Dexlansoprazole

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Identification

Summary

Dexlansoprazole is a proton pump inhibitor used to treat erosive esophagitis, heartburn, and gastroesophageal reflux disease (GERD).

Brand Names

Dexilant

Generic Name

Dexlansoprazole

DrugBank Accession Number

DB05351

Background

Dexlansoprazole is a new-generation proton pump inhibitor (PPI) used for the management of symptoms associated with gastroesophageal reflux disease (GERD) and erosive esophagitis. Dexlansoprazole is the R-enantiomer of Lansoprazole, which is composed of a racemic mixture of the R- and S-enantiomers. Compared to the older generation of PPIs (which includes Pantoprazole, Omeprazole, and Lansoprazole),⁶ dexlansoprazole has a unique pharmacokinetic profile due to its delayed-release and dual-delivery release system: This aims to address some limitations of the older-generation PPIs, such as short plasma half-life and the need for meal-associated dosing.^1,3,6,9 Dexlansoprazole inhibits the final step in gastric acid production by blocking the (H+, K+)-ATPase enzyme.¹⁰

Type

Small Molecule

Groups

Approved, Investigational

Structure

Similar Structures

Weight: Average: 369.36
Monoisotopic: 369.075882366
Chemical Formula: C₁₆H₁₄F₃N₃O₂S

Synonyms

(+)-2-((R)-((3-METHYL-4-(2,2,2-TRIFLUOROETHOXY)PYRIDIN-2-YL)METHYL)SULFINYL)-1H-BENZIMIDAZOLE
(R)-LANSOPRAZOLE
1H-BENZIMIDAZOLE, 2-((R)-((3-METHYL-4-(2,2,2-TRIFLUOROETHOXY)-2-PYRIDINYL)METHYL)SULFINYL)-
2-((R)-((3-methyl-4-(2,2,2-trifluoroethoxy)-2-pyridinyl)methyl)sulfinyl)-1H-benzimidazole
Dexlansoprazole
LANSOPRAZOLE R-FORM
LANSOPRAZOLE, (R)-

External IDs

NSC-758710
T-168390
TAK 390
TAK-390
TAK-390MR
TAK390

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Pharmacology

Indication

Dexlansoprazole is a proton pump inhibitor (PPI) indicated for the:

Healing of all grades of erosive esophagitis (EE) for up to eight weeks in patients 12 years of age and older.¹⁰
Maintenance of healed EE and relief of heartburn for up to six months in adults and 16 weeks in patients 12 to 17 years of age.^10,11
Treatment of heartburn associated with symptomatic non-erosive gastroesophageal reflux disease (GERD) for four weeks in patients 12 years of age and older.^10,11

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Associated Conditions

Indication Type	Indication	Approval Level	Age Group	Dose Form
Treatment of	Erosive esophagitis	••••••••••••		•••••••• ••••••• •••••••
Management of	Heartburn	••••••••••••	•••••	•••••••• ••••••• •••••••• ••••••• •••••• ••••••••••••••• ••••••• •••••••
Management of	Heartburn	••••••••••••	••••••••••	•••••••• ••••••• •••••••• ••••••• •••••• ••••••••••••••• ••••••• •••••••
Management of	Healed erosive esophagitis	••••••••••••	•••••	•••••••• ••••••• •••••••• ••••••• •••••• ••••••••••••••• ••••••• •••••••
Management of	Healed erosive esophagitis	••••••••••••	••••••••••	•••••••• ••••••• •••••••• ••••••• •••••• ••••••••••••••• ••••••• •••••••

Contraindications & Blackbox Warnings

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Pharmacodynamics

Dexlansoprazole is a proton pump inhibitor (PPI) that suppresses both basal and stimulated gastric acid secretion.¹⁰ PPIs are associated with a risk for a rebound effect and a short-term increase in hypersecretion; thus, such risk cannot be excluded with dexlansoprazole.⁸ With long-term use, PPIs are also associated with a risk of increased susceptibility to bacterial infections, vitamin B12 and iron deficiency, and hypomagnesemia and hypocalcemia, possibly leading to osteoporosis and bone fractures.⁷

Dexlansoprazole is reported to interfere with the secretin stimulation test and create false positive urine screening tests for tetrahydrocannabinol. Dexlansoprazole can increase gastrin levels, which can cause enterochromaffin-like cell hyperplasia and increase serum CgA levels. Increased CgA levels may cause false positive results in diagnostic investigations for neuroendocrine tumours.¹⁰

