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Identification
Name Doxapram
Accession Number DB00561 (APRD00935)
Type small molecule
Groups approved
Description

A central respiratory stimulant with a brief duration of action. (From Martindale, The Extra Pharmocopoeia, 30th ed, p1225)
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms Not Available
Salts Not Available
Brand names
Name Company
Dopram
Doxapram HCL
Doxapram hydrochloride
Stimulexin
Brand mixtures Not Available
Categories
  • Central Nervous System Stimulants
  • Respiratory System Agents
CAS number 309-29-5
Weight Average: 378.5072
Monoisotopic: 378.230728214
Chemical Formula C24H30N2O2
InChI Key InChIKey=XFDJYSQDBULQSI-UHFFFAOYSA-N
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
Plain Text
IUPAC Name
1-ethyl-4-[2-(morpholin-4-yl)ethyl]-3,3-diphenylpyrrolidin-2-one
SMILES
CCN1CC(CCN2CCOCC2)C(C1=O)(C1=CC=CC=C1)C1=CC=CC=C1
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Organic
Classes
  • Diphenylmethanes
  • Gamma Lactams
Substructures
  • Carbonyl Compounds
  • Amino Ketones
  • Pyrrolidines
  • Ethers
  • Benzene and Derivatives
  • Aliphatic and Aryl Amines
  • Diphenylmethanes
  • Phenethylamines
  • Heterocyclic compounds
  • Aromatic compounds
  • Carboxamides and Derivatives
  • Phenylpropylamines
  • Gamma Lactams
  • Morpholines
  • Lactams
Pharmacology
Indication For use as a temporary measure in hospitalized patients with acute respiratory insufficiency superimposed on chronic obstructive pulmonary disease.
Pharmacodynamics 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.
Mechanism of action Doxapram produces respiratory stimulation mediated through the peripheral carotid chemoreceptors. It is thought to stimulate the carotid body by inhibiting certain potassium channels.
Absorption Not Available
Volume of distribution Not Available
Protein binding Not Available
Metabolism
Not Available
Route of elimination Not Available
Half life Not Available
Clearance Not Available
Toxicity Intravenous LD50 values in the mouse and rat were approximately 75 mg/kg and in the cat and dog were 40 to 80 mg/kg. Symptoms of overdosage are extensions of the pharmacologic effects of the drug. Excessive pressor effect, tachycardia, skeletal muscle hyperactivity, and enhanced deep tendon reflexes may be early signs of overdosage.
Affected organisms
  • Humans and other mammals
Pathways Not Available
Pharmacoeconomics
Manufacturers
  • Baxter healthcare corp anesthesia and critical care
  • Bedford laboratories div ben venue laboratories inc
  • Watson laboratories inc
Packagers
Dosage forms
Form Route Strength
Injection, solution Intravenous
Prices
Unit description Cost Unit
Doxapram hcl 20 mg/ml vial 4.67 USD ml
Dopram 20 mg/ml vial 2.52 USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents Not Available
Properties
State solid
Experimental Properties
Property Value Source
water solubility Sparingly soluble Not Available
logP 3.6 Not Available
Predicted Properties
Property Value Source
water solubility 3.43e-02 g/l ALOGPS
logP 3.65 ALOGPS
logP 3.23 ChemAxon
logS -4 ALOGPS
pKa (strongest basic) 7.23 ChemAxon
physiological charge 1 ChemAxon
hydrogen acceptor count 3 ChemAxon
hydrogen donor count 0 ChemAxon
polar surface area 32.78 ChemAxon
rotatable bond count 6 ChemAxon
refractivity 112.85 ChemAxon
polarizability 43.02 ChemAxon
References
Synthesis Reference Not Available
General Reference
  1. Singh P, Dimitriou V, Mahajan RP, Crossley AW: Double-blind comparison between doxapram and pethidine in the treatment of postanaesthetic shivering. Br J Anaesth. 1993 Nov;71(5):685-8. Pubmed
  2. Yost CS: A new look at the respiratory stimulant doxapram. CNS Drug Rev. 2006 Fall-Winter;12(3-4):236-49. Pubmed
External Links
Resource Link
KEGG Drug D01872 Link_out
PubChem Compound 3156 Link_out
PubChem Substance 46506829 Link_out
ChemSpider 3044 Link_out
ChEBI 681848 Link_out
ChEMBL 681848 Link_out
Therapeutic Targets Database DAP001295 Link_out
PharmGKB PA164784026 Link_out
Drug Product Database 1914154 Link_out
RxList http://www.rxlist.com/cgi/generic2/doxapram.htm Link_out
Drugs.com http://www.drugs.com/cdi/doxapram.html Link_out
Wikipedia http://en.wikipedia.org/wiki/Doxapram Link_out
ATC Codes
  • R07AB01
AHFS Codes Not Available
PDB Entries Not Available
FDA label show (224 KB)
MSDS show (50.7 KB)
Interactions
Drug Interactions Not Available
Food Interactions Not Available
Targets

1. Potassium channel subfamily K member 3

Pharmacological action: yes
Actions: inhibitor

pH-dependent, voltage-insensitive, background potassium channel protein. Rectification direction results from potassium ion concentration on either side of the membrane. Acts as an outward rectifier when external potassium concentration is low. When external potassium concentration is high, current is inward

Organism class: human
UniProt ID: O14649 Link_out
Gene: KCNK3 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Yost CS: A new look at the respiratory stimulant doxapram. CNS Drug Rev. 2006 Fall-Winter;12(3-4):236-49. Pubmed
  2. Anderson-Beck R, Wilson L, Brazier S, Hughes IE, Peers C: Doxapram stimulates dopamine release from the intact rat carotid body in vitro. Neurosci Lett. 1995 Feb 24;187(1):25-8. Pubmed
  3. Peers C: Effects of doxapram on ionic currents recorded in isolated type I cells of the neonatal rat carotid body. Brain Res. 1991 Dec 24;568(1-2):116-22. Pubmed

2. Potassium channel subfamily K member 9

Pharmacological action: yes
Actions: inhibitor

pH-dependent, voltage-insensitive, background potassium channel protein

Organism class: human
UniProt ID: Q9NPC2 Link_out
Gene: KCNK9 Link_out
Protein Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Yost CS: A new look at the respiratory stimulant doxapram. CNS Drug Rev. 2006 Fall-Winter;12(3-4):236-49. Pubmed
  2. Anderson-Beck R, Wilson L, Brazier S, Hughes IE, Peers C: Doxapram stimulates dopamine release from the intact rat carotid body in vitro. Neurosci Lett. 1995 Feb 24;187(1):25-8. Pubmed
  3. Peers C: Effects of doxapram on ionic currents recorded in isolated type I cells of the neonatal rat carotid body. Brain Res. 1991 Dec 24;568(1-2):116-22. Pubmed
Comments
Drug created on June 13, 2005 07:24 / Updated on February 08, 2013 16:19