In vitro and in vivo pharmacological characterization of ethyl-4-{trans-4-[((2S)-2-hydroxy-3-{4-hydroxy-3[(methylsulfonyl)amino]-phenoxy} propyl) amino]cyclohexyl}benzoate hydrochloride (SAR150640), a new potent and selective human β3-adrenoceptor agonist for the treatment of preterm labor

Journal of Pharmacology and Experimental Therapeutics

Volumn 321, Issue 3, 2007, Pages 1118-1126

  Croci, Tiziano ^a   Cecchi, Roberto ^a   Marini, Pietro ^a   Rouget, Céline ^a   Viviani, Nunzia ^a   Germain, Guy ^f   Guagnini, Fabio ^a   Fradin, Yvon ^c   Descamps, Laurence ^d   Pascal, Marc ^b   Advenier, Charles ^h   Breuiller Fouché, Michelle ^g   Leroy, Marie Josèphe ^g   Bardou, Marc ^e  

^a Centro Ricerche Sanofi Midy SpA   (Italy)

^b SANOFI   (France)

^c Drug Safety Evaluation   (France)

^d DMPK   (France)

^e UNIVERSITÉ DE BOURGOGNE   (France)

^f INRA Institut National de la Recherche Agronomique   (France)

^g INSERM   (France)

^h Inst Anatom des Saints Peres   (France)

Author keywords

[No Author keywords available]

Indexed keywords

4 (3 TERT BUTYLAMINO 2 HYDROXYPROPOXY) 2 BENZIMIDAZOLONE; 4 [4 [[(2) 2 HYDROXY 3 [4 HYDROXY 3 [(METHYLSULFONYL) AMINO] PHENOXY] PROPYL] AMINO] CYCLOHEXYL] BENZOIC ACID; ATOSIBAN; BENZOIC ACID DERIVATIVE; BETA 3 ADRENERGIC RECEPTOR; BETA 3 ADRENERGIC RECEPTOR STIMULATING AGENT; CYCLIC AMP; ETHYL 4 [4 [[(2) 2 HYDROXY 3 [4 HYDROXY 3 [(METHYLSULFONYL) AMINO] PHENOXY] PROPYL] AMINO] CYCLOHEXYL] BENZOATE HYDROCHLORIDE; ISOPRENALINE; MITOGEN ACTIVATED PROTEIN KINASE; OXYTOCIN; PROSTAGLANDIN F2 ALPHA; SALBUTAMOL; SAR 150640; SAR 500400; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL EXPERIMENT; ARTICLE; CALCIUM MOBILIZATION; CONTROLLED STUDY; DOSE RESPONSE; DRUG POTENCY; ENZYME PHOSPHORYLATION; FEMALE; HEART RATE; HUMAN; IN VITRO STUDY; IN VIVO STUDY; ISOLATED HEART; MYOMETRIUM; NEUROBLASTOMA CELL; NONHUMAN; PREMATURE LABOR; PRIORITY JOURNAL; SMOOTH MUSCLE FIBER; UTERUS CONTRACTION;

ADRENERGIC BETA-AGONISTS; ADRENERGIC BETA-ANTAGONISTS; ALBUTEROL; ANIMALS; BENZOATES; BINDING, COMPETITIVE; CELL LINE; CELL LINE, TUMOR; CELLS, CULTURED; CYCLIC AMP; FEMALE; GUANOSINE 5'-O-(3-THIOTRIPHOSPHATE); HUMANS; ISOPROTERENOL; MACACA FASCICULARIS; MOLECULAR STRUCTURE; MYOMETRIUM; OBSTETRIC LABOR, PREMATURE; OXYTOCIN; PREGNANCY; PROPANOLAMINES; RECEPTORS, ADRENERGIC, BETA-3; SULFONAMIDES; TOCOLYTIC AGENTS; TRANSFECTION; UTERINE CONTRACTION; VASOTOCIN;

EID: 34248581635     PISSN: 00223565     EISSN: 15210103     Source Type: Journal    
DOI: 10.1124/jpet.106.119123     Document Type: Article

References (40)

