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
SMILES
CC[C@]1(O)C[C@@H]2CN(C1)CCC3=C(NC4=C3C=CC=C4)[C@@](C2)(C(=O)OC)C5=C(OC)C=C6N(C=O)[C@@H]7[C@]8(CCN9CC=C[C@](CC)([C@@H]89)[C@@H](OC(C)=O)[C@]7(O)C(=O)OC)C6=C5
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
Molecular Formula | C46H56N4O10 |
Molecular Weight | 824.9576 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 9 / 9 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
DescriptionSources: http://www.drugbank.ca/drugs/DB00541Curator's Comment: Description was created based on several sources, including
https://www.drugs.com/pro/vincristine.html
Sources: http://www.drugbank.ca/drugs/DB00541
Curator's Comment: Description was created based on several sources, including
https://www.drugs.com/pro/vincristine.html
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
Sources: https://www.lilly.com/About/Heritage/heritage.aspx
Curator's Comment: # Dr. James. Armstrong of Eli Lilly and Company
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: GO:0006927 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19137911 |
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Target ID: P07437 Gene ID: 203068.0 Gene Symbol: TUBB Target Organism: Homo sapiens (Human) Sources: http://www.drugbank.ca/drugs/DB00541 |
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Target ID: GO:0046785 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10920282 |
1.6 µM [IC50] | ||
Target ID: CHEMBL382 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22582991 |
0.17 nM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Marqibo Approved UseMarqibo® is indicated for the treatment of adult patients with Philadelphia chromosome-negative (Ph-) acute
lymphoblastic leukemia (ALL) in second or greater relapse or whose disease has progressed following two or
more anti-leukemia therapies. Launch Date2012 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1220 ng/mL |
2.25 mg/m² steady-state, intravenous dose: 2.25 mg/m² route of administration: Intravenous experiment type: STEADY-STATE co-administered: |
VINCRISTINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
14566 ng × h/mL |
2.25 mg/m² steady-state, intravenous dose: 2.25 mg/m² route of administration: Intravenous experiment type: STEADY-STATE co-administered: |
VINCRISTINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
25% |
VINCRISTINE plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
2.25 mg/m2 1 times / week multiple, intravenous MTD Dose: 2.25 mg/m2, 1 times / week Route: intravenous Route: multiple Dose: 2.25 mg/m2, 1 times / week Sources: |
unhealthy, 19-62 |
|
2.4 mg/m2 1 times / week multiple, intravenous Studied dose Dose: 2.4 mg/m2, 1 times / week Route: intravenous Route: multiple Dose: 2.4 mg/m2, 1 times / week Sources: |
unhealthy, 19-62 |
DLT: Motor polyneuropathy, Seizure... Dose limiting toxicities: Motor polyneuropathy (grade 3, 14.3%) Sources: Seizure (grade 4, 14.3%) Hepatotoxicity (grade 4, 14.3%) |
2.8 mg/m2 3 times / week multiple, intravenous Highest studied dose Dose: 2.8 mg/m2, 3 times / week Route: intravenous Route: multiple Dose: 2.8 mg/m2, 3 times / week Sources: |
unhealthy, 32-83 |
DLT: Neutropenia, Thrombocytopenia... Dose limiting toxicities: Neutropenia (grade 4, 33.3%) Sources: Thrombocytopenia (grade 4, 33.3%) Obstipation Myalgia (grade 3, 33.3%) |
2.4 mg/m2 3 times / week multiple, intravenous MTD Dose: 2.4 mg/m2, 3 times / week Route: intravenous Route: multiple Dose: 2.4 mg/m2, 3 times / week Sources: |
unhealthy, 32-83 |
|
2.25 mg/m2 1 times / week multiple, intravenous Recommended Dose: 2.25 mg/m2, 1 times / week Route: intravenous Route: multiple Dose: 2.25 mg/m2, 1 times / week Sources: |
unhealthy Health Status: unhealthy Sources: |
Disc. AE: Peripheral neuropathy, Tumor lysis syndrome... AEs leading to discontinuation/dose reduction: Peripheral neuropathy (10%) Sources: Tumor lysis syndrome (2%) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Motor polyneuropathy | grade 3, 14.3% DLT |
2.4 mg/m2 1 times / week multiple, intravenous Studied dose Dose: 2.4 mg/m2, 1 times / week Route: intravenous Route: multiple Dose: 2.4 mg/m2, 1 times / week Sources: |
unhealthy, 19-62 |
Hepatotoxicity | grade 4, 14.3% DLT |
2.4 mg/m2 1 times / week multiple, intravenous Studied dose Dose: 2.4 mg/m2, 1 times / week Route: intravenous Route: multiple Dose: 2.4 mg/m2, 1 times / week Sources: |
unhealthy, 19-62 |
Seizure | grade 4, 14.3% DLT |
2.4 mg/m2 1 times / week multiple, intravenous Studied dose Dose: 2.4 mg/m2, 1 times / week Route: intravenous Route: multiple Dose: 2.4 mg/m2, 1 times / week Sources: |
unhealthy, 19-62 |
Obstipation | DLT | 2.8 mg/m2 3 times / week multiple, intravenous Highest studied dose Dose: 2.8 mg/m2, 3 times / week Route: intravenous Route: multiple Dose: 2.8 mg/m2, 3 times / week Sources: |
unhealthy, 32-83 |
Myalgia | grade 3, 33.3% DLT |
2.8 mg/m2 3 times / week multiple, intravenous Highest studied dose Dose: 2.8 mg/m2, 3 times / week Route: intravenous Route: multiple Dose: 2.8 mg/m2, 3 times / week Sources: |
unhealthy, 32-83 |
Neutropenia | grade 4, 33.3% DLT |
2.8 mg/m2 3 times / week multiple, intravenous Highest studied dose Dose: 2.8 mg/m2, 3 times / week Route: intravenous Route: multiple Dose: 2.8 mg/m2, 3 times / week Sources: |
