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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

[H][C@@]12CC[C@@]3(C)C=CC(=O)C(C)=C3[C@@]1([H])OC(=O)[C@H]2C

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

Molecular Formula C15H18O3
Molecular Weight 246.3016
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 4 / 4
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
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.

Originator

Curator's Comment: Santonin was discovered, in 1830

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Santonin U.S.P.

Approved Use

To remove ascaris lumbricoides or round worm of intestine
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer

Drug as perpetrator​
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Antimycobacterial plant terpenoids.
2001 Nov
Synthesis of phytuberin. 4-endo-tet acid-catalyzed cyclization of alpha-hydroxy epoxides.
2003 May 30
Microbial transformations of alpha-santonin.
2004 Mar-Apr
Biotransformation of alpha-santonin by cell suspension cultures of five plants.
2005 Jun
Biotransformation of alpha- and 6beta-santonin by fungus and plant cell cultures.
2006 Jun
The photoarrangement of alpha-santonin is a single-crystal-to-single-crystal reaction: a long kept secret in solid-state organic chemistry revealed.
2007 Aug 15
Periplasmically located α-santonin binding factor in Sphingomonas paucimobilis strain S ATCC 43388.
2007 Dec
Seven-membered cyclic sulfite eudesmane derivatives: partial synthesis, structural determination, and enzymatic resolution.
2007 Jan 19
Natural products in parallel chemistry--novel 5-lipoxygenase inhibitors from BIOS-based libraries starting from alpha-santonin.
2007 Nov-Dec
Synthesis of DAAS derivatives and their enhancement of HL-60 leukemia cell differentiation.
2008 Mar
Synthesis and cytotoxic activity of alpha-santonin derivatives.
2009 Sep
Synthesis of novel α-santonin derivatives as potential cytotoxic agents.
2010 Dec
A biomimetic total synthesis of (+)-ainsliadimer A.
2010 Oct 1
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 Oct 11
Screening of a chemical library reveals novel PXR-activating pharmacologic compounds.
2015 Jan 5
Patents

Sample Use Guides

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
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.
Substance Class Chemical
Created
by admin
on Fri Dec 15 17:12:25 UTC 2023
Edited
by admin
on Fri Dec 15 17:12:25 UTC 2023
Record UNII
1VL8J38ERO
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
SANTONIN
MART.   WHO-DD  
Common Name English
SANTONINUM [HPUS]
Common Name English
SANTONIN [MART.]
Common Name English
Santonin [WHO-DD]
Common Name English
.ALPHA.-SANTONIN [MI]
Common Name English
SANTONINUM
HPUS  
Common Name English
SANTONIN [JAN]
Common Name English
NSC-4900
Code English
(3S,3AS,5AS)-3,5A,9-TRIMETHYL-3A,4,5,5A-TETRAHYDRONAPHTHO(1,2-B)FURAN-2,8(3H,9BH)-DIONE
Common Name English
(3S,3AS,5AS,9BS)-3A,5,5A,9B-TETRAHYDRO-3,5A,9-TRIMETHYLNAPHTHO(1,2-B)FURAN-2,8(3H,4H)-DIONE
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C250
Created by admin on Fri Dec 15 17:12:25 UTC 2023 , Edited by admin on Fri Dec 15 17:12:25 UTC 2023
Code System Code Type Description
SMS_ID
100000078395
Created by admin on Fri Dec 15 17:12:25 UTC 2023 , Edited by admin on Fri Dec 15 17:12:25 UTC 2023
PRIMARY
FDA UNII
1VL8J38ERO
Created by admin on Fri Dec 15 17:12:25 UTC 2023 , Edited by admin on Fri Dec 15 17:12:25 UTC 2023
PRIMARY
MESH
D012500
Created by admin on Fri Dec 15 17:12:25 UTC 2023 , Edited by admin on Fri Dec 15 17:12:25 UTC 2023
PRIMARY
MERCK INDEX
m9768
Created by admin on Fri Dec 15 17:12:25 UTC 2023 , Edited by admin on Fri Dec 15 17:12:25 UTC 2023
PRIMARY Merck Index
RXCUI
1311390
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PRIMARY RxNorm
PUBCHEM
221071
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PRIMARY
EVMPD
SUB15192MIG
Created by admin on Fri Dec 15 17:12:25 UTC 2023 , Edited by admin on Fri Dec 15 17:12:25 UTC 2023
PRIMARY
CAS
481-06-1
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PRIMARY
CHEBI
26604
Created by admin on Fri Dec 15 17:12:25 UTC 2023 , Edited by admin on Fri Dec 15 17:12:25 UTC 2023
PRIMARY
NCI_THESAURUS
C87627
Created by admin on Fri Dec 15 17:12:25 UTC 2023 , Edited by admin on Fri Dec 15 17:12:25 UTC 2023
PRIMARY
NSC
4900
Created by admin on Fri Dec 15 17:12:25 UTC 2023 , Edited by admin on Fri Dec 15 17:12:25 UTC 2023
PRIMARY
ChEMBL
CHEMBL259254
Created by admin on Fri Dec 15 17:12:25 UTC 2023 , Edited by admin on Fri Dec 15 17:12:25 UTC 2023
PRIMARY
EPA CompTox
DTXSID7045312
Created by admin on Fri Dec 15 17:12:25 UTC 2023 , Edited by admin on Fri Dec 15 17:12:25 UTC 2023
PRIMARY
ALANWOOD
santonin
Created by admin on Fri Dec 15 17:12:25 UTC 2023 , Edited by admin on Fri Dec 15 17:12:25 UTC 2023
PRIMARY
ECHA (EC/EINECS)
207-560-7
Created by admin on Fri Dec 15 17:12:25 UTC 2023 , Edited by admin on Fri Dec 15 17:12:25 UTC 2023
PRIMARY
DAILYMED
1VL8J38ERO
Created by admin on Fri Dec 15 17:12:25 UTC 2023 , Edited by admin on Fri Dec 15 17:12:25 UTC 2023
PRIMARY
WIKIPEDIA
SANTONIN
Created by admin on Fri Dec 15 17:12:25 UTC 2023 , Edited by admin on Fri Dec 15 17:12:25 UTC 2023
PRIMARY
Related Record Type Details
ACTIVE MOIETY