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Merck
CN

SML1441

Tenatoprazole

≥98% (HPLC)

Synonym(s):

(RS)-3-Methoxy-8-[(4-methoxy-3,5-dimethyl-pyridin-2-yl)methylsulfinyl]-2,7,9-triazabicyclo[4.3.0]nona-2,4,8,10-tetraene

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About This Item

Empirical Formula (Hill Notation):
C16H18N4O3S
CAS Number:
113712-98-4
Molecular Weight:
346.40
NACRES:
NA.77
PubChem Substance ID:
329825881
UNSPSC Code:
12352200
MDL number:
MFCD00929085

Key Documents

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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)

SMILES string

CC1=C(OC)C(C)=CN=C1CS(C2=NC3=NC(OC)=CC=C3N2)=O

InChI key

ZBFDAUIVDSSISP-UHFFFAOYSA-N

assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 5 mg/mL, clear (warmed)

storage temp.

2-8°C

Quality Level

100

Related Categories

General description

Tenatoprazole is a novel proton pump inhibitor with an imidazopyridine backbone. It has seven-fold longer plasma half-life. It is also called as 5-methoxy-2-(4-methoxy-3,5-dimethyl-pyridin-2-ylmethanesulfinyl)-1H-imidazo[4,5-b]pyridine.Tenatoprazole is a member of the class of covalent proton pump inhibitors.

Biochem/physiol Actions

Tenatoprazole is a proton pump inhibitor.
Tenatoprazole is a proton pump inhibitor. Tenatoprazole is an acid-activated prodrug that binds covalently to gastric H,K-ATPase, resulting in acid secretion inhibition. Tenatoprazole has a different structural class from omeprazole and most other proton pump inhibitors, with an imidazopyridine backbone rather than benzimidazole, which results in slower metabolism. Tenatoprazole thus has a long plasma half-life as compared to omeprazole, resulting in prolonged inhibition of acid secretion.
Tenatoprazole is used to maintain high diurnal and nocturnal pH levels. It prevents gastric H+,K+-ATPase with potency similar to omeprazole.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
0000024767
0000024766
095M4748V

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Jai Moo Shin et al.
Biochemical pharmacology, 71(6), 837-849 (2006-01-13)
Tenatoprazole is a prodrug of the proton pump inhibitor (PPI) class, which is converted to the active sulfenamide or sulfenic acid by acid in the secretory canaliculus of the stimulated parietal cell of the stomach. This active species binds to
Tenatoprazole, a novel proton pump inhibitor with a prolonged plasma half?life: effects on intragastric pH and comparison with esomeprazole in healthy volunteers.
Galmiche J P, et al.
Alimentary Pharmacology & Therapeutics, 19(6), 655-662 (2004)
Anthony R Guastella et al.
Journal of neuro-oncology, 139(2), 239-249 (2018-04-19)
There is mounting evidence supporting the role of tryptophan metabolism via the kynurenine pathway (KP) in the pathogenesis of primary brain tumors. Under normal physiological conditions, the KP is the major catabolic pathway for the essential amino acid tryptophan. However

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