Hyoscyamine

Identification

Summary

Hyoscyamine is an anticholinergic indicated to treat functional gastrointestinal disorders, biliary and renal colic, and acute rhinitis.

Brand Names
Anaspaz, Donnatal, Ed Spaz, Hyophen, Levbid, Levsin, Nulev, Oscimin, Phenohytro, Phosphasal, Symax, Urelle, Uribel, Urimar Reformulated Oct 2013, Urin DS, Urogesic Blue Reformulated Apr 2012, Ustell, Utira
Generic Name
Hyoscyamine
DrugBank Accession Number
DB00424
Background

Hyoscyamine is a tropane alkaloid and the levo-isomer of atropine.2 It is commonly extracted from plants in the Solanaceae or nightshade family.2 Research into the action of hyoscyamine in published literature dates back to 1826.6 Hyoscyamine is used for a wide variety of treatments and therapeutics due to its antimuscarinic properties.7,8

Although hyoscyamine is marketed in the United States, it is not FDA approved.7,8

Type
Small Molecule
Groups
Approved
Structure
Thumb
Weight
Average: 289.3694
Monoisotopic: 289.167793607
Chemical Formula
C17H23NO3
Synonyms
  • (−)-atropine
  • (−)-hyoscyamine
  • (S)-(−)-hyoscyamine
  • (S)-atropine
  • [3(S)-endo]-α-(hydroxymethyl)benzeneacetic acid 8-methyl-8-azabicyclo[3.2.1]oct-3-yl ester
  • Daturin
  • Daturine
  • Duboisine
  • Hyoscyamin
  • Hyoscyamine
  • Hyoscyaminum
  • L-Hyoscyamine
  • L-Tropine tropate
  • Tropine-L-tropate

Pharmacology

Indication

As a drug that is not FDA approved, hyscyamine has no official indications.7,8 Intravenous hysocyamine has been used to reduce gastric motility, reduce pancreatic pain and secretions, to facilitate imaging of the gastrointestinal tract, treat anticholinesterase toxicity, treat certain cases of partial heart block, improve visualization of the kidneys, and for symptomatic relief of biliary and renal colic.7 Intravenous hyoscyamine is also used pre-operatively to reduce secretions of the mouth and respiratory tract to facilitate intubation.7 Oral hyoscyamine is used to treat functional intestinal disorders, for symptomatic relief of biliary and renal colic, and symptomatic relief of acute rhinitis.8

Pharmacology
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Associated Conditions
Contraindications & Blackbox Warnings
Contraindications
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Pharmacodynamics

Hyoscyamine is not FDA approved, and so it has not official indications.7,8 However, it is used as an antimuscarinic agent in a number of treatments and therapies.7,8 Hyoscyamine has a short duration of action as it may need to be given multiple times per day.7,8 Patients should be counselled regarding the risks and signs of anticholinergic toxicity.7,8

Mechanism of action

Hyoscyamine competitively and non-selectively antagonises muscarinic receptors in the smooth muscle, cardiac muscle, sino-atrial node, atrioventricular node, exocrine nodes, gastrointestinal tract, and respiratory tract.3,7,8 Antagonism of muscarinic M1, M4, and M5 receptors in the central nervous system lead to cognitive impairment; antagonism of M2 in the sinoatrial and atrioventricular nodes leads to bradycardia and lowers contractility; and antagonism of M3 in smooth muscle results in reduced peristalsis, bladder contraction, salivary secretions, gastric secretions, bronchial secretions, sweating, increased bronchodilation, mydriasis, and cycloplegia.3,4,5

TargetActionsOrganism
AMuscarinic acetylcholine receptor M1
antagonist
Humans
AMuscarinic acetylcholine receptor M2
antagonist
Humans
UMuscarinic acetylcholine receptor M3
antagonist
Humans
UMuscarinic acetylcholine receptor M4
antagonist
Humans
UAdenylate cyclase type 1
inhibitor
Humans
Absorption

Hyoscyamine is completely absorbed by sublingual and oral routes, though exact data regarding the Cmax, Tmax, and AUC are not readily available.7,8

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism

Hyoscyamine is largely unmetabolized, however a small amount is hydrolyzed into tropine and tropic acid.1,8

Hover over products below to view reaction partners

Route of elimination

The majority of hyoscyamine is eliminated in the urine as the unmetabolized parent compound.7,8