Mechanism of action

Dexlansoprazole suppresses gastric acid secretion by blocking the final step of acid production. It inhibits the H/K ATPase at the secretory surface of the gastric parietal cell, which is involved in the secretion of hydrochloric acid.¹⁰ H/K ATPase is a proton pump responsible for hydrolyzing ATP and exchanging H⁺ ions from the cytoplasm for K⁺ ions in the secretory canaliculus: this action results in hydrochloric acid secretion into the gastric lumen.²

Target	Actions	Organism
APotassium-transporting ATPase alpha chain 1	inhibitor	Humans
APotassium-transporting ATPase subunit beta	inhibitor	Humans
UN(G),N(G)-dimethylarginine dimethylaminohydrolase 1	Not Available	Humans

Absorption

The dual delayed-release formulation of dexlansoprazole results in a plasma concentration-time profile with two distinct peaks; the first peak occurs one to two hours after administration, followed by a second peak within four to five hours. About 25% of the dose is released at the pH level of 5.5 in the proximal duodenum, while the other 75% is released in the distal small intestine at the pH level of 6.75.^2,10

After oral administration of dexlansoprazole 30 or 60 mg to healthy subjects and symptomatic GERD patients, mean C_max and AUC values of dexlansoprazole increased approximately dose-proportionally. Following administration of 30 mg in healthy adults, the mean (%CV) C_max and AUC were 658 (40%) ng/mL and 3275 (47%) ng x h/mL, respectively. At a dose of 60 mg, the mean (%CV) C_max and AUC were 1397 (51%) ng/mL and 6529 (60%) ng x h/mL, respectively. In healthy subjects, food increased C_max by 12 to 55% and AUC by 9 to 37%. The effect of food on Tmax varied, as both an increase and a decrease was observed.¹⁰

Volume of distribution

The apparent volume of distribution (Vz/F) after multiple doses in symptomatic GERD patients was 40 L.¹⁰

Protein binding

Plasma protein binding of dexlansoprazole ranged from 96 to 99% in healthy subjects and was independent of concentration from 0.01 to 20 mcg/mL.¹⁰

Metabolism

Dexlansoprazole is extensively metabolized in the liver. It undergoes oxidation and reduction, followed by subsequent sulfation, glucuronidation, and glutathione conjugation to form inactive metabolites. Oxidative metabolites are formed from CYP2C19-mediated hydroxylation and CYP3A4-mediated oxidation to the sulfone.^5,10

CYP2C19 is a polymorphic liver enzyme which exhibits three phenotypes in the metabolism of CYP2C19 substrates: extensive metabolizers (1/1), intermediate metabolizers (*1/mutant) and poor metabolizers (mutant/mutant). Dexlansoprazole is the major circulating component in plasma regardless of CYP2C19 metabolizer status. In CYP2C19 intermediate and extensive metabolizers, the major plasma metabolites are 5-hydroxy dexlansoprazole and its glucuronide conjugate, while in CYP2C19 poor metabolizers dexlansoprazole sulfone is the major plasma metabolite.¹⁰

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Dexlansoprazole

Route of elimination

Dexlansoprazole does not appear to be eliminated unchanged in the urine.^4,10 Following the administration of [14C] dexlansoprazole to six healthy male subjects, approximately 50.7% (standard deviation (SD): 9.0%) of the administered radioactivity was excreted in urine and 47.6% (SD: 7.3%) in the feces.¹⁰

Half-life

Dexlansoprazole is eliminated with a half-life of approximately one to two hours.^4,10

Clearance

Apparent clearance (CL/F) in healthy subjects was 11.4 to 11.6 L/hour, respectively, after five days of 30 or 60 mg once daily administration.¹⁰

Adverse Effects

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Toxicity

Oral LD₅₀ value in mice, rats and dogs is reported to be > 5000 mg/kg.¹²

There have been no reports of significant overdose with dexlansoprazole. Multiple doses of 120 mg and a single dose of 300 mg did not result in death or other severe adverse events; however, serious adverse events of hypertension have been reported in association with twice daily doses of 60 mg. Nonserious adverse reactions observed with twice daily doses of 60 mg include hot flashes, contusion, oropharyngeal pain, and weight loss. Dexlansoprazole is not expected to be removed from the circulation by hemodialysis. In the event of over-exposure, treatment should be symptomatic and supportive.¹⁰

