (ng*h/mL)/mg
15 mg 1 times / day multiple, oral
dose: 15 mg
route of administration: oral
experiment type: multiple
co-administered:
DEXLANSOPRAZOLE plasma
Homo sapiens
population: unhealthy
age: Children
sex:
food status:
55.5 (ng*h/mL)/mg
60 mg 1 times / day multiple, oral
dose: 60 mg
route of administration: oral
experiment type: multiple
co-administered:
DEXLANSOPRAZOLE plasma
Homo sapiens
population: unhealthy
age: Children
sex:
food status:
87.6 (ng*h/mL)/mg
30 mg 1 times / day multiple, oral
dose: 30 mg
route of administration: oral
experiment type: multiple
co-administered:
DEXLANSOPRAZOLE plasma
Homo sapiens
population: unhealthy
age: Children
sex:
food status:
2149 ng*h/mL
15 mg 1 times / day multiple, oral
dose: 15 mg
route of administration: oral
experiment type: multiple
co-administered:
DEXLANSOPRAZOLE plasma
Homo sapiens
population: unhealthy
age: Children
sex:
food status:
2628 ng*h/mL
30 mg 1 times / day multiple, oral
dose: 30 mg
route of administration: oral
experiment type: multiple
co-administered:
DEXLANSOPRAZOLE plasma
Homo sapiens
population: unhealthy
age: Children
sex:
food status:
3330 ng*h/mL
60 mg 1 times / day multiple, oral
dose: 60 mg
route of administration: oral
experiment type: multiple
co-administered:
DEXLANSOPRAZOLE plasma
Homo sapiens
population: unhealthy
age: Children
sex:
food status:
128 (ng*h/mL)/mg
15 mg 1 times / day multiple, oral
dose: 15 mg
route of administration: oral
experiment type: multiple
co-administered:
DEXLANSOPRAZOLE plasma
Homo sapiens
population: unhealthy
age: Children
sex:
food status:
62 (ng*h/mL)/mg
60 mg 1 times / day multiple, oral
dose: 60 mg
route of administration: oral
experiment type: multiple
co-administered:
DEXLANSOPRAZOLE plasma
Homo sapiens
population: unhealthy
age: Children
sex:
food status:
96 (ng*h/mL)/mg
30 mg 1 times / day multiple, oral
dose: 30 mg
route of administration: oral
experiment type: multiple
co-administered:
DEXLANSOPRAZOLE plasma
Homo sapiens
population: unhealthy
age: Children
sex:
food status:
1914 ng*h/mL
15 mg 1 times / day multiple, oral
dose: 15 mg
route of administration: oral
experiment type: multiple
co-administered:
DEXLANSOPRAZOLE plasma
Homo sapiens
population: unhealthy
age: Children
sex:
food status:
2892 ng*h/mL
30 mg 1 times / day multiple, oral
dose: 30 mg
route of administration: oral
experiment type: multiple
co-administered:
DEXLANSOPRAZOLE plasma
Homo sapiens
population: unhealthy
age: Children
sex:
food status:
3747 ng*h/mL
60 mg 1 times / day multiple, oral
dose: 60 mg
route of administration: oral
experiment type: multiple
co-administered:
DEXLANSOPRAZOLE plasma
Homo sapiens
population: unhealthy
age: Children
sex:
food status:
3275 ng × h/mL
30 mg 1 times / day multiple, oral
dose: 30 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
DEXLANSOPRAZOLE plasma
Homo sapiens
population: HEALTHY
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
6529 ng × h/mL
60 mg 1 times / day multiple, oral
dose: 60 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
DEXLANSOPRAZOLE plasma
Homo sapiens
population: HEALTHY
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
1.3 h
30 mg single, intravenous
dose: 30 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
LANSOPRAZOLE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
2.59 h
60 mg 1 times / day multiple, oral
dose: 60 mg
route of administration: oral
experiment type: multiple
co-administered:
DEXLANSOPRAZOLE plasma
Homo sapiens
population: unhealthy
age: Adolescents
sex:
food status:
1.66 h
30 mg 1 times / day multiple, oral
dose: 30 mg
route of administration: oral
experiment type: multiple
co-administered:
DEXLANSOPRAZOLE plasma
Homo sapiens
population: unhealthy
age: Adolescents
sex:
food status:
Doses

Doses

DosePopulationAdverse events​
30 mg 2 times / day multiple, intravenous
Dose: 30 mg, 2 times / day
Route: intravenous
Route: multiple
Dose: 30 mg, 2 times / day
Sources:
healthy, 18-29 years
n = 18
Health Status: healthy
Age Group: 18-29 years
Sex: M+F
Population Size: 18
Sources:
90 mg single, intravenous
Dose: 90 mg
Route: intravenous
Route: single
Dose: 90 mg
Sources:
healthy, 18-29 years
n = 8
Health Status: healthy
Age Group: 18-29 years
Sex: M+F
Population Size: 8
Sources:
300 mg single, oral
Highest studied dose
Dose: 300 mg
Route: oral
Route: single
Dose: 300 mg
Sources:
healthy, 35 years (range: 18 - 50 years)
n = 36
Health Status: healthy
Age Group: 35 years (range: 18 - 50 years)
Sex: M+F
Population Size: 36
Sources:
60 mg 1 times / day steady, oral
Recommended
unhealthy, 48 years (range: 18-90 years)
n = 2218
Health Status: unhealthy
Age Group: 48 years (range: 18-90 years)
Sex: M+F
Population Size: 2218
Sources:
Disc. AE: Diarrhea...
