Vinblastine sulphate

Base Information

• Chemical Name: Vinblastine sulphate
• CAS No.: 143-67-9
• Molecular Formula: C46H58N4O9
• Molecular Weight: 810.988
• Hs Code.: 29399990
• European Community (EC) Number: 205-606-0
• UN Number: 2811
• NCI Thesaurus Code: C931
• RXCUI: 11199
• Mol file: 143-67-9.mol

Synonyms:cellblastin;Lemblastine;Sulfate, Vinblastine;Velban;Velbe;Vinblastin Hexal;Vinblastina Lilly;Vinblastine;Vinblastine Sulfate;Vinblastinsulfat-Gry;Vincaleukoblastine

Chemical Property of Vinblastine sulphate

Chemical Property:

• Appearance/Colour: crystalline solid
• Melting Point: 267°C (dec.)(lit.)
• PSA: 237.08000
• Density: 1.37 g/cm³
• LogP: 4.35970
• Storage Temp.: 2-8°C
• Solubility.: H2O: 10 mg/mL
• Water Solubility.: >=1 g/100 mL at 24.5 ºC
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 16
• Rotatable Bond Count: 10
• Exact Mass: 908.38775915
• Heavy Atom Count: 64
• Complexity: 1780
• Transport DOT Label: Poison

Purity/Quality:

99%, ^*data from raw suppliers

Vinblastine-d3 ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,T
• Hazard Codes: Xn,T
• Statements: 22-37/38-41-61-36/37/38-63-23/24/25
• Safety Statements: 26-36/39-53-45-37/39-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC1(CC2CC(C3=C(CCN(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)O.OS(=O)(=O)O
• Isomeric SMILES: CC[C@@]1(C[C@H]2C[C@@](C3=C(CCN(C2)C1)C4=CC=CC=C4N3)(C5=C(C=C6C(=C5)[C@@]78CCN9[C@H]7[C@@](C=CC9)([C@H]([C@@]([C@@H]8N6C)(C(=O)OC)O)OC(=O)C)CC)OC)C(=O)OC)O.OS(=O)(=O)O
• Recent ClinicalTrials: A Study to Compare Standard Therapy to Treat Hodgkin Lymphoma to the Use of Two Drugs, Brentuximab Vedotin and Nivolumab
• Recent EU Clinical Trials: LOGGIC/FIREFLY-2: A Phase 3, Randomized, International Multicenter Trial of DAY101 Monotherapy Versus Standard of Care Chemotherapy in Patients with Pediatric Low-Grade Glioma Harboring an Activating RAF Alteration Requiring First-Line Systemic Therapy
• Description: Vinblastine sulfate is the salt of an alkaloid extracted from Vinca rosea Linn., a common flowering herb known as the periwinkle (more properly known as Catharanthus roseus G. Don). Previously, the generic name was vincaleukoblastine, abbreviated VLB. It is a stathmokinetic oncolytic agent. When treated in vitro with this preparation, growing cells are arrested in metaphase. Chemical and physical evidence indicate that vinblastine sulfate is a dimeric alkaloid containing both indole and dihydroindole moieties.
• Uses: Anticancer agent; microtubule disrupter; Induces apoptosis.Vinblastine sulfate is therapeutically used as an antineoplastic. It is also used in the treatment of Hodgkin disease, choriocarcinoma, acute and chronic leukemias. Vinblastin sulfate USP (Velban) is used to treat Hodgkin’s disease; lymphosarcoma; reticulum cell sarcoma; neuroblastoma; choriocarcinoma; carcinoma of breast, lung, oral cavity, testis, bladder; acute and chronic leukemia; histiocytosis; mycosis fungoides.
• Therapeutic Function: Cancer chemotherapy
• Clinical Use: Vinblastine sulfate is available as a powder in 10-mg vials and as a solution in 10- and 25-mL vials for IV administrationin the treatment of various cancers including Hodgkin’sdisease, lymphocytic lymphoma, histiocytic lymphoma, advancedmycosis fungoides, advanced testicular carcinoma,and Kaposi sarcoma. It has also been used in treating choriocarcinomaand breast cancer when other therapies havefailed.
• Drug interactions: Potentially hazardous interactions with other drugs Aldesleukin: avoid concomitant use. Antibacterials: toxicity increased by erythromycin - avoid; possible increased risk of ventricular arrhythmias with delamanid. Antiepileptics: phenytoin levels may be reduced. Antifungals: possible increased risk of toxicity with itraconazole; metabolism possibly inhibited by posaconazole (increased risk of neurotoxicity). Antimalarials: avoid with piperaquine with artenimol. Antipsychotics: avoid with clozapine (increased risk of agranulocytosis).

Technology Process of Vinblastine sulphate

There total 9 articles about Vinblastine sulphate 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: 97.0%

→ vinblastine sulfate (143-67-9,18556-44-0,23624-16-0,64234-45-3,132142-72-4)

Guidance literature:

Reference yield: 89.0%

C46H54N4O9 → vinblastine (143-67-9)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol; at 20 ℃; for 0.75h;

DOI:10.1021/ol702040y

Reference yield: 50.0%

exo-catharanthine + vindoline (2182-14-1) → vinblastine (143-67-9)

Guidance literature:

exo-catharanthine; vindoline; With hydrogenchloride; iron(III) chloride; 2,2,2-trifluoroethanol; for 2h;

With sodium tetrahydroborate; oxygen; at 0 ℃; for 0.5h;

DOI:10.1039/c6sc00932h

upstream raw materials:

(+)-(9R)-3-oxo-9-methoxycarbonylindolizino<8,7-b>indole

vindoline

Downstream raw materials:

vindesine

12'-(4-trifluoromethylphenylamino)-3-(tert-butyl-dimethylsilanyloxy)vinblastine

12'-(4-methoxyphenylamino)-3-(tert-butyl-dimethylsilanyloxy)vinblastine

12'-(phenylamino)-3-(tert-butyl-dimethylsilanyloxy)vinblastine

Refernces

• 1、 Miyazaki, Tohru,Yokoshima, Satoshi,Simizu, Siro,Osada, Hiroyuki,Tokuyama, Hidetoshi,Fukuyama, Tohru. "Synthesis of (+)-vinblastine and its analogues". . p. 4737 - 4740. Retrieved 2008/03/15.