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
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
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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On the anticataleptic action of cyproheptadine. | 1976 Aug |
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[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 |
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Donepezil hydrochloride: a treatment drug 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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Involvement of cholinergic mechanisms in the central control of respiration in the cane toad, Bufo marinus. | 2001 Apr |
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Endogenous acetylcholine facilitates epileptogenesis in immature rat neocortex. | 2001 Apr 13 |
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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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Functional relationship between subfornical organ cholinergic stimulation and cellular activation in the hypothalamus and AV3V region. | 2001 Dec 20 |
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Acute toxicity screening of novel AChE inhibitors using neuronal networks on microelectrode arrays. | 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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Sexual diergism in rat hypothalamic-pituitary-adrenal axis responses to cholinergic stimulation and antagonism. | 2001 Jan 1 |
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Viral neuroinvasion as a marker for BBB integrity following exposure to cholinesterase inhibitors. | 2001 Jan 19 |
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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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Physostigmine and cognition in schizotypal personality disorder. | 2001 Mar 1 |
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Factors that determine acetylcholine responsiveness of guinea pig tracheal tubes. | 2001 May 25 |
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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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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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The esterase-like activity of serum albumin may be due to cholinesterase contamination. | 2001 Oct |
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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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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 |
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Physostigmine as treatment for severe CNS anticholinergic toxicity. | 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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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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Efficient formal total synthesis of physostigmine and physovenine: conformational analysis of key intermediates. | 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 |
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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WHO-VATC |
QS01EB05
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S01EB05
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NCI_THESAURUS |
C47792
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WHO-VATC |
QA03FA90
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QA03AX90
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WHO-VATC |
QV03AB19
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LIVERTOX |
776
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WHO-ATC |
V03AB19
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Physostigmine
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m8766
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5983
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PHYSOSTIGMINE
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DB00981
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SUB14864MIG
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C81337
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ACTIVE MOIETY
SALT/SOLVATE (PARENT)
SALT/SOLVATE (PARENT)