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Identification
NamePorfimer
Accession NumberDB00707  (APRD00078)
TypeSmall Molecule
GroupsApproved, Investigational
DescriptionThe 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
Synonyms
Dihaematoporphyrin Ether
Dihematoporphyrin ether
Photofrin II
Porfimer natrium
Porfimer sodico
Porfimère sodique
Porfimerum natricum
External Identifiers Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Photofrininjection, powder, for solution75 mg/31.8mLintravenousPinnacle Biologics, Inc.1995-12-27Not applicableUs
Photofrinpowder for solution75 mgintravenousConcordia Laboratories Inc1995-12-31Not applicableCanada
Photofrinpowder for solution15 mgintravenousConcordia Laboratories Inc1995-12-312014-11-21Canada
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
PhotoBarrAxcan
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Porfimer sodium
ThumbNot applicableDBSALT000463
Categories
UNIIY3834SIK5F
CAS number87806-31-3
WeightAverage: 1179.385
Monoisotopic: 1178.547705235
Chemical FormulaC68H74N8O11
InChI KeyVAYJWFGRGMQINH-STKOUIOXSA-N
InChI
InChI=1S/C68H74N8O11/c1-29-41(13-17-61(79)80)53-28-56-44(16-20-64(85)86)32(4)48(72-56)24-59-68(36(8)52(76-59)25-58-65(37(9)77)33(5)49(73-58)21-45(29)69-53)40(12)87-39(11)67-35(7)50-22-46-30(2)42(14-18-62(81)82)54(70-46)27-55-43(15-19-63(83)84)31(3)47(71-55)23-57-66(38(10)78)34(6)51(74-57)26-60(67)75-50/h21-28,37-40,71-73,75,77-78H,13-20H2,1-12H3,(H,79,80)(H,81,82)(H,83,84)(H,85,86)/b45-21-,46-22-,47-23-,48-24-,49-21-,50-22-,51-26-,52-25-,53-28-,54-27-,55-27-,56-28-,57-23-,58-25-,59-24-,60-26-
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
CC(O)C1=C(C)/C2=C/C3=N/C(=C\C4=C(CCC(O)=O)C(C)=C(N4)/C=C4\N=C(\C=C\1/N\2)C(C)=C4C(C)OC(C)C1=C2NC(\C=C4/N=C(/C=C5\N\C(=C/C6=N/C(=C\2)/C(C)=C6C(C)O)C(C)=C5CCC(O)=O)C(CCC(O)=O)=C4C)=C1C)/C(CCC(O)=O)=C3C
Taxonomy
ClassificationNot classified
Pharmacology
IndicationIndicated in the treatment of esophageal cancer.
PharmacodynamicsPorfimer 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 actionCellular 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.
Related Articles
AbsorptionNot 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%
MetabolismNot Available
Route of eliminationNot Available
Half life10-452 hours
Clearance
  • Renal cl=199.7 +/-  56.9 mL/min [Healthy subjects receiving a single 300-mg oral dose]
ToxicityNot Available
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal AbsorptionNot AvailableNot Available
Blood Brain BarrierNot AvailableNot Available
Caco-2 permeableNot AvailableNot Available
P-glycoprotein substrateNot AvailableNot Available
P-glycoprotein inhibitor INot AvailableNot Available
P-glycoprotein inhibitor IINot AvailableNot Available
Renal organic cation transporterNot AvailableNot Available
CYP450 2C9 substrateNot AvailableNot Available
CYP450 2D6 substrateNot AvailableNot Available
CYP450 3A4 substrateNot AvailableNot Available
CYP450 1A2 substrateNot AvailableNot Available
CYP450 2C9 inhibitorNot AvailableNot Available
CYP450 2D6 inhibitorNot AvailableNot Available
CYP450 2C19 inhibitorNot AvailableNot Available
CYP450 3A4 inhibitorNot AvailableNot Available
CYP450 inhibitory promiscuityNot AvailableNot Available
Ames testNot AvailableNot Available
CarcinogenicityNot AvailableNot Available
BiodegradationNot AvailableNot Available
Rat acute toxicityNot AvailableNot applicable
hERG inhibition (predictor I)Not AvailableNot Available
hERG inhibition (predictor II)Not AvailableNot Available
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
Manufacturers
  • Axcan pharma us inc
Packagers
Dosage forms
FormRouteStrength
Injection, powder, for solutionintravenous75 mg/31.8mL
Powder for solutionintravenous15 mg
Powder for solutionintravenous75 mg
Prices
Unit descriptionCostUnit
Photofrin 75 mg vial3317.04USD vial
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
CA2094974 No1996-10-222013-04-27Canada
US5145863 No1992-12-152009-12-15Us
US5438071 No1995-08-012012-08-01Us
Properties
StateSolid
Experimental Properties
PropertyValueSource
logP2.8Not Available
Predicted Properties
PropertyValueSource
logP5.55ChemAxon
Hydrogen Acceptor Count21ChemAxon
Hydrogen Donor Count11ChemAxon
Polar Surface Area379.65 Å2ChemAxon
Rotatable Bond Count25ChemAxon
Refractivity496.6 m3·mol-1ChemAxon
Polarizability199.95 Å3ChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesL01XD01
AHFS Codes
  • 10:00.00
PDB Entries
FDA labelDownload (321 KB)
MSDSNot Available
Interactions
Drug Interactions
Drug
ACETOPHENONEACETOPHENONE may increase the photosensitizing activities of Porfimer.
AcetyldigitoxinAcetyldigitoxin may decrease the cardiotoxic activities of Porfimer.
Aminolevulinic acidAminolevulinic acid may increase the photosensitizing activities of Porfimer.
BenzophenoneBenzophenone may increase the photosensitizing activities of Porfimer.
BevacizumabBevacizumab may increase the cardiotoxic activities of Porfimer.
CabazitaxelThe risk or severity of adverse effects can be increased when Cabazitaxel is combined with Porfimer.
CarprofenCarprofen may increase the photosensitizing activities of Porfimer.
CyamemazineCyamemazine may increase the photosensitizing activities of Porfimer.
CyclophosphamideCyclophosphamide may increase the cardiotoxic activities of Porfimer.
DeslanosideDeslanoside may decrease the cardiotoxic activities of Porfimer.
DigitoxinDigitoxin may decrease the cardiotoxic activities of Porfimer.
DigoxinDigoxin may decrease the cardiotoxic activities of Porfimer.
DocetaxelThe risk or severity of adverse effects can be increased when Docetaxel is combined with Porfimer.
HexaminolevulinateHexaminolevulinate may increase the photosensitizing activities of Porfimer.
MethoxsalenMethoxsalen may increase the photosensitizing activities of Porfimer.
motexafin gadoliniummotexafin gadolinium may increase the photosensitizing activities of Porfimer.
Motexafin lutetiumMotexafin lutetium may increase the photosensitizing activities of Porfimer.
OuabainOuabain may decrease the cardiotoxic activities of Porfimer.
PaclitaxelThe risk or severity of adverse effects can be increased when Paclitaxel is combined with Porfimer.
Protoporphyrin IxProtoporphyrin Ix may increase the photosensitizing activities of Porfimer.
RiboflavinRiboflavin may increase the photosensitizing activities of Porfimer.
rostaporfinrostaporfin may increase the photosensitizing activities of Porfimer.
Tiaprofenic acidTiaprofenic acid may increase the photosensitizing activities of Porfimer.
Titanium dioxideTitanium dioxide may increase the photosensitizing activities of Porfimer.
TrastuzumabTrastuzumab may increase the cardiotoxic activities of Porfimer.
TrioxsalenTrioxsalen may increase the photosensitizing activities of Porfimer.
VerteporfinVerteporfin may increase the photosensitizing activities of Porfimer.
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
other/unknown
General Function:
Virus receptor activity
Specific Function:
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.(Microbial infection) Acts as a receptor for hepatitis C virus in hepatocytes, but not through a direct interaction with viral proteins (PubMed:10535997, PubMed:12615904). Acts as a r...
Gene Name:
LDLR
Uniprot ID:
P01130
Molecular Weight:
95375.105 Da
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:1531856 ]
  2. Tsukagoshi S: [Porfimer sodium (Photofrin-II)]. Gan To Kagaku Ryoho. 1995 Aug;22(9):1271-8. [PubMed:7661580 ]
  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:7994588 ]
  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:2945739 ]
  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:1450993 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
antagonist
General Function:
Receptor signaling protein activity
Specific Function:
High affinity receptor for the Fc region of immunoglobulins gamma. Functions in both innate and adaptive immune responses.
Gene Name:
FCGR1A
Uniprot ID:
P12314
Molecular Weight:
42631.525 Da
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:2544592 ]
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23