Temoporfin

Temoporfin (INN) is a photosensitizer (based on chlorin) used in photodynamic therapy for the treatment of squamous cell carcinoma of the head and neck[1] .[2] It is marketed in the European Union under the brand name Foscan. The U.S. Food and Drug Administration (FDA) declined to approve Foscan in 2000. The EU approved its use in June 2001.[3]

Temoporfin

Clinical data
AHFS/Drugs.com	International Drug Names
License data	EU EMA: by INN
ATC code	L01XD05 (WHO)
Legal status
Legal status	In general: ℞ (Prescription only)
Identifiers
IUPAC name 3,3',3'',3'''-(2,3-dihydroporphyrin-5,10,15,20-tetrayl)tetraphenol
CAS Number	122341-38-2^Y
PubChem CID	60751
ChemSpider	54754
UNII	FU21S769PF
KEGG	D06066^Y
ChEMBL	ChEMBL383675
CompTox Dashboard (EPA)	DTXSID7048619
ECHA InfoCard	100.152.970
Chemical and physical data
Formula	C44H32N4O4
Molar mass	680.764 g·mol^−1
3D model (JSmol)	Interactive image
SMILES C1CC2=NC1=C(C3=CC=C(N3)C(=C4C=CC(=N4)C(=C5C=CC(=C2C6=CC(=CC=C6)O)N5)C7=CC(=CC=C7)O)C8=CC(=CC=C8)O)C9=CC(=CC=C9)O
InChI InChI=1S/C44H32N4O4/c49-29-9-1-5-25(21-29)41-33-13-15-35(45-33)42(26-6-2-10-30(50)22-26)37-17-19-39(47-37)44(28-8-4-12-32(52)24-28)40-20-18-38(48-40)43(36-16-14-34(41)46-36)27-7-3-11-31(51)23-27/h1-17,19,21-24,46-47,49-52H,18,20H2/b41-33-,41-34-,42-35-,42-37-,43-36-,43-38-,44-39-,44-40- Key:LYPFDBRUNKHDGX-LWQDQPMZSA-N
(verify)

Good results were obtained in 21 of 35 patients treated in Germany.[4]

It is photoactivated at 652 nm[5] i.e. by red light.

Patients can remain photosensitive for several weeks after treatment.[2]

Further reading

• Relationship between subcellular localisation of Foscan and caspase activation in photosensitised MCF-7 cells. Marchal et al. 2007

References

1. Lorenz KJ, Maier H (April 2008). "[Squamous cell carcinoma of the head and neck. Photodynamic therapy with Foscan]". HNO (in German). 56 (4): 402–9. doi:10.1007/s00106-007-1573-1. PMID 17516041.
2. O'Connor, Aisling E; Gallagher, William M; Byrne, Annette T (2009). "Porphyrin and Nonporphyrin Photosensitizers in Oncology: Preclinical and Clinical Advances in Photodynamic Therapy. Photochemistry and Photobiology, Sep/Oct 2009". Photochemistry and Photobiology.
3. HighBeam Foscan approval saves Scotia's skin.
4. Johannes Lorenz, Kai; Maier, Heinz (2009). "Photodynamic therapy with meta-tetrahydroxyphenylchlorin (Foscan®) in the management of squamous cell carcinoma of the head and neck: experience with 35 patients". European Archives of Oto-Rhino-Laryngology. 266 (12): 1937–1944. doi:10.1007/s00405-009-0947-2. PMID 19290535.
5. "Porphyrin and Nonporphyrin Photosensitizers in Oncology: Preclinical and Clinical Advances in Photodynamic Therapy". Photochemistry and Photobiology. 2009.