WARNING: This product is for research use only, not for human or veterinary use.
Hodoodo CAT#: H530419
CAS#: 198279-45-7
Description: J-104132, also known as L-753037, is a potetn and selective endothelin A/B receptor antagonist potentially for the treatment of heart failure. J-104132 has Ki: cloned human ETA = 0.034 nM; cloned human ETB = 0.104 nM. In vitro, J-104132 is a potent antagonist of ET-1-induced accumulation of [3H]inositol phosphates in Chinese hamster ovary cells stably expressing cloned human ETA receptors (IC50 = 0.059 nM). Pretreatment with J-104132 prevents the lethal response to ET-1 when administered i.v. (ED50 = 0.045 mg/kg) or p.o. in fed animals (ED50 = 0.35 mg/kg). J-104132 is an excellent pharmacological tool to explore the therapeutic use of a mixed ETA/ETB receptor antagonist.
Hodoodo Cat#: H530419
Name: J-104132
CAS#: 198279-45-7
Chemical Formula: C31H33NO7
Exact Mass: 531.23
Molecular Weight: 531.605
Elemental Analysis: C, 70.04; H, 6.26; N, 2.63; O, 21.07
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Synonym: J-104132; J104132; J 104132; L-753037; L 753037; L753037.
IUPAC/Chemical Name: (5S,6R,7R)-5-(benzo[d][1,3]dioxol-5-yl)-2-butyl-7-(2-((S)-2-carboxypropyl)-4-methoxyphenyl)-6,7-dihydro-5H-cyclopenta[b]pyridine-6-carboxylic acid
InChi Key: IUHMIOAKWHUFKU-YINIXLNUSA-N
InChi Code: InChI=1S/C31H33NO7/c1-4-5-6-20-8-10-23-26(18-7-12-24-25(15-18)39-16-38-24)28(31(35)36)27(29(23)32-20)22-11-9-21(37-3)14-19(22)13-17(2)30(33)34/h7-12,14-15,17,26-28H,4-6,13,16H2,1-3H3,(H,33,34)(H,35,36)/t17-,26-,27-,28+/m0/s1
SMILES Code: O=C([C@@H]1[C@@H](C2=CC=C(OCO3)C3=C2)C4=CC=C(CCCC)N=C4[C@H]1C5=CC=C(OC)C=C5C[C@@H](C(O)=O)C)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: >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
More Info:
| Biological target: | |
| In vitro activity: | |
| In vivo activity: |
The following data is based on the product molecular weight 531.61 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: | |
| In vitro protocol: | |
| In vivo protocol: |
1: Kitada K, Yui N, Mori T, Ohkita M, Matsumura Y. Vasoprotective effects of an endothelin receptor antagonist in ovariectomized female rats. Life Sci. 2014 Nov 24;118(2):379-85. doi: 10.1016/j.lfs.2014.01.009. PubMed PMID: 24468711.
2: Kitada K, Yui N, Koyama M, Kimura K, Suzuki R, Tanaka R, Mori T, Ohkita M, Matsumura Y. Endothelin ETB receptor is involved in sex differences in the development of balloon injury-induced neointimal formation. J Pharmacol Exp Ther. 2011 Feb;336(2):533-9. doi: 10.1124/jpet.109.165308. PubMed PMID: 21075838.
3: Kitada K, Yui N, Matsumoto C, Mori T, Ohkita M, Matsumura Y. Inhibition of endothelin ETB receptor system aggravates neointimal hyperplasia after balloon injury of rat carotid artery. J Pharmacol Exp Ther. 2009 Dec;331(3):998-1004. doi: 10.1124/jpet.109.157065. PubMed PMID: 19737855.
4: Homma N, Nagaoka T, Morio Y, Ota H, Gebb SA, Karoor V, McMurtry IF, Oka M. Endothelin-1 and serotonin are involved in activation of RhoA/Rho kinase signaling in the chronically hypoxic hypertensive rat pulmonary circulation. J Cardiovasc Pharmacol. 2007 Dec;50(6):697-702. PubMed PMID: 18091588.
5: Tani T, Gram LK, Arakawa H, Kikuchi A, Chiba M, Ishii Y, Steffansen B, Tamai I. Involvement of organic anion transporting polypeptide 1a5 (Oatp1a5) in the intestinal absorption of endothelin receptor antagonist in rats. Pharm Res. 2008 May;25(5):1085-91. PubMed PMID: 17957449.
6: Kamata K, Kanie N, Matsumoto T, Kobayashi T. Endothelin-1-induced impairment of endothelium-dependent relaxation in aortas isolated from controls and diabetic rats. J Cardiovasc Pharmacol. 2004 Nov;44 Suppl 1:S186-90. PubMed PMID: 15838275.
