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SML1441

Sigma-Aldrich

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
MDL number:
MFCD00929085
UNSPSC Code:
12352200
PubChem Substance ID:
329825881
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 5 mg/mL, clear (warmed)

storage temp.

2-8°C

SMILES string

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

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)

InChI key

ZBFDAUIVDSSISP-UHFFFAOYSA-N

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 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

Signal Word

Warning

Hazard Statements

H302,H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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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