FR180204
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MedKoo CAT#: 406556

CAS#: 865362-74-9

Description: FR180204 is a novel and selective inhibitor of extracellular signal-regulated kinase (ERK), which may be a potential new therapy for rheumatoid arthritis.FR180204 showed activity to inhibit ERKs (IC50 values are 0.14 and 0.31 μ M for ERK2 and ERK1 respectively).


Chemical Structure

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FR180204
CAS# 865362-74-9

Theoretical Analysis

MedKoo Cat#: 406556
Name: FR180204
CAS#: 865362-74-9
Chemical Formula: C18H13N7
Exact Mass: 327.12324
Molecular Weight: 327.34
Elemental Analysis: C, 66.04; H, 4.00; N, 29.95

Price and Availability

Size Price Availability Quantity
50.0mg USD 450.0 2 Weeks
100.0mg USD 750.0 2 Weeks
200.0mg USD 1250.0 2 Weeks
500.0mg USD 1950.0 2 Weeks
1.0g USD 2950.0 2 Weeks
2.0g USD 5450.0 2 Weeks
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Synonym: FR180204; FR-180204; FR 180204.

IUPAC/Chemical Name: 5-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridazin-3-amine

InChi Key: XVECMUKVOMUNLE-UHFFFAOYSA-N

InChi Code: InChI=1S/C18H13N7/c19-17-12-10-13(20-22-18(12)23-21-17)15-14-8-4-5-9-25(14)24-16(15)11-6-2-1-3-7-11/h1-10H,(H3,19,21,22,23)

SMILES Code: NC1=NNC2=NN=C(C3=C4C=CC=CN4N=C3C5=CC=CC=C5)C=C21

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, 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

Product Data:

Biological target: FR 180204 is an ATP-competitive and selective ERK inhibitor.
In vitro activity: As shown in Fig. 3A, treatment with 2 µM API-1 caused an increase in cytotoxicity at 24 h in DLD-1 cells (P=0.027), whereas treatment with 10 µM FR (FR180204) alone for 48 h increased cytotoxic effects compared with control LoVo cells. Reference: Oncol Lett. 2016 Oct; 12(4): 2463–2474. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5038487/
In vivo activity: Preventive administration of FR180204 (100 mg/kg, i.p., b.i.d.) significantly ameliorated the clinical arthritis and body weight loss occurring in the CIA mice. Further, FR180204-treated mice showed a significant decrease in plasma anti-CII antibody levels (62%). Reference: Naunyn Schmiedebergs Arch Pharmacol. 2007 Jan;374(4):311-6. https://pubmed.ncbi.nlm.nih.gov/17123065/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 43.18 131.91
DMF 30.0 91.65
DMF:PBS (pH 7.2) (1:1) 0.5 1.53
Ethanol 2.0 6.11

Preparing Stock Solutions

The following data is based on the product molecular weight 327.34 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. Saglam AS, Alp E, Elmazoglu Z, Menevse ES. Effect of API-1 and FR180204 on cell proliferation and apoptosis in human DLD-1 and LoVo colorectal cancer cells. Oncol Lett. 2016 Oct;12(4):2463-2474. doi: 10.3892/ol.2016.4995. Epub 2016 Aug 10. PMID: 27698814; PMCID: PMC5038487. 2. Ohori M, Takeuchi M, Maruki R, Nakajima H, Miyake H. FR180204, a novel and selective inhibitor of extracellular signal-regulated kinase, ameliorates collagen-induced arthritis in mice. Naunyn Schmiedebergs Arch Pharmacol. 2007 Jan;374(4):311-6. doi: 10.1007/s00210-006-0117-7. Epub 2006 Nov 23. PMID: 17123065.
In vitro protocol: 1. Saglam AS, Alp E, Elmazoglu Z, Menevse ES. Effect of API-1 and FR180204 on cell proliferation and apoptosis in human DLD-1 and LoVo colorectal cancer cells. Oncol Lett. 2016 Oct;12(4):2463-2474. doi: 10.3892/ol.2016.4995. Epub 2016 Aug 10. PMID: 27698814; PMCID: PMC5038487.
In vivo protocol: 1. Ohori M, Takeuchi M, Maruki R, Nakajima H, Miyake H. FR180204, a novel and selective inhibitor of extracellular signal-regulated kinase, ameliorates collagen-induced arthritis in mice. Naunyn Schmiedebergs Arch Pharmacol. 2007 Jan;374(4):311-6. doi: 10.1007/s00210-006-0117-7. Epub 2006 Nov 23. PMID: 17123065.

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1: Dirican A, Atmaca H, Bozkurt E, Erten C, Karaca B, Uslu R. Novel combination of docetaxel and thymoquinone induces synergistic cytotoxicity and apoptosis in DU-145 human prostate cancer cells by modulating PI3K-AKT pathway. Clin Transl Oncol. 2014 Jul 25. [Epub ahead of print] PubMed PMID: 25060568.

