Scopolamine

Identification

Summary

Scopolamine is a belladonna alkaloid with anticholinergic effects indicated for the treatment of nausea and vomiting associated with motion sickness and postoperative nausea and vomiting (PONV).

Brand Names
Donnatal, Phenohytro, Transderm Scop
Generic Name
Scopolamine
DrugBank Accession Number
DB00747
Background

Scopolamine is a tropane alkaloid isolated from members of the Solanaceae family of plants, similar to atropine and hyoscyamine, all of which structurally mimic the natural neurotransmitter acetylcholine.4,6 Scopolamine was first synthesized in 1959, but to date, synthesis remains less efficient than extracting scopolamine from plants.6 As an acetylcholine analogue, scopolamine can antagonize muscarinic acetylcholine receptors (mAChRs) in the central nervous system and throughout the body, inducing several therapeutic and adverse effects related to alteration of parasympathetic nervous system and cholinergic signalling.5,9 Due to its dose-dependent adverse effects, scopolamine was the first drug to be offered commercially as a transdermal delivery system, Scopoderm TTS®, in 1981.4,5 As a result of its anticholinergic effects, scopolamine is being investigated for diverse therapeutic applications; currently, it is approved for the prevention of nausea and vomiting associated with motion sickness and surgical procedures.7,9

Scopolamine was first approved by the FDA on December 31, 1979, and is currently available as both oral tablets and a transdermal delivery system.9

Type
Small Molecule
Groups
Approved, Investigational
Structure
Weight
Average: 303.3529
Monoisotopic: 303.147058165
Chemical Formula
C17H21NO4
Synonyms
  • (-)-hyoscine
  • (-)-scopolamine
  • (1S,3S,5R,6R,7S)-6,7-Epoxytropan-3-yl (2S)-3-hydroxy-2-phenylpropanoate
  • 6-beta,7-beta-Epoxy-3-alpha-tropanyl S-(-)-tropate
  • 6,7-Epoxytropine tropate
  • alpha-(Hydroxymethyl)benzeneacetic acid 9-methyl-3-oxa-9-azatricyclo(3.3.1.0(2.4))non-7-yl ester
  • Hyoscine
  • scopine (-)-tropate
  • scopine (−)-tropate
  • Scopolamine
  • Scopolamine hydrobromide

Pharmacology

Indication

Scopolamine is indicated in adult patients for the prevention of nausea and vomiting associated with motion sickness and for the prevention of postoperative nausea and vomiting (PONV) associated with anesthesia or opiate analgesia.9

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Prophylaxis ofMotion sickness•••••••••••••••••
Prophylaxis ofPost-operative nausea and vomiting•••••••••••••••••
Associated Therapies
Contraindications & Blackbox Warnings
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Pharmacodynamics

Scopolamine is an anticholinergic belladonna alkaloid that, through competitive inhibition of muscarinic receptors, affects parasympathetic nervous system function and acts on smooth muscles that respond to acetylcholine but lack cholinergic innervation. Formulated as a patch, scopolamine is released continuously over three days and remains detectable in urine over a period of 108 hours. Scopolamine is contraindicated in angle-closure glaucoma and should be used with caution in patients with open-angle glaucoma due to scopolamine's ability to increase intraocular pressure. Also, scopolamine exhibits several neuropsychiatric effects: exacerbated psychosis, seizures, seizure-like, and other psychiatric reactions, and cognitive impairment; scopolamine may impair the ability of patients to operate machinery or motor vehicles, play underwater sports, or perform any other potentially hazardous activity. Women with severe preeclampsia should avoid scopolamine. Patients with gastrointestinal or urinary disorders should be monitored frequently for impairments, and scopolamine should be discontinued if these develop. Scopolamine can cause blurred vision if applied directly to the eye, and the transdermal patch should be removed before an MRI procedure to avoid skin burns. Due to its gastrointestinal effects, scopolamine can interfere with gastric secretion testing and should be discontinued at least 10 days before performing the test. Finally, scopolamine may induce dependence and resulting withdrawal symptoms, such as nausea, dizziness, vomiting, gastrointestinal disturbances, sweating, headaches, bradycardia, hypotension, and various neuropsychiatric manifestations following treatment discontinuation; severe symptoms may require medical attention.9

Mechanism of action

Acetylcholine (ACh) is a neurotransmitter that can signal through ligand-gated cation channels (nicotinic receptors) and G-protein-coupled muscarinic receptors (mAChRs). ACh signalling via mAChRs located in the central nervous system (CNS) and periphery can regulate smooth muscle contraction, glandular secretions, heart rate, and various neurological phenomena such as learning and memory.2,3 mAChRs can be divided into five subtypes, M1-M5, expressed at various levels throughout the brain.3 Also, M2 receptors are found in the heart and M3 receptors in smooth muscles, mediating effects apart from the direct modulation of the parasympathetic nervous system.4 While M1, M3, and M5 mAChRs primarily couple to Gq proteins to activate phospholipase C, M2 and M4 mainly couple to Gi/o proteins to inhibit adenylyl cyclase and modulate cellular ion flow.3 This system, in part, helps to control physiological responses such as nausea and vomiting.9

