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L-371,257

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Chemical compound Pharmaceutical compound
L-371,257
Clinical data
Routes of
administration		By mouth
ATC code
  • None
Identifiers
IUPAC name
  • 1--2-methoxybenzoyl]-4-(2-oxo-2H-3,1-benzoxazin-1(4H)-yl)piperidine
CAS Number
PubChem CID
IUPHAR/BPS
ChemSpider
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC28H33N3O6
Molar mass507.587 g·mol
3D model (JSmol)
SMILES
  • O=C1OCc3ccccc3N1C(CC4)CCN4C(=O)c2ccc(cc2OC)OC5CCN(C(C)=O)CC5
InChI
  • InChI=1S/C28H33N3O6/c1-19(32)29-15-11-22(12-16-29)37-23-7-8-24(26(17-23)35-2)27(33)30-13-9-21(10-14-30)31-25-6-4-3-5-20(25)18-36-28(31)34/h3-8,17,21-22H,9-16,18H2,1-2H3
  • Key:WDERJSQJYIJOPD-UHFFFAOYSA-N
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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. It was one of the first non-peptide oxytocin antagonists developed, and has good oral bioavailability, but poor penetration of the blood–brain barrier, which gives it good peripheral selectivity with few central side effects. Potential applications are likely to be in the treatment of premature labour.

See also

References

  1. Williams PD, Clineschmidt BV, Erb JM, Freidinger RM, Guidotti MT, Lis EV, et al. (November 1995). "1-(1--2-methoxybenzoyl]piperidin-4- yl)-4H-3,1-benzoxazin-2(1H)-one (L-371,257): a new, orally bioavailable, non-peptide oxytocin antagonist". Journal of Medicinal Chemistry. 38 (23): 4634–6. doi:10.1021/jm00023a002. PMID 7473590.
  2. Bell IM, Erb JM, Freidinger RM, Gallicchio SN, Guare JP, Guidotti MT, et al. (June 1998). "Development of orally active oxytocin antagonists: studies on 1-(1--2- methoxybenzoyl]piperidin-4-yl)-1,4-dihydrobenzoxazin-2-one (L-372,662) and related pyridines". Journal of Medicinal Chemistry. 41 (12): 2146–63. doi:10.1021/jm9800797. PMID 9622556.
  3. Kuo MS, Bock MG, Freidinger RM, Guidotti MT, Lis EV, Pawluczyk JM, et al. (November 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. doi:10.1016/S0960-894X(98)00568-X. PMID 9873680.
  4. Williams PD, Bock MG, Evans BE, Freidinger RM, Gallicchio SN, Guidotti MT, et al. (May 1999). "Nonpeptide oxytocin antagonists: analogs of L-371,257 with improved potency". Bioorganic & Medicinal Chemistry Letters. 9 (9): 1311–6. doi:10.1016/S0960-894X(99)00181-X. PMID 10340620.
  5. Wyatt PG, Allen MJ, Chilcott J, Foster A, Livermore DG, Mordaunt JE, et al. (May 2002). "Identification of potent and selective oxytocin antagonists. Part 1: indole and benzofuran derivatives". Bioorganic & Medicinal Chemistry Letters. 12 (10): 1399–404. doi:10.1016/S0960-894X(02)00159-2. PMID 11992786.
  6. Ring RH, Malberg JE, Potestio L, Ping J, Boikess S, Luo B, et al. (April 2006). "Anxiolytic-like activity of oxytocin in male mice: behavioral and autonomic evidence, therapeutic implications". Psychopharmacology. 185 (2): 218–25. doi:10.1007/s00213-005-0293-z. PMID 16418825. S2CID 13647805.
  7. Hawtin SR, Ha SN, Pettibone DJ, Wheatley M (January 2005). "A Gly/Ala switch contributes to high affinity binding of benzoxazinone-based non-peptide oxytocin receptor antagonists". FEBS Letters. 579 (2): 349–56. doi:10.1016/j.febslet.2004.10.108. PMID 15642343. S2CID 38088139.
Oxytocin and vasopressin receptor modulators
Oxytocin
Vasopressin
V1A
V1B
V2
Unsorted
Others
Categories: