Identification

Name
Hyoscyamine
Accession Number
DB00424  (APRD00607)
Type
Small Molecule
Groups
Approved
Description

Hyoscyamine is a chemical compound, a tropane alkaloid it is the levo-isomer to atropine. It is a secondary metabolite of some plants, particularly henbane (Hyoscamus niger.) Hyoscyamine is used to provide symptomatic relief to various gastrointestinal disorders including spasms, peptic ulcers, irritable bowel syndrome, pancreatitis, colic and cystitis. It has also been used to relieve some heart problems, control some of the symptoms of Parkinson's disease, as well as for control of respiratory secretions in end of life care.

Structure
Thumb
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
Product Ingredients
IngredientUNIICASInChI Key
Hyoscyamine hydrobromideIWT50P9S79 306-03-6VZDNSFSBCMCXSK-PGQIENJJSA-N
Hyoscyamine sulfateOB570Z127K 620-61-1Not applicable
Hyoscyamine sulfate dihydrateF2R8V82B84 6835-16-1BXSVDJUWKSRQMD-ITMJLNKNSA-N
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
LevsinTablet0.125 mgOralSchwarz Pharma Kremers Urban Company1960-12-312008-08-08Canada
Levsin Drops 0.125mg/mlSolution / drops0.125 mgOralSchwarz Pharma Kremers Urban Company1982-12-311996-09-09Canada
Unapproved/Other Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
AnaspazTablet, orally disintegrating.125 mg/1Oral; SublingualBF ASCHER AND CO INC1973-01-02Not applicableUs
Ed-spazTablet, orally disintegrating.125 mg/1OralEdwards Pharmaceuticals, Inc2010-05-12Not applicableUs
HyoscyamineLiquid.125 mg/mLOralPatrin Pharma2011-09-04Not applicableUs
HyoscyamineTablet.125 mg/1OralWallace Pharmaceuticals Inc.2016-04-01Not applicableUs
HyoscyamineLiquid.125 mg/5mLOralPatrin Pharma2011-09-04Not applicableUs
Hyoscyamine ERTablet.375 mg/1OralWallace Pharmaceuticals Inc.2016-05-01Not applicableUs
Hyoscyamine SLTablet, orally disintegrating.125 mg/1OralWallace Pharmaceuticals Inc.2016-04-15Not applicableUs
Hyoscyamine SulfateTablet.375 mg/1OralClinical Solutions Wholsesale2009-11-052017-06-29Us
Hyoscyamine SulfateTablet.125 mg/1Oral; SublingualPd Rx Pharmaceuticals, Inc.2009-09-21Not applicableUs
Hyoscyamine SulfateTablet.125 mg/1OralCounty Line Pharamceuticals2009-11-05Not applicableUs
International/Other Brands
Acupaz (Glitz) / Anapaz (Hilton) / Anaspaz (Ascher) / Atropen / Boots Travel Calm (Boots) / Buwecon (Yung Shin) / Cystospaz / Cytospaz (Amerifit) / Donnamar / Egazil (BioPhausia) / Levbid / Levsinex / NuLev / Symax (Capellon)
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Azuphen MbHyoscyamine (.12 mg/1) + Methenamine (120 mg/1) + Methylene blue (10 mg/1) + Phenyl salicylate (36 mg/1) + Sodium phosphate (40.8 mg/1)CapsuleOralBurel Pharmaceuticals, Llc2015-09-28Not applicableUs
B-DonnaHyoscyamine (.1037 mg/1) + Atropine (.0194 mg/1) + Phenobarbital (16.2 mg/1) + Scopolamine (.0065 mg/1)TabletOralWinder Laboratories, LLC2015-12-302016-03-11Us
Belladonna Alkaloids with PhenobarbitalHyoscyamine (.1037 mg/1) + Atropine (.0194 mg/1) + Phenobarbital (16.2 mg/1) + Scopolamine (.0065 mg/1)TabletOralWest Ward Pharmaceutical1966-01-01Not applicableUs0143 114020170720 1564 4ev749
Belladonna Alkaloids with PhenobartbitalHyoscyamine (.1037 mg/1) + Atropine (.0194 mg/1) + Phenobarbital (16.2 mg/1) + Scopolamine (.0065 mg/1)TabletOralApace Packaging2000-12-01Not applicableUs
Belladonna Alkaloids with PhenobartbitalHyoscyamine (.1037 mg/1) + Atropine (.0194 mg/1) + Phenobarbital (16.2 mg/1) + Scopolamine (.0065 mg/1)TabletOralLegacy Pharmaceutical Packaging2000-12-01Not applicableUs
Belladonna Alkaloids with PhenobartbitalHyoscyamine (.1037 mg/1) + Atropine (.0194 mg/1) + Phenobarbital (16.2 mg/1) + Scopolamine (.0065 mg/1)TabletOralLiberty Pharmaceuticals, Inc.2000-12-01Not applicableUs00143 1140 10 nlmimage10 bb045dd2
Belladonna Alkaloids with PhenobartbitalHyoscyamine (.1037 mg/1) + Atropine (.0194 mg/1) + Phenobarbital (16.2 mg/1) + Scopolamine (.0065 mg/1)TabletOralRebel Distributors2004-08-31Not applicableUs
Calmitol Itching Relief OntHyoscyamine (.0001 %) + Camphor (.62 %) + Chloral hydrate (.496 %) + Menthol (.58 %) + Zinc oxide (12.5 %)OintmentTopicalPfizer Canada Inc., Consumer Healthcare Division1964-12-311996-09-09Canada
Diban CapHyoscyamine (0.0519 mg) + Atropine (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
Diban CapHyoscyamine (0.0519 mg) + Atropine (9.7 mcg) + Attapulgite (300 mg) + Opium (12 mg) + Pectin (71.4 mg) + Scopolamine (3.3 mcg)CapsuleOralAyerst Laboratories1992-12-311999-04-12Canada
Categories
UNII
PX44XO846X
CAS number
101-31-5
Weight
Average: 289.3694
Monoisotopic: 289.167793607
Chemical Formula
C17H23NO3
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,3R,5S)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl (2S)-3-hydroxy-2-phenylpropanoate
SMILES

