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
[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
| Molecular Formula | C46H56N4O10 |
| Molecular Weight | 824.9576 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 8 / 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
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: GO:0006927 |
|||
Target ID: P07437 Gene ID: 203068.0 Gene Symbol: TUBB Target Organism: Homo sapiens (Human) Sources: http://www.drugbank.ca/drugs/DB00541 |
|||
Target ID: GO:0046785 |
1.6 µM [IC50] | ||
Target ID: CHEMBL382 |
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 Co-administed with:: dexamethasone, i.v.(40 mg) Sources: Page: p.1,6 |
unhealthy, 19-62 n = 18 Health Status: unhealthy Condition: Acute lymphoblastic leukemia Age Group: 19-62 Sex: M+F Population Size: 18 Sources: Page: p.1,6 |
|
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 Co-administed with:: dexamethasone, i.v.(40 mg) Sources: Page: p.1,6 |
unhealthy, 19-62 n = 7 Health Status: unhealthy Condition: Acute lymphoblastic leukemia Age Group: 19-62 Sex: M+F Population Size: 7 Sources: Page: p.1,6 |
DLT: Motor polyneuropathy, Seizure... Dose limiting toxicities: Motor polyneuropathy (grade 3, 14.3%) Sources: Page: p.1,6Seizure (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: Page: p.701 |
unhealthy, 32-83 n = 3 Health Status: unhealthy Condition: Cancer Age Group: 32-83 Sex: M+F Population Size: 3 Sources: Page: p.701 |
DLT: Neutropenia, Thrombocytopenia... Dose limiting toxicities: Neutropenia (grade 4, 33.3%) Sources: Page: p.701Thrombocytopenia (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: Page: p.704 |
unhealthy, 32-83 n = 6 Health Status: unhealthy Condition: Cancer Age Group: 32-83 Sex: M+F Population Size: 6 Sources: Page: p.704 |
|
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: Page: p.8 |
unhealthy n = 83 Health Status: unhealthy Condition: Philadelphia chromosome-negative (Ph-) acute lymphoblastic leukemia (ALL) Population Size: 83 Sources: Page: p.8 |
Disc. AE: Peripheral neuropathy, Tumor lysis syndrome... AEs leading to discontinuation/dose reduction: Peripheral neuropathy (10%) Sources: Page: p.8Tumor 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 Co-administed with:: dexamethasone, i.v.(40 mg) Sources: Page: p.1,6 |
unhealthy, 19-62 n = 7 Health Status: unhealthy Condition: Acute lymphoblastic leukemia Age Group: 19-62 Sex: M+F Population Size: 7 Sources: Page: p.1,6 |
| 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 Co-administed with:: dexamethasone, i.v.(40 mg) Sources: Page: p.1,6 |
unhealthy, 19-62 n = 7 Health Status: unhealthy Condition: Acute lymphoblastic leukemia Age Group: 19-62 Sex: M+F Population Size: 7 Sources: Page: p.1,6 |
| 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 Co-administed with:: dexamethasone, i.v.(40 mg) Sources: Page: p.1,6 |
unhealthy, 19-62 n = 7 Health Status: unhealthy Condition: Acute lymphoblastic leukemia Age Group: 19-62 Sex: M+F Population Size: 7 Sources: Page: p.1,6 |
| 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: Page: p.701 |
unhealthy, 32-83 n = 3 Health Status: unhealthy Condition: Cancer Age Group: 32-83 Sex: M+F Population Size: 3 Sources: Page: p.701 |
| 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: Page: p.701 |
unhealthy, 32-83 n = 3 Health Status: unhealthy Condition: Cancer Age Group: 32-83 Sex: M+F Population Size: 3 Sources: Page: p.701 |
| 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: Page: p.701 |
unhealthy, 32-83 n = 3 Health Status: unhealthy Condition: Cancer Age Group: 32-83 Sex: M+F Population Size: 3 Sources: Page: p.701 |
| 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: Page: p.701 |
unhealthy, 32-83 n = 3 Health Status: unhealthy Condition: Cancer Age Group: 32-83 Sex: M+F Population Size: 3 Sources: Page: p.701 |
| 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: Page: p.8 |
unhealthy n = 83 Health Status: unhealthy Condition: Philadelphia chromosome-negative (Ph-) acute lymphoblastic leukemia (ALL) Population Size: 83 Sources: Page: p.8 |
| 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: Page: p.8 |
unhealthy n = 83 Health Status: unhealthy Condition: Philadelphia chromosome-negative (Ph-) acute lymphoblastic leukemia (ALL) Population Size: 83 Sources: Page: p.8 |
Overview
| CYP3A4 | CYP2C9 | CYP2D6 | hERG |
|---|---|---|---|
OverviewOther
| Other Inhibitor | Other Substrate | Other Inducer |
|---|---|---|
Drug as victim
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
| likely | ||||
| 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 |
|---|---|---|---|---|
Page: 4.0 |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Vincristine-induced myocardial infarction. | 1975 Dec |
|
| Vincristine-induced autonomic neuropathy. | 1975 Jul 26 |
|
| Fatal myeloencephalopathy due to intrathecal vincristine administration. | 1992 |
|
| Combined intra-arterial and systemic chemotherapy for recurrent malignant brain tumors. | 1992 Feb |
|
| Vincristine neurotoxicity. | 1992 Mar |
|
| Cyclophosphamide, doxorubicin, vincristine, prednisone, and etoposide (CHOPE) for advanced-stage Hodgkin's disease: CALGB 8856. | 2001 |
|
| Long-term follow-up in patients treated with Mini-BEAM as salvage therapy for relapsed or refractory Hodgkin's disease. | 2001 Apr |
|
| [An experimental study on the blood vessel sclerosing therapeutic agents for cavernous hemangiomas]. | 2001 Aug |
|
