CHEBI:4646 - dipivefrin

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ChEBI Name dipivefrin
ChEBI ID CHEBI:4646
Definition The dipivalate ester of (±)-epinephrine (racepinephrine). A pro-drug of epinephrine, the hydrochloride is used topically as eye drops to reduce intra-ocular pressure in the treatment of open-angle glaucoma or ocular hypertension.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C19H29NO5
Net Charge 0
Average Mass 351.43730
Monoisotopic Mass 351.205
InChI InChI=1S/C19H29NO5/c1-18(2,3)16(22)24-14-9-8-12(13(21)11-20-7)10-15(14)25-17(23)19(4,5)6/h8-10,13,20-21H,11H2,1-7H3
InChIKey OCUJLLGVOUDECM-UHFFFAOYSA-N
SMILES CNCC(O)c1ccc(OC(=O)C(C)(C)C)c(OC(=O)C(C)(C)C)c1
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Biological Role(s): adrenergic agonist
An agent that selectively binds to and activates adrenergic receptors.
sympathomimetic agent
A drug that mimics the effects of stimulating postganglionic adrenergic sympathetic nerves. Included in this class are drugs that directly stimulate adrenergic receptors and drugs that act indirectly by provoking the release of adrenergic transmitters.
Application(s): prodrug
A compound that, on administration, must undergo chemical conversion by metabolic processes before becoming the pharmacologically active drug for which it is a prodrug.
adrenergic agonist
An agent that selectively binds to and activates adrenergic receptors.
sympathomimetic agent
A drug that mimics the effects of stimulating postganglionic adrenergic sympathetic nerves. Included in this class are drugs that directly stimulate adrenergic receptors and drugs that act indirectly by provoking the release of adrenergic transmitters.
antiglaucoma drug
Any drug which can be used to prevent or alleviate glaucoma, a disease in which the optic nerve is damaged, resulting in progressive, irreversible loss of vision. It is often, though not always, associated with increased pressure of the fluid in the eye.
ophthalmology drug
Any compound used for the treatment of eye conditions or eye diseases.
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ChEBI Ontology
Outgoing dipivefrin (CHEBI:4646) has functional parent adrenaline (CHEBI:33568)
dipivefrin (CHEBI:4646) has role adrenergic agonist (CHEBI:37886)
dipivefrin (CHEBI:4646) has role antiglaucoma drug (CHEBI:39456)
dipivefrin (CHEBI:4646) has role ophthalmology drug (CHEBI:66981)
dipivefrin (CHEBI:4646) has role prodrug (CHEBI:50266)
dipivefrin (CHEBI:4646) has role sympathomimetic agent (CHEBI:35524)
dipivefrin (CHEBI:4646) is a ethanolamines (CHEBI:23981)
dipivefrin (CHEBI:4646) is a pivalate ester (CHEBI:50784)
dipivefrin (CHEBI:4646) is conjugate base of dipivefrin(1+) (CHEBI:73714)
Incoming dipivefrin(1+) (CHEBI:73714) is conjugate acid of dipivefrin (CHEBI:4646)
IUPAC Name
4-[1-hydroxy-2-(methylamino)ethyl]benzene-1,2-diyl bis(2,2-dimethylpropanoate)
INNs Sources
dipivefrina ChemIDplus
dipivéfrine WHO MedNet
dipivefrine ChEBI
dipivefrinum ChemIDplus
Synonyms Sources
(±)-4-[1-hydroxy-2-(methylamino)ethyl]-o-phenylene divavalate ChEBI
1-(3',4'-dipivaloyloxyphenyl)-2-methylamino-1-ethanol ChEBI
4-[1-hydroxy-2-(methylamino)ethyl]-o-phenylene divavalate ChEBI
dipivalyl epinephrine ChEBI
Dipivefrin KEGG COMPOUND
Dipivefrine KEGG COMPOUND
Manual Xrefs Databases
922 DrugCentral
C06963 KEGG COMPOUND
D02349 KEGG DRUG
DB00449 DrugBank
DE2152058 Patent
DE2343657 Patent
Dipivefrin Wikipedia
LSM-1583 LINCS
US3809714 Patent
US4085270 Patent
View more database links
Registry Numbers Types Sources
2165183 Beilstein Registry Number Beilstein
52365-63-6 CAS Registry Number KEGG COMPOUND
52365-63-6 CAS Registry Number ChemIDplus
Last Modified
22 February 2017