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MedKoo Cat#: 585415 | Name: FR 900452

Description:

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

FR 900452 is a platelet activating factor antagonist from fermentatiion products of Streptomyces phaeofaciens.

Chemical Structure

FR 900452
FR 900452
CAS#101706-33-6

Theoretical Analysis

MedKoo Cat#: 585415

Name: FR 900452

CAS#: 101706-33-6

Chemical Formula: C22H25N3O3S

Exact Mass: 411.1617

Molecular Weight: 411.52

Elemental Analysis: C, 64.21; H, 6.12; N, 10.21; O, 11.66; S, 7.79

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
No Data
Synonym
FR 900452; FR900452; FR-900452
IUPAC/Chemical Name
1-methyl-3-[1-[5-(methylsulfanylmethyl)-6-oxo-3-(2-oxocyclopent-3-en-1-ylidene)piperazin-2-yl]ethyl]-3H-indol-2-one
InChi Key
UAPDNDKYPBHNQT-ZHZULCJRSA-N
InChi Code
InChI=1S/C22H25N3O3S/c1-12(18-13-7-4-5-9-16(13)25(2)22(18)28)19-20(14-8-6-10-17(14)26)23-15(11-29-3)21(27)24-19/h4-7,9-10,12,15,18-19,23H,8,11H2,1-3H3,(H,24,27)/b20-14-
SMILES Code
O=C1N(C)C2=C(C=CC=C2)C1C(C(/C(NC3CSC)=C4C(C=CC/4)=O)NC3=O)C
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
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 411.52 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
1: Komaki H, Ichikawa N, Hosoyama A, Fujita N, Igarashi Y. Draft Genome Sequence of Streptomyces sp. TP-A0890, a Producer of FR-900452 and A-74863a. Genome Announc. 2015 Oct 15;3(5). pii: e01212-15. doi: 10.1128/genomeA.01212-15. PubMed PMID: 26472848; PubMed Central PMCID: PMC4611700. 2: Okamoto M, Yoshida K, Nishikawa M, Ando T, Iwami M, Kohsaka M, Aoki H. FR-900452, a specific antagonist of platelet activating factor (PAF) produced by Streptomyces phaeofaciens. I. Taxonomy, fermentation, isolation, and physico-chemical and biological characteristics. J Antibiot (Tokyo). 1986 Feb;39(2):198-204. PubMed PMID: 3082838. 3: Okamoto M, Yoshida K, Nishikawa M, Kohsaka M, Aoki H. Platelet activating factor (PAF) involvement in endotoxin-induced thrombocytopenia in rabbits: studies with FR-900452, a specific inhibitor of PAF. Thromb Res. 1986 Jun 1;42(5):661-71. PubMed PMID: 3754990. 4: Negro Alvarez JM, Miralles López JC, Ortiz Martínez JL, Abellán Alemán A, Rubio del Barrio R. Platelet-activating factor antagonists. Allergol Immunopathol (Madr). 1997 Sep-Oct;25(5):249-58. Review. PubMed PMID: 9395010. 5: Okamoto M, Yoshida K, Nishikawa M, Hayashi K, Uchida I, Kohsaka M, Aoki H. Studies of platelet activating factor (PAF) antagonists from microbial products. III. Pharmacological studies of FR-900452 in animal models. Chem Pharm Bull (Tokyo). 1986 Jul;34(7):3005-10. PubMed PMID: 3769104. 6: Hu W, McNicholl IK, Choy PC, Man RY. Partial agonist effect of the platelet-activating factor receptor antagonists, WEB 2086 and WEB 2170, in the rat perfused heart. Br J Pharmacol. 1993 Oct;110(2):645-50. PubMed PMID: 8242237; PubMed Central PMCID: PMC2175904. 7: Suzuki S, Nozawa R, Suzuki J, Kato K, Suzuki H, Sakurai K. [Effect of a specific antagonist of platelet-activating factor, FR-900452, on proteinuria and urinary thromboxane excretion in aminonucleoside nephrotic rats]. Nihon Jinzo Gakkai Shi. 1988 Aug;30(8):985-90. Japanese. PubMed PMID: 3244194. 8: Hu W, Kinnaird AA, Man RY. Mechanisms of the coronary vascular effects of platelet-activating factor in the rat perfused heart. Br J Pharmacol. 1991 May;103(1):1097-102. PubMed PMID: 1652337; PubMed Central PMCID: PMC1908074. 9: Man RY, Kinnaird AA. Similar coronary vascular effects in the rat perfused heart of platelet-activating factor structural analogues with agonist and antagonist properties. Br J Pharmacol. 1995 Nov;116(5):2359-64. PubMed PMID: 8581269; PubMed Central PMCID: PMC1909066. 10: Chan WP, Levy JV. Effects of antiplatelet agents on platelet aggregation induced by platelet--activating factor (PAF) in human whole blood. Prostaglandins. 1991 Oct;42(4):337-42. PubMed PMID: 1665568. 11: Hu WM, Man RY. Differential actions of platelet-activating factor (PAF) receptor antagonists on the vasodilator and vasoconstrictor effects of PAF in the rat perfused heart. Br J Pharmacol. 1991 Dec;104(4):773-5. PubMed PMID: 1667284; PubMed Central PMCID: PMC1908823. 12: Kato T, Kudo I, Hayashi H, Onozaki K, Inoue K. Augmentation of DNA synthesis in guinea pig bone marrow cells by platelet-activating factor (PAF). Biochem Biophys Res Commun. 1988 Dec 15;157(2):563-8. PubMed PMID: 3202869. 13: Tanaka T, Tokumura A, Tsukatani H. Platelet-activating factor (PAF)-like phospholipids formed during peroxidation of phosphatidylcholines from different foodstuffs. Biosci Biotechnol Biochem. 1995 Aug;59(8):1389-93. PubMed PMID: 7549088. 14: Tanaka T, Iimori M, Tsukatani H, Tokumura A. Platelet-aggregating effects of platelet-activating factor-like phospholipids formed by oxidation of phosphatidylcholines containing an sn-2-polyunsaturated fatty acyl group. Biochim Biophys Acta. 1994 Jan 3;1210(2):202-8. PubMed PMID: 8280771. 15: Hirafuji M, Shinoda H. Antagonism of platelet-activating factor-induced increase in cytosolic free calcium concentration in human endothelial cells. Jpn J Pharmacol. 1992 Mar;58(3):231-41. PubMed PMID: 1513073. 16: Moritoki H, Hisayama T, Takeuchi S, Miyano H, Kondoh W. Involvement of nitric oxide pathway in the PAF-induced relaxation of rat thoracic aorta. Br J Pharmacol. 1992 Sep;107(1):196-201. PubMed PMID: 1358382; PubMed Central PMCID: PMC1907606. 17: Yoshida K, Okamoto M, Shimazaki N, Hemmi K. PAF inhibitors of microbial origin. Studies on diketopiperazine derivatives. Prog Biochem Pharmacol. 1988;22:66-80. Review. PubMed PMID: 2457219. 18: Tokumura A, Terao M, Okamoto M, Yoshida K, Tsukatani H. Study of platelet activating factor and its antagonists on rat colon strip with a new method avoiding tachyphylaxis. Eur J Pharmacol. 1988 Apr 13;148(3):353-60. PubMed PMID: 3384001. 19: Tokumura A, Yube N, Terao M, Tsukatani H. Antagonism of platelet-activating factor in isolated rat colon: possible mechanism. Lipids. 1991 Dec;26(12):1344-6. PubMed PMID: 1819730.