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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:50 UTC
Update Date2021-09-14 15:46:14 UTC
HMDB IDHMDB0014701
Secondary Accession Numbers
  • HMDB14701
Metabolite Identification
Common NameDoxapram
DescriptionDoxapram, also known as docatone or (+-)-doxapram, belongs to the class of organic compounds known as diphenylmethanes. Diphenylmethanes are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups. Doxapram is a drug which is used for use as a temporary measure in hospitalized patients with acute respiratory insufficiency superimposed on chronic obstructive pulmonary disease. Based on a literature review a significant number of articles have been published on Doxapram.
Structure
Data?1582753210
Synonyms
ValueSource
(+-)-DoxapramChEBI
1-Ethyl-4-(2-morpholinoethyl)-3,3-diphenyl-2-pyrrolidinoneChEBI
DocatoneKegg
AHP brand OF doxapram hydrochlorideHMDB
Hydrochloride, doxapramHMDB
Riemser brand OF doxapram hydrochlorideHMDB
Wyeth brand OF doxapramHMDB
Genopharm brand OF doxapram hydrochlorideHMDB
Antigen brand OF doxapram hydrochlorideHMDB
Doxapram hydrochlorideHMDB
Wyeth brand OF doxapram hydrochlorideHMDB
DopramHMDB
Chemical FormulaC24H30N2O2
Average Molecular Weight378.5072
Monoisotopic Molecular Weight378.230728214
IUPAC Name1-ethyl-4-[2-(morpholin-4-yl)ethyl]-3,3-diphenylpyrrolidin-2-one
Traditional Namedoxapram
CAS Registry Number309-29-5
SMILES
CCN1CC(CCN2CCOCC2)C(C1=O)(C1=CC=CC=C1)C1=CC=CC=C1
InChI Identifier
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
InChI KeyXFDJYSQDBULQSI-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as diphenylmethanes. Diphenylmethanes are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassDiphenylmethanes
Direct ParentDiphenylmethanes
Alternative Parents
Substituents
  • Diphenylmethane
  • 3-phenylpyrrolidine
  • Aralkylamine
  • Morpholine
  • Oxazinane
  • Pyrrolidone
  • 2-pyrrolidone
  • N-alkylpyrrolidine
  • Pyrrole
  • Pyrrolidine
  • Tertiary carboxylic acid amide
  • Tertiary amine
  • Amino acid or derivatives
  • Tertiary aliphatic amine
  • Carboxamide group
  • Lactam
  • Organoheterocyclic compound
  • Oxacycle
  • Azacycle
  • Carboxylic acid derivative
  • Dialkyl ether
  • Ether
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Organooxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Carbonyl group
  • Amine
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.034 g/LNot Available
LogP3.6Not Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+CBM183.430932474
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.034 g/LALOGPS
logP10(3.65) g/LALOGPS
logP10(3.23) g/LChemAxon
logS10(-4) g/LALOGPS
pKa (Strongest Basic)7.23ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area32.78 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity112.85 m³·mol⁻¹ChemAxon
Polarizability43.02 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+188.54631661259
DarkChem[M-H]-189.34231661259

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
DoxapramCCN1CC(CCN2CCOCC2)C(C1=O)(C1=CC=CC=C1)C1=CC=CC=C13752.7Standard polar33892256
DoxapramCCN1CC(CCN2CCOCC2)C(C1=O)(C1=CC=CC=C1)C1=CC=CC=C12962.0Standard non polar33892256
DoxapramCCN1CC(CCN2CCOCC2)C(C1=O)(C1=CC=CC=C1)C1=CC=CC=C12824.7Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Doxapram GC-MS (Non-derivatized) - 70eV, Positivesplash10-0i2c-5659000000-be23830af6d9087814ee2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Doxapram GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Doxapram , positive-QTOFsplash10-004i-0329000000-18907cc9c391c98b3b372017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Doxapram 35V, Positive-QTOFsplash10-002f-4795000000-b282c5e89dd38c3bd1022021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Doxapram 10V, Positive-QTOFsplash10-004i-0019000000-7388549b90a129ecea292016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Doxapram 20V, Positive-QTOFsplash10-016r-0923000000-fd4fdb00610b243a10902016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Doxapram 40V, Positive-QTOFsplash10-014l-6931000000-1265933cebd94c823bf12016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Doxapram 10V, Negative-QTOFsplash10-004i-0019000000-fc11ef54ebcd076d9cbc2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Doxapram 20V, Negative-QTOFsplash10-004i-1019000000-a3f15077c822e810dc4f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Doxapram 40V, Negative-QTOFsplash10-05n0-9258000000-dae2a47b8643c6398d752016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Doxapram 10V, Positive-QTOFsplash10-004i-0009000000-bb513d4d6fc6677b22672021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Doxapram 20V, Positive-QTOFsplash10-0006-0091000000-bda540c1b6f859d2a0642021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Doxapram 40V, Positive-QTOFsplash10-05mo-0295000000-a4ceb24cad9c7292389e2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Doxapram 10V, Negative-QTOFsplash10-004i-0009000000-974a448b0b2dd09672c62021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Doxapram 20V, Negative-QTOFsplash10-004j-0049000000-7bc57bde396b93d25c902021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Doxapram 40V, Negative-QTOFsplash10-000i-2964000000-1059ea9825c11e5a73cb2021-09-22Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00561 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00561 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00561
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID3044
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkDoxapram
METLIN IDNot Available
PubChem Compound3156
PDB IDNot Available
ChEBI ID681848
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Yost CS: A new look at the respiratory stimulant doxapram. CNS Drug Rev. 2006 Fall-Winter;12(3-4):236-49. [PubMed:17227289 ]
  2. 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:8251281 ]

Enzymes

General function:
Involved in potassium channel activity
Specific function:
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
Gene Name:
KCNK3
Uniprot ID:
O14649
Molecular weight:
43517.7
References
  1. Yost CS: A new look at the respiratory stimulant doxapram. CNS Drug Rev. 2006 Fall-Winter;12(3-4):236-49. [PubMed:17227289 ]
  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:7617294 ]
  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:1667613 ]