Methyl 4-(acetyloxy)-15-[4-ethyl-8-(methoxycarbonyl)-1,3,6,7,8,9-hexahydro-2,6-methanoazecino[4,3-b]indol-8-yl]-3-hydroxy-16-methoxy-1-methyl-6,7-didehydroaspidospermidine-3-carboxylate

Base Information

• Chemical Name: Methyl 4-(acetyloxy)-15-[4-ethyl-8-(methoxycarbonyl)-1,3,6,7,8,9-hexahydro-2,6-methanoazecino[4,3-b]indol-8-yl]-3-hydroxy-16-methoxy-1-methyl-6,7-didehydroaspidospermidine-3-carboxylate
• CAS No.: 71486-22-1
• Molecular Formula: C45H54N4O8
• Molecular Weight: 778.946
• Hs Code.: 2939799090
• DSSTox Substance ID: DTXSID20860926
• Wikipedia: Vinorelbine
• Wikidata: Q27165488
• NCI Thesaurus Code: C1275
• RXCUI: 39541
• Mol file: 71486-22-1.mol

Synonyms:5' Nor anhydrovinblastine;5'-nor-anhydrovinblastine;KW 2307;KW-2307;KW2307;Navelbine;vinorelbine;vinorelbine tartrate

Chemical Property of Methyl 4-(acetyloxy)-15-[4-ethyl-8-(methoxycarbonyl)-1,3,6,7,8,9-hexahydro-2,6-methanoazecino[4,3-b]indol-8-yl]-3-hydroxy-16-methoxy-1-methyl-6,7-didehydroaspidospermidine-3-carboxylate

Chemical Property:

• Refractive Index: 1.676
• PKA: 11.36±0.60(Predicted)
• PSA: 133.87000
• Density: 1.36 g/cm³
• LogP: 4.69440
• XLogP3: 3.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 10
• Exact Mass: 778.39416469
• Heavy Atom Count: 57
• Complexity: 1690

Purity/Quality:

99%, ^*data from raw suppliers

Vinorelbine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• 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
• Recent ClinicalTrials: Tisotumab Vedotin vs Chemotherapy in Recurrent or Metastatic Cervical Cancer
• Recent EU Clinical Trials: Phase II Study of Neratinib and Trastuzumab +/- Vinorelbine p.o.
• Recent NIPH Clinical Trials: Phase II study of Platinum-Based Doublet Chemotherapy plus Atezolizumab, in completely resected, p-stage II-IIIA NSCLC patients harboring EGFR mutation. (WJOG11719L Investigator-Initiated Clinical Trial)
• 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.
• Uses: antimigraine, 5HT[1B/1D] agonist Vinorelbine base is an antineoplastic agent with anti-mitotic properties.
• Therapeutic Function: Antineoplastic
• 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.
• Drug interactions: Potentially hazardous interactions with other drugs Antibacterials: increased risk of neutropenia with clarithromycin; possible increased risk of ventricular arrhythmias with delamanid. Antifungals: metabolism possibly inhibited by itraconazole, increased risk of neurotoxicity. Antimalarials: avoid with piperaquine with artenimol. Antipsychotics: avoid concomitant use with clozapine (increased risk of agranulocytosis).

Technology Process of Methyl 4-(acetyloxy)-15-[4-ethyl-8-(methoxycarbonyl)-1,3,6,7,8,9-hexahydro-2,6-methanoazecino[4,3-b]indol-8-yl]-3-hydroxy-16-methoxy-1-methyl-6,7-didehydroaspidospermidine-3-carboxylate

There total 7 articles about Methyl 4-(acetyloxy)-15-[4-ethyl-8-(methoxycarbonyl)-1,3,6,7,8,9-hexahydro-2,6-methanoazecino[4,3-b]indol-8-yl]-3-hydroxy-16-methoxy-1-methyl-6,7-didehydroaspidospermidine-3-carboxylate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 80.0%

bromo-12 nor-5' anhydrovinblastine (89384-09-8) → nor-5' anhydrovinblastine (71486-22-1)

Guidance literature:

With tri-n-butyl-tin hydride; In methanol; for 2.5h; Irradiation;

Reference yield: 80.0%

C46H55BrN4O8 (89368-94-5) → nor-5' anhydrovinblastine (71486-22-1)

Guidance literature:

With silver tetrafluoroborate;

Reference yield: 75.0%

C46H55BrN4O8 (89368-94-5) → bromo-12 nor-5' anhydrovinblastine (89384-09-8) + nor-5' anhydrovinblastine (71486-22-1)

Guidance literature:

With silver tetrafluoroborate;

upstream raw materials:

bromo-12 nor-5' anhydrovinblastine

C₄₆H₅₅BrN₄O₈

anhydrovinblastine

chloro-7 indolenine de l' anhydrovinblastine

Downstream raw materials:

4-deacetyl-8'-noranhydrovinblastine

vinflunine

C₅₇H₆₈N₆O₁₁

Refernces

• 1、 -. "Therapeutic use of at least one botulinum neurotoxin in the treatment of pain induced by at least one anti-neoplastic agent". . . Retrieved 2010/04/23.
• 2、 -. "IMMUNOLIPOSOMES FOR TREATMENT OF CANCER". . . Retrieved 2010/10/03.