| Revision as of 15:53, 10 January 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{drugbox}} taken from revid 467362900 of page Verteporfin for the Chem/Drugbox validation project (updated: 'DrugBank', 'ChEMBL'). |
Latest revision as of 19:41, 9 December 2024 edit CrafterNova (talk | contribs)Extended confirmed users16,639 edits removed duplicate link, wording fixTag: 2017 wikitext editor |
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{{Short description|Pharmaceutical drug}} |
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{{ambox | text = This page contains a copy of the infobox ({{tl|drugbox}}) taken from revid of page ] with values updated to verified values.}} |
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{{Drugbox |
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{{Drugbox |
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| Verifiedfields = changed |
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| Verifiedfields = changed |
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| verifiedrevid = 402873498 |
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| verifiedrevid = 470629762 |
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| IUPAC_name = 3-octacosa-1,3,5,7,9,11(27),12,14,16,18(25),19,21-dodecaen-9-yl]propanoic acid |
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| IUPAC_name = 3-octacosa-1,3,5,7,9,11(27),12,14,16,18(25),19,21-dodecaen-9-yl]propanoic acid |
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| image = Verteporfin.svg |
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| image = Verteporfin.svg |
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<!--Clinical data--> |
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<!--Clinical data--> |
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| tradename = |
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| tradename = Visudyne |
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| Drugs.com = {{drugs.com|monograph|verteporfin}} |
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| Drugs.com = {{drugs.com|monograph|verteporfin}} |
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| MedlinePlus = a607060 |
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| MedlinePlus = a607060 |
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| pregnancy_category = |
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| pregnancy_US = C |
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| legal_status = |
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| licence_EU = yes |
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| legal_US = Rx-only |
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| routes_of_administration = ] |
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| routes_of_administration = ] |
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<!--Pharmacokinetic data--> |
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<!--Pharmacokinetic data--> |
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| bioavailability = |
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| bioavailability = |
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| metabolism = |
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| metabolism = |
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| elimination_half-life = |
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| elimination_half-life = |
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<!--Identifiers--> |
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<!--Identifiers--> |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CAS_number_Ref = {{cascite|correct|??}} |
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| CAS_number_Ref = {{cascite|correct|??}} |
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| CAS_number = 129497-78-5 |
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| CAS_number = 129497-78-5 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = 0X9PA28K43 |
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| UNII = 0X9PA28K43 |
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| KEGG_Ref = {{keggcite|changed|kegg}} |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG = D01162 |
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| KEGG = D01162 |
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| ChEBI_Ref = {{ebicite|changed|EBI}} |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI = 60775 |
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| ChEBI = 60775 |
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| ChEMBL_Ref = {{ebicite|changed|EBI}} |
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| ChEMBL_Ref = {{ebicite|changed|EBI}} |
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| ChEMBL = <!-- blanked - oldvalue: 1200573 --> |
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| ChEMBL = 2218885 |
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<!--Chemical data--> |
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| C=41 | H=42 | N=4 | O=8 |
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| C=41 | H=42 | N=4 | O=8 |
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| molecular_weight = 718.794 g/mol |
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| smiles = COC(=O)2C(=C\C=C3\c1cc6nc(cc5nc(cc4nc(cc(n1)23C)C(/C)=C4/CCC(=O)OC)c(CCC(O)=O)c5C)C(/C=C)=C6/C)/C(=O)OC |
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| 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(=O)OC)56C |
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| InChI = 1/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 |
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| InChIKey = ZCQHFRFEJXRZDF-YWANUUMDBT |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 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 |
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| StdInChI = 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 |
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| StdInChIKey = ZCQHFRFEJXRZDF-YWANUUMDSA-N |
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| StdInChIKey = ZCQHFRFEJXRZDF-YWANUUMDSA-N |
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}} |
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}} |
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'''Verteporfin''' (trade name '''Visudyne'''), a ] derivative, is a ] used as a ] for ] to eliminate the abnormal ]s in the ] associated with conditions such as the wet form of ]. Verteporfin accumulates in these abnormal blood vessels and, when stimulated by nonthermal red light with a ] of 689 nm<ref>{{cite web|url=http://www.bausch.com/Portals/109/-/m/BL/United%20States/Files/Package%20Inserts/Pharma/visudyne-package-insert.pdf |title=Visudyne package insert}}</ref> in the presence of ], produces highly reactive short-lived singlet oxygen and other reactive ]s, resulting in local damage to the ] and blockage of the vessels.<ref name="Drugs.com">Verteporfin {{drugs.com|monograph|verteporfin}}</ref><ref name=Scott2000>{{cite journal | vauthors = Scott LJ, Goa KL | title = Verteporfin | journal = Drugs & Aging | volume = 16 | issue = 2 | pages = 139–46; discussion 147–8 | date = February 2000 | pmid = 10755329 | doi = 10.2165/00002512-200016020-00005 | s2cid = 260491296 }}</ref> |