Pharmacology

Indication

For treatment of bladder spasms, peptic ulcer disease, diverticulitis, colic, irritable bowel syndrome, cystitis, and pancreatitis. Also used to treat certain heart conditions, to control the symptoms of Parkinson's disease and rhinitis.

Structured Indications
Pharmacodynamics

L-Hyoscyamine, the active optical isomer of atropine (dl-hyoscyamine), is a tertiary amine anticholinergic gastrointestinal agent.

Mechanism of action

Hyoscyamine competes favorably with acetylcholine for binding at muscarinic receptors in the salivary, bronchial, and sweat glands as well as in the eye, heart, and gastrointestinal tract. The actions of hyoscyamine result in a reduction in salivary, bronchial, gastric and sweat gland secretions, mydriasis, cycloplegia, change in heart rate, contraction of the bladder detrusor muscle and of the gastrointestinal smooth muscle, and decreased gastrointestinal motility.

TargetActionsOrganism
AMuscarinic acetylcholine receptor M1
antagonist
Human
AMuscarinic acetylcholine receptor M2
antagonist
Human
UMuscarinic acetylcholine receptor M3
antagonist
Human
UMuscarinic acetylcholine receptor M4
antagonist
Human
Absorption

Absorbed totally and completely by sublingual administration as well as oral administration.

Volume of distribution
Not Available
Protein binding

50%

Metabolism

Hepatic

Route of elimination
Not Available
Half life

2-3.5 hours

Clearance
Not Available
Toxicity

Symptoms of overdose include headache, nausea, vomiting, blurred vision, dilated pupils, hot dry skin, dizziness, dryness of the mouth, difficulty in swallowing, and CNS stimulation. LD50=mg/kg(orally in rat)

Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
1,10-PhenanthrolineThe therapeutic efficacy of Hyoscyamine can be decreased when used in combination with 1,10-Phenanthroline.Experimental
AclidiniumAclidinium may increase the anticholinergic activities of Hyoscyamine.Approved
AlcuroniumThe risk or severity of adverse effects can be increased when Hyoscyamine is combined with Alcuronium.Experimental
AlfentanilThe risk or severity of adverse effects can be increased when Hyoscyamine is combined with Alfentanil.Approved, Illicit
AlgeldrateThe serum concentration of Hyoscyamine can be decreased when it is combined with Algeldrate.Experimental
AlmagateThe serum concentration of Hyoscyamine can be decreased when it is combined with Almagate.Experimental
AlmasilateThe serum concentration of Hyoscyamine can be decreased when it is combined with Almasilate.Experimental
AloglutamolThe serum concentration of Hyoscyamine can be decreased when it is combined with Aloglutamol.Experimental
AlphacetylmethadolThe risk or severity of adverse effects can be increased when Hyoscyamine is combined with Alphacetylmethadol.Experimental, Illicit
AlphaprodineThe risk or severity of adverse effects can be increased when Hyoscyamine is combined with Alphaprodine.Illicit
AluminiumThe serum concentration of Hyoscyamine can be decreased when it is combined with Aluminium.Approved
Aluminium acetoacetateThe serum concentration of Hyoscyamine can be decreased when it is combined with Aluminium acetoacetate.Experimental
Aluminium glycinateThe serum concentration of Hyoscyamine can be decreased when it is combined with Aluminium glycinate.Experimental
Aluminum hydroxideThe serum concentration of Hyoscyamine can be decreased when it is combined with Aluminum hydroxide.Approved
AmbenoniumThe therapeutic efficacy of Hyoscyamine can be decreased when used in combination with Ambenonium.Approved
Anisotropine MethylbromideThe risk or severity of adverse effects can be increased when Hyoscyamine is combined with Anisotropine Methylbromide.Approved
AtracuriumThe risk or severity of adverse effects can be increased when Hyoscyamine is combined with Atracurium.Experimental
Atracurium besylateThe risk or severity of adverse effects can be increased when Hyoscyamine is combined with Atracurium besylate.Approved
AtropineThe risk or severity of adverse effects can be increased when Atropine is combined with Hyoscyamine.Approved, Vet Approved
BenactyzineThe risk or severity of adverse effects can be increased when Hyoscyamine is combined with Benactyzine.Withdrawn
BendroflumethiazideThe serum concentration of Bendroflumethiazide can be increased when it is combined with Hyoscyamine.Approved
BenzatropineThe risk or severity of adverse effects can be increased when Benzatropine is combined with Hyoscyamine.Approved
BezitramideThe risk or severity of adverse effects can be increased when Hyoscyamine is combined with Bezitramide.Experimental, Illicit, Withdrawn
BiperidenThe risk or severity of adverse effects can be increased when Biperiden is combined with Hyoscyamine.Approved
Bismuth SubcitrateThe serum concentration of Hyoscyamine can be decreased when it is combined with Bismuth Subcitrate.Approved
Bismuth subnitrateThe serum concentration of Hyoscyamine can be decreased when it is combined with Bismuth subnitrate.Experimental
BornaprineThe risk or severity of adverse effects can be increased when Bornaprine is combined with Hyoscyamine.Experimental
Botulinum Toxin Type AHyoscyamine may increase the anticholinergic activities of Botulinum Toxin Type A.Approved, Investigational
Botulinum Toxin Type BHyoscyamine may increase the anticholinergic activities of Botulinum Toxin Type B.Approved
BuprenorphineThe risk or severity of adverse effects can be increased when Hyoscyamine is combined with Buprenorphine.Approved, Illicit, Investigational, Vet Approved
ButorphanolThe risk or severity of adverse effects can be increased when Hyoscyamine is combined with Butorphanol.Approved, Illicit, Vet Approved
Calcium CarbonateThe serum concentration of Hyoscyamine can be decreased when it is combined with Calcium Carbonate.Approved
Calcium silicateThe serum concentration of Hyoscyamine can be decreased when it is combined with Calcium silicate.Experimental
CarfentanilThe risk or severity of adverse effects can be increased when Hyoscyamine is combined with Carfentanil.Illicit, Vet Approved
ChlorothiazideThe serum concentration of Chlorothiazide can be increased when it is combined with Hyoscyamine.Approved, Vet Approved
ChlorphenoxamineThe risk or severity of adverse effects can be increased when Hyoscyamine is combined with Chlorphenoxamine.Withdrawn
ChlorthalidoneThe serum concentration of Chlorthalidone can be increased when it is combined with Hyoscyamine.Approved
CimetropiumHyoscyamine may increase the anticholinergic activities of Cimetropium.Experimental
CodeineThe risk or severity of adverse effects can be increased when Hyoscyamine is combined with Codeine.Approved, Illicit
CoumaphosThe therapeutic efficacy of Hyoscyamine can be decreased when used in combination with Coumaphos.Vet Approved
CyclopenthiazideThe serum concentration of Cyclopenthiazide can be increased when it is combined with Hyoscyamine.Experimental
CyclopentolateThe risk or severity of adverse effects can be increased when Cyclopentolate is combined with Hyoscyamine.Approved
DarifenacinThe risk or severity of adverse effects can be increased when Hyoscyamine is combined with Darifenacin.Approved, Investigational
DecamethoniumThe therapeutic efficacy of Hyoscyamine can be decreased when used in combination with Decamethonium.Approved
DemecariumThe therapeutic efficacy of Hyoscyamine can be decreased when used in combination with Demecarium.Approved
DesloratadineThe risk or severity of adverse effects can be increased when Hyoscyamine is combined with Desloratadine.Approved, Investigational
DexetimideThe risk or severity of adverse effects can be increased when Dexetimide is combined with Hyoscyamine.Withdrawn
DextromoramideThe risk or severity of adverse effects can be increased when Hyoscyamine is combined with Dextromoramide.Experimental, Illicit
DextropropoxypheneThe risk or severity of adverse effects can be increased when Hyoscyamine is combined with Dextropropoxyphene.Approved, Illicit, Withdrawn
DezocineThe risk or severity of adverse effects can be increased when Hyoscyamine is combined with Dezocine.Approved
DichlorvosThe therapeutic efficacy of Hyoscyamine can be decreased when used in combination with Dichlorvos.Vet Approved
DicyclomineThe risk or severity of adverse effects can be increased when Hyoscyamine is combined with Dicyclomine.Approved
DihydrocodeineThe risk or severity of adverse effects can be increased when Hyoscyamine is combined with Dihydrocodeine.Approved, Illicit
DihydroetorphineThe risk or severity of adverse effects can be increased when Hyoscyamine is combined with Dihydroetorphine.Experimental, Illicit
DihydromorphineThe risk or severity of adverse effects can be increased when Hyoscyamine is combined with Dihydromorphine.Experimental, Illicit
DiphenoxylateThe risk or severity of adverse effects can be increased when Hyoscyamine is combined with Diphenoxylate.Approved, Illicit
DistigmineThe therapeutic efficacy of Hyoscyamine can be decreased when used in combination with Distigmine.Experimental
DonepezilThe therapeutic efficacy of Hyoscyamine can be decreased when used in combination with Donepezil.Approved
DPDPEThe risk or severity of adverse effects can be increased when Hyoscyamine is combined with DPDPE.Investigational
DronabinolHyoscyamine may increase the tachycardic activities of Dronabinol.Approved, Illicit
EchothiophateThe therapeutic efficacy of Hyoscyamine can be decreased when used in combination with Echothiophate.Approved
EdrophoniumThe therapeutic efficacy of Hyoscyamine can be decreased when used in combination with Edrophonium.Approved
EluxadolineHyoscyamine may increase the constipating activities of Eluxadoline.Approved
EmeproniumThe risk or severity of adverse effects can be increased when Hyoscyamine is combined with Emepronium.Experimental
EtanautineThe risk or severity of adverse effects can be increased when Hyoscyamine is combined with Etanautine.Experimental
EthopropazineThe risk or severity of adverse effects can be increased when Ethopropazine is combined with Hyoscyamine.Approved
EthylmorphineThe risk or severity of adverse effects can be increased when Hyoscyamine is combined with Ethylmorphine.Approved, Illicit
EtorphineThe risk or severity of adverse effects can be increased when Hyoscyamine is combined with Etorphine.Illicit, Vet Approved
EtybenzatropineThe risk or severity of adverse effects can be increased when Hyoscyamine is combined with Etybenzatropine.Experimental
FentanylThe risk or severity of adverse effects can be increased when Hyoscyamine is combined with Fentanyl.Approved, Illicit, Investigational, Vet Approved
FenthionThe therapeutic efficacy of Hyoscyamine can be decreased when used in combination with Fenthion.Vet Approved
FesoterodineThe risk or severity of adverse effects can be increased when Hyoscyamine is combined with Fesoterodine.Approved
