Merotocin

Merotocin

Systematic (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
Identifiers
CAS Number	1190083-57-8
ATC code	None
PubChem	CID 76073634
ChemSpider	34994563
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
Chemical data
Formula	C48H68FN11O12S
Molar mass	1042.183423 g/mol
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
InChI InChI=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 Key:PVVHQWISMVJHFK-NIFJBHDKSA-N

Merotocin (INN) (developmental code name FE-202767), also known as carba-1-(4-FBzlGly⁷)dOT, is a potent (EC₅₀ < 0.1 nM) and highly selective (>1000-fold over the related vasopressin receptors) peptidic agonist of the oxytocin receptor that was derived from oxytocin.^[1][2][3] 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.^[3]

See also

• Carbetocin
• Demoxytocin
• TC OT 39
• WAY-267,464

References

1. Manning, M.; Misicka, A.; Olma, A.; Bankowski, K.; Stoev, S.; Chini, B.; Durroux, T.; Mouillac, B.; Corbani, M.; Guillon, G. (2012). "Oxytocin and Vasopressin Agonists and Antagonists as Research Tools and Potential Therapeutics". Journal of Neuroendocrinology 24 (4): 609–628. doi:10.1111/j.1365-2826.2012.02303.x. ISSN 0953-8194.
2. Yang, Yang; Li, Hao; Ward, Richard; Gao, Linghuan; Wei, Ji-Fu; Xu, Tian-Rui (2014). "Novel oxytocin receptor agonists and antagonists: a patent review (2002 – 2013)". Expert Opinion on Therapeutic Patents 24 (1): 29–46. doi:10.1517/13543776.2014.845168. ISSN 1354-3776.
3. Wiśniewski K, Alagarsamy S, Galyean R, Tariga H, Thompson D, Ly B, Wiśniewska H, Qi S, Croston G, Laporte R, Rivière PJ, Schteingart CD (2014). "New, potent, and selective peptidic oxytocin receptor agonists" (PDF). J. Med. Chem. 57 (12): 5306–17. doi:10.1021/jm500365s. PMID 24874785.

External links

• Pipeline - Ferring Pharmaceuticals
• Merotocin - AdisInsight