Half-life

The half life of hyoscyamine is 3.5 hours.7,8

Clearance

Not Available

Adverse Effects
Adverseeffects
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Toxicity

Patients experiencing an overdose may present with headache, nausea, vomiting, dizziness, dry mouth, difficulty in swallowing, dilated pupils, blurred vision, urinary retention, hot dry and flushed skin, tachycardia, hypertension, hypotension, respiratory depression, CNS stimulation, fever, ataxia, excitation, lethargy, stupor, coma, and paralysis.7,8 Patients should be treated with symptomatic and supportive therapy which may include emesis, gastric lavage, activated charcoal, artificial respiration, or intravenous physostigmine.2,7,8 Dialysis is expected to remove hyoscyamine sulfate from circulation.7,8

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
1,2-Benzodiazepine1,2-Benzodiazepine may increase the central nervous system depressant (CNS depressant) activities of Hyoscyamine.
AcebutololHyoscyamine may increase the arrhythmogenic activities of Acebutolol.
AcetazolamideAcetazolamide may increase the central nervous system depressant (CNS depressant) activities of Hyoscyamine.
AcetophenazineAcetophenazine may increase the anticholinergic activities of Hyoscyamine.
AcetyldigitoxinHyoscyamine may increase the arrhythmogenic activities of Acetyldigitoxin.
AclidiniumThe risk or severity of adverse effects can be increased when Hyoscyamine is combined with Aclidinium.
AcrivastineAcrivastine may increase the anticholinergic activities of Hyoscyamine.
AdenosineHyoscyamine may increase the arrhythmogenic activities of Adenosine.
AgomelatineAgomelatine may increase the central nervous system depressant (CNS depressant) activities of Hyoscyamine.
AjmalineHyoscyamine may increase the arrhythmogenic activities of Ajmaline.
Interactions
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Food Interactions
  • Take before a meal. Take 30-60 minutes before a meal.
  • Take separate from antacids. Take oral hyoscyamine before meals and antacids after meals.

