Details
Stereochemistry | RACEMIC |
Molecular Formula | C24H30N2O2.ClH.H2O |
Molecular Weight | 432.983 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
O.Cl.CCN1CC(CCN2CCOCC2)C(C1=O)(C3=CC=CC=C3)C4=CC=CC=C4
InChI
InChIKey=ZOMBFZRWMLIDPX-UHFFFAOYSA-N
InChI=1S/C24H30N2O2.ClH.H2O/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;1H;1H2
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 | ( + / - ) |
Molecular Formula | ClH |
Molecular Weight | 36.461 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Molecular Formula | H2O |
Molecular Weight | 18.0153 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
DescriptionSources: http://www.drugbank.ca/drugs/DB00561Curator's Comment: Description was created based on several sources, including
http://www.accessdata.fda.gov/drugsatfda_docs/label/2005/14879s044lbl.pdf
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
Sources: http://www.drugbank.ca/drugs/DB00561
Curator's Comment: a stimulant of the central nervous system
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2321613 Sources: http://www.drugbank.ca/drugs/DB00561 |
|||
Target ID: CHEMBL2321614 Sources: http://www.drugbank.ca/drugs/DB00561 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Secondary | Doxapram Approved UsePostanesthesia
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-1.42905606E11 |
|||
Primary | Doxapram Approved UsePostanesthesia
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-1.42905606E11 |
Cmax
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 |
|
51927 ng × min/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9109960 |
0.55 mg/kg bw 1 times / day steady-state, intravenous dose: 0.55 mg/kg bw route of administration: Intravenous experiment type: STEADY-STATE co-administered: |
DOXAPRAM plasma | Equus caballus population: HEALTHY age: ADULT sex: MALE food status: FASTED |
T1/2
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 |
|
121 min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9109960 |
0.55 mg/kg bw 1 times / day steady-state, intravenous dose: 0.55 mg/kg bw route of administration: Intravenous experiment type: STEADY-STATE co-administered: |
DOXAPRAM plasma | Equus caballus population: HEALTHY age: ADULT sex: MALE food status: FASTED |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
21% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9109960 |
0.55 mg/kg bw 1 times / day steady-state, intravenous dose: 0.55 mg/kg bw route of administration: Intravenous experiment type: STEADY-STATE co-administered: |
DOXAPRAM plasma | Equus caballus population: HEALTHY age: ADULT sex: MALE food status: FASTED |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: 8.0 |
negligible | |||
Page: 8.0 |
negligible | |||
Page: 8.0 |
no | |||
Page: 8.0 |
no | |||
Page: 8.0 |
no | |||
Page: 8.0 |
no | |||
Page: 8.0 |
no | |||
Page: 8.0 |
yes | |||
Page: 8.0 |
yes |
PubMed
Title | Date | PubMed |
---|---|---|
Electroencephalographic effect of doxapram hydrochloride in humans. | 1966 |
|
Side effects of doxapram infusion. | 1976 Sep |
|
Patient-controlled analgesia with a mixture of pethidine and doxapram hydrochloride. A comparison of the incidence of respiratory dysrhythmias with pethidine alone. | 1988 Mar |
|
Panic attacks induced by doxapram. | 1993 Feb 15 |
|
Double-blind comparison between doxapram and pethidine in the treatment of postanaesthetic shivering. | 1993 Nov |
|
Adverse events with continuous doxapram infusion against late postoperative hypoxaemia. | 1996 |
|
Second-degree atrioventricular heart block after doxapram administration. | 1998 Jul |
|
Doxapram and developmental delay at 12 months in children born extremely preterm. | 2005 Nov |
|
[Clinical observation of target-controlled remifentanil infusion combined with propofol and doxapram in painless artificial abortion]. | 2006 Aug |
|
A new look at the respiratory stimulant doxapram. | 2006 Fall-Winter |
|
Chemical immobilization of adult female Weddell seals with tiletamine and zolazepam: effects of age, condition and stage of lactation. | 2006 Feb 9 |
|
Frequency of apnea, bradycardia, and desaturations following first diphtheria-tetanus-pertussis-inactivated polio-Haemophilus influenzae type B immunization in hospitalized preterm infants. | 2006 Jun 19 |
|
The ventilatory stimulant doxapram inhibits TASK tandem pore (K2P) potassium channel function but does not affect minimum alveolar anesthetic concentration. | 2006 Mar |
|
Doxapram shortens recovery following sevoflurane anesthesia. | 2006 May |
|
European Academy of Paediatrics, Barcelona, Spain, October 7-10, 2006. Abstracts. | 2006 Nov |
|
Doxapram and aminophylline on bispectral index under sevoflurane anaesthesia: a comparative study. | 2006 Nov |
|
[Determination of methamphetamine in whole blood by capillary zone electrophoresis after solid phase extraction]. | 2006 Oct 15 |
|
[Analysis of 37 drugs in whole blood by HPLC after solid phase extraction]. | 2006 Oct 15 |
|
Dynamic QT/RR relationship of cardiac conduction in premature infants treated with low-dose doxapram hydrochloride. | 2007 |
