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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
Structure of HYOSCYAMINE SULFATE

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

HIDE SMILES / InChI

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

Targets

Targets

Primary TargetPharmacologyConditionPotency
7.5 nM [IC50]
PubMed

PubMed

TitleDatePubMed
Distribution of hyoscyamine and scopolamine in Datura stramonium.
2001 Aug
Constitutive inhibitory action of muscarinic receptors on adenylyl cyclase in cardiac membranes and its stereospecific suppression by hyoscyamine.
2002
Molecular cloning, expression and characterization of tropinone reductase II, an enzyme of the SDR family in Solanum tuberosum (L.).
2002 Feb 1
Urinary antispasmodic use and the risks of ventricular arrhythmia and sudden death in older patients.
2002 Jan
Alkaloid spectrum in diploid and tetraploid hairy root cultures of Datura stramonium.
2003 Jan-Feb
Tropane alkaloids from Latua pubiflora.
2003 Sep-Oct
Fatal poisoning from ingestion of Datura stramonium seeds.
2004 Apr
A rapid densitometric method for the analysis of hyoscyamine and scopolamine in solanaceous plants and their transformed root cultures.
2004 May-Jun
The history of barbiturates a century after their clinical introduction.
2005 Dec
Identification and estimation of the levo isomer in raw materials and finished products containing atropine and/or hyoscyamine.
2005 Jan-Feb
Conductimetric determination of phenylpropanolamine HCl, ranitidine HCl, hyoscyamine HBr and betaine HCl in their pure state and pharmaceutical preparations.
2005 Jun-Jul
Molecular cloning, expression and characterization of hyoscyamine 6beta-hydroxylase from hairy roots of Anisodus tanguticus.
2005 Mar
Post-marketing surveillance using pharmacy-based cohorts: results of a pilot study.
2005 May
Structural and functional comparison of HemN to other radical SAM enzymes.
2005 Oct
Pharmacokinetics and pharmacodynamics in clinical use of scopolamine.
2005 Oct
Enhanced secretion of tropane alkaloids in Nicotiana tabacum hairy roots expressing heterologous hyoscyamine-6beta-hydroxylase.
2005 Oct
Simultaneous analysis of hyoscyamine, scopolamine, 6beta-hydroxyhyoscyamine and apoatropine in Solanaceous hairy roots by reversed-phase high-performance liquid chromatography.
2005 Oct 14
PVC membrane ion-selective electrodes for the determination of Hyoscyamine in pure solution and in pharmaceutical preparations under batch and flow modes.
2005 Sep 1
Tailoring tropane alkaloid accumulation in transgenic hairy roots of Atropa baetica by over-expressing the gene encoding hyoscyamine 6beta-hydroxylase.
2006 Aug
Constitutive and jasmonate-inducible traits of Datura wrightii.
2006 Jan
Putrescine N-methyltransferase in Solanum tuberosum L., a calystegine-forming plant.
2006 Jan
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
The development of anticholinergics in the management of COPD.
2007
Production of tropane alkaloids by small-scale bubble column bioreactor cultures of Scopolia parviflora adventitious roots.
2007 Jul
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
Nocturnal enuresis.
2007 Oct 1
Endoscopic findings in loin pain hematuria syndrome: concentric clot in calyceal fornices.
2008
Reasons for noncompliance with five-yearly screening flexible sigmoidoscopy.
2008 Feb 2
Synthesis and characterization of molecularly imprinted polymers for phenoxyacetic acids.
2008 Jan
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
Assessment of the initial stability of the Symax femoral stem with EBRA-FCA: a multicentric study of 85 cases.
2009 Jan-Mar
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
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
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
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 Wed Jul 05 22:40:43 UTC 2023
Edited
by admin
on Wed Jul 05 22:40:43 UTC 2023
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-RS]
Common Name English
1.ALPHA.H,5.ALPHA.H-TROPAN-3.ALPHA.-OL (-)-TROPATE (ESTER) SULFATE (2:1) (SALT) DIHYDRATE
Common Name English
Hyoscyamine sulfate [WHO-DD]
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
HYOSCYAMINE SULFATE [USP MONOGRAPH]
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
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 Wed Jul 05 22:40:43 UTC 2023 , Edited by admin on Wed Jul 05 22:40:43 UTC 2023
Code System Code Type Description
CAS
6835-16-1
Created by admin on Wed Jul 05 22:40:43 UTC 2023 , Edited by admin on Wed Jul 05 22:40:43 UTC 2023
PRIMARY
RS_ITEM_NUM
1335009
Created by admin on Wed Jul 05 22:40:43 UTC 2023 , Edited by admin on Wed Jul 05 22:40:43 UTC 2023
PRIMARY
SMS_ID
100000077629
Created by admin on Wed Jul 05 22:40:43 UTC 2023 , Edited by admin on Wed Jul 05 22:40:43 UTC 2023
PRIMARY
MERCK INDEX
M6167
Created by admin on Wed Jul 05 22:40:43 UTC 2023 , Edited by admin on Wed Jul 05 22:40:43 UTC 2023
PRIMARY Merck Index
ChEMBL
CHEMBL1331216
Created by admin on Wed Jul 05 22:40:43 UTC 2023 , Edited by admin on Wed Jul 05 22:40:43 UTC 2023
PRIMARY
FDA UNII
F2R8V82B84
Created by admin on Wed Jul 05 22:40:43 UTC 2023 , Edited by admin on Wed Jul 05 22:40:43 UTC 2023
PRIMARY
EVMPD
SUB14162MIG
Created by admin on Wed Jul 05 22:40:43 UTC 2023 , Edited by admin on Wed Jul 05 22:40:43 UTC 2023
PRIMARY
DAILYMED
F2R8V82B84
Created by admin on Wed Jul 05 22:40:43 UTC 2023 , Edited by admin on Wed Jul 05 22:40:43 UTC 2023
PRIMARY
NCI_THESAURUS
C74575
Created by admin on Wed Jul 05 22:40:43 UTC 2023 , Edited by admin on Wed Jul 05 22:40:43 UTC 2023
PRIMARY
RXCUI
1225
Created by admin on Wed Jul 05 22:40:43 UTC 2023 , Edited by admin on Wed Jul 05 22:40:43 UTC 2023
PRIMARY RxNorm
DRUG BANK
DBSALT001011
Created by admin on Wed Jul 05 22:40:43 UTC 2023 , Edited by admin on Wed Jul 05 22:40:43 UTC 2023
PRIMARY
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