Merotocin

Merotocin
Clinical data

ATC code	None
Identifiers
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
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
CAS Number	1190083-57-8
PubChem CID	76073634
ChemSpider	34994563
Chemical and physical data
Formula	C₄₈H₆₈FN₁₁O₁₂S
Molar mass	1042.183423 g/mol
3D model (JSmol)	Interactive image
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 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] Merotocin is potent (EC₅₀ < 0.1 nM) and highly selective (>1000-fold over the related vasopressin receptors).

References

↑ 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): 609–28. PMC 3490377 . PMID 22375852. doi:10.1111/j.1365-2826.2012.02303.x.
↑ Yang Y, Li H, Ward R, Gao L, Wei JF, Xu TR (2014). "Novel oxytocin receptor agonists and antagonists: a patent review (2002 - 2013)". Expert Opinion on Therapeutic Patents. 24 (1): 29–46. PMID 24094047. doi:10.1517/13543776.2014.845168.
1 2 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. PMID 24874785. doi:10.1021/jm500365s.

V_1A	Agonists: Felypressin Lypressin Ornipressin Selepressin Terlipressin Vasopressin (argipressin) Vasotocin (argiprestocin) Antagonists: Atosiban Conivaptan FR-218944 JNJ-17079166 JNJ-17308616 LY-307174 PF-184563 Relcovaptan RG7314 SRX246 SRX251 TC OT 39 WAY-267464 YM-218 YM-471 YM-35471
V_1B	Agonists: Desmopressin Felypressin Lypressin Ornipressin Terlipressin Vasopressin (argipressin) Vasotocin (argiprestocin) Antagonists: ABT-436 ABT-558 Nelivaptan ORG-52186 (SCH-740935) TASP-0233278 TASP-0390325 TS-121 Ligands: TASP-699
V₂	Agonists: Desmopressin Felypressin Lypressin Ornipressin TC OT 39 Terlipressin Vasopressin (argipressin) Vasotocin (argiprestocin) Antagonists: Conivaptan JNJ-17079166 Lixivaptan Mozavaptan RWJ-351647 Satavaptan Tolvaptan YM-471 YM-35471
Unsorted	Antagonists: Ribuvaptan RWJ-339489 VMAX-367 VMAX-372 VMAX-382 YM-222546 Other inhibitors: Demeclocycline Lithium (lithium carbonate)

Others

See also: Receptor/signaling modulators; Signaling peptide/protein receptor modulators

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