AZD-4547
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MedKoo CAT#: 204550

CAS#: 1035270-39-3

Description: AZD4547 is an orally bioavailable inhibitor of the fibroblast growth factor receptor (FGFR) with potential antineoplastic activity. FGFR inhibitor AZD4547 binds to and inhibits FGFR, which may result in the inhibition of FGFR-related signal transduction pathways, and, so, the inhibition of tumor cell proliferation and tumor cell death. FGFR, up-regulated in many tumor cell types, is a receptor tyrosine kinase essential to tumor cellular proliferation, differentiation and survival.


Chemical Structure

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AZD-4547
CAS# 1035270-39-3

Theoretical Analysis

MedKoo Cat#: 204550
Name: AZD-4547
CAS#: 1035270-39-3
Chemical Formula: C26H33N5O3
Exact Mass: 463.25834
Molecular Weight: 463.57192
Elemental Analysis: C, 67.36; H, 7.18; N, 15.11; O, 10.35

Price and Availability

Size Price Availability Quantity
50.0mg USD 150.0 Same day
100.0mg USD 250.0 Same day
200.0mg USD 450.0 Same day
500.0mg USD 750.0 Same day
1.0g USD 1250.0 Same day
2.0g USD 2150.0 Same day
5.0g USD 3850.0 2 weeks
10.0g USD 5950.0 2 weeks
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Related CAS #: 1035270-39-3   1394854-62-6    

Synonym: AZD4547; AZD-4547; AZD 4547.

IUPAC/Chemical Name: N-(5-(3,5-dimethoxyphenethyl)-1H-pyrazol-3-yl)-4-((3S,5R)-3,5-dimethylpiperazin-1-yl)benzamide

InChi Key: VRQMAABPASPXMW-HDICACEKSA-N

InChi Code: InChI=1S/C26H33N5O3/c1-17-15-31(16-18(2)27-17)22-9-6-20(7-10-22)26(32)28-25-13-21(29-30-25)8-5-19-11-23(33-3)14-24(12-19)34-4/h6-7,9-14,17-18,27H,5,8,15-16H2,1-4H3,(H2,28,29,30,32)/t17-,18+

SMILES Code: O=C(NC1=NNC(CCC2=CC(OC)=CC(OC)=C2)=C1)C3=CC=C(N4C[C@H](C)N[C@H](C)C4)C=C3

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

Biological target: AZD4547 inhibits FGFR1, FGFR2, FGFR3, and FGFR4 with IC50s of 0.2 nM, 2.5 nM, 1.8 nM, and 165 nM, respectively.
In vitro activity: AZD-4547 inhibited CRC (colorectal cancer) cell growth in vitro, and its activity correlated with the FGFR-1/2 expression level. AZD-4547 was cytotoxic and pro-apoptotic in FGFR-1/2-expressed CRC cell lines (NCI-H716 and HCT-116), but not in FGFR-1/2 null HT-29 cells. Further, AZD-4547 inhibited cell cycle progression and attenuated the activation of FGFR1-FGFR substrate 2 (FRS-2), ERK/mitogen-activated protein kinase (MAPK), and AKT/mammalian target of rapamycin (AKT/mTOR) signalings in NCI-H716 and HCT-116 cells. Reference: Tumour Biol. 2015 Jul;36(7):5641-8. https://link.springer.com/article/10.1007/s13277-015-3237-1
In vivo activity: To investigate the therapeutic potential of AZD4547, MMTV-ErbB2 mice with palpable spontaneous tumors were treated with AZD4547 (6 mg/kg/day) for 3 weeks. AZD4547 markedly repressed the TIC (tumor initiating cells) population in spontaneous tumors, as measured by the percent of ALDH+ tumor cells (Fig. 7a). Likewise, the self-renewal capacity and anchorage-independent growth of these tumor cells were significantly reduced in primary tumorsphere and 3D culture assays, respectively (Fig. 7b,c). Altogether, the stem cell data suggest that AZD4547 selectively targets (cancer stem cell) CSC/TIC populations, thus indicating a mechanism for the anti-cancer potential of AZD4547. Reference: Sci Rep. 2017 Sep 12;7(1):11306. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5595825/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMF 25.0 53.93
DMSO 47.67 102.83
DMSO:PBS (pH 7.2) (1:1) 0.5 1.08
Ethanol 1.6 3.45

