Vindesine

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

MedKoo CAT#: 100921

CAS#: 53643-48-4

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.


Price and Availability

Size
Price

1g
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Size
Price

2g
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Size
Price

5g
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Vindesine is not in stock, may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 100921
Name: Vindesine
CAS#: 53643-48-4
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


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


Technical Data

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).

Harmonized System Code:
2934990300


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).
 
 


References

 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.