Vinfosiltine

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MedKoo CAT#: 461608

CAS#: 123286-00-0

Description: Vinfosiltine is an antineoplastic agent which belongs to the vinca alkaloid group incorporating an amino-phosphonate.


Price and Availability

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Pricing updated 2020-07-14. Prices are subject to change without notice.

Vinfosiltine 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#: 461608
Name: Vinfosiltine
CAS#: 123286-00-0
Chemical Formula: C51H72N5O10P
Exact Mass: 945.5017
Molecular Weight: 946.13
Elemental Analysis: C, 64.74; H, 7.67; N, 7.40; O, 16.91; P, 3.27


Synonym: Vinfosiltine; S12363; S 12363; S-12363;

IUPAC/Chemical Name: methyl (5S,7R,9S)-9-((3aR,3a1R,4R,5S,5aR,10bR)-5-(((S)-1-(diethoxyphosphoryl)-2-methylpropyl)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-1,4,5,6,7,8,9,10-octahydro-2H-3,7-methano[1]azacycloundecino[5,4-b]indole-9-carboxylate

InChi Key: BOELCLFVOBIXIF-MAKKXPIGSA-N

InChi Code: InChI=1S/C51H72N5O10P/c1-10-47(60)27-32-28-50(46(59)64-9,40-34(19-23-55(29-32)30-47)33-17-14-15-18-37(33)52-40)36-25-35-38(26-39(36)63-8)54(7)43-49(35)21-24-56-22-16-20-48(11-2,42(49)56)44(57)51(43,61)45(58)53-41(31(5)6)67(62,65-12-3)66-13-4/h14-18,20,25-26,31-32,41-44,52,57,60-61H,10-13,19,21-24,27-30H2,1-9H3,(H,53,58)/t32-,41-,42-,43+,44+,47-,48+,49+,50-,51-/m0/s1

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


Technical Data

Appearance:
Solid 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

Shelf Life:
>3 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:
2934.99.03.00


References

1: Pierré A, Kraus-Berthier L, Atassi G, Cros S, Poupon MF, Lavielle G, Berlion M, Bizzari JP. Preclinical antitumor activity of a new Vinca alkaloid derivative, S 12363. Cancer Res. 1991 May 1;51(9):2312-8. PubMed PMID: 2015595.

2: Wright M, Garès M, Verdier-Pinard P, Moisand A, Berlion M, Legrand JJ, Bizzari JP. Differential in vitro action of S-12363, a new vinblastine derivative, and of its epimer on microtubule proteins. Cancer Chemother Pharmacol. 1991;28(6):434-40. PubMed PMID: 1934248.

3: Berlion M, Arvelo F, Leonce S, Bourgeois Y, Rigaudy P, Bizzari JP, Poupon MF. Antitumor activity of the new vinca-alkaloid S 12363 alone or in combination with verapamil on a human multidrug resistant renal carcinoma xenograft. In Vivo. 1993 Sep-Oct;7(5):399-405. PubMed PMID: 7906553.

4: Lelievre E, Guillaudeux J, Cardona H, Bourguignat A, Lokiec F, Solere P, Lucas C, Sauveur C. Human pharmacokinetics of a new Vinca alkaloid S 12363 with use of a monoclonal antibody-based radio- or enzyme immunoassay. Cancer Res. 1993 Aug 1;53(15):3536-40. PubMed PMID: 8339259.

5: Atassi G, Berlion M, el Oche Y, Bizzari JP. Characterization of the pharmacological antitumor effects of S 12363, a new vinca alkaloid. Anticancer Res. 1991 Mar-Apr;11(2):975-80. PubMed PMID: 2064354.

6: Fischel JL, Berlion M, Formento P, Bizzari JP, Milano G. Evaluation of the time-schedule dependency for the cytotoxic activity of the new vinca alkaloid derivative, S 12363 (vinfosiltine). Eur J Cancer. 1993;29A(13):1890-4. PubMed PMID: 8260248.

