Tmic
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Record Information
Version2.0
Creation Date2009-07-03 22:04:02 UTC
Update Date2014-12-24 20:25:34 UTC
Accession NumberT3D2479
Identification
Common NameVindesine
ClassSmall Molecule
DescriptionVindesine is only found in individuals that have used or taken this drug. It is a vinblastine derivative with antineoplastic activity against cancer. Major side effects are myelosuppression and neurotoxicity. Vindesine is used extensively in chemotherapy protocols (antineoplastic combined chemotherapy protocols). Vindesine acts by causing the arrest of cells in metaphase mitosis through its inhibition tubulin mitotic funcitoning. The drug is cell-cycle specific for the S phase.
Compound Type
  • Amide
  • Amine
  • Antineoplastic Agent
  • Antineoplastic Agent, Phytogenic
  • Drug
  • Ester
  • Ether
  • Metabolite
  • Organic Compound
  • Synthetic Compound
  • Tubulin Modulator
Chemical Structure
Thumb
Synonyms
Synonym
3-(Aminocarbonyl)-O(4)-deacetyl-3-de(methoxycarbonyl)vincaleukoblastine
3-Carbamoyl-4-deacetyl-3-de(methoxycarbonyl)vincaleukoblastine
Desacetylvinblastine amide
Desacetylvinblastine Amide Sulfate
Eldesine
Eldisine
Vindesine Sulfate
Chemical FormulaC43H55N5O7
Average Molecular Mass753.926 g/mol
Monoisotopic Mass753.410 g/mol
CAS Registry Number53643-48-4
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[10.6.1.0¹,⁹.0²,⁷.0¹⁶,¹⁹]nonadeca-2,4,6,13-tetraen-4-yl]-17-ethyl-17-hydroxy-1,11-diazatetracyclo[13.3.1.0⁴,¹².0⁵,¹⁰]nonadeca-4(12),5,7,9-tetraene-13-carboxylate
Traditional Namevindesine
SMILES[H][C@@]12N(C)C3=CC(OC)=C(C=C3[C@@]11CCN3CC=C[C@](CC)([C@@]13[H])[C@@]([H])(O)[C@]2(O)C(O)=N)[C@]1(C[C@]2([H])CN(C[C@](O)(CC)C2)CCC2=C1NC1=CC=CC=C21)C(=O)OC
InChI IdentifierInChI=1S/C43H55N5O7/c1-6-39(52)21-25-22-42(38(51)55-5,33-27(13-17-47(23-25)24-39)26-11-8-9-12-30(26)45-33)29-19-28-31(20-32(29)54-4)46(3)35-41(28)15-18-48-16-10-14-40(7-2,34(41)48)36(49)43(35,53)37(44)50/h8-12,14,19-20,25,34-36,45,49,52-53H,6-7,13,15-18,21-24H2,1-5H3,(H2,44,50)/t25-,34+,35-,36-,39+,40-,41-,42+,43+/m1/s1
InChI KeyInChIKey=HHJUWIANJFBDHT-KOTLKJBCSA-N
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
Substituents
  • 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
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
Applications
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceCrystal from ethanol-methanol (6).
Experimental Properties
PropertyValue
Melting Point230-232°C
Boiling PointNot Available
Solubility7.00e-02 g/L
LogP2.9
Predicted Properties
PropertyValueSource
Water Solubility0.07 g/LALOGPS
logP3.53ALOGPS
logP2.79ChemAxon
logS-4ALOGPS
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00dm-3000009300-920d08ee3b76aa4e7719View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0zfr-0112112900-e3bfb9c4af77d4fe2af5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f79-0000001900-369683957a66d70eebfaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00n0-0112003900-58bf0ef72f9e97c44ec4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-3803009200-47cf947833663835e678View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0003004900-fa0b2d502bbde53f4eaaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-052r-0009001100-d10caa1c9dc37de4234aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4m-0119008100-0235804cf191889cb491View in MoNA
Toxicity Profile
Route of ExposureIngestion, inhalation (5, 2).
Mechanism of ToxicityVindesine acts by causing the arrest of cells in metaphase mitosis through its inhibition tubulin mitotic funcitoning. The drug is cell-cycle specific for the S phase.
MetabolismHepatic Half Life: 24 hours.
Toxicity ValuesLD50: 4 mg/kg (Mouse)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesVindesine is used in chemotherapy to treat many different types of cancer, including leukaemia, lymphoma, melanoma, breast cancer, and lung cancer (11).
Minimum Risk LevelNot Available
Health EffectsThe bone marrow depressant effects of vindesine may result in an increased incidence of microbial infection, delayed healing, and gingival bleeding (4).
SymptomsNot Available
TreatmentActivated charcoal binds most toxic agents and can decrease their systemic absorption if administered soon after ingestion. Immediate dilution with milk or water may be of benefit in caustic or irritant chemical ingestions. If the exposure occurred through inhalation, move patient to fresh air. Monitor for respiratory distress. If cough or difficulty breathing develops, evaluate for respiratory tract irritation, bronchitis, or pneumonitis. Administer oxygen and assist ventilation as required. Treat bronchospasm with inhaled beta2 agonist and oral or parenteral corticosteroids. in case of acute lung injury, Maintain ventilation and oxygenation and evaluate with frequent arterial blood gas or pulse oximetry monitoring. Following eye exposure, irrigate exposed eyes with copious amounts of room temperature water for at least 15 minutes. In case of dermal exposure, Remove contaminated clothing and wash exposed area thoroughly with soap and water. Treat dermal irritation or burns with standard topical therapy. Patients developing dermal hypersensitivity reactions may require treatment with systemic or topical corticosteroids or antihistamines. (5)
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDDB00309
HMDB IDHMDB14454
PubChem Compound ID40839
ChEMBL IDCHEMBL219146
ChemSpider ID37302
KEGG IDNot Available
UniProt IDNot Available
OMIM ID
ChEBI ID36373
BioCyc IDNot Available
CTD IDNot Available
Stitch IDVindesine
PDB IDNot Available
ACToR IDNot Available
Wikipedia LinkVindesine
References
Synthesis Reference