60 mg 1 times / day steady, oral
Recommended
Dose: 60 mg, 1 times / day
Route: oral
Route: steady
Dose: 60 mg, 1 times / day
Sources: Page: p. 35
unhealthy, 48 years (range: 18-90 years)
n = 2218
Health Status: unhealthy
Age Group: 48 years (range: 18-90 years)
Sex: M+F
Population Size: 2218
Sources: Page: p. 35
Disc. AE: Abdominal pain...
AEs leading to
discontinuation/dose reduction:
Abdominal pain (0.5%)
Sources: Page: p. 35
30 mg 1 times / day steady, oral
Dose: 30 mg, 1 times / day
Route: oral
Route: steady
Dose: 30 mg, 1 times / day
Sources: Page: p. 35
unhealthy, 48 years (range: 18-90 years)
n = 455
Health Status: unhealthy
Age Group: 48 years (range: 18-90 years)
Sex: M+F
Population Size: 455
Sources: Page: p. 35
Disc. AE: Diarrhea...
AEs leading to
discontinuation/dose reduction:
Diarrhea (0.2%)
Sources: Page: p. 35
90 mg 1 times / day steady, oral
Dose: 90 mg, 1 times / day
Route: oral
Route: steady
Dose: 90 mg, 1 times / day
Sources: Page: p. 35
unhealthy, 48 years (range: 18-90 years)
n = 1754
Health Status: unhealthy
Age Group: 48 years (range: 18-90 years)
Sex: M+F
Population Size: 1754
Sources: Page: p. 35
Disc. AE: Diarrhea, Abdominal pain...
AEs leading to
discontinuation/dose reduction:
Diarrhea (0.7%)
Abdominal pain (0.6%)
Sources: Page: p. 35
60 mg 1 times / day steady, oral
Recommended
Dose: 60 mg, 1 times / day
Route: oral
Route: steady
Dose: 60 mg, 1 times / day
Sources: Page: p. 36
unhealthy, adult
n = 2311
Health Status: unhealthy
Age Group: adult
Population Size: 2311
Sources: Page: p. 36
Disc. AE: Dyspepsia, Eructation...
AEs leading to
discontinuation/dose reduction:
Dyspepsia (3 patients)
Eructation (2 patients)
Nausea (6 patients)
Vomiting (6 patients)
Erosive esophagitis (1 patient)
Sources: Page: p. 36
90 mg 1 times / day steady, oral
Dose: 90 mg, 1 times / day
Route: oral
Route: steady
Dose: 90 mg, 1 times / day
Sources: Page: p. 36
unhealthy, adult
n = 2142
Health Status: unhealthy
Age Group: adult
Population Size: 2142
Sources: Page: p. 36
Disc. AE: Dyspepsia, Eructation...
AEs leading to
discontinuation/dose reduction:
Dyspepsia (1 patient)
Eructation (1 patient)
Nausea (9 patients)
Vomiting (6 patients)
Sources: Page: p. 36
60 mg 2 times / day steady, oral
Overdose
Dose: 60 mg, 2 times / day
Route: oral
Route: steady
Dose: 60 mg, 2 times / day
Sources:
unhealthy
Other AEs: Hypertension...