Pathways

Not Available

Pharmacogenomic Effects/ADRs

Interacting Gene/Enzyme	Allele name	Genotype(s)	Defining Change(s)	Type(s)	Description	Details
Cytochrome P450 2C19	CYP2C19*2A	Not Available	681G>A	Effect Inferred	Poor drug metabolizer.	Details
Cytochrome P450 2C19	CYP2C19*2B	Not Available	681G>A	Effect Inferred	Poor drug metabolizer.	Details
Cytochrome P450 2C19	CYP2C19*3	Not Available	636G>A	Effect Inferred	Poor drug metabolizer.	Details
Cytochrome P450 2C19	CYP2C19*4	Not Available	1A>G	Effect Inferred	Poor drug metabolizer.	Details
Cytochrome P450 2C19	CYP2C19*5	Not Available	1297C>T	Effect Inferred	Poor drug metabolizer.	Details
Cytochrome P450 2C19	CYP2C19*6	Not Available	395G>A	Effect Inferred	Poor drug metabolizer.	Details
Cytochrome P450 2C19	CYP2C19*7	Not Available	19294T>A	Effect Inferred	Poor drug metabolizer.	Details
Cytochrome P450 2C19	CYP2C19*22	Not Available	557G>C / 991A>G	Effect Inferred	Poor drug metabolizer.	Details
Cytochrome P450 2C19	CYP2C19*24	Not Available	99C>T / 991A>G … show all	Effect Inferred	Poor drug metabolizer.	Details
Cytochrome P450 2C19	CYP2C19*35	Not Available	12662A>G	Effect Inferred	Poor drug metabolizer.	Details

Interactions

Drug Interactions

This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.

Drug	Interaction
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Abametapir	The serum concentration of Dexlansoprazole can be increased when it is combined with Abametapir.
Abatacept	The metabolism of Dexlansoprazole can be increased when combined with Abatacept.
Abrocitinib	The metabolism of Abrocitinib can be decreased when combined with Dexlansoprazole.
Acenocoumarol	The risk or severity of bleeding can be increased when Dexlansoprazole is combined with Acenocoumarol.
Adalimumab	The metabolism of Dexlansoprazole can be increased when combined with Adalimumab.

Food Interactions

Avoid St. John's Wort. It may induce the CYP3A4 metabolism of dexlansoprazole, possibly leading to reduced efficacy.
Take with or without food. Dexlansoprazole's dual delayed release formulation allows it to be taken without regard to food in contrast to other PPIs.

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Product Ingredients

Ingredient	UNII	CAS	InChI Key
Dexlansoprazole sesquihydrate	HS2S9VK3NH	313640-86-7	XTQWZVSRVXCIGB-BBBDYAHLSA-N

Product Images

Brand Name Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Dexilant	Capsule, delayed release	60 mg/1	Oral	Takeda Pharmaceuticals America, Inc.	2010-04-12	Not applicable
Dexilant	Capsule, delayed release	60 mg/1	Oral	Cardinal Health 107, LLC	2010-04-12	2025-04-30
Dexilant	Capsule, delayed release	60 mg	Nasogastric; Oral	Takeda	2010-08-05	Not applicable
Dexilant	Capsule, delayed release	60 mg/1	Oral	Physicians Total Care, Inc.	2010-08-19	Not applicable
Dexilant	Capsule, delayed release	30 mg/1	Oral	Takeda Pharmaceuticals America, Inc.	2010-04-12	Not applicable

Generic Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Apo-dexlansoprazole	Capsule, delayed release	30 mg	Nasogastric; Oral	Apotex Corporation	2024-02-26	Not applicable
Apo-dexlansoprazole	Capsule, delayed release	60 mg	Nasogastric; Oral	Apotex Corporation	2024-02-26	Not applicable
Dexlansoprazole	Capsule, delayed release	60 mg/1	Oral	ENDO USA, Inc.	2022-11-22	Not applicable
Dexlansoprazole	Capsule, delayed release pellets	30 mg/1	Oral	Mylan Pharmaceuticals Inc.	2024-01-22	Not applicable
Dexlansoprazole	Capsule, delayed release	30 mg/1	Oral	ENDO USA, Inc.	2023-06-10	Not applicable

