- Accession Number
Verteporfin, marketed as Visudyne, is a benzoporphyrin derivative. It is used as a photosensitizer in photodynamic therapy to eliminate abnormal blood vessels in wet form 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.
- Small Molecule
- Approved, Investigational
- Average: 718.7942
- Chemical Formula
- External IDs
- CL 318952
- FF 18
For 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.
- Associated Conditions
- Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.Learn More
Verteporfin, 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 action
Verteporfin 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.
- Not Available
- Volume of distribution
- Not Available
- Protein binding
- Not Available
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 elimination
Elimination is by the fecal route, with less than 0.01% of the dose recovered in urine.
Following 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%.
- Not Available
- Adverse Effects
Learn about our commercial Adverse Effects data.Learn More
Overdose 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
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Aminolevulinic acid Aminolevulinic acid may increase the photosensitizing activities of Verteporfin. Carprofen Carprofen may increase the photosensitizing activities of Verteporfin. Hexaminolevulinate Hexaminolevulinate may increase the photosensitizing activities of Verteporfin. Methoxsalen Methoxsalen may increase the photosensitizing activities of Verteporfin. Porfimer sodium Verteporfin may increase the photosensitizing activities of Porfimer sodium. Riboflavin Riboflavin may increase the photosensitizing activities of Verteporfin. Temoporfin Temoporfin may increase the photosensitizing activities of Verteporfin. Tiaprofenic acid Tiaprofenic acid may increase the photosensitizing activities of Verteporfin. Titanium dioxide Titanium dioxide may increase the photosensitizing activities of Verteporfin. Tretinoin The risk or severity of adverse effects can be increased when Tretinoin is combined with Verteporfin.Additional Data Available
- Extended DescriptionExtended Description
Extended description of the mechanism of action and particular properties of each drug interaction.Learn more
A severity rating for each drug interaction, from minor to major.Learn more
- Evidence LevelEvidence Level
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An effect category for each drug interaction. Know how this interaction affects the subject drug.Learn more
- Food Interactions
- No interactions found.
- International/Other Brands
- Visudine (Novartis)
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Visudyne Injection, powder, lyophilized, for solution 2 mg/1mL Intravenous Novartis 2000-04-14 2012-09-01 Visudyne Powder, for solution 15 mg Intravenous Cheplapharm Arzneimittel Gmbh 2000-06-26 Not applicable Visudyne Injection, powder, lyophilized, for solution 15 mg/1 Intravenous QLT Ophthalmics, Inc. 2000-04-12 Not applicable Visudyne Injection, powder, lyophilized, for solution 15 mg/1 Intravenous Valeant Pharmaceuticals North America LLC 2000-04-12 Not applicable
- ATC Codes
- S01LA01 — Verteporfin
- Drug Categories
- Antineovascularisation Agents
- Biological Factors
- EENT Drugs, Miscellaneous
- Heterocyclic Compounds, Fused-Ring
- Ocular Vascular Disorder Agents
- Photosensitizing Activity
- Photosensitizing Agents
- Pigments, Biological
- Radiation-Sensitizing Agents
- Sensory Organs
- Not classified
- CAS number
- InChI Key
- 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[220.127.116.11³,⁶.1⁸,¹¹.1¹³,¹⁶.0¹⁹,²⁴]octacosa-1,3,5,7,9,11(27),12,14,16,18(25),19,21-dodecaen-9-yl]propanoic acid
- General References
- 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]
- 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]
- AHFS Codes
- 52:92.00 — EENT Drugs, Miscellaneous
- FDA label
- Download (39.2 KB)
- Clinical Trials
Phase Status Purpose Conditions Count 4 Completed Treatment Age-Related Macular Degeneration (ARMD) 2 4 Completed Treatment Age-Related Macular Degeneration (ARMD) / Age-related Macular Degeneration; Polypoidal Choroidal Vasculopathy (PCV) / Polypoidal Choroidal Vasculopathy (PCV) / Polypoidal Choroidal Vasculopathy PCV 1 4 Completed Treatment Maculopathies, Age-Related / Subfoveal Choroidal Neovascularization 1 4 Completed Treatment Polypoidal Choroidal Vasculopathy (PCV) 1 4 Not Yet Recruiting Treatment Exudative Age Related Macular Degeneration / Neovascular Age-Related Macular Degeneration 1 4 Terminated Treatment Age-Related Macular Degeneration (ARMD) 1 3 Completed Treatment Age Related Macular Degeneration (ARMD) / Age-Related Macular Degeneration (ARMD) 1 3 Completed Treatment Age-Related Macular Degeneration (ARMD) / Subfoveal Choroidal Neovascularization 1 3 Completed Treatment Macular Degeneration 2 3 Completed Treatment Macular Degeneration / Subfoveal Choroidal Neovascularization 2
- Qlt inc
- Hollister-Stier Laboratories LLC
- JHP Pharmaceuticals LLC
- Novartis AG
- QLT Inc.
