Trioxsalen

Summary

Trioxsalen (CHEMBL1475) is an approved small-molecule photosensitizing agent (ATC D05AD01); indicated across 1 condition including psoriasis.

At a glance

• Status: Approved (max clinical phase 4)
• Modality: Small molecule
• ATC class: D05AD01 (+1 more)
• Indications: 1 condition
• Chemistry: 228.24 Da · C14H12O3

Identifiers

Drug identity and classification

Field	Value
ChEMBL ID	CHEMBL1475
Name	Trioxsalen
Type	Small molecule
Max phase	4
FDA approved	no
PubChem CID	5585
ChEBI	CHEBI:28329
ATC	D05AD01, D05BA01
Molecular formula	C14H12O3
Molecular weight	228.24
InChIKey	FMHHVULEAZTJMA-UHFFFAOYSA-N

SMILES: CC1=CC(=O)OC2=C1C=C3C=C(OC3=C2C)C

IUPAC name: 2,5,9-trimethylfuro[3,2-g]chromen-7-one

ChEBI definition: 7H-Furo[3,2-g]chromen-7-one in which positions 2, 5, and 9 are substituted by methyl groups. Like other psoralens, trioxsalen causes photosensitization of the skin. It is administered orally in conjunction with UV-A for phototherapy treatment of vitiligo. After photoactivation it creates interstrand cross-links in DNA, inhibiting DNA synthesis and cell division, and can lead to cell injury; recovery from the cell injury may be followed by increased melanisation of the epidermis.

Pharmacological roles (ChEBI): photosensitizing agent, dermatologic drug.

Also known as: NSC-71047, Tmp (psoralen), Trioxisaleno, Trioxsalen, Trioxysalen, Trioxysalene, Trisoralen, SID11112550, SID26748294, TRIOXSALEN, SID49647255, SID114185

Patent coverage: 93,636 distinct patent families (219,770 SureChEMBL compound mentions), from 2 matched compound structure(s). One matched structure accounts for 219,715 (100%) of the total. Mentions count patents naming the compound (not distinct inventions), so promiscuous / reference molecules inflate the mention figure — families are the dedup metric.

Targets

Targets

Broader ChEMBL bioactivity targets: 8 (assay-derived). Sample: Lysine-specific demethylase 4E, Amine oxidase [flavin-containing] A, 5-hydroxytryptamine receptor 2C, Adenosine receptor A2a, Cytochrome P450 1A2, Cytochrome P450 3A4, Aldehyde dehydrogenase 1A1, Mitogen-activated protein kinase 1.

Bioactivity

ChEMBL activities: 17 potent at pChembl ≥ 5 of 17 total. Top 100 by potency (10 = 0.1 nM, 6 = 1 µM):

Target	pChembl	Type	Value	Unit	Activity ID
KDM4E	6.55	Potency	281.8	nM	CHEMBL_ACT_3747072
MAOA	6.14	AC50	720	nM	CHEMBL_ACT_25159765
ADORA2A	6.13	Ki	737	nM	CHEMBL_ACT_7787039
MAOA	6.08	IC50	831	nM	CHEMBL_ACT_7787984
CYP1A2	6	AC50	1000	nM	CHEMBL_ACT_6003069
HTR2C	5.91	Ki	1234	nM	CHEMBL_ACT_7788882
ADORA2A	5.88	IC50	1312	nM	CHEMBL_ACT_7787038
HTR2C	5.63	IC50	2356	nM	CHEMBL_ACT_7788881
ALDH1A1	5.45	Potency	3548	nM	CHEMBL_ACT_4169295
CYP3A4	5.4	Potency	3981	nM	CHEMBL_ACT_5002122
CYP3A4	5.4	Potency	3981	nM	CHEMBL_ACT_5070736
CYP3A4	5.4	AC50	3981	nM	CHEMBL_ACT_6070219
KDM4E	5.25	Potency	5623	nM	CHEMBL_ACT_3740849
MAPK1	5.2	Potency	6310	nM	CHEMBL_ACT_4533856
ADORA2A	5.17	AC50	6700	nM	CHEMBL_ACT_25152566
CYP3A4	5.1	Potency	7943	nM	CHEMBL_ACT_4993966
CYP3A4	5.1	Potency	7943	nM	CHEMBL_ACT_5062837

Target pathways

No target-pathway data for this drug (no mapped target genes).

Indications & clinical

Indications

1 approved indication. FDA phase 4, plus an anticancer drug’s labelled cancer uses (which ChEMBL often logs at phase 3).

Indication	Phase	MONDO	EFO
psoriasis	4	MONDO:0005083	EFO:0000676

Clinical trials

Total trials: 0.

Clinical evidence (CIViC)

No CIViC predictive evidence (expected for non-precision-medicine drugs).

Pharmacology

Pharmacogenomics

No PharmGKB pharmacogenomic data curated for this drug.

Related molecules

Related molecules

No competitor molecules sharing a primary target (ChEMBL phase ≥2 or PubChem drug-class).