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Compound Detail

CHEMBL416

METHOXSALEN
💊 Approved Drug
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💊 Approved Drug
COc1c2occc2cc2ccc(=O)oc12
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL416
Name METHOXSALEN
Phase Approved
Structure Type MOL
InChI Key QXKHYNVANLEOEG-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

8-methoxsalen 8-mop Deltasoralen Meladinine Methoxsalen METHOXSALEN COMPONENT OF SM-88 Metoxalen NSC-45923 Oxsoralen Oxsoralen-ultra Oxypsoralen Puvalen +3 more
19
Targets
63
Activities
4
Assay Types
2
PK Parameters
20
Publications
15
Known Names
14
Indications
1
Mechanisms

Molecular Properties

216.2
MW (Da)
2.55
ALogP
4
HBA
0
HBD
52.6
PSA (Ų)
0.59
QED
0
Ro5 Violations
1
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1954
Availability Prescription
Chirality Achiral

Routes of Administration

Oral Parenteral Topical

Flags

Black Box Warning Natural Product
USAN Stem -sal-

Extended Properties

Molecular Formula C12H8O4
MW 216.19
Aromatic Rings 3
Heavy Atoms 16
NP-Likeness 1.26

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
DNA inhibitor INHIBITOR DNA ✓ ✓

Indications

Lymphoma, T-Cell Psoriasis Graft vs Host Disease Graft vs Host Disease Lymphoma Mycosis Fungoides Arthritis, Rheumatoid Bronchiolitis Obliterans Syndrome Crohn Disease Epidermolysis Bullosa Acquisita Pancreatic Neoplasms Scleroderma, Diffuse Sezary Syndrome Hematologic Neoplasms

ATC Classification

D05AD02
methoxsalen
Level 1: DERMATOLOGICALS
Level 2: ANTIPSORIATICS
D05BA02
methoxsalen
Level 1: DERMATOLOGICALS
Level 2: ANTIPSORIATICS

Drug Warnings

Black Box Warning
carcinogenicity
Country: United States

Activity Summary

IC50 51 meas. best 7.4
Ki 9 meas. best 7.4
Kd 2 meas. best 5.8
EC50 1 meas. best 4.83

