U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS
This repository is under review for potential modification in compliance with Administration directives.

Details

Stereochemistry ABSOLUTE
Molecular Formula C15H21N3O2
Molecular Weight 275.3461
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of Physostigmine

SMILES

CNC(=O)OC1=CC=C2N(C)[C@H]3N(C)CC[C@@]3(C)C2=C1

InChI

InChIKey=PIJVFDBKTWXHHD-HIFRSBDPSA-N
InChI=1S/C15H21N3O2/c1-15-7-8-17(3)13(15)18(4)12-6-5-10(9-11(12)15)20-14(19)16-2/h5-6,9,13H,7-8H2,1-4H3,(H,16,19)/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
On the anticataleptic action of cyproheptadine.
1976 Aug
[Etiology of initially unexplained confusion of excitability in deadly nightshade poisoning with suicidal intent. Symptoms, differential diagnosis, toxicology and physostigmine therapy of anticholinergic syndrome].
2000 Nov 10
Donepezil hydrochloride: a treatment drug 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
Involvement of cholinergic mechanisms in the central control of respiration in the cane toad, Bufo marinus.
2001 Apr
Endogenous acetylcholine facilitates epileptogenesis in immature rat neocortex.
2001 Apr 13
Stimulation of minor salivary glands by intraoral treatment with the cholinesterase inhibitor physostigmine in man.
2001 Dec
Functional relationship between subfornical organ cholinergic stimulation and cellular activation in the hypothalamus and AV3V region.
2001 Dec 20
Acute toxicity screening of novel AChE inhibitors using neuronal networks on microelectrode arrays.
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
Sexual diergism in rat hypothalamic-pituitary-adrenal axis responses to cholinergic stimulation and antagonism.
2001 Jan 1
Viral neuroinvasion as a marker for BBB integrity following exposure to cholinesterase inhibitors.
2001 Jan 19
The effect of betahistine on vestibular habituation: comparison of rotatory and sway habituation training.
2001 Jul
Septal GABAergic and hippocampal cholinergic systems modulate anxiety in the plus-maze and shock-probe tests.
2001 Jul-Aug
Physostigmine and cognition in schizotypal personality disorder.
2001 Mar 1
Factors that determine acetylcholine responsiveness of guinea pig tracheal tubes.
2001 May 25
Concurrent quantification of tremor and depression of locomotor activity induced in rats by harmaline and physostigmine.
2001 Nov
Methyl analogues of the experimental Alzheimer drug phenserine: synthesis and structure/activity relationships for acetyl- and butyrylcholinesterase inhibitory action.
2001 Nov 22
The esterase-like activity of serum albumin may be due to cholinesterase contamination.
2001 Oct
The combined effects of pyridostigmine and chronic stress on brain cortical and blood acetylcholinesterase, corticosterone, prolactin and alternation performance in rats.
2001 Oct-Nov
Developmental neurotoxicity of chlorpyrifos modeled in vitro: comparative effects of metabolites and other cholinesterase inhibitors on DNA synthesis in PC12 and C6 cells.
2001 Sep
Physostigmine as treatment for severe CNS anticholinergic toxicity.
2001 Sep
The use of carbamates, atropine, and 2-pyridine aldoxime methoiodide in the protection of Artemia salina against poisoning by carbophenothion.
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
Efficient formal total synthesis of physostigmine and physovenine: conformational analysis of key intermediates.
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
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
HSDB   MART.   MI   USP   VANDF   WHO-DD  
Common Name English
ESERINUM
HPUS  
Preferred Name English
PHYSOSTIGMINE [MI]
Common Name English
NSC-30782
Code English
ESERIN
Common Name English
PHYSOSTIGMINE [USP IMPURITY]
Common Name English
ESERINUM [HPUS]
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)
Common Name English
Physostigmine [WHO-DD]
Common Name English
PHYSOSTIGMINE [HSDB]
Common Name English
