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 38 Target ID: CHEMBL2095173 Sources: http://www.ncbi.nlm.nih.gov/pubmed/16405921	Inhibitor 8504

Conditions

Condition	Modality	Highest Phase	Product
Esophagitis 4 Sources: https://clinicaltrials.gov/ct2/show/NCT00284908	Primary	Phase I 438	Unknown Approved Use Unknown
Gastroesophageal reflux disease 68 Sources: https://clinicaltrials.gov/ct2/show/NCT00284908	Primary	Phase I 438	Unknown Approved Use Unknown
Stomach ulcer 17 Sources: https://clinicaltrials.gov/ct2/show/NCT00284908	Primary	Phase I 438	Unknown Approved Use Unknown
Duodenal ulcer 49 Sources: https://clinicaltrials.gov/ct2/show/NCT00284908	Primary	Phase I 438	Unknown Approved Use Unknown

C_max

Value	Dose	Analyte	Population
1284 ng/mL EXPERIMENT https://www.sciencedirect.com/science/article/pii/S0016508503811599	10 mg 1 times / day steady-state, oral dose: 10 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	TENATOPRAZOLE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
2990 ng/mL EXPERIMENT https://www.sciencedirect.com/science/article/pii/S0016508503811599	20 mg 1 times / day steady-state, oral dose: 20 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	TENATOPRAZOLE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
5494 ng/mL EXPERIMENT https://www.sciencedirect.com/science/article/pii/S0016508503811599	40 mg 1 times / day steady-state, oral dose: 40 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	TENATOPRAZOLE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
11819 ng/mL EXPERIMENT https://www.sciencedirect.com/science/article/pii/S0016508503811599	80 mg 1 times / day steady-state, oral dose: 80 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	TENATOPRAZOLE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
3570.7 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/20015104/	30 mg 1 times / day multiple, oral dose: 30 mg route of administration: Oral experiment type: MULTIPLE co-administered:	TENATOPRAZOLE, (S)- plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
7206.71 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/20015104/	60 mg 1 times / day multiple, oral dose: 60 mg route of administration: Oral experiment type: MULTIPLE co-administered:	TENATOPRAZOLE, (S)- plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
11475.3 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/20015104/	90 mg 1 times / day multiple, oral dose: 90 mg route of administration: Oral experiment type: MULTIPLE co-administered:	TENATOPRAZOLE, (S)- plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

AUC

Value	Dose	Analyte	Population
12675 ng × h/mL EXPERIMENT https://www.sciencedirect.com/science/article/pii/S0016508503811599	10 mg 1 times / day steady-state, oral dose: 10 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	TENATOPRAZOLE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
35910 ng × h/mL EXPERIMENT https://www.sciencedirect.com/science/article/pii/S0016508503811599	20 mg 1 times / day steady-state, oral dose: 20 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	TENATOPRAZOLE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
75240 ng × h/mL EXPERIMENT https://www.sciencedirect.com/science/article/pii/S0016508503811599	40 mg 1 times / day steady-state, oral dose: 40 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	TENATOPRAZOLE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
218372 ng × h/mL EXPERIMENT https://www.sciencedirect.com/science/article/pii/S0016508503811599	80 mg 1 times / day steady-state, oral dose: 80 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	TENATOPRAZOLE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
44716 mg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/20015104/	30 mg 1 times / day multiple, oral dose: 30 mg route of administration: Oral experiment type: MULTIPLE co-administered:	TENATOPRAZOLE, (S)- plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
105391 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/20015104/	60 mg 1 times / day multiple, oral dose: 60 mg route of administration: Oral experiment type: MULTIPLE co-administered:	TENATOPRAZOLE, (S)- plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
157431 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/20015104/	90 mg 1 times / day multiple, oral dose: 90 mg route of administration: Oral experiment type: MULTIPLE co-administered:	TENATOPRAZOLE, (S)- plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

