SC-57461A | CAS#423169-68-0 | LTA4H inhibitor

MedKoo Cat#: 461890 | Name: SC-57461A

Description:

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

SC-57461 is a potent and specific inhibitor of the leukotriene A4 hydrolase (LTA4H).

Chemical Structure

SC-57461A

CAS#423169-68-0 (HCl)

Theoretical Analysis

MedKoo Cat#: 461890

Name: SC-57461A

CAS#: 423169-68-0 (HCl)

Chemical Formula: C20H26ClNO3

Exact Mass: 0.0000

Molecular Weight: 363.88

Elemental Analysis: C, 66.02; H, 7.20; Cl, 9.74; N, 3.85; O, 13.19

Price and Availability

Size	Price	Availability
25mg	USD 450.00	2 Weeks
100mg	USD 1,250.00	2 Weeks
1g	USD 4,250.00	2 Weeks

Bulk Inquiry

Buy Now

Add to Cart

Related CAS #

No Data

Synonym

SC 57461A; SC-57461A; SC57461A; SC 57461 HCl; SC-57461 HCl; SC57461 HCl; SC 57461 hydrochloride; SC-57461 hydrochloride; SC57461 hydrochloride

IUPAC/Chemical Name

3-((3-(4-benzylphenoxy)propyl)(methyl)amino)propanoic acid hydrochloride

InChi Key

SBBJJLDNKNNWFJ-UHFFFAOYSA-N

InChi Code

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

SMILES Code

O=C(O)CCN(CCCOC1=CC=C(CC2=CC=CC=C2)C=C1)C.[H]Cl

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

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

SC-57461A inhibits LTA4 hydrolase, blocking ionophore-stimulated LTB4 synthesis in whole blood (IC50 = 49 nM) and blocks both hydrolase and aminopeptidase activity in vitro. SC-57461A does not affect other enzymes within the arachidonic acid cascade, such as 5-lipoxygenase, LTC4 synthase, COX-1, and COX-2. In a rat model where peritoneal eicosanoid production is induced by ionophores. SC-57461A exclusively inhibited LTB4 biosynthesis without impacting LTC4 or 6-keto prostaglandin F1α production.

In vitro activity:

SC-57461A is a potent and selective inhibitor of LTA(4) hydrolase. SC-57461A was a potent competitive inhibitor of recombinant human LTA(4) hydrolase when either LTA(4) (IC50 = 2.5 nM, K(i) = 23 nM) or peptide substrates (IC50 = 27 nM) were used. In human whole blood, the IC50 for calcium ionophore-induced LTB(4) production was 49 nM, indicating good cell penetration. Whole blood production of thromboxane B(2) was not affected. Reference: J Pharmacol Exp Ther. 2002 Feb;300(2):577-82. https://pubmed.ncbi.nlm.nih.gov/11805219/

In vivo activity:

SC-57461A is useful to explore the contribution of LTB(4) to various inflammatory diseases. In a rat model of ionophore-induced peritoneal eicosanoid production, SC-57461A inhibited LTB(4) production without affecting LTC(4) or 6-keto-prostaglandin F(1alpha) production. Pretreatment with SC-57461A in a rat reversed passive dermal Arthus model blocked LTB(4) production. Pretreatment with SC-57461 prevented ear edema in mice before exposure to arachidonic acid. Reference: J Pharmacol Exp Ther. 2002 Feb;300(2):583-7. https://pubmed.ncbi.nlm.nih.gov/11805220/

	Solvent	mg/mL	mM
Solubility
	DMF	3.0	8.24
	DMSO	3.0	8.24
	Ethanol	0.3	0.69

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 363.88 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

Formulation protocol:

1. Grenier S, Flamand N, Pelletier J, Naccache PH, Borgeat P, Bourgoin SG. Arachidonic acid activates phospholipase D in human neutrophils; essential role of endogenous leukotriene B4 and inhibition by adenosine A2A receptor engagement. J Leukoc Biol. 2003 Apr;73(4):530-9. doi: 10.1189/jlb.0702371. PMID: 12660228. 2. Askonas LJ, Kachur JF, Villani-Price D, Liang CD, Russell MA, Smith WG. Pharmacological characterization of SC-57461A (3-[methyl[3-[4-(phenylmethyl)phenoxy]propyl]amino]propanoic acid HCl), a potent and selective inhibitor of leukotriene A(4) hydrolase I: in vitro studies. J Pharmacol Exp Ther. 2002 Feb;300(2):577-82. doi: 10.1124/jpet.300.2.577. PMID: 11805219. 3. Kachur JF, Askonas LJ, Villani-Price D, Ghoreishi-Haack N, Won-Kim S, Liang CD, Russell MA, Smith WG. Pharmacological characterization of SC-57461A (3-[methyl[3-[4-(phenylmethyl)phenoxy]propyl]amino]propanoic acid HCl), a potent and selective inhibitor of leukotriene A(4) hydrolase II: in vivo studies. J Pharmacol Exp Ther. 2002 Feb;300(2):583-7. doi: 10.1124/jpet.300.2.583. PMID: 11805220.