1,2,3,3A.BETA.,8A.BETA.-HEXAHYDRO-1,3A,8-TRIMETHYLPYRROLO(2,3-B)-INDOL-5-YL METHYLCARBAMATE
Common Name English
MCV-4484
Code English
(-)-PHYSOSTIGMINE
Common Name English
PHYSOSTIGMINE [VANDF]
Common Name English
PHYSOSTIGMINE [MART.]
Common Name English
COGMINE
Brand Name English
ESERINE
Common Name English
Classification Tree Code System Code
WHO-VATC QS01EB05
Created by admin on Mon Mar 31 17:35:21 GMT 2025 , Edited by admin on Mon Mar 31 17:35:21 GMT 2025
WHO-ATC S01EB05
Created by admin on Mon Mar 31 17:35:21 GMT 2025 , Edited by admin on Mon Mar 31 17:35:21 GMT 2025
NCI_THESAURUS C47792
Created by admin on Mon Mar 31 17:35:21 GMT 2025 , Edited by admin on Mon Mar 31 17:35:21 GMT 2025
WHO-VATC QA03FA90
Created by admin on Mon Mar 31 17:35:21 GMT 2025 , Edited by admin on Mon Mar 31 17:35:21 GMT 2025
WHO-VATC QA03AX90
Created by admin on Mon Mar 31 17:35:21 GMT 2025 , Edited by admin on Mon Mar 31 17:35:21 GMT 2025
WHO-VATC QV03AB19
Created by admin on Mon Mar 31 17:35:21 GMT 2025 , Edited by admin on Mon Mar 31 17:35:21 GMT 2025
LIVERTOX 776
Created by admin on Mon Mar 31 17:35:21 GMT 2025 , Edited by admin on Mon Mar 31 17:35:21 GMT 2025
WHO-ATC V03AB19
Created by admin on Mon Mar 31 17:35:21 GMT 2025 , Edited by admin on Mon Mar 31 17:35:21 GMT 2025
Code System Code Type Description
HSDB
3161
Created by admin on Mon Mar 31 17:35:21 GMT 2025 , Edited by admin on Mon Mar 31 17:35:21 GMT 2025
PRIMARY
DAILYMED
9U1VM840SP
Created by admin on Mon Mar 31 17:35:21 GMT 2025 , Edited by admin on Mon Mar 31 17:35:21 GMT 2025
PRIMARY
CHEBI
27953
Created by admin on Mon Mar 31 17:35:21 GMT 2025 , Edited by admin on Mon Mar 31 17:35:21 GMT 2025
PRIMARY
SMS_ID
100000079444
Created by admin on Mon Mar 31 17:35:21 GMT 2025 , Edited by admin on Mon Mar 31 17:35:21 GMT 2025
PRIMARY
FDA UNII
9U1VM840SP
Created by admin on Mon Mar 31 17:35:21 GMT 2025 , Edited by admin on Mon Mar 31 17:35:21 GMT 2025
PRIMARY
EPA CompTox
DTXSID3023471
Created by admin on Mon Mar 31 17:35:21 GMT 2025 , Edited by admin on Mon Mar 31 17:35:21 GMT 2025
PRIMARY
CAS
57-47-6
Created by admin on Mon Mar 31 17:35:21 GMT 2025 , Edited by admin on Mon Mar 31 17:35:21 GMT 2025
PRIMARY
MESH
D010830
Created by admin on Mon Mar 31 17:35:21 GMT 2025 , Edited by admin on Mon Mar 31 17:35:21 GMT 2025
PRIMARY
IUPHAR
6598
Created by admin on Mon Mar 31 17:35:21 GMT 2025 , Edited by admin on Mon Mar 31 17:35:21 GMT 2025
PRIMARY
LACTMED
Physostigmine
Created by admin on Mon Mar 31 17:35:21 GMT 2025 , Edited by admin on Mon Mar 31 17:35:21 GMT 2025
PRIMARY
DRUG CENTRAL
2159
Created by admin on Mon Mar 31 17:35:21 GMT 2025 , Edited by admin on Mon Mar 31 17:35:21 GMT 2025
PRIMARY
ChEMBL
CHEMBL94
Created by admin on Mon Mar 31 17:35:21 GMT 2025 , Edited by admin on Mon Mar 31 17:35:21 GMT 2025
PRIMARY
MERCK INDEX
m8766
Created by admin on Mon Mar 31 17:35:21 GMT 2025 , Edited by admin on Mon Mar 31 17:35:21 GMT 2025
PRIMARY Merck Index
PUBCHEM
5983
Created by admin on Mon Mar 31 17:35:21 GMT 2025 , Edited by admin on Mon Mar 31 17:35:21 GMT 2025
PRIMARY
WIKIPEDIA
PHYSOSTIGMINE
Created by admin on Mon Mar 31 17:35:21 GMT 2025 , Edited by admin on Mon Mar 31 17:35:21 GMT 2025
PRIMARY
NSC
30782
Created by admin on Mon Mar 31 17:35:21 GMT 2025 , Edited by admin on Mon Mar 31 17:35:21 GMT 2025
PRIMARY
ECHA (EC/EINECS)
200-332-8
Created by admin on Mon Mar 31 17:35:21 GMT 2025 , Edited by admin on Mon Mar 31 17:35:21 GMT 2025
PRIMARY
RXCUI
8299
Created by admin on Mon Mar 31 17:35:21 GMT 2025 , Edited by admin on Mon Mar 31 17:35:21 GMT 2025
PRIMARY RxNorm
DRUG BANK
DB00981
Created by admin on Mon Mar 31 17:35:21 GMT 2025 , Edited by admin on Mon Mar 31 17:35:21 GMT 2025
PRIMARY
EVMPD
SUB14864MIG
Created by admin on Mon Mar 31 17:35:21 GMT 2025 , Edited by admin on Mon Mar 31 17:35:21 GMT 2025
PRIMARY
NCI_THESAURUS
C81337
Created by admin on Mon Mar 31 17:35:21 GMT 2025 , Edited by admin on Mon Mar 31 17:35:21 GMT 2025
PRIMARY