WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 203120
Description: Verteporfin, also known as Benzoporphyrin derivative monoacid ring A or BPD-MA, is a benzoporphyrin derivative and 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. Verteporfin is also used off-label for the treatment of central serous retinopathy.
MedKoo Cat#: 203120
Chemical Formula: C41H42N4O8
Exact Mass: 718.30026
Molecular Weight: 718.79
Elemental Analysis: C, 68.51; H, 5.89; N, 7.79; O, 17.81
Synonym: DB00460, CL 318952, BPD-MA, BpdMA, Benzoporphyrin D, Benzoporphyrin derivative monoacid ring A, Verteporfin, Visudyne.
IUPAC/Chemical Name: (1): 3-[(23S,24R)-14-ethenyl-5-(3-methoxy-3-oxopropyl)-22,23-bis(methoxycarbonyl)-4,10,15,24-tetramethyl-25,26,27,28-tetraazahexacyclo[18.104.22.168,6.18,11.113,16.019,24]octacosa-1,3,5,7,9,11(27),12,14,16,18(25),19,21-dodecaen-9-yl]propanoic acid.
InChi Key: YTZALCGQUPRCGW-MXVXOLGGSA-N
InChi Code: 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
SMILES Code: O=C(O)CCC1=C(C)C(/C=C2C(C=C)=C(C)/C(N/2)=C/3)=N/C1=C\C(N4)=C(CCC(OC)=O)C(C)=C4/C=C5[C@]6(C)[C@H](C(OC)=O)C(C(OC)=O)=CC=C6C3=N/5.
Verteporfin is A synthetic light-activated agent with photodynamic activity. Upon systemic administration, verteporfin accumulates in neovessels in the eye and, once stimulated by nonthermal red light in the presence of oxygen, produces highly reactive short-lived singlet oxygen and other reactive oxygen radicals, resulting in local damage to neovascular endothelium and blood vessel occlusion. (From NCI's webpages).
VISUDYNEÂ® (verteporfin for injection) is a light activated drug used in photodynamic therapy. The finished drug product is a lyophilized dark green cake. Verteporfin is a 1:1 mixture of two regioisomers (I and II)
The chemical names for the verteporfin regioisomers are: 9-methyl (I) and 13-methyl (II) trans-(Â± )-18-ethenyl-4,4a-dihydro-3,4-bis(methoxycarbonyl)-4a,8,14,19-tetramethyl-23H, 25H-benzo[b]porphine-9,13-dipropanoate. The molecular formula is C41H42N4O8 with a molecular weight of approximately 718.8. Each mL of reconstituted VISUDYNE contains: ACTIVE: Verteporfin, 2 mg. INACTIVES: Lactose, egg phosphatidylglycerol, dimyristoyl phosphatidylcholine, ascorbyl palmitate and butylated hydroxytoluene
VISUDYNE (verteporfin for injection) therapy is indicated for the treatment of patients with predominantly classic subfoveal choroidal neovascularization due to age-related macular degeneration, pathologic myopia or presumed ocular histoplasmosis. There is insufficient evidence to indicate VISUDYNE for the treatment of predominantly occult subfoveal choroidal neovascularization.
Mechanism of Action
VISUDYNE (verteporfin for injection) therapy is a two-stage process requiring administration of both verteporfin for injection and nonthermal red light. 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. Therefore, there may be collateral damage to retinal structures following photoactivation including the retinal pigmented epithelium and outer nuclear layer of the retina. The temporary occlusion of choroidal neovascularization (CNV) following Visudyne therapy has been confirmed in humans by fluorescein angiography.
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