|
HPA axis activity in patients with panic disorder: review and synthesis of four studies. | 2007 |
|
Comparison of the effects of caffeine and doxapram on respiratory and cardiovascular function in foals with induced respiratory acidosis. | 2007 Dec |
|
Creatine supplementation attenuates corticosteroid-induced muscle wasting and impairment of exercise performance in rats. | 2007 Feb |
|
[Sensory stimulations for the treatment of idiopathic apneas of prematurity]. | 2007 May |
|
The effect of doxapram on brain imaging in patients with panic disorder. | 2007 Oct |
|
Respiratory irregularity and stress hormones in panic disorder: exploring potential linkages. | 2008 |
|
Managing acute on chronic respiratory failure: a guide to non-invasive ventilation. | 2008 Aug |
|
Acid-sensitive channel inhibition prevents fetal alcohol spectrum disorders cerebellar Purkinje cell loss. | 2008 Aug |
|
Retrospective comparison of caffeine and doxapram for the treatment of hypercapnia in foals with hypoxic-ischemic encephalopathy. | 2008 Mar-Apr |
|
Difficult extubation in low birthweight infants. | 2008 May |
|
[Recommended treatment of apnea in premature infants. A review based on literature and own experience]. | 2008 Oct-Dec |
|
Comparative study on effectiveness of doxapram and pethidine for postanaesthetic shivering. | 2009 Apr-Jun |
|
Doxapram revisited in patients with cancer. | 2009 Aug |
|
Management and prevention of chronic obstructive pulmonary disease exacerbations: a state of the art review. | 2009 Aug 7 |
|
Decreased neurokinin-1 (substance P) receptor binding in patients with panic disorder: positron emission tomographic study with [18F]SPA-RQ. | 2009 Jul 1 |
|
Prophylactic granisetron vs pethidine for the prevention of postoperative shivering: a randomized control trial. | 2009 Jun |
|
Presumptive benzocaine-induced methemoglobinemia in a slender-tailed meerkat (Suricata suricatta). | 2009 Jun |
|
Neuroimaging in anxiety disorders. | 2009 Jun |
|
Transdermal buprenorphine - a critical appraisal of its role in pain management. | 2009 Sep 15 |
|
Effects of serotonin agonists and doxapram on respiratory depression and hypoxemia in etorphine-immobilized impala (Aepyceros melampus). | 2010 Apr |
|
Chronic hypoxia increases the gain of the hypoxic ventilatory response by a mechanism in the central nervous system. | 2010 Aug |
|
Intrathecal meperidine reduces intraoperative shivering during transurethral prostatectomy in elderly patients. | 2010 Dec |
|
The clinical practice of CPCR in small animals: an internet-based survey. | 2010 Dec |
|
[Effect of doxapram on the respiratory rhythmical discharge activity in the brainstem slice of neonatal rats]. | 2010 Feb |
|
Surfactant without intubation in preterm infants with respiratory distress: first multi-center data. | 2010 Jan-Feb |
|
Glial cells are involved in the exciting effects of doxapram on brainstem slices in vitro. | 2010 Jul |
|
Respiratory inductive plethysmography as a method for measuring ventilatory parameters in conscious, non-restrained dogs. | 2010 Jul-Aug |
|
Chemical immobilization of Weddell seals (Leptonychotes weddellii) by ketamine/midazolam combination. | 2010 Mar |
|
Respiratory and cardiovascular effects of doxapram and theophylline for the treatment of asphyxia in neonatal calves. | 2010 Mar 15 |
|
Emergence agitation in adults: risk factors in 2,000 patients. | 2010 Sep |
|
Evaluation of respiratory function in freely moving Beagle dogs using implanted impedance technology. | 2010 Sep-Oct |
Patents
Sample Use Guides
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/1667613
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
Edited
Fri Dec 15 16:34:54 UTC 2023
by
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on
Fri Dec 15 16:34:54 UTC 2023
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Record UNII |
P5RU6UOQ5Y
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Record Status |
Validated (UNII)
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Record Version |
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NCI_THESAURUS |
C47795
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C47500
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DTXSID60991081
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Related Record | Type | Details | ||
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ANHYDROUS->SOLVATE | |||
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BASIS OF STRENGTH->SUBSTANCE |
Dried at 105 for 2 hours
ASSAY (TITRATION)
USP
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ENANTIOMER -> RACEMATE | |||
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ENANTIOMER -> RACEMATE | |||
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PARENT -> SALT/SOLVATE | |||
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BASIS OF STRENGTH->SUBSTANCE |
ASSAY (TITRATION)
EP
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Related Record | Type | Details | ||
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ACTIVE MOIETY |