3D Mol Similar

Vinorelbine

: CAS No.: 71486-22-1; Molecular Weight：778.947; Modify Date.: 2022-10-26 18:40; Introduction: Vinorelbine is a semisynthetic vinca alkaloid differing from vinblastine in the catharantinemoiety of the molecule. It is claimed to have a broad spectrum of action both in vifro andin vivo; clinically it has been found effective in the treatment of non-small cell lungcancer, advanced breast cancer, ovarian cancer and Hodgkins disease. View more+

Request For Quotation

1. Names and Identifiers

: 1.1 Name; Vinorelbine; 1.2 Synonyms; 3',4'-didehydro-4'-desoxy-8'-norvincaleucoblastine 3’,4’-didehydro-4’-deoxy-c’-norvincaleukoblastin 5-Nonylthio-8-methylthio-chinolin 5'-noranhydrovinblastine 8-methylsulfanyl-5-nonylsulfanyl-quinoline ANX-530, KW-2307, 5'-Noranhydrovinblastine AspidosperMidine-3-carboxylic acid, 4-(acetyloxy)-6,7-didehydro-15-[(2R,6R,8S)-4-ethyl-1,3,6,7,8 Aspidospermidine-3-carboxylic acid, 4-(acetyloxy)-6,7-didehydro-15-[(8S)-4-ethyl-1,3,6,7,8,9-hexahydro-8-(methoxycarbonyl)-2,6-methano-2H-azecino[4,3-b]indol-8-yl]-3-hydroxy-16-methoxy-1-methyl-, meth aspidospermidine-3-carboxylic acid, 4-(acetyloxy)-6,7-didehydro-15-[(8S)-4-ethyl-1,3,6,7,8,9-hexahydro-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)- CL069 CS-404 Methyl (2Β,3Β,4Β,5α,12Β,19α)-4-acetoxy-15-[(12S)-16-ethyl-12-(methoxycarbonyl)-1,10-diazatetracyclo[12.3.1.0.0]octadeca-3(11),4,6,8,15-pentaen-12-yl]-3-hydroxy-16-methox y-1-methyl-6,7-didehydroaspidospermidine-3-carboxylate Methyl (2Β,3Β,4Β,5α,12Β,19α)-4-acetoxy-15-[(12S)-16-ethyl-12-(methoxycarbonyl)-1,10-diazatetracyclo[12.3.1.0.0]octadeca-3(11),4,6,8,15-pentaen-12-yl]-3-hydroxy-16-methoxy-1-methyl-6,7-didehydroaspidospermidine-3-carboxylate nor-5’-anhydrovinblastine Quinoline,8-(methylthio)-5-(nonylthio) vinorebline vinorelbene vinorelbine D-tartrate yl ester, (2Β,3Β,4Β,5α,12Β,19α)-; View all

1.3 CAS No.: 71486-22-1

1.4 CID: 5672

1.5 Molecular Formula: C45H54N4O8 (isomer)

1.6 Inchi: InChI=1S/C45H54N4O8/c1-8-27-19-28-22-44(40(51)55-6,36-30(25-48(23-27)24-28)29-13-10-11-14-33(29)46-36)32-20-31-34(21-35(32)54-5)47(4)38-43(31)16-18-49-17-12-15-42(9-2,37(43)49)39(57-26(3)50)45(38,53)41(52)56-7/h10-15,19-21,28,37-39,46,53H,8-9,16-18,22-25H2,1-7H3

1.7 InChIkey: GBABOYUKABKIAF-UHFFFAOYSA-N

1.8 Canonical Smiles: CCC1=CC2CC(C3=C(CN(C2)C1)C4=CC=CC=C4N3)(C5=C(C=C6C(=C5)C78CCN9C7C(C=CC9)(C(C(C8N6C)(C(=O)OC)O)OC(=O)C)CC)OC)C(=O)OC

1.9 Isomers Smiles: CCC1=CC2CC(C3=C(CN(C2)C1)C4=CC=CC=C4N3)(C5=C(C=C6C(=C5)C78CCN9C7C(C=CC9)(C(C(C8N6C)(C(=O)OC)O)OC(=O)C)CC)OC)C(=O)OC

