Vincristine

• Catalog No.: DB00541
• CAS Number: 57-22-7
• M. F.: C46H56N4O10
• M. W.: 824.95764

SYNONYMS

• IUPAC name: methyl (1R,9R,10S,11R,12R,19R)-11-(acetyloxy)-12-ethyl-4-[(13S,15S,17S)-17-ethyl-17-hydroxy-13-(methoxycarbonyl)-1,11-diazatetracyclo[13.3.1.0^{4,12}.0^{5,10}]nonadeca-4(12),5,7,9-tetraen-13-yl]-8-formyl-10-hydroxy-5-methoxy-8,16-diazapentacyclo[10.6.1.0^{1,9}.0^{2,7}.0^{16,19}]nonadeca-2(7),3,5,13-tetraene-10-carboxylate
• IUPAC Traditional name: sulfate, vincristine
• Brand Name: Vincasar PFS; Vinkristin; Oncovin; Vincasar; Vincrex; Vincristine Sulfate PFS; Marqibo; Onco TCS
• Synonyms: Vincristinum [INN-Latin]; VIN; Indole alkaloid; 22-Oxovincaleukoblastine; Vincristina [DCIT]; Vincrystine; Z-D-Val-Lys(Z)-OH; vincristine; VCR; LCR; Leurocristine; Vincristine Sulfate; Vincrstine

DATABASE IDS

• CAS Number: 57-22-7
• PubChem CID: 5978
• PubChem SID: 46507033

PROPERTIES

• Hydrophobicity(logP): 2.8

DETAILS

Description (English)

• Drug Groups: approved; investigational
• Description: Antitumor alkaloid isolated from Vinca Rosea. (Merck, 11th ed.)
• Indication: For treatment of acute leukaemia, malignant lymphoma, Hodgkin's disease, acute erythraemia, acute panmyelosis
• Pharmacology: Vincristine is a vinca alkaloid antineoplastic agent used as a treatment for various cancers including breast cancer, Hodgkin's disease, Kaposi's sarcoma, and testicular cancer. The vinca alkaloids are structurally similar compounds comprised of 2 multiringed units, vindoline and catharanthine. The vinca alkaloids have become clinically useful since the discovery of their antitumour properties in 1959. Initially, extracts of the periwinkle plant (Catharanthus roseus) were investigated because of putative hypoglycemic properties, but were noted to cause marrow suppression in rats and antileukemic effects in vitro. Vincristine binds to the microtubular proteins of the mitotic spindle, leading to crystallization of the microtubule and mitotic arrest or cell death. Vincristine has some immunosuppressant effect. The vinca alkaloids are considered to be cell cycle phase-specific.
• Toxicity: IVN-RAT LD₅₀ 1300 mg/kg; IPR-MUS LD₅₀ 5.2 mg/kg
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic
• Half Life: 19-155 hours
• Protein Binding: ~75%
• References: Graf WD, Chance PF, Lensch MW, Eng LJ, Lipe HP, Bird TD: Severe vincristine neuropathy in Charcot-Marie-Tooth disease type 1A. Cancer. 1996 Apr 1;77(7):1356-62. [Pubmed] ; Qweider M, Gilsbach JM, Rohde V: Inadvertent intrathecal vincristine administration: a neurosurgical emergency. Case report. J Neurosurg Spine. 2007 Mar;6(3):280-3. [Pubmed] ; JOHNSON IS, ARMSTRONG JG, GORMAN M, BURNETT JP Jr: THE VINCA ALKALOIDS: A NEW CLASS OF ONCOLYTIC AGENTS. Cancer Res. 1963 Sep;23:1390-427. [Pubmed]
• External Links: Wikipedia; RxList; Drugs.com

REFERENCES

• Graf WD, Chance PF, Lensch MW, Eng LJ, Lipe HP, Bird TD: Severe vincristine neuropathy in Charcot-Marie-Tooth disease type 1A. Cancer. 1996 Apr 1;77(7):1356-62. Pubmed
• Qweider M, Gilsbach JM, Rohde V: Inadvertent intrathecal vincristine administration: a neurosurgical emergency. Case report. J Neurosurg Spine. 2007 Mar;6(3):280-3. Pubmed
• JOHNSON IS, ARMSTRONG JG, GORMAN M, BURNETT JP Jr: THE VINCA ALKALOIDS: A NEW CLASS OF ONCOLYTIC AGENTS. Cancer Res. 1963 Sep;23:1390-427. Pubmed