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Identification
NameVerteporfin
Accession NumberDB00460  (APRD01290)
TypeSmall Molecule
GroupsApproved, Investigational
Description

Verteporfin, otherwise known as benzoporphyrin derivative (trade name Visudyne®), is a medication used as a photosensitizer for photodynamic therapy to eliminate the abnormal blood vessels in the eye associated with conditions such as the wet form of macular degeneration. Verteporfin accumulates in these abnormal blood vessels and, when stimulated by nonthermal red light with a wavelength of 693 nm in the presence of oxygen, produces highly reactive short-lived singlet oxygen and other reactive oxygen radicals, resulting in local damage to the endothelium and blockage of the vessels.

Structure
Thumb
Synonyms
Verteporfin
Verteporfina
Vertéporfine
Verteporfinum
External Identifiers
  • BPD
  • BPD-MA
  • CL 318952
  • FF 18
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Visudyneinjection, powder, lyophilized, for solution15 mg/1intravenousValeant Pharmaceuticals North America LLC2000-04-12Not applicableUs
Visudynepowder for solution15 mgintravenousValeant Canada Lp Valeant Canada S.E.C.2000-06-26Not applicableCanada
Visudyneinjection, powder, lyophilized, for solution15 mg/1intravenousQLT Ophthalmics, Inc.2000-04-12Not applicableUs
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
VisudineNovartis
Brand mixturesNot Available
SaltsNot Available
Categories
UNII0X9PA28K43
CAS number129497-78-5
WeightAverage: 718.7942
Monoisotopic: 718.30026434
Chemical FormulaC41H42N4O8
InChI KeyInChIKey=YTZALCGQUPRCGW-MXVXOLGGSA-N
InChI
InChI=1S/C41H42N4O8/c1-9-23-20(2)29-17-34-27-13-10-26(39(49)52-7)38(40(50)53-8)41(27,5)35(45-34)19-30-22(4)25(12-15-37(48)51-6)33(44-30)18-32-24(11-14-36(46)47)21(3)28(43-32)16-31(23)42-29/h9-10,13,16-19,38,42,44H,1,11-12,14-15H2,2-8H3,(H,46,47)/b28-16-,29-17-,30-19-,31-16-,32-18-,33-18-,34-17-,35-19-/t38-,41+/m0/s1
IUPAC Name
3-[(23S,24R)-14-ethenyl-5-(3-methoxy-3-oxopropyl)-22,23-bis(methoxycarbonyl)-4,10,15,24-tetramethyl-25,26,27,28-tetraazahexacyclo[16.6.1.1³,⁶.1⁸,¹¹.1¹³,¹⁶.0¹⁹,²⁴]octacosa-1,3,5,7,9,11(27),12,14,16,18(25),19,21-dodecaen-9-yl]propanoic acid
SMILES
COC(=O)CCC1=C2NC(\C=C3/N=C(/C=C4\N\C(=C/C5=N/C(=C\2)/C(CCC(O)=O)=C5C)C(C=C)=C4C)C2=CC=C([C@@H](C(=O)OC)[C@@]32C)C(=O)OC)=C1C
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as tetrapyrroles and derivatives. These are polycyclic aromatic compounds containing four pyrrole rings joined by one-carbon units linking position 2 of one pyrrole ring to position 5 of the next.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassTetrapyrroles and derivatives
Sub ClassNot Available
Direct ParentTetrapyrroles and derivatives
Alternative Parents
Substituents
  • Tetrapyrrole skeleton
  • Tetracarboxylic acid or derivatives
  • Isoindole or derivatives
  • Fatty acid ester
  • Fatty acyl
  • Substituted pyrrole
  • Heteroaromatic compound
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Methyl ester
  • Pyrrole
  • Carboxylic acid ester
  • Azacycle
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationFor the treatment of patients with predominantly classic subfoveal choroidal neovascularization due to age-related macular degeneration, pathologic myopia or presumed ocular histoplasmosis syndrome. Verteporfin can also be used to destroy tumors.