2. Properties

2.1 Density: 1.36

2.1 Refractive index: 1.676

2.1 Precise Quality: 778.39400

2.1 PSA: 133.87000

2.1 logP: 4.69440

2.1 Solubility: In water;, 8.37X10-3 mg/L at 25 deg C (est)

2.2 AnalyticLaboratory Methods: Analyte: vinorelbine tartrate; matrix: chemical identification; procedure: infrared absorption spectrophotometry with comparison to standards /vinorelbine tartrate/

2.3 Color/Form: Powder

2.4 pKa: 11.36±0.60(Predicted)

2.5 Water Solubility: In water;, 8.37X10-3 mg/L at 25 deg C (est)

2.6 Stability: Unopened vials of <a class="pubchem-internal-link multiple-CIDs" href="https://pubchem.ncbi.nlm.nih.gov/compound/vinorelbine%20tartrate">vinorelbine tartrate</a> injection are stable at temperatures up to 25 deg C for up to 72 hours. <a class="pubchem-internal-link multiple-CIDs" href="https://pubchem.ncbi.nlm.nih.gov/compound/Vinorelbine%20tartrate">Vinorelbine tartrate</a> injection should not be frozen.

3. Use and Manufacturing

3.1 Definition: ChEBI: A vinca alkaloid with a norvinblastine skeleton.

3.2 Methods of Manufacturing: ... A semisynthetic vinca alkaloid. Starting from <a class="pubchem-internal-link multiple-CIDs" href="https://pubchem.ncbi.nlm.nih.gov/compound/anhydrovinblastine">anhydrovinblastine</a> the compound is obtained as 5'-noranhydrovinblastine in three steps.

3.3 Usage: antimigraine, 5HT[1B/1D] agonist

4. Safety and Handling

4.1 Toxicity

CHEMICAL IDENTIFICATION

RTECS NUMBER :: RD2530000

CHEMICAL NAME :: C'-Norvincaleukoblastine, 3',4'-didehydro-4'-deoxy-

CAS REGISTRY NUMBER :: 71486-22-1

LAST UPDATED :: 199706

DATA ITEMS CITED :: 1

MOLECULAR FORMULA :: C45-H54-N4-O8

MOLECULAR WEIGHT :: 779.03

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 26 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: GTKRDX Gan to Kagaku Ryoho. Cancer and Chemotherapy. (1-8-9 Yaesu, Chuo-ku, Tokyo 103, Japan) V.1- 1974- Volume(issue)/page/year: 10,1050,1983

View all

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

View all

6. Synthesis Route

71486-22-1Total: 4 Synthesis Route

89384-09-8

71486-22-1 128 Suppliers

Literatures:
Gueritte; Pouilhes; Mangeney; et al. European Journal of Medicinal Chemistry, 1983 , vol. 18, # 5 p. 419 - 424
Yield: ~79%

89368-94-5

71486-22-1 128 Suppliers

Literatures:
Gueritte; Pouilhes; Mangeney; et al. European Journal of Medicinal Chemistry, 1983 , vol. 18, # 5 p. 419 - 424
Yield: ~77%

38390-45-3 61 Suppliers

71486-22-1 128 Suppliers

Literatures:
European Journal of Medicinal Chemistry, , vol. 18, # 5 p. 419 - 424
Yield: null

View all

7. Precursor and Product

precursor:

89384-09-8

89368-94-5

38390-45-3

product :

162652-95-1

8. Other Information

8.0 Description: Vinorelbine is a semisynthetic vinca alkaloid differing from vinblastine in the catharantine moiety of the molecule. It is claimed to have a broad spectrum of action both in vifro and in vivo; clinically it has been found effective in the treatment of non-small cell lung cancer, advanced breast cancer, ovarian cancer and Hodgkins disease.

