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Details

Stereochemistry ABSOLUTE
Molecular Formula C15H21N3O2.C7H6O3
Molecular Weight 413.4669
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PHYSOSTIGMINE SALICYLATE

SMILES

OC(=O)C1=CC=CC=C1O.CNC(=O)OC2=CC=C3N(C)[C@H]4N(C)CC[C@@]4(C)C3=C2

InChI

InChIKey=HZOTZTANVBDFOF-PBCQUBLHSA-N
InChI=1S/C15H21N3O2.C7H6O3/c1-15-7-8-17(3)13(15)18(4)12-6-5-10(9-11(12)15)20-14(19)16-2;8-6-4-2-1-3-5(6)7(9)10/h5-6,9,13H,7-8H2,1-4H3,(H,16,19);1-4,8H,(H,9,10)/t13-,15+;/m1./s1

HIDE SMILES / InChI

Molecular Formula C7H6O3
Molecular Weight 138.1207
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C15H21N3O2
Molecular Weight 275.3461
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Physostigmine (Phy) is one of the oldest drug isolated from Calabar beans and successfully used for the treatment of glaucoma in 1864. Since then, it has been widely employed for various therapeutic purposes. Recently, it has gained prominence because of its clinical trials in the treatment of Alzheimer's disease. Physostigmine was used to treat glaucoma. It can be applied topically to the conjunctiva. Phy is also considered to be a potent prophylactic antidote for organophosphate poisoning. It is a reversible cholinesterase (ChE) inhibitor and has a short duration of action. For the last 50 years, numerous authors have shown that pretreatment with Phy would rapidly improve the incapacitating effects of organophosphate intoxication in various animal species. Phy carbamylates to a portion of ChE enzyme and thus protects the enzyme from binding with organophosphate, which are irreversible ChE inhibitors. The carbamylated ChE enzyme decarbamylates to free the enzyme for normal functioning. The rates of decarbamylation of butyrylcholinesterase (BuChE) in plasma and ChE in brain and muscle are different and are related to the half-life of Phy in these tissues. In addition to ChE inhibition, Phy has a direct action on acetylcholine (ACh) receptor ionophore complex by interacting with the ACh-gated cation channels. A cholinesterase inhibitor that is rapidly absorbed through membranes. 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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Physostigmine. Its use in acute anticholinergic syndrome with antidepressant and antiparkinson drugs.
1975 Mar
On the anticataleptic action of cyproheptadine.
1976 Aug
Donepezil hydrochloride: a treatment drug for Alzheimer's disease.
2001
Involvement of cholinergic mechanisms in the central control of respiration in the cane toad, Bufo marinus.
2001 Apr
[Anticholinergic syndrome after postoperative dimenhydrinate administration].
2001 Dec
Quantitative measurement of cerebral acetylcholinesterase using.
2001 Feb
Physostigmine versus diazepines for anticholinergic poisoning.
2001 Feb
Dehydroevodiamine attenuates beta-amyloid peptide-induced amnesia in mice.
2001 Feb 16
Effects of p-chlorophenylalanine on striatal acetylcholinesterase activity and on biogenic amine levels in nuclei raphe and caudate-putamen during physostigmine-induced tremor in rats.
2001 Feb 16
Synthesis of the signal molecule acetylcholine during the developmental cycle of Paramecium primaurelia (Protista, Ciliophora) and its possible function in conjugation.
2001 Jun
N-tert-butyl-alpha-phenylnitrone, a free radical scavenger with anticholinesterase activity does not improve the cognitive performance of scopolamine-challenged rats.
2001 Jun
Reversal of morphine-induced memory impairment in mice by withdrawal in Morris water maze: possible involvement of cholinergic system.
2001 Mar
A rat mammary tumor model induced by the organophosphorous pesticides parathion and malathion, possibly through acetylcholinesterase inhibition.
2001 May
Electrophysiological characterization of laminar synaptic inputs to the olfactory tubercle of the rat studied in vitro: modulation of glutamatergic transmission by cholinergic agents is pathway-specific.
2001 May
Physostigmine as treatment for severe CNS anticholinergic toxicity.
2001 Sep
The use of physostigmine in the management of gamma-hydroxybutyrate overdose.
2001 Sep
Use of physostigmine in the management of gamma-hydroxybutyrate overdose.
2001 Sep
Release of non-neuronal acetylcholine from the human placenta: difference to neuronal acetylcholine.
2001 Sep
Acetylcholine mediates the estrogen-induced increase in NMDA receptor binding in CA1 of the hippocampus and the associated improvement in working memory.
2001 Sep 1
Doxepin-induced torsade de pointes tachycardia.
2001 Sep 4
Eptastigmine: ten years of pharmacology, toxicology, pharmacokinetic, and clinical studies.
2001 Winter
Donepezil for Alzheimer's disease: pharmacodynamic, pharmacokinetic, and clinical profiles.
2001 Winter
Efficient formal total synthesis of physostigmine and physovenine: conformational analysis of key intermediates.
2002 Feb
Mechanism of vascular relaxation by cholinomimetic drugs with special reference to pilocarpine and arecoline.
2002 Feb
Physostigmine, sodium bicarbonate, or hypertonic saline to treat diphenhydramine toxicity.
2002 Feb
Heterogeneity of release-inhibiting muscarinic autoreceptors in heart atria and urinary bladder: a study with M(2)- and M(4)-receptor-deficient mice.
2002 Feb
Pharmacological properties of nicotinic acetylcholine receptors in isolated Locusta migratoria neurones.
2002 Feb 15
Alternative splicing and neuritic mRNA translocation under long-term neuronal hypersensitivity.
2002 Jan 18
Physostigmine does not antagonize sevoflurane anesthesia assessed by bispectral index or enhances recovery.
2002 Mar
Patents