Mixture Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End
DEXGARD 30/30 MG MR KAPSUL, 30 ADET	Dexlansoprazole (30 mg) + Domperidone (30 mg)	Capsule	Oral	NUVOMED İLAÇ SAN.TİC. A.Ş.	2012-07-31	Not applicable
DEXGARD 30/30 MG MR KAPSUL, 60 ADET	Dexlansoprazole (30 mg) + Domperidone (30 mg)	Capsule	Oral	NUVOMED İLAÇ SAN.TİC. A.Ş.	2012-07-31	Not applicable
DUEDOM 30/10 MG KAPSÜL, 30 ADET	Dexlansoprazole (30 mg) + Domperidone (10 mg)	Capsule	Oral	CELTİS İLAÇ SAN. VE TİC. A.Ş.	2011-12-22	Not applicable
DUEDOM 60/10 MG KAPSÜL, 30 ADET	Dexlansoprazole (60 mg) + Domperidone (10 mg)	Capsule	Oral	CELTİS İLAÇ SAN. VE TİC. A.Ş.	2011-12-22	Not applicable

Chemical Identifiers

UNII: UYE4T5I70X
CAS number: 138530-94-6
InChI Key: MJIHNNLFOKEZEW-RUZDIDTESA-N
InChI: 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
IUPAC Name: 2-[(R)-[3-methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]methanesulfinyl]-1H-1,3-benzodiazole
SMILES: CC1=C(OCC(F)(F)F)C=CN=C1C[S@@](=O)C1=NC2=CC=CC=C2N1

References

General References

Behm BW, Peura DA: Dexlansoprazole MR for the management of gastroesophageal reflux disease. Expert Rev Gastroenterol Hepatol. 2011 Aug;5(4):439-45. doi: 10.1586/egh.11.37. [Article]
Skrzydlo-Radomanska B, Radwan P: Dexlansoprazole - a new-generation proton pump inhibitor. Prz Gastroenterol. 2015;10(4):191-6. doi: 10.5114/pg.2015.56109. Epub 2015 Dec 16. [Article]
Frye JW, Peura DA: Managing gastroesophageal reflux disease - comparative efficacy and outcomes of dexlansoprazole MR. Ther Clin Risk Manag. 2015 Oct 30;11:1649-56. doi: 10.2147/TCRM.S66680. eCollection 2015. [Article]
Wittbrodt ET, Baum C, Peura DA: Delayed release dexlansoprazole in the treatment of GERD and erosive esophagitis. Clin Exp Gastroenterol. 2009;2:117-28. Epub 2009 Nov 17. [Article]
Grabowski B, Lee RD: Absorption, distribution, metabolism and excretion of [14C]dexlansoprazole in healthy male subjects. Clin Drug Investig. 2012 May 1;32(5):319-32. doi: 10.2165/11630930-000000000-00000. [Article]
Tytgat GN: Shortcomings of the first-generation proton pump inhibitors. Eur J Gastroenterol Hepatol. 2001 May;13 Suppl 1:S29-33. [Article]
Haastrup PF, Thompson W, Sondergaard J, Jarbol DE: Side Effects of Long-Term Proton Pump Inhibitor Use: A Review. Basic Clin Pharmacol Toxicol. 2018 Aug;123(2):114-121. doi: 10.1111/bcpt.13023. Epub 2018 May 24. [Article]
Reimer C, Sondergaard B, Hilsted L, Bytzer P: Proton-pump inhibitor therapy induces acid-related symptoms in healthy volunteers after withdrawal of therapy. Gastroenterology. 2009 Jul;137(1):80-7, 87.e1. doi: 10.1053/j.gastro.2009.03.058. Epub 2009 Apr 10. [Article]
Shin JM, Kim N: Pharmacokinetics and pharmacodynamics of the proton pump inhibitors. J Neurogastroenterol Motil. 2013 Jan;19(1):25-35. doi: 10.5056/jnm.2013.19.1.25. Epub 2013 Jan 8. [Article]
DailyMed Label: DEXILANT (dexlansoprazole) delayed-release capsules, for oral use [Link]
FDA Approved Drug Products: DEXILANT (dexlansoprazole) Oral Delayed-release capsules or DEXILANT SOLUTAB (dexlansoprazole) delayed-release orally disintegrating tablets (October 2016) [Link]
TWi Pharmaceuticals: Dexlansoprazole MSDS [Link]

