This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Generic Name
Oxaprotiline
DrugBank Accession Number
DB09307
Background

Oxaprotiline is a norepinephrine reuptake inhibitor of the tetracyclic antidepressant family that is related to maprotiline. This drug was never marketed. Oxaprotiline is a racemic mixture of the isomers levoprotiline and dextroprotiline. Levoprotiline is the R or levo isomer of oxaprotiline (CGP-12,103-A). Dextroprotiline is the S or dextro isomer of oxaprotiline (CGP-12,104-A). Both enantiomers have antidepressant effects but levoprotiline also is an antihistamine and dextroprotiline has many other pharmacological actions.

Type
Small Molecule
Groups
Experimental
Structure
Thumb
Weight
Average: 293.41
Monoisotopic: 293.177964365
Chemical Formula
C20H23NO
Synonyms
  • Hydroxymaprotiline
  • Oxaprotilina
  • Oxaprotiline
  • Oxaprotilinum

Pharmacology

Indication

Investigated for the treatment of depression.

Pharmacology
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Contraindications & Blackbox Warnings
Contraindications
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Pharmacodynamics

Not Available

Mechanism of action
Not Available
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
Adverseeffects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
1,2-BenzodiazepineThe risk or severity of adverse effects can be increased when Oxaprotiline is combined with 1,2-Benzodiazepine.
AcarboseOxaprotiline may decrease the hypoglycemic activities of Acarbose.
AcebutololOxaprotiline may decrease the antihypertensive activities of Acebutolol.
AceclofenacThe risk or severity of gastrointestinal bleeding can be increased when Oxaprotiline is combined with Aceclofenac.
AcemetacinThe risk or severity of gastrointestinal bleeding can be increased when Oxaprotiline is combined with Acemetacin.
AcenocoumarolThe risk or severity of bleeding can be increased when Oxaprotiline is combined with Acenocoumarol.
AcetazolamideThe risk or severity of adverse effects can be increased when Acetazolamide is combined with Oxaprotiline.
AcetohexamideOxaprotiline may decrease the hypoglycemic activities of Acetohexamide.
AcetophenazineThe serum concentration of Oxaprotiline can be increased when it is combined with Acetophenazine.
Acetylsalicylic acidThe risk or severity of gastrointestinal bleeding can be increased when Oxaprotiline is combined with Acetylsalicylic acid.
Interactions
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Food Interactions
Not Available

Categories

Drug Categories
Classification
Not classified
Affected organisms
Not Available

Chemical Identifiers

UNII
3V3Z2HK4LS
CAS number
56433-44-4
InChI Key
FDXQKWSTUZCCTM-UHFFFAOYSA-N
InChI
InChI=1S/C20H23NO/c1-21-13-14(22)12-20-11-10-15(16-6-2-4-8-18(16)20)17-7-3-5-9-19(17)20/h2-9,14-15,21-22H,10-13H2,1H3
IUPAC Name
1-(methylamino)-3-{tetracyclo[6.6.2.0^{2,7}.0^{9,14}]hexadeca-2,4,6,9,11,13-hexaen-1-yl}propan-2-ol
SMILES
CNCC(O)CC12CCC(C3=CC=CC=C13)C1=CC=CC=C21

References

General References
Not Available
PubChem Substance
347910433
ChemSpider
35026
ChEMBL
CHEMBL1213009
Wikipedia
Oxaprotiline

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00324 mg/mLALOGPS
logP3.56ALOGPS
logP3.3ChemAxon
logS-5ALOGPS
pKa (Strongest Acidic)14.86ChemAxon
pKa (Strongest Basic)9.92ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area32.26 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity100.66 m3·mol-1ChemAxon
Polarizability34.07 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
Not Available

Drug created at November 12, 2015 16:25 / Updated at May 14, 2021 01:05