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
Structure for Scopolamine (DB00747)
- 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
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Prophylaxis of Motion sickness •••••••••••• ••••• Prophylaxis of Post-operative nausea and vomiting •••••••••••• ••••• - Associated Therapies
- Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- 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
Target Actions Organism AMuscarinic acetylcholine receptor M1 antagonistHumans AMuscarinic acetylcholine receptor M2 antagonistHumans AMuscarinic acetylcholine receptor M3 antagonistHumans AMuscarinic acetylcholine receptor M4 antagonistHumans AMuscarinic acetylcholine receptor M5 antagonistHumans UNeuronal acetylcholine receptor subunit alpha-4 inhibitorinducerHumans UNeuronal acetylcholine receptor subunit beta-2 inhibitorinducerHumans USucrase-isomaltase, intestinal inhibitorHumans - 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
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- 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 Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- 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.
Drug Interaction Integrate drug-drug
interactions in your software1,2-Benzodiazepine The risk or severity of CNS depression can be increased when Scopolamine is combined with 1,2-Benzodiazepine. Abametapir The serum concentration of Scopolamine can be increased when it is combined with Abametapir. Acetazolamide The risk or severity of CNS depression can be increased when Scopolamine is combined with Acetazolamide. Acetophenazine The risk or severity of CNS depression can be increased when Scopolamine is combined with Acetophenazine. Aclidinium The 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
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Images
- International/Other Brands
- Scopoderm / Transderm-Scop (Novartis)
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Isopto Hyoscine Solution 2.5 mg/1mL Ophthalmic Alcon, Inc. 1981-06-19 2012-07-16 US 
Scopace Tablet, soluble 0.4 mg/1 Oral Physicians Total Care, Inc. 2006-03-27 2011-06-30 US Scopolamine Hydrobromide Injection, solution 0.4 mg/1mL Intramuscular; Intravenous; Subcutaneous Fresenius Kabi 2000-10-18 2015-07-24 US Scopolamine Hydrobromide Injection Liquid 0.6 mg / mL Intramuscular; Intravenous; Subcutaneous Omega Laboratories Ltd 2008-07-08 Not applicable Canada 
Scopolamine Hydrobromide Injection Liquid 0.4 mg / mL Intramuscular; Intravenous; Subcutaneous Omega Laboratories Ltd 2008-05-31 Not applicable Canada - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Scopolamine Patch 1 mg/3d Transdermal A-S Medication Solutions 2019-06-19 Not applicable US Scopolamine Patch 1 mg/3d Transdermal Mylan Pharmaceuticals Inc. 2019-06-19 Not applicable US Scopolamine Patch, extended release 1.5 mg/1 Transdermal Ingenus Pharmaceuticals, LLC 2020-11-24 Not applicable US Scopolamine Drug delivery system 1 mg/3d Transdermal Actavis Pharma, Inc. 2022-05-12 Not applicable US Scopolamine Trandermal System Patch, extended release 1 mg/1 Transdermal Padagis Israel Pharmaceuticals Ltd 2017-06-13 Not applicable US - Over the Counter Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Kimite Patch, extended release 1.5 mg/1 Topical OASIS TRADING 2018-11-15 Not applicable US SCOPODERM TTS 1.5 TRANSDERMAL THERAPEUTIC SYSTEM Patch 1.5 mg/2.5sq cm Transdermal GSK CONSUMER HEALTHCARE SINGAPORE PTE. LTD. 1989-06-09 Not applicable Singapore 
- Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Diban Cap Scopolamine (3.3 mcg) + Atropine sulfate (9.7 mcg) + Attapulgite (300 mg) + Hyoscyamine sulfate (0.0519 mg) + Opium (12 mg) + Pectin (71.4 mg) Capsule Oral Wyeth Ayerst Canada Inc. 1998-02-18 2001-01-30 Canada Diban Cap Scopolamine (3.3 mcg) + Atropine sulfate (9.7 mcg) + Attapulgite (300 mg) + Hyoscyamine sulfate (0.0519 mg) + Opium (12 mg) + Pectin (71.4 mg) Capsule Oral Ayerst Laboratories 1992-12-31 1999-04-12 Canada Donnagel Liq Scopolamine (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) Liquid Oral Ayerst Laboratories 1993-12-31 1996-09-10 Canada Donnagel Liq Scopolamine (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) Liquid Oral Wyeth Ayerst Canada Inc. 1995-12-31 1997-08-14 Canada Donnatal Elixir Scopolamine (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) Elixir Oral Wyeth Ayerst Canada Inc. 1994-12-31 2001-01-16 Canada - Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Atenolol Scopolamine Scopolamine (.25 mg/25.25mg) + Atenolol (25 mg/25.25mg) Tablet Buccal; Oral; Sublingual; Transmucosal TPS 2014-10-01 Not applicable US Atenolol Scopolamine Scopolamine (.5 mg/50.5mg) + Atenolol (50 mg/50.5mg) Tablet Oral TPS 2014-10-01 Not applicable US B-Donna Scopolamine (0.0065 mg/1) + Atropine sulfate (0.0194 mg/1) + Hyoscyamine sulfate dihydrate (0.1037 mg/1) + Phenobarbital (16.2 mg/1) Tablet Oral Winder Laboratories, LLC 2015-12-30 2016-03-03 US Belladonna Alkaloids with Phenobarbital Scopolamine (0.0065 mg/1) + Atropine sulfate (0.0194 mg/1) + Hyoscyamine sulfate dihydrate (0.1037 mg/1) + Phenobarbital (16.2 mg/1) Tablet Oral Hikma Pharmaceuticals USA Inc. 1966-01-01 2019-07-31 US 
Belladonna Alkaloids with Phenobarbital Scopolamine (0.0065 mg/1) + Atropine sulfate (0.0194 mg/1) + Hyoscyamine sulfate dihydrate (0.1037 mg/1) + Phenobarbital (16.2 mg/1) Tablet Oral bryant ranch prepack 1966-01-01 2015-05-01 US
Categories
- ATC Codes
- N05CM05 — Scopolamine
- N05CM — Other hypnotics and sedatives
- N05C — HYPNOTICS AND SEDATIVES
- N05 — PSYCHOLEPTICS
- N — NERVOUS SYSTEM
- A04AD — Other antiemetics
- A04A — ANTIEMETICS AND ANTINAUSEANTS
- A04 — ANTIEMETICS AND ANTINAUSEANTS
- A — ALIMENTARY TRACT AND METABOLISM
- Drug Categories
- Adjuvants
- Adjuvants, Anesthesia
- Agents producing tachycardia
- Alimentary Tract and Metabolism
- Alkaloids
- Anticholinergic Agents
- Antiemetics
- Antiemetics and Antinauseants
- Antimuscarinics Antispasmodics
- Autonomic Agents
- Aza Compounds
- Azabicyclo Compounds
- Belladonna Alkaloids
- Central Nervous System Agents
- Central Nervous System Depressants
- Cholinergic Agents
- Cytochrome P-450 CYP3A Substrates
- Cytochrome P-450 CYP3A4 Substrates
- Cytochrome P-450 Substrates
- Gastrointestinal Agents
- Hypnotics and Sedatives
- Muscarinic Antagonists
- Mydriatics
- Mydriatics and Cycloplegics
- Nervous System
- Neurotransmitter Agents
- Ophthalmologicals
- Peripheral Nervous System Agents
- Psycholeptics
- Scopolamine Derivatives
- Sensory Organs
- Solanaceous Alkaloids
- Tropanes
- 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
- 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]
- 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]
- 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]
- 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]
- 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]
- 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]
- 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]
- 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]
- FDA Approved Drug Products: TRANSDERM SCOP (scopolamine) patch [Link]
- Cayman Chemical: scopolamine MSDS [Link]
- External Links
- Human Metabolome Database
- HMDB0003573
- KEGG Drug
- D00138
- KEGG Compound
- C01851
- PubChem Compound
- 3000322
- PubChem Substance
- 46506966
- ChemSpider
- 10194106
- BindingDB
- 50240039
- 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 Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 4 Completed Basic Science Healthy Subjects (HS) 1 4 Completed Prevention Family Planning 1 4 Completed Prevention Laparoscopic Sleeve Gastrectomy / Post Operative Nausea and Vomiting (PONV) 1 4 Completed Prevention Nausea / Satisfaction / Vomiting 1 4 Completed Prevention Pain Relief With HSG 1
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
Form Route Strength Tablet Buccal; Oral; Sublingual; Transmucosal Tablet Oral Injection Intramuscular; Intravenous; Subcutaneous 400 mcg/ml Capsule Oral Liquid Oral Tablet, extended release Oral Tablet, film coated, extended release Oral Solution Ophthalmic 2.5 mg/1mL Patch, extended release Topical 1.5 mg/1 Elixir Oral Tablet, soluble Oral 0.4 mg/1 Patch Transdermal 1.5 mg/2.5sq cm Solution / drops Ophthalmic Injection, solution Intramuscular; Intravenous; Subcutaneous Drug delivery system Transdermal 1 mg/3d Patch Transdermal 1 mg/3d Patch, extended release Transdermal 1.5 mg/1 Powder Not applicable 1 g/1g Injection, solution Intramuscular; Intravenous; Subcutaneous 0.4 mg/1mL Liquid Intramuscular; Intravenous; Subcutaneous 0.4 mg / mL Liquid Intramuscular; Intravenous; Subcutaneous 0.6 mg / mL Solution Intramuscular; Intravenous; Subcutaneous 0.4 mg / 1 mL Solution Intramuscular; Intravenous; Subcutaneous 0.6 mg / 1 mL Patch, extended release Transdermal 1 mg/1 Patch Transdermal Patch, extended release Transdermal 1 mg/3d - Prices
