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129497-78-5 分子结构
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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编号:343
分子式:C41H42N4O8
平均质量:718.79418
单一同位素质量:718.30026432
SMILES和InChIs

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

引用这个纪录

CBID:343 http://www.chembase.cn/molecule-343.html

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名称和登记号

名称和登记号

名称 登记号
IUPAC标准名
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传统名
verteporfin
商标名
Visudyne
别名
verteporfin
Verteporfin
CAS号
129497-78-5
PubChem SID
46506236
160963806
PubChem CID
5362420

数据来源

数据来源

所有数据来源 商品来源 非商品来源
数据来源 数据ID
DrugBank DB00460 external link
PubChem 5362420 external link
数据来源 数据ID 价格

理论计算性质

理论计算性质

JChem ALOGPS 2.1
Acid pKa 4.1214423  质子受体
质子供体 LogD (pH = 5.5) 5.98184 
LogD (pH = 7.4) 4.304667  Log P 6.3396554 
摩尔折射率 199.0848 cm3 极化性 79.63175 Å3
极化表面积 173.56 Å2 可自由旋转的化学键 12 
里宾斯基五规则 false 
Log P 5.05  LOG S -4.75 
溶解度 1.28e-02 g/l 

分子性质

分子性质

理化性质 生物活性(PubChem)
疏水性(logP)
2.1 expand 查看数据来源

详细说明

详细说明

DrugBank DrugBank
DrugBank -  DB00460 external link
Item Information
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

参考文献

参考文献

供应商提供 Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • 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
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专利

专利

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