AEs

AEs

AESignificanceDosePopulation
Diarrhea 0.7%
Disc. AE
60 mg 1 times / day steady, oral
Recommended
unhealthy, 48 years (range: 18-90 years)
n = 2218
Health Status: unhealthy
Age Group: 48 years (range: 18-90 years)
Sex: M+F
Population Size: 2218
Sources:
Abdominal pain 0.5%
Disc. AE
60 mg 1 times / day steady, oral
Recommended
Dose: 60 mg, 1 times / day
Route: oral
Route: steady
Dose: 60 mg, 1 times / day
Sources: Page: p. 35
unhealthy, 48 years (range: 18-90 years)
n = 2218
Health Status: unhealthy
Age Group: 48 years (range: 18-90 years)
Sex: M+F
Population Size: 2218
Sources: Page: p. 35
Diarrhea 0.2%
Disc. AE
30 mg 1 times / day steady, oral
Dose: 30 mg, 1 times / day
Route: oral
Route: steady
Dose: 30 mg, 1 times / day
Sources: Page: p. 35
unhealthy, 48 years (range: 18-90 years)
n = 455
Health Status: unhealthy
Age Group: 48 years (range: 18-90 years)
Sex: M+F
Population Size: 455
Sources: Page: p. 35
Abdominal pain 0.6%
Disc. AE
90 mg 1 times / day steady, oral
Dose: 90 mg, 1 times / day
Route: oral
Route: steady
Dose: 90 mg, 1 times / day
Sources: Page: p. 35
unhealthy, 48 years (range: 18-90 years)
n = 1754
Health Status: unhealthy
Age Group: 48 years (range: 18-90 years)
Sex: M+F
Population Size: 1754
Sources: Page: p. 35
Diarrhea 0.7%
Disc. AE
90 mg 1 times / day steady, oral
Dose: 90 mg, 1 times / day
Route: oral
Route: steady
Dose: 90 mg, 1 times / day
Sources: Page: p. 35
unhealthy, 48 years (range: 18-90 years)
n = 1754
Health Status: unhealthy
Age Group: 48 years (range: 18-90 years)
Sex: M+F
Population Size: 1754
Sources: Page: p. 35
Erosive esophagitis 1 patient
Disc. AE
60 mg 1 times / day steady, oral
Recommended
Dose: 60 mg, 1 times / day
Route: oral
Route: steady
Dose: 60 mg, 1 times / day
Sources: Page: p. 36
unhealthy, adult
n = 2311
Health Status: unhealthy
Age Group: adult
Population Size: 2311
Sources: Page: p. 36
Eructation 2 patients
Disc. AE
60 mg 1 times / day steady, oral
Recommended
Dose: 60 mg, 1 times / day
Route: oral
Route: steady
Dose: 60 mg, 1 times / day
Sources: Page: p. 36
unhealthy, adult
n = 2311
Health Status: unhealthy
Age Group: adult
Population Size: 2311
Sources: Page: p. 36
Dyspepsia 3 patients
Disc. AE
60 mg 1 times / day steady, oral
Recommended
Dose: 60 mg, 1 times / day
Route: oral
Route: steady
Dose: 60 mg, 1 times / day
Sources: Page: p. 36
unhealthy, adult
n = 2311
Health Status: unhealthy
Age Group: adult
Population Size: 2311
Sources: Page: p. 36
Nausea 6 patients
Disc. AE
60 mg 1 times / day steady, oral
Recommended
Dose: 60 mg, 1 times / day
Route: oral
Route: steady
Dose: 60 mg, 1 times / day
Sources: Page: p. 36
unhealthy, adult
n = 2311
Health Status: unhealthy
Age Group: adult
Population Size: 2311
Sources: Page: p. 36
Vomiting 6 patients
Disc. AE
60 mg 1 times / day steady, oral
Recommended
Dose: 60 mg, 1 times / day
Route: oral
Route: steady
Dose: 60 mg, 1 times / day
Sources: Page: p. 36
unhealthy, adult
n = 2311
Health Status: unhealthy
Age Group: adult
Population Size: 2311
Sources: Page: p. 36
Dyspepsia 1 patient
Disc. AE
90 mg 1 times / day steady, oral
Dose: 90 mg, 1 times / day
Route: oral
Route: steady
Dose: 90 mg, 1 times / day
Sources: Page: p. 36
unhealthy, adult
n = 2142
Health Status: unhealthy
Age Group: adult
Population Size: 2142
Sources: Page: p. 36
Eructation 1 patient
Disc. AE
90 mg 1 times / day steady, oral
Dose: 90 mg, 1 times / day
Route: oral
Route: steady
Dose: 90 mg, 1 times / day
Sources: Page: p. 36
unhealthy, adult
n = 2142
Health Status: unhealthy
Age Group: adult
Population Size: 2142
Sources: Page: p. 36
Vomiting 6 patients
Disc. AE
90 mg 1 times / day steady, oral
Dose: 90 mg, 1 times / day
Route: oral
Route: steady
Dose: 90 mg, 1 times / day
Sources: Page: p. 36
unhealthy, adult
n = 2142
