Open Access Articles- Top Results for L-371,257


File:L-371,257 structure.png
Systematic (IUPAC) name
Clinical data
162042-44-6 7pxY
PubChem CID 6918320
ChemSpider 5293524 7pxN
Chemical data
Formula C28H33N3O6
507.577 g/mol
 14pxN (what is this?)  (verify)

L-371,257 is a compound used in scientific research which acts as a selective antagonist of the oxytocin receptor with over 800x selectivity over the related vasopressin receptors.[1] It was one of the first non-peptide oxytocin antagonists developed,[2][3][4][5] and has good oral bioavailability, but poor penetration of the blood–brain barrier, which gives it good peripheral selectivity with few central side effects.[6] Potential applications are likely to be in the treatment of premature labour.[7]

See also


  1. ^ Williams, PD; Clineschmidt, BV; Erb, JM; Freidinger, RM; Guidotti, MT; Lis, EV; Pawluczyk, JM; Pettibone, DJ et al. (1995). "1-(1-4-(N-acetyl-4-piperidinyl)oxy-2-methoxybenzoylpiperidin-4- yl)-4H-3,1-benzoxazin-2(1H)-one (L-371,257): a new, orally bioavailable, non-peptide oxytocin antagonist". Journal of Medical Chemistry 38 (23): 4634–6. PMID 7473590. doi:10.1021/jm00023a002. 
  2. ^ Bell, IM; Erb, JM; Freidinger, RM; Gallicchio, SN; Guare, JP; Guidotti, MT; Halpin, RA; Hobbs, DW et al. (1998). "Development of orally active oxytocin antagonists: studies on 1-(1-4-1-(2-methyl-1-oxidopyridin-3-ylmethyl)piperidin-4-yloxy-2- methoxybenzoylpiperidin-4-yl)-1,4-dihydrobenzd1,3oxazin-2-one (L-372,662) and related pyridines". Journal of Medical Chemistry 41 (12): 2146–63. PMID 9622556. doi:10.1021/jm9800797. 
  3. ^ Kuo, MS; Bock, MG; Freidinger, RM; Guidotti, MT; Lis, EV; Pawluczyk, JM; Perlow, DS; Pettibone, DJ et al. (1998). "Nonpeptide oxytocin antagonists: potent, orally bioavailable analogs of L-371,257 containing a 1-R-(pyridyl)ethyl ether terminus". Bioorganic & Medicinal Chemistry Letters 8 (21): 3081–6. PMID 9873680. doi:10.1016/S0960-894X(98)00568-X. 
  4. ^ Williams, PD; Bock, MG; Evans, BE; Freidinger, RM; Gallicchio, SN; Guidotti, MT; Jacobson, MA; Kuo, MS et al. (1999). "Nonpeptide oxytocin antagonists: analogs of L-371,257 with improved potency". Bioorganic & Medicinal Chemistry Letters 9 (9): 1311–6. PMID 10340620. doi:10.1016/S0960-894X(99)00181-X. 
  5. ^ Wyatt, PG; Allen, MJ; Chilcott, J; Foster, A; Livermore, DG; Mordaunt, JE; Scicinski, J; Woollard, PM (2002). "Identification of potent and selective oxytocin antagonists. Part 1: indole and benzofuran derivatives". Bioorganic & Medicinal Chemistry Letters 12 (10): 1399–404. PMID 11992786. doi:10.1016/S0960-894X(02)00159-2. 
  6. ^ Ring, RH; Malberg, JE; Potestio, L; Ping, J; Boikess, S; Luo, B; Schechter, LE; Rizzo, S et al. (2006). "Anxiolytic-like activity of oxytocin in male mice: behavioral and autonomic evidence, therapeutic implications". Psychopharmacology 185 (2): 218–25. PMID 16418825. doi:10.1007/s00213-005-0293-z. 
  7. ^ Hawtin, SR; Ha, SN; Pettibone, DJ; Wheatley, M (2005). "A Gly/Ala switch contributes to high affinity binding of benzoxazinone-based non-peptide oxytocin receptor antagonists". FEBS Letters 579 (2): 349–56. PMID 15642343. doi:10.1016/j.febslet.2004.10.108.