Products

Products2
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Product Ingredients
IngredientUNIICASInChI Key
Hyoscyamine hydrobromideIWT50P9S79306-03-6VZDNSFSBCMCXSK-PGQIENJJSA-N
Hyoscyamine sulfateOB570Z127K620-61-1Not applicable
Hyoscyamine sulfate dihydrateF2R8V82B846835-16-1BXSVDJUWKSRQMD-ITMJLNKNSA-N
Product Images
International/Other Brands
Acupaz (Glitz) / Anapaz (Hilton) / Atropen / Boots Travel Calm (Boots) / Buwecon (Yung Shin) / Cystospaz / Cytospaz (Amerifit) / Donnamar / Egazil (BioPhausia) / Levsinex / Symax (Capellon)
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
AnaspazTablet, orally disintegrating0.125 mg/1Oral; SublingualPhysicians Total Care, Inc.1973-01-022011-06-30US flag
AnaspazTablet, orally disintegrating0.125 mg/1Oral; SublingualBF ASCHER AND CO INC1973-01-02Not applicableUS flag
Ed-spazTablet, orally disintegrating0.125 mg/1OralEDWARDS PHARMACEUTICALS, INC.2010-05-12Not applicableUS flag
HyoMaxTablet.125 mg/1OralAristos Phamaceuticals, Inc.2009-10-082010-12-31US flag
HyoMax-DTTablet0.375 mg/1OralAristos Phamaceuticals, Inc.2008-07-192012-10-31US flag24486 060420210423 11582 1p941j9
HyoMax-FTTablet.125 mg/1OralAristos Phamaceuticals, Inc.2008-06-192011-03-28US flag24486 060320210311 21055 1xzwqox
HyoMax-SLTablet.125 mg/1OralAristos Phamaceuticals, Inc.2008-05-282013-10-31US flag24486 060120210427 24843 2vqs83
HyoMax-SRTablet0.375 mg/1OralAristos Phamaceuticals, Inc.2008-06-132012-09-30US flag
HyoscyamineLiquid0.125 mg/5mLOralPatrin Pharma2011-09-04Not applicableUS flag
HyoscyamineTablet, extended release0.375 mg/1OralSeton Pharmaceuticals2009-10-232011-12-01US flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Calmitol Itching Relief OntHyoscyamine (.0001 %) + Camphor (.62 %) + Chloral hydrate (.496 %) + Levomenthol (.58 %) + Zinc oxide (12.5 %)OintmentTopicalPfizer Canada Inc., Consumer Healthcare Division1964-12-311996-09-09Canada flag
Diban CapHyoscyamine sulfate (0.0519 mg) + Atropine sulfate anyhdrous (9.7 mcg) + Attapulgite (300 mg) + Opium (12 mg) + Pectin (71.4 mg) + Scopolamine (3.3 mcg)CapsuleOralWyeth Ayerst Canada Inc.1998-02-182001-01-30Canada flag
Diban CapHyoscyamine sulfate (0.0519 mg) + Atropine sulfate anyhdrous (9.7 mcg) + Attapulgite (300 mg) + Opium (12 mg) + Pectin (71.4 mg) + Scopolamine (3.3 mcg)CapsuleOralAyerst Laboratories1992-12-311999-04-12Canada flag
Donnagel LiqHyoscyamine sulfate (0.1037 mg) + Atropine sulfate anyhdrous (0.0194 mg) + Kaolin (6 g) + Pectin (142.8 mg) + Scopolamine (6.5 mcg)LiquidOralAyerst Laboratories1993-12-311996-09-10Canada flag
Donnagel LiqHyoscyamine sulfate (0.1037 mg) + Atropine sulfate anyhdrous (0.0194 mg) + Kaolin (6 g) + Pectin (142.8 mg) + Scopolamine (6.5 mcg)LiquidOralWyeth Ayerst Canada Inc.1995-12-311997-08-14Canada flag
Donnatal ElixirHyoscyamine sulfate (0.1037 mg) + Atropine sulfate anyhdrous (0.0194 mg) + Phenobarbital (16.2 mg) + Scopolamine (6.5 mcg)ElixirOralWyeth Ayerst Canada Inc.1994-12-312001-01-16Canada flag
Donnatal ElixirHyoscyamine sulfate (0.1037 mg) + Atropine sulfate anyhdrous (0.0194 mg) + Phenobarbital (16.2 mg) + Scopolamine (6.5 mcg)ElixirOralAyerst Laboratories1991-12-311996-09-10Canada flag
Donnatal ExtentabsHyoscyamine sulfate (0.3111 mg) + Atropine sulfate anyhdrous (0.0582 mg) + Phenobarbital (48.6 mg) + Scopolamine (0.0195 mg)Tablet, extended releaseOralAyerst Laboratories1991-12-311996-09-10Canada flag
Donnatal Extentabs SrtHyoscyamine sulfate (0.3111 mg) + Atropine sulfate anyhdrous (0.0582 mg) + Phenobarbital (48.6 mg) + Scopolamine (0.0195 mg)Tablet, extended releaseOralWyeth Ayerst Canada Inc.1994-12-312001-05-07Canada flag
Donnatal TabHyoscyamine sulfate (0.1037 mg) + Atropine sulfate anyhdrous (0.0194 mg) + Phenobarbital (16.2 mg) + Scopolamine (6.5 mcg)TabletOralWyeth Ayerst Canada Inc.1994-12-312001-05-22Canada flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
AnaspazHyoscyamine sulfate dihydrate (0.125 mg/1)Tablet, orally disintegratingOral; SublingualBF ASCHER AND CO INC1973-01-02Not applicableUS flag
AnaspazHyoscyamine sulfate dihydrate (0.125 mg/1)Tablet, orally disintegratingOral; SublingualPhysicians Total Care, Inc.1973-01-022011-06-30US flag
Azuphen MbHyoscyamine sulfate dihydrate (0.12 mg/1) + Methenamine (120 mg/1) + Methylene blue trihydrate (10 mg/1) + Phenyl salicylate (36 mg/1) + Sodium phosphate, monobasic, monohydrate (40.8 mg/1)CapsuleOralBurel Pharmaceuticals, Llc2015-09-282016-11-01US flag
B-DonnaHyoscyamine sulfate dihydrate (0.1037 mg/1) + Atropine sulfate anyhdrous (0.0194 mg/1) + Phenobarbital (16.2 mg/1) + Scopolamine (0.0065 mg/1)TabletOralWinder Laboratories, LLC2015-12-302016-03-03US flag
Belladonna Alkaloids with PhenobarbitalHyoscyamine sulfate dihydrate (0.1037 mg/1) + Atropine sulfate anyhdrous (0.0194 mg/1) + Phenobarbital (16.2 mg/1) + Scopolamine (0.0065 mg/1)TabletOralHikma Pharmaceuticals USA Inc.1966-01-012019-07-31US flag0143 114020170720 1564 4ev749
Belladonna Alkaloids with PhenobarbitalHyoscyamine sulfate dihydrate (0.1037 mg/1) + Atropine sulfate anyhdrous (0.0194 mg/1) + Phenobarbital (16.2 mg/1) + Scopolamine (0.0065 mg/1)TabletOralbryant ranch prepack1966-01-012015-05-01US flag
Belladonna Alkaloids with PhenobartbitalHyoscyamine sulfate dihydrate (0.1037 mg/1) + Atropine sulfate anyhdrous (0.0194 mg/1) + Phenobarbital (16.2 mg/1) + Scopolamine (0.0065 mg/1)TabletOralApace Packaging2000-12-012015-01-31US flag
Belladonna Alkaloids with PhenobartbitalHyoscyamine sulfate dihydrate (0.1037 mg/1) + Atropine sulfate anyhdrous (0.0194 mg/1) + Phenobarbital (16.2 mg/1) + Scopolamine (0.0065 mg/1)TabletOralPreferreed Pharmaceuticals Inc.2004-08-312013-04-30US flag
Belladonna Alkaloids with PhenobartbitalHyoscyamine sulfate dihydrate (0.1037 mg/1) + Atropine sulfate anyhdrous (0.0194 mg/1) + Phenobarbital (16.2 mg/1) + Scopolamine (0.0065 mg/1)TabletOralPhysicians Total Care, Inc.2004-08-312013-01-15US flag
Belladonna Alkaloids with PhenobartbitalHyoscyamine sulfate dihydrate (0.1037 mg/1) + Atropine sulfate anyhdrous (0.0194 mg/1) + Phenobarbital (16.2 mg/1) + Scopolamine (0.0065 mg/1)TabletOralLiberty Pharmaceuticals, Inc.2000-12-01Not applicableUS flag00143 1140 10 nlmimage10 bb045dd2