PharmacodynamicsVerteporfin, otherwise known as benzoporphyrin derivative, is a medication used in conjunction with laser treatment to eliminate the abnormal blood vessels in the eye associated with conditions such as the wet form of macular degeneration. Verteporfin accumulates in these abnormal blood vessels and, when stimulated by nonthermal red light with a wavelength of 693 nm in the presence of oxygen, produces highly reactive short-lived singlet oxygen and other reactive oxygen radicals, resulting in local damage to the endothelium and blockage of the vessels.
Mechanism of actionVerteporfin is transported in the plasma primarily by lipoproteins. Once verteporfin is activated by light in the presence of oxygen, highly reactive, short-lived singlet oxygen and reactive oxygen radicals are generated. Light activation of verteporfin results in local damage to neovascular endothelium, resulting in vessel occlusion. Damaged endothelium is known to release procoagulant and vasoactive factors through the lipo-oxygenase (leukotriene) and cyclo-oxygenase (eicosanoids such as thromboxane) pathways, resulting in platelet aggregation, fibrin clot formation and vasoconstriction. Verteporfin appears to somewhat preferentially accumulate in neovasculature, including choroidal neovasculature. However, animal models indicate that the drug is also present in the retina. As singlet oxygen and reactive oxygen radicals are cytotoxic, Verteporfin can also be used to destroy tumor cells.
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism

Metabolized to a small extent to its diacid metabolite by liver and plasma esterases. NADPH-dependent liver enzyme systems (including the cytochrome P450 isozymes) do not appear to play a role in the metabolism of verteporfin.

Route of eliminationElimination is by the fecal route, with less than 0.01% of the dose recovered in urine.
Half lifeFollowing intravenous infusion, verteporfin exhibits a bi-exponential elimination with a terminal elimination half-life of approximately 5-6 hours. Mild hepatic insufficiency increases half-life by approximately 20%.
ClearanceNot Available
ToxicityOverdose of drug and/or light in the treated eye may result in nonperfusion of normal retinal vessels with the possibility of severe decrease in vision that could be permanent. An overdose of drug will also result in the prolongation of the period during which the patient remains photosensitive to bright light.
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 Absorption-0.5377
Blood Brain Barrier+0.6313
Caco-2 permeable-0.6425
P-glycoprotein substrateSubstrate0.7738
P-glycoprotein inhibitor INon-inhibitor0.577
P-glycoprotein inhibitor IINon-inhibitor0.5444
Renal organic cation transporterNon-inhibitor0.7681
CYP450 2C9 substrateNon-substrate0.8178
CYP450 2D6 substrateNon-substrate0.822
CYP450 3A4 substrateSubstrate0.6429
CYP450 1A2 substrateInhibitor0.7915
CYP450 2C9 inhibitorInhibitor0.7158
CYP450 2D6 inhibitorNon-inhibitor0.754
CYP450 2C19 inhibitorNon-inhibitor0.7057
CYP450 3A4 inhibitorNon-inhibitor0.5157
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.652
Ames testNon AMES toxic0.6596
CarcinogenicityNon-carcinogens0.9368
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.6756 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9884
hERG inhibition (predictor II)Non-inhibitor0.9038
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
Manufacturers
  • Qlt inc
Packagers
Dosage forms
FormRouteStrength
Injection, powder, lyophilized, for solutionintravenous15 mg/1
Powder for solutionintravenous15 mg
Prices
Unit descriptionCostUnit
Visudyne 15 mg vial1702.64USD vial
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
CA1339927 No1998-06-232015-06-23Canada
CA2536069 No2008-06-032014-03-14Canada
US5214036 No1993-05-252010-05-25Us
US5707608 No1995-08-022015-08-02Us
