WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 100620
Description: Methoxsalen is a naturally occurring substance isolated from the seeds of the plant Ammi majus with photoactivating properties. As a member of the family of compounds known as psoralens or furocoumarins, methoxsalen's exact mechanism of action is unknown; upon photoactivation, methoxsalen has been observed to bind covalently to and crosslink DNA. Check for active clinical trials or closed clinical trials using this agent. (NCI Thesaurus).
MedKoo Cat#: 100620
Chemical Formula: C12H8O4
Exact Mass: 216.04226
Molecular Weight: 216.19
Elemental Analysis: C, 66.67; H, 3.73; O, 29.60
Synonym: 8methoxypsoralen; Methoxypsoralen. US brand names: Ammoidin; Oxsorale
IUPAC/Chemical Name: 9-methoxy-7H-furo[3,2-g]chromen-7-one
InChi Key: QXKHYNVANLEOEG-UHFFFAOYSA-N
InChi Code: 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
SMILES Code: O=C1C=CC2=CC3=C(OC=C3)C(OC)=C2O1
Appearance: Solid powder
Purity: >98% (or refer to the Certificate of Analysis)
Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility: Soluble in DMSO, not in water
Shelf Life: >2 years if stored properly
Drug Formulation: This drug may be formulated in DMSO
Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code: 2934.99.9001
The following data is based on the product molecular weight 216.19 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.
|Concentration / Solvent Volume / Mass||1 mg||5 mg||10 mg|
|1 mM||1.15 mL||5.76 mL||11.51 mL|
|5 mM||0.23 mL||1.15 mL||2.3 mL|
|10 mM||0.12 mL||0.58 mL||1.15 mL|
|50 mM||0.02 mL||0.12 mL||0.23 mL|
1: Zavigel'skii GB, Kotova VY. [SOS repair of 8-methoxypsoralene monoadducts in
DNA of lambda bacteriophage and plasmids is mediated by MucA'2B, but not UmuD'2c
(PolV) polymerase]. Genetika. 2013 Dec;49(12):1370-5. Russian. PubMed PMID:
2: Li J, Ma B, Zhang Q, Yang X, Sun J, Tang B, Cui G, Yao D, Liu L, Gu G, Zhu J,
Wei P, Ouyang P. Simultaneous determination of osthole, bergapten and
isopimpinellin in rat plasma and tissues by liquid chromatography-tandem mass
spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2014 Nov
1;970:77-85. doi: 10.1016/j.jchromb.2014.06.014. Epub 2014 Jun 21. PubMed PMID:
Methoxsalen is a naturally occurring photoactive substance found in the seeds of the Ammi majus (Umbelliferae) plant. It belongs to a group of compounds known as psoralens or furocoumarins. The chemical name of methoxsalen is 9-methoxy-7H-furo[3,2-g]-benzopyran-7-one. Each mL of UVAOEXÂ® (methoxsalen, 8-methoxypsoralen) Sterile Solution contains methoxsalen 20 mcg, propylene glycol 50 mg, sodium chloride 8 mg, sodium acetate 1.75 mg, ethanol 0.05 mL, glacial acetic acid 0.0012 mL, and Water for Injection q.s.to 1.0 mL. UVAOEXÂ® is used in combination with the UVARÂ® or UVARÂ® XTSÂ™ Photopheresis System to extracorporeally treat leukocyte enriched buffy coat.
Mechanism of action
The exact mechanism of action of methoxsalen is not known.The best-known bio-chemical reaction of methoxsalen is wrth DNA. Methoxsalen,upon photoactivation,conjugates and forms covalent bonds with DNA which leads to the formation of both mono functional (addition to a single strand of DNA) and bifunctional adducts (cross linking of psoralen to both strands of DNA). For the palliative treatment of Cutaneous T-Cell Lymphoma, Photopheresis consists of removing a portion of the patient's blood and separating the red blood cell from the white cell layer (buffy coat) by centrifugation. The red cells are returned to the patient and the UVADEXÂ® Sterile Solutionis then injected into the instrument and mixed with the buffy coat. The instrument then irradiates this drug-cell mixture with ultra violet light (UVA light, 320-400 nm) and returns the treated cells to the patient. See the appropriate Operator's Manual for details of this process. Although extra corporeal phototherapy exposes less than 10% of the total body burden of malignant cells to methoxsalen plus light, some patients achieve a complete response. Animal studies suggest that the photopheresis may activate an immune-mediated response against the malignant T-cells.
Use of the UVARÂ® and UVARÂ® XTSÂ™ Systems after oral administration of methoxsalen were previously approved for the treatment of Cutaneous T-Cell Lymphoma. Interpatient variability in peak plasma concentration after an oral dose of methoxsalen ranges from 6 to 15 fold. UVADEXÂ® is injected directly into the separated buffy coat in the instrument in an attempt to diminish this interpatient variability and to improve the exposure of the cells to the drug. Methoxsalen is reversibly bound to serum albumin and is also preferentially taken up by epidermal cells. Methoxsalen is rapidly metabolized in humans, with approximately 95% of the drug excreted as metabolites in the urine within 24 hours. Systemic administration of methoxsalen followed by UVA exposure leads to cell injury. The most obvious manifestation of this injury after skin exposure is delayed erythema, which may not begin for several hours and peaks at 48-72 hours.The inflammation is followed over several days to weeks, by repair which is manifested by increased melanization of the epidermis and thickening of the stratum corneum. The total dose of methoxsalen delivered in UVADEXÂ® is substantially lower (approximately 200 times) than that used with oral administration.