Categories

ATC Codes
A03BA03 — HyoscyamineA03CB31 — Hyoscyamine and psycholeptics
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as tropane alkaloids. These are organic compounds containing the nitrogenous bicyclic alkaloid parent N-Methyl-8-azabicyclo[3.2.1]octane.
Kingdom
Organic compounds
Super Class
Alkaloids and derivatives
Class
Tropane alkaloids
Sub Class
Not Available
Direct Parent
Tropane alkaloids
Alternative Parents
Beta hydroxy acids and derivatives / Piperidines / N-alkylpyrrolidines / Benzene and substituted derivatives / Trialkylamines / Carboxylic acid esters / Amino acids and derivatives / Monocarboxylic acids and derivatives / Azacyclic compounds / Primary alcohols
show 4 more
Substituents
Alcohol / Amine / Amino acid or derivatives / Aromatic heteropolycyclic compound / Azacycle / Benzenoid / Beta-hydroxy acid / Carbonyl group / Carboxylic acid derivative / Carboxylic acid ester
show 18 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
tropan-3alpha-yl 3-hydroxy-2-phenylpropanoate (CHEBI:17486) / Tropane alkaloids, Tropan alkaloids (C02046)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
PX44XO846X
CAS number
101-31-5
InChI Key
RKUNBYITZUJHSG-FXUDXRNXSA-N
InChI
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
IUPAC Name
(1R,3S,5S)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl (2S)-3-hydroxy-2-phenylpropanoate
SMILES
CN1[C@H]2CC[C@@H]1C[C@@H](C2)OC(=O)[C@H](CO)C1=CC=CC=C1

References

Synthesis Reference

Jeffrey Kiel, H. Thomas, Emily Ware, Brady Ware, "Phenolic acid complexes of hyoscyamine and process for preparing the same." U.S. Patent US20060128637, issued June 15, 2006.

