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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
Structure of HYOSCYAMINE

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

HIDE SMILES / InChI
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
Tropane alkaloid production by shoot culture of Duboisia myoporoides R. Br.
2001 Jan
Urinary antispasmodic use and the risks of ventricular arrhythmia and sudden death in older patients.
2002 Jan
Warm water irrigation for dealing with spasm during colonoscopy: simple, inexpensive, and effective.
2002 Nov
Alkaloids in plants and root cultures of Atropa belladonna overexpressing putrescine N-methyltransferase.
2003 Sep
A rapid densitometric method for the analysis of hyoscyamine and scopolamine in solanaceous plants and their transformed root cultures.
2004 May-Jun
Rapid in vitro adventitious shoot propagation of Scopolia parviflora through rhizome cultures for enhanced production of tropane alkaloids.
2004 Sep
The history of barbiturates a century after their clinical introduction.
2005 Dec
Expression of Vitreoscilla hemoglobin enhances growth of Hyoscyamus muticus hairy root cultures.
2005 Jan
Conductimetric determination of phenylpropanolamine HCl, ranitidine HCl, hyoscyamine HBr and betaine HCl in their pure state and pharmaceutical preparations.
2005 Jun-Jul
Post-marketing surveillance using pharmacy-based cohorts: results of a pilot study.
2005 May
Pharmacokinetics and pharmacodynamics in clinical use of scopolamine.
2005 Oct
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
Biotransformation of hyoscyamine into scopolamine in transgenic tobacco cell cultures.
2007 Apr
How polyamine synthesis inhibitors and cinnamic acid affect tropane alkaloid production.
2007 Jan
Endoscopic findings in loin pain hematuria syndrome: concentric clot in calyceal fornices.
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
Reasons for noncompliance with five-yearly screening flexible sigmoidoscopy.
2008 Feb 2
Sublingual hyoscyamine spray as premedication for colonoscopy: a randomized double-blinded placebo-controlled trial.
2008 Jul
Assessment of the initial stability of the Symax femoral stem with EBRA-FCA: a multicentric study of 85 cases.
2009 Jan-Mar
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
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
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
Name Type Language
HYOSCYAMINE
HSDB   MART.   MI   USP   VANDF   WHO-DD  
Common Name English
L-TROPIC ACID ESTER WITH TROPINE
Brand Name English
(S)-(-)-HYOSCYAMINE
Common Name English
HYOSCYAMINE [VANDF]
Common Name English
BELLAFOLINE
Brand Name English
Hyoscyamine [WHO-DD]
Common Name English
ATROPINE, (S)-
Common Name English
HYOSCYAMINUM
HPUS  
Common Name English
HYOSCYAMINE [MI]
Common Name English
BENZENEACETIC ACID, .ALPHA.-(HYDROXYMETHYL)-, (3-ENDO)-8-METHYL-8-AZABICYCLO(3.2.1)OCT-3-YL ESTER, (.ALPHA.S)-
Systematic Name English
(-)-ATROPINE
Common Name English
(-)-HYOSCYAMINE
Common Name English
HYOSCYAMINUM [HPUS]
Common Name English
L-HYOSCYAMINE
Common Name English
NSC-757064
Code English
DATURINE
Common Name English
HYOSCYAMINE [MART.]
