L-368,899

L-368,899
Clinical data
ATC code	None;
Identifiers
	IUPAC name (S)-2-amino-N-((1S,2S,4R)-7,7-dimethyl-1-((4-o-tolylpiperazin-1-ylsulfonyl)methyl)bicyclo[2.2.1]heptan-2-yl)-4-(methylsulfonyl)butanamide;
CAS Number	148927-60-0 ;
PubChem CID	132857;
IUPHAR/BPS	2249;
UNII	ER33G946JT;
CompTox Dashboard (EPA)	DTXSID80933504 ;
Chemical and physical data
Formula	C26H42N4O5S2
Molar mass	554.77 g·mol−1
3D model (JSmol)	Interactive image;
	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;
	(verify)

L-368,899 is a drug used in scientific research which acts as a selective antagonist of the oxytocin receptor, with good selectivity over the related vasopressin receptors.^[1] 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 bonding, 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.^[2]^[3]

References

^ Williams PD, Anderson PS, Ball RG, Bock MG, Carroll L, Chiu SH, Clineschmidt BV, Culberson JC, Erb JM, Evans BE (March 1994). "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 of Medicinal Chemistry. 37 (5): 565–71. doi:10.1021/jm00031a004. PMID 8126695.
^ Boccia ML, Goursaud AP, Bachevalier J, Anderson KD, Pedersen CA (September 2007). "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". Hormones and Behavior. 52 (3): 344–51. doi:10.1016/j.yhbeh.2007.05.009. PMC 2712625. PMID 17583705.
^ Smith AS, Agmo A, Birnie AK, French JA (February 2010). "Manipulation of the oxytocin system alters social behavior and attraction in pair-bonding primates, Callithrix penicillata". Hormones and Behavior. 57 (2): 255–62. doi:10.1016/j.yhbeh.2009.12.004. PMC 2824532. PMID 20025881.

[pmid8126695-1] Williams PD, Anderson PS, Ball RG, Bock MG, Carroll L, Chiu SH, Clineschmidt BV, Culberson JC, Erb JM, Evans BE (March 1994). "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 of Medicinal Chemistry. 37 (5): 565–71. doi:10.1021/jm00031a004. PMID 8126695.

[pmid17583705-2] Boccia ML, Goursaud AP, Bachevalier J, Anderson KD, Pedersen CA (September 2007). "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". Hormones and Behavior. 52 (3): 344–51. doi:10.1016/j.yhbeh.2007.05.009. PMC 2712625. PMID 17583705.

[pmid20025881-3] Smith AS, Agmo A, Birnie AK, French JA (February 2010). "Manipulation of the oxytocin system alters social behavior and attraction in pair-bonding primates, Callithrix penicillata". Hormones and Behavior. 57 (2): 255–62. doi:10.1016/j.yhbeh.2009.12.004. PMC 2824532. PMID 20025881.

[1]

[2]

[3]

See also

References