View source for L-368,899

{{Short description|Chemical compound}}
{{Drugbox
| Watchedfields = changed
| verifiedrevid = 451607732
| IUPAC_name = (''S'')-2-amino-''N''-((1''S'',2''S'',4''R'')-7,7-dimethyl-1-((4-''o''-tolylpiperazin-1-ylsulfonyl)methyl)bicyclo[2.2.1]heptan-2-yl)-4-(methylsulfonyl)butanamide
| image = L-368,899.svg
| width = 250
<!--Clinical data-->
| tradename =
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
| pregnancy_US = <!-- A / B / C / D / X -->
| pregnancy_category =
| legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled-->
| legal_CA = <!-- Schedule I, II, III, IV, V, VI, VII, VIII -->
| legal_UK = <!-- GSL, P, POM, CD, or Class A, B, C -->
| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V -->
| legal_status =
| routes_of_administration =
<!--Pharmacokinetic data-->
| bioavailability =
| protein_bound =
| metabolism =
| elimination_half-life =
| excretion =
<!--Identifiers-->
| IUPHAR_ligand = 2249
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 148927-60-0
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = ER33G946JT
| ATC_prefix = None
| ATC_suffix =
| ATC_supplemental =
| PubChem = 132857
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank =
<!--Chemical data-->
| chemical_formula =
| C=26 | H=42 | N=4 | O=5 | S=2
| smiles = CC1(C)[C@@]2(CS(N3CCN(C4=CC=CC=C4C)CC3)(=O)=O)CC[C@@H]1C[C@@H]2NC([C@H](CCS(C)(=O)=O)N)=O
}}
'''L-368,899''' is a drug used in scientific research which acts as a selective [[Antagonist (pharmacology)|antagonist]] of the [[oxytocin receptor]], with good selectivity over the related [[vasopressin receptor]]s.<ref name="pmid8126695">{{cite journal |vauthors=Williams PD, Anderson PS, Ball RG, Bock MG, Carroll L, Chiu SH, Clineschmidt BV, Culberson JC, Erb JM, Evans BE |title=1-((7,7-Dimethyl-2(S)-(2(S)-amino-4-(methylsulfonyl)butyramido)bicyclo [2.2.1]-heptan-1(S)-yl)methyl)sulfonyl)-4-(2-methylphenyl)piperaz ine (L-368,899): an orally bioavailable, non-peptide oxytocin antagonist with potential utility for managing preterm labor |journal=Journal of Medicinal Chemistry |volume=37 |issue=5 |pages=565–71 |date=March 1994 |pmid=8126695 |doi= 10.1021/jm00031a004}}</ref> Unlike related drugs such as the peripherally selective [[L-371,257]], the oral bioavailabity is high and the brain penetration of L-368,899 is rapid, with selective accumulation in areas of the [[limbic system]]. This makes it a useful tool for investigating the centrally mediated roles of oxytocin, such as in social behaviour and [[pair bond]]ing, and studies in primates have shown L-368,899 to reduce a number of behaviours such as food sharing, sexual activity and caring for infants, demonstrating the importance of oxytocinergic signalling in mediating these important social behaviours.<ref name="pmid17583705">{{cite journal |vauthors=Boccia ML, Goursaud AP, Bachevalier J, Anderson KD, Pedersen CA |title=Peripherally administered non-peptide oxytocin antagonist, L368,899, accumulates in limbic brain areas: a new pharmacological tool for the study of social motivation in non-human primates |journal=Hormones and Behavior |volume=52 |issue=3 |pages=344–51 |date=September 2007 |pmid=17583705 |pmc=2712625 |doi=10.1016/j.yhbeh.2007.05.009 }}</ref><ref name="pmid20025881">{{cite journal |vauthors=Smith AS, Agmo A, Birnie AK, French JA |title=Manipulation of the oxytocin system alters social behavior and attraction in pair-bonding primates, Callithrix penicillata |journal=Hormones and Behavior |volume=57 |issue=2 |pages=255–62 |date=February 2010 |pmid=20025881 |pmc=2824532 |doi=10.1016/j.yhbeh.2009.12.004 }}</ref>
==See also==
* [[Atosiban]]
* [[Barusiban]]
* [[Epelsiban]]
* [[L-371,257]]
* [[Retosiban]]
==References==
{{Reflist|2}}
{{Oxytocin and vasopressin receptor modulators}}
[[Category:Oxytocin receptor antagonists]]
[[Category:Phenylpiperazines]]
[[Category:Tocolytics]]
[[Category:2-Tolyl compounds]]