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Cytochrome P450 1A2
CHEMBL3356
 IC50 7.4 7.4 40.0 1
Cytochrome P450 2A13
CHEMBL3542436
 Ki 7.4 7.4 40.0 1
Cytochrome P450 2A6
CHEMBL5282
 Ki 7.05 6.295 90.0 6
PAM212
CHEMBL614231
 IC50 7.0 7.0 100.0 1
LoVo
CHEMBL614721
 IC50 6.4 6.1086 400.0 7
Cytochrome P450 2A6
CHEMBL5282
 IC50 6.34 6.34 460.0 1
HL-60
CHEMBL383
 IC50 6.12 5.601 750.0 10
Acetylcholinesterase
CHEMBL220
 IC50 6.12 5.195 760.0 2
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 6.05 5.6067 900.0 3
Jurkat
CHEMBL397
 IC50 5.92 5.92 1200.0 2
HT-1080
CHEMBL614580
 IC50 5.82 5.488 1500.0 5
Cytochrome P450 2A13
CHEMBL3542436
 Kd 5.8 5.8 1600.0 1
Cytochrome P450 3A4
CHEMBL340
 Ki 5.66 5.13 2200.0 2
A-431
CHEMBL614069
 IC50 5.61 5.105 2480.0 2
HeLa
CHEMBL399
 IC50 5.5 5.0714 3160.0 7
ADMET
CHEMBL612558
 IC50 5.26 5.26 5500.0 1
Cytochrome P450 2A6
CHEMBL5282
 Kd 4.96 4.96 11000.0 1
Tyrosinase
CHEMBL3318
 EC50 4.83 4.83 14800.0 1
Unchecked
CHEMBL612545
 IC50 4.55 4.4133 28000.0 3
PANC-1
CHEMBL614139
 IC50 4.08 4.08 83300.0 1
Amine oxidase [flavin-containing] A
CHEMBL1951
 IC50 4.07 4.07 85110.0 1
Panel leukemia (Carcinoma cell lines)
CHEMBL614083
 IC50 4.0 4.0 100000.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 6.0 mL.min-1.g-1 Homo sapiens
CL 52.0 uL.min-1.(10^6cells)-1 Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Cytochrome P450 1A2 IC50 = 40.0 nM 7.4 DRUGMATRIX: CYP450, 1A2 enzyme inhibition (substrate: 3-Cyano-7-ethoxycoumarin) -
Cytochrome P450 2A13 Ki = 40.0 nM 7.4 Mixed inhibition of CYP2A13 (unknown origin) 22696418
Cytochrome P450 2A6 Ki = 90.0 nM 7.05 Mixed type inhibition of CYP2A6 (unknown origin) 36889653
PAM212 IC50 = 100.0 nM 7.0 Phototoxicity against mouse PAM212 cells assessed as cell growth inhibition prei... 30638875
Cytochrome P450 2A6 Ki = 250.0 nM 6.6 Mixed inhibition of CYP2A6 (unknown origin) 22696418
Cytochrome P450 2A6 Ki = 260.0 nM 6.58 Non competitive inhibition of CYP2A6 in human liver microsome using coumarin as ... 36889653
LoVo IC50 = 400.0 nM 6.4 Cytotoxicity against LoVo (human intestinal adenocarcinoma) cell line at 6.5 jou... 15837311
Cytochrome P450 2A6 IC50 = 460.0 nM 6.34 Inhibition of CYP2A6 (unknown origin) 36889653
LoVo IC50 = 700.0 nM 6.16 Cytotoxicity against LoVo (human intestinal adenocarcinoma) cell line at 3.2 jou... 15837311
LoVo IC50 = 700.0 nM 6.16 Phototoxicity against human LoVo cells exposed to irradiation with 3.75 J/cm'2 U... 19230658
LoVo IC50 = 700.0 nM 6.16 Photocytotoxicity against human LoVo cells treated 30 mins before 3.75 J/cm'2 UV... 18951030
HL-60 IC50 = 750.0 nM 6.12 Compound was evaluated for cell growth inhibition against HL 60 cell line by irr... 8893844
Acetylcholinesterase IC50 = 760.0 nM 6.12 Inhibition of acetylcholinesterase (unknown origin) using acetylcholine iodide a... 23746477
Cytochrome P450 2A6 Ki = 800.0 nM 6.1 Mechanism based inhibition of human cytochrome P450 2A6 measured by coumarin 7-h... 16248836
NON-PROTEIN TARGET IC50 = 900.0 nM 6.05 Photocytotoxicity against human NCTC 2544 cells treated 30 mins before 3.75 J/cm... 18951030
LoVo IC50 = 1100.0 nM 5.96 Photocytotoxicity against human LoVo cells treated 30 mins before 2.5 J/cm'2 UVA... 18951030
LoVo IC50 = 1100.0 nM 5.96 Phototoxicity against human LoVo cells exposed to irradiation with 2.5 J/cm'2 UV... 19230658
LoVo IC50 = 1100.0 nM 5.96 Cytotoxicity against LoVo (human intestinal adenocarcinoma) cell line at 2.5 jou... 15837311
Jurkat IC50 = 1200.0 nM 5.92 Photocytotoxicity against human JURKAT cells treated 30 mins before 2.5 J/cm'2 U... 18951030
Jurkat IC50 = 1200.0 nM 5.92 Phototoxicity against human Jurkat cells exposed to irradiation with 2.5 J/cm'2 ... 19230658

Literature References

PubMed DOI Target Context # Activities
31158845 10.1038/s41586-019-1291-3 ADMET 88
- 10.5281/zenodo.13943903 ADMET 79
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
3069958 10.1021/np50060a016 Salmonella typhimurium 13
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
469551 10.1021/np50001a005 DNA 10
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
16248836 10.2174/138920005774330639 Cytochrome P450 2A6 7
469551 10.1021/np50001a005 Saccharomyces cerevisiae 6
15161195 10.1021/jf0497298 Lactuca sativa 6
6195312 10.1021/np50028a027 CHO 6
16441065 10.1021/np058080d Unchecked 6
469551 10.1021/np50001a005 Candida albicans 6
23291118 10.1016/j.ejmech.2012.11.043 ADMET 5
19217697 10.1016/j.ejmech.2009.01.006 HeLa 5
33482600 10.1016/j.ejmech.2021.113171 ADMET 4
8164263 10.1021/jm00034a019 Nucleic Acid 4
- 10.6019/CHEMBL4495565 SARS-CoV-2 4
10425103 10.1021/jm991028s Unchecked 4
8632436 10.1021/jm950585l Ehrlich 4

Data from ChEMBL 36 via Core Engine