Temoporfin

    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 202865

CAS#: 122341-38-2

Description: Temoporfin, also known as m-THPC or KW-2345, is a synthetic light-activated chlorin with photodynamic activity. Upon systemic administration, temoporfin distributes throughout the body and is taken up by tumor cells. Upon stimulation of temoporfin by non-thermal laser light (at 652 nm), and in the presence of oxygen, this agent produces highly reactive short-lived singlet oxygen and other reactive oxygen radicals, resulting in local damage to tumor cells. This may kill tumor cells and may reduce the tumor size.


Chemical Structure

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Temoporfin
CAS# 122341-38-2

Theoretical Analysis

MedKoo Cat#: 202865
Name: Temoporfin
CAS#: 122341-38-2
Chemical Formula: C44H32N4O4
Exact Mass: 680.24236
Molecular Weight: 680.75
Elemental Analysis: C, 77.63; H, 4.74; N, 8.23; O, 9.40

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Synonym: m-THPC; mTHPC; EF 9; KW-2345; KW2345; KW 2345; 3,​3',​3'',​3'''-​(7,​8-​Dihydroporphyrin-​5,​10,​15,​20-​tetrayl)​tetraphenol; 5,​10,​15,​20-​Tetra(m-​hydroxyphenyl)​chlorin; 5,​10,​15,​20-​Tetrakis(m-​hydroxyphenyl)​chlorin; 8-​Dihydroporphyrin-​5; Generic name: temoporfin. Brand name: Foscan; Fosgel; Foslip; Foslipos; Fospeg.

IUPAC/Chemical Name: 3,3',3'',3'''-(2,3-dihydroporphyrin-5,10,15,20-tetrayl)tetraphenol

InChi Key: SPFYFBIKUARTFZ-DLJQTLRXSA-N

InChi Code: InChI=1S/C44H34N4O4/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/h1-17,19,21-24,38,40,45,48-52H,18,20H2/b41-33-,42-35-,43-36-,44-39-

SMILES Code: OC1=CC=CC(/C2=C3CCC(/C(C4=CC(O)=CC=C4)=C5C=C/C(N/5)=C(C6=CC(O)=CC=C6)/C(C=C/7)=NC7=C(C8=CC(O)=CC=C8)/C9=CC=C2N9)=N\3)=C1

Appearance: Black solid powder

Purity: >95% (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

Safety Data Sheet (SDS):

Preparing Stock Solutions

The following data is based on the product molecular weight 680.75 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.

Recalculate based on batch purity %
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

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 1: Yu Q, Rodriguez EM, Naccache R, Forgione P, Lamoureux G, Sanz-Rodriguez F, Scheglmann D, Capobianco JA. Chemical modification of temoporfin - a second generation photosensitizer activated using upconverting nanoparticles for singlet oxygen generation. Chem Commun (Camb). 2014 Sep 1. [Epub ahead of print] PubMed PMID: 25174720.

2: Reshetov V, Lassalle HP, François A, Dumas D, Hupont S, Gräfe S, Filipe V, Jiskoot W, Guillemin F, Zorin V, Bezdetnaya L. Photodynamic therapy with conventional and PEGylated liposomal formulations of mTHPC (temoporfin): comparison of treatment efficacy and distribution characteristics in vivo. Int J Nanomedicine. 2013;8:3817-31. doi: 10.2147/IJN.S51002. Epub 2013 Oct 8. PubMed PMID: 24143087; PubMed Central PMCID: PMC3797282.

3: Decker C, Steiniger F, Fahr A. Transfer of a lipophilic drug (temoporfin) between small unilamellar liposomes and human plasma proteins: influence of membrane composition on vesicle integrity and release characteristics. J Liposome Res. 2013 Jun;23(2):154-65. doi: 10.3109/08982104.2013.770017. Epub 2013 Apr 16. PubMed PMID: 23590339.

4: Wagner A, Kiesslich T, Neureiter D, Friesenbichler P, Puespoek A, Denzer UW, Wolkersdörfer GW, Emmanuel K, Lohse AW, Berr F. Photodynamic therapy for hilar bile duct cancer: clinical evidence for improved tumoricidal tissue penetration by temoporfin. Photochem Photobiol Sci. 2013 Jun;12(6):1065-73. doi: 10.1039/c3pp25425a. Epub 2013 Apr 4. PubMed PMID: 23558738.