unhealthy, 32-83 |
Thrombocytopenia | grade 4, 33.3% DLT |
2.8 mg/m2 3 times / week multiple, intravenous Highest studied dose Dose: 2.8 mg/m2, 3 times / week Route: intravenous Route: multiple Dose: 2.8 mg/m2, 3 times / week Sources: |
unhealthy, 32-83 |
Peripheral neuropathy | 10% Disc. AE |
2.25 mg/m2 1 times / week multiple, intravenous Recommended Dose: 2.25 mg/m2, 1 times / week Route: intravenous Route: multiple Dose: 2.25 mg/m2, 1 times / week Sources: |
unhealthy Health Status: unhealthy Sources: |
Tumor lysis syndrome | 2% Disc. AE |
2.25 mg/m2 1 times / week multiple, intravenous Recommended Dose: 2.25 mg/m2, 1 times / week Route: intravenous Route: multiple Dose: 2.25 mg/m2, 1 times / week Sources: |
unhealthy Health Status: unhealthy Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202497Orig1s000ClinPharmR.pdf#page=31 Page: 31.0 |
likely | |||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202497Orig1s000ClinPharmR.pdf#page=31 Page: 31.0 |
likely | |||
yes | ||||
yes | yes (co-administration study) Comment: the total area under the plasma concentration-time curve was 43% smaller in patients who were receiving carbamazepine or phenytoin than in the control group; the concomitant use of strong CYP3A inhibitors should be avoided (e.g., ketoconazole, itraconazole, voriconazole, posaconazole, clarithromycin, atazanavir, indinavir, nefazodone, nelfinavir, ritonavir, saquinavir, telithromycin). Similarly, the concomitant use of strong CYP3A inducers should be avoided (e.g., dexamethasone, phenytoin, carbamazepine, rifampin, rifabutin, rifapentine, phenobarbital, St. John’s Wort) Page: 31.0 |
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://pubmed.ncbi.nlm.nih.gov/15812674/ Page: 4.0 |
PubMed
Title | Date | PubMed |
---|---|---|
Vincristine-induced autonomic neuropathy. | 1975 Jul 26 |
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Altered expression of the MYCN oncogene modulates MRP gene expression and response to cytotoxic drugs in neuroblastoma cells. | 1999 Apr 29 |
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Pain related behaviour during vincristine-induced neuropathy in rats. | 1999 Apr 6 |
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Vincristine revisited. | 1999 Feb |
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[Acute vincristine neurotoxicity in a non-Hodgkin's lymphoma patient with Charcot-Marie-Tooth disease]. | 1999 May |
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Vincristine treatment revealing asymptomatic hereditary motor sensory neuropathy type 1A. | 1999 Nov |
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Nerve growth factor prevention of aged-rat sympathetic neuron injury by cisplatin, vincristine and taxol--in vitro explant study. | 1999 Oct 22 |
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Bilateral transient hearing loss associated with vincristine therapy: case report. | 2000 Dec |
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[Syndrome of inappropriate secretion of antidiuretic hormone in a patient with myeloid antigen positive acute lymphoblastic leukemia after systemic chemotherapy including vincristine]. | 2000 Jan |
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[Establishment of MRP-overexpression subline of bladder carcinoma and its MDR phenotype]. | 2000 Jul |
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Phase II trial of bryostatin 1 in patients with relapsed low-grade non-Hodgkin's lymphoma and chronic lymphocytic leukemia. | 2000 Mar |
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Cyclophosphamide, doxorubicin, vincristine, prednisone, and etoposide (CHOPE) for advanced-stage Hodgkin's disease: CALGB 8856. | 2001 |
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Discovery of a novel compound: insight into mechanisms for acrylamide-induced axonopathy and colchicine-induced apoptotic neuronal cell death. | 2001 Aug 3 |
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Experience with vincristine--associated neurotoxicity. | 2001 Jul |
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Evaluating treatment strategies in chronic lymphocytic leukemia: use of quality-adjusted survival analysis. | 2001 Jul |
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Itraconazole-enhanced vincristine neurotoxicity in a child with acute lymphoblastic leukemia. | 2001 Mar |
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ChlVPP alternating with PABlOE is superior to PABlOE alone in the initial treatment of advanced Hodgkin's disease: results of a British National Lymphoma Investigation/Central Lymphoma Group randomized controlled trial. | 2001 May 18 |
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Delayed functional recovery by vincristine after sciatic nerve crush injury: a mouse model of vincristine neurotoxicity. | 2001 May 18 |
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Ischemic heart disease associated with vincristine and doxorubicin chemotherapy. | 2001 Nov |
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Fatal myeloencephalopathy due to accidental intrathecal vincristin administration: a report of two cases. | 2001 Oct 15 |