1. Ananth CV, Misra DP, Demissie K, and Smulian JC (2001) Rates of preterm delivery among black women and white women in the United States over two decades: an age-period-cohort analysis. Am J Epidemiol 154:657-665.
2. Andersson RG, Berg G, Johansson SR, and Ryden G (1980) Effects of non-selective and selective β-adrenergic agonists on spontaneous contractions and cyclic AMP levels in myometrial strips from pregnant women. Gynecol Obstet Investig 11:268-293.
3. 3-adrenoceptor in human near-term myometrium. Br J Pharmacol 130:1960-1966.
4. Berg G, Andersson RG, and Ryden G (1983) In vitro study of phosphodiesterase-inhibiting drugs: a complement to β-sympathomimetic drug therapy in premature labor? Am J Obstet Gynecol 145:802-806.
5. Berg G, Andersson RG, and Ryden G (1985) β-adrenergic receptors in human myometrium during pregnancy: changes in the number of receptors after betamimetic treatment. Am J Obstet Gynecol 151:392-396.
6. Berkman ND, Thorp JM Jr, Lohr KN, Carey TS, Hartmann KE, Gavin NI, Hasselblad V, and Idicula AE (2003) Tocolytic treatment for the management of preterm labor: a review of the evidence. Am J Obstet Gynecol 188:1648-1659.
7. 3- receptors. A promising antidiabetic and antiobesity agent. J Med Chem 35:3081-3084.
8. Bradford MM (1976) A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein dye binding. Anal Biochem 72:248-254.
9. 125I]- iodocyanopindolol binding. Gynecol Obstet Investig 24:28-37.
10. Carbonne B, Cabrol D, Clerget MS, and Germain G (1998) Effects of nomegestrol acetate on spontaneous and sulprostone-induced uterine contractions in pregnant cynomolgus monkeys monitored by telemetry. Am J Obstet Gynecol 178:150-155.
11. 3, adrenoceptor-mediated lipolytic responses of adipocytes after long-term norepinephrine infusion. J Pharmacol Exp Ther 265:237-247.
12. Cecchi R, Croci T, Boigegrain R, Boveri S, Baroni M, Boccardi G, Guimbard JP, and Guzzi U (1994) Synthesis and β-adrenergic activity of atypical β-adrenergic phenylethanolaminotetralin stereoisomers. Eur J Med Chem 29:259-267.
13. 2-adrenergic receptor protein in human myometrium with labor. J Clin Endocrinol Metab 88:4997-5001.
14. 50) of an enzymatic reaction. Biochem Pharmacol 22:3099-3108.
15. Chellman GJ, Bee WH, Resendez JC, Meyer JK, Bernal J, Moddrelle DS, Haluska GJ, and Reinheimer TM (2004) Telemetric uterine contraction model in preterm cynomolgus monkeys. Reprod Toxicol 18:285-293.
16. 2 adrenergic agonists and preterm labour: in vitro uterine relaxation effects. Br J Obstet Gynaecol 108:605-609.
17. Doheny HC, Lynch CM, Smith TJ, and Morrison JJ (2005) Functional coupling of beta3-adrenoceptors and large conductance calcium-activated potassium channels in human uterine myocytes. J Clin Endocrinol Metab 90:5786-5796.
18. Dodd JM, Crowther CA, Dare MR, and Middleton P (2006) Oral betamimetics for maintenance therapy after threatened preterm labor. Cochrane Database Syst Rev 25:CD003927.
19. 3-adrenergic receptor. Science (Wash DC) 245:1118-1121.
20. Engelhardt S, Zieger W, Kassubek J, Michel MC, Lohse MJ, and Brodde OE (1997) Tocolytic therapy with fenoterol induces selective down-regulation of β-adrenergic receptors in human myometrium. J Clin Endocrinol Metab 82:1235-1242.
21. Esbenshade TA, Han C, Theroux TL, Granneman JG, and Minneman KP (1992) Coexisting beta-1 and atypical β-adrenergic receptors cause redundant increases in cyclic AMP in human neuroblastoma cells. Mol Pharmacol 42:753-759.
