Temoporfin: Difference between revisions

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			{{Short description\|Chemical compound}}
	{{drugbox
			{{Drugbox
	\| Verifiedfields = changed
		⚫	\| verifiedrevid = 448134770
⚫	\| UNII_Ref = {{fdacite\|~~changed~~\|FDA}}
		⚫	\| IUPAC_name = 3,3',3<nowiki>''</nowiki>,3<nowiki>'''</nowiki>-(2,3-dihydroporphyrin-5,10,15,20-tetrayl)tetraphenol
		⚫	\| image = Temoporfin.png

			<!--Clinical data-->
			\| tradename =
			\| Drugs.com = {{drugs.com\|international\|temoporfin}}
		⚫	\| licence_EU = yes
		⚫	\| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
		⚫	\| pregnancy_US = <!-- A / B / C / D / X -->
		⚫	\| pregnancy_category =
		⚫	\| legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled-->
		⚫	\| legal_CA = <!-- Schedule I, II, III, IV, V, VI, VII, VIII -->
		⚫	\| legal_UK = <!-- GSL, P, POM, CD, or Class A, B, C -->
		⚫	\| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V -->
		⚫	\| legal_status = Rx-only
		⚫	\| routes_of_administration =

			<!--Pharmacokinetic data-->
		⚫	\| bioavailability =
		⚫	\| protein_bound =
		⚫	\| metabolism =
		⚫	\| elimination_half-life =
		⚫	\| excretion =

			<!--Identifiers-->
			\| CAS_number_Ref = {{cascite\|correct\|??}}
		⚫	\| CAS_number = 122341-38-2
		⚫	\| ATC_prefix = L01
		⚫	\| ATC_suffix = XD05
		⚫	\| ATC_supplemental =
		⚫	\| PubChem = 60751
			\| DrugBank_Ref = {{drugbankcite\|correct\|drugbank}}
		⚫	\| DrugBank =
			\| ChEMBL = 383675
		⚫	\| UNII_Ref = {{fdacite\|correct\|FDA}}
	\| UNII = FU21S769PF		\| UNII = FU21S769PF
⚫	\| verifiedrevid = ~~408923375~~
⚫	\| IUPAC_name = 3,3',3<nowiki>''</nowiki>,3<nowiki>'''</nowiki>-(2,3-dihydroporphyrin-5,10,15,20-tetrayl)tetraphenol
⚫	\| image = Temoporfin.png
⚫	\| CAS_number = 122341-38-2
	\| CAS_supplemental =
⚫	\| ATC_prefix = L01
⚫	\| ATC_suffix = XD05
⚫	\| ATC_supplemental =
⚫	\| PubChem = 60751
⚫	\| DrugBank =
	\| KEGG_Ref = {{keggcite\|correct\|kegg}}		\| KEGG_Ref = {{keggcite\|correct\|kegg}}
	\| KEGG = D06066		\| KEGG = D06066
	\| ~~chemical_formula~~ =		\| ChemSpiderID = 54754

			<!--Chemical data-->
			\| chemical_formula =
	\| C=44 \| H=32 \| N=4 \| O=4		\| C=44 \| H=32 \| N=4 \| O=4
		⚫	\| 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
	\| molecular_weight = 680.74 g/mol
			\| StdInChI = 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-
⚫	\| smiles = C1CC2=NC1=C(C3=CC=C(N3)C(=C4C=CC(=N4)C(=C5C=CC(=C2C6=CC(=CC=C6)O)N5)C7=
			\| StdInChIKey = LYPFDBRUNKHDGX-LWQDQPMZSA-N
	CC(=CC=C7)O)C8=CC(=CC=C8)O)C9=CC(=CC=C9)O
⚫	\| bioavailability =
⚫	\| protein_bound =
⚫	\| metabolism =
⚫	\| elimination_half-life =
⚫	\| excretion =
⚫	\| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
⚫	\| pregnancy_US = <!-- A / B / C / D / X -->
⚫	\| pregnancy_category=
⚫	\| licence_EU = ~~Foscan~~
⚫	\| legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled-->
⚫	\| legal_CA = <!-- Schedule I, II, III, IV, V, VI, VII, VIII -->
⚫	\| legal_UK = <!-- GSL, P, POM, CD, or Class A, B, C -->
⚫	\| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V -->
⚫	\| legal_status = Rx-only
⚫	\| routes_of_administration =
	}}		}}