8.1 Originator: CNRS (France)

8.2 Uses: antimigraine, 5HT[1B/1D] agonist

8.3 Uses: Vinorelbine base is an antineoplastic agent with anti-mitotic properties.

8.4 Definition: ChEBI: A vinca alkaloid with a norvinblastine skeleton.

8.5 Manufacturing Process: (+/-)-5-Ethyl-1,2,3,6-tetrahydro-pyridine-3-carboxylic acid ethyl ester and (+)-tartaric acid were dissolved in hot 95% ethanol. The resulting solution was allowed to slowly cool to room temperature and refrigerated overnight. The crystals were filtered, washed with cold ethanol, and recrystallized from 95% ethanol, cooling as before to give the (+)-tartrate salt of (+)-5-ethyl- 1,2,3,6-tetrahydro-pyridine-3-carboxylic acid ethyl ester.
The salt of (+)-5-ethyl-1,2,3,6-tetrahydro-pyridine-3-carboxylic acid ethyl ester was dissolved in on ice, and 3 N sodium hydroxide was slowly added until the pH reached 11-12. The solution was extracted with chloroform, dried (Na 2 SO 4 ) and evaporated in vacuum to give (+)-5-ethyl-1,2,3,6-tetrahydro- pyridine-3-carboxylic acid ethyl ester as a mobile oil.
Reduction of (+)-5-ethyl-1,2,3,6-tetrahydro-pyridine-3-carboxylic acid ethyl ester with LiAlH 4 in THF, using the usual protocols associated with this reagent gave the (+)-5-ethyl-1,2,3,6-tetrahydro-pyridine-3-ol. This material was used directly in the next step.
To a solution of the (+)-5-ethyl-1,2,3,6-tetrahydro-pyridine-3-ol in ethanol and triethylamine water, cooled equiv.) was added allyl bromide and the mixture heated at reflux for 12 h. The mixture was evaporated in vacuo and the residue dissolved in chloroform and washed with 5% aqueous K 2 CO 3 . The chloroform layer was dried (MgSO 4 ) and evaporated in vacuo to give the (+)- 1-allyl-5-ethyl-1,2,3,6-tetrahydro-pyridin-3-ol.
The (+)-1-allyl-5-ethyl-1,2,3,6-tetrahydro-pyridin-3-ol was converted into its methanesulfonate ester in the standard manner by treatment with methanesulfonic acid.
To a solution of the (+)-1-allyl-5-ethyl-1,2,3,6-tetrahydro-pyridin-3-methanesulfonate in acetone was added lithium bromide (6.9 g, 0.08 mol) and the suspension heated at reflux. The acetone was evaporated in vacuo, and the residue partitioned between chloroform and cold aqueous 5% K 2 CO 3 solution. The chloroform layer was dried (MgSO 4 ), filtered, and evaporated in vacuo to give a brown oil. Fractional distillation gave the (+)-1-allyl-5-ethyl- 1,2,3,6-tetrahydro-pyridin-3-bromide.
To a solution of N-phenylsulfonyl indole (5.14 g, 20 mmol) in dry THF (100 ml) under argon, and cooled to -65°C., was added t-butyl lithium (13 ml, 22 mmol, 1.7 M in pentane). The solution was allowed to warm to 0°C and stirred for 1 h. The above solution was added via canula to a stirred solution of dimethyloxalate (9.5 g, 80 mmol) in THF (250 ml) at 0°C. After 4 h at 0°C the mixture was quenched with saturated aqueous NH 4 Cl and extracted with ethyl acetate (3 times 100 ml). The dried (MgSO 4 ) extract was evaporated in vacuum, and the residue purified by chromatography over silica gel eluting with hexane/ethyl acetate (b 10:1) to give the N-phenylsulfonyl-2-methoxalyl indole (2.3 g, 34%). Melting point 111°-112°C (from ethyl acetate).
To the (+)-1-allyl-5-ethyl-1,2,3,6-tetrahydro-pyridin-3-bromide in a flame dried flask under argon was added Mg powder and dry THF. The mixture was heated at reflux and two drops of 1,2-dibromoethane added to initiate Grignard reagent formation. After 3 h the turbid suspension was cooled to room temperature and added to a solution of the N-phenylsulfonyl-2- methoxalyl indole in THF, at 0°C under argon. After 30 min the solution was quenched with saturated aqueous NH 4 Cl solution, and diluted with ethyl acetate. The dried (MgSO 4 ) extract was evaporated in vacuo to give the (+)- methyl 2-[2-(N-phenylsulfonyl)indolyl]-2-hydroxy-3-[3-(N-allyl 5-ethyl- 1,2,3,6-tetrahydro-peridine)]propionate consisting of a mixture of diastereomers at C-2 (1:1). For the purpose of characterization, one of the diastereomers was purified by chromatography over silica gel eluting with hexane/ethyl acetate/10% aqueous NH 4 OH/MeOH (15:3:1) to give the (+)- methyl 2-[2-(N-phenylsulfonyl)indolyl]-2-hydroxy-3-[3-(N-allyl-5-ethyl- 1,2,3,6-tetrahydro-pyridine)]propionate.