Health Status: unhealthy
Age Group: adult
Population Size: 2142
Sources: Page: p. 36
Nausea 9 patients
Disc. AE
90 mg 1 times / day steady, oral
Dose: 90 mg, 1 times / day
Route: oral
Route: steady
Dose: 90 mg, 1 times / day
Sources: Page: p. 36
unhealthy, adult
n = 2142
Health Status: unhealthy
Age Group: adult
Population Size: 2142
Sources: Page: p. 36
Hypertension serious
60 mg 2 times / day steady, oral
Overdose
Dose: 60 mg, 2 times / day
Route: oral
Route: steady
Dose: 60 mg, 2 times / day
Sources:
unhealthy
Overview

Overview

OverviewOther

Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
unlikely
unlikely
unlikely
unlikely
unlikely
unlikely
unlikely
unlikely
no (co-administration study)
Comment: in vivo studies showed that DEXILANT did not have an impact on the pharmacokinetics of coadministered theophylline (CYP1A2 substrate)
Page: 11.0
unlikely
no (co-administration study)
Comment: in vivo studies showed that DEXILANT did not have an impact on the pharmacokinetics of coadministered phenytoin (CYP2C9 substrate)
Page: 11.0
weak
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
yes
yes
yes (pharmacogenomic study)
Comment: mean dexlansoprazole Cmax and AUC values were up to 2 times higher in intermediate compared to extensive metabolizers; in poor metabolizers, mean Cmax was up to 4 times higher and mean AUC was up to 12 times higher compared to extensive metabolizers
Page: 10,12
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
The treatment of gastroesophageal reflux disease with proton-pump inhibitors and its implications on managed care--pharmacoeconomics and its application to antisecretory drugs: a case study.
2001
Advantage of expressing the variations in some digestive parameters as a function of gastric emptying instead of time.
2001
Resolution of Ménétrier's disease after Helicobacter pylori eradicating therapy.
2001
A randomized trial of lansoprazole, amoxycillin, and clarithromycin versus lansoprazole, bismuth, metronidazole and tetracycline in the retreatment of patients failing initial Helicobacter pylori therapy.
2001
Efficacy of Helicobacter pylori eradication therapies: a single centre observational study.
2001
[The effectiveness of 7-day combined Helicobacter eradication therapy in patients with peptic ulcer and chronic gastritis].
2001
Effects of lansoprazole on human gastric lipase secretion and intragastric lipolysis in healthy human volunteers.
2001
[Administration of proton pump inhibitor caused esophageal stenosis in two patients with severe reflux esophagitis].
2001 Aug
Helicobacter pylori eradication treatment does not benefit patients with nonulcer dyspepsia.
2001 Aug
High-dose proton-pump inhibitors as a diagnostic test of gastro-oesophageal reflux disease in endoscopic-negative patients.
2001 Aug
Efficacy of ecabet sodium for Helicobacter pylori eradication triple therapy in comparison with a lansoprazole-based regimen.
2001 Aug
Comparative pharmacokinetics and pharmacodynamics of lansoprazole oral capsules and suspension in healthy subjects.
2001 Aug 15
Healing and relapse rates in gastroesophageal reflux disease treated with the newer proton-pump inhibitors lansoprazole, rabeprazole, and pantoprazole compared with omeprazole, ranitidine, and placebo: evidence from randomized clinical trials.
2001 Jul
Pseudomembranous colitis without diarrhoea following Helicobacter pylori eradication therapy.
2001 Jul
Impact of a formulary change in proton pump inhibitors on health care costs and patients' symptoms.
2001 Jul
Effects on 24-hour intragastric pH: a comparison of lansoprazole administered nasogastrically in apple juice and pantoprazole administered intravenously.
2001 Jul
Cost-effectiveness of proton-pump inhibitors for maintenance therapy of erosive reflux esophagitis.