Preparing Stock Solutions

The following data is based on the product molecular weight 463.57192 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: 1. Yao TJ, Zhu JH, Peng DF, Cui Z, Zhang C, Lu PH. AZD-4547 exerts potent cytostatic and cytotoxic activities against fibroblast growth factor receptor (FGFR)-expressing colorectal cancer cells. Tumour Biol. 2015 Jul;36(7):5641-8. doi: 10.1007/s13277-015-3237-1. Epub 2015 Feb 19. PMID: 25691251. 2. Zhao Q, Parris AB, Howard EW, Zhao M, Ma Z, Guo Z, Xing Y, Yang X. FGFR inhibitor, AZD4547, impedes the stemness of mammary epithelial cells in the premalignant tissues of MMTV-ErbB2 transgenic mice. Sci Rep. 2017 Sep 12;7(1):11306. doi: 10.1038/s41598-017-11751-7. PMID: 28900173; PMCID: PMC5595825. 3. Huang Y, Wang F, Li H, Xu S, Xu W, Pan X, Hu Y, Mao L, Qian S, Pan J. Inhibition of Fibroblast Growth Factor Receptor by AZD4547 Protects Against Inflammation in Septic Mice. Inflammation. 2019 Dec;42(6):1957-1967. doi: 10.1007/s10753-019-01056-4. PMID: 31321583.
In vitro protocol: 1. Yao TJ, Zhu JH, Peng DF, Cui Z, Zhang C, Lu PH. AZD-4547 exerts potent cytostatic and cytotoxic activities against fibroblast growth factor receptor (FGFR)-expressing colorectal cancer cells. Tumour Biol. 2015 Jul;36(7):5641-8. doi: 10.1007/s13277-015-3237-1. Epub 2015 Feb 19. PMID: 25691251. 2. Zhao Q, Parris AB, Howard EW, Zhao M, Ma Z, Guo Z, Xing Y, Yang X. FGFR inhibitor, AZD4547, impedes the stemness of mammary epithelial cells in the premalignant tissues of MMTV-ErbB2 transgenic mice. Sci Rep. 2017 Sep 12;7(1):11306. doi: 10.1038/s41598-017-11751-7. PMID: 28900173; PMCID: PMC5595825.
In vivo protocol: 1. Huang Y, Wang F, Li H, Xu S, Xu W, Pan X, Hu Y, Mao L, Qian S, Pan J. Inhibition of Fibroblast Growth Factor Receptor by AZD4547 Protects Against Inflammation in Septic Mice. Inflammation. 2019 Dec;42(6):1957-1967. doi: 10.1007/s10753-019-01056-4. PMID: 31321583. 2. Zhao Q, Parris AB, Howard EW, Zhao M, Ma Z, Guo Z, Xing Y, Yang X. FGFR inhibitor, AZD4547, impedes the stemness of mammary epithelial cells in the premalignant tissues of MMTV-ErbB2 transgenic mice. Sci Rep. 2017 Sep 12;7(1):11306. doi: 10.1038/s41598-017-11751-7. PMID: 28900173; PMCID: PMC5595825.

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1: Ramsey MR, Wilson C, Ory B, Rothenberg SM, Faquin W, Mills AA, Ellisen LW. FGFR2 signaling underlies p63 oncogenic function in squamous cell carcinoma. J Clin Invest. 2013 Aug 1;123(8):3525-38. doi: 10.1172/JCI68899. Epub 2013 Jul 8. PubMed PMID: 23867503; PubMed Central PMCID: PMC3726171.

2: Fox EM, Kuba MG, Miller TW, Davies BR, Arteaga CL. Autocrine IGF-I/insulin receptor axis compensates for inhibition of AKT in ER-positive breast cancer cells with resistance to estrogen deprivation. Breast Cancer Res. 2013 Jul 11;15(4):R55. [Epub ahead of print] PubMed PMID: 23844554.

3: Katoh M, Nakagama H. FGF Receptors: Cancer Biology and Therapeutics. Med Res Rev. 2013 May 21. doi: 10.1002/med.21288. [Epub ahead of print] PubMed PMID: 23696246.

4: Ware KE, Hinz TK, Kleczko E, Singleton KR, Marek LA, Helfrich BA, Cummings CT, Graham DK, Astling D, Tan AC, Heasley LE. A mechanism of resistance to gefitinib mediated by cellular reprogramming and the acquisition of an FGF2-FGFR1 autocrine growth loop. Oncogenesis. 2013 Mar 25;2:e39. doi: 10.1038/oncsis.2013.4. PubMed PMID: 23552882; PubMed Central PMCID: PMC3641357.

5: Xie L, Su X, Zhang L, Yin X, Tang L, Zhang X, Xu Y, Gao Z, Liu K, Zhou M, Gao B, Shen D, Zhang L, Ji J, Gavine PR, Zhang J, Kilgour E, Zhang X, Ji Q. FGFR2 gene amplification in gastric cancer predicts sensitivity to the selective FGFR inhibitor AZD4547. Clin Cancer Res. 2013 May 1;19(9):2572-83. doi: 10.1158/1078-0432.CCR-12-3898. Epub 2013 Mar 14. PubMed PMID: 23493349.

6: Zhao R, Xie X, Shen GX. Effects of glycated low-density lipoprotein on cell viability, proliferation, and growth factors of mouse embryo fibroblasts. Can J Physiol Pharmacol. 2013 Jan;91(1):64-70. doi: 10.1139/cjpp-2012-0234. Epub 2013 Jan 21. PubMed PMID: 23369077.

7: Zhang J, Zhang L, Su X, Li M, Xie L, Malchers F, Fan S, Yin X, Xu Y, Liu K, Dong Z, Zhu G, Qian Z, Tang L, Schöttle J, Zhan P, Ji Q, Kilgour E, Smith PD, Brooks AN, Thomas RK, Gavine PR. Translating the therapeutic potential of AZD4547 in FGFR1-amplified non-small cell lung cancer through the use of patient-derived tumor xenograft models. Clin Cancer Res. 2012 Dec 15;18(24):6658-67. doi: 10.1158/1078-0432.CCR-12-2694. Epub 2012 Oct 18. Erratum in: Clin Cancer Res. 2013 Jul 1;19(13):3714. Schöttle, Jakob [added]. PubMed PMID: 23082000.

8: Chell V, Balmanno K, Little AS, Wilson M, Andrews S, Blockley L, Hampson M, Gavine PR, Cook SJ. Tumour cell responses to new fibroblast growth factor receptor tyrosine kinase inhibitors and identification of a gatekeeper mutation in FGFR3 as a mechanism of acquired resistance. Oncogene. 2013 Jun 20;32(25):3059-70. doi: 10.1038/onc.2012.319. Epub 2012 Aug 6. PubMed PMID: 22869148.

9: Singh D, Chan JM, Zoppoli P, Niola F, Sullivan R, Castano A, Liu EM, Reichel J, Porrati P, Pellegatta S, Qiu K, Gao Z, Ceccarelli M, Riccardi R, Brat DJ, Guha A, Aldape K, Golfinos JG, Zagzag D, Mikkelsen T, Finocchiaro G, Lasorella A, Rabadan R, Iavarone A. Transforming fusions of FGFR and TACC genes in human glioblastoma. Science. 2012 Sep 7;337(6099):1231-5. doi: 10.1126/science.1220834. Epub 2012 Jul 26. PubMed PMID: 22837387; PubMed Central PMCID: PMC3677224.

10: Gavine PR, Mooney L, Kilgour E, Thomas AP, Al-Kadhimi K, Beck S, Rooney C, Coleman T, Baker D, Mellor MJ, Brooks AN, Klinowska T. AZD4547: an orally bioavailable, potent, and selective inhibitor of the fibroblast growth factor receptor tyrosine kinase family. Cancer Res. 2012 Apr 15;72(8):2045-56. doi: 10.1158/0008-5472.CAN-11-3034. Epub 2012 Feb 27. PubMed PMID: 22369928.

AZD-4547

50.0mg / USD 150.0


Additional Information

Related CAS#
Sci-Finder listed CAS#1394854-62-6 for AZD-4547
ChemIDplus listed CAS#1035270-39-3 for AZD-4547, see website: https://chem.nlm.nih.gov/chemidplus/rn/1035270-39-3
 
According to Sci-Finder,
Chemical name for CAS#1394854-62-6:
N-[3-[2-(3,5-Dimethoxyphenyl)ethyl]-1H-pyrazol-5-yl]-4-(3,5-dimethyl-1-piperazinyl)benzamide
Chemical name for CAS#1035270-39-3:
rel-N-[5-[2-(3,5-Dimethoxyphenyl)ethyl]-1H-pyrazol-3-yl]-4-[(3R,5S)-3,5-dimethyl-1-piperazinyl]benzamide