WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 100921

CAS#: 53643-48-4 (free base)

Description: Vindesine is an anti-mitotic vinca alkaloid used in chemotherapy. It is used to treat many different types of cancer, including leukaemia, lymphoma, melanoma, breast cancer, and lung cancer.

Chemical Structure

CAS# 53643-48-4 (free base)

Theoretical Analysis

MedKoo Cat#: 100921
Name: Vindesine
CAS#: 53643-48-4 (free base)
Chemical Formula: C43H55N5O7
Exact Mass: 753.41015
Molecular Weight: 753.93
Elemental Analysis: C, 68.50; H, 7.35; N, 9.29; O, 14.86

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Related CAS #: 59917-39-4 (sulfate)   53643-48-4 (free base)  

Synonym: Compound 112531, deacetyl vinblastine carboxamide, desacetylvinblastine amide, Eldisine, DAVA, DVA, VDS, Lilly CT3231

IUPAC/Chemical Name: (3S,5S,7S,9S)-methyl 9-((3aR,3a1R,4R,5S,5aR,10bR)-5-carbamoyl-3a-ethyl-4,5-dihydroxy-8-methoxy-6-methyl-3a,3a1,4,5,5a,6,11,12-octahydro-1H-indolizino[8,1-cd]carbazol-9-yl)-5-ethyl-5-hydroxy-2,4,5,6,7,8,9,10-octahydro-1H-3,7-methano[1]azacycloundecino[5,4-b]indole-9-carboxylate


InChi Code: 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

SMILES Code: O=C([C@]1(C2=CC3=C(N(C)[C@@]4([H])[C@@](O)(C(N)=O)[C@H](O)[C@@]5(CC)[C@@]6([H])[C@]43CCN6CC=C5)C=C2OC)C[C@@]7([H])C[C@@](O)(CC)C[N@](C7)CCC8=C1NC9=C8C=CC=C9)OC

Appearance: White to off-white crystalline powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, not in water

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Preparing Stock Solutions

The following data is based on the product molecular weight 753.93 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL

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 1: Smith V, Dai F, Spitz M, Peters GJ, Fiebig HH, Hussain A, Burger AM. Telomerase activity and telomere length in human tumor cells with acquired resistance to anticancer agents. J Chemother. 2009 Nov;21(5):542-9. PubMed PMID: 19933046.

2: Takigawa N, Tanimoto M. [Vinca alkaloid and MDR1]. Gan To Kagaku Ryoho. 2008 Jul;35(7):1086-9. Japanese. PubMed PMID: 18633246.

3: Okamoto I. Overview of chemoradiation clinical trials for locally advanced non-small cell lung cancer in Japan. Int J Clin Oncol. 2008 Apr;13(2):112-6. Epub 2008 May 8. Review. PubMed PMID: 18463953.

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5: Chikamori M, Takigawa N, Kiura K, Tabata M, Shibayama T, Segawa Y, Ueoka H, Ohnoshi T, Tanimoto M. Establishment of a 7-ethyl-10-hydroxy-camptothecin-resistant small cell lung cancer cell line. Anticancer Res. 2004 Nov-Dec;24(6):3911-6. PubMed PMID: 15736431.

6: Kubota K, Watanabe K, Kunitoh H, Noda K, Ichinose Y, Katakami N, Sugiura T, Kawahara M, Yokoyama A, Yokota S, Yoneda S, Matsui K, Kudo S, Shibuya M, Isobe T, Segawa Y, Nishiwaki Y, Ohashi Y, Niitani H; Japanese Taxotere Lung Cancer Study Group. Phase III randomized trial of docetaxel plus cisplatin versus vindesine plus cisplatin in patients with stage IV non-small-cell lung cancer: the Japanese Taxotere Lung Cancer Study Group. J Clin Oncol. 2004 Jan 15;22(2):254-61. PubMed PMID: 14722033.

7: Sinha P, Poland J, Kohl S, Schnölzer M, Helmbach H, Hütter G, Lage H, Schadendorf D. Study of the development of chemoresistance in melanoma cell lines using proteome analysis. Electrophoresis. 2003 Jul;24(14):2386-404. PubMed PMID: 12874874.

8: Duflos A, Kruczynski A, Barret JM. Novel aspects of natural and modified vinca alkaloids. Curr Med Chem Anticancer Agents. 2002 Jan;2(1):55-70. Review. PubMed PMID: 12678751.

9: Prignano F, Coronnello M, Pimpinelli N, Cappugi P, Mini E, Giannotti B. Immunophenotypical markers, ultrastructure and chemosensitivity profile of metastatic melanoma cells. Cancer Lett. 2002 Dec 5;186(2):183-92. PubMed PMID: 12213288.

10: Poland J, Schadendorf D, Lage H, Schnölzer M, Celis JE, Sinha P. Study of therapy resistance in cancer cells with functional proteome analysis. Clin Chem Lab Med. 2002 Mar;40(3):221-34. Review. PubMed PMID: 12005211.

Additional Information

Vindesine is a synthetic derivative of vinblastine, a naturally occurring vinca alkaloid. Vindesine binds to and stabilizes tubulin, thereby interrupting tubulin polymerization and preventing the formation of the mitotic spindle and cell division; treated cells are unable to undergo mitosis and are arrested in metaphase. This agent also disrupts macromolecular synthesis. Check for active clinical trials or closed clinical trials using this agent. (NCI Thesaurus).