| Discovery of a novel compound: insight into mechanisms for acrylamide-induced axonopathy and colchicine-induced apoptotic neuronal cell death. | 2001 Aug 3 |
|
| Adult medulloblastoma: multiagent chemotherapy. | 2001 Jan |
|
| Treatment of classical type Kaposi's sarcoma with paclitaxel. | 2001 Jan-Feb |
|
| Evaluating treatment strategies in chronic lymphocytic leukemia: use of quality-adjusted survival analysis. | 2001 Jul |
|
| Itraconazole-enhanced vincristine neurotoxicity in a child with acute lymphoblastic leukemia. | 2001 Mar |
|
| Motor nervous pathway function is impaired after treatment of childhood acute lymphoblastic leukemia: a study with motor evoked potentials. | 2001 Mar |
|
| Ifosfamide and etoposide are superior to vincristine and melphalan for pediatric metastatic rhabdomyosarcoma when administered with irradiation and combination chemotherapy: a report from the Intergroup Rhabdomyosarcoma Study Group. | 2001 May |
|
| Mutation of a single conserved tryptophan in multidrug resistance protein 1 (MRP1/ABCC1) results in loss of drug resistance and selective loss of organic anion transport. | 2001 May 11 |
|
| 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 |
|
| Delayed functional recovery by vincristine after sciatic nerve crush injury: a mouse model of vincristine neurotoxicity. | 2001 May 18 |
|
| Fatal myeloencephalopathy due to accidental intrathecal vincristin administration: a report of two cases. | 2001 Oct 15 |
|
| 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 |
|
| Effect of thiopental, propofol, and etomidate on vincristine toxicity in PC12 cells. | 2002 |
|
| Hyponatremia and syndrome of inappropriate anti-diuretic hormone reported with the use of Vincristine: an over-representation of Asians? | 2002 Apr-May |
|
| Epidemiology of Burkitt's lymphoma in Enugu, Nigeria. | 2002 Dec |
|
| Identification and characterization of the canine multidrug resistance-associated protein. | 2002 Dec |
|
| Treatment results of aggressive B non-Hodgkin's lymphoma in advanced age considering comorbidity. | 2002 Dec |
|
| Posttransplantation lymphoproliferative disorder presenting as a unilateral leg mass 10 years after kidney transplantation. | 2002 Dec 15 |
|
| Vincristine-induced vocal cord paralysis in an infant. | 2002 Feb |
|
| Functional analysis of MRP1 cloned from bovine. | 2002 Jun 19 |
|
| Hereditary neuropathy with liability to pressure palsies emerging during vincristine treatment. | 2002 Nov 12 |
|
| Evaluation of a 6-month chemotherapy protocol with no maintenance therapy for dogs with lymphoma. | 2002 Nov-Dec |
|
| Vincristine-itraconazole interaction: cause for increasing concern. | 2002 Oct |
|
| Pure red cell aplasia due to parvovirus following treatment with CHOP and rituximab for B-cell lymphoma. | 2002 Oct |
|
| 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 |
|
| Altered temporal pattern of evoked afferent activity in a rat model of vincristine-induced painful peripheral neuropathy. | 2003 |
|
| Vincristine-induced neuropathy as the initial presentation of charcot-marie-tooth disease in acute lymphoblastic leukemia: a Pediatric Oncology Group study. | 2003 Apr |
|
| [Anaphylaxia induced by etoposide--a case report]. | 2003 Aug |
|
| Evidence for an antihyperalgesic effect of venlafaxine in vincristine-induced neuropathy in rat. | 2003 Aug 1 |
|
| The effects of chemotherapeutic agents on the regulation of thrombin on cell surfaces. | 2003 Jan |
|
| Vincristine neurotoxicity in the presence of hereditary neuropathy. | 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 |
|
| Toxic neuropathy in patients with pre-existing neuropathy. | 2003 Jan 28 |
|
| Spinal sensitization mechanism in vincristine-induced hyperalgesia in mice. | 2003 Jun 5 |
|
| Cloning and functional characterization of the multidrug resistance-associated protein (MRP1/ABCC1) from the cynomolgus monkey. | 2003 Mar |
|
| Changes in sensory processing in the spinal dorsal horn accompany vincristine-induced hyperalgesia and allodynia. | 2003 May |
|
| Leiomyosarcoma of urinary bladder following cyclophosphamide therapy: report of two cases. | 2003 May |
|
| Functional and structural consequences of cysteine substitutions in the NH2 proximal region of the human multidrug resistance protein 1 (MRP1/ABCC1). | 2003 May 13 |
|
| The egr-1 gene is induced by DNA-damaging agents and non-genotoxic drugs in both normal and neoplastic human cells. | 2003 May 16 |
|
| Charcot-Marie-Tooth disease and vincristine. | 2003 May-Jun |
|
| Functional expression of the multidrug resistance protein 1 in microglia. | 2003 Oct |
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
| Substance Class |
Chemical
Created
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5J49Q6B70F
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METABOLIC ENZYME -> 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 -> INHIBITOR | |||
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TRANSPORTER -> SUBSTRATE | |||
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TRANSPORTER -> SUBSTRATE |
Dogs homozygous or heterozygous for the ABCB1-1Δ mutation are significantly more likely than normal dogs to develop haematological and gastrointestinal toxicity.
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TRANSPORTER -> SUBSTRATE |
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MINOR
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ACTIVE MOIETY |
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| Route of Elimination | PHARMACOKINETIC |
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