Basic information
- CAS
309-29-5- Standard SMILES
CCN1CC(CCN2CCOCC2)C(c2ccccc2)(c2ccccc2)C1=O- InChIKey
XFDJYSQDBULQSI-UHFFFAOYSA-N- Molecular formula
- C24H30N2O2
- Average molar mass
- 378.5 g/mol
- Monoisotopic mass
- 378.2307282
Overview
Doxapram is 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. It has a role as a central nervous system stimulant. It is a member of morpholines and a member of pyrrolidin-2-ones.
Names & identifiers
- Preferred name
- Doxapram
- IUPAC
- 1-ethyl-4-(2-morpholin-4-ylethyl)-3,3-diphenylpyrrolidin-2-one
- English name
- Doxapram
- Molecular formula
- C24H30N2O2
- Molecular weight
- 378.51
Names & synonyms
doxapram309-29-5DoxapramumDocatone2-Pyrrolidinone, 1-ethyl-4-[2-(4-morpholinyl)ethyl]-3,3-diphenyl-1-Ethyl-4-(2-morpholinoethyl)-3,3-diphenyl-2-pyrrolidinone(+-)-doxapram2-Pyrrolidinone, 1-ethyl-4-(2-morpholinoethyl)-3,3-diphenyl-1-ethyl-4-[2-(morpholin-4-yl)ethyl]-3,3-diphenylpyrrolidin-2-oneCHEBI:6818482-Pyrrolidinone, 1-ethyl-4-(2-(4-morpholinyl)ethyl)-3,3-diphenyl-94F3830Q73
Show more names
ahr619DopramdopreamAHR-619DOXOPRAMRespiramDoxapram USP/EP/BPDOPRAMSTIMULEXRESPIRAMDoxapram (AHR-619, Dopram, Stimulex or Respiram)
DTXSID2022963AHR 6191-ethyl-4-(2-(morpholin-4-yl)ethyl)-3,3-diphenylpyrrolidin-2-oneHydrochloride, DoxapramRefChem:56559DTXCID002963R07AB01206-216-3
Database identifiers
Properties
Computed structural properties
- XLogP
- 3.3
- Topological polar surface area
- 32.8 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 6
- Heavy atoms
- 28
- Formal charge
- 0
- Complexity
- 487
Experimental & physicochemical properties
LogP3.6
Solubility
Sparingly soluble
WHITE TO OFF-WHITE CRYSTALLINE POWDER; PRACTICALLY INSOL IN ETHER /HYDROCHLORIDE/
3.43e-02 g/L
Human DrugsPharmaceuticals
Melting Point
217-219
MP: 123-124 °C /BENZOATE/
Physical DescriptionSolid
Stability/Shelf LifeSTABLE IN LIGHT & IN AIR /HYDROCHLORIDE/
Collision Cross Section
183.4 Ų [M+H]+ [CCS Type: TW; Method: Major Mix IMS/Tof Calibration Kit (Waters)]
185 Ų [M+H]+ [CCS Type: DT; Method: single field calibrated]
Other Experimental PropertiesCRYSTALS FROM ISOPROPYL ETHER; BITTER TASTE; MP: 217-219 °C; SOL IN WATER; SPARINGLY SOL IN ALC; SLIGHTLY SOL IN CHLOROFORM /HYDROCHLORIDE/
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
P264+P265, P280, P305+P351+P338, and P337+P317 (click each P-code to see the statement)
The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.
Hazard information
Hazard Classes and CategoriesEye Irrit. 2 (100%)
Toxicology
Human Toxicity Excerpts...SIDE EFFECTS INDICATIVE OF SUBCONVULSIVE CNS STIMULATION /ARE/... HYPERTENSION, TACHYCARDIA, ARRHYTHMIAS, COUGHING, SNEEZING, VOMITING, ITCHING, TREMORS, MUSCLE RIGIDITY, SWEATING, FLUSHING, & HYPERPYREXIA.
Drug Induced Liver Injury
Drug-Induced Liver Injury Severity and Toxicity (DILIst)
doxapram
DILI Negative
Intravenous
DOI:10.1016/j.drudis.2019.09.022
Non-Human Toxicity Excerpts
OVERDOSAGE /OF DOXAPRAM TO DOGS/ CAUSED CONSTRICTION OF CEREBRAL VESSELS & REDUCED CEREBRAL BLOOD FLOW & PRODUCED TISSUE ANOXIA SECONDARY TO RESP STIMULATION & LOSS OF CO2. PETECHIAL & PERIVASCULAR HEMORRHAGES WERE FOUND THROUGHOUT BRAIN, BUT...HISTOLOGIC EXAM SHOWED NO ABNORMALITY IN EYES OR OPTIC NERVES. /HYDROCHLORIDE/
Safety data
- Signal word
- Warning
- Symbol(GHS)
- GHS07
Chemistry & industry
Pharmacology
ATC Code
R - Respiratory system
QR - Respiratory system
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.
DOXAPRAM...STIMULATE ALL LEVELS OF CEREBROSPINAL AXIS. ADEQUATE DOSES PRODUCE TONIC-CLONIC CONVULSIONS SIMILAR IN PATTERN TO THOSE PRODUCED BY PENTYLENETETRAZOL. ...ACT BY ENHANCING EXCITATION RATHER THAN BY BLOCKING CENTRAL INHIBITION.
Biological Half-LifeAFTER IV DOXAPRAM-HCL BOLUS INJECTIONS OR BRIEF INFUSIONS IN HEALTHY VOLUNTEER, PLASMA CONCN DECLINED IN MULTI-EXPONENTIAL FASHION. HALF-LIFE FROM 4-12 HR WAS 3.4.
Metabolism/Metabolites
DOXAPRAM YIELDS 4-(2-MORPHOLINOETHYL)-3,3-DIPHENYLPYRROLIDIN-2-ONE, & 1-ETHYL-4-(2-(3-OXOMORPHOLINO)ETHYL)-3,3-DIPHENYLPYRROLIDIN-2-ONE IN DOGS. PITTS, JE, BRUCE, RB, & FOREHAND, JB, XENOBIOTICA, 3, 73 (1973). /FROM TABLE/
AFTER IV DOXAPRAM-HCL BOLUS INJECTIONS OR BRIEF INFUSIONS IN HEALTHY VOLUNTEERS, A METABOLITE AHR 5955 WAS PRESENT IN PLASMA IN AMT COMPARABLE TO PARENT COMPD & HAD A SIMILAR HALF-LIFE.
FDA Pharmacological Classification
94F3830Q73
DOXAPRAM
Physiologic Effects [PE] - Increased Medullary Respiratory Drive
Established Pharmacologic Class [EPC] - Respiratory Stimulant
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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