Sample Use Guides

For glaucoma: Adults and children—Use in each eye one to three times a day.
Route of Administration: Other
The increased number of BrdU- and proliferating cell nuclear antigen-labeled cells were shown in zebrafish treated with 200 μM physostigmine, which was inhibited by pretreatment with 200 μM scopolamine. iNOS mRNA expression was increased in the brain of zebrafish treated with 200 μM physostigmine. Consistently, aminoguanidine, an iNOS inhibitor, attenuated the increase in the number of BrdU-labeled cells by physostigmine treatment. Zebrafish also showed seizure-like locomotor activity characterized by a rapid and abrupt movement during a 30 min treatment with 200 μM physostigmine. Neural activity in response to an electrical stimulus was increased in the isolated telencephalon of zebrafish continuously perfused with 200 μM physostigmine.
Substance Class Chemical
Created
by admin
on Mon Mar 31 17:52:47 GMT 2025
Edited
by admin
on Mon Mar 31 17:52:47 GMT 2025
Record UNII
2046ZRO9VU
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ANTILIRIUM
Preferred Name English
PHYSOSTIGMINE SALICYLATE
EP   JAN   MART.   MI   USP   USP-RS   VANDF   WHO-DD   WHO-IP  
Common Name English
PHYSOSTIGMINI SALICYLAS [WHO-IP LATIN]
Common Name English
PHYSOSTIGMINE SALICYLATE [MI]
Common Name English
PHYSOSTIGMINE SALICYLATE [WHO-IP]
Common Name English
PHYSOSTIGMINE SALICYLATE [VANDF]
Common Name English
PHYSOSTIGMINE SALICYLATE [MART.]
Common Name English
PHYSOSTIGMINE SALICYLATE [USP-RS]
Common Name English
ISOPTO ESERINE
Common Name English
NSC-757275
Code English
ESERINE SALICYLATE
Common Name English
Physostigmine monosalicylate
Common Name English
PYRROLO(2,3-B)INDOL-5-OL, 1,2,3,3A,8,8A-HEXAHYDRO-1,3A,8-TRIMETHYL-, METHYLCARBAMATE (ESTER), (3AS-CIS)-, MONO(2-HYDROXYBENZOATE)
Common Name English
PHYSOSTIGMINE SALICYLATE [EP MONOGRAPH]
Common Name English
PHYSOSTIGMINE SALICYLATE [JAN]
Common Name English
PHYSOSTIGMINE SALICYLATE [USP MONOGRAPH]
Common Name English
Physostigmine salicylate [WHO-DD]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C47792
Created by admin on Mon Mar 31 17:52:47 GMT 2025 , Edited by admin on Mon Mar 31 17:52:47 GMT 2025
FDA ORPHAN DRUG 183
Created by admin on Mon Mar 31 17:52:47 GMT 2025 , Edited by admin on Mon Mar 31 17:52:47 GMT 2025
Code System Code Type Description
CHEBI
27953
Created by admin on Mon Mar 31 17:52:47 GMT 2025 , Edited by admin on Mon Mar 31 17:52:47 GMT 2025
PRIMARY
DRUG BANK
DBSALT001541
Created by admin on Mon Mar 31 17:52:47 GMT 2025 , Edited by admin on Mon Mar 31 17:52:47 GMT 2025
PRIMARY
RS_ITEM_NUM
1537003
Created by admin on Mon Mar 31 17:52:47 GMT 2025 , Edited by admin on Mon Mar 31 17:52:47 GMT 2025
PRIMARY
ChEMBL
CHEMBL94