Scopolamine acts as a non-selective competitive inhibitor of M1-M5 mAChRs, albeit with weaker M5 inhibition; as such, scopolamine is an anticholinergic with various dose-dependent therapeutic and adverse effects.4,5,6 The exact mechanism(s) of action of scopolamine remains poorly understood. Recent evidence suggests that M1 (and possibly M2) mAChR antagonism at interneurons acts through inhibition of downstream neurotransmitter release and subsequent pyramidal neuron activation to mediate neurological responses associated with stress and depression.7 Similar antagonism of M4 and M5 receptors is associated with potential therapeutic benefits in neurological conditions such as schizophrenia and substance abuse disorders.3 The significance of these observations to scopolamine's current therapeutic indications of preventing nausea and vomiting is unclear but is linked to its anticholinergic effect and ability to alter signalling through the CNS associated with vomiting.5,9

TargetActionsOrganism
AMuscarinic acetylcholine receptor M1
antagonist
Humans
AMuscarinic acetylcholine receptor M2
antagonist
Humans
AMuscarinic acetylcholine receptor M3
antagonist
Humans
AMuscarinic acetylcholine receptor M4
antagonist
Humans
AMuscarinic acetylcholine receptor M5
antagonist
Humans
UNeuronal acetylcholine receptor subunit alpha-4
inhibitor
inducer
Humans
UNeuronal acetylcholine receptor subunit beta-2
inhibitor
inducer
Humans
USucrase-isomaltase, intestinal
inhibitor
Humans
Absorption

The pharmacokinetics of scopolamine differ substantially between different dosage routes. Oral administration of 0.5 mg scopolamine in healthy volunteers produced a Cmax of 0.54 ± 0.1 ng/mL, a tmax of 23.5 ± 8.2 min, and an AUC of 50.8 ± 1.76 ng*min/mL; the absolute bioavailability is low at 13 ± 1%, presumably because of first-pass metabolism.5 By comparison, IV infusion of 0.5 mg scopolamine over 15 minutes resulted in a Cmax of 5.00 ± 0.43 ng/mL, a tmax of 5.0 min, and an AUC of 369.4 ± 2.2 ng*min/mL.5

Other dose forms have also been tested. Subcutaneous administration of 0.4 mg scopolamine resulted in a Cmax of 3.27 ng/mL, a tmax of 14.6 min, and an AUC of 158.2 ng*min/mL. Intramuscular administration of 0.5 scopolamine resulted in a Cmax of 0.96 ± 0.17 ng/mL, a tmax of 18.5 ± 4.7 min, and an AUC of 81.3 ± 11.2 ng*min/mL. Absorption following intranasal administration was found to be rapid, whereby 0.4 mg of scopolamine resulted in a Cmax of 1.68 ± 0.23 ng/mL, a tmax of 2.2 ± 3 min, and an AUC of 167 ± 20 ng*min/mL; intranasal scopolamine also had a higher bioavailability than that of oral scopolamine at 83 ± 10%.5

Due to dose-dependent adverse effects, the transdermal patch was developed to obtain therapeutic plasma concentrations over a longer period of time. Following patch application, scopolamine becomes detectable within four hours and reaches a peak concentration (tmax) within 24 hours. The average plasma concentration is 87 pg/mL, and the total levels of free and conjugated scopolamine reach 354 pg/mL.9

Volume of distribution

The volume of distribution of scopolamine is not well characterized.9 IV infusion of 0.5 mg scopolamine over 15 minutes resulted in a volume of distribution of 141.3 ± 1.6 L.5

Protein binding

Scopolamine may reversibly bind plasma proteins in humans.9 In rats, scopolamine exhibits relatively low plasma protein binding of 30 ± 10%.5

Metabolism

Little is known about the metabolism of scopolamine in humans, although many metabolites have been detected in animal studies.5 In general, scopolamine is primarily metabolized in the liver, and the primary metabolites are various glucuronide and sulphide conjugates.5,6 Although the enzymes responsible for scopolamine metabolism are unknown, in vitro studies have demonstrated oxidative demethylation linked to CYP3A subfamily activity, and scopolamine pharmacokinetics were significantly altered by coadministration with grapefruit juice, suggesting that CYP3A4 is responsible for at least some of the oxidative demethylation.5,8

Route of elimination

Following oral administration, approximately 2.6% of unchanged scopolamine is recovered in urine.5 Compared to this, using the transdermal patch system, less than 10% of the total dose, both as unchanged scopolamine and metabolites, is recovered in urine over 108 hours. Less than 5% of the total dose is recovered unchanged.9

Half-life

The half-life of scopolamine differs depending on the route. Intravenous, oral, and intramuscular administration have similar half-lives of 68.7 ± 1.0, 63.7 ± 1.3, and 69.1 ±8/0 min, respectively. The half-life is greater with subcutaneous administration at 213 min.5 Following removal of the transdermal patch system, scopolamine plasma concentrations decrease in a log-linear fashion with a half-life of 9.5 hours.9

Clearance

IV infusion of 0.5 mg scopolamine resulted in a clearance of 81.2 ± 1.55 L/h, while subcutaneous administration resulted in a lower clearance of 0.14-0.17 L/h.5