22. 3 adrenergic receptor agonist increases metabolic rate in rhesus monkeys. J Clin Investig 101:2387-2393.
23. Germain G, Lopes P, Cabrol D, Barbe MP, Huneau D, Le Hovezec R, and Sureau C (1986) A comparison of uterine motility in the pregnant and non-pregnant cynomolgus monkey (Macaca fascicularis) and pregnant woman: a manometric and electromyographic study. Acta Physiol Hung 67:95-115.
24. Goldenberg RL and Rouse DJ (1998) Prevention of premature birth. N Engl J Med 339:313-320.
25. Gsell S, Eschenhagen T, Kaspareit G, Nose M, Scholz H, Behrens O, and Wieland T (2000) Apparent up-regulation of stimulatory G-protein alpha subunits in the pregnant human myometrium is mimicked by elevated smoothelin expression. FASEB J 14:17-26.
26. Hollenga C, Brouwer F, and Zaagsma J (1991) Differences in functional cyclic AMP compartments mediating lipolysis by isoprenaline and BRL 37344 in four adipocyte types. Eur J Pharmacol 200:325-330.
27. Konkar AA, Vansal SS, Shams G, Fraundorfer PF, Zheng WP, Nikulin VI, De Los Angeles J, Fertel RH, Miller DD, and Feller DR (1999) β-Adrenoceptor subtype activities of trimetoquinol derivatives: biochemical studies on human β-adrenoceptors expressed in Chinese hamster ovary cells. J Pharmacol Exp Ther 291:875-883.
28. 3-adrenergic receptor agonist, (R)-N-[4-[2-[[2-hydroxy-2-(3-pyridinyl)ethyl] amino] ethyl] phenyl]-4-[4-[4(trifluoromethyl) phenyl] thiazol-2-yl]benzenesulfonamide. J Med Chem 43:3832-3836.
29. 3-adrenoceptor signalling. Br J Pharmacol 114:1045-1051.
30. Nohara A, Ohmichi M, Koike K, Masumoto N, Kobayashi M, Akahane M, Ikegami H, Hirota K, Miyake A, and Murata Y (1996) The role of mitogen-activated protein kinase in oxytocin-induced contraction of uterine smooth muscle in pregnant rat. Biochem Biophys Res Commun 229:938-944.
31. Ohmichi M, Koike K, Nohara A, Kanda Y, Sakamoto Y, Zhang ZX, Hirota K, and Miyake A (1995) Oxytocin stimulates mitogen-activated protein kinase activity in cultured human puerperal uterine myometrial cells. Endocrinology 136:2082-2087.
32. Papatsonis D, Flenady V, Cole S, and Liley H (2005) Oxytocin receptor antagonists for inhibiting preterm labour. Cochrane Database Syst Rev 20:CD004452.
33. Ratkowsky DA and Reedy TJ (1986) Choosing near-linear parameters in the four parameters logistic model radioligands and related assays. Biometrics 42:575-582.
34. Rouget C, Bardou M, Breuiller-Fouche M, Loustalot C, Qi H, Naline E, Croci T, Cabrol D, Advenier C, and Leroy MJ (2005) β3-Adrenoceptor is the predominant β-adrenoceptor subtype in human myometrium and its expression is up-regulated in pregnancy. J Clin Endocrinol Metab 90:1644-1650.
35. 2- adrenoceptor is resistant to desensitisation after sustained agonist stimulation. Br J Pharmacol 141:831-841.
36. Sanborn BM, Ku CY, Shlykov S, and Babich L (2005) Molecular signaling through G-protein-coupled receptors and the control of intracellular calcium in myometrium. J Soc Gynecol Investig 12:479-487.
37. 3-adrenoceptor agonists of differing selectivities. J Pharmacol Exp Ther 285:1084-1095.
38. Slattery MM and Morrison JJ (2002) Preterm delivery. Lancet 360:1489-1497.
39. Strosberg AD (1993) Structure, function, and regulation of adrenergic receptors. Protein Sci 2:1198-1209.
40. 3-adrenoceptor agonists for the treatment of frequent urination and urinary incontinence. J Med Chem 44:1436-1445.