Verteporfin
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MedKoo CAT#: 203120

CAS#: 129497-78-5

Description: Verteporfin, also known as Benzoporphyrin derivative monoacid ring A or BPD-MA, is a benzoporphyrin derivative and 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. Verteporfin is also used off-label for the treatment of central serous retinopathy.


Price and Availability

Size
Price

10mg
USD 150
100mg
USD 950
Size
Price

25mg
USD 290
200mg
USD 1750
Size
Price

50mg
USD 520
1g
Ask price

Verteporfin, purity > 96%, is in stock. The same day shipping out after order is received. Note: the estimated shipping out time for order > 2g may be 2 weeks.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 203120
Name: Verteporfin
CAS#: 129497-78-5
Chemical Formula: C41H42N4O8
Exact Mass: 718.30026
Molecular Weight: 718.79
Elemental Analysis: C, 68.51; H, 5.89; N, 7.79; O, 17.81


Synonym: DB00460, CL 318952, BPD-MA, BpdMA, Benzoporphyrin D, Benzoporphyrin derivative monoacid ring A, Verteporfin, Visudyne.

IUPAC/Chemical Name: (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.

InChi Key: YTZALCGQUPRCGW-MXVXOLGGSA-N

InChi Code: 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

SMILES Code: O=C(O)CCC1=C(C)C(/C=C2C(C=C)=C(C)/C(N/2)=C/3)=N/C1=C\C(N4)=C(CCC(OC)=O)C(C)=C4/C=C5[C@]6(C)[C@H](C(OC)=O)C(C(OC)=O)=CC=C6C3=N/5.


Technical Data

Appearance:
Black solid powder

Purity:
>95% (or refer to the Certificate of Analysis)

Safety Data Sheet (MSDS):

Shipping Condition:
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition:
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility:
Soluble in DMSO, not in water

Shelf Life:
>2 years if stored properly

Drug Formulation:
This drug may be formulated in DMSO

Stock Solution Storage:
0 - 4 C for short term (days to weeks), or -20 C for long term (months).

Harmonized System Code:
2934.99.90.01


Additional Information

Verteporfin is A synthetic light-activated agent with photodynamic activity. Upon systemic administration, verteporfin accumulates in neovessels in the eye and, once stimulated by nonthermal red light in the presence of oxygen, produces highly reactive short-lived singlet oxygen and other reactive oxygen radicals, resulting in local damage to neovascular endothelium and blood vessel occlusion. (From NCI's webpages).
 
DRUG DESCRIPTION
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)
The chemical names for the verteporfin regioisomers are: 9-methyl (I) and 13-methyl (II) trans-(± )-18-ethenyl-4,4a-dihydro-3,4-bis(methoxycarbonyl)-4a,8,14,19-tetramethyl-23H, 25H-benzo[b]porphine-9,13-dipropanoate. The molecular formula is C41H42N4O8 with a molecular weight of approximately 718.8. Each mL of reconstituted VISUDYNE contains:  ACTIVE: Verteporfin, 2 mg. INACTIVES: Lactose, egg phosphatidylglycerol, dimyristoyl phosphatidylcholine, ascorbyl palmitate and butylated hydroxytoluene
 
INDICATIONS
VISUDYNE (verteporfin for injection) therapy is indicated for the treatment of patients with predominantly classic subfoveal choroidal neovascularization due to age-related macular degeneration, pathologic myopia or presumed ocular histoplasmosis. There is insufficient evidence to indicate VISUDYNE for the treatment of predominantly occult subfoveal choroidal neovascularization.
 
Mechanism of Action
VISUDYNE (verteporfin for injection) therapy is a two-stage process requiring administration of both verteporfin for injection and nonthermal red light. 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. Therefore, there may be collateral damage to retinal structures following photoactivation including the retinal pigmented epithelium and outer nuclear layer of the retina. The temporary occlusion of choroidal neovascularization (CNV) following Visudyne therapy has been confirmed in humans by fluorescein angiography.
 


References

    1: Karim SP, Adelman RA. Profile of verteporfin and its potential for the treatment of central serous chorioretinopathy. Clin Ophthalmol. 2013;7:1867-75. doi: 10.2147/OPTH.S32177. Epub 2013 Sep 19. Review. PubMed PMID: 24092965; PubMed Central PMCID: PMC3788817.

2: Ziemssen F, Heimann H. Evaluation of verteporfin pharmakokinetics--redefining the need of photosensitizers in ophthalmology. Expert Opin Drug Metab Toxicol. 2012 Aug;8(8):1023-41. doi: 10.1517/17425255.2012.701617. Epub 2012 Jul 5. Review. PubMed PMID: 22762303.

