VINCRISTINE

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 Search

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

HIDE SMILES / InChI

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

Description
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

Approval Year

Targets

Primary Target	Pharmacology	Potency
transformed cell apoptotic process 104 Target ID: GO:0006927 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19137911	Activator 1447
Tubulin beta chain 8 Target ID: P07437 Gene ID: 203068.0 Gene Symbol: TUBB Target Organism: Homo sapiens (Human) Sources: http://www.drugbank.ca/drugs/DB00541	Inhibitor 8504
microtubule polymerization 21 Target ID: GO:0046785 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10920282	Inhibitor 8504	1.6 µM [IC50]
CCRF-CEM 4 Target ID: CHEMBL382 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22582991	Inhibitor 8504	0.17 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Philadelphia chromosome-negative (Ph-) acute lymphoblastic leukemia (ALL) in second or greater relapse 2 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2012/202497s000lbl.pdf	Primary		Approved 8583	Marqibo Approved Use Marqibo® 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 Date 2012

C_max

Value	Dose	Co-administered	Analyte	Population
1220 ng/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202497Orig1s000PharmR.pdf	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 DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202497Orig1s000PharmR.pdf	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

F_unbound

Value	Dose	Co-administered	Analyte	Population
25% OTHER GOV https://www.medsafe.govt.nz/profs/Datasheet/v/Vincristinesulfatempinj.pdf			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: https://pubmed.ncbi.nlm.nih.gov/19708032	unhealthy, 19-62 Health Status: unhealthy Age Group: 19-62 Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/19708032	Sources: https://pubmed.ncbi.nlm.nih.gov/19708032
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: https://pubmed.ncbi.nlm.nih.gov/19708032	unhealthy, 19-62 Health Status: unhealthy Age Group: 19-62 Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/19708032	DLT: Motor polyneuropathy, Seizure... Dose limiting toxicities: Motor polyneuropathy (grade 3, 14.3%) Seizure (grade 4, 14.3%) Hepatotoxicity (grade 4, 14.3%) Sources: https://pubmed.ncbi.nlm.nih.gov/19708032
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: https://pubmed.ncbi.nlm.nih.gov/10080616	unhealthy, 32-83 Health Status: unhealthy Age Group: 32-83 Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/10080616	DLT: Neutropenia, Thrombocytopenia... Dose limiting toxicities: Neutropenia (grade 4, 33.3%) Thrombocytopenia (grade 4, 33.3%) Obstipation Myalgia (grade 3, 33.3%) Sources: https://pubmed.ncbi.nlm.nih.gov/10080616
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: https://pubmed.ncbi.nlm.nih.gov/10080616	unhealthy, 32-83 Health Status: unhealthy Age Group: 32-83 Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/10080616	Sources: https://pubmed.ncbi.nlm.nih.gov/10080616
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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/202497s011lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/202497s011lbl.pdf	Disc. AE: Peripheral neuropathy, Tumor lysis syndrome... AEs leading to discontinuation/dose reduction: Peripheral neuropathy (10%) Tumor lysis syndrome (2%) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/202497s011lbl.pdf

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: https://pubmed.ncbi.nlm.nih.gov/19708032	unhealthy, 19-62 Health Status: unhealthy Age Group: 19-62 Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/19708032
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: https://pubmed.ncbi.nlm.nih.gov/19708032	unhealthy, 19-62 Health Status: unhealthy Age Group: 19-62 Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/19708032
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: https://pubmed.ncbi.nlm.nih.gov/19708032	unhealthy, 19-62 Health Status: unhealthy Age Group: 19-62 Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/19708032
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: https://pubmed.ncbi.nlm.nih.gov/10080616	unhealthy, 32-83 Health Status: unhealthy Age Group: 32-83 Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/10080616
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: https://pubmed.ncbi.nlm.nih.gov/10080616	unhealthy, 32-83 Health Status: unhealthy Age Group: 32-83 Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/10080616
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: https://pubmed.ncbi.nlm.nih.gov/10080616	unhealthy, 32-83 Health Status: unhealthy Age Group: 32-83 Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/10080616
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: https://pubmed.ncbi.nlm.nih.gov/10080616	unhealthy, 32-83 Health Status: unhealthy Age Group: 32-83 Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/10080616
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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/202497s011lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/202497s011lbl.pdf
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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/202497s011lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/202497s011lbl.pdf

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1946		substrate 1388	inhibitor 2217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	CYP2C19 1119 P-gp 2052

