TENATOPRAZOLE

Details

Stereochemistry	RACEMIC
Molecular Formula	C16H18N4O3S
Molecular Weight	346.404
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COC1=CC=C2NC(=NC2=N1)[S+]([O-])CC3=NC=C(C)C(OC)=C3C

InChI

InChIKey=ZBFDAUIVDSSISP-UHFFFAOYSA-N

InChI=1S/C16H18N4O3S/c1-9-7-17-12(10(2)14(9)23-4)8-24(21)16-18-11-5-6-13(22-3)19-15(11)20-16/h5-7H,8H2,1-4H3,(H,18,19,20)

HIDE SMILES / InChI

Molecular Formula	C16H18N4O3S
Molecular Weight	346.404
Charge	0
Count

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

Description
Sources: http://www.ncbi.nlm.nih.gov/pubmed/16405921
Curator's Comment: description was created based on several sources, including https://clinicaltrials.gov/ct2/show/NCT00284908?term=TENATOPRAZOLE&rank=1

Tenatoprazole, also known as TU-199 and STU-Na, is a proton pump inhibitor drug candidate that was undergoing clinical testing. The compound was invented by Mitsubishi Tanabe Pharma and was licensed to Negma Laboratories (part of Wockhardt as of 2007). Mitsubishi reported that tenatoprazole was still in Phase I clinical trials in 2007 and again in 2012. STU-Na will be used for treatment of acid related diseases (gastroduodenal ulcers, erosive or ulcerative esophagitis due to gastroesophageal reflux disease). Tenatoprazole has an imidazopyridine ring in place of the benzimidazole moiety found in other proton pump inhibitors; the binding sites of tenatoprazole were in the TM5/6 region at Cys813 and Cys822 as shown by tryptic and thermolysin digestion of the ATPase labeled by tenatoprazole. It has a half-life about seven times longer than other PPIs.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Potassium-transporting ATPase 31 Target ID: CHEMBL2095173 Sources: http://www.ncbi.nlm.nih.gov/pubmed/16405921	Inhibitor 8297

Conditions

Condition	Modality	Highest Phase	Product
Esophagitis 4 Sources: https://clinicaltrials.gov/ct2/show/NCT00284908	Primary	Phase I 428	Unknown Approved Use Unknown
Gastroesophageal reflux disease 59 Sources: https://clinicaltrials.gov/ct2/show/NCT00284908	Primary	Phase I 428	Unknown Approved Use Unknown
Stomach ulcer 15 Sources: https://clinicaltrials.gov/ct2/show/NCT00284908	Primary	Phase I 428	Unknown Approved Use Unknown
Duodenal ulcer 42 Sources: https://clinicaltrials.gov/ct2/show/NCT00284908	Primary	Phase I 428	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Tenatoprazole. Benatoprazole, TU 199.	2002	12455204
Tenatoprazole, a novel proton pump inhibitor with a prolonged plasma half-life: effects on intragastric pH and comparison with esomeprazole in healthy volunteers.	2004 Mar 15	15023167
Gateways to clinical trials.	2005 Jul-Aug	16179960
A comparative study of the early effects of tenatoprazole 40 mg and esomeprazole 40 mg on intragastric pH in healthy volunteers.	2005 Mar 1	15740541
Gateways to clinical trials.	2005 May	16082427
Effect on intragastric pH of a PPI with a prolonged plasma half-life: comparison between tenatoprazole and esomeprazole on the duration of acid suppression in healthy male volunteers.	2005 Sep	16128938
Acid suppression therapy: where do we go from here?	2006	16699262
Pharmacokinetics of tenatoprazole, a newly synthesized proton pump inhibitor, in healthy male Caucasian volunteers.	2006	16478003
Comparison of the effects of fasting morning, fasting evening and fed bedtime administration of tenatoprazole on intragastric pH in healthy volunteers: a randomized three-way crossover study.	2006 Apr 15	16611279
Review article: the opportunities and benefits of extended acid suppression.	2006 Jun	16700900
Review article: the clinical pharmacology of proton pump inhibitors.	2006 Jun	16700898
Characterization of the inhibitory activity of tenatoprazole on the gastric H+,K+ -ATPase in vitro and in vivo.	2006 Mar 14	16405921
Gateways to clinical trials.	2006 Oct	17136234
Quantification of tenatoprazole in rat plasma by HPLC: validation and its application to pharmacokinetic studies.	2007 Dec	17590865
HPLC determination and pharmacokinetic study of tenatoprazole in dog plasma after oral administration of enteric-coated capsule.	2007 Jan	17080510
A review of rabeprazole in the treatment of acid-related diseases.	2007 Jun	18488081
[Chiral separation of tenatoprazole enantiomers using high performance liquid chromatography on vacomycin-bonded chiral stationary phase].	2007 Sep	18161328
Proton pump inhibitors: do differences in pharmacokinetics translate into differences in clinical outcomes?	2008	18076214
Is the required therapeutic effect always achieved by racemic switch of proton-pump inhibitors?	2008 Apr 28	18442220
LC-UV and LC-MS evaluation of stress degradation behaviour of tenatoprazole.	2009 Dec 5	19615841
Determination of tenatoprazole enantiomers and their enantioselective pharmacokinetics in rats.	2009 Jun	18752288
Application of a stability-indicating thin-layer chromatographic method to the determination of tenatoprazole in pharmaceutical dosage forms.	2009 Mar-Apr	19485196
Novel approaches to inhibition of gastric acid secretion.	2010 Dec	20924727
The pharmacodynamics and pharmacokinetics of S-tenatoprazole-Na 30 mg, 60 mg and 90 mg vs. esomeprazole 40 mg in healthy male subjects.	2010 Mar	20015104

