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

Stem definitionDrug idCAS RN
atropine derivatives 333 86-13-5

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • cogentin
  • benztropine mesilate
  • benzatropine
  • benztropine
  • tropine benzohydryl ether
  • benztropine mesylate
A centrally active muscarinic antagonist that has been used in the symptomatic treatment of PARKINSON DISEASE. Benztropine also inhibits the uptake of dopamine.
  • Molecular weight: 307.44
  • Formula: C21H25NO
  • CLOGP: 3.52
  • LIPINSKI: 0
  • HAC: 2
  • HDO: 0
  • TPSA: 12.47
  • ALOGS: -5.41
  • ROTB: 4

  • Status: OFP

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

Drug dosage:

DoseUnitRoute
2 mg O
2 mg P

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 1 Hosey CM, Chan R, Benet LZ
MRTD (Maximum Recommended Therapeutic Daily Dose) 0.21 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 29 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H

Approvals:

DateAgencyCompanyOrphan
March 5, 1954 FDA

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
Completed suicide 510.21 58.62 111 282 20923 2336769
Toxicity to various agents 297.77 58.62 79 314 32675 2325017
Ileus paralytic 106.49 58.62 18 375 778 2356914
Cardiac arrest 74.73 58.62 23 370 14907 2342785
Cardio-respiratory arrest 71.83 58.62 20 373 9126 2348566
Neuroleptic malignant syndrome 65.82 58.62 14 379 2066 2355626

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
Completed suicide 451.65 63.82 112 411 16200 1730058
Toxicity to various agents 298.17 63.82 92 431 29049 1717209
Drug abuse 230.41 63.82 64 459 13625 1732633
Agitation 82.95 63.82 28 495 10998 1735260
Neuroleptic malignant syndrome 72.36 63.82 19 504 3129 1743129
Intentional product misuse 68.58 63.82 22 501 7336 1738922

Pharmacologic Action:

SourceCodeDescription
ATC N04AC01 NERVOUS SYSTEM
ANTI-PARKINSON DRUGS
ANTICHOLINERGIC AGENTS
Ethers of tropine or tropine derivatives
CHEBI has role CHEBI:66956 antidyskinesia agent
CHEBI has role CHEBI:48876 muscarinic antagonist
CHEBI has role CHEBI:146270 oneirogen
CHEBI has role CHEBI:48407 antiparkinson drug
CHEBI has role CHEBI:50370 parasympatholytic
MeSH PA D018726 Anti-Dyskinesia Agents
MeSH PA D000978 Antiparkinson Agents
MeSH PA D002491 Central Nervous System Agents
MeSH PA D018678 Cholinergic Agents
MeSH PA D018680 Cholinergic Antagonists
MeSH PA D015259 Dopamine Agents
MeSH PA D018765 Dopamine Uptake Inhibitors
MeSH PA D049990 Membrane Transport Modulators
MeSH PA D018727 Muscarinic Antagonists
MeSH PA D018377 Neurotransmitter Agents
MeSH PA D014179 Neurotransmitter Uptake Inhibitors
MeSH PA D010276 Parasympatholytics
MeSH PA D018373 Peripheral Nervous System Agents
FDA EPC N0000175574 Anticholinergic
FDA EPC N0000175750 Antihistamine
FDA MoA N0000000207 Histamine Receptor Antagonists

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Postencephalitic parkinsonism indication 19972008 DOID:14332
Parkinsonism indication 32798002
Parkinson's disease indication 49049000 DOID:14330
Extrapyramidal disease indication 76349003
Arteriosclerotic Parkinsonism indication
Urinary tract obstruction contraindication 7163005 DOID:5200
Chronic obstructive lung disease contraindication 13645005 DOID:3083
Severe chronic ulcerative colitis contraindication 14311001
Disorder of autonomic nervous system contraindication 15241006
Toxic megacolon contraindication 28536002 DOID:1770
Atony of colon contraindication 29479008
Shigellosis contraindication 36188001
Hypertensive disorder contraindication 38341003 DOID:10763
Conduction disorder of the heart contraindication 44808001
Low blood pressure contraindication 45007003
Achalasia of esophagus contraindication 45564002 DOID:9164
Chronic heart failure contraindication 48447003
Dysuria contraindication 49650001
Paralytic ileus contraindication 55525008 DOID:8442
Ulcerative colitis contraindication 64766004 DOID:8577
Hiatal hernia contraindication 84089009 DOID:12642
Open-angle glaucoma contraindication 84494001 DOID:1067
Kidney disease contraindication 90708001 DOID:557
Thyrotoxicosis contraindication 90739004 DOID:7997
Myasthenia gravis contraindication 91637004 DOID:437
Tardive dyskinesia contraindication 102449007
Dysentery contraindication 111939009
Gastrointestinal obstruction contraindication 126765001
Bleeding contraindication 131148009
Gastroesophageal reflux disease contraindication 235595009 DOID:8534
Disease of liver contraindication 235856003 DOID:409
Benign prostatic hyperplasia contraindication 266569009
Retention of urine contraindication 267064002
Fever contraindication 386661006
Angle-closure glaucoma contraindication 392291006 DOID:13550
Pseudomembranous enterocolitis contraindication 397683000
Gastric ulcer contraindication 397825006 DOID:10808
Disorder of coronary artery contraindication 414024009

