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 salicylate in the treatment of tricyclic antidepressant overdosage. | 1975 Mar 3 |
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Donepezil hydrochloride: a treatment drug for Alzheimer's disease. | 2001 |
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Clinical and institutional aspects of antidote therapy in Russia. | 2001 |
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Action of tacrine on muscarinic receptors in rat intestinal smooth muscle. | 2001 Apr |
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[Anticholinergic syndrome after postoperative dimenhydrinate administration]. | 2001 Dec |
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Stimulation of minor salivary glands by intraoral treatment with the cholinesterase inhibitor physostigmine in man. | 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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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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Septal GABAergic and hippocampal cholinergic systems modulate anxiety in the plus-maze and shock-probe tests. | 2001 Jul-Aug |
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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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[Sensory reactions of hippocampal neurons in rabbit during functional suppression of theta rythm- controlling structures]. | 2001 Mar-Apr |
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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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Concurrent quantification of tremor and depression of locomotor activity induced in rats by harmaline and physostigmine. | 2001 Nov |
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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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Methyl analogues of the experimental Alzheimer drug phenserine: synthesis and structure/activity relationships for acetyl- and butyrylcholinesterase inhibitory action. | 2001 Nov 22 |
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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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Long-term changes in hippocampus and neocortex EEG spectra in response to pharmacological treatments affecting the cholinergic system. | 2001 Nov-Dec |
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The esterase-like activity of serum albumin may be due to cholinesterase contamination. | 2001 Oct |
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Opioid receptor regulation of muscarinic acetylcholine receptor-mediated synaptic responses in the hippocampus. | 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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Muscarinic versus nicotinic modulation of a visual task. a pet study using drug probes. | 2001 Oct |
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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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Physostigmine as treatment for severe CNS anticholinergic toxicity. | 2001 Sep |
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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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The use of carbamates, atropine, and 2-pyridine aldoxime methoiodide in the protection of Artemia salina against poisoning by carbophenothion. | 2001 Sep |
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Release of non-neuronal acetylcholine from the human placenta: difference to neuronal acetylcholine. | 2001 Sep |
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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 |
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Doxepin-induced torsade de pointes tachycardia. | 2001 Sep 4 |
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Reduction of cortical amyloid beta levels in guinea pig brain after systemic administration of physostigmine. | 2001 Sep 7 |
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Selective activity of butyrylcholinesterase in serum by a chemiluminescent assay. | 2001 Sep-Oct |
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Eptastigmine: ten years of pharmacology, toxicology, pharmacokinetic, and clinical studies. | 2001 Winter |
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Donepezil for Alzheimer's disease: pharmacodynamic, pharmacokinetic, and clinical profiles. | 2001 Winter |
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Efficient formal total synthesis of physostigmine and physovenine: conformational analysis of key intermediates. | 2002 Feb |
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Mechanism of vascular relaxation by cholinomimetic drugs with special reference to pilocarpine and arecoline. | 2002 Feb |
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Physostigmine, sodium bicarbonate, or hypertonic saline to treat diphenhydramine toxicity. | 2002 Feb |
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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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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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Pharmacological properties of nicotinic acetylcholine receptors in isolated Locusta migratoria neurones. | 2002 Feb 15 |
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Presynaptic modulation of cholinergic neurotransmission in the human proximal stomach. | 2002 Jan |
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A novel class of peptides with facilitating action on neuronal nicotinic receptors of rat chromaffin cells in vitro: functional and molecular dynamics studies. | 2002 Jan |
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In vitro effects of organophosphorus anticholinesterases on muscarinic receptor-mediated inhibition of acetylcholine release in rat striatum. | 2002 Jan 15 |
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Alternative splicing and neuritic mRNA translocation under long-term neuronal hypersensitivity. | 2002 Jan 18 |
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Central anticholinergics to treat nerve-agent poisoning. | 2002 Jan 19 |
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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.
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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