GalantamineThe therapeutic efficacy of Hyoscyamine can be decreased when used in combination with Galantamine.Approved
GallamineThe risk or severity of adverse effects can be increased when Hyoscyamine is combined with Gallamine.Experimental
Gallamine TriethiodideThe risk or severity of adverse effects can be increased when Hyoscyamine is combined with Gallamine Triethiodide.Approved
Ginkgo bilobaThe therapeutic efficacy of Hyoscyamine can be decreased when used in combination with Ginkgo biloba.Approved, Nutraceutical
Glucagon recombinantThe risk or severity of adverse effects can be increased when Hyoscyamine is combined with Glucagon recombinant.Approved
GlycopyrroniumHyoscyamine may increase the anticholinergic activities of Glycopyrronium.Approved, Investigational, Vet Approved
HeroinThe risk or severity of adverse effects can be increased when Hyoscyamine is combined with Heroin.Approved, Illicit
HexamethoniumThe risk or severity of adverse effects can be increased when Hyoscyamine is combined with Hexamethonium.Experimental
HomatropineThe risk or severity of adverse effects can be increased when Hyoscyamine is combined with Homatropine.Approved
Huperzine AThe therapeutic efficacy of Hyoscyamine can be decreased when used in combination with Huperzine A.Investigational
HydrochlorothiazideThe serum concentration of Hydrochlorothiazide can be increased when it is combined with Hyoscyamine.Approved, Vet Approved
HydrocodoneThe risk or severity of adverse effects can be increased when Hyoscyamine is combined with Hydrocodone.Approved, Illicit
HydroflumethiazideThe serum concentration of Hydroflumethiazide can be increased when it is combined with Hyoscyamine.Approved
HydromorphoneThe risk or severity of adverse effects can be increased when Hyoscyamine is combined with Hydromorphone.Approved, Illicit
HydrotalciteThe serum concentration of Hyoscyamine can be decreased when it is combined with Hydrotalcite.Experimental
IndapamideThe serum concentration of Indapamide can be increased when it is combined with Hyoscyamine.Approved
IpidacrineThe therapeutic efficacy of Hyoscyamine can be decreased when used in combination with Ipidacrine.Experimental
Ipratropium bromideThe risk or severity of adverse effects can be increased when Ipratropium bromide is combined with Hyoscyamine.Approved
IsoflurophateThe therapeutic efficacy of Hyoscyamine can be decreased when used in combination with Isoflurophate.Approved, Withdrawn
ItoprideThe therapeutic efficacy of Itopride can be decreased when used in combination with Hyoscyamine.Investigational
KetobemidoneThe risk or severity of adverse effects can be increased when Hyoscyamine is combined with Ketobemidone.Approved
Levomethadyl AcetateThe risk or severity of adverse effects can be increased when Hyoscyamine is combined with Levomethadyl Acetate.Approved
LevorphanolThe risk or severity of adverse effects can be increased when Hyoscyamine is combined with Levorphanol.Approved
LofentanilThe risk or severity of adverse effects can be increased when Hyoscyamine is combined with Lofentanil.Illicit
MagaldrateThe serum concentration of Hyoscyamine can be decreased when it is combined with Magaldrate.Withdrawn
Magnesium HydroxideThe serum concentration of Hyoscyamine can be decreased when it is combined with Magnesium Hydroxide.Approved
Magnesium oxideThe serum concentration of Hyoscyamine can be decreased when it is combined with Magnesium oxide.Approved
Magnesium peroxideThe serum concentration of Hyoscyamine can be decreased when it is combined with Magnesium peroxide.Experimental
Magnesium silicateThe serum concentration of Hyoscyamine can be decreased when it is combined with Magnesium silicate.Experimental
Magnesium TrisilicateThe serum concentration of Hyoscyamine can be decreased when it is combined with Magnesium Trisilicate.Approved
MalathionThe therapeutic efficacy of Hyoscyamine can be decreased when used in combination with Malathion.Approved, Investigational
MazaticolThe risk or severity of adverse effects can be increased when Hyoscyamine is combined with Mazaticol.Experimental
MecamylamineThe risk or severity of adverse effects can be increased when Hyoscyamine is combined with Mecamylamine.Approved
MefloquineThe therapeutic efficacy of Hyoscyamine can be decreased when used in combination with Mefloquine.Approved
MemantineThe therapeutic efficacy of Hyoscyamine can be decreased when used in combination with Memantine.Approved, Investigational
MeptazinolThe risk or severity of adverse effects can be increased when Hyoscyamine is combined with Meptazinol.Experimental
