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Record Information
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:49 UTC
Update Date2020-02-26 21:39:42 UTC
Secondary Accession Numbers
  • HMDB14454
Metabolite Identification
Common NameVindesine
DescriptionVindesine, also known as vindesine sulfate or eldisine, belongs to the class of organic compounds known as vinca alkaloids. These are alkaloids with a dimeric chemical structure composed of an indole nucleus (catharanthine), and a dihydroindole nucleus (vindoline), joined together. Major side effects are myelosuppression and neurotoxicity. Vindesine is a drug which is used for the treatment of acute leukaemia, malignant lymphoma, hodgkin's disease, acute erythraemia and acute panmyelosis. Vindesine is a very strong basic compound (based on its pKa). Within humans, vindesine participates in a number of enzymatic reactions. In particular, vindesine can be converted into vindesine; which is mediated by the enzyme multidrug resistance-associated protein 7. In addition, vindesine can be converted into vindesine; which is catalyzed by the enzyme multidrug resistance-associated protein 1. Vindesine acts by causing the arrest of cells in metaphase mitosis through its inhibition tubulin mitotic funcitoning. In humans, vindesine is involved in vindesine action pathway. Vindesine is a potentially toxic compound. The drug is cell-cycle specific for the S phase.
Desacetylvinblastine amideChEBI
Desacetylvinblastine amide sulfateHMDB
Vindesine sulfateHMDB
Compound 112531HMDB
Sulfate, vindesineHMDB
EG labo brand OF vindesine sulfateHMDB
Lilly brand OF vindesine sulfateHMDB
Chemical FormulaC43H55N5O7
Average Molecular Weight753.9261
Monoisotopic Molecular Weight753.410149139
IUPAC Namemethyl (13S,15S,17S)-13-[(1R,9R,10S,11R,12R,19R)-10-carbamoyl-12-ethyl-10,11-dihydroxy-5-methoxy-8-methyl-8,16-diazapentacyclo[¹,⁹.0²,⁷.0¹⁶,¹⁹]nonadeca-2,4,6,13-tetraen-4-yl]-17-ethyl-17-hydroxy-1,11-diazatetracyclo[⁴,¹².0⁵,¹⁰]nonadeca-4(12),5,7,9-tetraene-13-carboxylate
Traditional Namevindesine
CAS Registry Number59917-39-4
InChI Identifier
Chemical Taxonomy
Description belongs to the class of organic compounds known as vinca alkaloids. These are alkaloids with a dimeric chemical structure composed of an indole nucleus (catharanthine), and a dihydroindole nucleus (vindoline), joined together.
KingdomOrganic compounds
Super ClassAlkaloids and derivatives
ClassVinca alkaloids
Sub ClassNot Available
Direct ParentVinca alkaloids
Alternative Parents
  • Vinca alkaloid skeleton
  • Carbazole
  • Quinoline-6-carboxamide
  • 3-alkylindole
  • Indole
  • Indole or derivatives
  • Anisole
  • Dialkylarylamine
  • Tertiary aliphatic/aromatic amine
  • Alkyl aryl ether
  • Aralkylamine
  • Piperidine
  • Benzenoid
  • N-alkylpyrrolidine
  • Cyclic alcohol
  • Heteroaromatic compound
  • Pyrrole
  • Pyrrolidine
  • Tertiary alcohol
  • Methyl ester
  • Tertiary aliphatic amine
  • Tertiary amine
  • Primary carboxylic acid amide
  • Amino acid or derivatives
  • Secondary alcohol
  • Carboxamide group
  • 1,2-aminoalcohol
  • Carboxylic acid ester
  • Azacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Ether
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Carbonyl group
  • Organopnictogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Alcohol
  • Organic nitrogen compound
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physiological effect

Health effect:


Route of exposure:

Biological location:


Naturally occurring process:


Biological role:

Industrial application:

Physical Properties
Experimental Properties
Melting Point230 - 232 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.07 g/LNot Available
LogP2.9Not Available
Predicted Properties
Water Solubility0.07 g/LALOGPS
pKa (Strongest Acidic)11.34ChemAxon
pKa (Strongest Basic)8.68ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area164.82 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity210.32 m³·mol⁻¹ChemAxon
Polarizability82.58 ųChemAxon
Number of Rings9ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00dm-3000009300-920d08ee3b76aa4e7719Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0zfr-0112112900-e3bfb9c4af77d4fe2af5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f79-0000001900-369683957a66d70eebfaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00n0-0112003900-58bf0ef72f9e97c44ec4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-3803009200-47cf947833663835e678Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0003004900-fa0b2d502bbde53f4eaaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-052r-0009001100-d10caa1c9dc37de4234aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4m-0119008100-0235804cf191889cb491Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Normal Concentrations
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00309 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00309 details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00309
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID37302
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkVindesine
METLIN IDNot Available
PubChem Compound40839
PDB IDNot Available
ChEBI ID36373
Food Biomarker OntologyNot Available
VMH IDNot Available
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available


General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:
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Molecular weight:
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
  2. Ekins S, Bravi G, Wikel JH, Wrighton SA: Three-dimensional-quantitative structure activity relationship analysis of cytochrome P-450 3A4 substrates. J Pharmacol Exp Ther. 1999 Oct;291(1):424-33. [PubMed:10490933 ]
General function:
Involved in structural molecule activity
Specific function:
Tubulin is the major constituent of microtubules. It binds two moles of GTP, one at an exchangeable site on the beta chain and one at a non-exchangeable site on the alpha-chain
Gene Name:
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Molecular weight:
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Natsume T, Watanabe J, Tamaoki S, Fujio N, Miyasaka K, Kobayashi M: Characterization of the interaction of TZT-1027, a potent antitumor agent, with tubulin. Jpn J Cancer Res. 2000 Jul;91(7):737-47. [PubMed:10920282 ]
  4. Yoshida M, Matsui Y, Ikarashi Y, Usui T, Osada H, Wakasugi H: Antiproliferating activity of the mitotic inhibitor pironetin against vindesine- and paclitaxel-resistant human small cell lung cancer H69 cells. Anticancer Res. 2007 Mar-Apr;27(2):729-36. [PubMed:17465195 ]
  5. Fiebig HH, Schuler J, Bausch N, Hofmann M, Metz T, Korrat A: Gene signatures developed from patient tumor explants grown in nude mice to predict tumor response to 11 cytotoxic drugs. Cancer Genomics Proteomics. 2007 May-Jun;4(3):197-209. [PubMed:17878523 ]