US20060128637
General References
  1. Evans WC, Ghani A, Treagust PG: Proceedings: Preliminary studies concerning the metabolism of hyoscine and hyoscyamine in the Solanaceae. J Pharm Pharmacol. 1974 Dec;26 Suppl:112P. doi: 10.1111/j.2042-7158.1974.tb10143.x. [Article]
  2. Kohnen-Johannsen KL, Kayser O: Tropane Alkaloids: Chemistry, Pharmacology, Biosynthesis and Production. Molecules. 2019 Feb 22;24(4). pii: molecules24040796. doi: 10.3390/molecules24040796. [Article]
  3. Naji A, Gatling JW: Muscarinic Antagonists . [Article]
  4. Cheshire WP, Fealey RD: Drug-induced hyperhidrosis and hypohidrosis: incidence, prevention and management. Drug Saf. 2008;31(2):109-26. doi: 10.2165/00002018-200831020-00002. [Article]
  5. Mitchelson F: Muscarinic receptor agonists and antagonists: effects on ocular function. Handb Exp Pharmacol. 2012;(208):263-98. doi: 10.1007/978-3-642-23274-9_12. [Article]
  6. Reisinger F: On the Effects of Hyoscyamine and Atropia. Edinb Med Surg J. 1826 Oct 1;26(89):276-279. [Article]
  7. Dailymed: Hyoscyamine Subcutaneous Injection [Link]
  8. Dailymed: Anaspaz (Hyoscyamine) Orally Disintegrating Tablet [Link]
Human Metabolome Database
HMDB0014568
KEGG Drug
D00147
KEGG Compound
C02046
PubChem Compound
154417
PubChem Substance
46507345
ChemSpider
10246417
BindingDB
50239982
RxNav
153970
ChEBI
17486
ChEMBL
CHEMBL1331216
ZINC
ZINC000100009280
Therapeutic Targets Database
DNC000758
PharmGKB
PA164776844
PDBe Ligand
HYO
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Hyoscyamine
PDB Entries
6ttm / 6ttn
MSDS
Download (73.4 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4TerminatedTreatmentLower Urinary Tract Symptoms (LUTS)1
4Unknown StatusPreventionBradycardia / Hypoxemia1
1CompletedTreatmentOrganophosphorus Poisoning1
Not AvailableCompletedSupportive CareSialorrhea1
Not AvailableCompletedTreatmentFunctional Abdominal Pain / Functional Dyspepsia / Functional Gastrointestinal Disorders (FGID) / Irritable Bowel Syndrome (IBS)1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
  • Advanced Pharmaceutical Services Inc.
  • AG Marin Pharmaceuticals
  • Alaven Pharmaceutical
  • Allaire Pharmaceuticals
  • Alphagen Laboratories Inc.
  • Amerifit Inc.
  • Amerisource Health Services Corp.
  • Apicore LLC
  • Apotheca Inc.
  • Aristos Pharmaceuticals
  • Atlantic Biologicals Corporation
  • BF Ascher & Co.
  • Breckenridge Pharmaceuticals
  • Capellon Pharmaceuticals LLC
  • Cardinal Health
  • Cima Laboratories Inc.
  • Concord Labs
  • Contract Pharm
  • County Line Pharmaceuticals LLC
  • Cypress Pharmaceutical Inc.
  • Dayton Pharmaceuticals
  • Dispensing Solutions
  • Diversified Healthcare Services Inc.
  • Duramed
  • Econolab Inc.
  • Edwards Pharmaceuticals
  • Equipharm Inc.
  • Eros Pharma Private Ltd.
  • Ethex Corp.
  • Excellium Pharmaceutical Inc.
  • Franklin Pharmaceutical LLC
  • Great Southern Laboratories
  • Hi Tech Pharmacal Co. Inc.
  • Iopharm Laboratories Inc.
  • Jerome Stevens Pharmaceuticals Inc.
  • Kaiser Foundation Hospital
  • KV Pharmaceutical Co.
  • Kylemore Pharmaceuticals
  • Liberty Pharmaceuticals
  • Major Pharmaceuticals
  • Marlop Pharmaceuticals Inc.
  • Mckesson Corp.
  • Med Tek Pharmaceuticals Inc.
  • Murfreesboro Pharmaceutical Nursing Supply
  • Nucare Pharmaceuticals Inc.
  • Paddock Labs
  • Palmetto Pharmaceuticals Inc.
  • PCA LLC
  • Physicians Total Care Inc.
  • Prasco Labs
  • Prescript Pharmaceuticals
  • Provident Pharmaceuticals LLC
  • Qualitest
  • RA McNeil Co.
  • Resource Optimization and Innovation LLC
  • River's Edge Pharmaceuticals
  • Sandhills Packaging Inc.
  • Schwarz Pharma Inc.
  • Seton Pharmaceuticals LLC
  • Silarx Pharmaceuticals
  • Southwood Pharmaceuticals
  • Sovereign Pharmaceuticals Ltd.
  • Spectrum Pharmaceuticals
  • Sunrise Pharmaceutical Inc.
  • Taylor Pharmaceuticals
  • United Research Laboratories Inc.
  • Vintage Pharmaceuticals Inc.
  • Vision Pharma LLC
Dosage Forms