MethadoneThe risk or severity of adverse effects can be increased when Hyoscyamine is combined with Methadone.Approved
Methadyl AcetateThe risk or severity of adverse effects can be increased when Hyoscyamine is combined with Methadyl Acetate.Approved, Illicit
Methanesulfonyl FluorideThe therapeutic efficacy of Hyoscyamine can be decreased when used in combination with Methanesulfonyl Fluoride.Investigational
MethanthelineThe risk or severity of adverse effects can be increased when Hyoscyamine is combined with Methantheline.Approved
MethyclothiazideThe serum concentration of Methyclothiazide can be increased when it is combined with Hyoscyamine.Approved
Methyl salicylateThe therapeutic efficacy of Hyoscyamine can be decreased when used in combination with Methyl salicylate.Approved, Vet Approved
MetixeneThe risk or severity of adverse effects can be increased when Hyoscyamine is combined with Metixene.Approved
MetoclopramideThe therapeutic efficacy of Hyoscyamine can be decreased when used in combination with Metoclopramide.Approved, Investigational
MetolazoneThe serum concentration of Metolazone can be increased when it is combined with Hyoscyamine.Approved
MianserinMianserin may increase the anticholinergic activities of Hyoscyamine.Approved
MinaprineThe therapeutic efficacy of Hyoscyamine can be decreased when used in combination with Minaprine.Approved
MirabegronThe risk or severity of adverse effects can be increased when Hyoscyamine is combined with Mirabegron.Approved
MorphineThe risk or severity of adverse effects can be increased when Hyoscyamine is combined with Morphine.Approved, Investigational
NabiloneHyoscyamine may increase the tachycardic activities of Nabilone.Approved, Investigational
NalbuphineThe risk or severity of adverse effects can be increased when Hyoscyamine is combined with Nalbuphine.Approved
NeostigmineThe therapeutic efficacy of Hyoscyamine can be decreased when used in combination with Neostigmine.Approved, Vet Approved
NicomorphineThe risk or severity of adverse effects can be increased when Hyoscyamine is combined with Nicomorphine.Experimental
NormethadoneThe risk or severity of adverse effects can be increased when Hyoscyamine is combined with Normethadone.Approved, Illicit
OpiumThe risk or severity of adverse effects can be increased when Hyoscyamine is combined with Opium.Approved, Illicit
OrphenadrineThe risk or severity of adverse effects can be increased when Orphenadrine is combined with Hyoscyamine.Approved
OtiloniumThe risk or severity of adverse effects can be increased when Hyoscyamine is combined with Otilonium.Experimental
OxitropiumThe risk or severity of adverse effects can be increased when Hyoscyamine is combined with Oxitropium.Investigational
OxybutyninThe risk or severity of adverse effects can be increased when Hyoscyamine is combined with Oxybutynin.Approved, Investigational
OxycodoneThe risk or severity of adverse effects can be increased when Hyoscyamine is combined with Oxycodone.Approved, Illicit, Investigational
OxymorphoneThe risk or severity of adverse effects can be increased when Hyoscyamine is combined with Oxymorphone.Approved, Investigational, Vet Approved
OxyphenoniumThe risk or severity of adverse effects can be increased when Oxyphenonium is combined with Hyoscyamine.Approved
PancuroniumThe risk or severity of adverse effects can be increased when Hyoscyamine is combined with Pancuronium.Approved
ParaoxonThe therapeutic efficacy of Hyoscyamine can be decreased when used in combination with Paraoxon.Experimental
PentazocineThe risk or severity of adverse effects can be increased when Hyoscyamine is combined with Pentazocine.Approved, Vet Approved
PentoliniumThe risk or severity of adverse effects can be increased when Hyoscyamine is combined with Pentolinium.Approved
PethidineThe risk or severity of adverse effects can be increased when Hyoscyamine is combined with Pethidine.Approved
PhenazocineThe risk or severity of adverse effects can be increased when Hyoscyamine is combined with Phenazocine.Experimental
PhenglutarimideThe risk or severity of adverse effects can be increased when Phenglutarimide is combined with Hyoscyamine.Experimental
PhenoperidineThe risk or severity of adverse effects can be increased when Hyoscyamine is combined with Phenoperidine.Experimental
PhysostigmineThe therapeutic efficacy of Hyoscyamine can be decreased when used in combination with Physostigmine.Approved
PipecuroniumThe risk or severity of adverse effects can be increased when Hyoscyamine is combined with Pipecuronium.Approved
