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
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
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/2676871
Sources: https://www.ncbi.nlm.nih.gov/pubmed/2676871
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.
CNS Activity
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL220 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1954303 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Palliative | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
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Physostigmine. Its use in acute anticholinergic syndrome with antidepressant and antiparkinson drugs. | 1975 Mar |
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Physostigmine salicylate in the treatment of tricyclic antidepressant overdosage. | 1975 Mar 3 |
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Mechanisms associated with methiocarb resistance in Frankliniella occidentalis (Thysanoptera: Thripidae). | 2000 Apr |
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Influence of nitric oxide donors and of the alpha(2)-agonist UK-14,304 on acetylcholine release in the pig gastric fundus. | 2001 |
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Age-related effects of chlorpyrifos on acetylcholine release in rat brain. | 2001 Feb |
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Acute toxicity screening of novel AChE inhibitors using neuronal networks on microelectrode arrays. | 2001 Feb |
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Acetylcholinesterase inhibition increases in vivo N-(2-[18F]fluoroethyl)-4-piperidyl benzilate binding to muscarinic acetylcholine receptors. | 2001 Feb |
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Quantitative measurement of cerebral acetylcholinesterase using. | 2001 Feb |
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Gamma-hydroxybutyrate overdose and physostigmine: teaching new tricks to an old drug? | 2001 Jan |
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Aldrin-induced locomotor activity: possible involvement of the central GABAergic-cholinergic-dopaminergic interaction. | 2001 Jan-Feb |
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The effect of betahistine on vestibular habituation: comparison of rotatory and sway habituation training. | 2001 Jul |
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Photoactivatable alpha-conotoxins reveal contacts with all subunits as well as antagonist-induced rearrangements in the Torpedo californica acetylcholine receptor. | 2001 Jul |
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Synthesis of the signal molecule acetylcholine during the developmental cycle of Paramecium primaurelia (Protista, Ciliophora) and its possible function in conjugation. | 2001 Jun |
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Oxidative and hydrolytic properties of beta-amyloid. | 2001 Jun |
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N-tert-butyl-alpha-phenylnitrone, a free radical scavenger with anticholinesterase activity does not improve the cognitive performance of scopolamine-challenged rats. | 2001 Jun |
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Central and peripheral activity of cholinesterase inhibitors as revealed by yawning and fasciculation in rats. | 2001 Mar |
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Effects of right and left vagal stimulation on left ventricular acetylcholine levels in the cat. | 2001 May |
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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 |
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Force spectroscopy between acetylcholine and single acetylcholinesterase molecules and the effects of inhibitors and reactivators studied by atomic force microscopy. | 2001 May |
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Factors that determine acetylcholine responsiveness of guinea pig tracheal tubes. | 2001 May 25 |
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Estradiol decreases the acetylcholine-elicited airway reactivity in ovariectomized rats through an increase in epithelial acetylcholinesterase activity. | 2001 Nov 15 |
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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 |
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The glutamate receptor agonist, AMPA, induces acetylcholine release in guinea pig cochlea; a microdialysis study. | 2001 Oct 5 |
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The combined effects of pyridostigmine and chronic stress on brain cortical and blood acetylcholinesterase, corticosterone, prolactin and alternation performance in rats. | 2001 Oct-Nov |
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The use of physostigmine in the management of gamma-hydroxybutyrate overdose. | 2001 Sep |
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Use of physostigmine in the management of gamma-hydroxybutyrate overdose. | 2001 Sep |
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Mechanism of vascular relaxation by cholinomimetic drugs with special reference to pilocarpine and arecoline. | 2002 Feb |
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Biochemical analysis of a native and proteolytic fragment of a high-molecular-weight thermostable lipase from a mesophilic Bacillus sp. | 2002 Feb |
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Involvement of mu(1)-opioid receptors and cholinergic neurotransmission in the endomorphins-induced impairment of passive avoidance learning in mice. | 2002 Feb 1 |
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Alternative splicing and neuritic mRNA translocation under long-term neuronal hypersensitivity. | 2002 Jan 18 |
Sample Use Guides
For glaucoma:
Adults and children—Use in each eye one to three times a day.
Route of Administration:
Other
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27378362
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.
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Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C47792
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FDA ORPHAN DRUG |
183
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27953
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DBSALT001541
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1537003
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CHEMBL94
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2046ZRO9VU
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57-64-7
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757275
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C026718
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200-343-8
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33656
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DTXSID80883232
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m8766
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100000079464
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C81336
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2046ZRO9VU
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PHYSOSTIGMINE SALICYLATE
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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. | ||
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5992
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SUB14865MIG
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48883
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ACTIVE MOIETY
PARENT (SALT/SOLVATE)
SUBSTANCE RECORD