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 9.86 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 9.64 WOMBAT-PK CHEMBL
Muscarinic acetylcholine receptor M5 GPCR ANTAGONIST Ki 8.55 WOMBAT-PK
Muscarinic acetylcholine receptor M4 GPCR ANTAGONIST Ki 8.96 WOMBAT-PK
Muscarinic acetylcholine receptor M3 GPCR ANTAGONIST Ki 8.96 WOMBAT-PK
Muscarinic acetylcholine receptor M2 GPCR ANTAGONIST Ki 8.85 WOMBAT-PK
Alpha-2A adrenergic receptor GPCR Ki 6.69 DRUG MATRIX
Sigma non-opioid intracellular receptor 1 Membrane receptor Ki 7.23 DRUG MATRIX
Sodium-dependent noradrenaline transporter Transporter Ki 5.86 DRUG MATRIX
5-hydroxytryptamine receptor 2A GPCR Ki 8.16 DRUG MATRIX
5-hydroxytryptamine receptor 2B GPCR Ki 6.90 DRUG MATRIX
5-hydroxytryptamine receptor 2C GPCR Ki 7.49 DRUG MATRIX
5-hydroxytryptamine receptor 6 GPCR Ki 5.89 DRUG MATRIX
Alpha-2B adrenergic receptor GPCR Ki 7.52 DRUG MATRIX
D(3) dopamine receptor GPCR Ki 6.65 DRUG MATRIX
Histamine H2 receptor GPCR Ki 5.93 DRUG MATRIX
Alpha-2C adrenergic receptor GPCR Ki 7.24 DRUG MATRIX
Alpha-1D adrenergic receptor GPCR Ki 7.59 DRUG MATRIX
Sodium-dependent serotonin transporter Transporter IC50 4.62 CHEMBL
Histamine H1 receptor GPCR Ki 8.96 WOMBAT-PK
Sodium-dependent dopamine transporter Transporter Kd 7.25 WOMBAT-PK
Sodium-dependent neutral amino acid transporter B(0)AT1 Unclassified INHIBITOR IC50 4.36 IUPHAR
Alpha-1B adrenergic receptor GPCR Ki 7.39 DRUG MATRIX
Membrane-associated progesterone receptor component 1 Membrane receptor Ki 6.95 DRUG MATRIX
Sodium-dependent serotonin transporter Transporter Ki 5.29 CHEMBL
Sodium-dependent dopamine transporter Transporter Ki 6.93 CHEMBL
Muscarinic acetylcholine receptor M1 GPCR Ki 9.23 CHEMBL
Muscarinic acetylcholine receptor M2 GPCR Ki 8.59 CHEMBL
Alpha-1A adrenergic receptor GPCR IC50 6.85 CHEMBL

External reference:

IDSource
D001590 MESH_DESCRIPTOR_UI
C0591275 UMLSCUI
D00778 KEGG_DRUG
1NHL2J4X8K UNII
292 INN_ID
372846002 SNOMEDCT_US
77390008 SNOMEDCT_US
4019630 VANDF
004667 NDDF
1424 RXNORM
d00175 MMSL
DB00245 DRUGBANK_ID
CHEMBL1200383 ChEMBL_ID
CXQ PDB_CHEM_ID
CHEBI:3048 CHEBI
132-17-2 SECONDARY_CAS_RN
7601 IUPHAR_LIGAND_ID
1201549 PUBCHEM_CID
CHEMBL1201203 ChEMBL_ID

