532:
509:
869:(DMAPP), produced via the mevalonate pathway, to form a carbo-cation via the cleavage of the diphosphates. Once activated, the enzyme umbelliferone 6-prenyltransferase catalyzes a C-alkylation between DMAPP and umbelliferone at the activated position ortho to the phenol, yielding demethylsuberosin. This is then followed by a hydroxylation catalyzed by the enzyme marmesin synthase to yield
802:
40:
1888:
856:
699:(UVA) light from lamps or sunlight. Methoxsalen modifies the way skin cells receive the UVA radiation, allegedly clearing up the disease. Levels of individual patient PUVA exposure were originally determined using the
1235:
214:
159:
1239:
70:
609:
1132:
Marshall SR (June 2006). "Technology insight: ECP for the treatment of GvHD--can we offer selective immune control without generalized immunosuppression?".
1943:
905:
problems are at risk for inflammation and irreparable damage to both liver and skin. The eyes must be protected from UVA radiation. Side effects include
1290:
1402:
707:
after oral ingestion of methoxsalen followed by PUVA therapy. Chemically, methoxsalen belongs to a class of organic natural molecules known as
1496:
1204:
1552:
940:(1920–1980) used the chemical to darken his skin in order to investigate racial segregation in the American South. He wrote the book
1923:
881:. A third hydroxylation by the enzyme psoralen 8-monooxygenase yields xanthotoxol which is followed by a methylation via the enzyme
629:
843:
group. Finally an intramolecular attack from the hydroxyl group of C2' to the carboxylic acid group closes the ring and forms the
1918:
971:
1105:
Fahmy IR, Abu-Shady H (1947). "Ammi majus Linn.; pharmacognostical study and isolation of a crystalline constituent, ammoidin".
1079:
1053:
1933:
882:
269:
199:
88:
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1283:
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388:
835:. The 4-coumaric acid is again hydroxylated by cinnamate/coumarate 2-hydroxylase to yield 2,4-dihydroxy-cinnamic acid (
107:
1661:
1513:
866:
859:
488:
1913:
1908:
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1928:
751:
1501:
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925:
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1025:"FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)"
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928:(known to cause cancer) but is only cancerous when combined with light - UVA radiation.
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1902:
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819:, which in turn is produced via the shikimate pathway. Phenylalanine is lysated into
805:
786:
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227:
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730:
In 1947, methoxsalen was isolated (under the name "ammoidin") from the plant
80:
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1729:
1693:
1633:
1609:
1478:
1455:
1392:
1347:
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739:
In 1970, Nielsen extracted 8-methoxypsoralen from four species of the genus
680:
74:
31:
1157:
1118:
801:
17:
637:
InChI=1S/C12H8O4/c1-14-12-10-8(4-5-15-10)6-7-2-3-9(13)16-11(7)12/h2-6H,1H3
1865:
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Botanical
Dermatology: Plants and Plant Products Injurious to the Skin
839:) followed by a bond rotation of the unsaturated bond adjacent to the
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703:. The scale was developed after patients demonstrated symptoms of
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1534:
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1032:
1224:(3rd ed.). John Wiley & Sons. pp. 161, 164–165.
865:
The biosynthetic route then continues with the activation of
493:
208:
129:
654:
1876:
1080:"Oxsoralen-Ultra- methoxsalen capsule, liquid filled"
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Medicinal
Natural Products: A Biosynthetic Approach
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781:The biosynthetic pathway is a combination of the
336:
311:
1183:. Copenhagen: Royal Danish School of Pharmacy.
1107:Quarterly Journal of Pharmacy and Pharmacology
722:. It can also be injected and used topically.
1546:
1284:
761:. An additional 32 species of the genus
8:
476:
106:
30:
1199:. Vancouver: Greengrass. pp. 692–699.
924:Methoxsalen has also been classified as an
1719:
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1238:. American Cancer Society. Archived from
1054:"Uvadex- methoxsalen injection, solution"
765:were found to contain 5-methoxypsoralen (
695:in conjunction with exposing the skin to
396:
873:. Another hydroxylation is catalyzed by
1883:
955:
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274:
1236:"Known and Probable Human Carcinogens"
1003:Therapeutic Goods Administration (TGA)
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1086:. U.S. National Library of Medicine
1060:. U.S. National Library of Medicine
416:
327:
1944:General cytochrome P450 inhibitors
1185:Cited by Mitchell and Rook (1979).
