CHEBI:4646 - dipivefrin

ChEBI IDCHEBI:4646
ChEBI Namedipivefrin
Stars
DefinitionThe 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.
Last Modified22 February 2017
DownloadsMolfile
FormulaC19H29NO5
Net Charge0
Average Mass351.443
Monoisotopic Mass351.20457
SMILESCNCC(O)c1ccc(OC(=O)C(C)(C)C)c(OC(=O)C(C)(C)C)c1
InChIInChI=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
InChIKeyOCUJLLGVOUDECM-UHFFFAOYSA-N
Wikipedia
Roles Classification
Chemical Role:
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Biological Roles:
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.
adrenergic agonist  An agent that selectively binds to and activates adrenergic receptors.
Applications:
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.
ophthalmology drug  Any compound used for the treatment of eye conditions or eye diseases.
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.
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.
ChEBI Ontology
Outgoing Relation(s)
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 Relation(s)
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  Source
dipivefrineChEBI
dipivefrinaChemIDplus
dipivefrinumChemIDplus
dipivéfrineWHO MedNet
Synonyms  Source
DipivefrinKEGG COMPOUND
DipivefrineKEGG COMPOUND
dipivalyl epinephrineChEBI
(±)-4-[1-hydroxy-2-(methylamino)ethyl]-o-phenylene divavalateChEBI
4-[1-hydroxy-2-(methylamino)ethyl]-o-phenylene divavalateChEBI
1-(3',4'-dipivaloyloxyphenyl)-2-methylamino-1-ethanolChEBI
Manual XrefsDatabases
C06963KEGG COMPOUND
D02349KEGG DRUG
DE2152058Patent
US4085270Patent
DE2343657Patent
US3809714Patent
DB00449DrugBank
DipivefrinWikipedia
LSM-1583LINCS
922DrugCentral
Registry NumbersSources
Beilstein:2165183Beilstein
CAS:52365-63-6KEGG COMPOUND
CAS:52365-63-6ChemIDplus