7: Krause SM, Clayton FC, Williams DL Jr. Myocardial protection with the non-selective endothelin receptor antagonist L-753,037 following acute coronary artery occlusion in the dog. J Cardiovasc Pharmacol. 2004 Feb;43(2):214-21. PubMed PMID: 14716208.
8: Kobayashi N, Tani T, Hisaka A, Hara K, Yasumori T. Hepatobiliary transport of a nonpeptidic endothelin antagonist, (+)-(5S,6R,7R)-2-butyl-7-[2((2S)-2-carboxypropyl)-4-methoxyphenyl]-5-(3,4-methyle nedioxyphenyl) cyclopentenol[1,2-b]pyridine-6-carboxylic acid: uptake by isolated rat hepatocytes and canalicular membrane vesicles. Pharm Res. 2003 Jan;20(1):89-95. PubMed PMID: 12608541.
9: Kanie N, Kamata K. Effects of chronic administration of the novel endothelin antagonist J-104132 on endothelial dysfunction in streptozotocin-induced diabetic rat. Br J Pharmacol. 2002 Apr;135(8):1935-42. PubMed PMID: 11959796; PubMed Central PMCID: PMC1573322.
10: Aleksic S, Szabo Z, Scheffel U, Ravert HT, Mathews WB, Kerenyi L, Rauseo PA, Gibson RE, Burns HD, Dannals RF. In vivo labeling of endothelin receptors with [(11)C]L-753,037: studies in mice and a dog. J Nucl Med. 2001 Aug;42(8):1274-80. PubMed PMID: 11483691.
11: Tadano K, Suzuki J, Hanada K, Nakao M, Nakao R, Uehara S, Ohta H, Miyauchi T, Nishikibe M. Pathophysiological roles of endogenous endothelin-1 in dogs with chronic heart failure produced by rapid right ventricular pacing. J Pharmacol Exp Ther. 2001 Aug;298(2):729-36. PubMed PMID: 11454937.
12: Bray ML, Gorbacheva D, Jahansouz H, Kaufman MJ, Ishikawa K, Harada N, Suzuki K. Rate and equilibrium constants for the epimerization of the endothelin receptor antagonist J-104,132 in aqueous solution. Chem Pharm Bull (Tokyo). 2001 Jan;49(1):1-4. PubMed PMID: 11201209.
13: Suresh DP, Lamba S, Abraham WT. New developments in heart failure: role of endothelin and the use of endothelin receptor antagonists. J Card Fail. 2000 Dec;6(4):359-68. Review. PubMed PMID: 11145761.
14: Ikeda T, Ohta H, Okada M, Kawai N, Nakao R, Siegl PK, Kobayashi T, Miyauchi T, Nishikibe M. Antihypertensive effects of a mixed endothelin-A- and -B-receptor antagonist, J-104132, were augmented in the presence of an AT1 -receptor antagonist, MK-954. J Cardiovasc Pharmacol. 2000 Nov;36(5 Suppl 1):S337-41. PubMed PMID: 11078414.
15: Shen YT, Buie PS, Lynch JJ, Krause SM, Ma XL. Chronic therapy with an ET(A/B) receptor antagonist in conscious dogs during progression of congestive heart failure. Intracellular Ca(2+) regulation and nitric oxide mediated coronary relaxation. Cardiovasc Res. 2000 Nov;48(2):332-45. PubMed PMID: 11054479.
16: J 104132. L 753037. Drugs R D. 1999 Jul;2(1):26-7. PubMed PMID: 10610293.
17: Zhao JJ, Xie I, Rogers JD. Determination of L-753,037 in human plasma by liquid chromatography/turbo ionspray tandem mass spectrometry. J Mass Spectrom. 1999 Oct;34(10):1018-27. PubMed PMID: 10510424.
18: Ikeda T, Ohta H, Okada M, Kawai N, Nakao R, Siegl PK, Kobayashi T, Maeda S, Miyauchi T, Nishikibe M. Pathophysiological roles of endothelin-1 in Dahl salt-sensitive hypertension. Hypertension. 1999 Sep;34(3):514-9. PubMed PMID: 10489403.
19: Nishikibe M, Ohta H, Okada M, Ishikawa K, Hayama T, Fukuroda T, Noguchi K, Saito M, Kanoh T, Ozaki S, Kamei T, Hara K, William D, Kivlighn S, Krause S, Gabel R, Zingaro G, Nolan N, O'Brien J, Clayton F, Lynch J, Pettibone D, Siegl P. Pharmacological properties of J-104132 (L-753,037), a potent, orally active, mixed ETA/ETB endothelin receptor antagonist. J Pharmacol Exp Ther. 1999 Jun;289(3):1262-70. PubMed PMID: 10336515.