1134:Nature Clinical Practice. Oncology
25:
1181:Coumarins of Umbelliferous plants
1886:
1774:Meroterpene furanocoumarin ether
1662:Umbelliferone 7-apiosylglucoside
972:Therapeutic Goods Administration
815:and as such is synthesized from
555:
57:Oxsoralen, Uvadex, 8-mop, others
883:xanthotoxol O-methyltransferase
642:Key:QXKHYNVANLEOEG-UHFFFAOYSA-N
1255:"Death of John Howard Griffin"
946:(1961) about his experiences.
561:
549:
1:
1113:(3): 281–91, discussion 426.
1253:Mikkelson D (27 July 2003).
671:) sold under the brand name
1195:Mitchell J, Rook A (1979).
867:dimethylallyl pyrophosphate
860:Dimethylallyl pyrophosphate
617:COc1c2c(ccc(=O)o2)cc3c1occ3
1970:
1403:Calcipotriol/betamethasone
797:Synthesis of umbelliferone
539:Chemical and physical data
1758:Furanocoumarin glycosides
1491:
1261:. Snopes Media Group Inc.
650:
625:
605:
265:
81:Consumer Drug Information
37:
1924:IARC Group 1 carcinogens
1300:Drugs used for psoriasis
851:Synthesis of methoxsalen
785:pathway, which produces
752:Heracleum mantegazzianum
1919:Photosensitizing agents
926:IARC Group 1 carcinogen
829:cinnamate 4-hydroxylase
1934:O-methylated coumarins
893:Risks and side effects
889:to yield methoxsalen.
862:
808:
1242:on 30 September 2016.
999:"AusPAR: Methoxsalen"
887:S-adenosyl methionine
858:
804:
758:Heracleum sphondylium
745:in the carrot family
291:-furobenzopyran-7-one
1846:Ethyl biscoumacetate
917:, and in rare cases
1179:Nielsen BE (1970).
938:John Howard Griffin
932:Society and culture
899:high blood pressure
811:Umbelliferone is a
693:cutaneous lymphomas
675:among others, is a
217:(Prescription only)
34:
1851:4-Hydroxycoumarins
1518:Never to phase III
1220:Dewick PM (2009).
1150:10.1038/ncponc0511
1005:. 12 December 2019
976:. 13 December 2019
863:
809:
791:mevalonate pathway
711:. They consist of
284:-furochromen-7-one
1914:CYP3A4 inhibitors
1909:CYP1A2 inhibitors
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1206:978-0-88978-047-7
1142:Nature Publishing
875:psoralen synthase
736:, bishop's weed.
701:Fitzpatrick scale
662:
661:
596:Interactive image
489:CompTox Dashboard
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27:Chemical compound
16:(Redirected from
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901:or a history of
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1939:Catechol ethers
1929:Furanocoumarins
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1679:Furanocoumarins
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1508:Clinical trials
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847:umbelliferone.
841:carboxylic acid
833:4-coumaric acid
817:L-phenylalanine
813:phenylpropanoid
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771:furanocoumarins
728:
726:Natural sources
709:furanocoumarins
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1735:Isopimpinellin
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897:Patients with
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1861:Phenprocoumon
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1837:
1836:Coumatetralyl
1834:
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1831:Acenocoumarol
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1589:Umbelliferone
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943:Black Like Me
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837:umbellic acid
834:
830:
826:
825:hydroxylation
822:
821:cinnamic acid
818:
814:
807:
806:Umbelliferone
803:
796:
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788:
787:umbelliferone
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1954:Plant toxins
1949:Orphan drugs
1739:
1723:O-Methylated
1598:O-Methylated
1450:
1398:Calcipotriol
1391:
1387:Fumaric acid
1370:
1258:
1248:
1240:the original
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1090:17 September
1088:. Retrieved
1083:
1074:
1064:17 September
1062:. Retrieved
1057:
1048:
1036:. Retrieved
1028:
1019:
1009:17 September
1007:. Retrieved
1002:
978:. Retrieved
970:
941:
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777:Biosynthesis
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749:, including
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672:
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664:
663:
652:
469:NIAID ChemDB
288:
281:
249:Elimination
200:Legal status
194:Legal status
89:License data
1856:Hymecromone
1791:Imperatorin
1786:Bergamottin
1740:Methoxsalen
1714:Xanthotoxol
1671:Derivatives
1504:from market
1451:Methoxsalen
1446:Trioxysalen
1371:Methoxsalen
1366:Trioxysalen
1144:: 302–314.
769:) or other
697:ultraviolet
691:, and some
669:xanthotoxin
665:Methoxsalen
579: g·mol
528:100.005.516
438:CHEBI:18358
287:9-methoxy-7
280:9-methoxy-7
261:Identifiers
108:Methoxsalen
65:xanthotoxin
62:Other names
53:Trade names
32:Methoxsalen
18:Xanthotoxin
1903:Categories
1815:Dicoumarol
1745:Trioxsalen
1634:Glycosides
1620:Scopoletin
1579:Aesculetin
1474:Etretinate
1419:Tazarotene
1413:Tacalcitol
1408:Calcitriol
1259:snopes.com
950:References
789:, and the
733:Ammi majus
677:medication
584:3D model (
572:Molar mass
398:U4VJ29L7BQ
369:ChemSpider
304:CAS Number
270:IUPAC name
1841:Ensaculin
1824:Synthetic
1808:Oligomers
1781:Auraptene
1730:Bergapten
1694:Angelicin
1687:Aglycones
1610:Herniarin
1571:Aglycones
1563:coumarins
1561:Types of
1514:Phase III
1502:Withdrawn
1479:Acitretin
1466:Retinoids
1456:Bergapten
1439:Psoralens
1393:vitamin D
1358:Psoralens
1348:Dithranol
1340:Antracens
980:25 August
915:dizziness
911:headaches
877:to yield
831:to yield
783:shikimate
767:bergapten
763:Heracleum
742:Heracleum
716:annulated
681:psoriasis
673:Oxsoralen
458:ChEMBL416
251:half-life
145:Routes of
119:Pregnancy
75:Drugs.com
1893:Medicine
1866:Warfarin
1704:Psoralen
1699:Marmesin
1657:Scopolin
1642:Aesculin
1605:Fraxetin
1432:Systemic
1330:Coal tar
1158:16757968
1119:20273299
1084:DailyMed
1058:DailyMed
967:"Uvadex"
919:insomnia
879:psoralen
871:marmesin
747:Apiaceae
713:coumarin
689:vitiligo
655:(verify)
349:DrugBank
313:298-81-7
256:~2 hours
160:ATC code
153:By mouth
121:category
103:DailyMed
1765:Apterin
1709:Vaginol
1652:Skimmin
1584:Ferujol
1312:Topical
1166:8441159
936:Author
845:lactone
577:216.192
545:Formula
358:DB00553
324:PubChem
232:Rx-only
229:WARNING
180: (
178:D05BA02
176:)
170: (
168:D05AD02
134: D
105::
1879:Portal
1647:Fraxin
1615:Osthol
1497:WHO-EM
1203:
1164:
1156:
1117:
1038:22 Oct
907:nausea
685:eczema
610:SMILES
478:001590
449:ChEMBL
418:D00139
226:
213:
101:
1380:Other
1162:S2CID
1140:(6).
974:(TGA)
903:liver
720:furan
718:with
630:InChI
586:JSmol
429:ChEBI
1319:Tars
1201:ISBN
1154:PMID
1115:PMID
1092:2021
1066:2021
1040:2023
1011:2021
982:2020
885:and
755:and
667:(or
409:KEGG
389:UNII
378:3971
338:4114
243:data
71:AHFS
1326:Tar
1304:D05
1146:doi
1033:FDA
827:by
494:EPA
328:CID
183:WHO
173:WHO
1905::
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687:,
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553:12
222:US
215:S4
209:AU
130:AU
98:US
1881::
1554:e
1547:t
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1396:(
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562:O
559:8
556:H
550:C
496:)
492:(
289:H
282:H
224::
211::
186:)
132::
73:/
20:)
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