Adverse Effects
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Toxicity

Scopolamine overdose may manifest as lethargy, somnolence, coma, confusion, agitation, hallucinations, convulsion, visual disturbance, dry flushed skin, dry mouth, decreased bowel sounds, urinary retention, tachycardia, hypertension, and supraventricular arrhythmias. In some cases, overdose symptoms may appear similar to those associated with withdrawal following discontinuation. However, withdrawal symptoms such as bradycardia, headache, nausea, abdominal cramps, and sweating can help to distinguish between these possibilities. Overdose management primarily involves the removal of all transdermal patch systems combined with symptomatic and supportive care. Ensuring an adequate airway, supplemental oxygen, establishing intravenous access, and continuous monitoring are recommended. In cases where patients have swallowed one or more patch systems, it may be necessary to remove them or administer activated charcoal.9

Animal studies revealed an oral LD50 of 1880 mg/kg in mice and 1270 mg/kg in rats, and a subcutaneous LD50 of 1650 mg/kg in mice and 296 mg/kg in rats.10

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-BenzodiazepineThe risk or severity of CNS depression can be increased when Scopolamine is combined with 1,2-Benzodiazepine.
AbametapirThe serum concentration of Scopolamine can be increased when it is combined with Abametapir.
AcetazolamideThe risk or severity of CNS depression can be increased when Scopolamine is combined with Acetazolamide.
AcetophenazineThe risk or severity of CNS depression can be increased when Scopolamine is combined with Acetophenazine.
AclidiniumThe risk or severity of adverse effects can be increased when Scopolamine is combined with Aclidinium.
Food Interactions
  • Avoid grapefruit products. Coadministration of scopolamine with grapefruit juice has been shown to delay scopolamine absorption and increase its bioavailability without altering its elimination.

Products

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Product Images
International/Other Brands
Scopoderm / Transderm-Scop (Novartis)
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Isopto HyoscineSolution2.5 mg/1mLOphthalmicAlcon, Inc.1981-06-192012-07-16US flag
ScopaceTablet, soluble0.4 mg/1OralPhysicians Total Care, Inc.2006-03-272011-06-30US flag
Scopolamine HydrobromideInjection, solution0.4 mg/1mLIntramuscular; Intravenous; SubcutaneousFresenius Kabi2000-10-182015-07-24US flag
Scopolamine Hydrobromide InjectionLiquid0.6 mg / mLIntramuscular; Intravenous; SubcutaneousOmega Laboratories Ltd2008-07-08Not applicableCanada flag
Scopolamine Hydrobromide InjectionLiquid0.4 mg / mLIntramuscular; Intravenous; SubcutaneousOmega Laboratories Ltd2008-05-31Not applicableCanada flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
ScopolaminePatch1 mg/3dTransdermalA-S Medication Solutions2019-06-19Not applicableUS flag
ScopolaminePatch1 mg/3dTransdermalMylan Pharmaceuticals Inc.2019-06-19Not applicableUS flag
ScopolaminePatch, extended release1.5 mg/1TransdermalIngenus Pharmaceuticals, LLC2020-11-24Not applicableUS flag
ScopolamineDrug delivery system1 mg/3dTransdermalActavis Pharma, Inc.2022-05-12Not applicableUS flag
Scopolamine Trandermal SystemPatch, extended release1 mg/1Transdermalbryant ranch prepack2017-06-13Not applicableUS flag
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
KimitePatch, extended release1.5 mg/1TopicalOASIS TRADING2018-11-15Not applicableUS flag
SCOPODERM TTS 1.5 TRANSDERMAL THERAPEUTIC SYSTEMPatch1.5 mg/2.5sq cmTransdermalGSK CONSUMER HEALTHCARE SINGAPORE PTE. LTD.1989-06-09Not applicableSingapore flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Diban CapScopolamine (3.3 mcg) + Atropine sulfate (9.7 mcg) + Attapulgite (300 mg) + Hyoscyamine sulfate (0.0519 mg) + Opium (12 mg) + Pectin (71.4 mg)CapsuleOralWyeth Ayerst Canada Inc.1998-02-182001-01-30Canada flag
Diban CapScopolamine (3.3 mcg) + Atropine sulfate (9.7 mcg) + Attapulgite (300 mg) + Hyoscyamine sulfate (0.0519 mg) + Opium (12 mg) + Pectin (71.4 mg)CapsuleOralAyerst Laboratories1992-12-311999-04-12Canada flag
Donnagel LiqScopolamine (6.5 mcg / 30 mL) + Atropine sulfate (0.0194 mg / 30 mL) + Hyoscyamine sulfate (0.1037 mg / 30 mL) + Kaolin (6 g / 30 mL) + Pectin (142.8 mg / 30 mL)LiquidOralAyerst Laboratories1993-12-311996-09-10Canada flag
Donnagel LiqScopolamine (6.5 mcg / 30 mL) + Atropine sulfate (0.0194 mg / 30 mL) + Hyoscyamine sulfate (0.1037 mg / 30 mL) + Kaolin (6 g / 30 mL) + Pectin (142.8 mg / 30 mL)LiquidOralWyeth Ayerst Canada Inc.1995-12-311997-08-14Canada flag
Donnatal ElixirScopolamine (6.5 mcg / 5 mL) + Atropine sulfate (0.0194 mg / 5 mL) + Hyoscyamine sulfate (0.1037 mg / 5 mL) + Phenobarbital (16.2 mg / 5 mL)ElixirOralWyeth Ayerst Canada Inc.1994-12-312001-01-16Canada flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Atenolol ScopolamineScopolamine (.25 mg/25.25mg) + Atenolol (25 mg/25.25mg)TabletBuccal; Oral; Sublingual; TransmucosalTPS2014-10-01Not applicableUS flag
Atenolol ScopolamineScopolamine (.5 mg/50.5mg) + Atenolol (50 mg/50.5mg)TabletOralTPS2014-10-01Not applicableUS flag
B-DonnaScopolamine (0.0065 mg/1) + Atropine sulfate (0.0194 mg/1) + Hyoscyamine sulfate dihydrate (0.1037 mg/1) + Phenobarbital (16.2 mg/1)TabletOralWinder Laboratories, LLC2015-12-302016-03-03US flag
Belladonna Alkaloids with PhenobarbitalScopolamine (0.0065 mg/1) + Atropine sulfate (0.0194 mg/1) + Hyoscyamine sulfate dihydrate (0.1037 mg/1) + Phenobarbital (16.2 mg/1)TabletOralbryant ranch prepack1966-01-012015-05-01US flag
Belladonna Alkaloids with PhenobarbitalScopolamine (0.0065 mg/1) + Atropine sulfate (0.0194 mg/1) + Hyoscyamine sulfate dihydrate (0.1037 mg/1) + Phenobarbital (16.2 mg/1)TabletOralHikma Pharmaceuticals USA Inc.1966-01-012019-07-31US flag