External Links

PubChem Compound: 9578005
PubChem Substance: 347827723
ChemSpider: 7852369
BindingDB: 50247930
RxNav: 816346
ChEBI: 135931
ChEMBL: CHEMBL1201863
ZINC: ZINC000003830986
PharmGKB: PA166110257
Wikipedia: Dexlansoprazole

Clinical Trials

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Phase	Status	Purpose	Conditions	Count	Start Date	Why Stopped	100+ additional columns
Unlock 175K+ rows when you subscribe.View sample data
Not Available	Completed	Not Available	Infections, Helicobacter	1	somestatus	stop reason	just information to hide
Not Available	Completed	Treatment	Helicobacter Pylori Infection	2	somestatus	stop reason	just information to hide
Not Available	Completed	Treatment	Suspected Eosinophilic Esophagitis	1	somestatus	stop reason	just information to hide
Not Available	Terminated	Treatment	Laryngopharyngeal Reflux (LPR)	1	somestatus	stop reason	just information to hide
Not Available	Unknown Status	Treatment	Compare the Response Rate of Atypical GERD After PPI Therapy	1	somestatus	stop reason	just information to hide

Pharmacoeconomics

Manufacturers

Not Available

Packagers

Not Available

Dosage Forms

Form	Route	Strength
Tablet		30 mg
Tablet		60 mg
Capsule	Oral
Capsule	Oral	60.00 mg
Capsule, delayed release	Nasogastric; Oral	30 mg
Capsule, delayed release	Nasogastric; Oral	60 mg
Capsule, delayed release	Oral	60 mg/1
Capsule	Oral	30 mg
Capsule	Oral	60 mg
Capsule, delayed release		60 mg
Capsule, extended release	Oral	30 MG
Capsule, extended release	Oral	60 MG
Capsule, delayed release	Oral	30 mg
Capsule, delayed release	Oral	60 mg
Capsule, delayed release	Oral
Tablet, orally disintegrating, delayed release	Oral	30 mg/1
Capsule, delayed release		30 mg
Capsule	Oral	7.500 mg
Capsule, delayed release pellets	Oral	30 mg/1
Capsule, delayed release pellets	Oral	60 mg/1
Capsule, coated	Oral	30 mg
Capsule, coated	Oral	3000000 mg
Capsule, coated	Oral	6000000 mg
Capsule, delayed release	Oral	6000000 mg
Capsule, delayed release	Oral	30 mg/1
Capsule, coated	Oral	60 mg

Prices

Not Available

Patents

Patent Number	Pediatric Extension	Approved	Expires (estimated)
CA1327010	No	1994-02-15	2011-02-15
CA2375201	No	2010-02-09	2020-06-15
US7399485	Yes	2008-07-15	2018-11-26
US6328994	Yes	2001-12-11	2019-11-17
US7875292	Yes	2011-01-25	2019-11-17
US7431942	Yes	2008-10-07	2019-11-17
US6462058	Yes	2002-10-08	2020-12-15
US6939971	Yes	2005-09-06	2020-12-15
US8173158	Yes	2012-05-08	2030-09-17
US6664276	Yes	2003-12-16	2023-07-30
US8784885	Yes	2014-07-22	2024-04-15
US9233103	No	2016-01-12	2032-03-05
US9011926	No	2015-04-21	2026-02-24
US9238029	No	2016-01-19	2026-01-17
US8722084	Yes	2014-05-13	2024-04-15
US9145389	No	2015-09-29	2020-06-15
US8871273	Yes	2014-10-28	2028-07-11
US8461187	Yes	2013-06-11	2026-07-17
US8105626	Yes	2012-01-31	2027-03-27
US7285668	Yes	2007-10-23	2020-12-15
US7790755	Yes	2010-09-07	2027-02-02
US9241910	No	2016-01-26	2029-03-10
US6238994	Yes	2001-05-29	2019-11-17

