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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
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

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

PubMed

TitleDatePubMed
Is phenylephrine pivalate a prodrug?
1980 Dec
Cytotoxicity of pivalylphenylephrine and pivalic acid to corneal endothelium.
1980 Jul
Esterase activities in adult rabbit eyes.
1983 Mar
Substance Class Chemical
Created
by admin
on Fri Dec 15 16:11:10 GMT 2023
Edited
by admin
on Fri Dec 15 16:11:10 GMT 2023
Record UNII
RB4XQ0T71U
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PIVENFRINE
INN  
INN  
Official Name English
pivenfrine [INN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C29747
Created by admin on Fri Dec 15 16:11:10 GMT 2023 , Edited by admin on Fri Dec 15 16:11:10 GMT 2023
Code System Code Type Description
SMS_ID
100000081705
Created by admin on Fri Dec 15 16:11:10 GMT 2023 , Edited by admin on Fri Dec 15 16:11:10 GMT 2023
PRIMARY
FDA UNII
RB4XQ0T71U
Created by admin on Fri Dec 15 16:11:10 GMT 2023 , Edited by admin on Fri Dec 15 16:11:10 GMT 2023
PRIMARY
ChEMBL
CHEMBL2107163
Created by admin on Fri Dec 15 16:11:10 GMT 2023 , Edited by admin on Fri Dec 15 16:11:10 GMT 2023
PRIMARY
EPA CompTox
DTXSID80867279
Created by admin on Fri Dec 15 16:11:10 GMT 2023 , Edited by admin on Fri Dec 15 16:11:10 GMT 2023
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PUBCHEM
130545
Created by admin on Fri Dec 15 16:11:10 GMT 2023 , Edited by admin on Fri Dec 15 16:11:10 GMT 2023
PRIMARY
EVMPD
SUB09950MIG
Created by admin on Fri Dec 15 16:11:10 GMT 2023 , Edited by admin on Fri Dec 15 16:11:10 GMT 2023
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NCI_THESAURUS
C66442
Created by admin on Fri Dec 15 16:11:10 GMT 2023 , Edited by admin on Fri Dec 15 16:11:10 GMT 2023
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CAS
67577-23-5
Created by admin on Fri Dec 15 16:11:10 GMT 2023 , Edited by admin on Fri Dec 15 16:11:10 GMT 2023
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INN
4630
Created by admin on Fri Dec 15 16:11:10 GMT 2023 , Edited by admin on Fri Dec 15 16:11:10 GMT 2023
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WIKIPEDIA
Pivenfrine
Created by admin on Fri Dec 15 16:11:10 GMT 2023 , Edited by admin on Fri Dec 15 16:11:10 GMT 2023
PRIMARY
Related Record Type Details
ACTIVE MOIETY