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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=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

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
Evidence for a direct cholinergic involvement in the scopolamine-induced amnesia in monkeys: effects of concurrent administration of physostigmine and methylphenidate with scopolamine.
1978 Dec
Mechanisms associated with methiocarb resistance in Frankliniella occidentalis (Thysanoptera: Thripidae).
2000 Apr
Effects of serotoninergic drugs on tremor induced by physostigmine in rats.
2000 May
Donepezil hydrochloride: a treatment drug for Alzheimer's disease.
2001
Physostigmine for Alzheimer's disease.
2001
Influence of nitric oxide donors and of the alpha(2)-agonist UK-14,304 on acetylcholine release in the pig gastric fundus.
2001
Action of tacrine on muscarinic receptors in rat intestinal smooth muscle.
2001 Apr
Compensatory mechanisms enhance hippocampal acetylcholine release in transgenic mice expressing human acetylcholinesterase.
2001 Apr
Soluble and membrane-bound acetylcholinesterases in Mytilus galloprovincialis (Pelecypoda: Filibranchia) from the northern Adriatic sea.
2001 Apr 16
[Anticholinergic syndrome after postoperative dimenhydrinate administration].
2001 Dec
Acetylcholinesterase blockade does not account for the adverse cardiovascular effects of the antitumor drug irinotecan: a preclinical study.
2001 Dec 1
Functional relationship between subfornical organ cholinergic stimulation and cellular activation in the hypothalamus and AV3V region.
2001 Dec 20
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
Nasal administration of a physostigmine analogue (NXX-066) for Alzheimer's disease to rats.
2001 Jan 16
Hexahydrochromeno[4,3-b]pyrrole derivatives as acetylcholinesterase inhibitors.
2001 Jan 4
Aldrin-induced locomotor activity: possible involvement of the central GABAergic-cholinergic-dopaminergic interaction.
2001 Jan-Feb
Oxidative and hydrolytic properties of beta-amyloid.
2001 Jun
Physostigmine and cognition in schizotypal personality disorder.
2001 Mar 1
A rat mammary tumor model induced by the organophosphorous pesticides parathion and malathion, possibly through acetylcholinesterase inhibition.
2001 May
Subchronic administration of various pretreatments of nerve agent poisoning. I. Protection of blood and central cholinesterases, innocuousness towards blood-brain barrier permeability.
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
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
Involvement of cholinergic and glutamatergic functions in working memory impairment induced by interleukin-1beta in rats.
2001 Nov 2
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 esterase-like activity of serum albumin may be due to cholinesterase contamination.
2001 Oct
Synthesis, hydrolysis kinetics and anti-platelet effects of isosorbide mononitrate derivatives of aspirin.
2001 Oct
Memory improving actions of gabapentin in mice: possible involvement of central muscarinic cholinergic mechanism.
2001 Oct 5
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
Doxepin-induced torsade de pointes tachycardia.
2001 Sep 4
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
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 Wed Jul 05 22:48:11 UTC 2023
Edited
by admin
on Wed Jul 05 22:48:11 UTC 2023
Record UNII
2046ZRO9VU
Record Status Validated (UNII)
Record Version
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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 Wed Jul 05 22:48:11 UTC 2023 , Edited by admin on Wed Jul 05 22:48:11 UTC 2023
FDA ORPHAN DRUG 183
Created by admin on Wed Jul 05 22:48:11 UTC 2023 , Edited by admin on Wed Jul 05 22:48:11 UTC 2023
Code System Code Type Description
CHEBI
27953
Created by admin on Wed Jul 05 22:48:11 UTC 2023 , Edited by admin on Wed Jul 05 22:48:11 UTC 2023
PRIMARY
DRUG BANK
DBSALT001541
Created by admin on Wed Jul 05 22:48:11 UTC 2023 , Edited by admin on Wed Jul 05 22:48:11 UTC 2023
PRIMARY
RS_ITEM_NUM
1537003
Created by admin on Wed Jul 05 22:48:11 UTC 2023 , Edited by admin on Wed Jul 05 22:48:11 UTC 2023
PRIMARY
ChEMBL
CHEMBL94
Created by admin on Wed Jul 05 22:48:11 UTC 2023 , Edited by admin on Wed Jul 05 22:48:11 UTC 2023
PRIMARY
DAILYMED
2046ZRO9VU
Created by admin on Wed Jul 05 22:48:11 UTC 2023 , Edited by admin on Wed Jul 05 22:48:11 UTC 2023
PRIMARY
CAS
57-64-7
Created by admin on Wed Jul 05 22:48:11 UTC 2023 , Edited by admin on Wed Jul 05 22:48:11 UTC 2023
PRIMARY
NSC
757275
Created by admin on Wed Jul 05 22:48:11 UTC 2023 , Edited by admin on Wed Jul 05 22:48:11 UTC 2023
PRIMARY
MESH
C026718
Created by admin on Wed Jul 05 22:48:11 UTC 2023 , Edited by admin on Wed Jul 05 22:48:11 UTC 2023
PRIMARY
ECHA (EC/EINECS)
200-343-8
Created by admin on Wed Jul 05 22:48:11 UTC 2023 , Edited by admin on Wed Jul 05 22:48:11 UTC 2023
PRIMARY
RXCUI
33656
Created by admin on Wed Jul 05 22:48:11 UTC 2023 , Edited by admin on Wed Jul 05 22:48:11 UTC 2023
PRIMARY RxNorm
EPA CompTox
DTXSID80883232
Created by admin on Wed Jul 05 22:48:11 UTC 2023 , Edited by admin on Wed Jul 05 22:48:11 UTC 2023
PRIMARY
MERCK INDEX
M8766
Created by admin on Wed Jul 05 22:48:11 UTC 2023 , Edited by admin on Wed Jul 05 22:48:11 UTC 2023
PRIMARY Merck Index
SMS_ID
100000079464
Created by admin on Wed Jul 05 22:48:11 UTC 2023 , Edited by admin on Wed Jul 05 22:48:11 UTC 2023
PRIMARY
NCI_THESAURUS
C81336
Created by admin on Wed Jul 05 22:48:11 UTC 2023 , Edited by admin on Wed Jul 05 22:48:11 UTC 2023
PRIMARY
FDA UNII
2046ZRO9VU
Created by admin on Wed Jul 05 22:48:11 UTC 2023 , Edited by admin on Wed Jul 05 22:48:11 UTC 2023
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
PHYSOSTIGMINE SALICYLATE
Created by admin on Wed Jul 05 22:48:11 UTC 2023 , Edited by admin on Wed Jul 05 22:48:11 UTC 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 Wed Jul 05 22:48:11 UTC 2023 , Edited by admin on Wed Jul 05 22:48:11 UTC 2023
PRIMARY
EVMPD
SUB14865MIG
Created by admin on Wed Jul 05 22:48:11 UTC 2023 , Edited by admin on Wed Jul 05 22:48:11 UTC 2023
PRIMARY
CHEBI
48883
Created by admin on Wed Jul 05 22:48:11 UTC 2023 , Edited by admin on Wed Jul 05 22:48:11 UTC 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY