hyoscyamine

Small moleculeexperimental

Hyoscyamine as a natural plant alkaloid derivative and anticholinergic. Hyoscyamine is used to treat a variety of stomach/intestinal problems such as cramps and irritable bowel syndrome. It is also used to treat other conditions such as bladder and bowel control problems, cramping pain caused by kidney stones and gallstones, and Parkinson's disease. In addition, it is used to decrease side effects of certain medications (drugs used to treat myasthenia gravis) and insecticides. Hyoscyamine inhibits specifically the actions of acetylcholine on structures innervated by postganglionic cholinergic nerves and on smooth muscles that respond to acetylcholine but lack cholinergic innervation. These peripheral cholinergic receptors are present in the autonomic effector cells of the smooth muscle, cardiac muscle, the sinoatrial node, the atrioventricular node, and the exocrine glands. At therapeutic doses, it is completely devoid of any action on autonomic ganglia. Side effects include dry mouth and throat, increased appetite leading to weight gain, eye pain, blurred vision, restlessness, dizziness, arrhythmia, flushing, and faintness. Additive adverse effects resulting from cholinergic blockade may occur when hyoscyamine is administered concomitantly with other antimuscarinics, amantadine, haloperidol, phenothiazines, monoamine oxidase (MAO) inhibitors, tricyclic antidepressants or some antihistamines. — NCATS

Chemistry & pharmacology

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SMILES

CN1[C@H]2CC[C@@H]1C[C@@H](C2)OC(=O)[C@H](CO)C3=CC=CC=C3
Mol. weight
289.3694 g/mol
Lipinski Ro5
Pass
Rule of 3
No
Chirality
Single Stereoisomer
Inorganic
No
Polymer
No

Oral

No

Parenteral

No

Topical

No

Sources

Also known as

  • [3(s)-endo]-α-(hydroxymethyl)benzeneacetic acid 8-methyl-8-azabicyclo[3.2.1]oct-3-yl ester
  • [3(s)-endo]-α-(hydroxymethyl)benzeneacetic acid 8-methyl-8-azabicyclo[3.2.1]oct-3-yl ester
  • (-)-atropine
  • daturin
  • daturin
  • daturine
  • daturine
  • duboisine
  • duboisine
  • hyoscyamin
  • hyoscyamin
  • hyoscyamine
  • hyoscyamine
  • hyoscyamine
  • hyoscyamine
  • hyoscyamine
  • hyoscyamine
  • hyoscyamine
  • hyoscyamine
  • hyoscyamine
  • hyoscyamine
  • (-)-hyoscyamine
  • (−)-hyoscyamine
  • (−)-hyoscyamine
  • hyoscyamine sulfate
  • hyoscyamine sulfate
  • hyoscyamine sulfate
  • hyoscyamine sulphate
  • hyoscyamine sulphate
  • hyoscyaminum
  • hyoscyaminum
  • l-atropine
  • levsin
  • levsin
  • levsinex
  • levsinex
  • levsinex timecaps
  • levsin sl
  • levsin sl
  • l-hyoscyamin
  • l-hyoscyamine
  • l-hyoscyamine
  • l-hyoscyamine
  • neoquess
  • neoquess
  • peptard
  • peptard
  • (s)-atropine
  • (s)-atropine
  • (s)-(−)-hyoscyamine
  • (s)-(−)-hyoscyamine
  • tropine-l-tropate
  • tropine-l-tropate
  • tropine tropate
  • tropine tropate
  • tropine tropate

Clinical trials

NCT IDPhaseStart dateSponsor(s)
NCT03750656Phase 4Nov 12, 2018University of Kansas
NCT02389998N/AJul 1, 2014Harvard University, Ohio State University
Showing 2 of 2 trials
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Organizations

Research & Development (3)

OrganizationOrg typeTrialsAs lead sponsorPhasesEarliest year
Harvard UniversityAcademic/Hospital1112014
Ohio State UniversityAcademic/Hospital1012014
University of KansasAcademic/Hospital1112018
3 organizations
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