TEMOPORFIN

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 Search

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

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: http://www.ema.europa.eu/docs/en_GB/document_library/EPAR_-_Summary_for_the_public/human/000318/WC500024392.pdf
Curator's Comment: Description was created based on several sources, including http://www.ncbi.nlm.nih.gov/pubmed/21848905

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 Target	Pharmacology	Potency
cell proliferation 28 Target ID: GO:0008283 Sources: http://www.ncbi.nlm.nih.gov/pubmed/16722648	Inhibitor 8297	7.6 nM [IC50]
Apoptosis 155 Target ID: map04210 Sources: http://www.ncbi.nlm.nih.gov/pubmed/19211252	Activator 1430
reactive oxygen species biosynthetic process 37 Target ID: GO:1903409 Sources: http://www.ncbi.nlm.nih.gov/pubmed/19211252	Activator 1430

Conditions

Condition	Modality	Highest Phase	Product
Head and neck squamous cell carcinoma 32 Sources: http://www.ema.europa.eu/docs/en_GB/document_library/EPAR_-_Product_Information/human/000318/WC500024398.pdf	Palliative	Approved 8429	Foscan Approved Use Foscan is indicated for the palliative treatment of patients with advanced head and neck squamous cell carcinoma failing prior therapies and unsuitable for radiotherapy, surgery or systemic chemotherapy. Launch Date 1.00379519E12
Cholangiocarcinoma 17 Sources: http://www.ncbi.nlm.nih.gov/pubmed/23993847	Palliative	Phase II 1132	Unknown Approved Use Unknown
Nasopharyngeal carcinoma 8 Sources: http://www.ncbi.nlm.nih.gov/pubmed/25917042	Palliative	Phase II 1132	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Comparative biodistribution of meta-Tetra(Hydroxyphenyl) chlorin in multiple species: clinical implications for photodynamic therapy.	1997	9142684
Efficacy of temoporfin-loaded invasomes in the photodynamic therapy in human epidermoid and colorectal tumour cell lines.	2010 Dec 2	20797872
Temoporfin (Foscan®, 5,10,15,20-tetra(m-hydroxyphenyl)chlorin)--a second-generation photosensitizer.	2011 Nov-Dec	21848905

Patents

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 Created by `admin` on `Fri Dec 15 17:49:12 UTC 2023` Edited by `admin` on `Fri Dec 15 17:49:12 UTC 2023`
Record UNII	FU21S769PF
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

TEMOPORFIN

Official Name

English

EF-9

Code

English

TEMOPORFIN [EMA EPAR]

Common Name

English

TEMOPORFIN [MART.]

Common Name

English

PHENOL, 3,3',3'',3'''-(7,8-DIHYDRO-21H,23H-PORPHINE-5,10,15,20-TETRAYL)TETRAKIS-

Common Name

English

TEMOPORFIN [USAN]

Common Name

English

EF9

Code

English

TEMOPORFIN [MI]

Common Name

English

3,3',3'',3'''-(7,8-DIHYDROPORPHYRIN-5,10,15,20-TETRAYL)TETRAPHENOL

Common Name

English

temoporfin [INN]

Common Name

English

Temoporfin [WHO-DD]

Common Name

English

Classification Tree Code System Code

WHO-ATC

L01XD05