Patents

Sample Use Guides

In Vivo Use Guide

In the clinical trial study four dosages of S-Tenatoprazole (STU-Na) (30 mg, 60 mg, 90 mg, and 120 mg) will be tested in each volunteer. First, one of the dosages will be orally administered for five days. Then, a nine to sixteen day period without study drug administration will follow prior to the administration of the next dosage, for again five days.

Route of Administration: Oral

In Vitro Use Guide

Tenatoprazole binds at the catalytic subunit of the gastric acid pump with a stoichiometry of 2.6 nmol mg(-1) of the enzyme in vitro

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:34:34 UTC 2023` Edited by `admin` on `Fri Dec 15 15:34:34 UTC 2023`
Record UNII	RE0689TX2K
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

TENATOPRAZOLE

Official Name

English

5-METHOXY-2-(((4-METHOXY-3,5-DIMETHYL-2-PYRIDYL)METHYL)SULFINYL)-1H-IMIDAZO(4,5-B)PYRIDINE

Common Name

English

TENATOPRAZOLE [MART.]

Common Name

English

tenatoprazole [INN]

Common Name

English

1H-IMIDAZO(4,5-B)PYRIDINE, 5-METHOXY-2-(((4-METHOXY-3,5-DIMETHYL-2-PYRIDINYL)METHYL)SULFINYL)-

Common Name

English

Tenatoprazole [WHO-DD]

Common Name

English

5-METHOXY-2-(((4-METHOXY-3,5-DIMETHYL-2-PYRIDINYL)METHYL)SULFINYL)-3H-IMIDAZO(4,5-B)PYRIDINE

Common Name

English

TENATOPRAZOLE [JAN]

Common Name

English

(±)-5-METHOXY-2-(((4-METHOXY-3,5-DIMETHYL-2-PYRIDYL)METHYL)SULFINYL)-1H-IMIDAZO(4,5-B)PYRIDINE

Systematic Name

English

2-(2-((4-METHOXY-3,5-DIMETHYL-2-PYRIDINYL)METHYL)SULFINYL)-5-METHOXYIMIDAZO(4,5-B)PYRIDINE

Common Name

English

(±)-TENATOPRAZOLE

Common Name

English

3H-IMIDAZO(4,5-B)PYRIDINE, 5-METHOXY-2-(((4-METHOXY-3,5-DIMETHYL-2-PYRIDINYL)METHYL)SULFINYL)-

Systematic Name

English

TU-199

Code

English

TU199

Code

English

Classification Tree Code System Code

NCI_THESAURUS

C29723