Details
Stereochemistry | RACEMIC |
Molecular Formula | C17H23NO4.ClH |
Molecular Weight | 341.83 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 5 / 5 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.CN1[C@@H]2C[C@H](O)[C@H]1C[C@H](C2)OC(=O)[C@H](CO)C3=CC=CC=C3
InChI
InChIKey=TXJYFXBXRUTHSF-YXGOVGSCSA-N
InChI=1S/C17H23NO4.ClH/c1-18-12-7-13(9-15(18)16(20)8-12)22-17(21)14(10-19)11-5-3-2-4-6-11;/h2-6,12-16,19-20H,7-10H2,1H3;1H/t12-,13-,14+,15+,16-;/m0./s1
Molecular Formula | ClH |
Molecular Weight | 36.461 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Molecular Formula | C17H23NO4 |
Molecular Weight | 305.3688 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 5 / 5 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/17186568Curator's Comment: Description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/27010563
Sources: https://www.ncbi.nlm.nih.gov/pubmed/17186568
Curator's Comment: Description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/27010563
Anisodamine is a naturally occurring atropine derivative that has been isolated, synthesized and characterized by scientists in the People's Republic of China. Anisodamine is a non-specific cholinergic antagonist. Anisodamine has been shown to interact with and disrupt liposome structure which may reflect its effects on cellular membranes. Experimental evidence implicates anisodamine as an anti-oxidant that may protect against free radical-induced cellular damage. Its cardiovascular properties include depression of cardiac conduction and the ability to protect against arrhythmia induced by various agents. Anisodamine is a relatively weak alpha(1) adrenergic antagonist which may explain its vasodilating activity. Its anti-thrombotic activity may be a result of inhibition of thromboxane synthesis. Numerous therapeutic uses of anisodamine have been proposed including treatment of septic shock, various circulatory disorders, organophosphorus (OP) poisoning, migraine, gastric ulcers, gastrointestinal colic, acute glomerular nephritis, eclampsia, respiratory diseases, rheumatoid arthritis, obstructive jaundice, opiate addiction, snake bite and radiation damage protection. The primary therapeutic use of anisodamine has been for the treatment of septic shock. Several mechanisms have been proposed to explain its beneficial effect though most mechanisms are based upon the assumption that anisodamine ultimately acts by an improvement of blood flow in the microcirculation. Preliminary studies suggest another important therapeutic use of anisodamine is for the treatment of OP poisoning. Anisodamine has been employed
therapeutically since 1965 in the People’s Republic of China primarily to improve blood flow in circulatory disorders such as septic shock, disseminated intravascular coagulation (DIC) and as an antidote to organophosphate poisoning.
CNS Activity
Sources: https://www.ncbi.nlm.nih.gov/pubmed/19756370 | https://www.ncbi.nlm.nih.gov/pubmed/17186568
Curator's Comment: Anisodamine hardly influenced cognition at normal doses due to its extremely low blood–brain barrier permeability. Anisodamine counteracts cholinergic adverse effects and facilitates cognitive amelioration of rivastigmine. Anisodamine displays less CNS toxicity than scopolamine.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL1825 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11395932 |
|||
Target ID: CHEMBL3365 |
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Target ID: CHEMBL2094251 |
5.06 null [pKi] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
---|---|---|
A combination of neostigmine and anisodamine protects against ischemic stroke by activating α7nAChR. | 2015 Jul |
|
Establishment, Culture, and Scale-up of Brugmansia candida Hairy Roots for the Production of Tropane Alkaloids. | 2016 |
|
Possible role for anisodamine in organophosphate poisoning. | 2016 Jun |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://clinicaltrials.gov/ct2/show/NCT02442440
Anisodamine will be given first as bolus of 10 mg, followed by 0.1-0.5mg/kg/hr.
Route of Administration:
Parenteral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/11395932
Anisodamine at 50 ug/ml suppressed TNF-a production in human monocytic cells after 24 hr. Anisodamine at concentration 400 ug/ml inhibited Stx2-induced TNF-a production completely.
Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 19:23:47 GMT 2023
by
admin
on
Sat Dec 16 19:23:47 GMT 2023
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Record UNII |
QHN9HU8V5M
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Record Status |
Validated (UNII)
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Record Version |
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51051790
Created by
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QHN9HU8V5M
Created by
admin on Sat Dec 16 19:23:47 GMT 2023 , Edited by admin on Sat Dec 16 19:23:47 GMT 2023
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PARENT -> SALT/SOLVATE |
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