T_1/2

Value	Dose	Analyte	Population
5.2 h EXPERIMENT https://www.sciencedirect.com/science/article/pii/S0016508503811599	10 mg 1 times / day steady-state, oral dose: 10 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	TENATOPRAZOLE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
7.8 h EXPERIMENT https://www.sciencedirect.com/science/article/pii/S0016508503811599	20 mg 1 times / day steady-state, oral dose: 20 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	TENATOPRAZOLE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
8.7 h EXPERIMENT https://www.sciencedirect.com/science/article/pii/S0016508503811599	40 mg 1 times / day steady-state, oral dose: 40 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	TENATOPRAZOLE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
9.2 h EXPERIMENT https://www.sciencedirect.com/science/article/pii/S0016508503811599	80 mg 1 times / day steady-state, oral dose: 80 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	TENATOPRAZOLE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
8.21 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/20015104/	30 mg 1 times / day multiple, oral dose: 30 mg route of administration: Oral experiment type: MULTIPLE co-administered:	TENATOPRAZOLE, (S)- plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
8.7 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/20015104/	60 mg 1 times / day multiple, oral dose: 60 mg route of administration: Oral experiment type: MULTIPLE co-administered:	TENATOPRAZOLE, (S)- plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
9.01 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/20015104/	90 mg 1 times / day multiple, oral dose: 90 mg route of administration: Oral experiment type: MULTIPLE co-administered:	TENATOPRAZOLE, (S)- plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

Doses

Dose	Population	Adverse events
90 mg 1 times / day multiple, oral Highest studied dose Dose: 90 mg, 1 times / day Route: oral Route: multiple Dose: 90 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/20015104/	healthy, ADULT Health Status: healthy Age Group: ADULT Sex: M Food Status: FASTED Sources: https://pubmed.ncbi.nlm.nih.gov/20015104/	Other AEs: Gastrin increased... Other AEs: Gastrin increased (3.2%) Sources: https://pubmed.ncbi.nlm.nih.gov/20015104/

AEs

AE	Significance	Dose	Population
Gastrin increased	3.2%	90 mg 1 times / day multiple, oral Highest studied dose Dose: 90 mg, 1 times / day Route: oral Route: multiple Dose: 90 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/20015104/	healthy, ADULT Health Status: healthy Age Group: ADULT Sex: M Food Status: FASTED Sources: https://pubmed.ncbi.nlm.nih.gov/20015104/

PubMed

Title	Date	PubMed
Novel approaches to inhibition of gastric acid secretion.	2010-12	20924727
The pharmacodynamics and pharmacokinetics of S-tenatoprazole-Na 30 mg, 60 mg and 90 mg vs. esomeprazole 40 mg in healthy male subjects.	2010-03	20015104
LC-UV and LC-MS evaluation of stress degradation behaviour of tenatoprazole.	2009-12-05	19615841
Application of a stability-indicating thin-layer chromatographic method to the determination of tenatoprazole in pharmaceutical dosage forms.	2009-06-03	19485196
Determination of tenatoprazole enantiomers and their enantioselective pharmacokinetics in rats.	2009-06	18752288
Is the required therapeutic effect always achieved by racemic switch of proton-pump inhibitors?	2008-04-28	18442220
Proton pump inhibitors: do differences in pharmacokinetics translate into differences in clinical outcomes?	2008	18076214
Quantification of tenatoprazole in rat plasma by HPLC: validation and its application to pharmacokinetic studies.	2007-12	17590865
[Chiral separation of tenatoprazole enantiomers using high performance liquid chromatography on vacomycin-bonded chiral stationary phase].	2007-09	18161328
A review of rabeprazole in the treatment of acid-related diseases.	2007-06	18488081
HPLC determination and pharmacokinetic study of tenatoprazole in dog plasma after oral administration of enteric-coated capsule.	2007-01	17080510
Gateways to clinical trials.	2006-10	17136234
Review article: the opportunities and benefits of extended acid suppression.	2006-06	16700900
Review article: the clinical pharmacology of proton pump inhibitors.	2006-06	16700898
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.	2006-04-15	16611279
Characterization of the inhibitory activity of tenatoprazole on the gastric H+,K+ -ATPase in vitro and in vivo.	2006-03-14	16405921
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
Gateways to clinical trials.	2005-09-24	16179960
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.	2005-09	16128938
Gateways to clinical trials.	2005-05	16082427
A comparative study of the early effects of tenatoprazole 40 mg and esomeprazole 40 mg on intragastric pH in healthy volunteers.	2005-03-01	15740541
Tenatoprazole, a novel proton pump inhibitor with a prolonged plasma half-life: effects on intragastric pH and comparison with esomeprazole in healthy volunteers.	2004-03-15	15023167
Tenatoprazole. Benatoprazole, TU 199.	2002	12455204

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 `Mon Mar 31 18:01:40 GMT 2025` Edited by `admin` on `Mon Mar 31 18:01:40 GMT 2025`
Record UNII	RE0689TX2K
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

TENATOPRAZOLE

Official Name

English

TU-199

Preferred 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

TU199

Code

English

Classification Tree Code System Code

NCI_THESAURUS

C29723