3: 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. doi: 10.1007/s00417-010-1307-z. Epub 2010 Feb 17. Review. PubMed PMID: 20162298.

4: Shah GK, Sang DN, Hughes MS. Verteporfin combination regimens in the treatment of neovascular age-related macular degeneration. Retina. 2009 Feb;29(2):133-48. doi: 10.1097/IAE.0b013e3181960a28. Review. PubMed PMID: 19202423.

5: Cruess AF, Zlateva G, Pleil AM, Wirostko B. Photodynamic therapy with verteporfin in age-related macular degeneration: a systematic review of efficacy, safety, treatment modifications and pharmacoeconomic properties. Acta Ophthalmol. 2009 Mar;87(2):118-32. doi: 10.1111/j.1755-3768.2008.01218.x. Epub 2008 Jun 13. Review. PubMed PMID: 18577193.

6: Kaiser PK. Verteporfin photodynamic therapy and anti-angiogenic drugs: potential for combination therapy in exudative age-related macular degeneration. Curr Med Res Opin. 2007 Mar;23(3):477-87. Review. PubMed PMID: 17355729.

7: Augustin AJ, Schmidt-Erfurth U. Verteporfin therapy and triamcinolone acetonide: convergent modes of action for treatment of neovascular age-related macular degeneration. Eur J Ophthalmol. 2006 Nov-Dec;16(6):824-34. Review. PubMed PMID: 17191188.

8: Fenton C, Perry CM. Verteporfin: a review of its use in the management of subfoveal choroidal neovascularisation. Drugs Aging. 2006;23(5):421-45. Review. PubMed PMID: 16823995.

9: Schmidt-Erfurth U, Michels S, Augustin A. Perspectives on verteporfin therapy combined with intravitreal corticosteroids. Arch Ophthalmol. 2006 Apr;124(4):561-3. Review. PubMed PMID: 16606885.

10: Wickens J, Blinder KJ. A preliminary benefit-risk assessment of verteporfin in age-related macular degeneration. Drug Saf. 2006;29(3):189-99. Review. PubMed PMID: 16524319.

11: Kaiser PK. Verteporfin therapy in combination with triamcinolone: published studies investigating a potential synergistic effect. Curr Med Res Opin. 2005 May;21(5):705-13. Review. PubMed PMID: 15969870.

12: Verteporfin Roundtable Participants. Guidelines for using verteporfin (Visudyne) in photodynamic therapy for choroidal neovascularization due to age-related macular degeneration and other causes: update. Retina. 2005 Feb-Mar;25(2):119-34. Review. PubMed PMID: 15689800.

13: Arita J, Okuyama T. [Preclinical and clinical profile of verteporfin, a potent photodynamic therapy drug for CNV secondary to AMD]. Nihon Yakurigaku Zasshi. 2004 Dec;124(6):435-44. Review. Japanese. PubMed PMID: 15572848.

14: Huber G, Levy J. Development of verteporfin therapy: a collaboration between pharmaceutical companies, device manufacturers and clinical investigators. Semin Ophthalmol. 2001 Dec;16(4):213-7. Review. PubMed PMID: 15513443.

15: Sickenberg M. Verteporfin therapy for subfoveal choroidal neovascularization in age-related macular degeneration: from clinical trials to clinical practice. Semin Ophthalmol. 2001 Dec;16(4):207-12. Review. PubMed PMID: 15513442.

16: Michels S, Schmidt-Erfurth U. Photodynamic therapy with verteporfin: a new treatment in ophthalmology. Semin Ophthalmol. 2001 Dec;16(4):201-6. Review. PubMed PMID: 15513441.

17: Gaynes BI, Fiscella RG. Safety of verteporfin for treatment of subfoveal choroidal neovascular membranes associated with age-related macular degeneration. Expert Opin Drug Saf. 2004 Jul;3(4):345-61. Review. PubMed PMID: 15268651.

18: Keam SJ, Scott LJ, Curran MP. Spotlight on verteporfin in subfoveal choroidal neovascularisation. Drugs Aging. 2004;21(3):203-9. Review. PubMed PMID: 14979737.

19: Yang YC. Preserving vision with verteporfin photodynamic therapy. Hosp Med. 2004 Jan;65(1):39-43. Review. PubMed PMID: 14964795.

20: Meads C, Hyde C. Photodynamic therapy with verteporfin is effective, but how big is its effect? Results of a systematic review. Br J Ophthalmol. 2004 Feb;88(2):212-7. Review. PubMed PMID: 14736777; PubMed Central PMCID: PMC1772007.