CHEBI:681848 - doxapram

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ChEBI Name doxapram
ChEBI ID CHEBI:681848
Definition A member of the class of pyrrolidin-2-ones that is N-ethylpyrrolidin-2-one in which both of the hydrogens at the 3 position (adjacent to the carbonyl group) are substituted by phenyl groups, and one of the hydrogens at the 4 position is substituted by a 2-(morpholin-4-yl)ethyl group. A central and respiratory stimulant with a brief duration of action, it is used (generally as the hydrochloride or the hydrochloride hydrate) as a temporary treatment of acute respiratory failure, particularly when superimposed on chronic obstructive pulmonary disease, and of postoperative respiratory depression. It has also been used for treatment of postoperative shivering.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C24H30N2O2
Net Charge 0
Average Mass 378.50720
Monoisotopic Mass 378.231
InChI InChI=1S/C24H30N2O2/c1-2-26-19-22(13-14-25-15-17-28-18-16-25)24(23(26)27,20-9-5-3-6-10-20)21-11-7-4-8-12-21/h3-12,22H,2,13-19H2,1H3
InChIKey XFDJYSQDBULQSI-UHFFFAOYSA-N
SMILES CCN1CC(CCN2CCOCC2)C(C1=O)(c1ccccc1)c1ccccc1
Roles Classification
Application(s): central nervous system stimulant
Any drug that enhances the activity of the central nervous system.
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ChEBI Ontology
Outgoing doxapram (CHEBI:681848) has role central nervous system stimulant (CHEBI:35337)
doxapram (CHEBI:681848) is a morpholines (CHEBI:38785)
doxapram (CHEBI:681848) is a pyrrolidin-2-ones (CHEBI:74223)
Incoming doxapram hydrochloride (anhydrous) (CHEBI:59837) has part doxapram (CHEBI:681848)
(R)-doxapram (CHEBI:59842) is a doxapram (CHEBI:681848)
(S)-doxapram (CHEBI:59843) is a doxapram (CHEBI:681848)
IUPAC Name
1-ethyl-4-[2-(morpholin-4-yl)ethyl]-3,3-diphenylpyrrolidin-2-one
INNs Sources
doxapram WHO MedNet
doxapram WHO MedNet
doxapram KEGG DRUG
Synonyms Sources
(±)-doxapram ChEBI
1-ethyl-4-(2-morpholinoethyl)-3,3-diphenyl-2-pyrrolidinone ChemIDplus
Doxapram ChEMBL
Database Links Databases
953 DrugCentral
BE613734 Patent
D07873 KEGG DRUG
DB00561 DrugBank
Doxapram Wikipedia
LSM-5058 LINCS
US3192206 Patent
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Registry Numbers Types Sources
309-29-5 CAS Registry Number KEGG DRUG
309-29-5 CAS Registry Number ChemIDplus
628691 Reaxys Registry Number Reaxys
628691 Beilstein Registry Number Beilstein
Citations Waiting for Citations Types Sources
19663568 PubMed citation Europe PMC
20140700 PubMed citation Europe PMC
25819170 PubMed citation Europe PMC
26896538 PubMed citation Europe PMC
4122029 PubMed citation Europe PMC
4126096 PubMed citation Europe PMC
527638 PubMed citation Europe PMC
Last Modified
22 February 2017