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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
Decreased scopolamine yield in field-grown Duboisia plants regenerated from hairy roots.
2001 Apr
Occurrence of cadaverine in hairy roots of Brugmansia candida.
2001 Jul
Tropane alkaloids in auxin-independent root cultures of Physochlaina physaloides.
2002
Constitutive inhibitory action of muscarinic receptors on adenylyl cyclase in cardiac membranes and its stereospecific suppression by hyoscyamine.
2002
Kinetic study of littorine rearrangement in Datura innoxia hairy roots by (13)C NMR spectroscopy.
2002 Aug
Anticholinergic poisoning from a large dose of Scopolia extract.
2002 Aug
Warm water irrigation for dealing with spasm during colonoscopy: simple, inexpensive, and effective.
2002 Nov
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
Alkaloid spectrum in diploid and tetraploid hairy root cultures of Datura stramonium.
2003 Jan-Feb
Alkaloids of Datura ceratocaula.
2003 Jul-Aug
Alkaloids in plants and root cultures of Atropa belladonna overexpressing putrescine N-methyltransferase.
2003 Sep
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
Induction of tropane alkaloid formation in transformed root cultures of Brugmansia suaveolens (Solanaceae).
2004 Nov-Dec
Rapid in vitro adventitious shoot propagation of Scopolia parviflora through rhizome cultures for enhanced production of tropane alkaloids.
2004 Sep
Expression of Vitreoscilla hemoglobin enhances growth of Hyoscyamus muticus hairy root cultures.
2005 Jan
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
Structural and functional comparison of HemN to other radical SAM enzymes.
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
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
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
Self-amputation of penis and tongue after use of Angel's Trumpet.
2006 Oct
The development of anticholinergics in the management of COPD.
2007
Tropane and nicotine alkaloid biosynthesis-novel approaches towards biotechnological production of plant-derived pharmaceuticals.
2007 Aug
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
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
The carbon-skeleton rearrangement in tropane alkaloid biosynthesis.
2008 Aug 13
The scientific impact of microbial cell factories.
2008 Dec 1
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
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
The symptomatic management of multiple sclerosis.
2009 Oct
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
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
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 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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IMPURITY -> PARENT
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ACTIVE MOIETY