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=CC=CC=C1O.CNC(=O)OC2=CC=C3N(C)[C@H]4N(C)CC[C@@]4(C)C3=C2
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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Donepezil hydrochloride: a treatment drug for Alzheimer's disease. | 2001 |
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Involvement of cholinergic mechanisms in the central control of respiration in the cane toad, Bufo marinus. | 2001 Apr |
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[Anticholinergic syndrome after postoperative dimenhydrinate administration]. | 2001 Dec |
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Quantitative measurement of cerebral acetylcholinesterase using. | 2001 Feb |
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Physostigmine versus diazepines for anticholinergic poisoning. | 2001 Feb |
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Dehydroevodiamine attenuates beta-amyloid peptide-induced amnesia in mice. | 2001 Feb 16 |
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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 |
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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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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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Reversal of morphine-induced memory impairment in mice by withdrawal in Morris water maze: possible involvement of cholinergic system. | 2001 Mar |
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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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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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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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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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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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Pharmacological properties of nicotinic acetylcholine receptors in isolated Locusta migratoria neurones. | 2002 Feb 15 |
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Alternative splicing and neuritic mRNA translocation under long-term neuronal hypersensitivity. | 2002 Jan 18 |
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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
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admin
on
Edited
Mon Mar 31 17:52:47 GMT 2025
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on
Mon Mar 31 17:52:47 GMT 2025
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Record UNII |
2046ZRO9VU
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Record Status |
Validated (UNII)
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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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PARENT -> SALT/SOLVATE | |||
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PARENT -> SALT/SOLVATE |
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ACTIVE MOIETY |