Temoporfin

Chemical compound

Identifiers

CAS Number

PubChem CID

ChemSpider

UNII

KEGG

ChEMBL

CompTox Dashboard (EPA)

ECHA InfoCard100.152.970

Chemical and physical dataFormulaC₄₄H₃₂N₄O₄Molar mass680.764 g·mol⁻¹3D model (JSmol)

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)

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]

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

It is photoactivated at 652 nm^[2] i.e. by red light.

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

References

^ Lorenz KJ, Maier H (April 2008). "[Squamous cell carcinoma of the head and neck. Photodynamic therapy with Foscan]". Hno (in German). 56 (4): 402–409. doi:10.1007/s00106-007-1573-1. PMID 17516041.
^ ^a ^b ^c O'Connor AE, Gallagher WM, Byrne AT (2009). "Porphyrin and nonporphyrin photosensitizers in oncology: preclinical and clinical advances in photodynamic therapy". Photochemistry and Photobiology. 85 (5): 1053–1074. doi:10.1111/j.1751-1097.2009.00585.x. PMID 19682322. S2CID 205950773.
^ "Foscan approval saves Scotia's skin". HighBeam. Archived from the original on 2012-11-04.
^ Lorenz KJ, Maier H (December 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. S2CID 5892034.

Block microtubule assembly	Vinca alkaloids (Vinblastine^# Vincristine^# Vindesine Vinflunine^§ Vinorelbine^#)
Block microtubule disassembly	Taxanes (Cabazitaxel Docetaxel^# Larotaxel Ortataxel^† Paclitaxel^# Tesetaxel) Epothilones (Ixabepilone)

Folic acid	Dihydrofolate reductase inhibitor (Aminopterin Methotrexate^# Pemetrexed Pralatrexate) Thymidylate synthase inhibitor (Pemetrexed Raltitrexed)
Purine	Adenosine deaminase inhibitor (Pentostatin) Halogenated/ribonucleotide reductase inhibitors (Cladribine Clofarabine Fludarabine) Nelarabine Thiopurine (Mercaptopurine^# Tioguanine^#)
Pyrimidine	Thymidylate synthase inhibitor (Capecitabine^# Carmofur Doxifluridine Floxuridine Fluorouracil^# Tegafur (+gimeracil/oteracil)) DNA polymerase inhibitor (Cytarabine^# +daunorubicin) Ribonucleotide reductase inhibitor (Gemcitabine^#) Hypomethylating agent (Azacitidine Decitabine)
Deoxyribonucleotide	Ribonucleotide reductase inhibitor (Hydroxycarbamide^#)

I	Camptotheca (Belotecan Camptothecin Cositecan^† Etirinotecan pegol^† Exatecan Gimatecan Irinotecan^# Lurtotecan^‡ Rubitecan^‡ Silatecan^§ Topotecan)
II	Podophyllum (Etoposide^# Teniposide)
II+Intercalation	Anthracyclines (Aclarubicin Amrubicin^† Daunorubicin^# (+cytarabine) Doxorubicin^# Epirubicin Idarubicin Pirarubicin Valrubicin Zorubicin) Anthracenediones (Mitoxantrone Losoxantrone Pixantrone) Amsacrine Bisantrene Crisnatol Menogaril^§

Alkylating	Nitrogen mustards: Bendamustine^# Chlormethine Cyclophosphamide^# (Ifosfamide^# Trofosfamide) Chlorambucil^# Melphalan (Melphalan flufenamide) Prednimustine Uramustine Nitrosoureas: Carmustine Fotemustine Lomustine (Semustine) Nimustine Ranimustine Streptozocin Alkyl sulfonates: Busulfan (Mannosulfan Treosulfan) Aziridines: Carboquone Thiotepa Triaziquone Triethylenemelamine
Platinum-based	Carboplatin^# Cisplatin^# Dicycloplatin Nedaplatin Oxaliplatin^# Satraplatin
Nonclassical	Altretamine Hydrazines (Procarbazine^#) Etoglucid Mitobronitol Pipobroman Triazenes (Dacarbazine^# Mitozolomide^§ Temozolomide)
Intercalation	Streptomyces (Dactinomycin^# Bleomycin^# Mitomycins Plicamycin)

Other

Enzyme inhibitors	FI (Tipifarnib^§) CDK inhibitors (Abemaciclib Alvocidib^† Palbociclib Ribociclib Seliciclib^†) PrI Bortezomib Carfilzomib Oprozomib Ixazomib PhI (Anagrelide) IMPDI (Tiazofurin^§) LI (Masoprocol) PARP inhibitor (Niraparib +abiraterone acetate Olaparib Rucaparib) HDAC (Belinostat Entinostat Panobinostat Romidepsin Vorinostat) PIKI (Pi3K) (Alpelisib Copanlisib Duvelisib Idelalisib Umbralisib^‡)
Receptor antagonists	ERA (Atrasentan) Retinoid X receptor (Bexarotene) Sex steroid (Testolactone)
Other/ungrouped	Adagrasib Aflibercept Arsenic trioxide Asparagine depleters (Asparaginase^#/Pegaspargase) Axicabtagene ciloleucel Belzutifan Bexarotene Brexucabtagene autoleucel Celecoxib Ciltacabtagene autoleucel Demecolcine Denileukin diftitox Elesclomol^§ Elsamitrucin Enasidenib Epacadostat Eribulin Estramustine phosphate Glasdegib Idecabtagene vicleucel Ivosidenib Lifileucel Lonidamine Lucanthone Lurbinectedin Mitoguazone Mitotane Oblimersen^† Omacetaxine mepesuccinate Plitidepsin Retinoids (Alitretinoin Tretinoin^#) Selinexor Sitimagene ceradenovec Sotorasib Tagraxofusp Talimogene laherparepvec Tazemetostat Tebentafusp Tiazofurine Tigilanol tiglate Tisagenlecleucel Trabectedin Veliparib Venetoclax Verdinexor Vosaroxin