Properties

State

Solid

Experimental Properties

Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.25 mg/mL	ALOGPS
logP	2.84	ALOGPS
logP	3.03	Chemaxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	9.35	Chemaxon
pKa (Strongest Basic)	4.16	Chemaxon
Physiological Charge	0	Chemaxon
Hydrogen Acceptor Count	4	Chemaxon
Hydrogen Donor Count	1	Chemaxon
Polar Surface Area	67.87 Å²	Chemaxon
Rotatable Bond Count	6	Chemaxon
Refractivity	87.61 m³·mol^-1	Chemaxon
Polarizability	34.5 Å³	Chemaxon
Number of Rings	3	Chemaxon
Bioavailability	1	Chemaxon
Rule of Five	Yes	Chemaxon
Ghose Filter	Yes	Chemaxon
Veber's Rule	No	Chemaxon
MDDR-like Rule	Yes	Chemaxon

Predicted ADMET Features

Not Available

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	splash10-0fk9-0059000000-f06d77d09a86f5e2bf71
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	splash10-0v59-0769000000-b68e645e752cc42ba812
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	splash10-014i-0900000000-2b57a28f448d017c174c
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	splash10-014l-1933000000-25b5d7be37adf65fa45f
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	splash10-0uyr-0930000000-bb49b5d18d287fcc5ad3
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	splash10-014i-0910000000-674886b87ab10a6d4082
Predicted 1H NMR Spectrum	1D NMR	Not Applicable
Predicted 13C NMR Spectrum	1D NMR	Not Applicable

Chromatographic Properties

Collision Cross Sections (CCS)

Adduct	CCS Value (Å²)	Source type	Source
[M-H]-	175.42035	predicted	DeepCCS 1.0 (2019)
[M+H]+	177.77835	predicted	DeepCCS 1.0 (2019)
[M+Na]+	184.21729	predicted	DeepCCS 1.0 (2019)

Targets

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Details1. Potassium-transporting ATPase alpha chain 1

Kind: Protein
Organism: Humans
Pharmacological action: Yes
Actions: Inhibitor

General Function: The catalytic subunit of the gastric H(+)/K(+) ATPase pump which transports H(+) ions in exchange for K(+) ions across the apical membrane of parietal cells. Uses ATP as an energy source to pump H(+) ions to the gastric lumen while transporting K(+) ion from the lumen into the cell (By similarity). Remarkably generates a million-fold proton gradient across the gastric parietal cell membrane, acidifying the gastric juice down to pH 1 (By similarity). Within a transport cycle, the transfer of a H(+) ion across the membrane is coupled to ATP hydrolysis and is associated with a transient phosphorylation that shifts the pump conformation from inward-facing (E1) to outward-facing state (E2). The release of the H(+) ion in the stomach lumen is followed by binding of K(+) ion converting the pump conformation back to the E1 state (By similarity)
Specific Function: ATP binding
Gene Name: ATP4A
Uniprot ID: P20648
Uniprot Name: Potassium-transporting ATPase alpha chain 1
Molecular Weight: 114117.74 Da

References

Shin JM, Kim N: Pharmacokinetics and pharmacodynamics of the proton pump inhibitors. J Neurogastroenterol Motil. 2013 Jan;19(1):25-35. doi: 10.5056/jnm.2013.19.1.25. Epub 2013 Jan 8. [Article]
Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
FDA Approved Drug Products: DEXILANT (dexlansoprazole) Oral Delayed-release capsules or DEXILANT SOLUTAB (dexlansoprazole) delayed-release orally disintegrating tablets (October 2016) [Link]

Details2. Potassium-transporting ATPase subunit beta

Kind: Protein
Organism: Humans
Pharmacological action: Yes
Actions: Inhibitor

General Function: The beta subunit of the gastric H(+)/K(+) ATPase pump which transports H(+) ions in exchange for K(+) ions across the apical membrane of parietal cells. Plays a structural and regulatory role in the assembly and membrane targeting of a functionally active pump (By similarity). Within a transport cycle, the transfer of a H(+) ion across the membrane is coupled to ATP hydrolysis and is associated with a transient phosphorylation of the alpha subunit that shifts the pump conformation from inward-facing (E1) to outward-facing state (E2). Interacts with the phosphorylation domain of the alpha subunit and functions as a ratchet, stabilizing the lumenal-open E2 conformation and preventing the reverse reaction of the transport cycle (By similarity)
Specific Function: ATPase activator activity
Gene Name: ATP4B
Uniprot ID: P51164
Uniprot Name: Potassium-transporting ATPase subunit beta
Molecular Weight: 33366.95 Da