5: Decker C, Schubert H, May S, Fahr A. Pharmacokinetics of temoporfin-loaded liposome formulations: correlation of liposome and temoporfin blood concentration. J Control Release. 2013 Mar 28;166(3):277-85. doi: 10.1016/j.jconrel.2013.01.005. Epub 2013 Jan 11. PubMed PMID: 23313962.

6: Nyst HJ, Wildeman MA, Indrasari SR, Karakullukcu B, van Veen RL, Adham M, Stewart FA, Levendag PC, Sterenborg HJ, Tan IB. Temoporfin mediated photodynamic therapy in patients with local persistent and recurrent nasopharyngeal carcinoma after curative radiotherapy: a feasibility study. Photodiagnosis Photodyn Ther. 2012 Sep;9(3):274-81. doi: 10.1016/j.pdpdt.2012.07.002. Epub 2012 Aug 23. PubMed PMID: 22959807.

7: Durbec M, Cosmidis A, Fuchsmann C, Ramade A, Céruse P. Efficacy and safety of photodynamic therapy with temoporfin in curative treatment of recurrent carcinoma of the oral cavity and oropharynx. Eur Arch Otorhinolaryngol. 2013 Mar;270(4):1433-9. doi: 10.1007/s00405-012-2083-7. Epub 2012 Aug 29. PubMed PMID: 22927020.

8: Rojnik M, Kocbek P, Moret F, Compagnin C, Celotti L, Bovis MJ, Woodhams JH, Macrobert AJ, Scheglmann D, Helfrich W, Verkaik MJ, Papini E, Reddi E, Kos J. In vitro and in vivo characterization of temoporfin-loaded PEGylated PLGA nanoparticles for use in photodynamic therapy. Nanomedicine (Lond). 2012 May;7(5):663-77. doi: 10.2217/nnm.11.130. PubMed PMID: 22630150.

9: Reshetov V, Zorin V, Siupa A, D'Hallewin MA, Guillemin F, Bezdetnaya L. Interaction of liposomal formulations of meta-tetra(hydroxyphenyl)chlorin (temoporfin) with serum proteins: protein binding and liposome destruction. Photochem Photobiol. 2012 Sep-Oct;88(5):1256-64. doi: 10.1111/j.1751-1097.2012.01176.x. Epub 2012 Jul 9. PubMed PMID: 22607362.

10: Aicher D, Gräfe S, Stark CB, Wiehe A. Synthesis of β-functionalized temoporfin derivatives for an application in photodynamic therapy. Bioorg Med Chem Lett. 2011 Oct 1;21(19):5808-11. doi: 10.1016/j.bmcl.2011.07.113. Epub 2011 Aug 8. PubMed PMID: 21885278.

Temoporfin

10.0mg / Not available


Additional Information

Temoporfin (INN) is a photosensitizer used in chemotherapy for the treatment of squamous cell carcinoma of the head and neck. In October 2001, Foscan® was approved in the European Union, Norway & Iceland as a local therapy for the palliative treatment of patients with advanced head and neck cancer who have failed prior therapies and are unsuitable for radiotherapy, surgery or systemic chemotherapy.
 
Foscan injection contains the active ingredient temoporfin, which is a type of medicine called a photosensitising agent. It is used in photodynamic therapy (PDT) of advanced head and neck cancer. The medicine is administered by injection into a vein and is given 90 hours to distribute around the body, including into the cancer cells. The medicine doesnÂ’t do anything until it is activated by a particular type of light. After 90 hours, a specialist in photodynamic therapy will direct a laser light source very precisely at the cancer. This light activates the medicine that is in the cancer cells, causing it to destroy them. The aim of the treatment is reduce symptoms by shrinking the cancer. This is called palliative treatment. It will not cure the cancer. Normally only one treatment is given, but this may be repeated after a few weeks.
 
Temoporfin (INN) is marketed in the European Union under the brand name Foscan. The US FDA deemed Foscan non-approvable in 2000. The EU approved its use in June 2001. It is photoactivated at 652 nm ie by red light. Patients can remain photosensitive for several weeks after treatment. [source: http://en.wikipedia.org/wiki/Temoporfin].
 
Current developer:    Biolitec Pharma Ltd.