DOXAPRAM

Details

Stereochemistry	RACEMIC
Molecular Formula	C24H30N2O2
Molecular Weight	378.5072
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCN1CC(CCN2CCOCC2)C(C1=O)(C3=CC=CC=C3)C4=CC=CC=C4

InChI

InChIKey=XFDJYSQDBULQSI-UHFFFAOYSA-N

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

HIDE SMILES / InChI

Molecular Formula	C24H30N2O2
Molecular Weight	378.5072
Charge	0
Count

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

Description
Sources: http://www.drugbank.ca/drugs/DB00561
Curator's Comment: Description was created based on several sources, including http://www.accessdata.fda.gov/drugsatfda_docs/label/2005/14879s044lbl.pdf

Doxapram is an analeptic agent (a stimulant of the central nervous system). The respiratory stimulant action is manifested by an increase in tidal volume associated with a slight increase in respiratory rate. A pressor response may result following doxapram administration. Provided there is no impairment of cardiac function, the pressor effect is more marked in hypovolemic than in normovolemic states. The pressor response is due to the improved cardiac output rather than peripheral vasoconstriction. Following doxapram administration, an increased release of catecholamines has been noted. Doxapram produces respiratory stimulation mediated through the peripheral carotid chemoreceptors. It is thought to stimulate the carotid body by inhibiting certain potassium channels. Used as temporary measure in hospitalized patients with acute respiratory insufficiency superimposed on chronic obstructive pulmonary disease.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Potassium channel subfamily K member 3 10 Target ID: CHEMBL2321613 Sources: http://www.drugbank.ca/drugs/DB00561	Inhibitor 8504
Potassium channel subfamily K member 9 6 Target ID: CHEMBL2321614 Sources: http://www.drugbank.ca/drugs/DB00561	Inhibitor 8504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Drug-induced postanesthesia respiratory depression 3 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2005/14879s044lbl.pdf	Secondary		Approved 8583	Doxapram Approved Use Postanesthesia a. When the possibility of airway obstruction and/or hypoxia have been eliminated, doxapram may be used to stimulate respiration in patients with drug-induced postanesthesia respiratory depression or apnea other than that due to muscle relaxant drugs. b. To pharmacologically stimulate deep breathing in the postoperative patient. Drug-Induced Central Nervous System Depression Exercising care to prevent vomiting and aspiration, doxapram may be used to stimulate respiration, hasten arousal, and to encourage the return of laryngopharyngeal reflexes in patients with mild to moderate respiratory and CNS depression due to drug overdosage. Chronic Pulmonary Disease Associated with Acute Hypercapnia Doxapram is indicated as a temporary measure in hospitalized patients with acute respiratory insufficiency superimposed on chronic obstructive pulmonary disease. Launch Date 1965
Chronic pulmonary disease associated with acute hypercapnia 3 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2005/14879s044lbl.pdf	Primary		Approved 8583	Doxapram Approved Use Postanesthesia a. When the possibility of airway obstruction and/or hypoxia have been eliminated, doxapram may be used to stimulate respiration in patients with drug-induced postanesthesia respiratory depression or apnea other than that due to muscle relaxant drugs. b. To pharmacologically stimulate deep breathing in the postoperative patient. Drug-Induced Central Nervous System Depression Exercising care to prevent vomiting and aspiration, doxapram may be used to stimulate respiration, hasten arousal, and to encourage the return of laryngopharyngeal reflexes in patients with mild to moderate respiratory and CNS depression due to drug overdosage. Chronic Pulmonary Disease Associated with Acute Hypercapnia Doxapram is indicated as a temporary measure in hospitalized patients with acute respiratory insufficiency superimposed on chronic obstructive pulmonary disease. Launch Date 1965

C_max

Value	Dose	Co-administered	Analyte	Population
0.96 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/32901	300 mg single, oral dose: 300 mg route of administration: Oral experiment type: SINGLE co-administered:		DOXAPRAM plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

AUC

Value	Dose	Co-administered	Analyte	Population
272 μg × min/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/32901	1.5 mg/kg single, intravenous dose: 1.5 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered:		DOXAPRAM plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
596 μg × min/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/32901	300 mg single, oral dose: 300 mg route of administration: Oral experiment type: SINGLE co-administered:		DOXAPRAM plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

T_1/2

Value	Dose	Co-administered	Analyte	Population
3.4 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/32901	1.5 mg/kg single, intravenous dose: 1.5 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered:		DOXAPRAM plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
7.5 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/32901	300 mg single, oral dose: 300 mg route of administration: Oral experiment type: SINGLE co-administered:		DOXAPRAM plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

Doses

Dose	Population	Adverse events
3 mg/kg single, intravenous Studied dose Dose: 3 mg/kg Route: intravenous Route: single Dose: 3 mg/kg Sources: https://pubmed.ncbi.nlm.nih.gov/3371147	unhealthy, infants Health Status: unhealthy Age Group: infants Sources: https://pubmed.ncbi.nlm.nih.gov/3371147	Sources: https://pubmed.ncbi.nlm.nih.gov/3371147

