3-[9-(1-{1-[10,14-bis(2-carboxyethyl)-19-(1-hydroxyethyl)-5,9,15,20-tetramethyl-21,22,23,24-tetraazapentacyclo[16.2.1.1^{3,6}.1^{8,11}.1^{13,16}]tetracosa-1(20),2,4,6,8(23),9,11,13(22),14,16,18-undecaen-4-yl]ethoxy}ethyl)-20-(2-carboxyethyl)-14-(1-hydroxyethyl)-5,10,15,19-tetramethyl-21,22,23,24-tetraazapentacyclo[16.2.1.1^{3,6}.1^{8,11}.1^{13,16}]tetracosa-1(21),2,4,6(24),7,9,11,13,15,17,19-undecaen-4-yl]propanoic acid

• ChemBase编号: 588
• 分子式: C68H74N8O11
• 平均质量: 1179.36216
• 单一同位素质量: 1178.54770523
• SMILES: O(C(c1/c/2=C/c3[nH]c(c(c3C)C(O)C)/C=C/3\N=C(C(=C3C)CCC(=O)O)/C=C/3\N=C(/C=c(\[nH]2)/c1C)C(=C3CCC(=O)O)C)C)C(c1c(/c/2=C/c3[nH]c(c(c3C(O)C)C)/C=C/3\N=C(C(=C3C)CCC(=O)O)/C=C/3\N=C(/C=c/1\[nH]2)C(=C3CCC(=O)O)C)C)C
• Canonical SMILES: OC(=O)CCC1=C(C)C2=N/C/1=C\C1=N/C(=C\c3[nH]c(/C=c/4\[nH]/c(=C\2)/c(C)c4C(OC(c2/c/4=C/C5=N/C(=C\C6=N/C(=C\c7[nH]c(/C=c(/c2C)\[nH]4)c(C(O)C)c7C)/C(=C6CCC(=O)O)C)/C(=C5C)CCC(=O)O)C)C)c(c3C(O)C)C)/C(=C1CCC(=O)O)C
• InChI: InChI=1S/C68H74N8O11/c1-29-41(13-17-61(79)80)53-28-56-44(16-20-64(85)86)32(4)48(72-56)24-59-68(36(8)52(76-59)25-58-65(37(9)77)33(5)49(73-58)21-45(29)69-53)40(12)87-39(11)67-35(7)50-22-46-30(2)42(14-18-62(81)82)54(70-46)27-55-43(15-19-63(83)84)31(3)47(71-55)23-57-66(38(10)78)34(6)51(74-57)26-60(67)75-50/h21-28,37-40,73-78H,13-20H2,1-12H3,(H,79,80)(H,81,82)(H,83,84)(H,85,86)/b45-21-,46-22-,47-23-,48-24-,49-21-,50-22-,51-26-,52-25-,53-28-,54-27-,55-27-,56-28-,57-23-,58-25-,59-24-,60-26-
• InChIKey: UZFPOOOQHWICKY-STKOUIOXSA-N

名称和登记号

名称

• IUPAC标准名: 3-[9-(1-{1-[10,14-bis(2-carboxyethyl)-19-(1-hydroxyethyl)-5,9,15,20-tetramethyl-21,22,23,24-tetraazapentacyclo[16.2.1.1^{3,6}.1^{8,11}.1^{13,16}]tetracosa-1(20),2,4,6,8(23),9,11,13(22),14,16,18-undecaen-4-yl]ethoxy}ethyl)-20-(2-carboxyethyl)-14-(1-hydroxyethyl)-5,10,15,19-tetramethyl-21,22,23,24-tetraazapentacyclo[16.2.1.1^{3,6}.1^{8,11}.1^{13,16}]tetracosa-1(21),2,4,6(24),7,9,11,13,15,17,19-undecaen-4-yl]propanoic acid
• IUPAC传统名: 3-[9-(1-{1-[10,14-bis(2-carboxyethyl)-19-(1-hydroxyethyl)-5,9,15,20-tetramethyl-21,22,23,24-tetraazapentacyclo[16.2.1.1^{3,6}.1^{8,11}.1^{13,16}]tetracosa-1(20),2,4,6,8(23),9,11,13(22),14,16,18-undecaen-4-yl]ethoxy}ethyl)-20-(2-carboxyethyl)-14-(1-hydroxyethyl)-5,10,15,19-tetramethyl-21,22,23,24-tetraazapentacyclo[16.2.1.1^{3,6}.1^{8,11}.1^{13,16}]tetracosa-1(21),2,4,6(24),7,9,11,13,15,17,19-undecaen-4-yl]propanoic acid
• 商标名: Photofrin
• 别名: DHE; DHP ether; Dihematoporphyrin ether; Porfimer sodium; Porfimer

登记号

• CAS号: 87806-31-3
• PubChem SID: 160964051
• PubChem CID: 57166

理论计算性质

JChem

• Acid pKa: 3.2120955
• 质子受体: 15
• 质子供体: 10
• LogD (pH = 5.5): 7.7656713
• LogD (pH = 7.4): 1.093921
• Log P: 10.544568
• 摩尔折射率: 330.3059 cm^3
• 极化性: 135.8459 Å^3
• 极化表面积: 313.61 Å^2
• 可自由旋转的化学键: 18
• 里宾斯基五规则: false

ALOGPS 2.1

• Log P: 4.8
• LOG S: -4.7
• 溶解度: 2.38e-02 g/l

分子性质

理化性质

• 疏水性(logP): 2.8

详细说明

DrugBank - DB00707

• Drug Groups: approved; investigational
• Description: The purified component of hematoporphyrin derivative, it consists of a mixture of oligomeric porphyrins. It is used in photodynamic therapy (hematoporphyrin photoradiation); to treat malignant lesions with visible light and experimentally as an antiviral agent. It is the first drug to be approved in the use of photodynamic therapy in the United States. [PubChem]
• Indication: Indicated in the treatment of esophageal cancer.
• Pharmacology: Porfimer is a photosensitizing agent used in the photodynamic therapy (PDT) of tumors. Porfimer is indicated for the palliation of patients with completely obstructing esophageal cancer, or of patients with partially obstructing esophageal cancer who cannot be satisfactorily treated with Nd:YAG laser therapy, reduction of obstruction and palliation of symptoms in patients with completely or partially obstructing endobronchial nonsmall cell lung cancer (NSCLC), and the treatment of microinvasive endobronchial NSCLC in patients for whom surgery and radiotherapy are not indicated. The cytotoxic and antitumor actions of porfimer are light and oxygen dependent. Tumor selectivity in treatment occurs through a combination of selective retention of porfimer and selective delivery of light.
• Affected Organisms: Humans and other mammals
• Half Life: 10-452 hours
• Protein Binding: ~90%
• Distribution: * 0.49 ± 0.28 L/kg [2 mg/kg dose of porfimer sodium to 4 male cancer patients]
• Clearance: * Renal cl=199.7?+/- ?56.9 mL/min [Healthy subjects receiving a single 300-mg oral dose]
• External Links: Wikipedia; RxList; Drugs.com