PirenzepineThe risk or severity of adverse effects can be increased when Hyoscyamine is combined with Pirenzepine.Approved
PiritramideThe risk or severity of adverse effects can be increased when Hyoscyamine is combined with Piritramide.Investigational
PolythiazideThe serum concentration of Polythiazide can be increased when it is combined with Hyoscyamine.Approved
Potassium ChlorideHyoscyamine may increase the ulcerogenic activities of Potassium Chloride.Approved, Withdrawn
PramlintidePramlintide may increase the anticholinergic activities of Hyoscyamine.Approved, Investigational
ProcyclidineThe risk or severity of adverse effects can be increased when Procyclidine is combined with Hyoscyamine.Approved
PropanthelineThe risk or severity of adverse effects can be increased when Hyoscyamine is combined with Propantheline.Approved
PropiverineThe risk or severity of adverse effects can be increased when Hyoscyamine is combined with Propiverine.Investigational
PyridostigmineThe therapeutic efficacy of Hyoscyamine can be decreased when used in combination with Pyridostigmine.Approved
QuinethazoneThe serum concentration of Quinethazone can be increased when it is combined with Hyoscyamine.Approved
QuinidineThe risk or severity of adverse effects can be increased when Hyoscyamine is combined with Quinidine.Approved
RamosetronHyoscyamine may increase the constipating activities of Ramosetron.Approved
RemifentanilThe risk or severity of adverse effects can be increased when Hyoscyamine is combined with Remifentanil.Approved
RivastigmineThe therapeutic efficacy of Hyoscyamine can be decreased when used in combination with Rivastigmine.Approved, Investigational
ScopolamineThe risk or severity of adverse effects can be increased when Scopolamine is combined with Hyoscyamine.Approved
Scopolamine butylbromideThe risk or severity of adverse effects can be increased when Hyoscyamine is combined with Scopolamine butylbromide.Approved, Vet Approved
SecretinThe therapeutic efficacy of Secretin can be decreased when used in combination with Hyoscyamine.Approved, Investigational
SolifenacinThe risk or severity of adverse effects can be increased when Hyoscyamine is combined with Solifenacin.Approved
SufentanilThe risk or severity of adverse effects can be increased when Hyoscyamine is combined with Sufentanil.Approved, Investigational
SulpirideThe therapeutic efficacy of Sulpiride can be decreased when used in combination with Hyoscyamine.Approved
TacrineThe therapeutic efficacy of Hyoscyamine can be decreased when used in combination with Tacrine.Withdrawn
TapentadolThe risk or severity of adverse effects can be increased when Hyoscyamine is combined with Tapentadol.Approved
TilidineThe risk or severity of adverse effects can be increased when Hyoscyamine is combined with Tilidine.Experimental
TiotropiumHyoscyamine may increase the anticholinergic activities of Tiotropium.Approved
TolterodineThe risk or severity of adverse effects can be increased when Hyoscyamine is combined with Tolterodine.Approved, Investigational
TopiramateThe risk or severity of adverse effects can be increased when Hyoscyamine is combined with Topiramate.Approved
TramadolThe risk or severity of adverse effects can be increased when Hyoscyamine is combined with Tramadol.Approved, Investigational
TrichlorfonThe therapeutic efficacy of Hyoscyamine can be decreased when used in combination with Trichlorfon.Vet Approved
TrichlormethiazideThe serum concentration of Trichlormethiazide can be increased when it is combined with Hyoscyamine.Approved, Vet Approved
TrihexyphenidylThe risk or severity of adverse effects can be increased when Trihexyphenidyl is combined with Hyoscyamine.Approved
TrimethaphanThe risk or severity of adverse effects can be increased when Hyoscyamine is combined with Trimethaphan.Approved
TropatepineThe risk or severity of adverse effects can be increased when Hyoscyamine is combined with Tropatepine.Experimental
TropicamideThe risk or severity of adverse effects can be increased when Tropicamide is combined with Hyoscyamine.Approved
TrospiumThe risk or severity of adverse effects can be increased when Trospium is combined with Hyoscyamine.Approved
TubocurarineThe risk or severity of adverse effects can be increased when Hyoscyamine is combined with Tubocurarine.Approved
UmeclidiniumUmeclidinium may increase the anticholinergic activities of Hyoscyamine.Approved
VecuroniumThe risk or severity of adverse effects can be increased when Hyoscyamine is combined with Vecuronium.Approved
Food Interactions
  • Take 30 minutes before meals, and at bedtime.

