Vinflunine

Iupac Name：methyl (1R,9R,10S,11R,12R,19R)-11-acetyloxy-4-[(12S,14R,16R)-16-(1,1-difluoroethyl)-12-methoxycarbonyl-1,10-diazatetracyclo[12.3.1.03,11.04,9]octadeca-3(11),4,6,8-tetraen-12-yl]-12-ethyl-10-hydroxy-5-methoxy-8-methyl-8,16-diazapentacyclo[10.6.1.01,9.02,7.016,19]nonadeca-2,4,6,13-tetraene-10-carboxylate

CAS No.: 162652-95-1

Molecular Weight：816.944

Modify Date.: 2022-11-22 20:26

Introduction: Vinflunine (also referred to as PM391) is a semisynthetic analog of thenatural vinca alkaloids vinblastine and vincristine that was approved bythe European Medicines Agency (EMEA) in 2009 for the treatment ofadult patients with advanced or metastatic transitional cell carcinoma ofthe urothelial tract after failure of a prior platinum-containing regimen.Vinflunine is synthesized from anhydrovinblastine in asuperacid media (HF-SbF5) and in the presence of a chlorinated solventlike CHCl3 or CCl4. View more+

Request For Quotation

1. Names and Identifiers

1.1 Name: Vinflunine
1.2 Synonyms: 20',20'-Difluoro-3',4'-dihydrovinorelbine 20′,20′-Difluoro-3′,4′-dihydrovinorelbine 3-hydroxy-16-methoxy-1-methyl-6,7-didehydroaspidospermidine-3-carboxylate 4′-Deoxy-20′,20′-difluoro-5′-norvincaleukoblastine 4′-Deoxy-20′,20′-difluoro-8′-norvincaleukoblastine 4'-Deoxy-20' 4'-Deoxy-20',20'-difluoro-5'-norvincaleukoblastine 4'-Deoxy-20',20'-difluoro-8'-norvincaleukoblastine Aspidospermidine-3-carboxylic acid, 4-(acetyloxy)-6,7-didehydro-15-[(2R,4R,6S,8S)-4-(1,1-difluoroethyl)-1,3,4,5,6,7,8,9-octahydro-8-(methoxycarbonyl)-2,6-methano-2H-azecino[4,3-b]indol-8-yl]-3-hydroxy-16-methoxy-1-methyl-, methyl ester, (2β,3β,4β,5α,12R,19α)- Aspidospermidine-3-carboxylic acid, 4-(acetyloxy)-6,7-didehydro-15-[(2R,4R,6S,8S)-4-(1,1-difluoroethyl)-1,3,4,5,6,7,8,9-octahydro-8-(methoxycarbonyl)-2,6-methano-2H-azecino[4,3-b]indol-8-yl]-3-hydroxy-16-methoxy-1-methyl-, methyl ester, (2β,3β,4β,5α,12β,19α)- Aspidospermidine-3-carboxylic acid, 4-(acetyloxy)-6,7-didehydro-15-[(4R,6R,8S)-4-(1,1-difluoroethyl)-1,3,4,5,6,7,8,9-octahydro-8-(methoxycarbonyl)-2,6-methano-2H-azecino[4,3-b]indol-8-yl]-3-hydroxy-16 aspidospermidine-3-carboxylic acid, 4-(acetyloxy)-6,7-didehydro-15-[(4R,6R,8S)-4-(1,1-difluoroethyl)-1,3,4,5,6,7,8,9-octahydro-8-(methoxycarbonyl)-2,6-methano-2H-azecino[4,3-b]indol-8-yl]-3-hydroxy-16-methoxy-1-methyl-, methyl ester, (2Β,3Β,4Β,5α,12Β,19α)- C′-Norvincaleukoblastine, 4′-deoxy-20′,20′-difluoro- C45H54F2N4O8 C'-Norvincaleukoblastine,4'-deoxy-20',20'-difluoro -methoxy-1-methyl-, methyl ester, (2Β,3Β,4Β,5α,12Β,19α)- methyl (2Β,3Β,4Β,5α,12Β,19α)-4-(acetyloxy)-15-[(4R,6R,8S)-4-(1,1-difluoroethyl)-8-(methoxycarbonyl)-1,3,4,5,6,7,8,9-octahydro-2,6-methanoazecino[4,3-b]indol-8-yl]-3-hydroxy-16-methoxy-1-methyl-6,7-didehydroaspidospermidine-3-carboxylate Methyl (2Β,3Β,4Β,5α,12Β,19α)-4-acetoxy-15-[(12S,14R,16R)-16-(1,1-difluoroethyl)-12-(methoxycarbonyl)-1,10-diazatetracyclo[12.3.1.0.0]octadeca-3(11),4,6,8-tetraen-12-yl]- Methyl (2Β,3Β,4Β,5α,12Β,19α)-4-acetoxy-15-[(12S,14R,16R)-16-(1,1-difluoroethyl)-12-(methoxycarbonyl)-1,10-diazatetracyclo[12.3.1.0.0]octadeca-3(11),4,6,8-tetraen-12-yl]-3-hydroxy-16-methoxy-1-methyl-6,7-didehydroaspidospermidine-3-carboxylate MFCD00938122 VINFLUNINE Vinflunine 162652-95-1 Vinflunine Tartrate Vinflunine USP/EP/BP

