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

Stem definitionDrug idCAS RN
acetylcholinesterase inhibitors 2159 57-47-6

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • physostigmine
  • cogmine
  • eserine
  • esromiotin
  • (-)-Physostigmine
  • physostigmine salicylate
  • eserine hemisulfate salt
  • eserine hemisulfate
A cholinesterase inhibitor that is rapidly absorbed through membranes. It can be applied topically to the conjunctiva. It also can cross the blood-brain barrier and is used when central nervous system effects are desired, as in the treatment of severe anticholinergic toxicity.
  • Molecular weight: 275.35
  • Formula: C15H21N3O2
  • CLOGP: 1.95
  • LIPINSKI: 0
  • HAC: 5
  • HDO: 1
  • TPSA: 44.81
  • ALOGS: -2.44
  • ROTB: 2

Drug dosage:

DoseUnitRoute
0.40 ml None

ADMET properties:

PropertyValueReference
MRTD (Maximum Recommended Therapeutic Daily Dose) 0.06 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BDDCS (Biopharmaceutical Drug Disposition Classification System) 1 Hosey CM, Chan R, Benet LZ
BA (Bioavailability) 10 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution) 3.90 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 72 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.64 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 1 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
Jan. 1, 1875 YEAR INTRODUCED

FDA Adverse Event Reporting System (Female)

None

FDA Adverse Event Reporting System (Male)

None

Pharmacologic Action:

SourceCodeDescription
ATC S01EB05 SENSORY ORGANS
OPHTHALMOLOGICALS
ANTIGLAUCOMA PREPARATIONS AND MIOTICS
Parasympathomimetics
ATC V03AB19 VARIOUS
ALL OTHER THERAPEUTIC PRODUCTS
ALL OTHER THERAPEUTIC PRODUCTS
Antidotes
CHEBI has role CHEBI:74530 antidote to curare poisoning
CHEBI has role CHEBI:51068 miotic
MeSH PA D018678 Cholinergic Agents
MeSH PA D002800 Cholinesterase Inhibitors
MeSH PA D004791 Enzyme Inhibitors
MeSH PA D008916 Miotics
MeSH PA D018377 Neurotransmitter Agents
MeSH PA D018373 Peripheral Nervous System Agents

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Open-angle glaucoma indication 84494001 DOID:1067
Anticholinergic Toxicity indication
Secondary glaucoma off-label use 95717004
Angle-closure glaucoma off-label use 392291006 DOID:13550
Hereditary Ataxias off-label use
Keratitis contraindication 5888003 DOID:4677
Urinary tract obstruction contraindication 7163005 DOID:5200
Parkinsonism contraindication 32798002
Gangrene contraindication 36024000
Retinal detachment contraindication 42059000 DOID:5327
Bradycardia contraindication 48867003
Disorder of cardiovascular system contraindication 49601007 DOID:1287
Neuromuscular block, function contraindication 55394004
Iritis contraindication 65074000 DOID:1406
Diabetes mellitus contraindication 73211009 DOID:9351
Epilepsy contraindication 84757009 DOID:1826
Gastrointestinal obstruction contraindication 126765001
Asthma contraindication 195967001 DOID:2841
Anterior uveitis contraindication 410692006 DOID:1407
Pupillary Block Glaucoma contraindication

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 13.89 acidic
pKa2 8.15 Basic
pKa3 2.09 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
Acetylcholinesterase Enzyme INHIBITOR IC50 9.37 CHEMBL IUPHAR
Cholinesterase Enzyme Ki 5.30 CHEMBL
Cytochrome P450 2D6 Enzyme IC50 6.70 DRUG MATRIX
Acetylcholinesterase Enzyme IC50 7.52 CHEMBL
Acetylcholinesterase Enzyme IC50 7.96 CHEMBL
Acetylcholinesterase Enzyme Ki 7.47 CHEMBL
Acetylcholinesterase Unclassified IC50 7.70 CHEMBL
Acetylcholinesterase Enzyme IC50 9.17 CHEMBL
Acetylcholinesterase Enzyme IC50 9.17 CHEMBL
Butyrylcholinesterase; Protein Bche Enzyme IC50 8.12 CHEMBL
Cholinesterase Enzyme IC50 6.55 CHEMBL
Cholinesterase Enzyme Ki 7.39 CHEMBL
Muscarinic acetylcholine receptor M1 GPCR IC50 4.43 CHEMBL
Butyrylcholinesterase Enzyme IC50 7.80 CHEMBL

External reference:

IDSource
4019894 VUID
N0000147979 NUI
C0031849 UMLSCUI
D00196 KEGG_DRUG
2046ZRO9VU UNII
57-64-7 SECONDARY_CAS_RN
85429009 SNOMEDCT_US
4019894 VANDF
8299 RXNORM
373347005 SNOMEDCT_US
d00342 MMSL
001700 NDDF
CHEBI:27953 CHEBI
CHEMBL94 ChEMBL_ID
CHEMBL338975 ChEMBL_ID
DB00981 DRUGBANK_ID
5983 PUBCHEM_CID
D010830 MESH_DESCRIPTOR_UI
6598 IUPHAR_LIGAND_ID
C026718 MESH_SUPPLEMENTAL_RECORD_UI

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Physostigmine Salicylate HUMAN PRESCRIPTION DRUG LABEL 1 17478-510 INJECTION 1 mg INTRAVENOUS unapproved drug other 13 sections
Physostigmine Salicylate HUMAN PRESCRIPTION DRUG LABEL 1 50090-4406 INJECTION 1 mg INTRAVENOUS unapproved drug other 14 sections
PHYSOSTIGMINE SALICYLATE HUMAN PRESCRIPTION DRUG LABEL 1 51662-1439 INJECTION 1 mg INTRAVENOUS unapproved drug other 13 sections
PHYSOSTIGMINE SALICYLATE HUMAN PRESCRIPTION DRUG LABEL 1 52584-510 INJECTION 1 mg INTRAVENOUS unapproved drug other 14 sections
Physostigmine Salicylate HUMAN PRESCRIPTION DRUG LABEL 1 71872-7074 INJECTION 1 mg INTRAVENOUS unapproved drug other 13 sections