Stanislaw Rolski, “Method of preparing vindesine sulfate.” U.S. Patent US4259242, issued September, 1965.

MSDSNot Available
General References
  1. Wishart DS, Knox C, Guo AC, Cheng D, Shrivastava S, Tzur D, Gautam B, Hassanali M: DrugBank: a knowledgebase for drugs, drug actions and drug targets. Nucleic Acids Res. 2008 Jan;36(Database issue):D901-6. Epub 2007 Nov 29. [18048412 ]
  2. Zhang M, Hu P, Krois CR, Kane MA, Napoli JL: Altered vitamin A homeostasis and increased size and adiposity in the rdh1-null mouse. FASEB J. 2007 Sep;21(11):2886-96. Epub 2007 Apr 13. [17435174 ]
  3. Houghton LA, Vieth R: The case against ergocalciferol (vitamin D2) as a vitamin supplement. Am J Clin Nutr. 2006 Oct;84(4):694-7. [17023693 ]
  4. Nykjaer A, Dragun D, Walther D, Vorum H, Jacobsen C, Herz J, Melsen F, Christensen EI, Willnow TE: An endocytic pathway essential for renal uptake and activation of the steroid 25-(OH) vitamin D3. Cell. 1999 Feb 19;96(4):507-15. [10052453 ]
  5. Rumack BH (2009). POISINDEX(R) Information System. Englewood, CO: Micromedex, Inc. CCIS Volume 141, edition expires Aug, 2009.
  6. Budavari, S (ed) (1996). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc.
  7. Ellenhorn MJ, Schonwald S, Ordog G, Wasserberger J (1997). Ellenhorn's Medical Toxicology: Diagnosis and Treatment of Human Poisoning. 2nd ed. Baltimore, MD: Williams and Wilkins.
  8. MICROMEDEX Thomson Health Care (2001). USPDI - Drug Information for the Health Care Professional. 21st ed. Volume 1. Englewood, CO: MICROMEDEX Thomson Health Care. Content Reviewed and Approved by the U.S. Pharmacopeial Convention, Inc.
  9. Alper KR, Cordell GA, Brossi A, Manske RHF, Glick SD, Holmes HL, Rodrigo RGA, Suffness M. The Alkaloids. Ney York, NY: Academic Press.
  10. Dart RC (2003). Medical Toxicology. Philadelphia, PA: Lippincott Williams and Wilkins.
  11. Wikipedia. Vindesine. Last Updated 2 April 2009. [Link]
  12. Drugs.com [Link]
Gene Regulation
Up-Regulated Genes
GeneGene SymbolGene IDInteractionChromosomeDetails
Down-Regulated Genes
GeneGene SymbolGene IDInteractionChromosomeDetails

Targets

General Function:
Structural constituent of cytoskeleton
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 (By similarity).
Gene Name:
TUBB1
Uniprot ID:
Q9H4B7
Molecular Weight:
50326.56 Da
References
  1. Wishart DS, Knox C, Guo AC, Cheng D, Shrivastava S, Tzur D, Gautam B, Hassanali M: DrugBank: a knowledgebase for drugs, drug actions and drug targets. Nucleic Acids Res. 2008 Jan;36(Database issue):D901-6. Epub 2007 Nov 29. [18048412 ]
  2. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [17139284 ]
  3. 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. [17016423 ]