molecular formula C46H56N4O10 B1662923 Vincristin CAS No. 57-22-7

Vincristin

Katalognummer: B1662923
CAS-Nummer: 57-22-7
Molekulargewicht: 825.0 g/mol
InChI-Schlüssel: OGWKCGZFUXNPDA-DLBZMDDPSA-N
Achtung: Nur für Forschungszwecke. Nicht für den menschlichen oder tierärztlichen Gebrauch.
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Wirkmechanismus

Target of Action

Vincristine, a vinca alkaloid, primarily targets the protein tubulin, a key component of the microtubules in cells . Microtubules play a crucial role in maintaining cell structure and function, particularly during cell division .

Mode of Action

Vincristine binds to tubulin, inhibiting the polymerization of tubulin dimers and preventing the formation of microtubules . This interaction disrupts the formation of the mitotic spindle, a structure essential for chromosome separation during cell division . As a result, cells are arrested at metaphase, a stage in mitosis, leading to cell death .

Biochemical Pathways

The primary biochemical pathway affected by vincristine is the cell cycle, specifically the M and S phases . By disrupting microtubule dynamics, vincristine causes mitotic arrest, halting the cell cycle and leading to cell death . This disruption can also interfere with amino acid, cyclic AMP, and glutathione metabolism, as well as calmodulin-dependent Ca2±transport ATPase activity, and cellular respiration .

Pharmacokinetics

The pharmacokinetics of vincristine involve its absorption, distribution, metabolism, and excretion (ADME). Vincristine is administered intravenously, bypassing the absorption phase . It is metabolized primarily in the liver by the CYP3A5 enzyme . Vincristine’s neurotoxicity, a dose-limiting factor, is thought to be influenced by genetic variations in drug-metabolizing enzymes and transporters .

Result of Action

The molecular effect of vincristine’s action is the disruption of microtubule formation, leading to cell cycle arrest . On a cellular level, this results in the death of rapidly dividing cells, particularly cancer cells . This can also affect healthy cells, leading to side effects such as peripheral neuropathy .

Action Environment

Environmental factors can influence the action and efficacy of vincristine. For instance, the presence of other drugs used in combination therapies can impact vincristine’s effectiveness and toxicity profile . Additionally, genetic variations in patients can influence the drug’s metabolism and transport, potentially affecting its efficacy and toxicity .

Biochemische Analyse

Biochemical Properties

Vincristine is a vinca alkaloid that binds to the microtubular proteins of the mitotic spindle . This interaction leads to the 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 .

Cellular Effects

Vincristine works by stopping the cancer cells from separating into 2 new cells, thereby stopping the growth of the cancer . It achieves this through a process that disrupts the formation of microtubules, which affects cell division and eventually leads to apoptosis .

Molecular Mechanism

The molecular mechanism of Vincristine involves its binding to the tubulin protein, stopping the tubulin dimers from polymerizing to form microtubules . This causes the cell to be unable to separate its chromosomes during the metaphase . The cell then undergoes apoptosis . The vincristine molecule inhibits leukocyte production and maturation .

Temporal Effects in Laboratory Settings

It is known that within 15 to 30 minutes after injection, over 90% of the drug is distributed from the blood into tissue, where it remains tightly, but not irreversibly, bound .

Dosage Effects in Animal Models

In animal models, vincristine has shown high efficiency (86.6%) for treatment of transmissible venereal tumor in canines at the dose of 0.5 mg/m^2 of body surface (IV), on 7-14 days intervals . One tumor (6.6%) was refractory to vincristine, while at the treatment beginning a mass reduction was observed .

Metabolic Pathways

Vincristine may interfere with amino acid, cyclic AMP, and glutathione metabolism . It may also interfere with calmodulin-dependent Ca^2+ -transport ATPase activity, cellular respiration, and nucleic acid and lipid biosynthesis .

Transport and Distribution

Vincristine is transported and distributed within cells and tissues primarily through the bloodstream . It is given intravenously and can be administered through a drip into the arm or hand . Over 90% of the drug is distributed from the blood into tissue within 15 to 30 minutes after injection .

Subcellular Localization

The subcellular localization of Vincristine is primarily at the mitotic spindle, where it binds to the microtubular proteins . This binding leads to the crystallization of the microtubule and mitotic arrest or cell death .

Eigenschaften

CAS-Nummer

57-22-7

Molekularformel

C46H56N4O10

Molekulargewicht

825.0 g/mol

IUPAC-Name

methyl (10S,11R,12R)-11-acetyloxy-12-ethyl-4-[(13S,15S,17S)-17-ethyl-17-hydroxy-13-methoxycarbonyl-1,11-diazatetracyclo[13.3.1.04,12.05,10]nonadeca-4(12),5,7,9-tetraen-13-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

InChI

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+/m1/s1

InChI-Schlüssel

OGWKCGZFUXNPDA-DLBZMDDPSA-N

Verunreinigungen

3'-hydroxyvincristine;  4'-deoxyvincristine;  N-desmethylvinblastine;  deacetylvincristine;  deacetylvinblastine;  vinblastine;  leurosine;  formylleurosine

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

Isomerische SMILES

CC[C@@]1(C[C@@H]2C[C@@](C3=C(CCN(C2)C1)C4=CC=CC=C4N3)(C5=C(C=C6C(=C5)C78CCN9C7[C@@](C=CC9)([C@H]([C@@](C8N6C=O)(C(=O)OC)O)OC(=O)C)CC)OC)C(=O)OC)O

Kanonische 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

Aussehen

White to off-white, odorless amorphous or crystalline powder

Color/Form

Blades from methanol

melting_point

424 to 428 °F (NTP, 1992)
218-220 °C

57-22-7

Physikalische Beschreibung

Vincristine appears as a white crystalline solid. Melting point 218 °C. Used as an antineoplastic.

Haltbarkeit

STERILE SOLN IN EITHER H2O OR PHYSIOLOGICAL SALINE STORED IN REFRIGERATOR FOR UP TO 2 WK WITHOUT SIGNIFICANT LOSS OF POTENCY

Löslichkeit

WHITE TO SLIGHTLY YELLOW, AMORPHOUS OR CRYSTALLINE POWDER;  ODORLESS, HYGROSCOPIC;  FREELY SOL IN WATER /VINCRISTINE SULFATE USP/

Synonyme

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

Herkunft des Produkts

United States

Retrosynthesis Analysis

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Strategy Settings

Precursor scoring Relevance Heuristic
Min. plausibility 0.01
Model Template_relevance
Template Set Pistachio/Bkms_metabolic/Pistachio_ringbreaker/Reaxys/Reaxys_biocatalysis
Top-N result to add to graph 6

Feasible Synthetic Routes

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