scopolamine Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
2424 51-34-3

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • scopolamine
  • scopolamine hydrobromide
  • hyoscine
  • levo-duboisine
  • scopoderm
  • scopolamine hydrochloride
  • scopolamine HCl
An alkaloid from SOLANACEAE, especially DATURA and SCOPOLIA. Scopolamine and its quaternary derivatives act as antimuscarinics like ATROPINE, but may have more central nervous system effects. Its many uses include an anesthetic premedication, the treatment of URINARY INCONTINENCE and MOTION SICKNESS, an antispasmodic, and a mydriatic and cycloplegic.
  • Molecular weight: 303.36
  • Formula: C17H21NO4
  • CLOGP: 0.29
  • LIPINSKI: 0
  • HAC: 5
  • HDO: 1
  • TPSA: 62.30
  • ALOGS: -1.66
  • ROTB: 5

  • Status: OFP

  • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

DoseUnitRoute
0.90 mg O
0.90 mg P

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 1 Benet LZ, Broccatelli F, Oprea TI
S (Water solubility) 666.67 mg/mL Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 6 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 0.00 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 27 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution) 3.10 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 16 mL/min/kg Lombardo F, Berellini G, Obach RS
t_half (Half-life) 4.50 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
Dec. 31, 1979 FDA NOVARTIS

FDA Adverse Event Reporting System (Female)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Drug hypersensitivity 105.37 34.15 37 277 46606 2311165
Mydriasis 104.61 34.15 20 294 2199 2355572
Nausea 98.94 34.15 45 269 112144 2245627
Anticholinergic syndrome 96.28 34.15 14 300 282 2357489
Disorientation 88.82 34.15 21 293 6351 2351420
Vomiting 73.02 34.15 32 282 71570 2286201
Akathisia 72.05 34.15 14 300 1660 2356111
Vision blurred 71.45 34.15 21 293 14647 2343124
Gastrointestinal disorder 62.55 34.15 17 297 8900 2348871
Dizziness 58.88 34.15 26 288 58639 2299132
Electrocardiogram QT prolonged 55.25 34.15 15 299 7799 2349972
Suicidal ideation 50.06 34.15 15 299 11072 2346699
Confusional state 49.47 34.15 18 296 24326 2333445
Infectious mononucleosis 47.82 34.15 8 306 404 2357367
Hallucination 45.46 34.15 13 301 8135 2349636
Delirium 41.45 34.15 11 303 5212 2352559
Anxiety 39.18 34.15 16 298 29343 2328428
Application site erythema 38.77 34.15 8 306 1272 2356499

FDA Adverse Event Reporting System (Male)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Prescription drug used without a prescription 139.43 45.64 19 195 211 1746356
White blood cell count increased 83.80 45.64 21 193 7291 1739276
Intentional product misuse 73.72 45.64 19 195 7339 1739228
Neutrophil count increased 70.09 45.64 15 199 2578 1743989
Off label use 63.34 45.64 25 189 38546 1708021
Agitation 61.62 45.64 18 196 11008 1735559
Toxicity to various agents 58.85 45.64 22 192 29119 1717448
Overdose 58.32 45.64 19 195 16682 1729885
Death 52.20 45.64 28 186 87415 1659152
Confusional state 49.98 45.64 18 196 21260 1725307
Lower respiratory tract infection 48.59 45.64 12 202 3839 1742728

Pharmacologic Action:

SourceCodeDescription
ATC A04AD01 ALIMENTARY TRACT AND METABOLISM
ANTIEMETICS AND ANTINAUSEANTS
ANTIEMETICS AND ANTINAUSEANTS
Other antiemetics
ATC A04AD51 ALIMENTARY TRACT AND METABOLISM
ANTIEMETICS AND ANTINAUSEANTS
ANTIEMETICS AND ANTINAUSEANTS
Other antiemetics
ATC N05CM05 NERVOUS SYSTEM
PSYCHOLEPTICS
HYPNOTICS AND SEDATIVES
Other hypnotics and sedatives
ATC S01FA02 SENSORY ORGANS
OPHTHALMOLOGICALS
MYDRIATICS AND CYCLOPLEGICS
Anticholinergics
MeSH PA D000759 Adjuvants, Anesthesia
FDA EPC N0000175574 Anticholinergic
CHEBI has role CHEBI:60807 anaesthesia adjuvant
CHEBI has role CHEBI:53784 antispasmodic drug
CHEBI has role CHEBI:50513 mydriatic agent
CHEBI has role CHEBI:60809 adjuvant
CHEBI has role CHEBI:35469 antidepressant
CHEBI has role CHEBI:50919 antiemetic
CHEBI has role CHEBI:48876 muscarinic antagonist
MeSH PA D000932 Antiemetics
MeSH PA D002491 Central Nervous System Agents
MeSH PA D018678 Cholinergic Agents
MeSH PA D018680 Cholinergic Antagonists
MeSH PA D005765 Gastrointestinal Agents
MeSH PA D018727 Muscarinic Antagonists
MeSH PA D009184 Mydriatics
MeSH PA D018377 Neurotransmitter Agents
MeSH PA D018373 Peripheral Nervous System Agents