Common Name English
HYOSCYAMINE [USP MONOGRAPH]
Common Name English
CYSTOSPAZ
Brand Name English
HYOSCYAMINE [HSDB]
Common Name English
DUBOISINE
Common Name English
Classification Tree Code System Code
WHO-VATC QA03CB31
Created by admin on Fri Dec 15 15:18:25 GMT 2023 , Edited by admin on Fri Dec 15 15:18:25 GMT 2023
WHO-ATC A03CB31
Created by admin on Fri Dec 15 15:18:25 GMT 2023 , Edited by admin on Fri Dec 15 15:18:25 GMT 2023
LIVERTOX NBK548870
Created by admin on Fri Dec 15 15:18:25 GMT 2023 , Edited by admin on Fri Dec 15 15:18:25 GMT 2023
WHO-ATC A03BA03
Created by admin on Fri Dec 15 15:18:25 GMT 2023 , Edited by admin on Fri Dec 15 15:18:25 GMT 2023
WHO-VATC QA03BA03
Created by admin on Fri Dec 15 15:18:25 GMT 2023 , Edited by admin on Fri Dec 15 15:18:25 GMT 2023
NCI_THESAURUS C29704
Created by admin on Fri Dec 15 15:18:25 GMT 2023 , Edited by admin on Fri Dec 15 15:18:25 GMT 2023
Code System Code Type Description
FDA UNII
PX44XO846X
Created by admin on Fri Dec 15 15:18:25 GMT 2023 , Edited by admin on Fri Dec 15 15:18:25 GMT 2023
PRIMARY
NSC
757064
Created by admin on Fri Dec 15 15:18:25 GMT 2023 , Edited by admin on Fri Dec 15 15:18:25 GMT 2023
PRIMARY
CHEBI
58164
Created by admin on Fri Dec 15 15:18:25 GMT 2023 , Edited by admin on Fri Dec 15 15:18:25 GMT 2023
PRIMARY
DAILYMED
PX44XO846X
Created by admin on Fri Dec 15 15:18:25 GMT 2023 , Edited by admin on Fri Dec 15 15:18:25 GMT 2023
PRIMARY
DRUG CENTRAL
1402
Created by admin on Fri Dec 15 15:18:25 GMT 2023 , Edited by admin on Fri Dec 15 15:18:25 GMT 2023
PRIMARY
EVMPD
SUB14160MIG
Created by admin on Fri Dec 15 15:18:25 GMT 2023 , Edited by admin on Fri Dec 15 15:18:25 GMT 2023
PRIMARY
RXCUI
153970
Created by admin on Fri Dec 15 15:18:25 GMT 2023 , Edited by admin on Fri Dec 15 15:18:25 GMT 2023
PRIMARY RxNorm
WIKIPEDIA
HYOSCYAMINE
Created by admin on Fri Dec 15 15:18:25 GMT 2023 , Edited by admin on Fri Dec 15 15:18:25 GMT 2023
PRIMARY
SMS_ID
100000077628
Created by admin on Fri Dec 15 15:18:25 GMT 2023 , Edited by admin on Fri Dec 15 15:18:25 GMT 2023
PRIMARY
EPA CompTox
DTXSID80889335
Created by admin on Fri Dec 15 15:18:25 GMT 2023 , Edited by admin on Fri Dec 15 15:18:25 GMT 2023
PRIMARY
HSDB
3552
Created by admin on Fri Dec 15 15:18:25 GMT 2023 , Edited by admin on Fri Dec 15 15:18:25 GMT 2023
PRIMARY
NCI_THESAURUS
C29104
Created by admin on Fri Dec 15 15:18:25 GMT 2023 , Edited by admin on Fri Dec 15 15:18:25 GMT 2023
PRIMARY
ChEMBL
CHEMBL1331216
Created by admin on Fri Dec 15 15:18:25 GMT 2023 , Edited by admin on Fri Dec 15 15:18:25 GMT 2023
PRIMARY
DRUG BANK
DB00424
Created by admin on Fri Dec 15 15:18:25 GMT 2023 , Edited by admin on Fri Dec 15 15:18:25 GMT 2023
PRIMARY
CAS
101-31-5
Created by admin on Fri Dec 15 15:18:25 GMT 2023 , Edited by admin on Fri Dec 15 15:18:25 GMT 2023
PRIMARY
ECHA (EC/EINECS)
202-933-0
Created by admin on Fri Dec 15 15:18:25 GMT 2023 , Edited by admin on Fri Dec 15 15:18:25 GMT 2023
PRIMARY
CHEBI
17486
Created by admin on Fri Dec 15 15:18:25 GMT 2023 , Edited by admin on Fri Dec 15 15:18:25 GMT 2023
PRIMARY
MERCK INDEX
m6167
Created by admin on Fri Dec 15 15:18:25 GMT 2023 , Edited by admin on Fri Dec 15 15:18:25 GMT 2023
PRIMARY Merck Index