Guidechem | China Chemical Manufacturers,suppliers,B2B Marketplace
Encyclop..
  • Products
  • Encyclopedia
  • Buy offers
  • Suppliers
Home> Encyclopedia >   /  Pharmaceutical  /  Pharmaceutical Intermediates  /  Organic Intermediate
Verteporfin structure
Verteporfin structure

Verteporfin

CAS No.: 129497-78-5
Molecular Weight:718.79418
Modify Date.: 2022-11-27 20:31
Introduction: Verteporfin was introduced in Switzerland as a second-generation photosensitizer forphotodynamic therapy of wet age-related macular degeneration in patients with subfovealchoroidal neovascularisation. It is constituted of a mixture of two regioisomers resultingfrom nonselective monohydrolysis of the methyl tetraester. Upon irradiation with a lowenergynonheat-generating laser light of 689nm wavelength, both regioisomericbenzoporphyrins are responsible for the local generation of singlet oxygen leading to freeradical damage of neovascular endothelial cells in subfoveal lesions of patients with agerelatedmacular degeneration. The lipophilic drug is injected i.v. as a liposomal formulationin order to favor its uptake by plasma lipoproteins and distribution to cells with a highexpression of low density lipoprotein receptors such as tumor and neovascular endothelialcells. Verteporfin is also being developed for the treatment of other eye diseases, nonmelanomaskin cancer and psoriasis. View more+
1. Names and Identifiers
1.1 Name
Verteporfin
1.2 Synonyms

,3(28),4,6,8,10,12,14,16(26),17,19,21-dodécaén-9-yl]propanoïque - acide 3-[(1Z,6Z,12Z,17Z,23S,24R)-14-éthényl-22,23-bis(méthoxycarbonyl)-9-(3-méthoxy-3-oxopropyl)-4,10,15,24-tétraméthyl-25,26,27,28-té ,4,6,8,10,12,14,16(26),17,19,21-dodecaen-9-yl]propanoic acid - 3-[(1Z,6Z,12Z,17Z,23S,24R)-14-ethenyl-22,23-bis(methoxycarbonyl)-9-(3-methoxy-3-oxopropyl)-4,10,15,24-tetramethyl-25,26,27,28-tetraazahex ,4,6,8,10,12,14,16(26),17,19,21-dodecaen-9-yl]propansäure--3-[(1Z,6Z,12Z,17Z,23S,24R)-14-ethenyl-22,23-bis(methoxycarbonyl)-9-(3-methoxy-3-oxopropyl)-4,10,15,24-tetramethyl-25,26,27,28-tetraazahexacyc ,6,8(27),9,11,13,15,17,19,21-dodecaen-5-yl]propanoic acid 24H,26H-Benzo[b]porphine-9,13-dipropanoic acid, 18-ethenyl-4,4a-dihydro-3,4-bis(methoxycarbonyl)-4a,8,14,19-tetramethyl-, monomethyl ester, (4R,4aS)-rel- 3-[(1Z,6Z,12Z,17Z,23S,24R)-22,23-Bis(methoxycarbonyl)-5-(3-methoxy-3-oxopropyl)-4,10,15,24-tetramethyl-14-vinyl-25,26,27,28-tetraazahexacyclo[16.6.1.1.1.1.0]octacosa-1,3(28),4 ,6,8,10,12,14,16(26),17,19,21-dodecaen-9-yl]propanoic acid - 3-[(1Z,6Z,12Z,17Z,23S,24R)-22,23-bis(methoxycarbonyl)-9-(3-methoxy-3-oxopropyl)-4,10,15,24-tetramethyl-14-vinyl-25,26,27,28-tetraazahexacyc lo[16.6.1.1.1.1.0]o 3-[(2Z,6Z,11Z,17Z,23R,24S)-22,23-Bis(methoxycarbonyl)-9-(3-methoxy-3-oxopropyl)-4,10,15,24-tetramethyl-14-vinyl-25,26,27,28-tetraazahexacyclo[16.6.1.13,6.18,11.113,16.019,24]octacosa-1(25),2,4 9-methyl (I)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 trans-18-Ethenyl-4,4a-dihydro-3,4-bis(methoxycarbonyl)-4a,8,14,19-tetramethyl-23H,25H-benzo[b]porphine-9,13-dipropionic Acid Monomethyl Ester 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 UNII-0X9PA28K43 VERTEPIRFIN VERTEPORFIN (200 MG) VERTEPORFIN D ISOMER Verteporfin(DB00460) Verteporphin Verteprofin Visudyne