To a solution of the (+)-methyl 2-[2-(N-phenylsulfonyl)indolyl]-2-hydroxy-3- [3-(N-allyl-5-ethyl-1,2,3,6-tetrahydropyridine)]propionate (a mixture of diastereomers at C-2) in dry dimethoxyethane at -50°C under argon was added sodium naphthalenide (1 M in THF). The mixture was quenched with trifluoroacetic acid, and extracted with ethyl acetate (3 times 10 ml). The extract was washed with saturated aqueous NaHCO 3 solution, dried (MgSO 4 ) and evaporated in vacuo to give the (+)-methyl 2-(2-indolyl)-2-hydroxy-3-[3- (N-allyl-5-ethyl-1,2,3,6-tetrahydro-pyridine )]propionate. The mixture of diastereomers was not separated but chromotagraphed over silica gel eluting with hexane/ethyl acetate/10% aqueous NH 4 OH/MeOH (5:1:1) to remove more polar impurities.
A solution of the (+)-methyl 2-(2-indolyl)-2-hydroxy-3-[3-(N-allyl-5-ethyl- 1,2,3,6-tetrahydro-pyridine)]propionate (mixture of diastereomers), and vindoline in 1% HCl/MeOH was heated at reflux for 2 h. The solution was evaporated in vacuo and the residue dissolved in chloroform and washed with saturated aqueous NaHCO 3 solution. The chloroform layer was dried over MgSO 4 , filtered, and evaporated to give a foam consisting of a mixture of S-and R-diastereomers. The diastereomeric mixture was separated by preparative HPLC eluting with hexane/CH 2 Cl 2 /MeOH/10% aqueous NH 4 OH to give S-(+)-4-acethoxy-9-[2-(1-allyl-5-ethyl-1,2,3,6-tetrahydro-pyridin-3-yl)-1- (1H-indol-2-yl)-1-methoxycarbonyl-ethyl]-3a-ethyl-5-hydroxy-8-methoxy-6- methyl-3a,4,5,5a,6,11,12,12b-octahydro-1H-6,12a-diaza-indeno[7,1- ca]fluorene-5-carboxylic acid methyl ester.
The S-(+)-4-acethoxy-9-[2-(1-allyl-5-ethyl-1,2,3,6-tetrahydro-pyridin-3yl)-1- (1H-indol-2-yl)-1-methoxycarbonyl-ethyl]-3a-ethyl-5-hydroxy-8-methoxy-6- methyl-3a,4,5,5a,6,11,12,12b-octahydro-1H-6,12a-diaza-indeno[7,1- ca]fluorene-5-carboxylic acid methyl ester in 1,2-dichloroethane, containing proton sponge at 25°C, was treated with 1-chloroethyl chloroformate (0.056 ml, 0.512 mmol, 2.0 equiv.) and the resulting solution stirred for 3 h. The mixture was evaporated in vacuo, and the residue dissolved in methanol and heated at reflux for 3 h. The methanol was evaporated and the residue dissolved in chloroform and purified by chromatography over silica gel eluting with CHCl 3 , MeOH, 10% aqueous NH 4 OH (20:1) to give S-(+)-4-acethoxy-9- [2-(5-ethyl-1,2,3,6-tetrahydro-pyridin-3yl)-1-(1H-indol-2-yl)-1- methoxycarbonyl-ethyl]-3a-ethyl-5-hydroxy-8-methoxy-6-methyl- 3a,4,5,5a,6,11,12,12b-octahydro-1H-6,12a-diaza-indeno[7,1-ca]fluorene-5- carboxylic acid methyl ester.
To a solution of the S-(+)-4-acethoxy-9-[2-(5-ethyl-1,2,3,6-tetrahydro- pyridin-3yl)-1-(1H-indol-2-yl)-1-methoxycarbonyl-ethyl]-3a-ethyl-5-hydroxy- 8-methoxy-6-methyl-3a,4,5,5a,6,11,12,12b-octahydro-1H-6,12a-diaza- indeno[7,1-ca]fluorene-5-carboxylic acid methyl ester in dioxane and glacial acetic acid was added 37% aqueous formaldehyde and the mixture stirred at 35°C for 24 h. The solution was evaporated in vacuo and the residue suspended in chloroform and washed with cold aqueous 5% K 2 CO 3 solution. The chloroform layer was dried (MgSO 4 ), filtered, and evaporated. The residue was chromatographed eluting with EtOAc/MeOH, 10% NH 4 OH to give the product navelbine.; View all