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1946

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	CYP1A2 1197 CYP2A6 626 CYP2B6 776 CYP2C8 810 CYP2C19 1119 CYP2E1 729 CYP3A5 446 CYP3A7 109

Drug as victim

Target	Modality	Activity
CYP2C19 1119	substrate 4014 Sources: https://link.springer.com/article/10.1007/s00431-014-2416-1 Page: 8.0	negligible
CYP3A7 109	substrate 4014 Sources: https://link.springer.com/article/10.1007/s00431-014-2416-1 Page: 8.0	negligible
CYP1A2 1197	substrate 4014 Sources: https://link.springer.com/article/10.1007/s00431-014-2416-1 Page: 8.0	no
CYP2A6 626	substrate 4014 Sources: https://link.springer.com/article/10.1007/s00431-014-2416-1 Page: 8.0	no
CYP2B6 776	substrate 4014 Sources: https://link.springer.com/article/10.1007/s00431-014-2416-1 Page: 8.0	no
CYP2C8 810	substrate 4014 Sources: https://link.springer.com/article/10.1007/s00431-014-2416-1 Page: 8.0	no
CYP2E1 729	substrate 4014 Sources: https://link.springer.com/article/10.1007/s00431-014-2416-1 Page: 8.0	no
CYP3A4 1946	substrate 4014 Sources: https://link.springer.com/article/10.1007/s00431-014-2416-1 Page: 8.0	yes
CYP3A5 446	substrate 4014 Sources: https://link.springer.com/article/10.1007/s00431-014-2416-1 Page: 8.0	yes

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:681848	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:681848
ChemicalBook	CB4245654	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB4245654
eMolecules	901795	https://www.emolecules.com/cgi-bin/more?vid=901795
MolPort	MolPort-005-933-844	https://www.molport.com/shop/molecule-link/MolPort-005-933-844

PubMed

Title	Date	PubMed
Intrathecal meperidine reduces intraoperative shivering during transurethral prostatectomy in elderly patients.	2010-12	21253375
The clinical practice of CPCR in small animals: an internet-based survey.	2010-12	21166977
Emergence agitation in adults: risk factors in 2,000 patients.	2010-09	20526708
Chronic hypoxia increases the gain of the hypoxic ventilatory response by a mechanism in the central nervous system.	2010-08	20489036
Glial cells are involved in the exciting effects of doxapram on brainstem slices in vitro.	2010-07	20140700
Comparative study on effectiveness of doxapram and pethidine for postanaesthetic shivering.	2010-04-15	20387350
Effects of serotonin agonists and doxapram on respiratory depression and hypoxemia in etorphine-immobilized impala (Aepyceros melampus).	2010-04	20688644
Respiratory and cardiovascular effects of doxapram and theophylline for the treatment of asphyxia in neonatal calves.	2010-03-15	20022095
Evaluation of respiratory function in freely moving Beagle dogs using implanted impedance technology.	2010-03-03	20601021
Chemical immobilization of Weddell seals (Leptonychotes weddellii) by ketamine/midazolam combination.	2010-03	20230562
[Effect of doxapram on the respiratory rhythmical discharge activity in the brainstem slice of neonatal rats].	2010-02	20159691
Respiratory inductive plethysmography as a method for measuring ventilatory parameters in conscious, non-restrained dogs.	2010-01-26	20435149
Surfactant without intubation in preterm infants with respiratory distress: first multi-center data.	2010-01-20	20084586
Transdermal buprenorphine - a critical appraisal of its role in pain management.	2009-09-15	21197300
Management and prevention of chronic obstructive pulmonary disease exacerbations: a state of the art review.	2009-08-07	19664218
Doxapram revisited in patients with cancer.	2009-08	19663568
Decreased neurokinin-1 (substance P) receptor binding in patients with panic disorder: positron emission tomographic study with [18F]SPA-RQ.	2009-07-01	19200949
Prophylactic granisetron vs pethidine for the prevention of postoperative shivering: a randomized control trial.	2009-06	20640142
Presumptive benzocaine-induced methemoglobinemia in a slender-tailed meerkat (Suricata suricatta).	2009-06	19569494
Neuroimaging in anxiety disorders.	2009-06	18568288
[Recommended treatment of apnea in premature infants. A review based on literature and own experience].	2009-05-28	19471054
Managing acute on chronic respiratory failure: a guide to non-invasive ventilation.	2008-08	18783091
Acid-sensitive channel inhibition prevents fetal alcohol spectrum disorders cerebellar Purkinje cell loss.	2008-08	18509098
Difficult extubation in low birthweight infants.	2008-05	18006566
Retrospective comparison of caffeine and doxapram for the treatment of hypercapnia in foals with hypoxic-ischemic encephalopathy.	2008-03-29	18371030
Respiratory irregularity and stress hormones in panic disorder: exploring potential linkages.	2008	17557312
Comparison of the effects of caffeine and doxapram on respiratory and cardiovascular function in foals with induced respiratory acidosis.	2007-12	18052748
The effect of doxapram on brain imaging in patients with panic disorder.	2007-10	17560768
[Sensory stimulations for the treatment of idiopathic apneas of prematurity].	2007-05	17320360
Creatine supplementation attenuates corticosteroid-induced muscle wasting and impairment of exercise performance in rats.	2007-02	17053101
A new look at the respiratory stimulant doxapram.	2007-01-18	17227289
Dynamic QT/RR relationship of cardiac conduction in premature infants treated with low-dose doxapram hydrochloride.	2007	17614751
HPA axis activity in patients with panic disorder: review and synthesis of four studies.	2007	16845643
European Academy of Paediatrics, Barcelona, Spain, October 7-10, 2006. Abstracts.	2006-11	17242961
Doxapram and aminophylline on bispectral index under sevoflurane anaesthesia: a comparative study.	2006-11	16895622
[Determination of methamphetamine in whole blood by capillary zone electrophoresis after solid phase extraction].	2006-10-15	17190148
[Analysis of 37 drugs in whole blood by HPLC after solid phase extraction].	2006-10-15	17190147
[Clinical observation of target-controlled remifentanil infusion combined with propofol and doxapram in painless artificial abortion].	2006-08	16939923
Frequency of apnea, bradycardia, and desaturations following first diphtheria-tetanus-pertussis-inactivated polio-Haemophilus influenzae type B immunization in hospitalized preterm infants.	2006-06-19	16784533
Doxapram shortens recovery following sevoflurane anesthesia.	2006-05	16636029
The ventilatory stimulant doxapram inhibits TASK tandem pore (K2P) potassium channel function but does not affect minimum alveolar anesthetic concentration.	2006-03	16492828
Chemical immobilization of adult female Weddell seals with tiletamine and zolazepam: effects of age, condition and stage of lactation.	2006-02-09	16469105
Doxapram and developmental delay at 12 months in children born extremely preterm.	2005-11	16303710
Second-degree atrioventricular heart block after doxapram administration.	1998-07	9672531
Adverse events with continuous doxapram infusion against late postoperative hypoxaemia.	1996	8737758
Double-blind comparison between doxapram and pethidine in the treatment of postanaesthetic shivering.	1993-11	8251281
Panic attacks induced by doxapram.	1993-02-15	8471685
Patient-controlled analgesia with a mixture of pethidine and doxapram hydrochloride. A comparison of the incidence of respiratory dysrhythmias with pethidine alone.	1988-03	3129954
Side effects of doxapram infusion.	1976-09	964272
Electroencephalographic effect of doxapram hydrochloride in humans.	1966	4388361

Patents

Sample Use Guides

In Vivo Use Guide

The recommended dose for I.V. administration is 0.5 – 1 mg/kg for a single injection and at 5-minute intervals. Careful observation of the patient during administration and for some time subsequently are advisable. The ma ximum total dosage by I.V. injection is 2 mg/kg.

Route of Administration: Intravenous

In Vitro Use Guide

Doxapram (1-100 uM) caused rapid, reversible and dose-dependent inhibitions of K+ currents recorded in type I cells of the neonatal rat carotid body (IC50 approximately 13 uM).

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:33:34 GMT 2025` Edited by `admin` on `Mon Mar 31 17:33:34 GMT 2025`
Record UNII	94F3830Q73
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

DOCATONE

Preferred Name

English

DOXAPRAM

Official Name

English

DOXAPRAM [HSDB]

Common Name

English

(±)-1-ETHYL-4-(2-MORPHOLINOETHYL)-3,3-DIPHENYL-2-PYRROLIDINONE

Systematic Name

English

DOXAPRAM [MI]

Common Name

English

DOXAPRAM [VANDF]

Common Name

English

2-PYRROLIDINONE, 1-ETHYL-4-(2-(4-MORPHOLINYL)ETHYL)-3,3-DIPHENYL-

Systematic Name

English

doxapram [INN]

Common Name

English

Doxapram [WHO-DD]

Common Name

English

1-ETHYL-4-(2-(4-MORPHOLINYL)ETHYL)-3,3-DIPHENYL-2-PYRROLIDINONE

Systematic Name

English

2-PYRROLIDINONE, 1-ETHYL-4-(2-(4-MORPHOLINYL)ETHYL)-3,3-DIPHENYL-, (±)-

Systematic Name

English

1-ETHYL-4-(2-MORPHOLINOETHYL)-3,3-DIPHENYL-2-PYRROLIDINONE

Systematic Name

English

DOXAPRAM [JAN]

Common Name

English

2-PYRROLIDINONE, 1-ETHYL-4-(2-MORPHOLINOETHYL)-3,3-DIPHENYL-

Systematic Name

English

Classification Tree Code System Code

WHO-ATC

R07AB01