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
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 |
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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On the anticataleptic action of cyproheptadine. | 1976 Aug |
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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 |
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Mechanisms associated with methiocarb resistance in Frankliniella occidentalis (Thysanoptera: Thripidae). | 2000 Apr |
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Effects of serotoninergic drugs on tremor induced by physostigmine in rats. | 2000 May |
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Donepezil hydrochloride: a treatment drug for Alzheimer's disease. | 2001 |
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Physostigmine for Alzheimer's disease. | 2001 |
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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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Action of tacrine on muscarinic receptors in rat intestinal smooth muscle. | 2001 Apr |
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Compensatory mechanisms enhance hippocampal acetylcholine release in transgenic mice expressing human acetylcholinesterase. | 2001 Apr |
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Soluble and membrane-bound acetylcholinesterases in Mytilus galloprovincialis (Pelecypoda: Filibranchia) from the northern Adriatic sea. | 2001 Apr 16 |
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[Anticholinergic syndrome after postoperative dimenhydrinate administration]. | 2001 Dec |
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Acetylcholinesterase blockade does not account for the adverse cardiovascular effects of the antitumor drug irinotecan: a preclinical study. | 2001 Dec 1 |
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Functional relationship between subfornical organ cholinergic stimulation and cellular activation in the hypothalamus and AV3V region. | 2001 Dec 20 |
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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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Nasal administration of a physostigmine analogue (NXX-066) for Alzheimer's disease to rats. | 2001 Jan 16 |
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Hexahydrochromeno[4,3-b]pyrrole derivatives as acetylcholinesterase inhibitors. | 2001 Jan 4 |
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Aldrin-induced locomotor activity: possible involvement of the central GABAergic-cholinergic-dopaminergic interaction. | 2001 Jan-Feb |
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Oxidative and hydrolytic properties of beta-amyloid. | 2001 Jun |
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Physostigmine and cognition in schizotypal personality disorder. | 2001 Mar 1 |
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A rat mammary tumor model induced by the organophosphorous pesticides parathion and malathion, possibly through acetylcholinesterase inhibition. | 2001 May |
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Subchronic administration of various pretreatments of nerve agent poisoning. I. Protection of blood and central cholinesterases, innocuousness towards blood-brain barrier permeability. | 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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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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Involvement of cholinergic and glutamatergic functions in working memory impairment induced by interleukin-1beta in rats. | 2001 Nov 2 |
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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 esterase-like activity of serum albumin may be due to cholinesterase contamination. | 2001 Oct |
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Synthesis, hydrolysis kinetics and anti-platelet effects of isosorbide mononitrate derivatives of aspirin. | 2001 Oct |
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Memory improving actions of gabapentin in mice: possible involvement of central muscarinic cholinergic mechanism. | 2001 Oct 5 |
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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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Doxepin-induced torsade de pointes tachycardia. | 2001 Sep 4 |
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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 |
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Physostigmine does not antagonize sevoflurane anesthesia assessed by bispectral index or enhances recovery. | 2002 Mar |
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.
Substance Class |
Chemical
Created
by
admin
on
Edited
Wed Jul 05 22:48:11 UTC 2023
by
admin
on
Wed Jul 05 22:48:11 UTC 2023
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Record UNII |
2046ZRO9VU
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Record Status |
Validated (UNII)
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Record Version |
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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
Created by
admin on Wed Jul 05 22:48:11 UTC 2023 , Edited by admin on Wed Jul 05 22:48:11 UTC 2023
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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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PARENT -> SALT/SOLVATE | |||
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PARENT -> SALT/SOLVATE |
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ACTIVE MOIETY |