US5756541 No1996-03-112016-03-11Us
US5798349 No1995-08-252015-08-25Us
Properties
StateSolid
Experimental Properties
PropertyValueSource
logP2.1Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0136 mg/mLALOGPS
logP5.02ALOGPS
logP6.34ChemAxon
logS-4.7ALOGPS
pKa (Strongest Acidic)4.12ChemAxon
pKa (Strongest Basic)4.78ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area173.56 Å2ChemAxon
Rotatable Bond Count12ChemAxon
Refractivity199.08 m3·mol-1ChemAxon
Polarizability81.29 Å3ChemAxon
Number of Rings6ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis ReferenceNot Available
General References
  1. Chan WM, Lim TH, Pece A, Silva R, Yoshimura N: Verteporfin PDT for non-standard indications--a review of current literature. Graefes Arch Clin Exp Ophthalmol. 2010 May;248(5):613-26. doi: 10.1007/s00417-010-1307-z. Epub 2010 Feb 17. [PubMed:20162298 ]
  2. Nowak-Sliwinska P, Karocki A, Elas M, Pawlak A, Stochel G, Urbanska K: Verteporfin, photofrin II, and merocyanine 540 as PDT photosensitizers against melanoma cells. Biochem Biophys Res Commun. 2006 Oct 20;349(2):549-55. Epub 2006 Aug 22. [PubMed:16945338 ]
External Links
ATC CodesS01LA01
AHFS Codes
  • 52:92.00
PDB EntriesNot Available
FDA labelDownload (39.2 KB)
MSDSNot Available
Interactions
Drug Interactions
Drug
AcitretinAcitretin may increase the photosensitizing activities of Verteporfin.
AdapaleneAdapalene may increase the photosensitizing activities of Verteporfin.
AfatinibAfatinib may increase the photosensitizing activities of Verteporfin.
AlitretinoinAlitretinoin may increase the photosensitizing activities of Verteporfin.
Aminolevulinic acidAminolevulinic acid may increase the photosensitizing activities of Verteporfin.
AmiodaroneAmiodarone may increase the photosensitizing activities of Verteporfin.
BenzophenoneBenzophenone may increase the photosensitizing activities of Verteporfin.
BexaroteneBexarotene may increase the photosensitizing activities of Verteporfin.
BicalutamideBicalutamide may increase the photosensitizing activities of Verteporfin.
CarprofenCarprofen may increase the photosensitizing activities of Verteporfin.
CelecoxibCelecoxib may increase the photosensitizing activities of Verteporfin.
ChlorothiazideChlorothiazide may increase the photosensitizing activities of Verteporfin.
ChlorpromazineChlorpromazine may increase the photosensitizing activities of Verteporfin.
ChlorpropamideChlorpropamide may increase the photosensitizing activities of Verteporfin.
ChlorthalidoneChlorthalidone may increase the photosensitizing activities of Verteporfin.
CiprofloxacinCiprofloxacin may increase the photosensitizing activities of Verteporfin.
CobimetinibCobimetinib may increase the photosensitizing activities of Verteporfin.
DemeclocyclineDemeclocycline may increase the photosensitizing activities of Verteporfin.
DiclofenacDiclofenac may increase the photosensitizing activities of Verteporfin.
DiflunisalDiflunisal may increase the photosensitizing activities of Verteporfin.
DoxycyclineDoxycycline may increase the photosensitizing activities of Verteporfin.
EtodolacEtodolac may increase the photosensitizing activities of Verteporfin.
FenoprofenFenoprofen may increase the photosensitizing activities of Verteporfin.
FloctafenineFloctafenine may increase the photosensitizing activities of Verteporfin.
FluphenazineFluphenazine may increase the photosensitizing activities of Verteporfin.
FlurbiprofenFlurbiprofen may increase the photosensitizing activities of Verteporfin.
GemifloxacinGemifloxacin may increase the photosensitizing activities of Verteporfin.
GliclazideGliclazide may increase the photosensitizing activities of Verteporfin.
GlimepirideGlimepiride may increase the photosensitizing activities of Verteporfin.
GlipizideGlipizide may increase the photosensitizing activities of Verteporfin.