Categories

ATC Codes
N05CM05 — ScopolamineS01FA02 — ScopolamineA04AD01 — ScopolamineA04AD51 — Scopolamine, combinations
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as beta hydroxy acids and derivatives. These are compounds containing a carboxylic acid substituted with a hydroxyl group on the C3 carbon atom.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Hydroxy acids and derivatives
Sub Class
Beta hydroxy acids and derivatives
Direct Parent
Beta hydroxy acids and derivatives
Alternative Parents
Piperidines / Benzene and substituted derivatives / Morpholines / N-alkylpyrrolidines / Trialkylamines / Amino acids and derivatives / Carboxylic acid esters / Azacyclic compounds / Oxacyclic compounds / Dialkyl ethers
show 7 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 22 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
tertiary amino compound, epoxide, propanoate ester, tropane alkaloid (CHEBI:16794)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
DL48G20X8X
CAS number
51-34-3
InChI Key
STECJAGHUSJQJN-FWXGHANASA-N
InChI
InChI=1S/C17H21NO4/c1-18-13-7-11(8-14(18)16-15(13)22-16)21-17(20)12(9-19)10-5-3-2-4-6-10/h2-6,11-16,19H,7-9H2,1H3/t11-,12-,13-,14+,15-,16+/m1/s1
IUPAC Name
(1R,2R,4S,5S,7S)-9-methyl-3-oxa-9-azatricyclo[3.3.1.0^{2,4}]nonan-7-yl (2S)-3-hydroxy-2-phenylpropanoate
SMILES
CN1[C@H]2C[C@@H](C[C@@H]1[C@H]1O[C@@H]21)OC(=O)[C@H](CO)C1=CC=CC=C1

References

Synthesis Reference

Yang Guodong, "Preparation and application of scopolamine and chlorpromazine as a drug-withdrawal agent." U.S. Patent US5543407, issued February, 1993.