1.3 CAS No.
129497-78-5
1.4 Molecular Formula
C41H42N4O8 (isomer)
1.5 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
1.6 InChkey
YTZALCGQUPRCGW-ZSFNYQMMSA-N
1.7 Canonical Smiles
COC(=O)CCC1=C2NC(=C1C)\C=C3[C@@]4(C)C(=CC=C(C(=O)OC)[C@H]4C(=O)OC)C(\C=C5C(C)=C(C=C)C(=C/C6C(C)=C(CCC(O)=O)C(/N=6)=C/2)/N\5)=N\3
1.8 Isomers Smiles
C=CC1C2NC(C=1C)=CC1=NC([C@@]3([C@@](C(OC)=O)([H])C(C(OC)=O)=CC=C13)C)=CC1NC(=C(C=1C)CCC(OC)=O)C=C1N=C(C(=C1CCC(O)=O)C)C=2
2. Properties
2.1 Density
1.4±0.1 g/cm3 (Predicted)
2.1 Boiling point
°Cat760mmHg
2.1 Refractive index
1.644 (Predicted)
2.1 Flash Point
°C
2.1 Precise Quality
1436.60000
2.1 PSA
337.48000
2.1 logP
10.24600
2.1 Solubility
DMSO: soluble2mg/mL, clear (warmed)
2.2 Appearance
dark green to black solid
2.3 Storage
?20°C
2.4 Water Solubility
DMSO: soluble2mg/mL, clear (warmed)
2.5 StorageTemp
-20°C
3. Use and Manufacturing
3.1 Usage
Treatment of age-related macular degeneration
4. Safety and Handling
4.1 RIDADR
NONH for all modes of transport
4.1 WGK Germany
3
4.1 Specification

?Verteporfin (CAS NO.129497-78-5) is also named as Verteporfin [USAN:INN]?; (+-)-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 ; CL 318,952 ; UNII-0X9PA28K43 ; Verteporfin ; Visudyne ; 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- . Verteporfin (CAS NO.129497-78-5) is a benzoporphyrin derivative, is a medication.

5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

no data available

2.2 GHS label elements, including precautionary statements

Pictogram(s) no data available
Signal word

no data available

Hazard statement(s)

