Vinfosiltine

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

MedKoo CAT#: 461608

CAS#: 123286-00-0

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

Chemical Structure

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Vinfosiltine
CAS# 123286-00-0
Instruction

Theoretical Analysis

MedKoo Cat#: 461608
Name: Vinfosiltine
CAS#: 123286-00-0
Chemical Formula: C51H72N5O10P
Exact Mass: 945.50
Molecular Weight: 946.130
Elemental Analysis: C, 64.74; H, 7.67; N, 7.40; O, 16.91; P, 3.27

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

Request quote for custom synthesis

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

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

More Info:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 946.13 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
Formulation protocol:
In vitro protocol:
In vivo protocol:

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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.