7: Gordon BH, Bakes DM, Bennett P, LeBras B, Walther B, Lucas C, Marc S, Gouyette A. Methods for the analysis of the new vinca alkaloid derivative, S 12363, in plasma by high-performance liquid chromatography with fluorescence detection. J Chromatogr B Biomed Appl. 1994 Jul 1;657(1):163-71. PubMed PMID: 7952064.

8: Pierré A, Lavielle G, Hautefaye P, Seurre G, Leonce S, Saint-Dizier D, Boutin JA, Cudennec CA. Pharmacological properties of a new alpha-aminophosphonic acid derivative of vinblastine. Anticancer Res. 1990 Jan-Feb;10(1):139-44. PubMed PMID: 2334119.

9: Pierré A, Pérez V, Léonce S, Boutin JA, Saint-Dizier D, Hautefaye P, Lavielle G, Atassi G. Relationship between the cellular accumulation and the cytotoxicity of S12363, a new Vinca alkaloid derivative. Cancer Chemother Pharmacol. 1992;29(5):367-74. PubMed PMID: 1551175.

10: Budman DR. New vinca alkaloids and related compounds. Semin Oncol. 1992 Dec;19(6):639-45. Review. PubMed PMID: 1462165.

11: Leonce S, Anstett M, Combe-Perez V, Pierre A. Flow cytometric evaluation of the cell cycle perturbations induced by S12363, a new vinca alkaloid derivative. Anticancer Drugs. 1990 Dec;1(2):179-83. PubMed PMID: 2131051.

12: Chemin C, Péan JM, Bourgaux C, Pabst G, Wüthrich P, Couvreur P, Ollivon M. Supramolecular organization of S12363-liposomes prepared with two different remote loading processes. Biochim Biophys Acta. 2009 May;1788(5):926-35. doi: 10.1016/j.bbamem.2008.11.017. Epub 2008 Dec 3. PubMed PMID: 19101501.

13: Verdier-Pinard P, Garès M, Wright M. Differential in vitro association of vinca alkaloid-induced tubulin spiral filaments into aggregated spirals. Biochem Pharmacol. 1999 Sep 15;58(6):959-71. PubMed PMID: 10509748.

14: Adenis A, Pion JM, Fumoleau P, Pouillart P, Marty M, Giroux B, Bonneterre J. Phase II study of a new vinca alkaloid derivative, S12363, in advanced breast cancer. Cancer Chemother Pharmacol. 1995;35(6):527-8. PubMed PMID: 7882462.

15: Stanley AJ, Kaprielian R, Retsas S. Evaluation of S12363, a novel vinca alkaloid drug in the treatment of advanced malignant melanoma. A phase II study. Anticancer Res. 1993 Jan-Feb;13(1):31-2. PubMed PMID: 8476226.

16: Urien S, Bastian G, Lucas C, Bizzari JP, Tillement JP. Binding of a new vinca alkaloid derivative, S12363, to human plasma proteins and platelets. Usefulness of an erythrocyte partitioning technique. Invest New Drugs. 1992 Nov;10(4):263-8. PubMed PMID: 1487399.

17: Tolis C, Photiou A, Camplejohn RS, Retsas S. Growth inhibitory activity of S12363, a novel vinca alkaloid derivative on human melanoma cell lines. Anticancer Res. 1993 Jan-Feb;13(1):161-6. PubMed PMID: 8476208.

18: Ings RM, Lelièvre E, Ardiet C, Clavel M, Leyvraz S, Minaidis D, Lokiec F, Turpin F, Solere P, Lucas C. Value of early pharmacodynamic and pharmacokinetic investigations with anticancer drugs: data from phase I tolerance studies on a new vinca alkaloid derivative. Xenobiotica. 1992 Jul;22(7):871-80. PubMed PMID: 1455905.