US5543407
General References
  1. Putcha L, Cintron NM, Tsui J, Vanderploeg JM, Kramer WG: Pharmacokinetics and oral bioavailability of scopolamine in normal subjects. Pharm Res. 1989 Jun;6(6):481-5. [Article]
  2. Kruse AC, Kobilka BK, Gautam D, Sexton PM, Christopoulos A, Wess J: Muscarinic acetylcholine receptors: novel opportunities for drug development. Nat Rev Drug Discov. 2014 Jul;13(7):549-60. doi: 10.1038/nrd4295. Epub 2014 Jun 6. [Article]
  3. Moran SP, Maksymetz J, Conn PJ: Targeting Muscarinic Acetylcholine Receptors for the Treatment of Psychiatric and Neurological Disorders. Trends Pharmacol Sci. 2019 Dec;40(12):1006-1020. doi: 10.1016/j.tips.2019.10.007. Epub 2019 Nov 8. [Article]
  4. 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]
  5. Renner UD, Oertel R, Kirch W: Pharmacokinetics and pharmacodynamics in clinical use of scopolamine. Ther Drug Monit. 2005 Oct;27(5):655-65. doi: 10.1097/01.ftd.0000168293.48226.57. [Article]
  6. Lakstygal AM, Kolesnikova TO, Khatsko SL, Zabegalov KN, Volgin AD, Demin KA, Shevyrin VA, Wappler-Guzzetta EA, Kalueff AV: DARK Classics in Chemical Neuroscience: Atropine, Scopolamine, and Other Anticholinergic Deliriant Hallucinogens. ACS Chem Neurosci. 2019 May 15;10(5):2144-2159. doi: 10.1021/acschemneuro.8b00615. Epub 2019 Jan 10. [Article]
  7. Wohleb ES, Gerhard D, Thomas A, Duman RS: Molecular and Cellular Mechanisms of Rapid-Acting Antidepressants Ketamine and Scopolamine. Curr Neuropharmacol. 2017;15(1):11-20. doi: 10.2174/1570159x14666160309114549. [Article]
  8. Ebert U, Oertel R, Kirch W: Influence of grapefruit juice on scopolamine pharmacokinetics and pharmacodynamics in healthy male and female subjects. Int J Clin Pharmacol Ther. 2000 Nov;38(11):523-31. doi: 10.5414/cpp38523. [Article]
  9. FDA Approved Drug Products: TRANSDERM SCOP (scopolamine) patch [Link]
  10. Cayman Chemical: scopolamine MSDS [Link]
Human Metabolome Database
HMDB0003573
KEGG Drug
D00138
KEGG Compound
C01851
PubChem Compound
3000322
PubChem Substance
46506966
ChemSpider
10194106
BindingDB
50240039
RxNav
9603
ChEBI
16794
ChEMBL
CHEMBL569713
ZINC
ZINC000100037020
Therapeutic Targets Database
DNC000757
PharmGKB
PA451308
Guide to Pharmacology
GtP Drug Page
PDBe Ligand
OW0
Drugs.com
Drugs.com Drug Page
Wikipedia
Scopolamine
PDB Entries
8cvd
FDA label
Download (686 KB)
MSDS
Download (73.6 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedBasic ScienceHealthy Volunteers (HV)1
4CompletedPreventionFamily Planning1
4CompletedPreventionLaparoscopic Sleeve Gastrectomy (LSG) / Post Operative Nausea and Vomiting (PONV)1
4CompletedPreventionNausea / Satisfaction / Vomiting1
4CompletedPreventionPain Relief With HSG1