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Inhibition of drug-induced Fas ligand transcription and apoptosis by Bcl-XL. | 2001 Sep |
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Massive cell death of cerebellar granule neurons accompanied with caspase-3-like protease activation and subsequent motor discoordination after intracerebroventricular injection of vincristine in mice. | 2002 |
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Effect of thiopental, propofol, and etomidate on vincristine toxicity in PC12 cells. | 2002 |
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High-dose chemotherapy in poor-prognosis adult small round-cell tumors: clinical and molecular results from a prospective study. | 2002 Apr 15 |
|
Epidemiology of Burkitt's lymphoma in Enugu, Nigeria. | 2002 Dec |
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Posttransplantation lymphoproliferative disorder presenting as a unilateral leg mass 10 years after kidney transplantation. | 2002 Dec 15 |
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High-throughput measurement of the Tp53 response to anticancer drugs and random compounds using a stably integrated Tp53-responsive luciferase reporter. | 2002 Jun |
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Improvement of combination chemotherapy tolerance by introduction of polycistronic retroviral vector drug resistance genes MGMT and MDR1 into human umbilical cord blood CD34+ cells. | 2002 Mar |
|
Gliomatosis cerebri: molecular pathology and clinical course. | 2002 Oct |
|
Sexual dimorphism for protein kinase c epsilon signaling in a rat model of vincristine-induced painful peripheral neuropathy. | 2003 |
|
The effects of chemotherapeutic agents on the regulation of thrombin on cell surfaces. | 2003 Jan |
|
NOVP chemotherapy for Hodgkin's disease transiently induces sperm aneuploidies associated with the major clinical aneuploidy syndromes involving chromosomes X, Y, 18, and 21. | 2003 Jan 1 |
|
Synergistic augmentation of antimicrotubule agent-induced cytotoxicity by a phosphoinositide 3-kinase inhibitor in human malignant glioma cells. | 2003 Jul 15 |
|
Charcot-Marie-Tooth disease and vincristine. | 2003 May-Jun |
Patents
Sample Use Guides
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/2846149
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
Created
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Record UNII |
5J49Q6B70F
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Record Status |
Validated (UNII)
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L01CA02
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8.2
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N0000007780
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N0000007780
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C67422
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NDF-RT |
N0000175612
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DB00541
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CHEMBL90555
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m11453
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C933
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VINCRISTINE
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Vincristine
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Related Record | Type | Details | ||
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METABOLIC ENZYME -> SUBSTRATE | |||
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TRANSPORTER -> SUBSTRATE | |||
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TRANSPORTER -> SUBSTRATE | |||
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TRANSPORTER -> SUBSTRATE | |||
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METABOLIC ENZYME -> SUBSTRATE |
CYP3A5 was more efficient in catalyzing the formation of M1 compared with CYP3A4 (9- to 14-fold higher intrinsic clearance for CYP3A5).
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TRANSPORTER -> SUBSTRATE | |||
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TRANSPORTER -> INHIBITOR | |||
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TRANSPORTER -> SUBSTRATE |
Dogs homozygous or heterozygous for the ABCB1-1? mutation are significantly more likely than normal dogs to develop haematological and gastrointestinal toxicity.
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TRANSPORTER -> INHIBITOR | |||
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TARGET -> INHIBITOR | |||
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SALT/SOLVATE -> PARENT |
Related Record | Type | Details | ||
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METABOLITE -> PARENT |
MINOR
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Related Record | Type | Details | ||
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ACTIVE MOIETY |
Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Route of Elimination | PHARMACOKINETIC |
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Route of Elimination | PHARMACOKINETIC |
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Biological Half-life | PHARMACOKINETIC |
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