2001 Jul 15
Follow-up of Helicobacter pylori status by using 13C-urea breath test in nonulcer dyspeptic patients after eradication therapy.
2001 Jun
[Bifid median nerve in the carpal tunnel: integrated imaging].
2001 Jun
CYP2C19 genotype and pharmacokinetics of three proton pump inhibitors in healthy subjects.
2001 Jun
Factors associated with non-response in proton pump inhibitor users: a study of lansoprazole therapy.
2001 Jun
Inhibition of hyphal growth of Candida albicans by activated lansoprazole, a novel benzimidazole proton pump inhibitor.
2001 Jun
New-generation proton pump inhibitors: overcoming the limitations of early-generation agents.
2001 May
Proton pump inhibitor resistance in the treatment of laryngopharyngeal reflux.
2001 Oct
Are children with cystic fibrosis who are treated with a proton-pump inhibitor at risk for vitamin B(12) deficiency?
2001 Sep
Effects of therapy with lansoprazole on intestinal permeability and inflammation in young cystic fibrosis patients.
2001 Sep
Review article: managing the dyspeptic patient--an interactive discussion.
2001 Sep
Review article: tackling the "dyspeptic problem".
2001 Sep
Review article: long-term use of proton pump inhibitors in GORD--help or hindrance?
2001 Sep
Lansoprazole in children: pharmacokinetics and efficacy in reflux oesophagitis.
2001 Sep
Bedtime H2 blockers improve nocturnal gastric acid control in GERD patients on proton pump inhibitors.
2001 Sep
Drug treatments in upper gastrointestinal bleeding: value of endoscopic findings as surrogate end points.
2001 Sep
Does short-term treatment with proton pump inhibitors cause rebound aggravation of symptoms?
2001 Sep
Clinical and ethical concerns about switching patient treatment to "therapeutically interchangeable" medications.
2001 Sep 24
Noninvasive Helicobacter pylori testing for the "test-and-treat" strategy: a decision analysis to assess the effect of past infection on test choice.
2001 Sep 24
Gastroesophageal reflux disease presenting as xerophthalmia.
2001 Sep-Oct
Enantioselective disposition of lansoprazole in extensive and poor metabolizers of CYP2C19.
2002 Jul
Pharmacokinetic differences between the enantiomers of lansoprazole and its metabolite, 5-hydroxylansoprazole, in relation to CYP2C19 genotypes.
2004 Nov
Lansoprazole enantiomer activates human liver microsomal CYP2C9 catalytic activity in a stereospecific and substrate-specific manner.
2005 Feb
Stereoselective inhibition of cytochrome P450 forms by lansoprazole and omeprazole in vitro.
2005 Jan
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

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
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.
Substance Class Chemical
Created
by admin
on Thu Jul 06 00:01:57 UTC 2023
Edited
by admin
on Thu Jul 06 00:01:57 UTC 2023
Record UNII
UYE4T5I70X
Record Status Validated (UNII)
Record Version
  • Download
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
NSC-758710
Code 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 Thu Jul 06 00:01:57 UTC 2023 , Edited by admin on Thu Jul 06 00:01:57 UTC 2023
WHO-VATC QA02BC06
Created by admin on Thu Jul 06 00:01:57 UTC 2023 , Edited by admin on Thu Jul 06 00:01:57 UTC 2023
NCI_THESAURUS C29723
Created by admin on Thu Jul 06 00:01:57 UTC 2023 , Edited by admin on Thu Jul 06 00:01:57 UTC 2023
WHO-ATC A02BC06
