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Verteporfin

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Chemistry

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Also known as: Bpd verteporfin, Bpd-ma(sub c), Verteporfin c isomer, Wu713d62n9, Verteporphin, Cl-315555

Molecular Formula

C₄₁H₄₂N₄O₈

Molecular Weight

718.8 g/mol

InChI Key

YTZALCGQUPRCGW-ZSFNYQMMSA-N

FDA UNII

WU713D62N9

A benzoporphyrin derivative that is used in PHOTOCHEMOTHERAPY to treat wet type MACULAR DEGENERATION.

1 2D Structure

Verteporfin

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

3-[(23S,24R)-14-ethenyl-22,23-bis(methoxycarbonyl)-5-(3-methoxy-3-oxopropyl)-4,10,15,24-tetramethyl-25,26,27,28-tetrazahexacyclo[16.6.1.13,6.18,11.113,16.019,24]octacosa-1,3,5,7,9,11(27),12,14,16,18(25),19,21-dodecaen-9-yl]propanoic acid

2.1.2 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)/t38-,41+/m0/s1

2.1.3 InChI Key

YTZALCGQUPRCGW-ZSFNYQMMSA-N

2.1.4 Canonical SMILES

CC1=C(C2=CC3=NC(=CC4=C(C(=C(N4)C=C5C6(C(C(=CC=C6C(=N5)C=C1N2)C(=O)OC)C(=O)OC)C)C)CCC(=O)OC)C(=C3C)CCC(=O)O)C=C

2.1.5 Isomeric SMILES

CC1=C(C2=CC3=NC(=CC4=C(C(=C(N4)C=C5[C@@]6([C@@H](C(=CC=C6C(=N5)C=C1N2)C(=O)OC)C(=O)OC)C)C)CCC(=O)OC)C(=C3C)CCC(=O)O)C=C

2.2 Other Identifiers

2.2.1 UNII

WU713D62N9

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 18-ethenyl-4,4a-dihydro-3,4-bis(methoxycarbonyl)-4a,8,14,19-tetramethyl-23h,25h-benzo(b)porphine-9,13-dipropanoic Acid Monomethyl Ester

2. Benzoporphyrin Derivative Monoacid Ring A

3. Bpd Verteporfin

4. Bpd-ma

5. Verteporfin

6. Verteporphin

2.3.2 Depositor-Supplied Synonyms

1. Bpd Verteporfin

2. Bpd-ma(sub C)

3. Verteporfin C Isomer

4. Wu713d62n9

5. Verteporphin

6. Cl-315555

7. 133513-12-9

8. (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[16.6.1.13,6.18,11.113,16.019,24]octacosa-1,3,5,7,9,11(27),12,14,16,18(25),19,21-dodecaen-9-yl]propanoic Acid.

9. (2r,2(1)s)-8-ethenyl-2(1),2(2)-bis(methoxycarbonyl)-17-(3-methoxy-3-oxopropyl)-2,7,12,18-tetramethyl-2,2(1)-dihydrobenzo[b]porphyrin-13-propanoic Acid

10. (4s,4ar)-18-ethenyl-4,4a-dihydro-3,4-bis(methoxycarbonyl)-4a,8,14,19-tetramethyl-23h,25h-benzo[b]porphine-9,13-dipropanoic Acid 9-methyl Ester

11. 23h,25h-benzo(b)porphine-9,13-dipropanoic Acid, 18-ethenyl-4,4a-dihydro-3,4-bis(methoxycarbonyl)-4a,8,14,19-tetramethyl-, 9-monomethyl Ester, Trans-

12. 3-[(1z,6z,12z,17z,23s,24r)-14-ethenyl-22,23-bis(methoxycarbonyl)-5-(3-methoxy-3-oxopropyl)-4,10,15,24-tetramethyl-25,26,27,28-tetraazahexacyclo[16.6.1.1(3,6).1(8,11).113,16.019,24]octacosa-1,3(28),4,6,8,10,12,14,16(26),17,19,21-dodecaen-9-yl]propanoic Acid

13. Bpd-ma-a1

14. Unii-0x9pa28k43

15. Verteporfin [usan:usp:inn:ban]

16. Verteporfin-mac

17. Verteporfin C5 Isomer

18. Schembl6219

19. (+-)-trans-3,4-dicarboxy-4,4a-dihydro-4a,8,14,19-tetramethyl-18-vinyl-23h,25h-benzo(b)porphine-9,13-dipropionic Acid, 3,4,9-trimethyl Ester Mixture With (+-)-trans-3,4-dicarboxy-4,4a-dihydro-4a,8,14,19-tetramethyl-18-vinyl-23h,25h-benzo(b)porphine-9,13-dipropionic Acid, 3,4,13-trimethyl Ester

