ContaminantDB: Vindesine

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (1)XML

Record Information

Version

1.0

Creation Date

2009-07-03 22:04:02 UTC

Update Date

2026-05-14 16:25:19 UTC

Accession Number

CHEM002062

Identification

Common Name

Vindesine

Class

Small Molecule

Description

Vindesine 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.

Contaminant Sources

HMDB Contaminants - Urine
T3DB toxins

Contaminant Type

Amide
Amine
Antineoplastic Agent
Antineoplastic Agent, Phytogenic
Drug
Ester
Ether
Human Neurotoxin
Metabolite
Organic Compound
Synthetic Compound
Tubulin Modulator

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
3-(Aminocarbonyl)-O(4)-deacetyl-3-de(methoxycarbonyl)vincaleukoblastine	ChEBI
3-Carbamoyl-4-deacetyl-3-de(methoxycarbonyl)vincaleukoblastine	ChEBI
Desacetylvinblastine amide	ChEBI
Desacetylvinblastine amide sulfate	HMDB
Vindesine sulfate	HMDB
Eldisine	HMDB
Compound 112531	HMDB
Enison	HMDB
Sulfate, vindesine	HMDB
EG labo brand OF vindesine sulfate	HMDB
Lilly brand OF vindesine sulfate	HMDB
Vindesin	HMDB

Chemical Formula

C₄₃H₅₅N₅O₇

Average Molecular Mass

753.926 g/mol

Monoisotopic Mass

753.410 g/mol

CAS Registry Number

53643-48-4

IUPAC Name

methyl (13S,15R,17S)-13-[(1R,9R,10S,11R,12R,19R)-10-carbamoyl-12-ethyl-10,11-dihydroxy-5-methoxy-8-methyl-8,16-diazapentacyclo[10.6.1.0^{1,9}.0^{2,7}.0^{16,19}]nonadeca-2,4,6,13-tetraen-4-yl]-17-ethyl-17-hydroxy-1,11-diazatetracyclo[13.3.1.0^{4,12}.0^{5,10}]nonadeca-4(12),5(10),6,8-tetraene-13-carboxylate

Traditional Name

vindesine

SMILES

[H][C@@]12N3CC[C@@]11C4=CC(=C(OC)C=C4N(C)[C@@]1([H])[C@](O)([C@H](O)[C@]2(CC)C=CC3)C(N)=O)[C@]1(C[C@]2([H])CN(C[C@](O)(CC)C2)CCC2=C1NC1=CC=CC=C21)C(=O)OC

InChI Identifier

InChI=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 Key

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.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Vinca alkaloids

Sub Class

Not Available

Direct Parent

Vinca 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 Framework

Aromatic heteropolycyclic compounds

External Descriptors

tertiary alcohol (CHEBI:36373 )
tertiary amino compound (CHEBI:36373 )
organic heterotetracyclic compound (CHEBI:36373 )
organic heteropentacyclic compound (CHEBI:36373 )
methyl ester (CHEBI:36373 )
carboxamide (CHEBI:36373 )
vinca alkaloid (CHEBI:36373 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

antineoplastic agent

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

Crystal from ethanol-methanol (8).

Experimental Properties

Property	Value
Melting Point	230-232°C
Boiling Point	Not Available
Solubility	7.00e-02 g/L

Predicted Properties

Property	Value	Source
Water Solubility	0.07 g/L	ALOGPS
logP	3.53	ALOGPS
logP	2.79	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	11.34	ChemAxon
pKa (Strongest Basic)	8.68	ChemAxon
Physiological Charge	2	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	164.82 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	210.32 m³·mol⁻¹	ChemAxon
Polarizability	82.58 Å³	ChemAxon
Number of Rings	9	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00dm-3000009300-920d08ee3b76aa4e7719	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_5) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_7) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_8) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_9) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_10) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_11) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_4) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_5) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-0zfr-0112112900-e3bfb9c4af77d4fe2af5	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-0udi-0000000900-cb4978163c559e621435	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-0udi-0000000900-64dc32fa5d65b3d42cb1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0f79-0000001900-369683957a66d70eebfa	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00n0-0112003900-58bf0ef72f9e97c44ec4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-3803009200-47cf947833663835e678	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0003004900-fa0b2d502bbde53f4eaa	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-052r-0009001100-d10caa1c9dc37de4234a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4m-0119008100-0235804cf191889cb491	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0000000900-63457808b4aff7f6cf2c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0pbd-0000009400-cd03418eb4ca2087871a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00ba-0030009000-aa689459a9c588c2bba1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0000001900-c44f712f9e0596530990	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0f9i-0000002900-5e868db73e2c319ef16d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0fc0-1000029000-58409a1c500bfb5266e4	Spectrum

Toxicity Profile

Route of Exposure

Ingestion, inhalation (7, 2).

Mechanism of Toxicity

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.

Metabolism

Hepatic Half Life: 24 hours.

Toxicity Values

LD50: 4 mg/kg (Mouse)

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

Vindesine is used in chemotherapy to treat many different types of cancer, including leukaemia, lymphoma, melanoma, breast cancer, and lung cancer (5).

Minimum Risk Level

Not Available

Health Effects

The bone marrow depressant effects of vindesine may result in an increased incidence of microbial infection, delayed healing, and gingival bleeding (3).

Symptoms

Not Available

Treatment

Activated 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. (7)

Concentrations

Not Available

External Links

DrugBank ID

DB00309

HMDB ID

HMDB0014454

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Chemspider ID

ChEBI ID

PubChem Compound ID

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

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

MSDS

Not Available

General References

Not Available

Vindesine (CHEM002062)

Structure for CHEM002062: Vindesine