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
Not Available
External Links
Human Metabolome Database
HMDB14568
KEGG Drug
D00147
KEGG Compound
C02046
PubChem Compound
154417
PubChem Substance
46507345
ChemSpider
10246417
ChEBI
17486
ChEMBL
CHEMBL1331216
Therapeutic Targets Database
DNC000758
PharmGKB
PA164776844
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Hyoscyamine
ATC Codes
A03CB31 — Hyoscyamine and psycholepticsA03BA03 — Hyoscyamine
AHFS Codes
  • 12:08.08
  • 92:02.00*
PDB Entries
Not Available
FDA label
Not Available
MSDS
Download (73.4 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
Not AvailableRecruitingTreatmentFunctional Abdominal Pain / Functional Dyspepsia / Functional Gastrointestinal Disorders / Irritable Bowel Syndrome (IBS)1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Dosage forms
FormRouteStrength
Tablet, orally disintegratingOral; Sublingual.125 mg/1
TabletOral
OintmentTopical
CapsuleOral
LiquidOral
Tablet, extended releaseOral
Tablet, film coated, extended releaseOral
Tablet, orally disintegratingOral.125 mg/1
LiquidOral.125 mg/5mL
LiquidOral.125 mg/mL
SolutionOral.125 mg/mL
TabletOral.125 mg/1
TabletOral; Sublingual.125 mg/1
TabletSublingual.125 mg/1
TabletOral.375 mg/1
Tablet, solubleOral.125 mg/1
ElixirOral.125 mg/5mL
Solution / dropsOral.125 mg/mL
Injection, solutionSubcutaneous.5 mg/mL
TabletOral0.125 mg
Solution / dropsOral0.125 mg
Tablet, chewableOral.125 mg/1
Tablet, extended releaseOral.375 mg/1
Tablet, orally disintegratingSublingual.125 mg/1
ElixirOral
Tablet, multilayer, extended releaseOral.375 mg/1
Tablet, coatedOral
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
logP1.8Not Available
logS-1.91ADME Research, USCD
pKa11.7MERCK INDEX (1996)
Predicted Properties
PropertyValueSource
Water Solubility2.52 mg/mLALOGPS
logP2.19ALOGPS
logP1.57ChemAxon
logS-2.1ALOGPS
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

Taxonomy

Description
This compound belongs to the class of chemical entities known as tropane alkaloids. These are organic compounds containing the nitrogenous bicyclic alkaloid parent N-Methyl-8-azabicyclo[3.2.1]octane.
Kingdom
Chemical entities
Super Class
Organic compounds
Class
Alkaloids and derivatives
Sub Class
Tropane alkaloids
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
Tropane alkaloid / Beta-hydroxy acid / Monocyclic benzene moiety / Hydroxy acid / Piperidine / Benzenoid / N-alkylpyrrolidine / Pyrrolidine / Amino acid or derivatives / 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 )

Targets

Kind
Protein
Organism
Human
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. [PubMed:17139284 ]
  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. [PubMed:17016423 ]
  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. [PubMed:9732369 ]
Kind
Protein
Organism
Human
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. [PubMed:17139284 ]
  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. [PubMed:17016423 ]
  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. [PubMed:11495349 ]
Kind
Protein
Organism
Human
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. [PubMed:11495349 ]
Kind
Protein
Organism
Human
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. [PubMed:11495349 ]

Drug created on June 13, 2005 07:24 / Updated on October 16, 2017 08:59