Vincristine

Base Information

• Chemical Name: Vincristine
• CAS No.: 57-22-7
• Molecular Formula: C46H56N4O10
• Molecular Weight: 824.971
• European Community (EC) Number: 200-318-1
• UN Number: 1544
• DSSTox Substance ID: DTXSID1032278
• Nikkaji Number: J10.132J
• Wikipedia: Vincristine
• Wikidata: Q408977
• NCI Thesaurus Code: C933
• RXCUI: 11202
• Pharos Ligand ID: 7L1XDD9J5DDK
• Metabolomics Workbench ID: 42878
• ChEMBL ID: CHEMBL90555
• Mol file: 57-22-7.mol

Synonyms:cellcristin;Citomid;Farmistin;Leurocristine;Oncovin;Oncovine;Onkocristin;PFS, Vincasar;Sulfate, Vincristine;Vincasar;Vincasar PFS;Vincristin Bristol;Vincristin medac;Vincristine;Vincristine Sulfate;Vincrisul;Vintec

Chemical Property of Vincristine

Chemical Property:

• Appearance/Colour: a white crystalline solid
• Melting Point: 211-216 °C
• Refractive Index: 1.677
• Boiling Point: 761.92°C (rough estimate)
• PKA: 5.4(at 25℃)
• PSA: 171.17000
• Density: 1.406 g/cm³
• LogP: 4.09420
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 12
• Rotatable Bond Count: 10
• Exact Mass: 824.39964400
• Heavy Atom Count: 60
• Complexity: 1750
• Transport DOT Label: Poison

Purity/Quality:

99% ^*data from raw suppliers

Vincristine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

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=O)(C(=O)OC)O)OC(=O)C)CC)OC)C(=O)OC)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=O)(C(=O)OC)O)OC(=O)C)CC)OC)C(=O)OC)O
• Recent ClinicalTrials: Irinotecan and Temozolomide in Combination With Existing High Dose Alkylator Based Chemotherapy for Treatment of Patients With Newly Diagnosed Ewing Sarcoma
• Recent EU Clinical Trials: A clinical trial in children and adolescents with primary malignant liver cancer - Hepatoblastoma and Hepatocarcinoma.
• Recent NIPH Clinical Trials: A Study of Ponatinib Versus Imatinib in Adults With Acute Lymphoblastic Leukemia
• Description: A complex dimeric alkaloid isolated from Vinca minor, this base has the structure given above based upon chemical and spectroscopic data. It resembles Vinblastine in its pharmacological action. Depending on the dosage, it causes either thrombocytosis with no effect upon the leucocytes, or thrombocytopenia accompanied by peucopenia in rats. Thrombocytosis persists even after prolonged treatment with drugs given in the correct dosage.
• Physical properties: Appearance: needlelike crystals were produced when recrystallized by methanol. The other properties of vincristine are similar to vinblastine.
• Uses: Antineoplastic[Note—Graphic formula same as for Vinblastine Sulfate, except that R is CHO].
• Indications: It was recorded in the Pharmacopoeia of the People’s Republic of China (2015), the British Pharmacopoeia (2017), the United States Pharmacopeia (40), the Japanese Pharmacopoeia (17th ed.), the European Pharmacopoeia (9th ed.), and The International Pharmacopoeia (5th ed.).Vincristine sulfate injection is used to treat leukemia, lymphadenoma, non-small cell lung cancer, nephroblastoma, and neuroblastoma in clinical practice generally, but the effect of vinblastine is better than vincristine in Hodgkin lymphoma treatment.
• Therapeutic Function: Cancer chemotherapy
• Clinical Use: Vincristine is an important component of the curative combination chemotherapy for acute lymphoblastic leukemia, Hodgkin’s disease (the MOPP regimen), and non-Hodgkin’s lymphomas. It is also used in several regimens for pediatric solid tumors, including Wilms’ tumor, Ewing’s sarcoma, rhabdomyosarcoma, and neuroblastoma; in adult tumors of the breast, lung, and cervix; and in sarcomas. Its relative lack of myelosuppression makes it more attractive than vinblastine for use in combination with myelotoxic drugs.Vinblastine is especially useful in testicular carcinomas and is also active in Hodgkin’s disease, other types of lymphomas, breast cancer, and renal cell carcinoma.

Technology Process of Vincristine

There total 3 articles about Vincristine 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: 98.0%

vincristine sulfate (2068-78-2) → Vincristine (57-22-7)

Guidance literature:

With sodium carbonate; In methanol; chloroform; water;

Reference yield: 79.0%

cyclovincristine (101156-38-1) → Vincristine (57-22-7)

Guidance literature:

With sodium tetrahydroborate; In dichloromethane; acetic acid; for 2h; Ambient temperature;

DOI:10.3987/com-98-s(h)25

Reference yield:

anhydrovinblastine (38390-45-3,56083-20-6,61246-76-2,105815-31-4) → Vincristine (57-22-7) + catharine + vinblastin (363623-08-9,906333-70-8) + vinleurosine (23360-92-1)

Guidance literature:

With cell-free extracts from Catharanthus roseus; Product distribution; Mechanism; Ambient temperature; biosynthesis of the products were studied; experiment was performed with 3',4'-anhydrovinblastine and the incorporation of the radiolabel into the products were investigated;

DOI:10.1002/hlca.19820650716

upstream raw materials:

anhydrovinblastine

cyclovincristine

vincristine sulfate

Downstream raw materials:

desacetylvincristine

Refernces

• 1、 -. "TREATMENT OF HYPERPROLIFERATIVE DISEASES WITH VINCA ALKALOID N-OXIDE AND ANALOGS". Page/Page column 46. . Retrieved 2008/06/13.