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Details

Stereochemistry ACHIRAL
Molecular Formula C44H32N4O4
Molecular Weight 680.7493
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TEMOPORFIN

SMILES

OC1=CC=CC(=C1)C2=C3NC(C=C3)=C(C4=NC(C=C4)=C(C5=CC=C(N5)C(=C6CCC2=N6)C7=CC(O)=CC=C7)C8=CC(O)=CC=C8)C9=CC(O)=CC=C9

InChI

InChIKey=LYPFDBRUNKHDGX-LWQDQPMZSA-N
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-

HIDE SMILES / InChI

Molecular Formula C44H36N4O4
Molecular Weight 684.781
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Temoporfin is a photosensitizer (based on chlorin) used in photodynamic therapy for the treatment of squamous cell carcinoma of the head and neck. It is marketed in the European Union under the brand name Foscan. It is used in patients in whom other treatments have stopped working, and who are not suitable for radiotherapy (treatment with radiation), surgery or systemic chemotherapy (medicines used to treat cancer; ‘systemic’ means that they are given as treatments throughout the body). When Foscan is injected, temoporfin is distributed within the body, including within the tumour. When it is illuminated with laser light of a specific wavelength, temoporfin is activated and reacts with oxygen in the cells to create a highly reactive and toxic type of oxygen. This kills the cells by reacting with and destroying their components, such as their proteins and DNA. By restricting the illumination to the tumour, cell damage is limited to the tumour cells, leaving other areas of the body unaffected. The U.S. Food and Drug Administration (FDA) declined to approve Foscan in 2000. The EU approved its use in June 2001.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
7.6 nM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
Foscan
Palliative
Unknown
Palliative
Unknown

PubMed

Sample Use Guides

In Vivo Use Guide
Treatment with Foscan is a two-step process: the medicine is given first, and then it is activated using a laser. The medicine is given by an indwelling intravenous cannula (a thin tube permanently inserted into a vein) as a single slow injection over at least six minutes. The dose is 0.15 mg per kilogram body weight. Four days later, the entire surface of the tumour and the surrounding 0.5 cm margin is illuminated with light from a laser at a specific wavelength, using a fibre-optic cable. Each area of the tumour should be illuminated only once during each treatment. During treatment, other areas of the body should be shielded from the light so that the activation of the medicine is limited to the tumour. If a second treatment is necessary, this should take place at least four weeks later.
Route of Administration: Intravenous
In Vitro Use Guide
mTHPC((Temoporfin)-invasomes and mTHPC-ethanolic solution used at a 2uM mTHPC-concentration and photoirradiation at 20J/cm(2) were able to reduce survival of HT29 cells and especially of A431 cells.
Substance Class Chemical
Record UNII
FU21S769PF
Record Status Validated (UNII)
Record Version