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Details

Stereochemistry ABSOLUTE
Molecular Formula C46H56N4O10
Molecular Weight 824.9576
Optical Activity UNSPECIFIED
Defined Stereocenters 9 / 9
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of VINCRISTINE

SMILES

[H][C@@]12N3CC[C@@]14C5=CC(=C(OC)C=C5N(C=O)[C@@]4([H])[C@](O)([C@H](OC(C)=O)[C@]2(CC)C=CC3)C(=O)OC)[C@]6(C[C@H]7CN(C[C@](O)(CC)C7)CCC8=C6NC9=CC=CC=C89)C(=O)OC

InChI

InChIKey=OGWKCGZFUXNPDA-CFWMRBGOSA-N
InChI=1S/C46H56N4O10/c1-7-42(55)22-28-23-45(40(53)58-5,36-30(14-18-48(24-28)25-42)29-12-9-10-13-33(29)47-36)32-20-31-34(21-35(32)57-4)50(26-51)38-44(31)16-19-49-17-11-15-43(8-2,37(44)49)39(60-27(3)52)46(38,56)41(54)59-6/h9-13,15,20-21,26,28,37-39,47,55-56H,7-8,14,16-19,22-25H2,1-6H3/t28-,37-,38+,39+,42-,43+,44+,45-,46-/m0/s1

HIDE SMILES / InChI

Molecular Formula C46H56N4O10
Molecular Weight 824.9576
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 8 / 9
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

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. 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.Vincristine was marketed under the brand name Oncovin, but was discontinued. In 2012 the FDA approved a Liposomal formulation of Vincristine, named MARQIBO KIT.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
1.6 µM [IC50]
0.17 nM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Marqibo

Cmax

ValueDoseCo-administeredAnalytePopulation
1220 ng/mL
2.25 mg/m² steady-state, intravenous
VINCRISTINE plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
14566 ng × h/mL
2.25 mg/m² steady-state, intravenous
VINCRISTINE plasma
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
25%
VINCRISTINE plasma
Homo sapiens

Doses

AEs

Overview

OverviewOther

Other InhibitorOther SubstrateOther Inducer


Drug as victim

Tox targets

Sourcing

PubMed

Sample Use Guides

In Vivo Use Guide
Marqibo is liposome-encapsulated vincristine. 2.25 mg/m2 intravenously over 1 hour once every 7 days.
Route of Administration: Intravenous
In Vitro Use Guide
Treatment of macrophage monolayers for 24 h with vincristine (10(-5)-10(-7) M) inhibited the antibody dependent cellular cytotoxicity (ADCC) by PMA stimulated rat macrophages.
Substance Class Chemical
Record UNII
5J49Q6B70F
Record Status Validated (UNII)
Record Version