2: Sreekanth GP, Chuncharunee A, Sirimontaporn A, Panaampon J, Srisawat C, Morchang A, Malakar S, Thuwajit P, Kooptiwut S, Suttitheptumrong A, Songprakhon P, Noisakran S, Yenchitsomanus PT, Limjindaporn T. Role of ERK1/2 signaling in dengue virus-induced liver injury. Virus Res. 2014 Aug 8;188:15-26. doi: 10.1016/j.virusres.2014.03.025. Epub 2014 Apr 1. PubMed PMID: 24704674.

3: Yuen N, Lam TI, Wallace BK, Klug NR, Anderson SE, O'Donnell ME. Ischemic factor-induced increases in cerebral microvascular endothelial cell Na/H exchange activity and abundance: evidence for involvement of ERK1/2 MAP kinase. Am J Physiol Cell Physiol. 2014 May 15;306(10):C931-42. doi: 10.1152/ajpcell.00021.2013. Epub 2014 Mar 19. PubMed PMID: 24647544; PubMed Central PMCID: PMC4024711.

4: Bilsland AE, Stevenson K, Liu Y, Hoare S, Cairney CJ, Roffey J, Keith WN. Mathematical model of a telomerase transcriptional regulatory network developed by cell-based screening: analysis of inhibitor effects and telomerase expression mechanisms. PLoS Comput Biol. 2014 Feb 13;10(2):e1003448. doi: 10.1371/journal.pcbi.1003448. eCollection 2014 Feb. PubMed PMID: 24550717; PubMed Central PMCID: PMC3923661.

5: Choi NY, Choi H, Park HH, Lee EH, Yu HJ, Lee KY, Joo Lee Y, Koh SH. Neuroprotective effects of amlodipine besylate and benidipine hydrochloride on oxidative stress-injured neural stem cells. Brain Res. 2014 Mar 10;1551:1-12. doi: 10.1016/j.brainres.2014.01.016. Epub 2014 Jan 16. PubMed PMID: 24440775.

6: Thaler CD, Miyata H, Haimo LT, Cardullo RA. Waveform generation is controlled by phosphorylation and swimming direction is controlled by Ca2+ in sperm from the mosquito Culex quinquefasciatus. Biol Reprod. 2013 Dec 12;89(6):135. doi: 10.1095/biolreprod.113.109488. Print 2013 Dec. PubMed PMID: 24108305.

7: Anastassiadis T, Duong-Ly KC, Deacon SW, Lafontant A, Ma H, Devarajan K, Dunbrack RL Jr, Wu J, Peterson JR. A highly selective dual insulin receptor (IR)/insulin-like growth factor 1 receptor (IGF-1R) inhibitor derived from an extracellular signal-regulated kinase (ERK) inhibitor. J Biol Chem. 2013 Sep 27;288(39):28068-77. doi: 10.1074/jbc.M113.505032. Epub 2013 Aug 9. PubMed PMID: 23935097; PubMed Central PMCID: PMC3784719.

8: Sunaga N, Kaira K, Imai H, Shimizu K, Nakano T, Shames DS, Girard L, Soh J, Sato M, Iwasaki Y, Ishizuka T, Gazdar AF, Minna JD, Mori M. Oncogenic KRAS-induced epiregulin overexpression contributes to aggressive phenotype and is a promising therapeutic target in non-small-cell lung cancer. Oncogene. 2013 Aug 22;32(34):4034-42. doi: 10.1038/onc.2012.402. Epub 2012 Sep 10. PubMed PMID: 22964644.

9: Doghman M, Lalli E. Efficacy of the novel dual PI3-kinase/mTOR inhibitor NVP-BEZ235 in a preclinical model of adrenocortical carcinoma. Mol Cell Endocrinol. 2012 Nov 25;364(1-2):101-4. doi: 10.1016/j.mce.2012.08.014. Epub 2012 Aug 31. PubMed PMID: 22960230.

10: Ragusa M, Statello L, Maugeri M, Majorana A, Barbagallo D, Salito L, Sammito M, Santonocito M, Angelica R, Cavallaro A, Scalia M, Caltabiano R, Privitera G, Biondi A, Di Vita M, Cappellani A, Vasquez E, Lanzafame S, Tendi E, Celeste S, Di Pietro C, Basile F, Purrello M. Specific alterations of the microRNA transcriptome and global network structure in colorectal cancer after treatment with MAPK/ERK inhibitors. J Mol Med (Berl). 2012 Dec;90(12):1421-38. doi: 10.1007/s00109-012-0918-8. Epub 2012 Jun 4. PubMed PMID: 22660396.

FR180204

50.0mg / USD 450.0


Additional Information