Unit description Cost Unit Oscion Cleanser 6% Lotion 340.2 gm Bottle 88.56USD bottle Oscion Cleanser 3% Lotion 340.2 gm Bottle 85.69USD bottle Isopto Hyoscine 0.25% Solution 5ml Bottle 30.99USD 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/72hr 12.01USD each Scopolamine hbr crystals 6.86USD g Isopto hyoscine 0.25% drops 5.59USD ml Scopolamine 0.4 mg/ml vial 5.4USD ml Buscopan 20 mg/ml 4.5USD ml Pamine forte 5 mg tablet 3.9USD tablet Pamine 2.5 mg tablet 2.66USD tablet Methscopolamine Bromide 5 mg tablet 2.17USD tablet Methscopolamine brom 5 mg tablet 2.09USD tablet Methscopolamine Bromide 2.5 mg tablet 1.67USD tablet Methscopolamine brom 2.5 mg tablet 1.61USD tablet Scopace 0.4 mg tablet 0.67USD tablet Buscopan 10 mg Tablet 0.34USD tablet DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 59 °C ChemSpider water solubility 1.0X10+5 mg/L Yalkowsky, S.H. & He, Y. (2003) logP 0.98 Sangster (1994) Caco2 permeability -4.93 ADME Research, USCD pKa 7.75 Sangster, J (1994) - Predicted Properties
Property Value Source Water Solubility 6.61 mg/mL ALOGPS logP 1.4 ALOGPS logP 0.89 Chemaxon logS -1.7 ALOGPS pKa (Strongest Acidic) 15.15 Chemaxon pKa (Strongest Basic) 6.95 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 4 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 62.3 Å2 Chemaxon Rotatable Bond Count 5 Chemaxon Refractivity 79.72 m3·mol-1 Chemaxon Polarizability 31.2 Å3 Chemaxon Number of Rings 4 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9615 Blood Brain Barrier + 0.8218 Caco-2 permeable + 0.8867 P-glycoprotein substrate Non-substrate 0.5174 P-glycoprotein inhibitor I Non-inhibitor 0.87 P-glycoprotein inhibitor II Non-inhibitor 0.8623 Renal organic cation transporter Inhibitor 0.531 CYP450 2C9 substrate Non-substrate 0.7002 CYP450 2D6 substrate Non-substrate 0.7296 CYP450 3A4 substrate Substrate 0.5253 CYP450 1A2 substrate Non-inhibitor 0.9045 CYP450 2C9 inhibitor Non-inhibitor 0.907 CYP450 2D6 inhibitor Non-inhibitor 0.927 CYP450 2C19 inhibitor Non-inhibitor 0.9025 CYP450 3A4 inhibitor Non-inhibitor 0.831 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8682 Ames test Non AMES toxic 0.9133 Carcinogenicity Non-carcinogens 0.9581 Biodegradation Not ready biodegradable 0.9073 Rat acute toxicity 2.0907 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9378 hERG inhibition (predictor II) Non-inhibitor 0.9167
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 182.7142035 predictedDarkChem Lite v0.1.0 [M-H]- 185.2800035 predictedDarkChem Lite v0.1.0 [M-H]- 167.10954 predictedDeepCCS 1.0 (2019) [M+H]+ 182.9137035 predictedDarkChem Lite v0.1.0 [M+H]+ 185.4020035 predictedDarkChem Lite v0.1.0 [M+H]+ 169.50511 predictedDeepCCS 1.0 (2019) [M+Na]+ 182.5325035 predictedDarkChem Lite v0.1.0 [M+Na]+ 184.9870035 predictedDarkChem Lite v0.1.0 [M+Na]+ 175.41763 predictedDeepCCS 1.0 (2019)
Targets
- 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
- 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]
- 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]
- 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]
- 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
- 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]
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
- 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]
- 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
- 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]
- 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]
- 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
- 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]
- 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]
- 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
- 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]
- 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]
- 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
- InhibitorInducer
- 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
- 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
- InhibitorInducer
- 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
- 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
- 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
- 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]
- 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]
- Flockhart Table of Drug Interactions [Link]
- FDA Drug Development and Drug Interactions: Table of Substrates, Inhibitors and Inducers [Link]
Drug created at June 13, 2005 13:24 / Updated at February 20, 2024 23:54