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Details

Stereochemistry ABSOLUTE
Molecular Formula 2C17H23NO3.2H2O.H2O4S
Molecular Weight 712.8503
Optical Activity UNSPECIFIED
Defined Stereocenters 6 / 6
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of HYOSCYAMINE SULFATE

SMILES

CN1[C@]2([H])CC[C@@]1([H])C[C@]([H])(C2)OC(=O)[C@]([H])(CO)c3ccccc3.CN1[C@]2([H])CC[C@@]1([H])C[C@]([H])(C2)OC(=O)[C@]([H])(CO)c3ccccc3.OS(=O)(=O)O.O.O

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

HIDE SMILES / InChI

Molecular Formula C17H23NO3
Molecular Weight 289.3701
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 3 / 3
E/Z Centers 0
Optical Activity UNSPECIFIED

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 98.0796
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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

Targets

Targets

Primary TargetPharmacologyConditionPotency
7.5 nM [IC50]
PubMed

PubMed

TitleDatePubMed
The history of barbiturates a century after their clinical introduction.
2005 Dec
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
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
Nocturnal enuresis.
2007 Oct 1
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
Neurogenic bladder: etiology and assessment.
2008 Apr
[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
Effect of chromium species on phytochemical and physiological parameters in Datura innoxia.
2008 Jun
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
Expression of Brugmansia candida Hyoscyamine 6beta-Hydroxylase gene in Saccharomyces cerevisiae and its potential use as biocatalyst.
2008 May 27
Responses of fungi to tropane alkaloids produced by a medicinal plant Hyoscyamus muticus (Egyptian henbane).
2009
Molecular cloning and mRNA expression profiling of the first specific jasmonate biosynthetic pathway gene allene oxide synthase from Hyoscyamus niger.
2009 Apr
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
The symptomatic management of multiple sclerosis.
2009 Oct
Yeast cell factory: fishing for the best one or engineering it?
2009 Oct 12
Molecular cloning and characterization of two tropinone reductases in Anisodus acutangulus and enhancement of tropane alkaloid production in AaTRI-transformed hairy roots.
2009 Oct 23
Mechanistic insights into the cytochrome P450-mediated oxidation and rearrangement of littorine in tropane alkaloid biosynthesis.
2009 Sep 21
"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
Production of tropane alkaloids during de-differentiation of Scopolia parviflora calli.
2010 Feb 26
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
Differential production of tropane alkaloids in hairy roots and in vitro cultured two accessions of Atropa belladonna L. under nitrate treatments.
2010 May-Jun
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
Patents

Sample Use Guides

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 Fri Jun 25 21:11:16 UTC 2021
Edited
by admin
on Fri Jun 25 21:11:16 UTC 2021
Record UNII
F2R8V82B84
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
HYOSCYAMINE SULFATE
EP   MART.   USP   USP-RS   VANDF   WHO-DD  
Common Name English
HYOSCYAMINE SULFATE [USP]
Common Name English
HYOSCYAMINE SULFATE [USP-RS]
Common Name English
1.ALPHA.H,5.ALPHA.H-TROPAN-3.ALPHA.-OL (-)-TROPATE (ESTER) SULFATE (2:1) (SALT) DIHYDRATE
Common Name English
LEVSINEX
Brand Name English
HYOSCYAMINE SULFATE [MART.]
Common Name English
BENZENEACETIC ACID, .ALPHA.-(HYDROXYMETHYL)-, 8-METHYL-8-AZABICYCLO(3.2.1)OCT-3-YL ESTER, (3(S)-ENDO)-, SULFATE (2:1), DIHYDRATE
Common Name English
NEOQUESS
Brand Name English
HYOSCYAMINE SULPHATE
Common Name English
LEVSIN
Brand Name English
ANASPAZ
Brand Name English
HYOSCYAMINE SULFATE [VANDF]
Common Name English
HYOSCYAMINE SULFATE [WHO-DD]
Common Name English
PEPTARD
Brand Name English
HYOSCYAMINE SULFATE DIHYDRATE [MART.]
Common Name English
HYOSCYAMINE SULFATE [EP MONOGRAPH]
Common Name English
EGAZIL DURETTER
Brand Name English
EGACENE
Brand Name English
HYOSCYAMINE SULFATE DIHYDRATE [MI]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C29704
Created by admin on Fri Jun 25 21:11:16 UTC 2021 , Edited by admin on Fri Jun 25 21:11:16 UTC 2021
Code System Code Type Description
CAS
6835-16-1
Created by admin on Fri Jun 25 21:11:16 UTC 2021 , Edited by admin on Fri Jun 25 21:11:16 UTC 2021
PRIMARY
MERCK INDEX
M6167
Created by admin on Fri Jun 25 21:11:16 UTC 2021 , Edited by admin on Fri Jun 25 21:11:16 UTC 2021
PRIMARY Merck Index
ChEMBL
CHEMBL1331216
Created by admin on Fri Jun 25 21:11:16 UTC 2021 , Edited by admin on Fri Jun 25 21:11:16 UTC 2021
PRIMARY
FDA UNII
F2R8V82B84
Created by admin on Fri Jun 25 21:11:16 UTC 2021 , Edited by admin on Fri Jun 25 21:11:16 UTC 2021
PRIMARY
EVMPD
SUB14162MIG
Created by admin on Fri Jun 25 21:11:16 UTC 2021 , Edited by admin on Fri Jun 25 21:11:16 UTC 2021
PRIMARY
NCI_THESAURUS
C74575
Created by admin on Fri Jun 25 21:11:16 UTC 2021 , Edited by admin on Fri Jun 25 21:11:16 UTC 2021
PRIMARY
USP_CATALOG
1335009
Created by admin on Fri Jun 25 21:11:16 UTC 2021 , Edited by admin on Fri Jun 25 21:11:16 UTC 2021
PRIMARY USP-RS
RXCUI
1225
Created by admin on Fri Jun 25 21:11:16 UTC 2021 , Edited by admin on Fri Jun 25 21:11:16 UTC 2021
PRIMARY RxNorm
DRUG BANK
DBSALT001011
Created by admin on Fri Jun 25 21:11:16 UTC 2021 , Edited by admin on Fri Jun 25 21:11:16 UTC 2021
PRIMARY
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PARENT -> SALT/SOLVATE
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CHROMATOGRAPHIC PURITY (HPLC/UV)
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IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
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IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
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IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
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IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
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IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
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IMPURITY -> PARENT
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ACTIVE MOIETY