Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C15H18O3 |
| Molecular Weight | 246.3016 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 4 / 4 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
C[C@H]1[C@@H]2CC[C@@]3(C)C=CC(=O)C(C)=C3[C@H]2OC1=O
InChI
InChIKey=XJHDMGJURBVLLE-BOCCBSBMSA-N
InChI=1S/C15H18O3/c1-8-10-4-6-15(3)7-5-11(16)9(2)12(15)13(10)18-14(8)17/h5,7-8,10,13H,4,6H2,1-3H3/t8-,10-,13-,15-/m0/s1
DescriptionCurator's Comment: Description was created using several sources including:
https://www.ncbi.nlm.nih.gov/pubmed/23542210;
http://naldc.nal.usda.gov/naldc/download.xhtml?id=IND43967431&content=PDF; http://www.revolvy.com/main/index.php?s=Santonin&item_type=topic; https://www.ncbi.nlm.nih.gov/pubmed/23896737
Curator's Comment: Description was created using several sources including:
https://www.ncbi.nlm.nih.gov/pubmed/23542210;
http://naldc.nal.usda.gov/naldc/download.xhtml?id=IND43967431&content=PDF; http://www.revolvy.com/main/index.php?s=Santonin&item_type=topic; https://www.ncbi.nlm.nih.gov/pubmed/23896737
Santonin, a natural compound, is a sesquiterpene lactone. It is known as an anthelmintic drug which was used in the past (19th - early 20th centuries) mainly to treat different kinds of intestinal worms such as roundworm or ascaris lumbricoides except the tapeworm. It was also indicated for use in retention of urine and nocturnal enuresis from atony, urethral irritation with pain at uterine disorders, retention of urine in fevers, deficient spinal innervation, as evidenced by impaired respiration and tympanitis, vesical tenesmus and strangury, retention of urine from the use of opiates. Santonin was formerly listed in U.S. and British pharmacopoeia but due to the severe side effects and the development of many safer deworming drugsa it is no longer registered as a drug in most countries. Originally isolated from the poisons plant Artemisia maritima, santonin is itself a toxic compound. It is the anhydride of santonic acid, which is a derivative of dimethyl-naphtalene. It dissolves in alkalies with formation of salts of this acid. In acetic acid solution, when exposed to sunlight for about a month, santonin is converted into photosantonic acid. Santonin was found to have significant anti-inflammatory activity on acute inflammatory processes and as shown in vitro can activate pregnane X receptors and constitutive androstane receptors and subsequently increases the expression of drug-metabolizing enzymes.
Approval Year
Overview
| CYP3A4 | CYP2C9 | CYP2D6 | hERG |
|---|---|---|---|
OverviewOther
| Other Inhibitor | Other Substrate | Other Inducer |
|---|---|---|
Drug as perpetrator
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
| no | ||||
| yes | ||||
Sources: https://pubmed.ncbi.nlm.nih.gov/23896737/ |
yes | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/23896737/ |
yes |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Screening of a chemical library reveals novel PXR-activating pharmacologic compounds. | 2015-01-05 |
|
| In vitro anti-plasmodial activity of Dicoma anomala subsp. gerrardii (Asteraceae): identification of its main active constituent, structure-activity relationship studies and gene expression profiling. | 2011-10-11 |
|
| Synthesis of novel α-santonin derivatives as potential cytotoxic agents. | 2010-12 |
|
| A biomimetic total synthesis of (+)-ainsliadimer A. | 2010-10-01 |
|
| Synthesis and cytotoxic activity of alpha-santonin derivatives. | 2009-09 |
|
| Synthesis of DAAS derivatives and their enhancement of HL-60 leukemia cell differentiation. | 2008-03 |
|
| Periplasmically located α-santonin binding factor in Sphingomonas paucimobilis strain S ATCC 43388. | 2007-12 |
|
| Natural products in parallel chemistry--novel 5-lipoxygenase inhibitors from BIOS-based libraries starting from alpha-santonin. | 2007-09-14 |
|
| The photoarrangement of alpha-santonin is a single-crystal-to-single-crystal reaction: a long kept secret in solid-state organic chemistry revealed. | 2007-08-15 |
|
| Seven-membered cyclic sulfite eudesmane derivatives: partial synthesis, structural determination, and enzymatic resolution. | 2007-01-19 |
|
| Biotransformation of alpha- and 6beta-santonin by fungus and plant cell cultures. | 2006-06 |
|
| Biotransformation of alpha-santonin by cell suspension cultures of five plants. | 2005-06 |
|
| Microbial transformations of alpha-santonin. | 2004-07-10 |
|
| Synthesis of phytuberin. 4-endo-tet acid-catalyzed cyclization of alpha-hydroxy epoxides. | 2003-05-30 |
|
| Antimycobacterial plant terpenoids. | 2001-11 |
Sample Use Guides
In Vivo Use Guide
Curator's Comment: The Journal of American Medical association, January 7, 1911, Volume 56, Issue 1, p.814-815
For treatment of ascaris lumbricoides in children of 5 years old 0.03 g (1/2 grain) well combined with calamel. This dose can be repeated ones an hour for three times, and then not repeated for at least 3 days
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/23896737
The effect of santonin on pregnane X receptors (PXR) activation was studied in monkey kidney-derived fibroblast (CV-1 cells) transfected with the human PXR (hPXR) and rat PXR (rPXR) expression vectors. The activity of PXR after drug treatment was determined using a PXR-responsive tk-CYP3A23-Luc reporter. Santonin at the dose of 10 μM activated both hPXR and rPXR compared to that of the vehicle controls.
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C250
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1311390
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221071
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DTXSID7045312
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santonin
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SANTONIN
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ACTIVE MOIETY