WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 318956
CAS#: 3902-71-4
Description: Trioxsalen is a photosenisitizer. It is obtained from several plants, mainly Psoralea corylifolia. Like other psoralens it causes photosensitization of the skin. It is administered either topically or orally in conjunction with UV-A (the least damaging form of ultraviolet light) for phototherapy treatment of vitiligo and hand eczema. After photoactivation it creates interstrand cross-links in DNA, which can cause programmed cell death unless repaired by cellular mechanisms. In research it can be conjugated to dyes for confocal microscopy and used to visualize sites of DNA damage.
MedKoo Cat#: 318956
Name: Trioxsalen
CAS#: 3902-71-4
Chemical Formula: C14H12O3
Exact Mass: 228.07864
Molecular Weight: 228.247
Elemental Analysis: C, 73.67; H, 5.30; O, 21.03
Synonym: NSC71047; NSC-71047; NSC 71047; Trioxsalen, trimethylpsoralen, Trioxysalen; Trisoralen.
IUPAC/Chemical Name: 2,5,9-trimethyl-7H-furo[3,2-g]chromen-7-one
InChi Key: FMHHVULEAZTJMA-UHFFFAOYSA-N
InChi Code: InChI=1S/C14H12O3/c1-7-4-12(15)17-14-9(3)13-10(6-11(7)14)5-8(2)16-13/h4-6H,1-3H3
SMILES Code: CC1=CC2=CC3=C(OC(=O)C=C3C)C(C)=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 228.247 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: Raviprakash K, Sun P, Raviv Y, Luke T, Martin N, Kochel T. Dengue virus photo-inactivated in presence of 1,5-iodonaphthylazide (INA) or AMT, a psoralen compound (4'-aminomethyl-trioxsalen) is highly immunogenic in mice. Hum Vaccin Immunother. 2013 Nov;9(11):2336-41. Epub 2013 Jul 8. PubMed PMID: 23835446; PubMed Central PMCID: PMC3981842.
2: Hadjipavlou-Litina D, E Bariamis S, Militsopoulou M, Athanassopoulos CM, Papaioannou D. Trioxsalen derivatives with lipoxygenase inhibitory activity. J Enzyme Inhib Med Chem. 2009 Dec;24(6):1351-6. doi: 10.3109/14756360902932776. PubMed PMID: 19912068.
3: Sehgal VN. Role of tacrolimus (FK506) 0.1% ointment WW in vitiligo in children and imperatives of combine therapy with Trioxsalen and Silymarin suspension in progressive vitiligo. J Eur Acad Dermatol Venereol. 2009 Oct;23(10):1218-9. doi: 10.1111/j.1468-3083.2009.03128.x. Epub 2009 Mar 3. PubMed PMID: 19192018.
4: Sánchez Ruderisch H, Aryee-Boi J, Schwarz C, Radenhausen M, Tebbe B. Shower PUVA: a novel variant of photochemotherapy. Distribution of photosensitivity and accumulation of trioxsalen in the skin. Skin Pharmacol Physiol. 2004 May-Jun;17(3):129-32. PubMed PMID: 15087592.
5: Sánchez Ruderisch H, Schwarz C, Shang J, Tebbe B. Trioxsalen in the presence of UVA is able to induce nuclear factor kappa B binding activity in HaCaT keratinocytes. Skin Pharmacol Appl Skin Physiol. 2002 Sep-Oct;15(5):335-41. PubMed PMID: 12239428.
6: Snellman E, Rantanen T, Sundell J. Cumulative UV radiation dose and outcome in clinical practice: effectiveness of trioxsalen bath PUVA with minimal UVA exposure. Photodermatol Photoimmunol Photomed. 2000 Oct;16(5):207-10. PubMed PMID: 11068859.
7: Kuusilehto A, Happonen RP, Peltola J, Lehtinen R, Jansén CT. The effect of PUVA on langerhans cells in rat oral epithelium photosensitized with systemic methoxsalen or topical trioxsalen. Photodermatol Photoimmunol Photomed. 2000 Jun;16(3):129-33. PubMed PMID: 10885443.
8: Hannuksela-Svahn A, Sigurgeirsson B, Pukkala E, Lindelöf B, Berne B, Hannuksela M, Poikolainen K, Karvonen J. Trioxsalen bath PUVA did not increase the risk of squamous cell skin carcinoma and cutaneous malignant melanoma in a joint analysis of 944 Swedish and Finnish patients with psoriasis. Br J Dermatol. 1999 Sep;141(3):497-501. PubMed PMID: 10583054.
9: Wainwright NJ, MacLeod TM, Ferguson J. Bath PUVA--an investigation of the distribution of trioxsalen (TMP) and 8-methoxypsoralen (8-MOP) in bathwater. Photodermatol Photoimmunol Photomed. 1997 Feb-Apr;13(1-2):17-20. PubMed PMID: 9361123.
10: Hannuksela A, Pukkala E, Hannuksela M, Karvonen J. Cancer incidence among Finnish patients with psoriasis treated with trioxsalen bath PUVA. J Am Acad Dermatol. 1996 Nov;35(5 Pt 1):685-9. PubMed PMID: 8912561.
11: Lindelöf B, Sigurgeirsson B, Tegner E, Larkö O, Berne B. Comparison of the carcinogenic potential of trioxsalen bath PUVA and oral methoxsalen PUVA. A preliminary report. Arch Dermatol. 1992 Oct;128(10):1341-4. PubMed PMID: 1417020.
12: Hannuksela M, Karvonen J. Carcinogenicity of trioxsalen bath PUVA. J Am Acad Dermatol. 1989 Oct;21(4 Pt 1):813-4. PubMed PMID: 2808807.
13: Kekelidze MG, Razin SV, Lukanidin EM. [A preparation of short DNA chains synthesized in vivo after introduction into DNA from live cells of trioxsalen crosslinks is not enriched by replication initiation regions]. Mol Biol (Mosk). 1986 Mar-Apr;20(2):378-86. Russian. PubMed PMID: 3010081.
14: Hannuksela M, Kokkonen EL. Short-contact trioxsalen cream PUVA. Photodermatol. 1985 Dec;2(6):398-400. PubMed PMID: 4094932.
15: Karvonen J, Hannuksela M. Long term results of topical trioxsalen PUVA in lichen planus and nodular prurigo. Acta Derm Venereol Suppl (Stockh). 1985;120:53-5. PubMed PMID: 3869416.
16: Turjanmaa K, Salo H, Reunala T. Comparison of trioxsalen bath and oral methoxsalen PUVA in psoriasis. Acta Derm Venereol. 1985;65(1):86-8. PubMed PMID: 2578716.
17: Mohamed ME, Loutfy MA. Spectrofluorimetric determination of trioxsalen. Pharmazie. 1984 Oct;39(10):708-9. PubMed PMID: 6522453.
18: Berne B, Fischer T, Michaëlsson G, Norén P. Long-term safety of trioxsalen bath PUVA treatment: an 8-year follow-up of 149 psoriasis patients. Photodermatol. 1984 Feb;1(1):18-22. PubMed PMID: 6531278.
19: Jansén CT, Karvonen J, Malmiharju T. PUVA therapy for polymorphous light eruptions: comparison of systemic methoxsalen and topical trioxsalen regimens and evaluation of local protective mechanisms. Acta Derm Venereol. 1982;62(4):317-20. PubMed PMID: 6183864.
20: Revet B, Benichou D. Electron microscopy of AD5 replicating molecules after in vivo photocrosslinking with trioxsalen. Virology. 1981 Oct 15;114(1):60-70. PubMed PMID: 7281518.
