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Identification
Name Porfimer
Accession Number DB00707 (APRD00078)
Type small molecule
Groups approved
Description

The purified component of hematoporphyrin derivative, it consists of a mixture of oligomeric porphyrins. It is used in photodynamic therapy (hematoporphyrin photoradiation); to treat malignant lesions with visible light and experimentally as an antiviral agent. It is the first drug to be approved in the use of photodynamic therapy in the United States. [PubChem]
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  • DHP ether
  • Dihematoporphyrin ether
  • Porfimer sodium
Synonyms
DHP ether
Dihematoporphyrin ether
Porfimer sodium
Salts Not Available
Brand names
Name Company
Photofrin
Brand mixtures Not Available
Categories
  • Antineoplastic Agents
  • Antiviral Agents
  • Dermatologic Agents
  • Photosensitizing Agents
CAS number 87806-31-3
Weight Average: 1676.0053
Monoisotopic: 1674.831531666
Chemical Formula C99H110N12O13
InChI Key InChIKey=NYQGMKORVNYSLZ-DZGUDHBZSA-N
InChI
InChI=1S/C99H110N12O13/c1-43-46(4)70-37-88-97(55(13)79(109-88)34-76-51(9)63(21-27-93(116)117)84(106-76)40-82-61(19-25-91(112)113)49(7)73(103-82)31-67(43)100-70)58(16)123-59(17)98-56(14)80-35-77-53(11)65(23-29-95(120)121)86(108-77)42-87-66(54(12)75(105-87)33-69-44(2)47(5)71(101-69)38-89(98)110-80)24-30-96(122)124-60(18)99-57(15)81-36-78-52(10)64(22-28-94(118)119)85(107-78)41-83-62(20-26-92(114)115)50(8)74(104-83)32-68-45(3)48(6)72(102-68)39-90(99)111-81/h31-36,40-42,58-60,70-72,103-105,109-111H,19-30,37-39H2,1-18H3,(H,112,113)(H,114,115)(H,116,117)(H,118,119)(H,120,121)/b73-31-,74-32-,75-33-,76-34-,77-35-,78-36-,82-40-,83-41-,87-42-
Plain Text
IUPAC Name
3-{14-[1-({3-[14-(1-{1-[10,14-bis(2-carboxyethyl)-5,9,15,19,20-pentamethyl-21,22,23,24-tetraazapentacyclo[16.2.1.1^{3,6}.1^{8,11}.1^{13,16}]tetracosa-3,5,7,9,11(23),12,14,16,18(21),19-decaen-4-yl]ethoxy}ethyl)-20-(2-carboxyethyl)-5,9,10,15,19-pentamethyl-21,22,23,24-tetraazapentacyclo[16.2.1.1^{3,6}.1^{8,11}.1^{13,16}]tetracosa-1(21),2,4,6,8(23),9,13,15,17,19-decaen-4-yl]propanoyl}oxy)ethyl]-20-(2-carboxyethyl)-5,9,10,15,19-pentamethyl-21,22,23,24-tetraazapentacyclo[16.2.1.1^{3,6}.1^{8,11}.1^{13,16}]tetracosa-1(21),2,4,6,8(23),9,13,15,17,19-decaen-4-yl}propanoic acid
SMILES
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Not Available
Classes Not Available
Substructures Not Available
Pharmacology
Indication Indicated in the treatment of esophageal cancer.
Pharmacodynamics Porfimer is a photosensitizing agent used in the photodynamic therapy (PDT) of tumors. Porfimer is indicated for the palliation of patients with completely obstructing esophageal cancer, or of patients with partially obstructing esophageal cancer who cannot be satisfactorily treated with Nd:YAG laser therapy, reduction of obstruction and palliation of symptoms in patients with completely or partially obstructing endobronchial nonsmall cell lung cancer (NSCLC), and the treatment of microinvasive endobronchial NSCLC in patients for whom surgery and radiotherapy are not indicated. The cytotoxic and antitumor actions of porfimer are light and oxygen dependent. Tumor selectivity in treatment occurs through a combination of selective retention of porfimer and selective delivery of light.
Mechanism of action Cellular damage caused by porfimer is a consequence of the propagation of radical reactions. Radical initiation may occur after porfimer absorbs light to form a porphyrin excited state. Spin transfer from porfimer to molecular oxygen may then generate singlet oxygen. Subsequent radical reactions can form superoxide and hydroxyl radicals. Tumor death also occurs through ischemic necrosis secondary to vascular occlusion that appears to be partly mediated by thromboxane A2 release.
Absorption Not Available
Volume of distribution
  • 0.49 ± 0.28 L/kg [2 mg/kg dose of porfimer sodium to 4 male cancer patients]
Protein binding ~90%
Metabolism Not Available
Route of elimination Not Available
Half life 10-452 hours
Clearance
  • Renal cl=199.7 +/-  56.9 mL/min [Healthy subjects receiving a single 300-mg oral dose]
Toxicity Not Available
Affected organisms
  • Humans and other mammals
Pathways Not Available
Pharmacoeconomics
Manufacturers
  • Axcan pharma us inc
Packagers
Dosage forms
Form Route Strength
Powder, for solution Intravenous
Prices
Unit description Cost Unit
Photofrin 75 mg vial 3317.04 USD vial
Patents
Country Patent Number Approved Expires (estimated)
United States 5438071 1995-08-01 2012-08-01
United States 5145863 1992-12-15 2009-12-15
Canada 2094974 1996-10-22 2013-04-27
Properties
State solid
Melting point Not Available
Experimental Properties
Property Value Source
logP 2.8 PhysProp
Predicted Properties
Property Value Source
water solubility ALOGPS
logP 0 ALOGPS
logP 5.55 ChemAxon Molconvert
logS 0 ALOGPS
pKa 3.44 ChemAxon Molconvert
hydrogen acceptor count 21 ChemAxon Molconvert
hydrogen donor count 11 ChemAxon Molconvert
polar surface area 379.65 ChemAxon Molconvert
rotatable bond count 25 ChemAxon Molconvert
refractivity 496.6 ChemAxon Molconvert
polarizability 199.95 ChemAxon Molconvert
References
Synthesis Reference Not Available
General Reference Not Available
External Links
Resource Link
ChEBI 60652 Link_out
ChEMBL 60652 Link_out
PharmGKB PA10327 Link_out
Drug Product Database 2019876 Link_out
RxList http://www.rxlist.com/cgi/generic3/photofrin.htm Link_out
Drugs.com http://www.drugs.com/cdi/porfimer.html Link_out
Wikipedia http://en.wikipedia.org/wiki/Porfimer Link_out
ATC Codes
  • L01XD01
AHFS Codes
  • 10:00.00
PDB Entries
FDA label show (321 KB)
MSDS Not Available
Interactions
Drug Interactions Not Available
Food Interactions Not Available
Targets

