U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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=C(O)C=CC=C1.[H][C@]23N(C)CC[C@@]2(C)C4=C(C=CC(OC(=O)NC)=C4)N3C

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
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
Physostigmine salicylate in the treatment of tricyclic antidepressant overdosage.
1975 Mar 3
Mechanisms associated with methiocarb resistance in Frankliniella occidentalis (Thysanoptera: Thripidae).
2000 Apr
Influence of nitric oxide donors and of the alpha(2)-agonist UK-14,304 on acetylcholine release in the pig gastric fundus.
2001
Age-related effects of chlorpyrifos on acetylcholine release in rat brain.
2001 Feb
Acute toxicity screening of novel AChE inhibitors using neuronal networks on microelectrode arrays.
2001 Feb
Acetylcholinesterase inhibition increases in vivo N-(2-[18F]fluoroethyl)-4-piperidyl benzilate binding to muscarinic acetylcholine receptors.
2001 Feb
Quantitative measurement of cerebral acetylcholinesterase using.
2001 Feb
Gamma-hydroxybutyrate overdose and physostigmine: teaching new tricks to an old drug?
2001 Jan
Aldrin-induced locomotor activity: possible involvement of the central GABAergic-cholinergic-dopaminergic interaction.
2001 Jan-Feb
The effect of betahistine on vestibular habituation: comparison of rotatory and sway habituation training.
2001 Jul
Photoactivatable alpha-conotoxins reveal contacts with all subunits as well as antagonist-induced rearrangements in the Torpedo californica acetylcholine receptor.
2001 Jul
Synthesis of the signal molecule acetylcholine during the developmental cycle of Paramecium primaurelia (Protista, Ciliophora) and its possible function in conjugation.
2001 Jun
Oxidative and hydrolytic properties of beta-amyloid.
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
Central and peripheral activity of cholinesterase inhibitors as revealed by yawning and fasciculation in rats.
2001 Mar
Effects of right and left vagal stimulation on left ventricular acetylcholine levels in the cat.
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
Force spectroscopy between acetylcholine and single acetylcholinesterase molecules and the effects of inhibitors and reactivators studied by atomic force microscopy.
2001 May
Factors that determine acetylcholine responsiveness of guinea pig tracheal tubes.
2001 May 25
Estradiol decreases the acetylcholine-elicited airway reactivity in ovariectomized rats through an increase in epithelial acetylcholinesterase activity.
2001 Nov 15
Infusions of physostigmine into the hippocampus or the entorhinal cortex attenuate avoidance retention deficits produced by intra-septal infusions of the GABA agonist muscimol.
2001 Nov 30
The glutamate receptor agonist, AMPA, induces acetylcholine release in guinea pig cochlea; a microdialysis study.
2001 Oct 5
The combined effects of pyridostigmine and chronic stress on brain cortical and blood acetylcholinesterase, corticosterone, prolactin and alternation performance in rats.
2001 Oct-Nov
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
Mechanism of vascular relaxation by cholinomimetic drugs with special reference to pilocarpine and arecoline.
2002 Feb
Biochemical analysis of a native and proteolytic fragment of a high-molecular-weight thermostable lipase from a mesophilic Bacillus sp.
2002 Feb
Involvement of mu(1)-opioid receptors and cholinergic neurotransmission in the endomorphins-induced impairment of passive avoidance learning in mice.
2002 Feb 1
Alternative splicing and neuritic mRNA translocation under long-term neuronal hypersensitivity.
2002 Jan 18
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.
Name Type Language
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
ANTILIRIUM
Brand 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 Fri Dec 15 15:16:57 GMT 2023 , Edited by admin on Fri Dec 15 15:16:57 GMT 2023
FDA ORPHAN DRUG 183
Created by admin on Fri Dec 15 15:16:57 GMT 2023 , Edited by admin on Fri Dec 15 15:16:57 GMT 2023
Code System Code Type Description
CHEBI
27953
Created by admin on Fri Dec 15 15:16:57 GMT 2023 , Edited by admin on Fri Dec 15 15:16:57 GMT 2023
PRIMARY
DRUG BANK
DBSALT001541
Created by admin on Fri Dec 15 15:16:57 GMT 2023 , Edited by admin on Fri Dec 15 15:16:57 GMT 2023
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RS_ITEM_NUM
1537003
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ChEMBL
CHEMBL94
Created by admin on Fri Dec 15 15:16:57 GMT 2023 , Edited by admin on Fri Dec 15 15:16:57 GMT 2023
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DAILYMED
2046ZRO9VU
Created by admin on Fri Dec 15 15:16:57 GMT 2023 , Edited by admin on Fri Dec 15 15:16:57 GMT 2023
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CAS
57-64-7
Created by admin on Fri Dec 15 15:16:57 GMT 2023 , Edited by admin on Fri Dec 15 15:16:57 GMT 2023
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NSC
757275
Created by admin on Fri Dec 15 15:16:57 GMT 2023 , Edited by admin on Fri Dec 15 15:16:57 GMT 2023
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MESH
C026718
Created by admin on Fri Dec 15 15:16:57 GMT 2023 , Edited by admin on Fri Dec 15 15:16:57 GMT 2023
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ECHA (EC/EINECS)
200-343-8
Created by admin on Fri Dec 15 15:16:57 GMT 2023 , Edited by admin on Fri Dec 15 15:16:57 GMT 2023
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RXCUI
33656
Created by admin on Fri Dec 15 15:16:57 GMT 2023 , Edited by admin on Fri Dec 15 15:16:57 GMT 2023
PRIMARY RxNorm
EPA CompTox
DTXSID80883232
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MERCK INDEX
m8766
Created by admin on Fri Dec 15 15:16:57 GMT 2023 , Edited by admin on Fri Dec 15 15:16:57 GMT 2023
PRIMARY Merck Index
SMS_ID
100000079464
Created by admin on Fri Dec 15 15:16:57 GMT 2023 , Edited by admin on Fri Dec 15 15:16:57 GMT 2023
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NCI_THESAURUS
C81336
Created by admin on Fri Dec 15 15:16:57 GMT 2023 , Edited by admin on Fri Dec 15 15:16:57 GMT 2023
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FDA UNII
2046ZRO9VU
Created by admin on Fri Dec 15 15:16:57 GMT 2023 , Edited by admin on Fri Dec 15 15:16:57 GMT 2023
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WHO INTERNATIONAL PHARMACOPEIA
PHYSOSTIGMINE SALICYLATE
Created by admin on Fri Dec 15 15:16:57 GMT 2023 , Edited by admin on Fri Dec 15 15:16:57 GMT 2023
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 Fri Dec 15 15:16:57 GMT 2023 , Edited by admin on Fri Dec 15 15:16:57 GMT 2023
PRIMARY
EVMPD
SUB14865MIG
Created by admin on Fri Dec 15 15:16:57 GMT 2023 , Edited by admin on Fri Dec 15 15:16:57 GMT 2023
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CHEBI
48883
Created by admin on Fri Dec 15 15:16:57 GMT 2023 , Edited by admin on Fri Dec 15 15:16:57 GMT 2023
PRIMARY