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

• ChemBase ID: 443
• Molecular Formular: C24H30N2O2
• Molecular Mass: 378.5072
• Monoisotopic Mass: 378.23072821
• SMILES: O=C1N(CC(C1(c1ccccc1)c1ccccc1)CCN1CCOCC1)CC
• Canonical SMILES: CCN1CC(C(C1=O)(c1ccccc1)c1ccccc1)CCN1CCOCC1
• 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

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-ethyl-4-[2-(morpholin-4-yl)ethyl]-3,3-diphenylpyrrolidin-2-one
• IUPAC Traditional name: doxapram
• Brand Name: Dopram; Doxapram HCL; Doxapram hydrochloride; Stimulexin
• Synonyms: Doxapram; 1-Ethyl-4-(2-morpholinoethyl)-3,3-diphenylpyrrolidin-2-one

Database IDs

• CAS Number: 309-29-5
• PubChem SID: 46506829; 160963906
• PubChem CID: 3156

CALCULATED PROPERTIES

JChem

• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 1.4981233
• LogD (pH = 7.4): 3.0056586
• Log P: 3.2305923
• Molar Refractivity: 112.8508 cm^3
• Polarizability: 44.003464 Å^3
• Polar Surface Area: 32.78 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 3.65
• LOG S: -4.04
• Solubility (Water): 3.43e-02 g/l

PROPERTIES

Physical Property

• Solubility: Sparingly soluble
• Hydrophobicity(logP): 3.6

Product Information

• Purity: 95+%

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

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