Hydrolysis of thecis-Phenyl Ester of Thymidine 3‘,5‘-Cyclic Monophosphate:  pH-Dependent Competition between Depyrimidination and Phosphotriester HydrolysisviaCO and PO Bond Ruptures

1997 ◽  
Vol 62 (4) ◽  
pp. 893-898 ◽  
Author(s):  
Jaana Varila ◽  
Teemu Hankamäki ◽  
Mikko Oivanen ◽  
Leo H. Koole ◽  
Harri Lönnberg
Keyword(s):  
Phenyl Ester ◽  
Cyclic Monophosphate ◽  
Ph Dependent ◽  
Hydrolysis Of

Hydrolysis and methanolysis of the phenyl ester of thymidine 3',5'-cyclic monophosphate: pH-dependent competition between PO and CO bond ruptures

1996 ◽  
Vol 61 (s1) ◽  
pp. 26-29
Author(s):  
Mikko Oivanen ◽  
Jaana Varila ◽  
Teemu Hankamaki ◽  
Leo H. Koole ◽  
Harri Lönnberg
Keyword(s):  
Phenyl Ester ◽  
Cyclic Monophosphate ◽  
Ph Dependent

Polymer Effects under Pressure. 2. Enzymelike Catalysis in the Hydrolysis of Phenyl Ester by Copolymer Containing Imidazole

1978 ◽  
Vol 11 (4) ◽  
pp. 829-832 ◽  
Author(s):  
Yoshihiro Taniguchi ◽  
Kiyokazu Shimokawa ◽  
Hideo Hisatome ◽  
Shyoichi Tanamachi ◽  
Keizo Suzuki
Keyword(s):  
Phenyl Ester ◽  
Hydrolysis Of

Modeling the pH dependent hydrolysis of VX for aqueous releases

2009 ◽  
Vol 170 (1) ◽  
pp. 72-78 ◽  
Author(s):  
J.A. Cragan ◽  
M.C. Ward ◽  
C.B. Mueller
Keyword(s):  
Ph Dependent ◽  
Hydrolysis Of

pH-dependent hydrolysis of acetylcholine: Consequences for non-neuronal acetylcholine

2015 ◽  
Vol 29 (1) ◽  
pp. 27-30 ◽  
Author(s):  
Ignaz Wessler ◽  
Rosmarie Michel-Schmidt ◽  
Charles James Kirkpatrick
Keyword(s):  
Ph Dependent ◽  
Hydrolysis Of

QSAR analysis of chemical and serum-catalyzed hydrolysis of phenyl ester prodrugs of nipecotic acid

1988 ◽  
Vol 48 (1-3) ◽  
pp. 91-102 ◽  
Author(s):  
C ALTOMARE ◽  
A CAROTTI ◽  
S CELLAMARE ◽  
M FERAPPI ◽  
R CAGIANO ◽  
...  
Keyword(s):  
Phenyl Ester ◽  
Nipecotic Acid ◽  
Qsar Analysis ◽  
Hydrolysis Of ◽  
Ester Prodrugs

scholarly journals pH-dependent spontaneous hydrolysis rather than gut bacterial metabolism reduces levels of the ADHD treatment, Methylphenidate

2020 ◽  
Author(s):  
Julia Aresti-Sanz ◽  
Walid Maho ◽  
Rob Rodrigues Pereira ◽  
Hjalmar Permentier ◽  
Sahar El Aidy
Keyword(s):  
Intestinal Bacteria ◽  
Bacterial Metabolism ◽  
Spontaneous Hydrolysis ◽  
Adhd Treatment ◽  
High Interindividual Variability ◽  
Carboxylesterase 1 ◽  
Ph Dependent ◽  
Small Intestinal ◽  
Hydrolysis Of

AbstractMethylphenidate is absorbed in the small intestine. The drug is known to have low bioavailability and a high interindividual variability in terms of response to the treatment. Gut microbiota has been shown to reduce the bioavailability of a wide variety of orally administered drugs. Here, we tested the ability of small intestinal bacteria to metabolize methylphenidate. In silico analysis identified several small intestinal bacteria to harbor homologues of the human carboxylesterase 1 enzyme responsible for the hydrolysis of methylphenidate in the liver. Despite our initial results hinting towards possible bacterial hydrolysis of the drug, up to 60% of methylphenidate was spontaneously hydrolyzed in the absence of bacteria and this hydrolysis was pH-dependent. Overall, the study shows that pH-dependent spontaneous hydrolysis rather than gut bacterial metabolism reduces levels of methylphenidate and suggest a role of the luminal pH in the bioavailability of the drug.

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