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 ID: 588
• Molecular Formular: C68H74N8O11
• Molecular Mass: 1179.36216
• Monoisotopic Mass: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: 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 Traditional name: 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
• Brand Name: Photofrin
• Synonyms: DHE; DHP ether; Dihematoporphyrin ether; Porfimer sodium; Porfimer

Database IDs

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

CALCULATED PROPERTIES

JChem

• Acid pKa: 3.2120955
• H Acceptors: 15
• H Donor: 10
• LogD (pH = 5.5): 7.7656713
• LogD (pH = 7.4): 1.093921
• Log P: 10.544568
• Molar Refractivity: 330.3059 cm^3
• Polarizability: 135.8459 Å^3
• Polar Surface Area: 313.61 Å^2
• Rotatable Bonds: 18
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: 4.8
• LOG S: -4.7
• Solubility (Water): 2.38e-02 g/l

PROPERTIES

Physical Property

• Hydrophobicity(logP): 2.8

DETAILS

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