20. Trans-3,4-dicarboxy-4,4a-dihydro-4a,8,14,19-tetramethyl-18-vinyl-23h,25h-benzo(b)porphine-9,13-dipropionic Acid 3,4,9-trimethyl Ester

21. Unii-wu713d62n9

22. Chembl2052016

23. Chembl3822934

24. Schembl14257223

25. Chebi:60775

26. Dtxsid30892511

27. 0x9pa28k43

28. Dtxsid001031353

29. Ex-a1344

30. Nsc836163

31. S1786

32. Ccg-270403

33. Db00460

34. Nsc-836163

35. Ncgc00346712-01

36. Ncgc00346712-02

37. 23h,25h-benzo(b)porphine-9,13-dipropanoic Acid, 18-ethenyl-4,4a-dihydro-3,4-bis(methoxycarbonyl)-4a,8,14,19-tetramethyl-, Monomethyl Ester, Trans-

38. Sw219955-1

39. J2.000.745a

40. Ab01566862_01

41. A899099

42. J-005685

43. (2r,21s)-2,21-dihydro-8-vinyl-2,7,12,18-tetramethyl-17-[2-(methoxycarbonyl)ethyl]-21,22-bis(methoxycarbonyl)-21h,23h-benzo[b]porphyrin-13-propionic Acid

44. (2r,21s)-8-ethenyl-2,21-dihydro-13-(3-hydroxy-3-oxopropyl)-17-(3-methoxy-3-oxopropyl)-2,7,12,18-tetramethyl-22h,24h-benzo[b]porphyrin-21,22-dicarboxylic Acid Dimethyl Ester

45. 3-[(23s,24r)-14-ethenyl-22,23-bis(methoxycarbonyl)-5-(3-methoxy-3-oxopropyl)-4,10,15,24-tetramethyl-25,26,27,28-tetrazahexacyclo[16.6.1.13,6.18,11.113,16.019,24]octacosa-1,3,5,7,9,11(27),12,14,16,18(25),19,21-dodecaen-9-yl]propanoic Acid

46. 9-methyl-trans-18-ethenyl-4,4a-dihydro-3,4-bis(methoxycarbonyl)-4a,8,14,19-tetramethyl-23h,25h-benzo(b)porphine-9,13-dipropanoate,dl-

2.4 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₄₁H₄₂N₄O₈
Molecular Weight	718.8 g/mol
XLogP3	4.9
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	10
Rotatable Bond Count	12
Exact Mass	718.30026431 g/mol
Monoisotopic Mass	718.30026431 g/mol
Topological Polar Surface Area	174 Å²
Heavy Atom Count	53
Formal Charge	0
Complexity	1500
Isotope Atom Count	0
Defined Atom Stereocenter Count	2
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Information

1 of 2
Drug Name	Visudyne
PubMed Health	Verteporfin (Injection)
Drug Classes	Photosensitizing Agent
Drug Label	Visudyne (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), represented by the following struc...
Active Ingredient	Verteporfin
Dosage Form	Injectable
Route	Injection
Strength	15mg/vial
Market Status	Prescription
Company	Valeant Pharms

2 of 2
Drug Name	Visudyne
PubMed Health	Verteporfin (Injection)
Drug Classes	Photosensitizing Agent
Drug Label	Visudyne (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), represented by the following struc...
Active Ingredient	Verteporfin
Dosage Form	Injectable
Route	Injection
Strength	15mg/vial
Market Status	Prescription
Company	Valeant Pharms

4.2 Drug 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.

FDA Label

Visudyne is indicated for the treatment of:

- adults with exudative (wet) age-related macular degeneration (AMD) with predominantly classic subfoveal choroidal neovascularisation (CNV) or;

- adults with subfoveal choroidal neovascularisation secondary to pathological myopia.

5 Pharmacology and Biochemistry

5.1 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.

5.2 MeSH Pharmacological Classification

Photosensitizing Agents

Drugs that are pharmacologically inactive but when exposed to ultraviolet radiation or sunlight are converted to their active metabolite to produce a beneficial reaction affecting the diseased tissue. These compounds can be administered topically or systemically and have been used therapeutically to treat psoriasis and various types of neoplasms. (See all compounds classified as Photosensitizing Agents.)

5.3 ATC Code

S01LA01

5.4 Absorption, Distribution and Excretion

Route of Elimination

Elimination is by the fecal route, with less than 0.01% of the dose recovered in urine.

5.5 Metabolism/Metabolites

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.

5.6 Biological 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%.

5.7 Mechanism of Action

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. As singlet oxygen and reactive oxygen radicals are cytotoxic, Verteporfin can also be used to destroy tumor cells.

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