FormRouteStrength
Tablet, orally disintegratingOral; Sublingual0.125 mg/1
OintmentTopical
TabletOral
Tablet, film coated, extended releaseOral
TabletOral.125 mg/1
LiquidOral0.125 mg/5mL
LiquidOral0.125 mg/1mL
TabletSublingual0.125 mg/1
ElixirOral0.125 mg/5mL
ElixirOral25 mg/1mL
SolutionOral0.125 mg/1mL
Solution / dropsOral0.125 mg/1mL
TabletOral0.125 mg/1
TabletOral0.15 mg/1
TabletOral0.375 mg/1
TabletOral; Sublingual0.125 mg/1
Tablet, extended releaseOral0.375 mg/1
Tablet, multilayerOral.375 mg/1
Tablet, orally disintegratingOral0.125 mg/1
Tablet, orally disintegratingSublingual0.125 mg/1
Tablet, solubleOral0.125 mg/1
Injection, solutionSubcutaneous0.5 mg/1mL
TabletOral0.125 mg
Solution / dropsOral0.125 mg / mL
Tablet, chewableOral0.125 mg/1
Tablet, coatedOral
CapsuleOral
ElixirOral
Tablet, extended releaseOral
Tablet, multilayer, extended releaseOral0.375 mg/1
Tablet, sugar coatedOral
LiquidOral
Prices
Unit descriptionCostUnit
Levsin 0.125 mg/ml Solution 15ml Bottle49.09USD bottle
Levsin 0.5 mg/ml ampul27.33USD ml
Hyoscyamine sulfate powder25.69USD g
Symax Duotab 0.375 mg Controlled Release Tabs3.73USD tab
Symax-SL 0.125 mg Sublingual Tabs3.29USD tab
Symax duotab2.4USD tablet
Levbid 0.375 mg 12 Hour tablet2.12USD tablet
Levbid er 0.375 mg tablet2.09USD tablet
Hyoscyamine Sulfate CR 0.375 mg 12 Hour tablet1.66USD tablet
Levbid 0.375 mg tablet sa1.44USD tablet
Symax-sr 0.375 mg tablet1.4USD tablet
Levsin/SL 0.125 mg Sublingual Tabs1.24USD tab
Symax fastabs 0.125 mg tablet1.21USD tablet
Symax-sl 0.125 mg tablet sl1.17USD tablet
Levsin 0.125 mg tablet1.08USD tablet
Levsin-sl 0.125 mg tablet sl0.97USD tablet
Hyoscyamine Sulfate 0.125 mg tablet0.93USD tablet
Nulev 0.125 mg tablet0.91USD tablet
Hyoscyamine Sulfate 0.125 mg Sublingual Tabs0.88USD tab
Hyomax-sl 0.125 mg tablet sl0.86USD tablet
Hyoscyamine Sulfate 0.125 mg Dispersible Tablet0.83USD dispersible tablet
Hyoscyamine sulf 0.125 mg tablet0.79USD tablet
Hyoscyamine su 0.125 mg tablet0.64USD tablet
Hyoscyamine 0.125 mg tablet sl0.53USD tablet
Hyoscyamine sul 0.15 mg tablet sl0.39USD tablet
Anaspaz 0.125 mg Dispersible Tablet0.36USD dispersible tablet
Levsin 0.125 mg/5ml Elixir0.29USD ml
Anaspaz 0.125 mg tablet sl0.26USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)108.5 °CPhysProp
water solubility3560 mg/L (at 20 °C)MERCK INDEX (1996); pH 9.5
logS-1.91ADME Research, USCD
pKa11.7MERCK INDEX (1996)
Predicted Properties
PropertyValueSource
logP1.57ChemAxon
pKa (Strongest Acidic)15.15ChemAxon
pKa (Strongest Basic)9.39ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area49.77 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity80.82 m3·mol-1ChemAxon
Polarizability31.74 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9286
Blood Brain Barrier+0.9569
Caco-2 permeable+0.8866
P-glycoprotein substrateSubstrate0.5
P-glycoprotein inhibitor INon-inhibitor0.6542
P-glycoprotein inhibitor IINon-inhibitor0.8595
Renal organic cation transporterInhibitor0.7956
CYP450 2C9 substrateNon-substrate0.7041
CYP450 2D6 substrateNon-substrate0.6838
CYP450 3A4 substrateSubstrate0.5496
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 inhibitorNon-inhibitor0.9275
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.9285
CYP450 3A4 inhibitorNon-inhibitor0.95
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9113
Ames testNon AMES toxic0.7742
CarcinogenicityNon-carcinogens0.9631
BiodegradationReady biodegradable0.5527
Rat acute toxicity2.7305 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8354
hERG inhibition (predictor II)Inhibitor0.5378
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Download (8.14 KB)
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Mass Spectrum (Electron Ionization)MSsplash10-00di-9810000000-bdd60b3a23f97899d426
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
MS/MS Spectrum - , positiveLC-MS/MSsplash10-006x-6951100000-43127e046c478d2643e1
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable

Targets

Drugtargets2
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Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Antagonist
General Function
Phosphatidylinositol phospholipase c activity
Specific Function
The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the...
Gene Name
CHRM1
Uniprot ID
P11229
Uniprot Name
Muscarinic acetylcholine receptor M1
Molecular Weight
51420.375 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
  3. Huang XP, Williams FE, Peseckis SM, Messer WS Jr: Pharmacological characterization of human m1 muscarinic acetylcholine receptors with double mutations at the junction of TM VI and the third extracellular domain. J Pharmacol Exp Ther. 1998 Sep;286(3):1129-39. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Antagonist
General Function
G-protein coupled acetylcholine receptor activity
Specific Function
The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the...
Gene Name
CHRM2
Uniprot ID
P08172
Uniprot Name
Muscarinic acetylcholine receptor M2
Molecular Weight
51714.605 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
  3. Lysikova M, Havlas Z, Tucek S: Interactions between allosteric modulators and 4-DAMP and other antagonists at muscarinic receptors: potential significance of the distance between the N and carboxyl C atoms in the molecules of antagonists. Neurochem Res. 2001 Apr;26(4):383-94. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Antagonist
General Function
Receptor activity
Specific Function
The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the...
Gene Name
CHRM3
Uniprot ID
P20309
Uniprot Name
Muscarinic acetylcholine receptor M3
Molecular Weight
66127.445 Da
References
  1. Lysikova M, Havlas Z, Tucek S: Interactions between allosteric modulators and 4-DAMP and other antagonists at muscarinic receptors: potential significance of the distance between the N and carboxyl C atoms in the molecules of antagonists. Neurochem Res. 2001 Apr;26(4):383-94. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Antagonist
General Function
Guanyl-nucleotide exchange factor activity
Specific Function
The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the...
Gene Name
CHRM4
Uniprot ID
P08173
Uniprot Name
Muscarinic acetylcholine receptor M4
Molecular Weight
53048.65 Da
References
  1. Lysikova M, Havlas Z, Tucek S: Interactions between allosteric modulators and 4-DAMP and other antagonists at muscarinic receptors: potential significance of the distance between the N and carboxyl C atoms in the molecules of antagonists. Neurochem Res. 2001 Apr;26(4):383-94. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Metal ion binding
Specific Function
Catalyzes the formation of the signaling molecule cAMP in response to G-protein signaling. Mediates responses to increased cellular Ca(2+)/calmodulin levels (By similarity). May be involved in regu...
Gene Name
ADCY1
Uniprot ID
Q08828
Uniprot Name
Adenylate cyclase type 1
Molecular Weight
123438.85 Da
References
  1. Ricny J, Gualtieri F, Tucek S: Constitutive inhibitory action of muscarinic receptors on adenylyl cyclase in cardiac membranes and its stereospecific suppression by hyoscyamine. Physiol Res. 2002;51(2):131-7. [Article]

Drug created on June 13, 2005 13:24 / Updated on October 22, 2021 21:41