Methoxsalen

Catalog No.S1952 Synonyms: Xanthotoxin, NCI-C55903

Methoxsalen Chemical Structure

Molecular Weight(MW): 216.19

Methoxsalen is a naturally occurring photoactive substance found in the seeds of the Ammi majus (Umbelliferae) plant, used in the diagnosis and treatment of psoriasis; A CYP2A5/6 inhibitor.

Size Price Stock Quantity  
In DMSO USD 130 In stock
USD 97 In stock
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Biological Activity

Description Methoxsalen is a naturally occurring photoactive substance found in the seeds of the Ammi majus (Umbelliferae) plant, used in the diagnosis and treatment of psoriasis; A CYP2A5/6 inhibitor.
Targets
CYP2A5 [6] CYP2A6 [6]
In vitro

Methoxsalen inhibits CYP2A6 (Ki = 0.8 μM) with about 3.5- 94-fold greater potency than other P450s, except for CYP1A2 (Ki = 0.2 μM). Methoxsalen shows noncompetitive inhibition of nicotine metabolism, with an apparent Ki value of 0.1 μM in cDNA-expressing microsomes. [1] Methoxsalen is metabolized in human liver microsomes at the rate of 50-100 pmol/mg protein/min (approx. 30% of the activity in mouse liver microsomes). Methoxsalen is a very potent inhibitor of human cytochrome P450 2A6 (CYP2A6) and mouse Cyp2a-5-mediated coumarin 7-hydroxylation in vitro. [2]

In vivo Methoxsalen results in a significant decrease in the following factors: number and diameter of corpus lutei, Graafian follicles, diameter of granulosa cell layer and oocytes, number of primordial and primary and growing follicles, while the number of atretic follicle is increased. Methoxsalen also significantly reduces circulating estrogen levels in blood serum of oogenesis Balb/C mice. [3] Methoxsalen dose-dependently stimulates a sustained increase in short-circuit current in the mouse jejunum. Methoxsalen increases the open probability of the basolateral IK(Ca) channel of isolated crypts in the mouse jejunum. [4] Methoxsalen effectively reverses trimethyltin (TMT)-induced memory impairment on both Y-maze and passive avoidance tests in mice. Methoxsalen inhibits brain AchE activity. Methoxsalen significantly ameliorates the level of oxidative stress. [5]

Protocol

Solubility (25°C)

In vitro DMSO 43 mg/mL (198.89 mM)
Ethanol 5 mg/mL (23.12 mM)
Water Insoluble

* Please note that Selleck tests the solubility of all compounds in-house, and the actual solubility may differ slightly from published values. This is normal and is due to slight batch-to-batch variations.

Chemical Information

Molecular Weight 216.19
Formula

C12H8O4

CAS No. 298-81-7
Storage powder
in solvent
Synonyms Xanthotoxin, NCI-C55903

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Clinical Trial Information

NCT Number Recruitment Conditions Sponsor/Collaborators Start Date Phases
NCT03563040 Not yet recruiting Lymphoma T-Cell Cutaneous|Mycosis Fungoides/Sezary Syndrome European Organisation for Research and Treatment of Cancer - EORTC|Mallinckrodt December 1 2018 Phase 2
NCT03605940 Not yet recruiting Acute-graft-versus-host Disease Central Hospital Nancy France October 1 2018 Phase 2
NCT03512756 Recruiting Pancreatic Cancer Tyme Inc March 27 2018 Phase 2
NCT02524847 Recruiting Steroid Refractory Acute Graft Versus Host Disease Mallinckrodt January 20 2016 Phase 3
NCT02181257 Active not recruiting Bronchiolitis Obliterans Syndrome (BOS) Washington University School of Medicine|Centers for Medicare and Medicaid Services|Mallinckrodt January 2015 --
NCT02322190 Suspended Chronic Graft vs. Host Disease|Graft vs Host Disease|Graft-Versus-Host Disease National Cancer Institute (NCI)|National Institutes of Health Clinical Center (CC) December 20 2014 Phase 2

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P450 (e.g. CYP17) Signaling Pathway Map

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Cell Lines Assay Type Concentration Incubation Time Formulation Activity Description PMID