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Vasomotor rhinitis indication 8229003 DOID:4730
Irritable bowel syndrome indication 10743008 DOID:9778
Peptic ulcer indication 13200003 DOID:750
Motion sickness indication 37031009 DOID:2951
Dilated pupil indication 37125009
Cough indication 49727002
Allergic rhinitis indication 61582004
Nasal discharge indication 64531003
Cycloplegia indication 68158006 DOID:10033
Nasal congestion indication 68235000
Iridocyclitis indication 77971008
Common cold indication 82272006 DOID:10459
Posterior synechiae indication 111512005
Uveitis indication 128473001 DOID:13141
Prevention of Posterior Synechiae indication
Perioperative Mydriasis indication
Prevention of Motion Sickness indication
Prevention of Post-Operative Nausea and Vomiting indication
General anesthesia off-label use 50697003
Excessive salivation off-label use 53827007
Rhinitis off-label use 70076002 DOID:4483
Seasonal allergic rhinitis off-label use 367498001
Brain damage contraindication 2470005
Ocular hypertension contraindication 4210003 DOID:9282
Tachyarrhythmia contraindication 6285003
Suicidal thoughts contraindication 6471006
Urinary tract obstruction contraindication 7163005 DOID:5200
Alcoholism contraindication 7200002
Hyperammonemia contraindication 9360008
Chronic obstructive lung disease contraindication 13645005 DOID:3083
Hepatic encephalopathy contraindication 13920009 DOID:13413
Severe chronic ulcerative colitis contraindication 14311001
Disorder of autonomic nervous system contraindication 15241006
Disorder of lung contraindication 19829001 DOID:850
Myocardial infarction contraindication 22298006 DOID:5844
Glaucoma contraindication 23986001 DOID:1686
Ventricular tachycardia contraindication 25569003
Alcohol intoxication contraindication 25702006
Shock contraindication 27942005
Toxic megacolon contraindication 28536002 DOID:1770
Atony of colon contraindication 29479008
Hyperthyroidism contraindication 34486009 DOID:7998
Depressive disorder contraindication 35489007
Acute hepatitis contraindication 37871000
Hypertensive disorder contraindication 38341003 DOID:10763
Hypovolemic shock contraindication 39419009
Complete trisomy 21 syndrome contraindication 41040004 DOID:14250
Hyperactive behavior contraindication 44548000
Conduction disorder of the heart contraindication 44808001
Achalasia of esophagus contraindication 45564002 DOID:9164
Chronic heart failure contraindication 48447003
Bradycardia contraindication 48867003
Acidosis contraindication 51387008
Coronary arteriosclerosis contraindication 53741008 DOID:3393
Paralytic ileus contraindication 55525008 DOID:8442
Heart disease contraindication 56265001 DOID:114
Peptic reflux disease contraindication 57643001
Hepatic failure contraindication 59927004
Ulcerative colitis contraindication 64766004 DOID:8577
Poisoning by phenobarbital contraindication 64921004
Arterial thrombosis contraindication 65198009
Drug AND/OR toxin-induced diarrhea contraindication 65979008
Substance abuse contraindication 66214007
Psychotic disorder contraindication 69322001
Arteriosclerotic vascular disease contraindication 72092001
Hepatic coma contraindication 72836002 DOID:12550
Diabetes mellitus contraindication 73211009 DOID:9351
Sleep apnea contraindication 73430006 DOID:0050847
Spastic paralysis contraindication 78403003
Disturbance of salivary secretion contraindication 78948009
Chronic idiopathic constipation contraindication 82934008
Hiatal hernia contraindication 84089009 DOID:12642
Open-angle glaucoma contraindication 84494001 DOID:1067
Epilepsy contraindication 84757009 DOID:1826
Kidney disease contraindication 90708001 DOID:557
Myasthenia gravis contraindication 91637004 DOID:437
Magnetic resonance imaging contraindication 113091000
Hypoalbuminemia contraindication 119247004
Gastrointestinal obstruction contraindication 126765001
Autonomic dysreflexia contraindication 129618003
Bleeding contraindication 131148009
Partial atrioventricular block contraindication 195039008
Acute pancreatitis contraindication 197456007 DOID:2913
Myocardial dysfunction contraindication 233928007
Arterial aneurysm contraindication 233981004
Gastroesophageal reflux disease contraindication 235595009 DOID:8534
Disease of liver contraindication 235856003 DOID:409
Bladder outflow obstruction contraindication 236645006
Pyloric obstruction contraindication 244815007
Benign prostatic hyperplasia contraindication 266569009
Dyspnea contraindication 267036007
Retention of urine contraindication 267064002
Anemia contraindication 271737000 DOID:2355
Drowsy contraindication 271782001
Pregnancy, function contraindication 289908002
Thrombocytopenic disorder contraindication 302215000 DOID:1588
Neutropenic disorder contraindication 303011007 DOID:1227
Severe chronic obstructive pulmonary disease contraindication 313299006
Hypoxia contraindication 389086002
Angle-closure glaucoma contraindication 392291006 DOID:13550
Gastric ulcer contraindication 397825006 DOID:10808
Breastfeeding (mother) contraindication 413712001
Chronic lung disease contraindication 413839001
Disorder of coronary artery contraindication 414024009
Porphyria contraindication 418470004
Fever greater than 100.4 Fahrenheit contraindication 426000000
Hypertensive urgency contraindication 443482000

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 13.24 acidic
pKa2 7.95 Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Muscarinic acetylcholine receptor M1 GPCR ANTAGONIST Ki 9 WOMBAT-PK CHEMBL
Muscarinic acetylcholine receptor M5 GPCR Ki 7.75 CHEMBL
Muscarinic acetylcholine receptor M4 GPCR Ki 9.37 WOMBAT-PK
Muscarinic acetylcholine receptor M3 GPCR Ki 9.40 WOMBAT-PK
Muscarinic acetylcholine receptor M2 GPCR Ki 8.86 WOMBAT-PK
Muscarinic acetylcholine receptor GPCR Ki 10.10 CHEMBL
Muscarinic receptor M1 GPCR Ki 9.39 CHEMBL
Muscarinic acetylcholine receptor M1 GPCR Ki 9.28 CHEMBL
Muscarinic acetylcholine receptor M3 GPCR Kd 9.19 CHEMBL
Muscarinic acetylcholine receptor M2 GPCR Kd 8.52 CHEMBL

External reference:

IDSource
4018401 VUID
N0000146728 NUI
C0036442 UMLSCUI
D00138 KEGG_DRUG
451IFR0GXB UNII
6533-68-2 SECONDARY_CAS_RN
72870001 SNOMEDCT_US
4018401 VANDF
1472 MMSL
9601 RXNORM
387409009 SNOMEDCT_US
5444 MMSL
d00986 MMSL
003458 NDDF
CHEBI:16794 CHEBI
DB00747 DRUGBANK_ID
CHEMBL569713 ChEMBL_ID
CHEMBL1187846 ChEMBL_ID
3000322 PUBCHEM_CID
CHEMBL1256744 ChEMBL_ID
D012601 MESH_DESCRIPTOR_UI
CHEMBL2251240 ChEMBL_ID
330 IUPHAR_LIGAND_ID

