SC 57461A - CAS 423169-68-0
Category: Inhibitor
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Molecular Formula:
C20H25NO3.HCl
Molecular Weight:
363.88
COA:
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Targets:
Others
Description:
SC 57461A is a potent, selective and orally bioactive inhibitor of leukotriene A4 (LTA4) hydrolase without inhibitory effects on other enzymes of the arachidonic acid cascade including COX-1, COX-2, LTC4 synthase and 5-lipoxygenase. SC 57461A inhibits LTB4 production in whole blood (IC50 = 49 nM).
Brife Description:
LTA4 hydrolase inhibitor
Purity:
≥98% by HPLC
Appearance:
White Solid
Synonyms:
SC 57461; SC-57461; SC57461; SC 57461A; SC-57461A; SC57461A; N-methyl-N-[3-[4-(phenylmethyl)phenoxy]propyl]-β-alanine hydrochloride; 3-[3-(4-benzylphenoxy)propyl-methylamino]propanoic acid hydrochloride
MSDS:
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Melting Point:
163-165°C
InChIKey:
SBBJJLDNKNNWFJ-UHFFFAOYSA-N
InChI:
InChI=1S/C20H25NO3.ClH/c1-21(14-12-20(22)23)13-5-15-24-19-10-8-18(9-11-19)16-17-6-3-2-4-7-17;/h2-4,6-11H,5,12-16H2,1H3,(H,22,23);1H
Canonical SMILES:
CN(CCCOC1=CC=C(C=C1)CC2=CC=CC=C2)CCC(=O)O.Cl
1.Inhibitors of leukotriene A4 (LTA4) hydrolase as potential anti-inflammatory agents.
Penning TD Curr Pharm Des. 2001 Feb;7(3):163-79.
Leukotriene A4 (LTA4) hydrolase is a zinc-containing enzyme which stereospecifically catalyzes the hydrolysis of the epoxide LTA4 to the diol leukotriene B4 (LTB4). There is substantial evidence that LTB4 plays a significant role in the amplification of many inflammatory disease states. Therapeutic agents which selectively inhibit LTA4 hydrolase would block the formation of LTB4 and thus be potentially useful for the treatment of inflammation. Numerous inhibitors of LTA4 hydrolase have been reported over the past 15-20 years. Several early inhibitors were based on the structure of the natural substrate, LTA4. Later approaches utilized known inhibitors of related zinc-containing metalloproteinases and led to the identification of captopril, bestatin and kelatorphan as potent inhibitors of LTA4 hydrolase. This led to the design of a number of peptide and non-peptide analogs which contained potential zinc-chelating moieties, including thiols, hydroxamates and norstatines. A more recent series of non-peptidic, non-zinc chelating inhibitors of LTA4 hydrolase has been reported. This work led to the identification of several novel classes of analogs, including imidazopyridines, amidines and cyclic and acyclic amino acid derivatives, ultimately resulting in the identification of two potential clinical candidates SC-56938 and SC-57461A.
2.Isolation and identification of metabolites of leukotriene A4 hydrolase inhibitor SC-57461 in rats.
Yuan JH;Birkmeier J;Yang DC;Hribar JD;Liu N;Bible R;Hajdu E;Rock M;Schoenhard G Drug Metab Dispos. 1996 Oct;24(10):1124-33.
The metabolic fate of SC-57461, N-methyl-N-[3-[4-(phenylmethyl)-phenoxy]propyl]-beta-alanine, a potent and specific inhibitor of the leukotriene A4 hydrolase, was determined by LC/MS/MS, NMR and GC/MS in male Sprague-Dawley rats. The major metabolites of SC-57461 in rats were the desmethyl metabolite, the hydroxylated metabolite, the N-oxide metabolite, the hydroxylamine metabolite, and the propionic acid metabolite. The N-oxide metabolite was found to be stable in the rat plasma and urine, but was unstable in most organic solvents (methanol, acetonitrile, and methylene chloride, etc.) because of the classic Cope reaction of the N-oxide, which led to the formation of the corresponding hydroxylamine product and acrylic acid. The hydroxylamine metabolite and acrylic acid were reactive in the biomatrix and could not be isolated in the in vivo samples. However, formation of the hydroxylamine metabolite and acrylic acid from the N-oxide metabolite in methylene chloride was verified by NMR. The propionic acid metabolite was found to be the common metabolite shared by SC-57461, N-oxide metabolite, as well as the hydroxylamine metabolite, which suggested a sequential metabolism of SC-57461 in rats.
3.Synthesis of potent leukotriene A(4) hydrolase inhibitors. Identification of 3-[methyl[3-[4-(phenylmethyl)phenoxy]propyl]amino]propanoic acid.
Penning TD;Russell MA;Chen BB;Chen HY;Liang CD;Mahoney MW;Malecha JW;Miyashiro JM;Yu SS;Askonas LJ;Gierse JK;Harding EI;Highkin MK;Kachur JF;Kim SH;Villani-Price D;Pyla EY;Ghoreishi-Haack NS;Smith WG J Med Chem. 2002 Aug 1;45(16):3482-90.
Leukotriene B(4) (LTB(4)) is a potent, proinflammatory mediator involved in the pathogenesis of a number of diseases including inflammatory bowel disease, psoriasis, rheumatoid arthritis, and asthma. The enzyme LTA(4) hydrolase represents an attractive target for pharmacological intervention in these disease states, since the action of this enzyme is the rate-limiting step in the production of LTB(4). Our previous efforts focused on the exploration of a series of analogues related to screening hit SC-22716 (1, 1-[2-(4-phenylphenoxy)ethyl]pyrrolidine) and resulted in the identification of potent, orally active inhibitors such as 2. Additional structure-activity relationship studies around this structural class resulted in the identification of a series of alpha-, beta-, and gamma-amino acid analogues that are potent inhibitors of the LTA(4) hydrolase enzyme and demonstrated good oral activity in a mouse ex vivo whole blood LTB(4) production assay. The efforts leading to the identification of clinical candidate SC-57461A (8d, 3-[methyl[3-[4-(phenylmethyl)phenoxy]propyl]amino]propanoic acid) are described.
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CAS 423169-68-0 SC 57461A

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