Pharmacoeconomics

Manufacturers
  • Boca pharmacal inc
  • Private formulations inc
Packagers
  • A. Aarons Inc.
  • Adamis Laboratories
  • Advanced Pharmaceutical Services Inc.
  • Alcon Laboratories
  • Alza Corp.
  • Amend
  • Apace Packaging
  • Apotheca Inc.
  • APP Pharmaceuticals
  • Aristos Pharmaceuticals
  • A-S Medication Solutions LLC
  • Atlantic Biologicals Corporation
  • Auriga Pharmaceuticals LLC
  • Bausch & Lomb Inc.
  • Baxter International Inc.
  • Boca Pharmacal
  • Bradley Pharmaceuticals Inc.
  • Breckenridge Pharmaceuticals
  • Bryant Ranch Prepack
  • Burel Pharmaceuticals Inc.
  • C.O. Truxton Inc.
  • Carwin Associates Inc.
  • Central Texas Community Health Centers
  • Contract Pharm
  • Cornerstone Pharmacy
  • Corvit Pharmaceuticals
  • Dexo LLC
  • Direct Dispensing Inc.
  • Dispensing Solutions
  • Diversified Healthcare Services Inc.
  • Excellium Pharmaceutical Inc.
  • H.J. Harkins Co. Inc.
  • Hawthorn Pharmaceuticals
  • Hope Pharmaceuticals
  • Irisys Inc.
  • Kaiser Foundation Hospital
  • Kenwood Labs
  • Kraft Pharmaceutical Co. Inc.
  • Kylemore Pharmaceuticals
  • Larken Laboratories Inc.
  • Liberty Pharmaceuticals
  • Llorens Pharmaceutical
  • Magna Pharmaceuticals
  • Major Pharmaceuticals
  • Mckesson Corp.
  • Medi Rx Pharmaceutical Inc.
  • Mikart Inc.
  • Murfreesboro Pharmaceutical Nursing Supply
  • Nexgen Pharma Inc.
  • Novartis AG
  • Nucare Pharmaceuticals Inc.
  • Patient First Corp.
  • PBM Pharmaceuticals Inc.
  • PCA LLC
  • PD-Rx Pharmaceuticals Inc.
  • Pharmaceutical Utilization Management Program VA Inc.
  • Pharmedix
  • Physicians Total Care Inc.
  • Preferred Pharmaceuticals Inc.
  • Prepackage Specialists
  • Provident Pharmaceuticals LLC
  • Qualitest
  • Rebel Distributors Corp.
  • Redpharm Drug
  • Remedy Repack
  • River's Edge Pharmaceuticals
  • Sandhills Packaging Inc.
  • SJ Pharmaceuticals LLC
  • Southwood Pharmaceuticals
  • Sovereign Pharmaceuticals Ltd.
  • Trigen Laboratories Inc.
  • United Research Laboratories Inc.
  • Veratex Corp.
  • Vintage Pharmaceuticals Inc.
  • Vision Pharma LLC
  • West-Ward Pharmaceuticals
Dosage Forms
FormRouteStrength
TabletBuccal; Oral; Sublingual; Transmucosal
TabletOral
InjectionIntramuscular; Intravenous; Subcutaneous400 mcg/ml
CapsuleOral
LiquidOral
Tablet, extended releaseOral
Tablet, film coated, extended releaseOral
SolutionOphthalmic2.5 mg/1mL
Patch, extended releaseTopical1.5 mg/1
ElixirOral
Tablet, solubleOral0.4 mg/1
PatchTransdermal1.5 mg/2.5sq cm
Solution / dropsOphthalmic
Injection, solutionIntramuscular; Intravenous; Subcutaneous
Drug delivery systemTransdermal1 mg/3d
PatchTransdermal1 mg/3d
Patch, extended releaseTransdermal1.5 mg/1
PowderNot applicable1 g/1g
Injection, solutionIntramuscular; Intravenous; Subcutaneous0.4 mg/1mL
LiquidIntramuscular; Intravenous; Subcutaneous0.4 mg / mL
LiquidIntramuscular; Intravenous; Subcutaneous0.6 mg / mL
SolutionIntramuscular; Intravenous; Subcutaneous0.4 mg / 1 mL
SolutionIntramuscular; Intravenous; Subcutaneous0.6 mg / 1 mL
Patch, extended releaseTransdermal1 mg/1
PatchTransdermal
Patch, extended releaseTransdermal1 mg/3d
Prices
Unit descriptionCostUnit
Oscion Cleanser 6% Lotion 340.2 gm Bottle88.56USD bottle
Oscion Cleanser 3% Lotion 340.2 gm Bottle85.69USD bottle
Isopto Hyoscine 0.25% Solution 5ml Bottle30.99USD bottle
Transderm-Scop 1.5 mg (1 Box Contains 4 Patches)14.87USD patch
Transderm-Scop 1.5 mg (1 Box Contains 10 Patches)12.04USD patch
Transderm-scop 1.5 mg/72hr12.01USD each
Scopolamine hbr crystals6.86USD g
Isopto hyoscine 0.25% drops5.59USD ml
Scopolamine 0.4 mg/ml vial5.4USD ml
Buscopan 20 mg/ml4.5USD ml
Pamine forte 5 mg tablet3.9USD tablet
Pamine 2.5 mg tablet2.66USD tablet
Methscopolamine Bromide 5 mg tablet2.17USD tablet
Methscopolamine brom 5 mg tablet2.09USD tablet
Methscopolamine Bromide 2.5 mg tablet1.67USD tablet
Methscopolamine brom 2.5 mg tablet1.61USD tablet
Scopace 0.4 mg tablet0.67USD tablet
Buscopan 10 mg Tablet0.34USD 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)59 °CChemSpider
water solubility1.0X10+5 mg/LYalkowsky, S.H. & He, Y. (2003)
logP0.98Sangster (1994)
Caco2 permeability-4.93ADME Research, USCD
pKa7.75Sangster, J (1994)
Predicted Properties
PropertyValueSource
Water Solubility6.61 mg/mLALOGPS
logP1.4ALOGPS
logP0.89Chemaxon
logS-1.7ALOGPS
pKa (Strongest Acidic)15.15Chemaxon
pKa (Strongest Basic)6.95Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count4Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area62.3 Å2Chemaxon
Rotatable Bond Count5Chemaxon
Refractivity79.72 m3·mol-1Chemaxon
Polarizability31.2 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9615
Blood Brain Barrier+0.8218
Caco-2 permeable+0.8867
P-glycoprotein substrateNon-substrate0.5174
P-glycoprotein inhibitor INon-inhibitor0.87
P-glycoprotein inhibitor IINon-inhibitor0.8623
Renal organic cation transporterInhibitor0.531
CYP450 2C9 substrateNon-substrate0.7002
CYP450 2D6 substrateNon-substrate0.7296
CYP450 3A4 substrateSubstrate0.5253
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 inhibitorNon-inhibitor0.907
CYP450 2D6 inhibitorNon-inhibitor0.927
CYP450 2C19 inhibitorNon-inhibitor0.9025
CYP450 3A4 inhibitorNon-inhibitor0.831
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8682
Ames testNon AMES toxic0.9133
CarcinogenicityNon-carcinogens0.9581
BiodegradationNot ready biodegradable0.9073
Rat acute toxicity2.0907 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9378
hERG inhibition (predictor II)Non-inhibitor0.9167
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-00di-4910000000-24c90e50ab88ad57e82c
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0udi-0009000000-9733effdc3262b114ed6
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0udi-0809000000-a686e4c768aedb57cf8e
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-000i-1901000000-f66f538c7db471e86fd5
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-000i-3900000000-5eedeba4bedea55de9ad
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0udr-7900000000-1309364bbca3810a6afa
LC-MS/MS Spectrum - LC-ESI-IT , positiveLC-MS/MSsplash10-000i-0900000000-1c1d2f52fb7a5d745e1e
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0udr-0069000000-707f0958afc587863742
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0f6t-0902000000-bc75195650e2c241d33b
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0udr-0649000000-c227592a7fb52c268d8b
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0uds-0900000000-03fc8745a6b02811ff8f
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0w2c-2930000000-896554bc746ef6a6e7ec
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-07f0-0950000000-7091f937009639a971be
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-182.7142035
predicted
DarkChem Lite v0.1.0
[M-H]-185.2800035
predicted
DarkChem Lite v0.1.0
[M-H]-167.10954
predicted
DeepCCS 1.0 (2019)
[M+H]+182.9137035
predicted
DarkChem Lite v0.1.0
[M+H]+185.4020035
predicted
DarkChem Lite v0.1.0
[M+H]+169.50511
predicted
DeepCCS 1.0 (2019)
[M+Na]+182.5325035
predicted
DarkChem Lite v0.1.0
[M+Na]+184.9870035
predicted
DarkChem Lite v0.1.0
[M+Na]+175.41763
predicted
DeepCCS 1.0 (2019)