1.3 CAS No.: 162652-95-1

1.4 CID: 6918295

1.5 EINECS(EC#): 1806241-263-5

1.6 Molecular Formula: C45H54F2N4O8 (isomer)

1.7 Inchi: InChI=1S/C45H54F2N4O8/c1-8-42-14-11-16-51-17-15-43(36(42)51)30-19-31(34(56-5)20-33(30)49(4)37(43)45(55,40(54)58-7)38(42)59-25(2)52)44(39(53)57-6)21-26-18-27(41(3,46)47)23-50(22-26)24-29-28-12-9-10-13-32(28)48-35(29)44/h9-14,19-20,26-27,36-38,48,55H,8,15-18,21-24H2,1-7H3/t26-,27-,36+,37-,38-,42-,43-,44+,45+/m1/s1

1.8 InChkey: NMDYYWFGPIMTKO-HBVLKOHWSA-N

1.9 Canonical Smiles: CCC12C=CCN3C1C4(CC3)C(C(C2OC(=O)C)(C(=O)OC)O)N(C5=CC(=C(C=C45)C6(CC7CC(CN(C7)CC8=C6NC9=CC=CC=C89)C(C)(F)F)C(=O)OC)OC)C

1.10 Isomers Smiles: CC[C@@]12C=CCN3[C@@H]1[C@]4(CC3)[C@H]([C@]([C@@H]2OC(=O)C)(C(=O)OC)O)N(C5=CC(=C(C=C45)[C@]6(C[C@H]7C[C@H](CN(C7)CC8=C6NC9=CC=CC=C89)C(C)(F)F)C(=O)OC)OC)C

2. Properties

2.1 Density: 1.39

2.1 Boiling point: °Cat760mmHg

2.1 Refractive index: 1.652

2.1 Flash Point: °C

2.1 Precise Quality: 816.39100

2.1 PSA: 133.87000

2.1 logP: 5.01950

2.1 pKa: 11.36±0.60(Predicted)

3. Use and Manufacturing

3.1 Definition: ChEBI: An organic heteropentacyclic compound and an organic heterotetracyclic compound that is vinorelbine in which the tetrahydropyridine moiety of the heterotetracyclic part of the molecule has been redced to the corresponding piperidine, and in which the ethy group attached to this ring has been replaced by a 1,1-difluoroethyl group.

4. 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

View all

5. NMR Spectrum

13C NMR : Predict

1H NMR : Predict

6. Synthesis Route

162652-95-1Total: 1 Synthesis Route

71486-22-1 128 Suppliers

162652-95-1 63 Suppliers

Literatures:
Fahy; Duflos; Ribet; Jacquesy; Berrier; Jouannetaud; Zunino Journal of the American Chemical Society, 1997 , vol. 119, # 36 p. 8576 - 8577
Yield: ~34%

7. Precursor and Product

precursor:

71486-22-1

8. Other Information

8.0 Use Classification: Human drugs -> Javlor -> EMA Drug Category|Antineoplastic agents -> Human pharmacotherapeutic group

8.1 Description: Vinflunine (also referred to as PM391) is a semisynthetic analog of the natural vinca alkaloids vinblastine and vincristine that was approved by the European Medicines Agency (EMEA) in 2009 for the treatment of adult patients with advanced or metastatic transitional cell carcinoma of the urothelial tract after failure of a prior platinum-containing regimen. Vinflunine is synthesized from anhydrovinblastine in a superacid media (HF-SbF₅) and in the presence of a chlorinated solvent like CHCl₃ or CCl₄.

