WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 563600
CAS#: 156547-56-7
Description: FSCPX irreversible A1 adenosine receptor antagonist. FSCPX inhibits the effects of NBTI that are mediated by increasing the interstitial concentration of adenosine of endogenous (but not exogenous) origin. FSCPX (5 microM) completely reversed the increase in K+ current of guinea pig atrial myocytes caused by 100 microM adenosine (259 +/- 30 to 20 +/- 7 pA) but had no significant effect on K+ currents caused by either 0.5 microM carbachol or 100 microM GTP gamma S.
MedKoo Cat#: 563600
Name: FSCPX
CAS#: 156547-56-7
Chemical Formula: C23H27FN4O6S
Exact Mass: 506.1635
Molecular Weight: 506.54
Elemental Analysis: C, 54.54; H, 5.37; F, 3.75; N, 11.06; O, 18.95; S, 6.33
Synonym: FSCPX;
IUPAC/Chemical Name: 8-Cyclopentyl-3-[3-[[4(fluorosulphonyl)benzoyl]oxy]propyl]-1-propylxanthine
InChi Key: XJLGXHIRSHTRPQ-UHFFFAOYSA-N
InChi Code: InChI=1S/C23H27FN4O6S/c1-2-12-28-21(29)18-20(26-19(25-18)15-6-3-4-7-15)27(23(28)31)13-5-14-34-22(30)16-8-10-17(11-9-16)35(24,32)33/h8-11,15H,2-7,12-14H2,1H3,(H,25,26)
SMILES Code: O=C(N1CCC)N(CCCOC(C2=CC=C(S(=O)(F)=O)C=C2)=O)C3=C(NC(C4CCCC4)=N3)C1=O
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
The following data is based on the product molecular weight 506.54 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 |
1: Zsuga J, Erdei T, Szabó K, Lampe N, Papp C, Pinter A, Szentmiklosi AJ, Juhasz B, Szilvássy Z, Gesztelyi R. Methodical Challenges and a Possible Resolution in the Assessment of Receptor Reserve for Adenosine, an Agonist with Short Half-Life. Molecules. 2017 May 19;22(5). pii: E839. doi: 10.3390/molecules22050839. PubMed PMID: 28534854.
2: Kiss Z, Pak K, Zsuga J, Juhasz B, Varga B, Szentmiklosi AJ, Haines DD, Tosaki A, Gesztelyi R. The guinea pig atrial A1 adenosine receptor reserve for the direct negative inotropic effect of adenosine. Gen Physiol Biophys. 2013 Sep;32(3):325-35. doi: 10.4149/gpb_2013041. Epub 2013 Jul 2. PubMed PMID: 23817640.
3: Gesztelyi R, Kiss Z, Wachal Z, Juhasz B, Bombicz M, Csepanyi E, Pak K, Zsuga J, Papp C, Galajda Z, Branzaniuc K, Porszasz R, Szentmiklosi AJ, Tosaki A. The surmountable effect of FSCPX, an irreversible A(1) adenosine receptor antagonist, on the negative inotropic action of A(1) adenosine receptor full agonists in isolated guinea pig left atria. Arch Pharm Res. 2013 Mar;36(3):293-305. doi: 10.1007/s12272-013-0056-z. Epub 2013 Feb 28. PubMed PMID: 23456693.
4: Bozarov A, Wang YZ, Yu JG, Wunderlich J, Hassanain HH, Alhaj M, Cooke HJ, Grants I, Ren T, Christofi FL. Activation of adenosine low-affinity A3 receptors inhibits the enteric short interplexus neural circuit triggered by histamine. Am J Physiol Gastrointest Liver Physiol. 2009 Dec;297(6):G1147-62. doi: 10.1152/ajpgi.00295.2009. Epub 2009 Oct 1. PubMed PMID: 19808660; PubMed Central PMCID: PMC2850084.
5: Beauglehole AR, Baker SP, Scammells PJ. New irreversible adenosine A(1) antagonists based on FSCPX. Bioorg Med Chem Lett. 2002 Nov 4;12(21):3179-82. PubMed PMID: 12372528.
6: Lorenzen A, Beukers MW, van der Graaf PH, Lang H, van Muijlwijk-Koezen J, de Groote M, Menge W, Schwabe U, IJzerman AP. Modulation of agonist responses at the A(1) adenosine receptor by an irreversible antagonist, receptor-G protein uncoupling and by the G protein activation state. Biochem Pharmacol. 2002 Oct 15;64(8):1251-65. PubMed PMID: 12234606.
7: van Muijlwijk-Koezen JE, Timmerman H, van der Sluis RP, van de Stolpe AC, Menge WM, Beukers MW, van der Graaf PH, de Groote M, IJzerman AP. Synthesis and use of FSCPX, an irreversible adenosine A1 antagonist, as a 'receptor knock-down' tool. Bioorg Med Chem Lett. 2001 Mar 26;11(6):815-8. PubMed PMID: 11277527.
8: Beauglehole AR, Baker SP, Scammells PJ. Fluorosulfonyl-substituted xanthines as selective irreversible antagonists for the A(1)-adenosine receptor. J Med Chem. 2000 Dec 28;43(26):4973-80. PubMed PMID: 11150167.
9: Baker SP, Scammells PJ, Belardinelli L. Differential A(1)-adenosine receptor reserve for inhibition of cyclic AMP accumulation and G-protein activation in DDT(1) MF-2 cells. Br J Pharmacol. 2000 Jul;130(5):1156-64. PubMed PMID: 10882402; PubMed Central PMCID: PMC1572163.
10: Morey TE, Belardinelli L, Dennis DM. Validation of Furchgott's method to determine agonist-dependent A1-adenosine receptor reserve in guinea-pig atrium. Br J Pharmacol. 1998 Apr;123(7):1425-33. PubMed PMID: 9579739; PubMed Central PMCID: PMC1565302.
11: Srinivas M, Shryock JC, Dennis DM, Baker SP, Belardinelli L. Differential A1 adenosine receptor reserve for two actions of adenosine on guinea pig atrial myocytes. Mol Pharmacol. 1997 Oct;52(4):683-91. PubMed PMID: 9380032.
12: Srinivas M, Shryock JC, Scammells PJ, Ruble J, Baker SP, Belardinelli L. A novel irreversible antagonist of the A1-adenosine receptor. Mol Pharmacol. 1996 Jul;50(1):196-205. PubMed PMID: 8700113.