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Benztropine Mesylate HUMAN PRESCRIPTION DRUG LABEL 1 0143-9729 INJECTION 1 mg INTRAMUSCULAR ANDA 12 sections
Benztropine Mesylate HUMAN PRESCRIPTION DRUG LABEL 1 0603-2437 TABLET 0.50 mg ORAL ANDA 12 sections
Benztropine Mesylate HUMAN PRESCRIPTION DRUG LABEL 1 0603-2438 TABLET 1 mg ORAL ANDA 12 sections
Benztropine Mesylate HUMAN PRESCRIPTION DRUG LABEL 1 0603-2439 TABLET 2 mg ORAL ANDA 12 sections
Benztropine Mesylate HUMAN PRESCRIPTION DRUG LABEL 1 0615-2547 TABLET 0.50 mg ORAL ANDA 11 sections
Benztropine Mesylate HUMAN PRESCRIPTION DRUG LABEL 1 0615-2548 TABLET 1 mg ORAL ANDA 11 sections
Benztropine Mesylate HUMAN PRESCRIPTION DRUG LABEL 1 0615-2549 TABLET 2 mg ORAL ANDA 11 sections
Benztropine Mesylate HUMAN PRESCRIPTION DRUG LABEL 1 0615-7675 TABLET 0.50 mg ORAL ANDA 12 sections
Benztropine Mesylate HUMAN PRESCRIPTION DRUG LABEL 1 0615-7676 TABLET 1 mg ORAL ANDA 12 sections
Benztropine Mesylate HUMAN PRESCRIPTION DRUG LABEL 1 0615-7677 TABLET 2 mg ORAL ANDA 12 sections
Benztropine Mesylate HUMAN PRESCRIPTION DRUG LABEL 1 0615-8210 TABLET 0.50 mg ORAL ANDA 12 sections
Benztropine Mesylate HUMAN PRESCRIPTION DRUG LABEL 1 0615-8211 TABLET 1 mg ORAL ANDA 12 sections
Benztropine Mesylate HUMAN PRESCRIPTION DRUG LABEL 1 0832-1080 TABLET 0.50 mg ORAL ANDA 12 sections
Benztropine Mesylate HUMAN PRESCRIPTION DRUG LABEL 1 0832-1081 TABLET 1 mg ORAL ANDA 12 sections
Benztropine Mesylate HUMAN PRESCRIPTION DRUG LABEL 1 0832-1082 TABLET 2 mg ORAL ANDA 12 sections
Benztropine Mesylate HUMAN PRESCRIPTION DRUG LABEL 1 0904-6788 TABLET 0.50 mg ORAL ANDA 12 sections
Benztropine Mesylate HUMAN PRESCRIPTION DRUG LABEL 1 0904-6789 TABLET 2 mg ORAL ANDA 12 sections
Benztropine Mesylate HUMAN PRESCRIPTION DRUG LABEL 1 0904-6790 TABLET 1 mg ORAL ANDA 12 sections
Benztropine Mesylate HUMAN PRESCRIPTION DRUG LABEL 1 10135-606 TABLET 0.50 mg ORAL ANDA 12 sections
Benztropine Mesylate HUMAN PRESCRIPTION DRUG LABEL 1 10135-607 TABLET 1 mg ORAL ANDA 12 sections
Benztropine Mesylate HUMAN PRESCRIPTION DRUG LABEL 1 10135-608 TABLET 2 mg ORAL ANDA 12 sections
Benztropine Mesylate HUMAN PRESCRIPTION DRUG LABEL 1 17478-012 INJECTION 1 mg INTRAVENOUS NDA authorized generic 12 sections
Benztropine Mesylate HUMAN PRESCRIPTION DRUG LABEL 1 31722-218 TABLET 0.50 mg ORAL ANDA 12 sections
Benztropine Mesylate HUMAN PRESCRIPTION DRUG LABEL 1 31722-219 TABLET 1 mg ORAL ANDA 12 sections
Benztropine Mesylate HUMAN PRESCRIPTION DRUG LABEL 1 31722-220 TABLET 2 mg ORAL ANDA 12 sections
Benztropine Mesylate HUMAN PRESCRIPTION DRUG LABEL 1 43353-580 TABLET 1 mg ORAL ANDA 12 sections
Benztropine Mesylate HUMAN PRESCRIPTION DRUG LABEL 1 43353-707 TABLET 0.50 mg ORAL ANDA 12 sections
Benztropine Mesylate HUMAN PRESCRIPTION DRUG LABEL 1 43353-796 TABLET 1 mg ORAL ANDA 12 sections
Benztropine Mesylate HUMAN PRESCRIPTION DRUG LABEL 1 43353-913 TABLET 0.50 mg ORAL ANDA 12 sections
BENZTROPINE MESYLATE HUMAN PRESCRIPTION DRUG LABEL 1 50090-3882 TABLET 2 mg ORAL ANDA 13 sections