General
Preferred name
vincristine
Synonyms
Leurocristine sulfate ()
22-Oxovincaleukoblastine sulfate ()
Leurocristine ()
NSC-67574 ()
22-Oxovincaleukoblastine ()
Vincristine (sulfate) ()
Leurocristine (sulfate) ()
NSC-67574 (sulfate) ()
22-Oxovincaleukoblastine (sulfate) ()
VINCRISTINE SULFATE ()
P&D ID
PD003310
CAS
132142-73-5
57-22-7
2068-78-2
Tags
available
drug
Approved by
FDA
First approval
1963
Drug Status
approved
investigational
Structure
Probe scores
P&D probe-likeness score
[[ v.score ]]%
Structure formats
[[ format ]]
[[ compound[format === 'MOL' ? 'molblock' : format.toLowerCase()] ]]
Description
(extracted from source data)
HALF-LIFE When intravenously injected into cancer patients, a triphasic serum decay patten was observed. The initial, middle, and terminal half-lives are 5 minutes, 2.3 hours, 85 hours respectively. The range of the terminal half-life is humans is 19 - 155 hours.
PHARMACODYNAMICS 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.
MOA The antitumor activity of Vincristine is thought to be due primarily to inhibition of mitosis at metaphase through its interaction with tubulin. Like other vinca alkaloids, Vincristine may also interfere with: 1) amino acid, cyclic AMP, and glutathione metabolism, 2) calmodulin-dependent Ca2+-transport ATPase activity, 3) cellular respiration, and 4) nucleic acid and lipid biosynthesis.
INDICATION Treatment of acute lymphocytic leukemia (ALL), Hodgkin lymphoma, non-Hodgkin lymphomas, Wilms' tumor, neuroblastoma, rhabdomyosarcoma. Liposomal vincristine is indicated for the treatment of relapsed Philadelphia chromosome-negative (Ph-) acute lymphoblastic leukemia (ALL).
ROE The liver is the major excretory organ in humans and animals. 80% of an injected dose of vincristine sulfate is excreted via feces. 10 - 20% is excreted via urine.
TOXICITY IVN-RAT LD50 1300 mg/kg; IPR-MUS LD50 5.2 mg/kg. Marqibo® must only be administered IV because it is fatal if administered by other routes. Marqibo® also has different dosing than vincristine sulphate injection, so attention is needed to prevent overdoses. The most clinically significant adverse effect of vincristine is neurotoxicity.
METABOLISM Hepatic. Cytochrome P450 isoenzymes of the CYP3A subfamily facilitate the metabolism of vincristine.
PRICE 123
DESCRIPTION Vincristine sulfate is an antitumor vinca alkaloid which inhibits microtubule formation in mitotic spindle, resulting in an arrest of dividing cells at the metaphase stage. It binds to microtubule with a Ki of 85 nM.
DESCRIPTION inhibitor of mictrotubule assembly (Informer Set)
DESCRIPTION Vincristine binds to tubulin and inhibits the formation of microtubules, thereby inhibiting mitosis of the cancer cell. Vincristine can be used as a microtubule-destabilizing agent for research on the treatment of hematologic cancers, such as leukemia and (TargetMol Bioactive Compound Library)
DESCRIPTION Vincristine is an inhibitor of polymerization of microtubules by binding to tubulin with IC50 of 32 μM. (BOC Sciences Bioactive Compounds)
Compound Sets
16
BOC Sciences Bioactive Compounds
vincristine-cas-2068-78-2-item-84-333161
Cayman Chemical Bioactives
11764
CZ-OPENSCREEN Bioactive Library
Drug Repurposing Hub
DrugBank
DB00541
DrugBank Approved Drugs
DB00541
DrugCentral
2825
DrugCentral Approved Drugs
2825
EU-OPENSCREEN Bioactive Compound Library
EOS100001
Informer Set
62602
Mcule NIBR MoA Box Subset
MCULE-4345678378
MedChem Express Bioactive Compound Library
HY-N0488
NCATS Inxight Approved Drugs
5J49Q6B70F
NIH Clinical Collections (NCC)
Novartis Chemogenetic Library (NIBR MoA Box)
TargetMol Bioactive Compound Library
T3S0209
External IDs
39
Properties
(calculated by RDKit )
Molecular Weight
824.4
Hydrogen Bond Acceptors
12
Hydrogen Bond Donors
3
Rotatable Bonds
8
Ring Count
9
Aromatic Ring Count
3
cLogP
3.52
TPSA
171.17
Fraction CSP3
0.57
Chiral centers
10.0
Largest ring
9.0
QED
0.13
Structural alerts
0
No structural alerts detected
Related compounds
Custom attributes
(extracted from source data)
Compound status
FDA
Target
Microtubule/Tubulin
TUBA4A, TUBB
Apoptosis
Akt
ERK
JNK
MTOR
p38 MAPK
Pathway
Cell Cycle/DNA Damage
cytoskeleton
Cytoskeletal Signaling
MAPK
NF-κB
PI3K/Akt/mTOR signaling
Member status
virtual
MOA
binds to tubulin dmers leading to mitotic metaphase arrest
tubulin polymerization inhibitor
Indication
acute lymphoblastic leukemia (ALL)
Source data