Created by admin on Mon Mar 31 17:52:47 GMT 2025 , Edited by admin on Mon Mar 31 17:52:47 GMT 2025
PRIMARY
DAILYMED
2046ZRO9VU
Created by admin on Mon Mar 31 17:52:47 GMT 2025 , Edited by admin on Mon Mar 31 17:52:47 GMT 2025
PRIMARY
CAS
57-64-7
Created by admin on Mon Mar 31 17:52:47 GMT 2025 , Edited by admin on Mon Mar 31 17:52:47 GMT 2025
PRIMARY
NSC
757275
Created by admin on Mon Mar 31 17:52:47 GMT 2025 , Edited by admin on Mon Mar 31 17:52:47 GMT 2025
PRIMARY
MESH
C026718
Created by admin on Mon Mar 31 17:52:47 GMT 2025 , Edited by admin on Mon Mar 31 17:52:47 GMT 2025
PRIMARY
ECHA (EC/EINECS)
200-343-8
Created by admin on Mon Mar 31 17:52:47 GMT 2025 , Edited by admin on Mon Mar 31 17:52:47 GMT 2025
PRIMARY
RXCUI
33656
Created by admin on Mon Mar 31 17:52:47 GMT 2025 , Edited by admin on Mon Mar 31 17:52:47 GMT 2025
PRIMARY RxNorm
EPA CompTox
DTXSID80883232
Created by admin on Mon Mar 31 17:52:47 GMT 2025 , Edited by admin on Mon Mar 31 17:52:47 GMT 2025
PRIMARY
MERCK INDEX
m8766
Created by admin on Mon Mar 31 17:52:47 GMT 2025 , Edited by admin on Mon Mar 31 17:52:47 GMT 2025
PRIMARY Merck Index
SMS_ID
100000079464
Created by admin on Mon Mar 31 17:52:47 GMT 2025 , Edited by admin on Mon Mar 31 17:52:47 GMT 2025
PRIMARY
NCI_THESAURUS
C81336
Created by admin on Mon Mar 31 17:52:47 GMT 2025 , Edited by admin on Mon Mar 31 17:52:47 GMT 2025
PRIMARY
FDA UNII
2046ZRO9VU
Created by admin on Mon Mar 31 17:52:47 GMT 2025 , Edited by admin on Mon Mar 31 17:52:47 GMT 2025
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
PHYSOSTIGMINE SALICYLATE
Created by admin on Mon Mar 31 17:52:47 GMT 2025 , Edited by admin on Mon Mar 31 17:52:47 GMT 2025
PRIMARY Description: Colourless crystals; odourless. Solubility: Sparingly soluble in water; soluble in ethanol (~750 g/l) TS; slightly soluble in ether R. Category: Anticholinesterase; miotic. Storage: Physostigmine salicylate should be kept in a tightly closed container, protected from light, and preferably in quantitiesnot exceeding 1 g. Additional information: Physostigmine salicylate is very poisonous. It acquires a red tint when exposed to air or light. All testsshould be performed on freshly prepared solutions. Definition: Physostigmine salicylate contains not less than 98.0% and not more than 101.0% of C15H21N3O2,C7H6O3, calculatedwith reference to the dried substance.
PUBCHEM
5992
Created by admin on Mon Mar 31 17:52:47 GMT 2025 , Edited by admin on Mon Mar 31 17:52:47 GMT 2025
PRIMARY
EVMPD
SUB14865MIG
Created by admin on Mon Mar 31 17:52:47 GMT 2025 , Edited by admin on Mon Mar 31 17:52:47 GMT 2025
PRIMARY
CHEBI
48883
Created by admin on Mon Mar 31 17:52:47 GMT 2025 , Edited by admin on Mon Mar 31 17:52:47 GMT 2025
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY