Details
Stereochemistry | ABSOLUTE |
Molecular Formula | 2C17H23NO3.2H2O.H2O4S |
Molecular Weight | 712.848 |
Optical Activity | ( - ) |
Defined Stereocenters | 8 / 8 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
O.O.OS(O)(=O)=O.CN1[C@H]2CC[C@@H]1C[C@@H](C2)OC(=O)[C@H](CO)C3=CC=CC=C3.CN4[C@H]5CC[C@@H]4C[C@@H](C5)OC(=O)[C@H](CO)C6=CC=CC=C6
InChI
InChIKey=BXSVDJUWKSRQMD-ITMJLNKNSA-N
InChI=1S/2C17H23NO3.H2O4S.2H2O/c2*1-18-13-7-8-14(18)10-15(9-13)21-17(20)16(11-19)12-5-3-2-4-6-12;1-5(2,3)4;;/h2*2-6,13-16,19H,7-11H2,1H3;(H2,1,2,3,4);2*1H2/t2*13-,14+,15+,16-;;;/m11.../s1
Molecular Formula | H2O |
Molecular Weight | 18.0153 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Molecular Formula | H2O4S |
Molecular Weight | 98.078 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
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 |
---|---|---|
Structural and functional comparison of HemN to other radical SAM enzymes. | 2005 Oct |
|
Tailoring tropane alkaloid accumulation in transgenic hairy roots of Atropa baetica by over-expressing the gene encoding hyoscyamine 6beta-hydroxylase. | 2006 Aug |
|
Immunolocalisation of two tropinone reductases in potato (Solanum tuberosum L.) root, stolon, and tuber sprouts. | 2006 Dec |
|
Tropinone reductases, enzymes at the branch point of tropane alkaloid metabolism. | 2006 Feb |
|
Constitutive and jasmonate-inducible traits of Datura wrightii. | 2006 Jan |
|
Current gut-directed therapies for irritable bowel syndrome. | 2006 Jul |
|
Studies on tropane alkaloid extraction by volatile organic solvents: dichloromethane vs. chloroform. | 2006 Mar-Apr |
|
Heterologous expression of Vitreoscilla hemoglobin (VHb) and cultivation conditions affect the alkaloid profile of Hyoscyamus muticus hairy roots. | 2006 Mar-Apr |
|
Functional genomic analysis of alkaloid biosynthesis in Hyoscyamus niger reveals a cytochrome P450 involved in littorine rearrangement. | 2006 May |
|
Self-amputation of penis and tongue after use of Angel's Trumpet. | 2006 Oct |
|
Comparison of glucagon and scopolamine butylbromide as premedication for colonoscopy in unsedated patients. | 2006 Sep |
|
The development of anticholinergics in the management of COPD. | 2007 |
|
Biotransformation of hyoscyamine into scopolamine in transgenic tobacco cell cultures. | 2007 Apr |
|
Tropane and nicotine alkaloid biosynthesis-novel approaches towards biotechnological production of plant-derived pharmaceuticals. | 2007 Aug |
|
How polyamine synthesis inhibitors and cinnamic acid affect tropane alkaloid production. | 2007 Jan |
|
Production of tropane alkaloids by small-scale bubble column bioreactor cultures of Scopolia parviflora adventitious roots. | 2007 Jul |
|
Tropane alkaloids production in transgenic Hyoscyamus niger hairy root cultures over-expressing putrescine N-methyltransferase is methyl jasmonate-dependent. | 2007 Mar |
|
HPLC-atmospheric pressure chemical ionization mass spectrometric method for enantioselective determination of R,S-propranolol and R,S-hyoscyamine in human plasma. | 2007 Nov 15 |
|
Evaluation of the cholinergic and adrenergic effects of two tropane alkaloids from Erythroxylum pervillei. | 2007 Oct |
|
Molecular cloning and characterization of a new cDNA encoding hyoscyamine 6beta-hydroxylase from roots of Anisodus acutangulus. | 2007 Sep 30 |
|
Endoscopic findings in loin pain hematuria syndrome: concentric clot in calyceal fornices. | 2008 |
|
Choice of antimuscarinic agents for overactive bladder in the older patient: focus on darifenacin. | 2008 |
|
[Determination of hyoscyamine and scopolamine in serum and urine of humans by liquid chromatography with tandem mass spectrometry]. | 2008 Aug |
|
The carbon-skeleton rearrangement in tropane alkaloid biosynthesis. | 2008 Aug 13 |
|
The scientific impact of microbial cell factories. | 2008 Dec 1 |
|
Treatment of pyridostigmine-induced AV block with hyoscyamine in a patient with myasthenia gravis. | 2008 Feb |
|
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 |
|
Synthesis and characterization of molecularly imprinted polymers for phenoxyacetic acids. | 2008 Jan |
|
Sublingual hyoscyamine spray as premedication for colonoscopy: a randomized double-blinded placebo-controlled trial. | 2008 Jul |
|
Characterization of Atropa belladonna L. compounds by capillary electrophoresis-electrospray ionization-time of flight-mass spectrometry and capillary electrophoresis-electrospray ionization-ion trap-mass spectrometry. | 2008 May |
|
Allosteric interaction of the anticholinergic drug [N-(4-phenyl)-phenacyl-l-hyoscyamine] (Phenthonium) with nicotinic receptors of post-ganglionic sympathetic neurons of the rat vas deferens. | 2009 Aug 15 |
|
Screening pharmaceuticals for possible carcinogenic effects: initial positive results for drugs not previously screened. | 2009 Dec |
|
Cloning, characterization and analysis of expression profiles of a cDNA encoding a hyoscyamine 6beta-hydroxylase (H6H) from Atropa baetica Willk. | 2009 Jan |
|
Assessment of the initial stability of the Symax femoral stem with EBRA-FCA: a multicentric study of 85 cases. | 2009 Jan-Mar |
|
Hyoscyamine biosynthesis in Datura stramonium hairy root in vitro systems with different ploidy levels. | 2009 May |
|
Yeast cell factory: fishing for the best one or engineering it? | 2009 Oct 12 |
|
"Divine stramonium": the rise and fall of smoking for asthma. | 2010 Apr |
|
Inappropriate prescribing in the hospitalized elderly patient: defining the problem, evaluation tools, and possible solutions. | 2010 Apr 7 |
|
An anesthetic experience with cesarean section in a patient with vasovagal syncope -A case report-. | 2010 Aug |
|
Hospice use and outcomes in nursing home residents with advanced dementia. | 2010 Dec |
|
Biochemical and structural characterization of recombinant hyoscyamine 6β-hydroxylase from Datura metel L. | 2010 Dec |
|
Cementless total hip replacement: a prospective clinical study of the early functional and radiological outcomes of three different hip stems. | 2010 Jan |
|
Tropane alkaloid profiling of hydroponic Datura innoxia Mill. Plants inoculated with Agrobacterium rhizogenes. | 2010 Jan-Feb |
|
An unusual case of anisocoria by vegetal intoxication: a case report. | 2010 Jul 20 |
|
DFT-GIAO(1)H NMR chemical shifts prediction for the spectral assignment and conformational analysis of the anticholinergic drugs (-)-scopolamine and (-)-hyoscyamine. | 2010 Jun |
|
Anisodamine production from natural sources: seedlings and hairy root cultures of Argentinean and Colombian Brugmansia candida plants. | 2010 Mar |
|
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 |
|
High-performance liquid-chromatographic tandem-mass spectrometric methods for atropinesterase-mediated enantioselective and chiral determination of R- and S-hyoscyamine in plasma. | 2010 Nov 8 |