- Dosage Forms
Form Route Strength Injection, powder, lyophilized, for solution Intravenous 15 mg/1 Injection, powder, lyophilized, for solution Intravenous 2 mg/1mL Powder, for solution Intravenous 15 mg
Unit description Cost Unit Visudyne 15 mg vial 1702.64USD vialDrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patent Number Pediatric Extension Approved Expires (estimated) Region US5214036 No 1993-05-25 2010-05-25 CA2536069 No 2008-06-03 2014-03-14 CA1339927 No 1998-06-23 2015-06-23 US5756541 No 1998-05-26 2016-03-11 US5798349 No 1998-08-25 2015-08-25 US5707608 No 1998-01-13 2015-08-02Additional Data Available
- Filed OnFiled On
The date on which a patent was filed with the relevant government.Learn more
- Experimental Properties
Property Value Source logP 2.1 Not Available
- Predicted Properties
Property Value Source Water Solubility 0.0136 mg/mL ALOGPS logP 5.02 ALOGPS logP 6.34 ChemAxon logS -4.7 ALOGPS pKa (Strongest Acidic) 4.12 ChemAxon pKa (Strongest Basic) 4.78 ChemAxon Physiological Charge -1 ChemAxon Hydrogen Acceptor Count 7 ChemAxon Hydrogen Donor Count 3 ChemAxon Polar Surface Area 173.56 Å2 ChemAxon Rotatable Bond Count 12 ChemAxon Refractivity 199.08 m3·mol-1 ChemAxon Polarizability 81.29 Å3 ChemAxon Number of Rings 6 ChemAxon Bioavailability 0 ChemAxon Rule of Five No ChemAxon Ghose Filter No ChemAxon Veber's Rule No ChemAxon MDDR-like Rule Yes ChemAxon
- Predicted ADMET Features
Property Value Probability Human Intestinal Absorption - 0.5377 Blood Brain Barrier + 0.6313 Caco-2 permeable - 0.6425 P-glycoprotein substrate Substrate 0.7738 P-glycoprotein inhibitor I Non-inhibitor 0.577 P-glycoprotein inhibitor II Non-inhibitor 0.5444 Renal organic cation transporter Non-inhibitor 0.7681 CYP450 2C9 substrate Non-substrate 0.8178 CYP450 2D6 substrate Non-substrate 0.822 CYP450 3A4 substrate Substrate 0.6429 CYP450 1A2 substrate Inhibitor 0.7915 CYP450 2C9 inhibitor Inhibitor 0.7158 CYP450 2D6 inhibitor Non-inhibitor 0.754 CYP450 2C19 inhibitor Non-inhibitor 0.7057 CYP450 3A4 inhibitor Non-inhibitor 0.5157 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.652 Ames test Non AMES toxic 0.6596 Carcinogenicity Non-carcinogens 0.9368 Biodegradation Not ready biodegradable 1.0 Rat acute toxicity 2.6756 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9884 hERG inhibition (predictor II) Non-inhibitor 0.9038
- Mass Spec (NIST)
- Not Available
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Drug created on June 13, 2005 07:24 / Updated on August 09, 2020 06:16