Drug as victim

Target	Modality	Activity	Clinical evidence
CYP2C19 1119	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202497Orig1s000ClinPharmR.pdf#page=31 Page: 31.0	likely
CYP2D6 1388	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202497Orig1s000ClinPharmR.pdf#page=31 Page: 31.0	likely
P-gp 2052	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/17029589/	yes
CYP3A4 1946	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202497Orig1s000ClinPharmR.pdf#page=31; https://pubmed.ncbi.nlm.nih.gov/10613614/ Page: 31.0	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) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202497Orig1s000ClinPharmR.pdf#page=31; https://pubmed.ncbi.nlm.nih.gov/10613614/ Page: 31.0

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2263	inhibitor 2237 Sources: https://pubmed.ncbi.nlm.nih.gov/15812674/ Page: 4.0

Sourcing

Vendor/Aggregator	ID	URL
AbovChem LLC	HY-N0488
AK Scientific	E375
Biopurify Phytochemicals	BP1439
Biopurify Phytochemicals	BP1440
BioSynth	Q-201925
BOC Sciences	2068-78-2
Bosche Scientific	V1207
Cayman Chemical	11764
Chem Scene	CS-1778
eMolecules	32176538
eMolecules	50241482
eMolecules	95704370
Hangzhou APIChem Technology	AC-22619
Hangzhou Yuhao Chemical Technology	RT14234
IBScreen	STOCK1N-40733
KeyOrganics	AS-12168
mcule	MCULE-1562099693
mcule	MCULE-3827132352
MedChem Express	HY-N0488
MolPort	MolPort-002-519-272
MolPort	MolPort-003-939-860
MolPort	MolPort-035-789-673
Sigma Aldrich	1714007
Sigma Aldrich	V0400000
Sigma Aldrich	V0400000\|SIAL
Sigma Aldrich	V8388\|SIAL
Sigma Aldrich	V8879\|SIGMA
ZINC	ZINC000085537024	http://zinc15.docking.org/substances/ZINC000085537024