Created by admin on Thu Jul 06 00:01:57 UTC 2023 , Edited by admin on Thu Jul 06 00:01:57 UTC 2023
NDF-RT N0000175525
Created by admin on Thu Jul 06 00:01:57 UTC 2023 , Edited by admin on Thu Jul 06 00:01:57 UTC 2023
LIVERTOX 290
Created by admin on Thu Jul 06 00:01:57 UTC 2023 , Edited by admin on Thu Jul 06 00:01:57 UTC 2023
Code System Code Type Description
PUBCHEM
9578005
Created by admin on Thu Jul 06 00:01:57 UTC 2023 , Edited by admin on Thu Jul 06 00:01:57 UTC 2023
PRIMARY
RXCUI
816346
Created by admin on Thu Jul 06 00:01:57 UTC 2023 , Edited by admin on Thu Jul 06 00:01:57 UTC 2023
PRIMARY RxNorm
EVMPD
SUB31929
Created by admin on Thu Jul 06 00:01:57 UTC 2023 , Edited by admin on Thu Jul 06 00:01:57 UTC 2023
PRIMARY
CAS
138530-94-6
Created by admin on Thu Jul 06 00:01:57 UTC 2023 , Edited by admin on Thu Jul 06 00:01:57 UTC 2023
PRIMARY
NSC
758710
Created by admin on Thu Jul 06 00:01:57 UTC 2023 , Edited by admin on Thu Jul 06 00:01:57 UTC 2023
PRIMARY
DAILYMED
UYE4T5I70X
Created by admin on Thu Jul 06 00:01:57 UTC 2023 , Edited by admin on Thu Jul 06 00:01:57 UTC 2023
PRIMARY
USAN
SS-95
Created by admin on Thu Jul 06 00:01:57 UTC 2023 , Edited by admin on Thu Jul 06 00:01:57 UTC 2023
PRIMARY
DRUG BANK
DB05351
Created by admin on Thu Jul 06 00:01:57 UTC 2023 , Edited by admin on Thu Jul 06 00:01:57 UTC 2023
PRIMARY
MERCK INDEX
M6683
Created by admin on Thu Jul 06 00:01:57 UTC 2023 , Edited by admin on Thu Jul 06 00:01:57 UTC 2023
PRIMARY Merck Index
FDA UNII
UYE4T5I70X
Created by admin on Thu Jul 06 00:01:57 UTC 2023 , Edited by admin on Thu Jul 06 00:01:57 UTC 2023
PRIMARY
NCI_THESAURUS
C73192
Created by admin on Thu Jul 06 00:01:57 UTC 2023 , Edited by admin on Thu Jul 06 00:01:57 UTC 2023
PRIMARY
SMS_ID
100000124233
Created by admin on Thu Jul 06 00:01:57 UTC 2023 , Edited by admin on Thu Jul 06 00:01:57 UTC 2023
PRIMARY
ChEMBL
CHEMBL1201863
Created by admin on Thu Jul 06 00:01:57 UTC 2023 , Edited by admin on Thu Jul 06 00:01:57 UTC 2023
PRIMARY
IUPHAR
5487
Created by admin on Thu Jul 06 00:01:57 UTC 2023 , Edited by admin on Thu Jul 06 00:01:57 UTC 2023
PRIMARY
DRUG CENTRAL
4162
Created by admin on Thu Jul 06 00:01:57 UTC 2023 , Edited by admin on Thu Jul 06 00:01:57 UTC 2023
PRIMARY
LACTMED
Dexlansoprazole
Created by admin on Thu Jul 06 00:01:57 UTC 2023 , Edited by admin on Thu Jul 06 00:01:57 UTC 2023
PRIMARY
INN
8524
Created by admin on Thu Jul 06 00:01:57 UTC 2023 , Edited by admin on Thu Jul 06 00:01:57 UTC 2023
PRIMARY
WIKIPEDIA
DEXLANSOPRAZOLE
Created by admin on Thu Jul 06 00:01:57 UTC 2023 , Edited by admin on Thu Jul 06 00:01:57 UTC 2023
PRIMARY
Related Record Type Details
TARGET -> INHIBITOR
BINDER->LIGAND
BINDING
RACEMATE -> ENANTIOMER
SOLVATE->ANHYDROUS
SALT/SOLVATE -> PARENT
Related Record Type Details
METABOLITE -> PARENT
MINOR
FECAL
METABOLITE ACTIVE -> PRODRUG
METABOLITE -> PARENT
MINOR
FECAL
METABOLITE -> PARENT
In poor metabolizer; mediator: CYP3A
MAJOR
PLASMA
METABOLITE -> PARENT
Minor in plasma
MAJOR
FECAL
METABOLITE -> PARENT
EM sujects
MAJOR
PLASMA; URINE
METABOLITE -> PARENT
EM Subjects
MAJOR
PLASMA; URINE
METABOLITE -> PARENT
PM sujects
MAJOR
URINE
METABOLITE -> PARENT
Extensive metabolizers
MINOR
URINE
METABOLITE -> PARENT
EM Subjects
MAJOR
PLASMA
METABOLITE ACTIVE -> PRODRUG
METABOLITE -> PARENT
MINOR
FECAL; PLASMA
METABOLITE -> PARENT
MINOR
PLASMA; URINE
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC