L-368,899: Difference between revisions
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Entranced98 (talk | contribs) Importing Wikidata short description: "Chemical compound" |
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{{Short description|Chemical compound}} |
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{{Drugbox |
{{Drugbox |
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| Watchedfields = changed |
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| verifiedrevid = |
| verifiedrevid = 451607732 |
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| 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 |
| 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 |
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| image = L-368, |
| image = L-368,899.svg |
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| width = |
| width = 250 |
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<!--Clinical data--> |
<!--Clinical data--> |
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| tradename = |
| tradename = |
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| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> |
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> |
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| pregnancy_US = <!-- A / B |
| pregnancy_US = <!-- A / B / C / D / X --> |
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| pregnancy_category = |
| pregnancy_category = |
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| legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled--> |
| legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled--> |
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| legal_CA = <!-- Schedule I, II, III, IV, V, VI, VII, VIII --> |
| legal_CA = <!-- Schedule I, II, III, IV, V, VI, VII, VIII --> |
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| legal_UK = <!-- GSL, P, POM, CD, or Class A, B, C --> |
| legal_UK = <!-- GSL, P, POM, CD, or Class A, B, C --> |
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| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V --> |
| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V --> |
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| legal_status = |
| legal_status = |
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| routes_of_administration = |
| routes_of_administration = |
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<!--Pharmacokinetic data--> |
<!--Pharmacokinetic data--> |
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| bioavailability = |
| bioavailability = |
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| protein_bound = |
| protein_bound = |
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| metabolism = |
| metabolism = |
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| elimination_half-life = |
| elimination_half-life = |
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| excretion = |
| excretion = |
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<!--Identifiers--> |
<!--Identifiers--> |
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| IUPHAR_ligand = 2249 |
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| CAS_number_Ref = {{cascite|correct|??}} |
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| CAS_number = 148927-60-0 |
| CAS_number = 148927-60-0 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = ER33G946JT |
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| PubChem = 132857 |
| PubChem = 132857 |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| DrugBank = |
| DrugBank = |
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<!--Chemical data--> |
<!--Chemical data--> |
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| chemical_formula = |
| chemical_formula = |
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| C=26 | H=42 | N=4 | O=5 | S=2 |
| C=26 | H=42 | N=4 | O=5 | S=2 |
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| molecular_weight = 554.260 g/mol |
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| 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 |
| 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 |
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}} |
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'''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 | |
'''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> |
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==See also== |
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* [[Atosiban]] |
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{{reflist}} |
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* [[Barusiban]] |
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* [[Epelsiban]] |
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* [[L-371,257]] |
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* [[Retosiban]] |
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==References== |
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{{Neuropeptide agonists and antagonists}} |
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{{Reflist|2}} |
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{{Oxytocin and vasopressin receptor modulators}} |
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[[Category:Oxytocin receptor antagonists]] |
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{{systemic-hormonal-drug-stub}} |
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[[ |
[[Category:Tocolytics]] |
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[[Category:2-Tolyl compounds]] |