|
Enantiomeric differentiation of atropine/hyoscyamine by (13) C NMR spectroscopy and its application to Datura stramonium extract. | 2010 Nov-Dec |
|
The pituri story: a review of the historical literature surrounding traditional Australian Aboriginal use of nicotine in Central Australia. | 2010 Sep 12 |
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
by
admin
on
Edited
Fri Dec 15 15:08:47 GMT 2023
by
admin
on
Fri Dec 15 15:08:47 GMT 2023
|
Record UNII |
F2R8V82B84
|
Record Status |
Validated (UNII)
|
Record Version |
|
-
Download
Name | Type | Language | ||
---|---|---|---|---|
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Brand Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Brand Name | English | ||
|
Common Name | English | ||
|
Brand Name | English | ||
|
Brand Name | English | ||
|
Common Name | English | ||
|
Brand Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Brand Name | English | ||
|
Brand Name | English | ||
|
Common Name | English |
Classification Tree | Code System | Code | ||
---|---|---|---|---|
|
NCI_THESAURUS |
C29704
Created by
admin on Fri Dec 15 15:08:48 GMT 2023 , Edited by admin on Fri Dec 15 15:08:48 GMT 2023
|
Code System | Code | Type | Description | ||
---|---|---|---|---|---|
|
6835-16-1
Created by
admin on Fri Dec 15 15:08:48 GMT 2023 , Edited by admin on Fri Dec 15 15:08:48 GMT 2023
|
PRIMARY | |||
|
1335009
Created by
admin on Fri Dec 15 15:08:48 GMT 2023 , Edited by admin on Fri Dec 15 15:08:48 GMT 2023
|
PRIMARY | |||
|
100000077629
Created by
admin on Fri Dec 15 15:08:48 GMT 2023 , Edited by admin on Fri Dec 15 15:08:48 GMT 2023
|
PRIMARY | |||
|
m6167
Created by
admin on Fri Dec 15 15:08:48 GMT 2023 , Edited by admin on Fri Dec 15 15:08:48 GMT 2023
|
PRIMARY | Merck Index | ||
|
CHEMBL1331216
Created by
admin on Fri Dec 15 15:08:48 GMT 2023 , Edited by admin on Fri Dec 15 15:08:48 GMT 2023
|
PRIMARY | |||
|
F2R8V82B84
Created by
admin on Fri Dec 15 15:08:48 GMT 2023 , Edited by admin on Fri Dec 15 15:08:48 GMT 2023
|
PRIMARY | |||
|
SUB14162MIG
Created by
admin on Fri Dec 15 15:08:48 GMT 2023 , Edited by admin on Fri Dec 15 15:08:48 GMT 2023
|
PRIMARY | |||
|
F2R8V82B84
Created by
admin on Fri Dec 15 15:08:48 GMT 2023 , Edited by admin on Fri Dec 15 15:08:48 GMT 2023
|
PRIMARY | |||
|
C74575
Created by
admin on Fri Dec 15 15:08:48 GMT 2023 , Edited by admin on Fri Dec 15 15:08:48 GMT 2023
|
PRIMARY | |||
|
1225
Created by
admin on Fri Dec 15 15:08:48 GMT 2023 , Edited by admin on Fri Dec 15 15:08:48 GMT 2023
|
PRIMARY | RxNorm | ||
|
DBSALT001011
Created by
admin on Fri Dec 15 15:08:48 GMT 2023 , Edited by admin on Fri Dec 15 15:08:48 GMT 2023
|
PRIMARY |
Related Record | Type | Details | ||
---|---|---|---|---|
|
ANHYDROUS->SOLVATE | |||
|
PARENT -> SALT/SOLVATE |
|
Related Record | Type | Details | ||
---|---|---|---|---|
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
|
||
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
|
||
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
|
||
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
|
||
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
|
||
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
|
||
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
|
Related Record | Type | Details | ||
---|---|---|---|---|
|
ACTIVE MOIETY |
|