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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
Structure of SANTONIN

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

HIDE SMILES / InChI

Description

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.

CNS Activity

Originator

Approval Year

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Santonin U.S.P.

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer

Drug as perpetrator​

PubMed

Sample Use Guides

In Vivo Use Guide
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
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.