	'''Temoporfin''' (]) is a ] (based on ]) used in ] for the treatment of ] of the ]<ref name="pmid17516041">{{cite journal \|~~author~~=Lorenz KJ, Maier H \|title= \|language=~~German~~ \|journal=~~HNO~~ \|volume=56 \|issue=4 \|pages~~=402–9~~ ~~\|year~~=~~2008~~ \|~~month~~=April \|pmid=17516041 \|doi=10.1007/s00106-007-1573-1 ~~\|url=~~}}</ref>		'''Temoporfin''' (]) is a ] (based on ]) used in ] for the treatment of ] of the ]<ref name="pmid17516041">{{cite journal \| vauthors = Lorenz KJ, Maier H \| title = \| language = de \| journal = Hno \| volume = 56 \| issue = 4 \| pages = 402–409 \| date = April 2008 \| pmid = 17516041 \| doi = 10.1007/s00106-007-1573-1 }}</ref>
	.<ref name=~~OGB2009~~>{{cite ~~news~~ \|~~url~~=~~http://findarticles.com/p/articles/mi_qa3931/is_200909/ai_n42040200/pg_7/~~ \|title=Porphyrin and ~~Nonporphyrin~~ ~~Photosensitizers~~ in ~~Oncology~~: ~~Preclinical~~ and ~~Clinical~~ ~~Advances~~ in ~~Photodynamic~~ ~~Therapy.~~ Photochemistry and Photobiology, ~~Sep/Oct~~ ~~2009~~ \|~~author~~=~~O'Connor,~~ ~~Aisling~~ E, ~~Gallagher,~~ ~~William~~ M, ~~Byrne,~~ ~~Annette~~ T \| ~~work~~=~~Photochemistry~~ ~~and~~ ~~Photobiology~~ \|~~year~~=~~2009~~}}</ref>		.<ref name="O'Connor_2009">{{cite journal \| vauthors = O'Connor AE, Gallagher WM, Byrne AT \| title = Porphyrin and nonporphyrin photosensitizers in oncology: preclinical and clinical advances in photodynamic therapy \| journal = Photochemistry and Photobiology \| volume = 85 \| issue = 5 \| pages = 1053–1074 \| year = 2009 \| doi = 10.1111/j.1751-1097.2009.00585.x \| pmid = 19682322 \| s2cid = 205950773 \| doi-access = free }}</ref>
	It is marketed in the ] under the brand name '''Foscan'''. The ] ~~deemed~~ ~~Foscan~~ ~~non-approvable~~ in 2000. The EU approved its use in June 2001.<ref>http://www.highbeam.com/doc/1P2-18794532.html Foscan approval saves Scotia's skin.</ref>		It is marketed in the ] under the brand name '''Foscan'''. The U.S. ] (FDA) declined to approve Foscan in 2000. The EU approved its use in June 2001.<ref>{{cite web \| url = http://www.highbeam.com/doc/1P2-18794532.html \| work = HighBeam \| title = Foscan approval saves Scotia's skin. \| archive-url = https://web.archive.org/web/20121104175701/http://www.highbeam.com/doc/1P2-18794532.html \| archive-date = 2012-11-04 }}</ref>

			Good results were obtained in 21 of 35 patients treated in Germany.<ref>{{cite journal \| vauthors = Lorenz KJ, Maier H \| title = Photodynamic therapy with meta-tetrahydroxyphenylchlorin (Foscan) in the management of squamous cell carcinoma of the head and neck: experience with 35 patients \| journal = European Archives of Oto-Rhino-Laryngology \| volume = 266 \| issue = 12 \| pages = 1937–1944 \| date = December 2009 \| pmid = 19290535 \| doi = 10.1007/s00405-009-0947-2 \| s2cid = 5892034 }}</ref>
	Good results were obtained in 21 of 35 patients treated in Germany.<ref>http://www.springerlink.com/content/g74w224824v8l013/</ref>

			It is photoactivated at 652 nm<ref name="O'Connor_2009"/> i.e. by red light.
	It is photoactivated at 652 nm<ref>{{cite news\| url=http://findarticles.com/p/articles/mi_qa3931/is_200909/ai_n42040200/pg_7/ \| work=Photochemistry and Photobiology \| title=Porphyrin and Nonporphyrin Photosensitizers in Oncology: Preclinical and Clinical Advances in Photodynamic Therapy \| year=2009}}</ref> i.e. by red light.

