Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C17H23NO3 |
Molecular Weight | 289.3694 |
Optical Activity | ( - ) |
Defined Stereocenters | 4 / 4 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CN1[C@H]2CC[C@@H]1C[C@@H](C2)OC(=O)[C@H](CO)C3=CC=CC=C3
InChI
InChIKey=RKUNBYITZUJHSG-FXUDXRNXSA-N
InChI=1S/C17H23NO3/c1-18-13-7-8-14(18)10-15(9-13)21-17(20)16(11-19)12-5-3-2-4-6-12/h2-6,13-16,19H,7-11H2,1H3/t13-,14+,15+,16-/m1/s1
Molecular Formula | C17H23NO3 |
Molecular Weight | 289.3694 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 4 / 4 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
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.
Approval Year
PubMed
Title | Date | PubMed |
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Anticholinergic poisoning from a large dose of Scopolia extract. | 2002 Aug |
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Biosynthetic studies on the tropane alkaloid hyoscyamine in Datura stramonium; hyoscyamine is stable to in vivo oxidation and is not derived from littorine via a vicinal interchange process. | 2002 Oct |
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Tropane alkaloids from Latua pubiflora. | 2003 Sep-Oct |
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A rapid densitometric method for the analysis of hyoscyamine and scopolamine in solanaceous plants and their transformed root cultures. | 2004 May-Jun |
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The history of barbiturates a century after their clinical introduction. | 2005 Dec |
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Structural and functional comparison of HemN to other radical SAM enzymes. | 2005 Oct |
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Current gut-directed therapies for irritable bowel syndrome. | 2006 Jul |
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How polyamine synthesis inhibitors and cinnamic acid affect tropane alkaloid production. | 2007 Jan |
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The scientific impact of microbial cell factories. | 2008 Dec 1 |
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Treatment of pyridostigmine-induced AV block with hyoscyamine in a patient with myasthenia gravis. | 2008 Feb |
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A study of the teratogenic and fetotoxic effects of large doses of barbital, hexobarbital and butobarbital used for suicide attempts by pregnant women. | 2008 Feb-Mar |
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Responses of fungi to tropane alkaloids produced by a medicinal plant Hyoscyamus muticus (Egyptian henbane). | 2009 |
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Screening pharmaceuticals for possible carcinogenic effects: initial positive results for drugs not previously screened. | 2009 Dec |
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The symptomatic management of multiple sclerosis. | 2009 Oct |
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An anesthetic experience with cesarean section in a patient with vasovagal syncope -A case report-. | 2010 Aug |
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Hospice use and outcomes in nursing home residents with advanced dementia. | 2010 Dec |
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Tropane alkaloid profiling of hydroponic Datura innoxia Mill. Plants inoculated with Agrobacterium rhizogenes. | 2010 Jan-Feb |
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Optimization of the culture medium composition to improve the production of hyoscyamine in elicited Datura stramonium L. hairy roots using the Response Surface Methodology (RSM). | 2010 Nov 18 |
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Enantiomeric differentiation of atropine/hyoscyamine by (13) C NMR spectroscopy and its application to Datura stramonium extract. | 2010 Nov-Dec |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.rxlist.com/levsin-drug.htm#dosage
1 to 2 tablets (0.125 mg) every four hours or as needed. Do not exceed 12 tablets in 24 hours.
Route of Administration:
Oral
Substance Class |
Chemical
Created
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Record UNII |
PX44XO846X
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Validated (UNII)
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Classification Tree | Code System | Code | ||
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WHO-VATC |
QA03CB31
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WHO-ATC |
A03CB31
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LIVERTOX |
NBK548870
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WHO-ATC |
A03BA03
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WHO-VATC |
QA03BA03
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NCI_THESAURUS |
C29704
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PX44XO846X
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757064
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58164
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PX44XO846X
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1402
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SUB14160MIG
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153970
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HYOSCYAMINE
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100000077628
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3552
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C29104
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CHEMBL1331216
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DB00424
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101-31-5
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202-933-0
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17486
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m6167
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PRIMARY | Merck Index |
Related Record | Type | Details | ||
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RACEMATE -> ENANTIOMER | |||
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SALT/SOLVATE -> PARENT |
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SALT/SOLVATE -> PARENT |
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SOLVATE->ANHYDROUS | |||
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BINDER->LIGAND |
BINDING
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SALT/SOLVATE -> PARENT |
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Related Record | Type | Details | ||
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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Related Record | Type | Details | ||
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ACTIVE MOIETY |
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Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Biological Half-life | PHARMACOKINETIC |
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