In vitro protocol:

In vivo protocol:

1. Kachur JF, Askonas LJ, Villani-Price D, Ghoreishi-Haack N, Won-Kim S, Liang CD, Russell MA, Smith WG. Pharmacological characterization of SC-57461A (3-[methyl[3-[4-(phenylmethyl)phenoxy]propyl]amino]propanoic acid HCl), a potent and selective inhibitor of leukotriene A(4) hydrolase II: in vivo studies. J Pharmacol Exp Ther. 2002 Feb;300(2):583-7. doi: 10.1124/jpet.300.2.583. PMID: 11805220.

1: Gagnon KJ, Lefort N, Poirier SJ, Barnett DA, Surette ME. 5-lipoxygenase- dependent biosynthesis of novel 20:4 n-3 metabolites with anti-inflammatory activity. Prostaglandins Leukot Essent Fatty Acids. 2018 Nov;138:38-44. doi: 10.1016/j.plefa.2018.10.005. Epub 2018 Oct 16. PMID: 30392579. 2: Ye ZN, Wu LY, Liu JP, Chen Q, Zhang XS, Lu Y, Zhou ML, Li W, Zhang ZH, Xia DY, Zhuang Z, Hang CH. Inhibition of leukotriene B4 synthesis protects against early brain injury possibly via reducing the neutrophil-generated inflammatory response and oxidative stress after subarachnoid hemorrhage in rats. Behav Brain Res. 2018 Feb 26;339:19-27. doi: 10.1016/j.bbr.2017.11.011. Epub 2017 Nov 11. PMID: 29133197. 3: Deng B, Lin Y, Ma S, Zheng Y, Yang X, Li B, Yu W, Xu Q, Liu T, Hao C, He R, Ding F. The leukotriene B4-leukotriene B4 receptor axis promotes cisplatin-induced acute kidney injury by modulating neutrophil recruitment. Kidney Int. 2017 Jul;92(1):89-100. doi: 10.1016/j.kint.2017.01.009. Epub 2017 Mar 15. PMID: 28318626. 4: Appiah-Kubi P, Soliman ME. Dual anti-inflammatory and selective inhibition mechanism of leukotriene A4 hydrolase/aminopeptidase: insights from comparative molecular dynamics and binding free energy analyses. J Biomol Struct Dyn. 2016 Nov;34(11):2418-33. doi: 10.1080/07391102.2015.1117991. Epub 2016 Jan 11. PMID: 26555301. 5: Penning TD, Chandrakumar NS, Desai BN, Djuric SW, Gasiecki AF, Liang CD, Miyashiro JM, Russell MA, Askonas LJ, Gierse JK, Harding EI, Highkin MK, Kachur JF, Kim SH, Villani-Price D, Pyla EY, Ghoreishi-Haack NS, Smith WG. Pyrrolidine and piperidine analogues of SC-57461A as potent, orally active inhibitors of leukotriene A(4) hydrolase. Bioorg Med Chem Lett. 2002 Dec 2;12(23):3383-6. doi: 10.1016/s0960-894x(02)00760-6. PMID: 12419366. 6: 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. Synthesis of potent leukotriene A(4) hydrolase inhibitors. Identification of 3-[methyl[3-[4-(phenylmethyl)phenoxy]propyl]amino]propanoic acid. J Med Chem. 2002 Aug 1;45(16):3482-90. doi: 10.1021/jm0200916. PMID: 12139459. 7: Kachur JF, Askonas LJ, Villani-Price D, Ghoreishi-Haack N, Won-Kim S, Liang CD, Russell MA, Smith WG. Pharmacological characterization of SC-57461A (3-[methyl[3-[4-(phenylmethyl)phenoxy]propyl]amino]propanoic acid HCl), a potent and selective inhibitor of leukotriene A(4) hydrolase II: in vivo studies. J Pharmacol Exp Ther. 2002 Feb;300(2):583-7. doi: 10.1124/jpet.300.2.583. PMID: 11805220. 8: Askonas LJ, Kachur JF, Villani-Price D, Liang CD, Russell MA, Smith WG. Pharmacological characterization of SC-57461A (3-[methyl[3-[4-(phenylmethyl)phenoxy]propyl]amino]propanoic acid HCl), a potent and selective inhibitor of leukotriene A(4) hydrolase I: in vitro studies. J Pharmacol Exp Ther. 2002 Feb;300(2):577-82. doi: 10.1124/jpet.300.2.577. PMID: 11805219. 9: Penning TD. Inhibitors of leukotriene A4 (LTA4) hydrolase as potential anti- inflammatory agents. Curr Pharm Des. 2001 Feb;7(3):163-79. doi: 10.2174/1381612013398248. PMID: 11311111.