Verteporfin

 Verteporfin (trade name Visudyne), a benzoporphyrin derivative, 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 689 nm[1] 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.[2][3]

Verteporfin
Verteporfin.svg
Clinical data
Trade namesVisudyne
AHFS/Drugs.comMonograph
MedlinePlusa607060
License data
  • EU EMAby INN
Routes of
administration
Intravenous
ATC code
  • S01LA01 (WHO)
Legal status
Legal status
  • US: ℞-only
Identifiers
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
CAS Number
  • 129497-78-5 check
PubChem CID
  • 5362420
DrugBank
  • DB00460 check
ChemSpider
  • 21106402 check
UNII
  • 0X9PA28K43
KEGG
  • D01162 check
ChEBI
  • CHEBI:60775 check
ChEMBL
  • ChEMBL2218885 ☒
CompTox Dashboard (EPA)
  • DTXSID2045604 Edit this at Wikidata
Chemical and physical data
FormulaC41H42N4O8
Molar mass718.807 g·mol−1
3D model (JSmol)
  • Interactive image
SMILES
  • COC(=O)CCC=1C(C)=C2C=C6N=C(C=C4NC(=CC3=NC(=CC=1N2)C(CCC(O)=O)=C3C)C(C=C)=C4C)C5=CC=C(C(=O)OC)[C@@H](C(=O)OC)[C@]56C
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/h9-10,13,16-19,38,43,45H,1,11-12,14-15H2,2-8H3,(H,46,47)/b31-16-,33-18-,34-17-,35-19-/t38-,41+/m0/s1 check
  • Key:ZCQHFRFEJXRZDF-YWANUUMDSA-N check
 ☒check (what is this?)  (verify)

Verteporfin is also used off-label for the treatment of central serous retinopathy.[4]

AdministrationEdit

Verteporfin is usually injected intravenously into the largest arm vein.[5] It is injected at a dose of 6 mg/m2 and light-activated.[5] It is usually is given 15 minutes before laser treatment.[2] This dose can be repeated 4 times per year.[5]

ContraindicationsEdit

Porphyria.[2]

Side effectsEdit

Most common side effects are blurred vision, headache, and local effects at the injection site. Also, photosensitivity; it is strictly advised to avoid exposure to sunlight and unscreened lighting until 48 hours after verteporfin administration.[2]

Dogs and rats have been treated with inactivated daily doses 32–70 times higher than the dose advised for humans.[5] The 4 weeks of treatment resulted in mild extravascular hemolysis and hematopoiesis in the animals.[5]

InteractionsEdit

Verteporfin is known to interact with the herbal remedy feverfew (Tanacetum parthenium), the latter of which seems to act as an antagonist to verteporfin for unknown reasons. Taking the two substances simultaneously is inadvisable.[6]

Verteporfin does not appear to be metabolized by Cytochrome P450 enzymes, therefore not affecting Cytochrome P450 metabolism of other drugs.[7]

Potential against scarringEdit

Verteporfin is an inhibitor of fibrosis in patients with persistent cholestasis.[8] Verteporfin displays a wide spectrum of anti-fibrotic properties.[5] Verteporfin prevents fibrosis in several human organs.[8] Research has highlighted that verteporfin decreased expression of fibrotic genes in fibroblasts collected from nodules of patients suffering from Dupuytren's contracture.[5] In 2018 information revealed verteporfin stopped fibrosis in the lung.[8] Verteporfin is a marketed drug with a good safety profile. Verteporfin has also been used off-label.[4]

In 2021, scientists tested verteporfin to reveal if the drug would prevent scar tissue in skin.[9] Testing of verteporfin on humans cleft lips will occur in 2021.[10]

This article uses material from the Wikipedia article
 Metasyntactic variable, which is released under the 
Creative Commons
Attribution-ShareAlike 3.0 Unported License
.