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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

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
Anticholinergic poisoning from a large dose of Scopolia extract.
2002 Aug
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
Tropane alkaloids from Latua pubiflora.
2003 Sep-Oct
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
Structural and functional comparison of HemN to other radical SAM enzymes.
2005 Oct
Current gut-directed therapies for irritable bowel syndrome.
2006 Jul
How polyamine synthesis inhibitors and cinnamic acid affect tropane alkaloid production.
2007 Jan
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
Responses of fungi to tropane alkaloids produced by a medicinal plant Hyoscyamus muticus (Egyptian henbane).
2009
Screening pharmaceuticals for possible carcinogenic effects: initial positive results for drugs not previously screened.
2009 Dec
The symptomatic management of multiple sclerosis.
2009 Oct
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
Tropane alkaloid profiling of hydroponic Datura innoxia Mill. Plants inoculated with Agrobacterium rhizogenes.
2010 Jan-Feb
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
Enantiomeric differentiation of atropine/hyoscyamine by (13) C NMR spectroscopy and its application to Datura stramonium extract.
2010 Nov-Dec
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 Dec 15 15:18:24 GMT 2023
Edited
by admin
on Fri Dec 15 15:18:24 GMT 2023
Record UNII
PX44XO846X
Record Status Validated (UNII)
Record Version
  • Download
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
Related Record Type Details
RACEMATE -> ENANTIOMER
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SOLVATE->ANHYDROUS
BINDER->LIGAND
BINDING
SALT/SOLVATE -> PARENT
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PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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ACTIVE MOIETY
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Biological Half-life PHARMACOKINETIC