PubMed

Title	Date	PubMed
Polymorphic variation in GSTP1 modulates outcome following therapy for multiple myeloma.	2003-10-01	12791655
Functional expression of the multidrug resistance protein 1 in microglia.	2003-10	12893836
Evidence for an antihyperalgesic effect of venlafaxine in vincristine-induced neuropathy in rat.	2003-08-01	12865165
[Anaphylaxia induced by etoposide--a case report].	2003-08	12938279
Henoch-Schönlein IgA glomerulonephritis complicating myeloma kidneys: case report.	2003-08	12844235
Synergistic augmentation of antimicrotubule agent-induced cytotoxicity by a phosphoinositide 3-kinase inhibitor in human malignant glioma cells.	2003-07-15	12874004
Spinal sensitization mechanism in vincristine-induced hyperalgesia in mice.	2003-06-05	12759171
Bilateral hearing loss during vincristine therapy: a case report.	2003-06	12868558
Charcot-Marie-Tooth disease and vincristine.	2003-05-21	12756314
The egr-1 gene is induced by DNA-damaging agents and non-genotoxic drugs in both normal and neoplastic human cells.	2003-05-16	12706485
Functional and structural consequences of cysteine substitutions in the NH2 proximal region of the human multidrug resistance protein 1 (MRP1/ABCC1).	2003-05-13	12731862
Changes in sensory processing in the spinal dorsal horn accompany vincristine-induced hyperalgesia and allodynia.	2003-05	12749967
Leiomyosarcoma of urinary bladder following cyclophosphamide therapy: report of two cases.	2003-05	12748258
Enteropathy-associated T-cell lymphoma of the jejunum complicated with intestinal perforation.	2003-04	12854879
[Clinical analysis of 75 patients with nasopharyngeal non-Hodgkin's lymphoma].	2003-04	12703998
Vincristine-induced neuropathy as the initial presentation of charcot-marie-tooth disease in acute lymphoblastic leukemia: a Pediatric Oncology Group study.	2003-04	12679647
Cloning and functional characterization of the multidrug resistance-associated protein (MRP1/ABCC1) from the cynomolgus monkey.	2003-03	12657726
Toxic neuropathy in patients with pre-existing neuropathy.	2003-01-28	12552058
NOVP chemotherapy for Hodgkin's disease transiently induces sperm aneuploidies associated with the major clinical aneuploidy syndromes involving chromosomes X, Y, 18, and 21.	2003-01-01	12517776
The effects of chemotherapeutic agents on the regulation of thrombin on cell surfaces.	2003-01	12542493
Vincristine neurotoxicity in the presence of hereditary neuropathy.	2003-01	12426685
A novel case of a CAT to AAT transversion in codon 179 of the p53 gene in a supratentorial primitive neuroectodermal tumor harbored by a young girl. Case report and review of the literature.	2003	12837982
Sexual dimorphism for protein kinase c epsilon signaling in a rat model of vincristine-induced painful peripheral neuropathy.	2003	12809704
Altered temporal pattern of evoked afferent activity in a rat model of vincristine-induced painful peripheral neuropathy.	2003	12710988
Posttransplantation lymphoproliferative disorder presenting as a unilateral leg mass 10 years after kidney transplantation.	2002-12-15	12490805
Evaluation of a 6-month chemotherapy protocol with no maintenance therapy for dogs with lymphoma.	2002-12-06	12465768
Epidemiology of Burkitt's lymphoma in Enugu, Nigeria.	2002-12	12530287
Identification and characterization of the canine multidrug resistance-associated protein.	2002-12	12516967
Treatment results of aggressive B non-Hodgkin's lymphoma in advanced age considering comorbidity.	2002-12	12437637
Hereditary neuropathy with liability to pressure palsies emerging during vincristine treatment.	2002-11-12	12427913
Vincristine-itraconazole interaction: cause for increasing concern.	2002-10	12368705
Pure red cell aplasia due to parvovirus following treatment with CHOP and rituximab for B-cell lymphoma.	2002-10	12358915
Gliomatosis cerebri: molecular pathology and clinical course.	2002-10	12325066
A case of treatment-related myelodysplastic syndrome and acute myelogenous leukemia following high-dose chemotherapy with autologous stem cell transplantation for non-Hodgkin's lymphoma.	2002-08	12172056
Reversible vincristine-related flaccid paralysis in a child with acute lymphoblastic leukemia.	2002-08	12116067
Functional analysis of MRP1 cloned from bovine.	2002-06-19	12067707
Hyponatremia and syndrome of inappropriate anti-diuretic hormone reported with the use of Vincristine: an over-representation of Asians?	2002-06-08	12051122
A prospective study of P-IMVP-16/CBDCA: a novel salvage chemotherapy for patients with aggressive non-Hodgkin's lymphoma who had previously received CHOP therapy as first-line chemotherapy.	2002-06	12225393
High-throughput measurement of the Tp53 response to anticancer drugs and random compounds using a stably integrated Tp53-responsive luciferase reporter.	2002-06	12082016
A phase II trial of combination chemotherapy and surgical resection for the treatment of metastatic adrenocortical carcinoma: continuous infusion doxorubicin, vincristine, and etoposide with daily mitotane as a P-glycoprotein antagonist.	2002-05-01	12015757
High-dose chemotherapy in poor-prognosis adult small round-cell tumors: clinical and molecular results from a prospective study.	2002-04-15	11956280
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	12401321
Effect of thiopental, propofol, and etomidate on vincristine toxicity in PC12 cells.	2002	11991087
Different peripheral mechanisms mediate enhanced nociception in metabolic/toxic and traumatic painful peripheral neuropathies in the rat.	2002	11983324
[An experimental study on the blood vessel sclerosing therapeutic agents for cavernous hemangiomas].	2001-08	12539736
Experience with vincristine--associated neurotoxicity.	2001-07	11957264
Vincristine neurotoxicity.	1992-03	1319399
Combined intra-arterial and systemic chemotherapy for recurrent malignant brain tumors.	1992-02	1312230
Fatal myeloencephalopathy due to intrathecal vincristine administration.	1992	1280054
Vincristine-induced myocardial infarction.	1975-12	1243105

Patents

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 Created by `admin` on `Mon Mar 31 17:34:32 GMT 2025` Edited by `admin` on `Mon Mar 31 17:34:32 GMT 2025`
Record UNII	5J49Q6B70F
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

TECNOCRIS

Preferred Name

English

VINCRISTINE

Official Name

English

(+)-VINCRISTINE

Common Name

English

22-OXOVINCALEUKOBLASTINE

Common Name

English

VINCALEUKOBLASTINE, 22-OXO-

Common Name

English

Vincristine [WHO-DD]

Common Name

English

ONCOTCS

Brand Name

English

VINCRISTINE [VANDF]

Common Name

English

VINCRISTINE [MI]

Common Name

English

VINCRISTINE [HSDB]

Common Name

English

VINKRISTIN

Common Name

English

VCR

Common Name

English

LEUROCRISTINE

Common Name

English

LEUCRISTINE

Common Name

English

vincristine [INN]

Common Name

English

VINCRISTIN

Common Name

English

Classification Tree Code System Code

WHO-VATC

QL01CA02