Vincristine Sulfate
Generic: Vincristine
Medicinal Chemistry
Molecular Weight
923.04
Molecular Formula
C46H56N4O10.H2SO4
IUPAC Name
Methyl (1R,9R,10S,11R,12R,19R)-11-(acetyloxy)-12-ethyl-4-[(1S,3S,5S,9S)-5-ethyl-5-hydroxy-9-(methoxycarbonyl)-1,4,5,6,7,8,9,10-octahydro-2H-3,7-methanoazacycloundecino[5,4-b]indol-9-yl]-8-formyl-10-hydroxy-5-methoxy-8,16-diazapentacyclo[10.6.1.01,9.02,7.016,19]nonadeca-2,4,6,13-tetraene-10-carboxylate sulfate
Pharmacognosy
Biological Source
Catharanthus roseus (Madagascar Periwinkle)
Active Constituents
Vincristine, Vinblastine
Pharmacology & Synthesis
Mechanism of Action
Binds specifically to tubulin, inhibiting assembly of microtubules and arresting cells in metaphase.
Pharmacokinetics (ADME)
A: Administered IV only (fatal if given intrathecally).
D: Extensive tissue binding, poor BBB penetration.
M: Hepatic via CYP3A4.
E: Biliary and fecal.
Pharmacodynamics
Cytotoxic to rapidly dividing cells; highly effective in acute lymphoblastic leukemia (ALL).
Synthesis Pathway
Dimeric alkaloid formed naturally (N-methyl group of vindoline moiety replaced by an N-formyl group).
Safety, Warnings & Interactions
Adverse Effects
Peripheral neuropathy (dose-limiting), severe constipation, paralytic ileus, alopecia.
Contraindications
Charcot-Marie-Tooth syndrome, severe demyelinating conditions, intrathecal administration.
Drug Interactions
CYP3A4 inhibitors (itraconazole) increase severe neurotoxicity.
Pharmaceutics & Compendia
Dosage Forms
Injection (as Vincristine Sulfate)
Official Compendia
IP, BP, USP