Xanthotoxin

Structural formula
General
Surname	Methoxsalen
other names	9-methoxy-7 H -furo [3,2- g ] [1] benzopyran-7-one; 8-methoxypsoralen (8-MOP);
Molecular formula	C 12 H 8 O 4
Brief description	colorless needles or prisms, tastes bitter with a tingling aftertaste
External identifiers / databases
EC number	206-066-9
ECHA InfoCard	100.005.516
PubChem	4114
ChemSpider	3971
DrugBank	DB00553
Wikidata	Q408570
Drug information
ATC code	D05 AD02 ; D05 BA02 ;
Drug class	Photosensitizer
properties
Molar mass	216.18 g mol −1
Physical state	firmly
Melting point	148 ° C
solubility	soluble in acetone , boiling alcohol; sparingly soluble in hot water , ether
safety instructions
	Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS labeling of hazardous substances Caution
H and P phrases	H: 302-317
	P: 280
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Xanthotoxin is a natural substance found in the essential oils of various plants . Xanthotoxin is a substance from the group of psoralens , which in turn are counted among the coumarins .

Occurrence

Medicinal angelica ( Angelica archangelica )

Xanthotoxin occurs in the African tree Fagara xanthoxyloides and in various umbelliferae such as angelica , bergamot , parsnip and giant hogweed .

Clinical information

Application areas (indications)

The drug is used for some skin diseases (e.g. psoriasis ). At the same time, long-wave UV light can also be used. In such a case, one speaks of PUVA therapy.

hazards

Xanthotoxin is poisonous for cold blooded animals . Like the chemically related bergapten , xanthotoxin, being a linear furanocoumarin, has photosensitizing properties, i.e. it sensitizes the skin to sunlight and UV radiation. The substance causes severe inflammation and sunburn when exposed to light . Xanthotoxin also damages the DNA of the skin cells, so that long-term damage such as cancer can result.

Trade names

Monopreparations

Meladinine (D, CH), Oxsoralen (A), Uvadex (D, A, CH)

literature

Ernst Mutschler: drug effects. 7th edition 1996, WVG Stuttgart, ISBN 3-8047-1377-7

Individual evidence

↑ ^a ^b ^c ^d Entry on xanthotoxin. In: Römpp Online . Georg Thieme Verlag, accessed on March 15, 2011.
↑ ^a ^b Xanthotoxin data sheet from Sigma-Aldrich , accessed on May 13, 2017 ( PDF ).

Web links

Entries in the NIH study registry

[Römpp-1] Entry on xanthotoxin. In: Römpp Online . Georg Thieme Verlag, accessed on March 15, 2011.

[Sigma-2] Xanthotoxin data sheet from Sigma-Aldrich , accessed on May 13, 2017 ( PDF ).