Details of the Drug

General Information of Drug (ID: DMCYANK)

Drug Name
Doxapram
Synonyms
Docatone; Dopram; Doxapramum; Doxapram HCL; Doxapram hydrochloride; Docatone (TN); Dopram (TN); Doxapram (INN); Doxapram [USP:JAN]; Doxapramum [INN-Latin]; (+-)-doxapram; 1-Ethyl-4-(2-morpholinoethyl)-3,3-diphenyl-2-pyrrolidinone; 1-ethyl-4-(2-morpholin-4-ylethyl)-3,3-diphenylpyrrolidin-2-one; 1-ethyl-4-[2-(morpholin-4-yl)ethyl]-3,3-diphenylpyrrolidin-2-one; 2-Pyrrolidinone, 1-ethyl-4-(2-(4-morpholinyl)ethyl)-3,3-diphenyl-(9CI)
Indication
Disease Entry ICD 11 Status REF
Respiratory disease CB40 Approved [1]
Therapeutic Class
Central Nervous System Stimulants
Affected Organisms
Humans and other mammals
ATC Code
R07AB01: Doxapram
R07AB: Respiratory stimulants
R07A: OTHER RESPIRATORY SYSTEM PRODUCTS
R07: OTHER RESPIRATORY SYSTEM PRODUCTS
R: RESPIRATORY SYSTEM
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 378.5
Logarithm of the Partition Coefficient (xlogp) 3.3
Rotatable Bond Count (rotbonds) 6
Hydrogen Bond Donor Count (hbonddonor) 0
Hydrogen Bond Acceptor Count (hbondacc) 3
ADMET Property
Bioavailability
64% of drug becomes completely available to its intended biological destination(s) [2]
Clearance
The drug present in the plasma can be removed from the body at the rate of 5.3 mL/min/kg [3]
Half-life
The concentration or amount of drug in body reduced by one-half in 4.1 hours [3]
MRTD
The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 10.5675 micromolar/kg/day [4]
Vd
Fluid volume that would be required to contain the amount of drug present in the body at the same concentration as in the plasma 1.2 L/kg [3]
Chemical Identifiers
Formula
C24H30N2O2
IUPAC Name
1-ethyl-4-(2-morpholin-4-ylethyl)-3,3-diphenylpyrrolidin-2-one
Canonical SMILES
CCN1CC(C(C1=O)(C2=CC=CC=C2)C3=CC=CC=C3)CCN4CCOCC4
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
Cross-matching ID
PubChem CID
3156
ChEBI ID
CHEMBL1754
CAS Number
309-29-5
UNII
94F3830Q73
DrugBank ID
DB00561
TTD ID
D0M7BT
INTEDE ID
DR0541
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Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Peripheral carotid chemoreceptor (PCC) TT6EYVN NOUNIPROTAC Stimulator [5]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 3A4 (CYP3A4) DE4LYSA CP3A4_HUMAN Substrate [6]
Cytochrome P450 3A5 (CYP3A5) DEIBDNY CP3A5_HUMAN Substrate [6]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Disease Different from Doxapram (Comorbidity)
DDI Drug Name DDI Drug ID Severity Mechanism Comorbidity REF
Methylene blue DMJAPE7 Major Additive hypertensive effects by the combination of Doxapram and Methylene blue. Acquired methaemoglobinaemia [3A93] [7]
Linezolid DMGFPU2 Major Increased risk of hyperpyrexia by the combination of Doxapram and Linezolid. Bacterial infection [1A00-1C4Z] [7]
Selegiline DM6034S Major Increased risk of hyperpyrexia by the combination of Doxapram and Selegiline. Depression [6A70-6A7Z] [7]
Isocarboxazid DMAF1NB Major Increased risk of hyperpyrexia by the combination of Doxapram and Isocarboxazid. Depression [6A70-6A7Z] [7]
Tranylcypromine DMGB5RE Major Increased risk of hyperpyrexia by the combination of Doxapram and Tranylcypromine. Depression [6A70-6A7Z] [7]
Phenelzine DMHIDUE Major Increased risk of hyperpyrexia by the combination of Doxapram and Phenelzine. Depression [6A70-6A7Z] [7]
Esketamine DMVU687 Major Additive hypertensive effects by the combination of Doxapram and Esketamine. Depression [6A70-6A7Z] [8]
Procarbazine DMIK367 Major Additive hypertensive effects by the combination of Doxapram and Procarbazine. Hodgkin lymphoma [2B30] [7]
Polyethylene glycol DM4I1JP Moderate Increased risk of lowers seizure threshold by the combination of Doxapram and Polyethylene glycol. Irritable bowel syndrome [DD91] [9]
Ozanimod DMT6AM2 Major Increased risk of hyperpyrexia by the combination of Doxapram and Ozanimod. Multiple sclerosis [8A40] [7]
Bupropion DM5PCS7 Major Increased risk of lowers seizure threshold by the combination of Doxapram and Bupropion. Nicotine use disorder [6C4A] [10]
Safinamide DM0YWJC Moderate Decreased metabolism of Doxapram caused by Safinamide mediated inhibition of non-CYP450 enzyme. Parkinsonism [8A00] [11]
Rasagiline DM3WKQ4 Moderate Additive hypertensive effects by the combination of Doxapram and Rasagiline. Parkinsonism [8A00] [7]
⏷ Show the Full List of 13 DDI Information of This Drug

References

1 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 7169).
2 Critical Evaluation of Human Oral Bioavailability for Pharmaceutical Drugs by Using Various Cheminformatics Approaches
3 Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
4 Estimating the safe starting dose in phase I clinical trials and no observed effect level based on QSAR modeling of the human maximum recommended daily dose
5 Ovalbumin sensitization alters the ventilatory responses to chemical challenges in guinea pigs. J Appl Physiol (1985). 2005 Nov;99(5):1782-8.
6 Population pharmacokinetics of doxapram in low-birth-weight Japanese infants with apnea. Eur J Pediatr. 2015 Apr;174(4):509-18.
7 Ban TA "Drug interactions with psychoactive drugs." Dis Nerv Syst 36 (1975): 164-6. [PMID: 1116424]
8 Cerner Multum, Inc. "Australian Product Information.".
9 Product Information. Suprep Bowel Prep Kit (magnesium/potassium/sodium sulfates). Braintree Laboratories, Braintree, MA.
10 Product Information. Wellbutrin XL (buPROPion). GlaxoSmithKline, Philadelphia, PA.
11 Agencia Espaola de Medicamentos y Productos Sanitarios Healthcare "Centro de informacion online de medicamentos de la AEMPS - CIMA.".