Doxepin

CAS No:
1668-19-5 Category:
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Product Details:

  • CAS No: 1668-19-5
  • AHFC code: 84:08.00 28:16.04.28
  • Synonyms: Doxepin Hcl Doxepin, Hydrochloride Doxepina [INN-Spanish] Doxepine Doxepinum [INN-Latin]
  • ATC Code: N06AA12
  • Chemical Formula: C27H29NO11
  • Molecular Weight: 279.3761
  • Assay/Purity: Typically NLT 98%
  • DrugBank: DB01142 (APRD00398)
  • SMILES: [H]C(CCN(C)C)=C1C2=CC=CC=C2COC2=CC=CC=C12
  • InChl: ODQWQRRAPPTVAG-BOPFTXTBSA-N
  • PubChem: 3158
  • IUPAC: dimethyl(3-{9-oxatricyclo[9.4.0.0^{3,8}]pentadeca-1(11),3(8),4,6,12,14-hexaen-2-ylidene}propyl)amine

Additional Details

Indication:
Labeled indications: depression and insomnia. Unlabeled indications: chronic and neuropathic pain, anxiety, idiopathic urticaria.
Pharmacodynamics:
Doxepin, a tricyclic antidepressant of the dibenzoxepin type, is used to treat depression and anxiety and, topically, pruritus associated with eczema. Doxepin has substantial anticholinergic and sedative effects.
Mode of Action:
The mechanism of action of doxepin is not completely understood. It is thought that Like amitriptyline, doxepin enhances the actions of norepinephrine and serotonin by blocking their reuptake at the neuronal membrane. Doxepin may also act on histamine H_-receptors, resulting in sedative effects, and _-adrenergic receptors.
Metabolism:
Extensively metabolized in the liver via the same pathways as other TCAs. N-demethylation produces an active metabolite, N-desmethyldoxepin.
Toxicity:
LD50=26 (mg/kg) (in mice, iv); LD50=16 (mg/kg) (in rats, iv); Cardiac dysrhythmias, severe hypotension, convulsions, and CNS depression, including coma. Changes in the electrocardiogram, particularly in QRS axis or width, are clinically significant indicators of tricyclic antidepressant toxicity. Side effects include: sedation, hypotension, blurred vision, dry mouth, constipation, urinary retention, postural hypotension, tachycardia, hypertension, ECG changes, heart failure, impaired memory and delirium, and precipitation of hypomanic or manic episodes in bipolar depression. Withdrawal symptoms include gastrointestinal disturbances, anxiety, and insomnia.
General Reference:
Products currently covered by valid US Patents are offered for R&D use in accordance with 35 USC 271(e)+A13(1). Any patent infringement and resulting liability is solely at buyer risk.

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