MedKoo Cat#: 100921 | Name: Vindesine

Description:

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

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

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

Theoretical Analysis

MedKoo Cat#: 100921

Name: Vindesine

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

Chemical Formula: C43H55N5O7

Exact Mass: 753.4102

Molecular Weight: 753.93

Elemental Analysis: C, 68.50; H, 7.35; N, 9.29; O, 14.86

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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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 Key
HHJUWIANJFBDHT-KOTLKJBCSA-N
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
More Info
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).    

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
 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. 4: Pearce HL, Alice Miller M. The evolution of cancer research and drug discovery at Lilly Research Laboratories. Adv Enzyme Regul. 2005;45:229-55. Epub 2005 Sep 6. PubMed PMID: 16143373. 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.