References

Shin JM, Kim N: Pharmacokinetics and pharmacodynamics of the proton pump inhibitors. J Neurogastroenterol Motil. 2013 Jan;19(1):25-35. doi: 10.5056/jnm.2013.19.1.25. Epub 2013 Jan 8. [Article]
FDA Approved Drug Products: DEXILANT (dexlansoprazole) Oral Delayed-release capsules or DEXILANT SOLUTAB (dexlansoprazole) delayed-release orally disintegrating tablets (October 2016) [Link]

Details3. N(G),N(G)-dimethylarginine dimethylaminohydrolase 1

Kind: Protein
Organism: Humans
Pharmacological action: Unknown

General Function: Hydrolyzes N(G),N(G)-dimethyl-L-arginine (ADMA) and N(G)-monomethyl-L-arginine (MMA) which act as inhibitors of NOS. Has therefore a role in the regulation of nitric oxide generation
Specific Function: amino acid binding
Gene Name: DDAH1
Uniprot ID: O94760
Uniprot Name: N(G),N(G)-dimethylarginine dimethylaminohydrolase 1
Molecular Weight: 31121.5 Da

References

Ghebremariam YT, LePendu P, Lee JC, Erlanson DA, Slaviero A, Shah NH, Leiper J, Cooke JP: Unexpected effect of proton pump inhibitors: elevation of the cardiovascular risk factor asymmetric dimethylarginine. Circulation. 2013 Aug 20;128(8):845-53. doi: 10.1161/CIRCULATIONAHA.113.003602. Epub 2013 Jul 3. [Article]
Tommasi S, Elliot DJ, Hulin JA, Lewis BC, McEvoy M, Mangoni AA: Human dimethylarginine dimethylaminohydrolase 1 inhibition by proton pump inhibitors and the cardiovascular risk marker asymmetric dimethylarginine: in vitro and in vivo significance. Sci Rep. 2017 Jun 6;7(1):2871. doi: 10.1038/s41598-017-03069-1. [Article]

Enzymes

Details1. Cytochrome P450 2C19

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate
Inhibitor
Curator comments: AAlthough in vitro studies indicated that dexlansoprazole has the potential to inhibit CYP2C19 in vivo, an in vivo drug- drug interaction study in mainly CYP2C19 extensive and intermediate metabolizers has shown that dexlansoprazole does not affect the pharmacokinetics of CYP2C19 substrates.

General Function: A cytochrome P450 monooxygenase involved in the metabolism of polyunsaturated fatty acids (PUFA) (PubMed:18577768, PubMed:19965576, PubMed:20972997). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:18577768, PubMed:19965576, PubMed:20972997). Catalyzes the hydroxylation of carbon-hydrogen bonds. Hydroxylates PUFA specifically at the omega-1 position (PubMed:18577768). Catalyzes the epoxidation of double bonds of PUFA (PubMed:19965576, PubMed:20972997). Also metabolizes plant monoterpenes such as limonene. Oxygenates (R)- and (S)-limonene to produce carveol and perillyl alcohol (PubMed:11950794). Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine. Hydroxylates fenbendazole at the 4' position (PubMed:23959307)
Specific Function: (R)-limonene 6-monooxygenase activity
Gene Name: CYP2C19
Uniprot ID: P33261
Uniprot Name: Cytochrome P450 2C19
Molecular Weight: 55944.565 Da

References

Goh KL, Choi MG, Hsu PI, Chun HJ, Mahachai V, Kachintorn U, Leelakusolvong S, Kim N, Rani AA, Wong BC, Wu J, Chiu CT, Shetty V, Bocobo JC, Chan MM, Lin JT: Pharmacological and Safety Profile of Dexlansoprazole: A New Proton Pump Inhibitor - Implications for Treatment of Gastroesophageal Reflux Disease in the Asia Pacific Region. J Neurogastroenterol Motil. 2016 Jul 30;22(3):355-66. doi: 10.5056/jnm15150. [Article]
Li XQ, Andersson TB, Ahlstrom M, Weidolf L: Comparison of inhibitory effects of the proton pump-inhibiting drugs omeprazole, esomeprazole, lansoprazole, pantoprazole, and rabeprazole on human cytochrome P450 activities. Drug Metab Dispos. 2004 Aug;32(8):821-7. [Article]
FDA Approved Drug Products: DEXILANT (dexlansoprazole) Oral Delayed-release capsules or DEXILANT SOLUTAB (dexlansoprazole) delayed-release orally disintegrating tablets (October 2016) [Link]

