Verteporfin

Identification

Summary

Verteporfin is a benzoporphyrin derivative used to treat pathological myopia, ocular histoplasmosis, and choroidal neovascularization in macular degeneration.

Brand Names
Visudyne
Generic Name
Verteporfin
DrugBank Accession Number
DB00460
Background

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.

Type
Small Molecule
Groups
Approved, Investigational
Structure
Weight
Average: 718.7942
Monoisotopic: 718.30026434
Chemical Formula
C41H42N4O8
Synonyms
  • Verteporfin
  • Verteporfina
  • Vertéporfine
  • Verteporfinum
External IDs
  • BPD
  • BPD-MA
  • CL 318952
  • FF 18

Pharmacology

Indication

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.

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Management ofSubfoveal choroidal neovascularization••••••••••••
Management ofSubfoveal choroidal neovascularization••• •••••
Management ofSubfoveal choroidal neovascularization••• •••••
Contraindications & Blackbox Warnings
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Pharmacodynamics

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.

Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not 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 elimination

Elimination is by the fecal route, with less than 0.01% of the dose recovered in urine.

Half-life

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%.

Clearance

Not Available

Adverse Effects
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Toxicity

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.

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

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.
DrugInteraction
Aminolevulinic acidAminolevulinic acid may increase the photosensitizing activities of Verteporfin.
CarprofenCarprofen may increase the photosensitizing activities of Verteporfin.
CelecoxibCelecoxib may increase the photosensitizing activities of Verteporfin.
ClofazimineClofazimine may increase the photosensitizing activities of Verteporfin.
CyproheptadineCyproheptadine may increase the photosensitizing activities of Verteporfin.
Food Interactions
No interactions found.

Products

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International/Other Brands
Visudine (Novartis)
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
VisudyneInjection, powder, lyophilized, for solution15 mg/1IntravenousBausch & Lomb Incorporated2000-04-12Not applicableUS flag
VisudyneInjection, powder, lyophilized, for solution2 mg/1mLIntravenousNovartis2000-04-142012-09-01US flag
VisudynePowder, for solution15 mg / vialIntravenousCheplapharm Arzneimittel Gmbh2000-06-26Not applicableCanada flag
VisudyneInjection, powder, lyophilized, for solution15 mg/1IntravenousQLT Ophthalmics, Inc.2000-04-12Not applicableUS flag
VisudyneInjection, powder, for solution15 mgIntravenousCheplapharm Arzneimittel Gmb H2020-12-16Not applicableEU flag

Categories

ATC Codes
S01LA01 — Verteporfin
Drug Categories
Classification
Not classified
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
WU713D62N9
CAS number
129497-78-5
InChI Key
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[16.6.1.1^{3,6}.1^{8,11}.1^{13,16}.0^{19,24}]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

References

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. [Article]
  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. [Article]
Human Metabolome Database
HMDB0014603
KEGG Drug
D01162
PubChem Compound
5362420
PubChem Substance
46506236
ChemSpider
4515032
RxNav
118886
ChEMBL
CHEMBL2052016
PharmGKB
PA451871
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Verteporfin
FDA label
Download (39.2 KB)

Clinical Trials

Clinical Trials

Pharmacoeconomics

Manufacturers
  • Qlt inc
Packagers
  • Hollister-Stier Laboratories LLC
  • JHP Pharmaceuticals LLC
  • Novartis AG
  • QLT Inc.
Dosage Forms
FormRouteStrength
Injection, powder, for solutionIntravenous15 mg/1vial
Injection, powder, lyophilized, for solutionIntravenous15 mg/1
Injection, powder, lyophilized, for solutionIntravenous2 mg/1mL
Powder, for solutionIntravenous15 mg / vial
Powder, for solutionIntravenous; Parenteral15 MG
InjectionIntravenous15 mg
Injection, powder, for solutionIntravenous15 mg
Injection, powder, for solutionIntravenous
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)Region
US5214036No1993-05-252010-05-25US flag
CA2536069No2008-06-032014-03-14Canada flag
CA1339927No1998-06-232015-06-23Canada flag
US5756541No1998-05-262016-03-11US flag
US5798349No1998-08-252015-08-25US flag
US5707608No1998-01-132015-08-02US flag

Properties

State
Solid
Experimental Properties
PropertyValueSource
logP2.1Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0136 mg/mLALOGPS
logP5.02ALOGPS
logP6.33Chemaxon
logS-4.7ALOGPS
pKa (Strongest Acidic)4.18Chemaxon
pKa (Strongest Basic)4.86Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count7Chemaxon
Hydrogen Donor Count3Chemaxon
Polar Surface Area173.56 Å2Chemaxon
Rotatable Bond Count12Chemaxon
Refractivity199.08 m3·mol-1Chemaxon
Polarizability81.21 Å3Chemaxon
Number of Rings6Chemaxon
Bioavailability0Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
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)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-0a4i-0000009100-05724e5635afe0a1d745
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-00p0-0000009200-6affa5a3446657279dfe
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-1000009000-2afa9c49c522197aa37b
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0zov-0000019100-54f9a91f936310e1a976
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-0000009000-fb6e8ff3045d0426a1fb
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-03di-0000039000-a0bcdf58f3205417c677
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0292-0000079100-251997920c0448b8592c
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-266.8122286
predicted
DarkChem Lite v0.1.0
[M-H]-260.11453
predicted
DeepCCS 1.0 (2019)
[M+H]+265.9565286
predicted
DarkChem Lite v0.1.0
[M+H]+262.2612
predicted
DeepCCS 1.0 (2019)
[M+Na]+266.9706286
predicted
DarkChem Lite v0.1.0
[M+Na]+268.45
predicted
DeepCCS 1.0 (2019)

Drug created at June 13, 2005 13:24 / Updated at March 18, 2024 16:48