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Transderm Scop HUMAN PRESCRIPTION DRUG LABEL 1 0067-4345 PATCH, EXTENDED RELEASE 1 mg TRANSDERMAL NDA 18 sections
Transderm Scop HUMAN PRESCRIPTION DRUG LABEL 1 0067-4346 PATCH, EXTENDED RELEASE 1 mg TRANSDERMAL NDA 19 sections
Scopolamine HUMAN PRESCRIPTION DRUG LABEL 1 0378-6470 PATCH 1 mg TRANSDERMAL ANDA 19 sections
Belladonna Alkaloids with Phenobartbital HUMAN PRESCRIPTION DRUG LABEL 4 0440-7183 TABLET 0.01 mg ORAL UNAPPROVED DRUG OTHER 10 sections
Transderm Scop HUMAN PRESCRIPTION DRUG LABEL 1 10019-553 PATCH, EXTENDED RELEASE 1 mg TRANSDERMAL NDA 19 sections
Phenohytro HUMAN PRESCRIPTION DRUG LABEL 4 17856-0123 ELIXIR 0.01 mg ORAL UNAPPROVED DRUG OTHER 12 sections
Phenohytro HUMAN PRESCRIPTION DRUG LABEL 4 17856-0125 ELIXIR 0.01 mg ORAL UNAPPROVED DRUG OTHER 12 sections
PHENOBARBITAL WITH BELLADONNA ALKALOIDS HUMAN PRESCRIPTION DRUG LABEL 4 17856-0162 ELIXIR 0.01 mg ORAL unapproved drug other 12 sections
Donnatal HUMAN PRESCRIPTION DRUG LABEL 4 17856-0423 ELIXIR 0.01 mg ORAL unapproved drug other 12 sections
RE-PB HYOS ELIXIR HUMAN PRESCRIPTION DRUG LABEL 4 21695-594 ELIXIR 0.01 mg ORAL Unapproved drug other 11 sections
Belladonna Alkaloids with Phenobartbital HUMAN PRESCRIPTION DRUG LABEL 4 21695-890 TABLET 0.01 mg ORAL Unapproved drug other 12 sections
QUADRAPAX HUMAN PRESCRIPTION DRUG LABEL 4 21695-970 ELIXIR 0.01 mg ORAL Unapproved drug other 13 sections
Donnatal HUMAN PRESCRIPTION DRUG LABEL 4 42254-268 TABLET 0.01 mg ORAL Unapproved drug other 15 sections
Donnatal HUMAN PRESCRIPTION DRUG LABEL 4 42291-244 ELIXIR 0.01 mg ORAL unapproved drug other 12 sections
Donnatal HUMAN PRESCRIPTION DRUG LABEL 4 42291-245 TABLET 0.01 mg ORAL unapproved drug other 13 sections
Scopolamine Trandermal System HUMAN PRESCRIPTION DRUG LABEL 1 45802-580 PATCH, EXTENDED RELEASE 1 mg TRANSDERMAL ANDA 20 sections
Transderm Scop HUMAN PRESCRIPTION DRUG LABEL 1 54868-2803 PATCH, EXTENDED RELEASE 1 mg TRANSDERMAL NDA 14 sections
Donnatal HUMAN PRESCRIPTION DRUG LABEL 4 59212-422 ELIXIR 0.01 mg ORAL UNAPPROVED DRUG OTHER 12 sections
Donnatal HUMAN PRESCRIPTION DRUG LABEL 4 59212-423 ELIXIR 0.01 mg ORAL UNAPPROVED DRUG OTHER 12 sections
Donnatal HUMAN PRESCRIPTION DRUG LABEL 4 59212-425 TABLET 0.01 mg ORAL UNAPPROVED DRUG OTHER 13 sections
Donnatal Extentabs HUMAN PRESCRIPTION DRUG LABEL 4 66213-421 TABLET, FILM COATED, EXTENDED RELEASE 0.02 mg ORAL unapproved drug other 16 sections
Donnatal HUMAN PRESCRIPTION DRUG LABEL 4 66213-422 ELIXIR 0.01 mg ORAL unapproved drug other 12 sections
Donnatal HUMAN PRESCRIPTION DRUG LABEL 4 66213-423 ELIXIR 0.01 mg ORAL unapproved drug other 12 sections
Donnatal HUMAN PRESCRIPTION DRUG LABEL 4 66213-425 TABLET 0.01 mg ORAL unapproved drug other 15 sections
Donnatal HUMAN PRESCRIPTION DRUG LABEL 4 66689-063 ELIXIR 0.01 mg ORAL UNAPPROVED DRUG OTHER 12 sections
Transderm Scop HUMAN PRESCRIPTION DRUG LABEL 1 66758-208 PATCH, EXTENDED RELEASE 1 mg TRANSDERMAL NDA 19 sections
Phenobarbital, Hyoscyamine Sulfate, Atropine Sulfate and Scopolamine Hydrobromide HUMAN PRESCRIPTION DRUG LABEL 4 66993-117 TABLET 0.01 mg ORAL UNAPPROVED DRUG OTHER 12 sections
phenobarbital, hyoscyamine sulfate, atropine sulfate, scopolamine hydrobromide HUMAN PRESCRIPTION DRUG LABEL 4 66993-118 ELIXIR 0.01 mg ORAL UNAPPROVED DRUG OTHER 12 sections
phenobarbital, hyoscyamine sulfate, atropine sulfate, scopolamine hydrobromide HUMAN PRESCRIPTION DRUG LABEL 4 66993-119 ELIXIR 0.01 mg ORAL UNAPPROVED DRUG OTHER 12 sections
Donnatal HUMAN PRESCRIPTION DRUG LABEL 4 68151-0607 TABLET 0.01 mg ORAL unapproved drug other 15 sections