CAS 309-29-5|Doxapram HCL|Doxapram|Doxapram hydrochloride|doxapram|1-ethyl-4-[2-(morpholin-4-yl)ethyl]-3,3-diphenylpyrrolidin-2-one|Stimulexin|Dopram|1-Ethyl-4-(2-morpholinoethyl)-3,3-diphenylpyrrol...

General Information

Structure

Molecular Formula

C₂₄H₃₀N₂O₂

Molecular Mass

378.5072

Exact Mass

378.23072821

Charge

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

Canonic Smiles

CCN1CC(C(C1=O)(c1ccccc1)c1ccccc1)CCN1CCOCC1

Isomeric Smiles

O=C1N(CC(C1(c1ccccc1)c1ccccc1)CCN1CCOCC1)CC

Calculated Properties

JChem

LogD (pH = 7.4)

3.01

LogD (pH = 5.5)

1.50

Log P

3.23

Rotatable Bonds

H Donor

H Acceptors

Lipinski's Rule of Five

true

Acid pKa

7.23

Polar Surface Area

32.78

Polarizability

42.91

Molar Refractivity

112.85

LOG S

-3.16

Data Source

Academic Data

Commercial Catalog

Data Source

Names and Identifiers

Brand Name

Doxapram HCLDoxapram hydrochlorideStimulexinDopram

Synonyms

Doxapram1-Ethyl-4-(2-morpholinoethyl)-3,3-diphenylpyrrolidin-2-oneDoxapram(+-)-doxapram1-ethyl-4-(2-morpholinoethyl)-3,3-diphenyl-2-pyrrolidinonedoxapram

IUPAC Traditional name

doxapram

IUPAC name

1-ethyl-4-[2-(morpholin-4-yl)ethyl]-3,3-diphenylpyrrolidin-2-one

International Nonproprietary Name (INN)

doxapram

Names and Identifiers

Registration numbers

PubChem SID

4650682916096390693608329

PubChem CID

3156

CAS Number

309-29-5

PubMed Citation Links

4122029412609652763826896538258191702014070019663568

VSDB Database

1,819

MetaboLights Database

MTBLS1918MTBLS2349MTBLS591MTBLS867MTBLS2145MTBLS3750

LINCS Database

CHEBI ID

CompTox Database

Wikipedia Title

Patent number

KEGG DRUG Database

CHEMBL

ACToR Database

SureChEMBL Database

Reaxys Registry

Beilstein Number

DrugBank ID

BindingDB Database

Drug Central Database

953

Registration numbers

Properties

Physical Property

Solubility

Sparingly soluble

Hydrophobicity(logP)

3.6

Product Information

Purity

95+%

Properties

Related Proteins

No Data Available

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Molecular Spectra

No Data Available

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Molecule Details

DrugBank

DB00561

Drug Groups

approved

Description

A central respiratory stimulant with a brief duration of action. (From Martindale, The Extra Pharmocopoeia, 30th ed, p1225)

Indication

For use as a temporary measure in hospitalized patients with acute respiratory insufficiency superimposed on chronic obstructive pulmonary disease.

Pharmacology

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.

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

References

• 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]

• Yost CS: A new look at the respiratory stimulant doxapram. CNS Drug Rev. 2006 Fall-Winter;12(3-4):236-49. [Pubmed]

External Links

• [Wikipedia]

• [RxList]

• [Drugs.com]

ChEBI

CHEBI:681848

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.

Molecule Details

References

PubChem Literature

From Data Sources

• 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

• Yost CS: A new look at the respiratory stimulant doxapram. CNS Drug Rev. 2006 Fall-Winter;12(3-4):236-49. Pubmed

References

Bioactivity

PubChem BioAssay

Bioactivity

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General Information

Calculated Properties

• RDKit

• JChem

Data Source

• Academic Data