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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
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  • Hyocyamine
  • L-Atropine
  • L-Hyopscyamine
  • L-Hyoscamine
  • L-Hyoscyamine
  • L-Tropine Tropate
Brand names
  • Anaspaz
  • Buwecon
  • Cystospaz
  • Daturine
  • Donnamar
  • Duboisine
  • Duretter
  • Egacene
  • Egazil
  • Gastrosed
  • Levbid
  • Levsin
  • Levsinex
  • Neoquess
  • NuLev
  • OIN
  • Peptard
  • Scopolia Extract
  • Symax
Brand name mixtures Not Available
Categories
  • Antiarrhythmic Agents
  • Mydriatics
  • Bronchodilator Agents
  • Adjuvants, Anesthesia
  • Muscarinic Antagonists
  • Anti-Arrhythmia Agents
  • Antispasmodics
  • Antimuscarinics
  • Parasympatholytics
CAS number 101-31-5
Weight Average: 289.3694
Monoisotopic: 289.167793607
Chemical Formula C17H23NO3
InChI Key InChIKey=RKUNBYITZUJHSG-LGGPCSOHSA-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
Plain Text
IUPAC Name
8-methyl-8-azabicyclo[3.2.1]octan-3-yl (2S)-3-hydroxy-2-phenylpropanoate
SMILES
CN1C2CCC1CC(C2)OC(=O)[C@H](CO)C1=CC=CC=C1
Plain Text
Mass Spec show (8.1 KB)
Taxonomy
Kingdom Organic
Classes
  • Phenylacetates
  • Tropanes
  • Alkaloids and Alkaloid Derivatives
Substructures
  • Carboxylic Acids and Derivatives
  • Hydroxy Compounds
  • Acetates
  • Phenylacetates
  • Pyrrolidines
  • Ethers
  • Benzene and Derivatives
  • Alcohols and Polyols
  • Aliphatic and Aryl Amines
  • Heterocyclic compounds
  • Aromatic compounds
  • Tropanes
  • Alkaloids and Alkaloid Derivatives
  • Piperidines
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.
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.
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
Pharmacoeconomics
Manufacturers Not Available
Packagers
Dosage forms
Form Route Strength
Solution / drops Oral
Tablet Oral
Prices
Unit description Cost Unit
Levsin 0.125 mg/ml Solution 15ml Bottle 49.09 USD bottle
Levsin 0.5 mg/ml ampul 27.33 USD ml
Hyoscyamine sulfate powder 25.69 USD g
Symax Duotab 0.375 mg Controlled Release Tabs 3.73 USD tab
Symax-SL 0.125 mg Sublingual Tabs 3.29 USD tab
Symax duotab 2.4 USD tablet
Levbid 0.375 mg 12 Hour tablet 2.12 USD tablet
Levbid er 0.375 mg tablet 2.09 USD tablet
Hyoscyamine Sulfate CR 0.375 mg 12 Hour tablet 1.66 USD tablet
Levbid 0.375 mg tablet sa 1.44 USD tablet
Symax-sr 0.375 mg tablet 1.4 USD tablet
Levsin/SL 0.125 mg Sublingual Tabs 1.24 USD tab
Symax fastabs 0.125 mg tablet 1.21 USD tablet
Symax-sl 0.125 mg tablet sl 1.17 USD tablet
Levsin 0.125 mg tablet 1.08 USD tablet
Levsin-sl 0.125 mg tablet sl 0.97 USD tablet
Hyoscyamine Sulfate 0.125 mg tablet 0.93 USD tablet
Nulev 0.125 mg tablet 0.91 USD tablet
Hyoscyamine Sulfate 0.125 mg Sublingual Tabs 0.88 USD tab
Hyomax-sl 0.125 mg tablet sl 0.86 USD tablet
Hyoscyamine Sulfate 0.125 mg Dispersible Tablet 0.83 USD dispersible tablet
Hyoscyamine sulf 0.125 mg tablet 0.79 USD tablet
Hyoscyamine su 0.125 mg tablet 0.64 USD tablet
Hyoscyamine 0.125 mg tablet sl 0.53 USD tablet
Hyoscyamine sul 0.15 mg tablet sl 0.39 USD tablet
Anaspaz 0.125 mg Dispersible Tablet 0.36 USD dispersible tablet
Levsin 0.125 mg/5ml Elixir 0.29 USD ml
Anaspaz 0.125 mg tablet sl 0.26 USD tablet
Patents Not Available
Properties
State solid
Melting point 141oC
Experimental Properties
Property Value Source
water solubility 3.56 mg/mL PhysProp
logP 1.8 PhysProp
logS -1.91 [ADME Research, USCD] PhysProp
pKa 11.7 Various sources
Predicted Properties
Property Value Source
water solubility 2.52e+00 g/l ALOGPS
logP 2.19 ALOGPS
logP 1.57 ChemAxon Molconvert
logS -2.06 ALOGPS
pKa ChemAxon Molconvert
hydrogen acceptor count 3 ChemAxon Molconvert
hydrogen donor count 1 ChemAxon Molconvert
polar surface area 49.77 ChemAxon Molconvert
rotatable bond count 5 ChemAxon Molconvert
refractivity 80.82 ChemAxon Molconvert
polarizability 31.88 ChemAxon Molconvert
References
Synthesis Reference Not Available
General Reference Not Available
External Links
Resource Link
PubChem Compound 64692 Link_out
PubChem Substance 46507345 Link_out
ChemSpider 58240 Link_out
ChEBI 17486 Link_out
ChEMBL 17486 Link_out
Therapeutic Targets Database DNC000758 Link_out
Drug Product Database 125857 Link_out
RxList http://www.rxlist.com/cgi/generic/hyoscy.htm Link_out
Drugs.com http://www.drugs.com/cdi/hyoscyamine.html Link_out
Wikipedia http://en.wikipedia.org/wiki/Hyoscyamine Link_out
ATC Codes
  • A03BA03
AHFS Codes
  • 12:08.08
  • 92:02.00*
PDB Entries Not Available
FDA label Not Available
MSDS show (73.4 KB)
Interactions
Drug Interactions Not Available
Food Interactions
  • Take 30 minutes before meals, and at bedtime.
Targets

1. Muscarinic acetylcholine receptor M1

Pharmacological action: yes
Actions: antagonist

The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is Pi turnover

Organism class: human
UniProt ID: P11229 Link_out
Gene: CHRM1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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
  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
  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

2. Muscarinic acetylcholine receptor M2

Pharmacological action: yes
Actions: antagonist

The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is adenylate cyclase inhibition

Organism class: human
UniProt ID: P08172 Link_out
Gene: CHRM2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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
  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
  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

3. Muscarinic acetylcholine receptor M3

Pharmacological action: unknown
Actions: antagonist

The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is Pi turnover

Organism class: human
UniProt ID: P20309 Link_out
Gene: CHRM3 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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

4. Muscarinic acetylcholine receptor M4

Pharmacological action: unknown
Actions: antagonist

The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is inhibition of adenylate cyclase

Organism class: human
UniProt ID: P08173 Link_out
Gene: CHRM4 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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
Comments
Drug created on June 13, 2005 07:24 / Updated on April 19, 2011 15:03

This project is supported by Genome Alberta & Genome Canada, a not-for-profit organization that is leading Canada's national genomics strategy with $600 million in funding from the federal government. This project is also supported in part by GenomeQuest, Inc., an enterprise genomic information company serving the life science community.