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Details

Stereochemistry RACEMIC
Molecular Formula C14H21NO3
Molecular Weight 251.3214
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PIVENFRINE

SMILES

CNCC(O)C1=CC(OC(=O)C(C)(C)C)=CC=C1

InChI

InChIKey=DQCAWJLMFJKICG-UHFFFAOYSA-N
InChI=1S/C14H21NO3/c1-14(2,3)13(17)18-11-7-5-6-10(8-11)12(16)9-15-4/h5-8,12,15-16H,9H2,1-4H3

HIDE SMILES / InChI

Molecular Formula C14H21NO3
Molecular Weight 251.3214
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Description

Pivenfrine is a sympathomimetic agent. Pivenfrine is an analog of phenylephrine hydrochloride (PE) ten times more potent as a mydriatic. It is a product of the esterification of a molecule of pivalic acid (PA) to the p-hydroxyl group of PE. It is, therefore, more lipophilic than PE is, and penetrates the cornea more readily. Pivenfrine is called a prodrug of PE because it is enzymatically hydrolyzed to the active, parent compound (PE), and to PA, before reaching its desired active site in the eye. The pivenfrine-treated corneas without epithelium significantly increased in thickness, whereas no change in thickness was observed in corneas with epithelium intact.

Approval Year

PubMed

Substance Class Chemical
Record UNII
RB4XQ0T71U
Record Status Validated (UNII)
Record Version