Targets

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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. Murasaki O, Kaibara M, Nagase Y, Mitarai S, Doi Y, Sumikawa K, Taniyama K: Site of action of the general anesthetic propofol in muscarinic M1 receptor-mediated signal transduction. J Pharmacol Exp Ther. 2003 Dec;307(3):995-1000. Epub 2003 Oct 8. [Article]
  2. Klinkenberg I, Blokland A: The validity of scopolamine as a pharmacological model for cognitive impairment: a review of animal behavioral studies. Neurosci Biobehav Rev. 2010 Jul;34(8):1307-50. doi: 10.1016/j.neubiorev.2010.04.001. Epub 2010 Apr 14. [Article]
  3. Renner UD, Oertel R, Kirch W: Pharmacokinetics and pharmacodynamics in clinical use of scopolamine. Ther Drug Monit. 2005 Oct;27(5):655-65. doi: 10.1097/01.ftd.0000168293.48226.57. [Article]
  4. Lakstygal AM, Kolesnikova TO, Khatsko SL, Zabegalov KN, Volgin AD, Demin KA, Shevyrin VA, Wappler-Guzzetta EA, Kalueff AV: DARK Classics in Chemical Neuroscience: Atropine, Scopolamine, and Other Anticholinergic Deliriant Hallucinogens. ACS Chem Neurosci. 2019 May 15;10(5):2144-2159. doi: 10.1021/acschemneuro.8b00615. Epub 2019 Jan 10. [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. Johnson DE, Nedza FM, Spracklin DK, Ward KM, Schmidt AW, Iredale PA, Godek DM, Rollema H: The role of muscarinic receptor antagonism in antipsychotic-induced hippocampal acetylcholine release. Eur J Pharmacol. 2005 Jan 4;506(3):209-19. Epub 2004 Dec 15. [Article]
  2. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
  3. Renner UD, Oertel R, Kirch W: Pharmacokinetics and pharmacodynamics in clinical use of scopolamine. Ther Drug Monit. 2005 Oct;27(5):655-65. doi: 10.1097/01.ftd.0000168293.48226.57. [Article]
  4. Lakstygal AM, Kolesnikova TO, Khatsko SL, Zabegalov KN, Volgin AD, Demin KA, Shevyrin VA, Wappler-Guzzetta EA, Kalueff AV: DARK Classics in Chemical Neuroscience: Atropine, Scopolamine, and Other Anticholinergic Deliriant Hallucinogens. ACS Chem Neurosci. 2019 May 15;10(5):2144-2159. doi: 10.1021/acschemneuro.8b00615. Epub 2019 Jan 10. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
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. Reitz AB, Gupta SK, Huang Y, Parker MH, Ryan RR: The preparation and human muscarinic receptor profiling of oxybutynin and N-desethyloxybutynin enantiomers. Med Chem. 2007 Nov;3(6):543-5. [Article]
  2. Renner UD, Oertel R, Kirch W: Pharmacokinetics and pharmacodynamics in clinical use of scopolamine. Ther Drug Monit. 2005 Oct;27(5):655-65. doi: 10.1097/01.ftd.0000168293.48226.57. [Article]
  3. Lakstygal AM, Kolesnikova TO, Khatsko SL, Zabegalov KN, Volgin AD, Demin KA, Shevyrin VA, Wappler-Guzzetta EA, Kalueff AV: DARK Classics in Chemical Neuroscience: Atropine, Scopolamine, and Other Anticholinergic Deliriant Hallucinogens. ACS Chem Neurosci. 2019 May 15;10(5):2144-2159. doi: 10.1021/acschemneuro.8b00615. Epub 2019 Jan 10. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
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. Reitz AB, Gupta SK, Huang Y, Parker MH, Ryan RR: The preparation and human muscarinic receptor profiling of oxybutynin and N-desethyloxybutynin enantiomers. Med Chem. 2007 Nov;3(6):543-5. [Article]
  2. Renner UD, Oertel R, Kirch W: Pharmacokinetics and pharmacodynamics in clinical use of scopolamine. Ther Drug Monit. 2005 Oct;27(5):655-65. doi: 10.1097/01.ftd.0000168293.48226.57. [Article]
  3. Lakstygal AM, Kolesnikova TO, Khatsko SL, Zabegalov KN, Volgin AD, Demin KA, Shevyrin VA, Wappler-Guzzetta EA, Kalueff AV: DARK Classics in Chemical Neuroscience: Atropine, Scopolamine, and Other Anticholinergic Deliriant Hallucinogens. ACS Chem Neurosci. 2019 May 15;10(5):2144-2159. doi: 10.1021/acschemneuro.8b00615. Epub 2019 Jan 10. [Article]
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
CHRM5
Uniprot ID
P08912
Uniprot Name
Muscarinic acetylcholine receptor M5
Molecular Weight
60073.205 Da
References