Details2. Cytochrome P450 3A4

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate

General Function: A cytochrome P450 monooxygenase involved in the metabolism of sterols, steroid hormones, retinoids and fatty acids (PubMed:10681376, PubMed:11093772, PubMed:11555828, PubMed:12865317, PubMed:14559847, PubMed:15373842, PubMed:15764715, PubMed:19965576, PubMed:20702771, PubMed:21490593, PubMed:21576599). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase). Catalyzes the hydroxylation of carbon-hydrogen bonds (PubMed:12865317, PubMed:14559847, PubMed:15373842, PubMed:15764715, PubMed:21490593, PubMed:21576599, PubMed:2732228). Exhibits high catalytic activity for the formation of hydroxyestrogens from estrone (E1) and 17beta-estradiol (E2), namely 2-hydroxy E1 and E2, as well as D-ring hydroxylated E1 and E2 at the C-16 position (PubMed:11555828, PubMed:12865317, PubMed:14559847). Plays a role in the metabolism of androgens, particularly in oxidative deactivation of testosterone (PubMed:15373842, PubMed:15764715, PubMed:22773874, PubMed:2732228). Metabolizes testosterone to less biologically active 2beta- and 6beta-hydroxytestosterones (PubMed:15373842, PubMed:15764715, PubMed:2732228). Contributes to the formation of hydroxycholesterols (oxysterols), particularly A-ring hydroxylated cholesterol at the C-4beta position, and side chain hydroxylated cholesterol at the C-25 position, likely contributing to cholesterol degradation and bile acid biosynthesis (PubMed:21576599). Catalyzes bisallylic hydroxylation of polyunsaturated fatty acids (PUFA) (PubMed:9435160). Catalyzes the epoxidation of double bonds of PUFA with a preference for the last double bond (PubMed:19965576). Metabolizes endocannabinoid arachidonoylethanolamide (anandamide) to 8,9-, 11,12-, and 14,15-epoxyeicosatrienoic acid ethanolamides (EpETrE-EAs), potentially modulating endocannabinoid system signaling (PubMed:20702771). Plays a role in the metabolism of retinoids. Displays high catalytic activity for oxidation of all-trans-retinol to all-trans-retinal, a rate-limiting step for the biosynthesis of all-trans-retinoic acid (atRA) (PubMed:10681376). Further metabolizes atRA toward 4-hydroxyretinoate and may play a role in hepatic atRA clearance (PubMed:11093772). Responsible for oxidative metabolism of xenobiotics. Acts as a 2-exo-monooxygenase for plant lipid 1,8-cineole (eucalyptol) (PubMed:11159812). Metabolizes the majority of the administered drugs. Catalyzes sulfoxidation of the anthelmintics albendazole and fenbendazole (PubMed:10759686). Hydroxylates antimalarial drug quinine (PubMed:8968357). Acts as a 1,4-cineole 2-exo-monooxygenase (PubMed:11695850). Also involved in vitamin D catabolism and calcium homeostasis. Catalyzes the inactivation of the active hormone calcitriol (1-alpha,25-dihydroxyvitamin D(3)) (PubMed:29461981)
Specific Function: 1,8-cineole 2-exo-monooxygenase activity
Gene Name: CYP3A4
Uniprot ID: P08684
Uniprot Name: Cytochrome P450 3A4
Molecular Weight: 57342.67 Da

References

FDA Approved Drug Products: DEXILANT (dexlansoprazole) Oral Delayed-release capsules or DEXILANT SOLUTAB (dexlansoprazole) delayed-release orally disintegrating tablets (October 2016) [Link]

Drug created at November 18, 2007 18:24 / Updated at April 23, 2024 11:38

Dexlansoprazole

Identification

Structure for Dexlansoprazole (DB05351)

Pharmacology

Interactions

Products

Categories

Chemical Identifiers

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Clinical Trials

Clinical Trial & Rare Diseases Add-on Data Package

Pharmacoeconomics

Properties

Spectra

Collision Cross Sections (CCS)

Targets

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Enzymes

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