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Verteporfin is also used ] for the treatment of ].<ref name=offlab>{{cite journal | vauthors = Karim SP, Adelman RA | title = Profile of verteporfin and its potential for the treatment of central serous chorioretinopathy | journal = Clinical Ophthalmology | volume = 7 | pages = 1867–75 | year = 2013 | pmid = 24092965 | pmc = 3788817 | doi = 10.2147/OPTH.S32177 | doi-access = free }}</ref> |
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==Administration== |
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Verteporfin is usually injected ]ly into the largest arm vein.<ref name=verte2018Dec/> It is injected at a dose of 6 mg/m2 and light-activated.<ref name=verte2018Dec>{{Citation | last = Mohede | first = Daan C.J. | title = Verteporfin as a Medical Treatment in Peyronie's Disease | journal = Sex Med | date = 28 September 2018 | volume = 6 | issue = 4 | pages = 302–308 | doi = 10.1016/j.esxm.2018.08.002 | pmid = 30274909 | pmc = 6302152 | language = English }}</ref> It is usually given 15 minutes before laser treatment.<ref name="Drugs.com" /> This dose can be repeated 4 times per year.<ref name=verte2018Dec/> |
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==Contraindications== |
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{{expand section|date=December 2024}} |
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].<ref name="Drugs.com" /> |
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==Side effects== |
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Most common side effects are blurred vision, headache, and local effects at the injection site. Also, ]; it is strictly advised to avoid exposure to sunlight and unscreened lighting until 48 hours after verteporfin administration.<ref name="Drugs.com" /> |
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Dogs and rats have been treated with inactivated daily doses 32–70 times higher than the dose advised for humans.<ref name=verte2018Dec/> The 4 weeks of treatment resulted in mild extravascular hemolysis and hematopoiesis in the animals.<ref name=verte2018Dec/> |
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== Light-activated cytotoxicity == |
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Used by itself, the clinical recommended dose for verteporfin is not ] to human tissue.<ref name=cyto2023>{{cite web |
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| title = SUMMARY OF PRODUCT CHARACTERISTICS |
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|quote = By itself, the clinically recommended dose of verteporfin is not cytotoxic. It produces cytotoxic agents only when activated by light in the presence of oxygen. When energy absorbed by the porphyrin is transferred to oxygen, highly reactive short-lived singlet oxygen is generated. Singlet oxygen causes damage to biological stmctures within the diffusion range, leading to local vascular occlusion, cell damage and, under certain conditions, cell death. |
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| url = https://www.ema.europa.eu/en/documents/product-information/visudyne-epar-product-information_en.pdf |
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| website = ema.europa.eu |
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| date = 13 December 2023 |
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|archive-url = https://web.archive.org/web/20231213134659/https://www.ema.europa.eu/en/documents/product-information/visudyne-epar-product-information_en.pdf |
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| access-date = 13 December 2023|archive-date = 2023-12-13 |
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}}</ref> Though under light activation, in the presence of oxygen, it can form cytotoxic agents inside the tissue.<ref name=cyto2023/> The agents form when the porphyrin absorbs enough light to generate a reactive but short-lived singlet oxygen.<ref name=cyto2023/> The brief singlet oxygen can micro damage biological structures, leading to a local vascular occlusion.<ref name=cyto2023/> |
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== Interactions == |
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Verteporfin is known to interact with the herbal remedy ] (''Tanacetum parthenium''), the latter of which seems to act as an antagonist to verteporfin for unknown reasons. Taking the two substances simultaneously is inadvisable.<ref>{{cite web |url=https://www.drugs.com/drug-interactions/feverfew-with-verteporfin-2368-0-2298-0.html |title=Feverfew and Verteporfin Interactions | work = Drugs.com |access-date=14 April 2015}}</ref> |
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Verteporfin does not appear to be metabolized by ] enzymes, therefore not affecting ] metabolism of other drugs.<ref name="Prescribing info">{{cite web |title=Visudyne (verteporfin for injection) prescribing information |url=https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/021119s027lbl.pdf |website=FDA |access-date=12 April 2021}}</ref> |
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==Shortages== |
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In May 2020, a low manufacturing capacity caused disruption.<ref name=shortage/> This affected the usage of verteporfin among providers and patients in Europe.<ref name=shortage>{{cite web | url = https://www.ema.europa.eu/en/documents/shortage/shortage-visudyne-verteporfin-supply-shortage_en.pdf | title = Shortage of Visudyne (verteporfin) | last = EMA | date =5 November 2021 | website =ema.europa.eu | access-date = 1 February 2022 }}</ref> The EMA expected normal manufacturing to return by the first quarter 2022.<ref name=shortage/> |
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== Off-label use in retinopathy == |
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Verteporfin may be used off-label for treating central serous retinopathy.<ref name=offlab/><ref name=shortage/> |
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== References == |
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{{reflist}} |
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==External links == |
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* {{cite web | url = http://www.visudyne.com/ | work = Novartis | title = Visudyne }} |
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{{Ocular vascular disorder agents}} |
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{{Intracellular chemotherapeutic agents}} |
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] |
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] |
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] |