  1. Reitz AB, Gupta SK, Huang Y, Parker MH, Ryan RR: The preparation and human muscarinic receptor profiling of oxybutynin and N-desethyloxybutynin enantiomers. Med Chem. 2007 Nov;3(6):543-5. [Article]
  2. Renner UD, Oertel R, Kirch W: Pharmacokinetics and pharmacodynamics in clinical use of scopolamine. Ther Drug Monit. 2005 Oct;27(5):655-65. doi: 10.1097/01.ftd.0000168293.48226.57. [Article]
  3. Lakstygal AM, Kolesnikova TO, Khatsko SL, Zabegalov KN, Volgin AD, Demin KA, Shevyrin VA, Wappler-Guzzetta EA, Kalueff AV: DARK Classics in Chemical Neuroscience: Atropine, Scopolamine, and Other Anticholinergic Deliriant Hallucinogens. ACS Chem Neurosci. 2019 May 15;10(5):2144-2159. doi: 10.1021/acschemneuro.8b00615. Epub 2019 Jan 10. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
Inducer
Curator comments
An in vitro study demonstrated both potentiating and inhibitory effects of scopolamine on human α4β2 nicotinic acetylcholine receptors depending on the concentrations of both scopolamine and acetylcholine.
General Function
Ligand-gated ion channel activity
Specific Function
After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane permeabl...
Gene Name
CHRNA4
Uniprot ID
P43681
Uniprot Name
Neuronal acetylcholine receptor subunit alpha-4
Molecular Weight
69956.47 Da
References
  1. Smulders CJ, Zwart R, Bermudez I, van Kleef RG, Groot-Kormelink PJ, Vijverberg HP: Cholinergic drugs potentiate human nicotinic alpha4beta2 acetylcholine receptors by a competitive mechanism. Eur J Pharmacol. 2005 Feb 21;509(2-3):97-108. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
Inducer
Curator comments
An in vitro study demonstrated both potentiating and inhibitory effects of scopolamine on human α4β2 nicotinic acetylcholine receptors depending on the concentrations of both scopolamine and acetylcholine.
General Function
Ligand-gated ion channel activity
Specific Function
After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane permeabl...
Gene Name
CHRNB2
Uniprot ID
P17787
Uniprot Name
Neuronal acetylcholine receptor subunit beta-2
Molecular Weight
57018.575 Da
References
  1. Smulders CJ, Zwart R, Bermudez I, van Kleef RG, Groot-Kormelink PJ, Vijverberg HP: Cholinergic drugs potentiate human nicotinic alpha4beta2 acetylcholine receptors by a competitive mechanism. Eur J Pharmacol. 2005 Feb 21;509(2-3):97-108. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
Curator comments
Scopolamine was shown to non-competitively inhibit yeast sucrase, suggesting it may also inhibit sucrase-isomaltase in humans.
General Function
Sucrose alpha-glucosidase activity
Specific Function
Plays an important role in the final stage of carbohydrate digestion. Isomaltase activity is specific for both alpha-1,4- and alpha-1,6-oligosaccharides.
Gene Name
SI
Uniprot ID
P14410
Uniprot Name
Sucrase-isomaltase, intestinal
Molecular Weight
209451.49 Da
References
  1. Minai-Tehrani D, Fooladi N, Minoui S, Sobhani-Damavandifar Z, Aavani T, Heydarzadeh S, Attar F, Ghaffari M, Nazem H: Structural changes and inhibition of sucrase after binding of scopolamine. Eur J Pharmacol. 2010 Jun 10;635(1-3):23-6. doi: 10.1016/j.ejphar.2010.02.040. Epub 2010 Mar 15. [Article]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
Curator comments
The likely metabolism of scopolamine by CYP3A4 is based on in vitro drug metabolism studies and in vivo pharmacokinetic studies using the known CYP3A4 inhibitor grapefruit juice.
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Renner UD, Oertel R, Kirch W: Pharmacokinetics and pharmacodynamics in clinical use of scopolamine. Ther Drug Monit. 2005 Oct;27(5):655-65. doi: 10.1097/01.ftd.0000168293.48226.57. [Article]
  2. Ebert U, Oertel R, Kirch W: Influence of grapefruit juice on scopolamine pharmacokinetics and pharmacodynamics in healthy male and female subjects. Int J Clin Pharmacol Ther. 2000 Nov;38(11):523-31. doi: 10.5414/cpp38523. [Article]
  3. Flockhart Table of Drug Interactions [Link]
  4. FDA Drug Development and Drug Interactions: Table of Substrates, Inhibitors and Inducers [Link]

Drug created at June 13, 2005 13:24 / Updated at March 18, 2024 16:48