1. Low-density lipoprotein receptor

Pharmacological action: unknown
Actions: other/unknown

Binds LDL, the major cholesterol-carrying lipoprotein of plasma, and transports it into cells by endocytosis. In order to be internalized, the receptor-ligand complexes must first cluster into clathrin-coated pits

Organism class: human
UniProt ID: P01130 Link_out
Gene: LDLR Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Korbelik M: Low density lipoprotein receptor pathway in the delivery of Photofrin: how much is it relevant for selective accumulation of the photosensitizer in tumors? J Photochem Photobiol B. 1992 Jan;12(1):107-9. Pubmed
  2. Tsukagoshi S: [Porfimer sodium (Photofrin-II)] Gan To Kagaku Ryoho. 1995 Aug;22(9):1271-8. Pubmed
  3. Maziere JC, Mora L, Biade S, Maziere C, Santus R: [Potentiation of the photocytotoxic effect of photofrin II: synergistic action of verapamil and lovastatin] Bull Acad Natl Med. 1994 Jun;178(6):1177-88; discussion 1188-9. Pubmed
  4. Candide C, Morliere P, Maziere JC, Goldstein S, Santus R, Dubertret L, Reyftmann JP, Polonovski J: In vitro interaction of the photoactive anticancer porphyrin derivative photofrin II with low density lipoprotein, and its delivery to cultured human fibroblasts. FEBS Lett. 1986 Oct 20;207(1):133-8. Pubmed
  5. Maziere JC, Morliere P, Biade S, Santus R: [Antitumor photochemotherapy: biochemical bases, therapeutic uses and perspectives] C R Seances Soc Biol Fil. 1992;186(1-2):88-106. Pubmed

2. High affinity immunoglobulin gamma Fc receptor I

Pharmacological action: unknown
Actions: antagonist

Binds to the Fc region of immunoglobulins gamma. High affinity receptor

Organism class: human
UniProt ID: P12314 Link_out
Gene: FCGR1A Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Krutmann J, Athar M, Mendel DB, Khan IU, Guyre PM, Mukhtar H, Elmets CA: Inhibition of the high affinity Fc receptor (Fc gamma RI) on human monocytes by porphyrin photosensitization is highly specific and mediated by the generation of superoxide radicals. J Biol Chem. 1989 Jul 5;264(19):11407-13. Pubmed
Comments
Drug created on June 13, 2005 07:24 / Updated on April 19, 2012 13:14