no data available

Precautionary statement(s)
Prevention

no data available

Response

no data available

Storage

no data available

Disposal

no data available

2.3 Other hazards which do not result in classification

no data available

6. Other Information
6.0 Mesh
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.)
6.1 Absorption
Elimination is by the fecal route, with less than 0.01% of the dose recovered in urine.
6.2 Metabolism
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.
6.3 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%.
6.4 Mesh Entry Terms
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
6.5 Use Classification
Human drugs -> Visudyne -> EMA Drug Category|Ophthalmologicals -> Human pharmacotherapeutic group|Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients
6.6 Photosensitizer
Verteporfin (trade name Visudyne) belongs to a second generation of porphyrin-based photosensitizer that can be activated by light (wavelength 689nm). It can be used for photodynamic therapy for macular degeneration. Drugs can selectively penetrate into the abnormal blood vessels, generate reactive oxygen species and occlude the abnormal blood vessels with the help of non-thermal laser irradiation, further terminating blood vessel leakage, and saving vision.
Upon being activated by the light, Visudyne forms a cytotoxic product in an aerobic environment. During this process, the porphyrin transfers the absorbed energy to oxygen and forms single-oxygen with a high activity and a short maintenance time. The single-oxygen destroys the biological structure within its range of diffusion. This process leads to localized vascular atresia and cell destruction, further leading to cell death in a particular environment.
In plasma, verteporfin is mainly carried by low density lipoprotein (LDL). The application of Visudyne for photodynamic therapy (PDT) has selectivity. On the one hand, it depends on the choice of light irradiation site. On the other hand, the expression of LDL receptors is enhanced in rapidly proliferating cells, including choroidal neovascular endothelial cells, so that rapid proliferative cells can selectively and rapidly ingest and accumulate verteporfin. Choroidal neovascularization is more rapid and selective than retinal pigment epithelium in absorbing the Visudyne, whereas in other ocular structures, the drug content is small. Therefore, the drug can selectively destroy choroidal neovascularization. It can be used for the treatment of continuous deterioration or loss of vision caused by wet age-related macular degeneration, pathological myopia and ocular histoplasmosis related to the choroidal neovascularization
6.7 Adverse reactions
Common adverse effects of Visudyne include visual impairment. Local infusion and rash may occur during local injection. It can be occurred of cataract, diplopia, tears, conjunctivitis, dry eyes, eye itching, severe visual loss and conjunctiva, retinal and vitreous hemorrhage, high blood pressure, atrial fibrillation, peripheral vascular disorders, varicose veins, hypoesthesia, sleep disorders, headache, dizziness, weakness, fever, creatinine, cough, pharyngitis, pneumonia, influenza-like syndrome, back pain, abnormal liver function test indicators, prostate disorders, proteinuria, nausea, constipation, gastrointestinal cancer, eczema, anemia, reduction or increases in leukocyte count, hearing impairment and so on.
6.8 Precautions
Visudyne should be disabled in patients who are highly allergic to it and its derivatives, and patients who received other photosensitizers within 3 months or with porphyria. Patients of serious or moderately serious liver dysfunction should be cautious upon receiving vitamin treatment. Vitamin and other drugs should not be dissolved in the same solution. Avoid direct exposure to drugs. If a patient has a severe vision loss (vision loss or more than 4 lines) within 1 week after treatment, the patients should discontinue the treatment until the vision returns to the initial state. Care should be taken before weighing the pros and cons of treatment. Patients of liver dysfunction and photodynamic therapy discomfort should take with caution; patients, within 6 days after treatment, should avoid exposure of the skin and eyes to light; avoid excessive and prolonged treatment. Do not use in a brightly lit environment. Avoid the use of visudyne salt solution. If liquid spills, wipe it with a damp cloth. Do not let it touch the eye or skin. Verteporfin leakage may cause severe pain, inflammatory reactions, and discoloration at the injection site. Analgesics can be simultaneously given to relieve pain during the injection. If you find verteporfin leakage, immediately stop the injection, and give cold pressure. The affected area should be carefully protected against direct light exposure until swelling and skin color return to normal. Vitamins should be used with care for patients with general anesthesia.
Patients treated with Visudyne were in a light-sensitive state within 48 hours of injection. Within 48 hours of treatment, the skin and eyes mustn’t be exposed directly to daylight or bright artificial light. If you have to be exposed to the outdoors during the day within 48 hours of treatment, you should wear a suitable jacket and wear sunglasses for protection.
6.9 Uses
Treatment of age-related macular degeneration
6.10 Brand name
Visudyne (QLT).
6.11 Target
Value
6.12 Description
Verteporfin was introduced in Switzerland as a second-generation photosensitizer for photodynamic therapy of wet age-related macular degeneration in patients with subfoveal choroidal neovascularisation. It is constituted of a mixture of two regioisomers resulting from nonselective monohydrolysis of the methyl tetraester. Upon irradiation with a lowenergy nonheat-generating laser light of 689nm wavelength, both regioisomeric benzoporphyrins are responsible for the local generation of singlet oxygen leading to free radical damage of neovascular endothelial cells in subfoveal lesions of patients with agerelated macular degeneration. The lipophilic drug is injected i.v. as a liposomal formulation in order to favor its uptake by plasma lipoproteins and distribution to cells with a high expression of low density lipoprotein receptors such as tumor and neovascular endothelial cells. Verteporfin is also being developed for the treatment of other eye diseases, nonmelanoma skin cancer and psoriasis.
6.13 Description
Verteporfin is a photosensitizer used during photodynamic therapy to eliminate abnormal blood vessels in the eye that are associated with conditions such as macular degeneration. It accumulates in these abnormal blood vessels and, when activated by nonthermal red light with a wavelength of 693 nm in the presence of oxygen, produces a highly reactive short-lived singlet oxygen and other reactive oxygen radicals, generating local damage to the endothelium and vessel occlusion. Verteporfin can also inhibit autophagosome formation by directly targeting and modifying p62, a scaffold and adaptor protein that binds both polyubiquitinated proteins destined for degradation and LC3 on autophagosomal membranes.
6.14 Originator
QLT Inc. (Canada)
6.15 Uses
Verteporfin is a photosensitizer that is used in photodynamic therapy (PDT). Verteporfin can accumulate in tumor tissues allowing for 30 to 150 minutes optimal PDT after intravenous administration.
6.16 Biochem/physiol Actions
Verteporfin is a photosensitizer for photodynamic therapy to eliminate the abnormal blood vessels in the eye associated with conditions such as macular degeneration. Verteporfin accumulates in 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 localizes predominantly in mitochondria.
7. Recommended Suppliers
Global67SuppliersView all >>
  • Products:Cangzhou Enke Pharma-tech Co.,Ltd (China) is a leading manufacturer of innovative chemistry products and services throughout the pharmaceutical R&D process and commercial production.
  • Tel:0086-317-5296180
  • Email:sale@enkepharma.com
Verteporfin
  • Purity:99%Packing: 200kg/bag FOB
  • Price: 111 USD/kilogram
  • Time: 2022/08/11
Inquire
  • Products:Pharmaceutical raw materials,Chemical reagent, Food aditives,Plant ExtracPharmaceutical and pesticide intermediates.
  • Tel:86-431-81915458
  • Email:cathytan@jltely.com
Verteporfin
  • Purity:99%Packing: 200kg/bag FOB
  • Price: 1 USD/gram
  • Time: 2022/12/02
Inquire
  • Products:Chemicals,Drugs ,Blotter ,Pill,Raw...
  • Tel:1-0-3137823697
  • Email:SROOCHEM@protonmail.com
Verteporfin
  • Purity:99%Packing: 200kg/bag FOB
  • Price: 1200 USD/kilogram
  • Time: 2022/12/04
Inquire
  • Products:Manufacture & Supply Biopharm Chemical, Specialty Chemical, PetroChemical.
  • Tel:86-592-8883942
  • Email:sale@amitychem.com
Factory Supply Verteporfin
  • Purity:99%Packing: 200kg/bag FOB
  • Price: 0.1 USD/kilogram
  • Time: 2022/07/07
Inquire
  • Products:Chemical products
  • Tel:86-571-88938639
  • Email:sales-gc@dycnchem.com
Verteporfin
  • Purity:99%Packing: 200kg/bag FOB
  • Price: 1 USD/kilogram
  • Time: 2022/12/02
Inquire