WARNING: This product is for research use only, not for human or veterinary use.
Hodoodo CAT#: H206098
CAS#: 345915-10-8
Description: AZD-3409 is a potent prenyl transferase inhibitor. AZD-3409 showed higher potency than lonafarnib. The mean IC(50) for cytotoxicity of AZD3409 was 510 in MEF cells, 10,600 in A549 cells and 6,170 in MCF7 cells, respectively. In these cells, the IC(50) for FTase activity of AZD3409 ranged from 3.0 to 14.2 nM and of lonafarnib from 0.26 to 31.3 nM. AZD3409 inhibits farnesylation to a higher extent than geranylgeranylation. Both inhibition of farnesylation and geranylgeranylation could not be correlated to the antiproliferative activity of the drug. AZD3409 might be active in gefitinib-resistant breast carcinoma.
Hodoodo Cat#: H206098
Name: AZD-3409
CAS#: 345915-10-8
Chemical Formula: C34H41FN4O4S2
Exact Mass: 652.26
Molecular Weight: 652.842
Elemental Analysis: C, 62.55; H, 6.33; F, 2.91; N, 8.58; O, 9.80; S, 9.82
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Synonym: AZD3409; AZD-3409; AZD 3409.
IUPAC/Chemical Name: (S)-isopropyl 2-(2-(4-fluorophenethyl)-5-((((2S,4S)-4-(nicotinoylthio)pyrrolidin-2-yl)methyl)amino)benzamido)-4-(methylthio)butanoate
InChi Key: HKGUHEGKBLYKHY-QMOZSOIISA-N
InChi Code: InChI=1S/C34H41FN4O4S2/c1-22(2)43-33(41)31(14-16-44-3)39-32(40)30-18-27(13-10-24(30)9-6-23-7-11-26(35)12-8-23)37-20-28-17-29(21-38-28)45-34(42)25-5-4-15-36-19-25/h4-5,7-8,10-13,15,18-19,22,28-29,31,37-38H,6,9,14,16-17,20-21H2,1-3H3,(H,39,40)/t28-,29-,31-/m0/s1
SMILES Code: O=C(OC(C)C)[C@@H](NC(C1=CC(NC[C@H]2NC[C@@H](SC(C3=CN=CC=C3)=O)C2)=CC=C1CCC4=CC=C(F)C=C4)=O)CCSC
Appearance: white 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, 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:
| Biological target: | |
| In vitro activity: | |
| In vivo activity: |
The following data is based on the product molecular weight 652.84 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.
| 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: |
1: Moorthy NS, Sousa SF, Ramos MJ, Fernandes PA. Farnesyltransferase inhibitors: a comprehensive review based on quantitative structural analysis. Curr Med Chem. 2013;20(38):4888-923. PubMed PMID: 24059235.
2: Ashworth IW, Cox BG, Meyrick B. Kinetics and mechanism of N-Boc cleavage: evidence of a second-order dependence upon acid concentration. J Org Chem. 2010 Dec 3;75(23):8117-25. doi: 10.1021/jo101767h. Epub 2010 Nov 10. PubMed PMID: 21067172.
3: Appels NM, Bolijn MJ, van Eijndhoven MA, Stephens TC, Beijnen JH, Schellens JH. Characterization of the in vitro activity of AZD3409, a novel prenyl transferase inhibitor. Cancer Chemother Pharmacol. 2011 Jan;67(1):137-45. doi: 10.1007/s00280-010-1300-6. Epub 2010 Mar 13. PubMed PMID: 20229082.
4: Abdel-Rehim M, Andersson A, Breitholtz-Emanuelsson A, Sandberg-Ställ M, Brunfelter K, Pettersson KJ, Norsten-Höög C. MEPS as a rapid sample preparation method to handle unstable compounds in a complex matrix: determination of AZD3409 in plasma samples utilizing MEPS-LC-MS-MS. J Chromatogr Sci. 2008 Jul;46(6):518-23. PubMed PMID: 18647473.
5: Appels NM, Bolijn MJ, Chan K, Stephens TC, Hoctin-Boes G, Middleton M, Beijnen JH, de Bono JS, Harris AL, Schellens JH. Phase I pharmacokinetic and pharmacodynamic study of the prenyl transferase inhibitor AZD3409 in patients with advanced cancer. Br J Cancer. 2008 Jun 17;98(12):1951-8. doi: 10.1038/sj.bjc.6604402. Epub 2008 May 27. PubMed PMID: 18506143; PubMed Central PMCID: PMC2441954.
6: Streeper R, Campos D, Carrizales G, Stephens TC, Izbicka E. Regulation of tumor signaling pathways by AZD3409 in vitro. Anticancer Res. 2006 Nov-Dec;26(6B):4185-9. PubMed PMID: 17201131.
7: Maiello MR, D'Alessio A, De Luca A, Carotenuto A, Rachiglio AM, Napolitano M, Cito L, Guzzo A, Normanno N. AZD3409 inhibits the growth of breast cancer cells with intrinsic resistance to the EGFR tyrosine kinase inhibitor gefitinib. Breast Cancer Res Treat. 2007 May;102(3):275-82. Epub 2006 Sep 27. PubMed PMID: 17004112.
8: Cengel KA, Deutsch E, Stephens TC, Voong KR, Kao GD, Bernhard EJ. Radiosensitizing effects of the prenyltransferase inhibitor AZD3409 against RAS mutated cell lines. Cancer Biol Ther. 2006 Sep;5(9):1206-10. Epub 2006 Sep 11. PubMed PMID: 16969121.
9: Appels NM, Rosing H, Stephens TC, Schellens JH, Beijnen JH. Quantification of farnesylmethylcysteine in lysates of peripheral blood mononuclear cells using liquid chromatography coupled with electrospray tandem mass spectrometry: pharmacodynamic assay for farnesyl transferase inhibitors. Anal Chem. 2006 Apr 15;78(8):2617-22. PubMed PMID: 16615771.
10: Wakeling AE. Inhibitors of growth factor signalling. Endocr Relat Cancer. 2005 Jul;12 Suppl 1:S183-7. Review. PubMed PMID: 16113095.