8.6 Brand name: Navelbine (Pierre).

8.7 Therapeutic Function: Antineoplastic

8.8 Pharmacokinetics: This semisynthetic alkaloid is unique in having oral bioavailability, but it currently is available only for IV injection. The initial phase elimination half-life is on par with that observed for vincristine and vinblastine, and the terminal phase half-life is between 28 and 44 hours.

8.9 Clinical Use: Vinorelbine is particularly useful in the treatment of advanced non–small cell lung cancer and can be administered alone or in combination with cisplatin. It is thought to interfere with mitosis in dividing cells through a relatively specific action on mitotic microtubules.

8.10 Side effects: Although dose-limiting granulocytopenia is the major adverse effect, potentially fatal interstitial pulmonary changes have been noted, and patients with symptoms of respiratory distress should be promptly evaluated. As with all vinca alkaloids, elimination is primarily hepatobiliary, and dosage reduction should be considered in patients with liver dysfunction.

9. Computational chemical data

Molecular Weight: 778.947g/mol
Molecular Formula: C₄₅H₅₄N₄O₈
Compound Is Canonicalized: True
XLogP3-AA: null
Exact Mass: 778.39416469
Monoisotopic Mass: 778.39416469
Complexity: 1690
Rotatable Bond Count: 10
Hydrogen Bond Donor Count: 2
Hydrogen Bond Acceptor Count: 11
Topological Polar Surface Area: 134
Heavy Atom Count: 57
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 8
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 1
CACTVS Substructure Key Fingerprint: AAADcfB/vAAAAAAAAAAAAAAAAAAAAWLFgAAwYMECAAAWAFiB9AAAHgAQCAAAD3zhngYyzvPJlgCoAyTyTAKCiCAhIiAImSF+bJgPJv7E9ZuGcChn8Bnb6Af62fOfqAACAgAKAABQgAYECBSgAAAAAAAAAA==

10. Recommended Suppliers

Global126SuppliersView all >>

SN Biotechnology co. LTD Diamond member

7YRS

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

Vinorelbine

Purity:99%Packing: 200kg/bag FOB
Price: 1200 USD/kilogram
Time: 2023/07/19

Inquire

Dayang Chem (Hangzhou) Co., Ltd. Diamond member

12YRS

Products:Chemical products
Tel:86-571-88938639
Email:sales-gc@dycnchem.com

Vinorelbine

Purity:99%Packing: 200kg/bag FOB
Price: 2 USD/kilogram
Time: 2023/09/25

Inquire

Jilin Tely Imp & Exp Co., Ltd Audited Suppliers

Products:Pharmaceutical raw materials,Chemical reagent, Food aditives,Plant ExtracPharmaceutical and pesticide intermediates.
Tel:86-431-81915458

C-Norvincaleukoblastine, 3,4-didehydro-4-deoxy-

Purity:99%Packing: 200kg/bag FOB
Price: 1 USD/gram
Time: 2023/05/17

Inquire

Chengdu Gelipu Botechnology co.,ltd Audited Suppliers

Products:Specialize in fine chemicals,mainly manufacture pure botanical monomers ; Traditional Chinese Medicine references standards;Chemical reagents
Tel:86-28-82610909

Vinorelbine

Purity:99%Packing: 200kg/bag FOB
Price: 1 USD/20mg
Time: 2021/04/26

Inquire

Chengdu Herbpurify CO.,LTD Audited Suppliers

Products:phytochemicals; natural plant active ingredient monomer;reference standards of TCM(Traditional Chinese Medicine)
Tel:86-28-85249238

Vinorelbine

Purity:99%Packing: 200kg/bag FOB
Price: 1 USD/gram
Time: 2020/11/02

Inquire

11. Realated Product Infomation

125317-39-7 Vinorelbine tartrate

Recently Updated : 290835-10-8 474651-24-6 439132-47-5 477500-23-5 474881-86-2 887885-52-1 394231-77-7 394228-82-1 394226-03-0 887899-25-4