	Patients can remain photosensitive for several weeks after treatment.<ref name=~~OGB2009~~/>		Patients can remain photosensitive for several weeks after treatment.<ref name="O'Connor_2009"/>

	==~~Further~~ ~~reading~~==		== References ==
			{{reflist\|30em}}
	*

			== Further reading ==
	==References==
	{{~~Reflist~~}}		{{refbegin}}
			* {{cite journal \| vauthors = Marchal S, François A, Dumas D, Guillemin F, Bezdetnaya L \| title = Relationship between subcellular localisation of Foscan and caspase activation in photosensitised MCF-7 cells \| journal = British Journal of Cancer \| volume = 96 \| issue = 6 \| pages = 944–51 \| date = March 2007 \| pmid = 17325708 \| pmc = 2360096 \| doi = 10.1038/sj.bjc.6603631 }}
			{{refend}}

	{{Chemotherapeutic agents}}		{{Chemotherapeutic agents}}
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	{{antineoplastic-drug-stub}}		{{antineoplastic-drug-stub}}

	]

Latest revision as of 10:42, 8 November 2023

Chemical compound Pharmaceutical compound

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
PubChem CID	60751
ChemSpider	54754
UNII	FU21S769PF
KEGG	D06066
ChEMBL	ChEMBL383675
CompTox Dashboard (EPA)	DTXSID7048619
ECHA InfoCard	100.152.970
Chemical and physical data
Formula	C₄₄H₃₂N₄O₄
Molar mass	680.764 g·mol
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)

Temoporfin (INN) 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. The U.S. Food and Drug Administration (FDA) declined to approve Foscan in 2000. The EU approved its use in June 2001.

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

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

Patients can remain photosensitive for several weeks after treatment.

References

Lorenz KJ, Maier H (April 2008). "". Hno (in German). 56 (4): 402–409. doi:10.1007/s00106-007-1573-1. PMID 17516041.
^ 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.

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 Rabacfosadine 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)

Topoisomerase inhibitors
(S phase)

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 (Losoxantrone Mitoxantrone Pixantrone) Amsacrine Bisantrene Crisnatol Menogaril

Crosslinking of DNA
(CCNS)

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)

Photosensitizers/PDT

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 (Fuzuloparib Niraparib +abiraterone acetate Olaparib Rucaparib) HDAC (Belinostat Entinostat Panobinostat Romidepsin Vorinostat) PIKI (Pi3K) (Alpelisib Copanlisib Duvelisib Idelalisib Inavolisib Umbralisib) IDH (Enasidenib Ivosidenib Olutasidenib Vorasidenib)
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 Eflornithine Elesclomol Elsamitrucin Epacadostat Eribulin Estramustine Glasdegib Idecabtagene vicleucel Imetelstat Lifileucel Lisocabtagene maraleucel Lonidamine Lucanthone Lurbinectedin Mitoguazone Mitotane Nadofaragene firadenovec Navitoclax Obecabtagene autoleucel Oblimersen Omacetaxine mepesuccinate Plitidepsin Tabelecleucel Retinoids (Alitretinoin Tretinoin) Selinexor Sitimagene ceradenovec Sotorasib Tagraxofusp Talimogene laherparepvec Tazemetostat Tebentafusp Tiazofurine Tigilanol tiglate Tisagenlecleucel Trabectedin Veliparib Venetoclax Verdinexor Vosaroxin

WHO-EM
Withdrawn from market
Clinical trials:
- Phase III
- Never to phase III

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Latest revision as of 10:42, 8 November 2023

References

Further reading