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oxaprotiline
Sign in to saveOxaprotiline (developmental code name C 49-802 BDA), also known as hydroxymaprotiline, is a norepinephrine reuptake inhibitor belonging to the tetracyclic antidepressant (TeCA) family and is related to maprotiline. Though investigated as an antidepressant, it was never marketed.
In the Vinony graph
Within Vinony's link graph, oxaprotiline is referenced by 1,088 other articles, and connects out to propranolol, histamine antagonist and atenolol.
It sits within the topics Anthracenes, Chemical pages without DrugBank identifier and Drugboxes which contain changes to verified fields.
Its subject is documented across 4 Wikipedia language editions.
Chemical data
- Formula
- C20H23NO
- Molecular weight
- 293.4 g/mol
- IUPAC name
- 1-(methylamino)-3-(1-tetracyclo[6.6.2.02,7.09,14]hexadeca-2,4,6,9,11,13-hexaenyl)propan-2-ol
- SMILES
- CNCC(CC12CCC(C3=CC=CC=C31)C4=CC=CC=C24)O
- InChIKey
- FDXQKWSTUZCCTM-UHFFFAOYSA-N
- XLogP
- 3.6
- Polar surface area
- 32.3 Ų
- H-bond donors
- 2
- H-bond acceptors
- 2
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Phase 2
- Molecule type
- Small molecule
via ChEMBL · EBI
Research
150 papers- Oxaprotiline in the treatment of endogenous depressed inpatients an early clinical trial.Pharmacopsychiatry · 1985
- Second-generation antidepressants.The Psychiatric clinics of North America · 1984
- Oxaprotiline: induction of central noradrenergic subsensitivity of its (+)-enantiomer.Life sciences · 1982
- The metabolic fate of 14C-oxaprotiline X HCl in man. III. Stereospecific disposition.Biopharmaceutics & drug disposition · 1984
- Pharmacological effects of oxaprotiline enantiomers on the central serotonin system.Polish journal of pharmacology and pharmacy · 1989
via PubMed
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 293.178
Show 4 more facts
- chemical formula
- C₂₀H₂₃NO
- canonical SMILES
- CNCC(CC12CCC(C3=CC=CC=C31)C4=CC=CC=C24)O
- subject has role
- antidepressant
- Commons category
- Oxaprotiline
Sources (2)
via Wikidata · CC0
~1 min read
Encyclopedic overview
4 sectionsContents
- Pharmacology
- Chemistry
- See also
- References
Oxaprotiline (developmental code name C 49-802 BDA), also known as hydroxymaprotiline, is a norepinephrine reuptake inhibitor belonging to the tetracyclic antidepressant (TeCA) family and is related to maprotiline. Though investigated as an antidepressant, it was never marketed.
==Pharmacology== Dextroprotiline acts as a potent norepinephrine reuptake inhibitor and H1 receptor antagonist, as well as a very weak α1-adrenergic receptor antagonist. It has negligible affinity for the serotonin transporter, dopamine transporter, α2-adrenergic receptor, and muscarinic acetylcholine receptors. Whether it has any antagonistic effects on the 5-HT2, 5-HT7, or D2 receptors like its relative maprotiline is unclear.
Excerpted from Wikipedia’s “oxaprotiline” article, available under the CC BY-SA 4.0 licence.