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(25),2,4,6,8(27),9,11,13,15,17,19,21-dodecaen-9-yl]propanoic acid

• ChemBase ID: 343
• Molecular Formular: C41H42N4O8
• Molecular Mass: 718.79418
• Monoisotopic Mass: 718.30026432
• SMILES: O(C(=O)[C@H]1[C@@]2(C(=CC=C1C(=O)OC)/C/1=C/c3[nH]c(c(c3C)C=C)/C=C/3\N=C(/C=c/4\[nH]/c(=C\C2=N1)/c(c4CCC(=O)OC)C)C(=C3C)CCC(=O)O)C)C
• Canonical SMILES: COC(=O)CCc1/c/2=C/C3=N/C(=C\c4[nH]c(/C=C/5\N=C(/C=c(/c1C)\[nH]2)[C@]1(C)[C@H](C(=O)OC)C(=CC=C51)C(=O)OC)c(c4C=C)C)/C(=C3CCC(=O)O)C
• 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
• InChIKey: YTZALCGQUPRCGW-MXVXOLGGSA-N

NAMES AND DATABASE IDS

Names

• 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(25),2,4,6,8(27),9,11,13,15,17,19,21-dodecaen-9-yl]propanoic acid
• IUPAC Traditional name: verteporfin
• Brand Name: Visudyne
• Synonyms: verteporfin; Verteporfin

Database IDs

• CAS Number: 129497-78-5
• PubChem SID: 46506236; 160963806
• PubChem CID: 5362420

CALCULATED PROPERTIES

JChem

• Acid pKa: 4.1214423
• H Acceptors: 7
• H Donor: 3
• LogD (pH = 5.5): 5.98184
• LogD (pH = 7.4): 4.304667
• Log P: 6.3396554
• Molar Refractivity: 199.0848 cm^3
• Polarizability: 79.63175 Å^3
• Polar Surface Area: 173.56 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: 5.05
• LOG S: -4.75
• Solubility (Water): 1.28e-02 g/l

PROPERTIES

Physical Property

• Hydrophobicity(logP): 2.1

DETAILS

DrugBank - DB00460

• Drug Groups: approved; investigational
• Description: Verteporfin, otherwise known as benzoporphyrin derivative (trade name Visudyne?), 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.
• 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.
• Pharmacology: 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.
• 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.
• Affected Organisms: Humans and other mammals
• Biotransformation: 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.
• 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%.
• Elimination: Elimination is by the fecal route, with less than 0.01% of the dose recovered in urine.
• 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. Epub 2010 Feb 17. [Pubmed] ; 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]
• External Links: Wikipedia; RxList; Drugs.com

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. Epub 2010 Feb 17. Pubmed
• 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