8.2 Originator: Pierre Fabre (France)

8.3 Brand name: Javlor

8.4 Definition: ChEBI: An organic heteropentacyclic compound and an organic heterotetracyclic compound that is vinorelbine in which the tetrahydropyridine moiety of the heterotetracyclic part of the molecule has been redced to the corresponding piperidine, and in which the ethy group attached to this ring has been replaced by a 1,1-difluoroethyl group.

9. Computational chemical data

Molecular Weight: 816.944g/mol
Molecular Formula: C₄₅H₅₄F₂N₄O₈
Compound Is Canonicalized: True
XLogP3-AA: null
Exact Mass: 816.39097102
Monoisotopic Mass: 816.39097102
Complexity: 1720
Rotatable Bond Count: 10
Hydrogen Bond Donor Count: 2
Hydrogen Bond Acceptor Count: 13
Topological Polar Surface Area: 134
Heavy Atom Count: 59
Defined Atom Stereocenter Count: 9
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 1
CACTVS Substructure Key Fingerprint: AAADcfB/vYAAAAAAAAAAAAAAAAAAAWLFgAA8YMECAAAWAFix9AAAHwAQCAAAD3zhnhYyzvPJlgCoAyTyTAKCiCAhIiAImSF+bJgPJv7E9ZuGcChn8Bnb6Af62fOfqAACAgAKAABQgAYECBSgAAAAAAAAAA==

10. Recommended Suppliers

Global62SuppliersView all >>

Wuhan Fortuna Chemical Co., Ltd. Diamond member

-113YR

Products:API,fine chemical&its intermediates,biological chemistry
Tel:0086-27-59207850
Email:info@fortunachem.com

Vinflunine CAS 162652-95-1

Purity:99%Packing: 200kg/bag FOB
Price: 10 USD/kg
Time: 2023/06/05

Inquire

SN Biotechnology co. LTD Diamond member

-116YR

Products:Chemicals,Drugs ,Blotter ,Pill,Raw...
Tel:1-0-3137823697
Email:SROOCHEM@protonmail.com

Vinflunine

Purity:99%Packing: 200kg/bag FOB
Price: 1200 USD/kilogram
Time: 2023/04/27

Inquire

Amitychem Corporation Diamond member

-120YR

Products:Manufacture & Supply Biopharm Chemical, Specialty Chemical, PetroChemical.
Tel:86-592-8883942
Email:sale@amitychem.com

Factory Supply Vinflunine

Purity:99%Packing: 200kg/bag FOB
Price: 0.1 USD/kilogram
Time: 2023/03/01

Inquire

Jinlan Pharm-Drugs Technology Co., Limited Diamond member

-112YR

Products:Veterinary products,Nutrition products,Agrochemicals,Active pharmaceutical Ingredients,Custom systhesis,Contract manufacturing
Tel:86-571-85829052
Email:market@royalpharms.com

Aspidospermidine-3-carboxylicacid,4-(acetyloxy)-6,7-didehydro-15-[(2R,4R,6S,8S)-4-(1,1-difluoroethyl)-1,3,4,5,6,7,8,9-octahydro-8-(methoxycarbonyl)-2,6-methano-2H-azecino[4,3-b]indol-8-yl]-3-hydroxy-16-methoxy-1-methyl-,methyl ester, (2b,3b,4b,5a,12R,19a)-

Purity:99%Packing: 200kg/bag FOB
Price: 100 USD/kilogram
Time: 2023/05/31

Inquire

LUYUNJIA CHEMISTRY XIAMEN LIMITED Diamond member

-120YR

Products:o-Phthalaldehyde, Methoxyammonium chloride. DMSO, NMP,
Tel:86-592-5360779
Email:sales@luyunjiachem.com

Vinflunine

Purity:99%Packing: 200kg/bag FOB
Price:
Time: 2023/05/11

Inquire

11. Realated Product Infomation

194468-36-5 Vinflunine Ditartrate

Recently Updated : 1504534-66-0 1504543-42-3 150456-06-7 1504739-99-4 1504810-40-5 1504820-41-0 1504863-84-6 1504866-59-4 1504916-37-3 150493-05-3