Merotocin

{{Short description|Chemical compound}}

{{Drugbox

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| IUPAC_name = (3R,6S,9S,12S,15S)-6-(2-Amino-2-oxoethyl)-N-[2-[[(2S)-1-[(2-amino-2-oxoethyl)amino]-4-methyl-1-oxopentan-2-yl]amino]-2-oxoethyl]-9-(3-amino-3-oxopropyl)-12-[(2S)-butan-2-yl]-N-[(4-fluorophenyl)methyl]-15-[(4-hydroxyphenyl)methyl]-5,8,11,14,17-pentaoxo-1-thia-4,7,10,13,16-pentazacycloicosane-3-carboxamide

| image = Merotocin.svg

| width = 250

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| pregnancy_AU =

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| CAS_number = 1190083-57-8

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| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = UW3ON116CO

| ATC_prefix = None

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| PubChem = 76073634

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| C=48 | H=68 | F=1 | N=11 | O=12 | S=1

| ChemSpiderID = 34994563

| smiles = CC[C@H](C)[C@H]1C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@@H](CSCCCC(=O)N[C@H](C(=O)N1)Cc2ccc(cc2)O)C(=O)N(Cc3ccc(cc3)F)CC(=O)N[C@@H](CC(C)C)C(=O)NCC(=O)N)CC(=O)N)CCC(=O)N

| StdInChI = 1S/C48H68FN11O12S/c1-5-27(4)42-47(71)56-32(16-17-37(50)62)44(68)57-35(21-38(51)63)45(69)58-36(25-73-18-6-7-40(65)54-34(46(70)59-42)20-28-10-14-31(61)15-11-28)48(72)60(23-29-8-12-30(49)13-9-29)24-41(66)55-33(19-26(2)3)43(67)53-22-39(52)64/h8-15,26-27,32-36,42,61H,5-7,16-25H2,1-4H3,(H2,50,62)(H2,51,63)(H2,52,64)(H,53,67)(H,54,65)(H,55,66)(H,56,71)(H,57,68)(H,58,69)(H,59,70)/t27-,32-,33-,34-,35-,36-,42-/m0/s1

| StdInChIKey = PVVHQWISMVJHFK-NIFJBHDKSA-N

| synonyms = N-(4-Sulfanylbutanoyl)-L-tyrosyl-L-isoleucyl-L-glutaminyl-L-asparaginyl-L-cysteinyl-N-[(4-fluorophenyl)methyl]glycyl-L-leucylglycinamide cyclic (1-5)-thioether

}}

Merotocin (INN; developmental code FE-202767; also known as carba-1-(4-FBzlGly⁷)dOT) is a peptidic agonist of the oxytocin receptor that was derived from oxytocin.{{cite journal | vauthors = Manning M, Misicka A, Olma A, Bankowski K, Stoev S, Chini B, Durroux T, Mouillac B, Corbani M, Guillon G | title = Oxytocin and vasopressin agonists and antagonists as research tools and potential therapeutics | journal = Journal of Neuroendocrinology | volume = 24 | issue = 4 | pages = 609–28 | year = 2012 | pmid = 22375852 | pmc = 3490377 | doi = 10.1111/j.1365-2826.2012.02303.x }}{{cite journal | vauthors = Yang Y, Li H, Ward R, Gao L, Wei JF, Xu TR | title = Novel oxytocin receptor agonists and antagonists: a patent review (2002 - 2013) | journal = Expert Opinion on Therapeutic Patents | volume = 24 | issue = 1 | pages = 29–46 | year = 2014 | pmid = 24094047 | doi = 10.1517/13543776.2014.845168 | s2cid = 10584554 }}{{cite journal | vauthors = Wiśniewski K, Alagarsamy S, Galyean R, Tariga H, Thompson D, Ly B, Wiśniewska H, Qi S, Croston G, Laporte R, Rivière PJ, Schteingart CD | title = New, potent, and selective peptidic oxytocin receptor agonists | journal = J. Med. Chem. | volume = 57 | issue = 12 | pages = 5306–17 | year = 2014 | pmid = 24874785 | doi = 10.1021/jm500365s | url = https://www.researchgate.net/publication/262787818 }} It is under development by Ferring Pharmaceuticals for the treatment of preterm mothers with lactation failure requiring lactation support, and is in phase II clinical trials for this indication. Merotocin is potent (EC₅₀ < 0.1 nM) and highly selective (>1000-fold over the related vasopressin receptors).