GlyburideGlyburide may increase the photosensitizing activities of Verteporfin.
GriseofulvinGriseofulvin may increase the photosensitizing activities of Verteporfin.
HydrochlorothiazideHydrochlorothiazide may increase the photosensitizing activities of Verteporfin.
IbuprofenIbuprofen may increase the photosensitizing activities of Verteporfin.
IndapamideIndapamide may increase the photosensitizing activities of Verteporfin.
IndomethacinIndomethacin may increase the photosensitizing activities of Verteporfin.
IsotretinoinIsotretinoin may increase the photosensitizing activities of Verteporfin.
KetoprofenKetoprofen may increase the photosensitizing activities of Verteporfin.
KetorolacKetorolac may increase the photosensitizing activities of Verteporfin.
LevofloxacinLevofloxacin may increase the photosensitizing activities of Verteporfin.
Mefenamic acidMefenamic acid may increase the photosensitizing activities of Verteporfin.
MeloxicamMeloxicam may increase the photosensitizing activities of Verteporfin.
MethotrimeprazineMethotrimeprazine may increase the photosensitizing activities of Verteporfin.
MethoxsalenMethoxsalen may increase the photosensitizing activities of Verteporfin.
MethyclothiazideMethyclothiazide may increase the photosensitizing activities of Verteporfin.
MetolazoneMetolazone may increase the photosensitizing activities of Verteporfin.
MinocyclineMinocycline may increase the photosensitizing activities of Verteporfin.
MoxifloxacinMoxifloxacin may increase the photosensitizing activities of Verteporfin.
NabumetoneNabumetone may increase the photosensitizing activities of Verteporfin.
NaproxenNaproxen may increase the photosensitizing activities of Verteporfin.
NorfloxacinNorfloxacin may increase the photosensitizing activities of Verteporfin.
OfloxacinOfloxacin may increase the photosensitizing activities of Verteporfin.
OxaprozinOxaprozin may increase the photosensitizing activities of Verteporfin.
PanitumumabPanitumumab may increase the photosensitizing activities of Verteporfin.
PerphenazinePerphenazine may increase the photosensitizing activities of Verteporfin.
PipotiazinePipotiazine may increase the photosensitizing activities of Verteporfin.
PiroxicamPiroxicam may increase the photosensitizing activities of Verteporfin.
PorfimerPorfimer may increase the photosensitizing activities of Verteporfin.
ProchlorperazineProchlorperazine may increase the photosensitizing activities of Verteporfin.
PromazinePromazine may increase the photosensitizing activities of Verteporfin.
RiboflavinRiboflavin may increase the photosensitizing activities of Verteporfin.
rostaporfinrostaporfin may increase the photosensitizing activities of Verteporfin.
SimeprevirSimeprevir may increase the photosensitizing activities of Verteporfin.
SulfadiazineSulfadiazine may increase the photosensitizing activities of Verteporfin.
SulindacSulindac may increase the photosensitizing activities of Verteporfin.
TetracyclineTetracycline may increase the photosensitizing activities of Verteporfin.
ThioridazineThioridazine may increase the photosensitizing activities of Verteporfin.
Tiaprofenic acidTiaprofenic acid may increase the photosensitizing activities of Verteporfin.
TolazamideTolazamide may increase the photosensitizing activities of Verteporfin.
TolbutamideTolbutamide may increase the photosensitizing activities of Verteporfin.
TolmetinTolmetin may increase the photosensitizing activities of Verteporfin.
TretinoinTretinoin may increase the photosensitizing activities of Verteporfin.
TrifluoperazineTrifluoperazine may increase the photosensitizing activities of Verteporfin.
TrioxsalenTrioxsalen may increase the photosensitizing activities of Verteporfin.
VemurafenibVemurafenib may increase the photosensitizing activities of Verteporfin.
VoriconazoleVoriconazole may increase the photosensitizing activities of Verteporfin.
Food InteractionsNot Available
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Drug created on June 13, 2005 07:24 / Updated on July 01, 2016 01:51