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

Stem definitionDrug idCAS RN
atropine derivatives 260 51-55-8

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • atropine
  • (+/-)-Atropine
  • atropin
  • atropinum sulphuricum
  • DL-Hyoscyamine
  • tropine tropate
  • atropine sulfate
An alkaloid, originally from Atropa belladonna, but found in other plants, mainly SOLANACEAE. Hyoscyamine is the 3(S)-endo isomer of atropine.
  • Molecular weight: 289.38
  • Formula: C17H23NO3
  • CLOGP: 1.30
  • LIPINSKI: 0
  • HAC: 4
  • HDO: 1
  • TPSA: 49.77
  • ALOGS: -2.06
  • ROTB: 5

  • Status: OFP

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

Drug dosage:

DoseUnitRoute
1.50 mg O
1.50 mg P

ADMET properties:

PropertyValueReference
BA (Bioavailability) 50 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
BDDCS (Biopharmaceutical Drug Disposition Classification System) 3 Benet LZ, Broccatelli F, Oprea TI
S (Water solubility) 0.00 mg/mL Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 57 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 0.03 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
Vd (Volume of distribution) 3.30 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 7.60 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.61 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 4.10 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
Sept. 15, 1960 FDA GD SEARLE LLC

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 214.47 40.59 77 617 46566 2310825
Drug ineffective 144.46 40.59 73 621 101551 2255840
Hypotension 105.98 40.59 42 652 32394 2324997
Stress cardiomyopathy 96.77 40.59 20 674 1441 2355950
Diarrhoea 86.80 40.59 49 645 83515 2273876
Toxicity to various agents 84.98 40.59 36 658 32718 2324673
Cardiac arrest 76.63 40.59 27 667 14903 2342488
Bradycardia 74.78 40.59 24 670 9957 2347434
Anorectal disorder 57.64 40.59 10 684 277 2357114
Hypertension 57.55 40.59 26 668 27335 2330056
Anticholinergic syndrome 57.33 40.59 10 684 286 2357105
Purpura senile 54.91 40.59 7 687 18 2357373
Coma 52.64 40.59 18 676 9038 2348353
Haemodynamic instability 48.95 40.59 11 683 1168 2356223
Vomiting 48.30 40.59 32 662 71570 2285821
Atrioventricular block complete 46.96 40.59 11 683 1403 2355988
Sinus tachycardia 46.64 40.59 13 681 3312 2354079
Tarsal tunnel syndrome 42.88 40.59 6 688 37 2357354
Mydriasis 42.03 40.59 11 683 2208 2355183
Cardiogenic shock 40.77 40.59 11 683 2480 2354911

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
Drug ineffective 146.11 47.87 69 483 63732 1682497
Hypertension 123.63 47.87 44 508 19404 1726825
Emotional disorder 108.64 47.87 22 530 1090 1745139
Anticholinergic syndrome 102.41 47.87 16 536 170 1746059
Mouth ulceration 98.64 47.87 22 530 1733 1744496
Tachycardia 81.51 47.87 29 523 12599 1733630
Stoma site pain 76.98 47.87 11 541 59 1746170
Ill-defined disorder 75.80 47.87 18 534 1863 1744366
Bradycardia 74.84 47.87 26 526 10508 1735721
Change of bowel habit 74.32 47.87 12 540 159 1746070
Gait disturbance 73.87 47.87 27 525 12643 1733586
Anterior chamber disorder 65.76 47.87 9 543 33 1746196
Cardiac arrest 57.51 47.87 24 528 15906 1730323
Muscular weakness 56.54 47.87 21 531 10228 1736001
Diarrhoea 53.78 47.87 34 518 53818 1692411
Toxicity to various agents 52.22 47.87 27 525 29114 1717115
Oxygen saturation decreased 52.03 47.87 17 535 5658 1740571
Decreased appetite 51.21 47.87 25 527 23846 1722383
Hyperhidrosis 49.04 47.87 20 532 12468 1733761
Oral pain 48.90 47.87 12 540 1418 1744811

Pharmacologic Action:

SourceCodeDescription
ATC A03BA01 ALIMENTARY TRACT AND METABOLISM
DRUGS FOR FUNCTIONAL GASTROINTESTINAL DISORDERS
BELLADONNA AND DERIVATIVES, PLAIN
Belladonna alkaloids, tertiary amines
ATC A03CB03 ALIMENTARY TRACT AND METABOLISM
DRUGS FOR FUNCTIONAL GASTROINTESTINAL DISORDERS
ANTISPASMODICS IN COMBINATION WITH PSYCHOLEPTICS
Belladonna and derivatives in combination with psycholeptics
ATC S01FA01 SENSORY ORGANS
OPHTHALMOLOGICALS
MYDRIATICS AND CYCLOPLEGICS
Anticholinergics
MeSH PA D000759 Adjuvants, Anesthesia
FDA EPC N0000175574 Anticholinergic
FDA EPC N0000175700 Cholinergic Muscarinic Antagonist
FDA MoA N0000000125 Cholinergic Muscarinic Antagonists
CHEBI has role CHEBI:38070 anti-arrhythmia drug
CHEBI has role CHEBI:60807 anaesthesia adjuvant
CHEBI has role CHEBI:50513 mydriatic agent
CHEBI has role CHEBI:50370 parasympatholytic
CHEBI has role CHEBI:35523 bronchodilator agent
CHEBI has role CHEBI:136860 antidote to sarin poisoning
CHEBI has role CHEBI:146270 oneirogen
CHEBI has role CHEBI:48876 muscarinic antagonist
MeSH PA D000889 Anti-Arrhythmia Agents
MeSH PA D018927 Anti-Asthmatic Agents
MeSH PA D001993 Bronchodilator Agents
MeSH PA D002317 Cardiovascular Agents
MeSH PA D002491 Central Nervous System Agents
MeSH PA D018678 Cholinergic Agents
MeSH PA D018680 Cholinergic Antagonists
MeSH PA D018727 Muscarinic Antagonists
MeSH PA D009184 Mydriatics
MeSH PA D018377 Neurotransmitter Agents
MeSH PA D010276 Parasympatholytics
MeSH PA D018373 Peripheral Nervous System Agents
MeSH PA D019141 Respiratory System Agents

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Perioperative Mydriasis indication

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 13.24 acidic
pKa2 9.26 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 M3 GPCR ANTAGONIST Ki 9.50 WOMBAT-PK CHEMBL
Muscarinic acetylcholine receptor M2 GPCR ANTAGONIST Ki 8.97 WOMBAT-PK CHEMBL
Muscarinic acetylcholine receptor M1 GPCR ANTAGONIST Ki 9.31 WOMBAT-PK CHEMBL
Alpha-1D adrenergic receptor GPCR Ki 6.18 DRUG MATRIX
Solute carrier family 22 member 1 Transporter IC50 4.91 CHEMBL
Histamine H1 receptor GPCR Ki 5.91 PDSP
Muscarinic acetylcholine receptor M5 GPCR Ki 9.29 WOMBAT-PK
5-hydroxytryptamine receptor 2A GPCR Ki 5.15 PDSP
Muscarinic acetylcholine receptor M4 GPCR Ki 9.39 WOMBAT-PK
5-hydroxytryptamine receptor 2C GPCR Ki 6.28 DRUG MATRIX
Muscarinic receptor M1 GPCR Ki 9.70 CHEMBL
Muscarinic acetylcholine receptor M2 GPCR Ki 9.15 CHEMBL
Muscarinic acetylcholine receptor M5 GPCR Ki 9.07 CHEMBL
Muscarinic acetylcholine receptor M2 GPCR Ki 9.46 CHEMBL
Muscarinic acetylcholine receptor M1 GPCR Ki 9.59 CHEMBL
Nicotinic acetylcholine receptor alpha 5 subunit Ion channel Ki 4.49 CHEMBL
Acetylcholinesterase Enzyme Ki 9.46 CHEMBL
Muscarinic acetylcholine receptor M3 GPCR Ki 9.92 CHEMBL
Muscarinic acetylcholine receptor M4 GPCR Ki 9.28 CHEMBL
Muscarinic acetylcholine receptor GPCR Ki 9.52 CHEMBL

External reference:

IDSource
D001285 MESH_DESCRIPTOR_UI
4019591 VUID
N0000147687 NUI
C0004259 UMLSCUI
D00113 KEGG_DRUG
03J5ZE7KA5 UNII
5908-99-6 SECONDARY_CAS_RN
73949004 SNOMEDCT_US
4019591 VANDF
27333 MMSL
001715 NDDF
1223 RXNORM
372832002 SNOMEDCT_US
d00174 MMSL
CHEBI:16684 CHEBI
DB00572 DRUGBANK_ID
CHEMBL517712 ChEMBL_ID
OIN PDB_CHEM_ID
320 IUPHAR_LIGAND_ID
174174 PUBCHEM_CID
CHEMBL2146146 ChEMBL_ID

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Lomotil HUMAN PRESCRIPTION DRUG LABEL 2 0025-0061 TABLET 0.03 mg ORAL NDA 13 sections
Diphenoxylate Hydrochloride and Atropine Sulfate HUMAN PRESCRIPTION DRUG LABEL 2 0054-3194 SOLUTION 0.03 mg ORAL ANDA 13 sections
Isopto Atropine HUMAN PRESCRIPTION DRUG LABEL 1 0065-0303 SOLUTION 10 mg OPHTHALMIC NDA 16 sections
Diphenoxylate Hydrochloride and Atropine Sulfate HUMAN PRESCRIPTION DRUG LABEL 2 0378-0415 TABLET 0.03 mg ORAL ANDA 12 sections
Atropine Sulfate HUMAN PRESCRIPTION DRUG LABEL 1 0409-1630 INJECTION, SOLUTION 0.10 mg INTRAMUSCULAR NDA 14 sections
ATROPINE SULFATE HUMAN PRESCRIPTION DRUG LABEL 1 0409-4910 INJECTION, SOLUTION 0.10 mg INTRAVENOUS NDA 15 sections
ATROPINE SULFATE HUMAN PRESCRIPTION DRUG LABEL 1 0409-4911 INJECTION, SOLUTION 0.10 mg INTRAVENOUS NDA 15 sections
Atropine Sulfate HUMAN PRESCRIPTION DRUG LABEL 1 0409-9630 INJECTION, SOLUTION 0.05 mg INTRAMUSCULAR NDA 14 sections
Belladonna Alkaloids with Phenobartbital HUMAN PRESCRIPTION DRUG LABEL 4 0440-7183 TABLET 0.02 mg ORAL UNAPPROVED DRUG OTHER 10 sections
Atropine Sulfate HUMAN PRESCRIPTION DRUG LABEL 1 0517-0401 INJECTION, SOLUTION 0.40 mg INTRAMUSCULAR UNAPPROVED DRUG OTHER 11 sections
Atropine Sulfate HUMAN PRESCRIPTION DRUG LABEL 1 0517-1010 INJECTION, SOLUTION 1 mg INTRAMUSCULAR UNAPPROVED DRUG OTHER 11 sections
DIPHENOXYLATE HYDROCHLORIDE AND ATROPINE SULFATE HUMAN PRESCRIPTION DRUG LABEL 2 0527-1170 TABLET 0.03 mg ORAL ANDA 12 sections
Diphenoxylate Hydrochloride and Atropine Sulfate HUMAN PRESCRIPTION DRUG LABEL 2 0615-7801 TABLET 0.03 mg ORAL ANDA 12 sections
Atropine Sulfate HUMAN PRESCRIPTION DRUG LABEL 1 0641-6006 INJECTION 0.40 mg INTRAMUSCULAR UNAPPROVED DRUG OTHER 12 sections
Diphenoxylate hydrochloride and atropine sulfate HUMAN PRESCRIPTION DRUG LABEL 2 0832-0590 TABLET 0.03 mg ORAL ANDA 13 sections
ATROPEN Auto-Injector HUMAN PRESCRIPTION DRUG LABEL 1 11704-101 INJECTION 2 mg INTRAMUSCULAR NDA 13 sections
ATROPEN Auto-Injector HUMAN PRESCRIPTION DRUG LABEL 1 11704-104 INJECTION 0.50 mg INTRAMUSCULAR NDA 13 sections
ATROPEN Auto-Injector HUMAN PRESCRIPTION DRUG LABEL 1 11704-105 INJECTION 1 mg INTRAMUSCULAR NDA 13 sections
ATROPEN Auto-Injector HUMAN PRESCRIPTION DRUG LABEL 1 11704-106 INJECTION 2 mg INTRAMUSCULAR NDA 13 sections
ATROPEN Auto-Injector HUMAN PRESCRIPTION DRUG LABEL 1 11704-107 INJECTION 0.25 mg INTRAMUSCULAR NDA 13 sections
DuoDote HUMAN PRESCRIPTION DRUG LABEL 2 11704-620 KIT 2.10 mg INTRAMUSCULAR NDA 17 sections
ATNAA atropine and pralidoxime chloride HUMAN PRESCRIPTION DRUG LABEL 2 11704-777 KIT 2.10 mg INTRAMUSCULAR NDA 13 sections
Diphenoxylate Hydrochloride and Atropine Sulfate HUMAN PRESCRIPTION DRUG LABEL 2 12634-531 TABLET 0.03 mg ORAL ANDA 12 sections
Atropine HUMAN PRESCRIPTION DRUG LABEL 1 13985-606 SOLUTION/ DROPS 10 mg OPHTHALMIC NDA 16 sections
Diphenoxylate Hcl and Atropine Sulfate HUMAN PRESCRIPTION DRUG LABEL 1 16590-080 TABLET 0.03 mg ORAL ANDA 13 sections
Atropine HUMAN PRESCRIPTION DRUG LABEL 1 17478-215 SOLUTION/ DROPS 10 mg OPHTHALMIC NDA 16 sections
Phenohytro HUMAN PRESCRIPTION DRUG LABEL 4 17856-0123 ELIXIR 0.02 mg ORAL UNAPPROVED DRUG OTHER 12 sections
Phenohytro HUMAN PRESCRIPTION DRUG LABEL 4 17856-0125 ELIXIR 0.02 mg ORAL UNAPPROVED DRUG OTHER 12 sections
PHENOBARBITAL WITH BELLADONNA ALKALOIDS HUMAN PRESCRIPTION DRUG LABEL 4 17856-0162 ELIXIR 0.02 mg ORAL unapproved drug other 12 sections
Donnatal HUMAN PRESCRIPTION DRUG LABEL 4 17856-0423 ELIXIR 0.02 mg ORAL unapproved drug other 12 sections