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OT-12

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OT-12
Clinical data
Other namesOT-12; OT12
Routes of
administration
Subcutaneous injection[1]
Drug classOxytocin receptor agonist
ATC code
  • None
Identifiers
  • 18-[[(1S)-5-[3-[2-[2-[3-[2-[2-[[2-[(2R)-3-[(2-amino-2-oxoethyl)amino]-2-[[(2S)-1-[(3R,6S,9S,12S,15S)-6-(2-amino-2-oxoethyl)-9-(3-amino-3-oxopropyl)-12-[(2R)-butan-2-yl]-15-[(4-hydroxyphenyl)methyl]-5,8,11,14,17-pentaoxo-1-thia-4,7,10,13,16-pentazacyclohenicosane-3-carbonyl]pyrrolidine-2-carbonyl]amino]-3-oxopropyl]sulfanylacetyl]amino]ethoxy]ethoxy]propanoylamino]ethoxy]ethoxy]propanoylamino]-1-carboxypentyl]amino]-18-oxooctadecanoic acid
PubChem CID
Chemical and physical data
FormulaC82H135N15O24S2
Molar mass1779.18 g·mol−1
3D model (JSmol)
  • CC[C@@H](C)[C@H]1C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@@H](CSCCCCC(=O)N[C@H](C(=O)N1)CC2=CC=C(C=C2)O)C(=O)N3CCC[C@H]3C(=O)N[C@@H](CSCC(=O)NCCOCCOCCC(=O)NCCOCCOCCC(=O)NCCCC[C@@H](C(=O)O)NC(=O)CCCCCCCCCCCCCCCCC(=O)O)C(=O)NCC(=O)N)CC(=O)N)CCC(=O)N
  • InChI=1S/C82H135N15O24S2/c1-3-55(2)74-80(114)92-58(32-33-65(83)99)76(110)93-61(50-66(84)100)77(111)95-63(53-122-48-21-19-26-71(105)91-60(78(112)96-74)49-56-28-30-57(98)31-29-56)81(115)97-39-22-24-64(97)79(113)94-62(75(109)89-51-67(85)101)52-123-54-72(106)88-38-43-121-47-45-119-41-35-69(103)87-37-42-120-46-44-118-40-34-68(102)86-36-20-18-23-59(82(116)117)90-70(104)25-16-14-12-10-8-6-4-5-7-9-11-13-15-17-27-73(107)108/h28-31,55,58-64,74,98H,3-27,32-54H2,1-2H3,(H2,83,99)(H2,84,100)(H2,85,101)(H,86,102)(H,87,103)(H,88,106)(H,89,109)(H,90,104)(H,91,105)(H,92,114)(H,93,110)(H,94,113)(H,95,111)(H,96,112)(H,107,108)(H,116,117)/t55-,58+,59+,60+,61+,62+,63+,64+,74+/m1/s1
  • Key:XYTFBZFZYWSYGY-BAROQLTRSA-N

OT-12 is a long-acting peripherally selective peptide oxytocin receptor agonist.[2][1] It is a potent full agonist of the oxytocin receptor with comparable potency to oxytocin but with greater selectivity for the oxytocin receptor over the vasopressin receptors relative to oxytocin.[2][1] The drug is highly peripherally selective similarly to oxytocin, with a brain-to-plasma ratio of about 1/190 or 0.5%.[1] However, it shows much greater plasma protein binding and consequent metabolic stability compared to oxytocin.[2][1] Whereas oxytocin has a plasma half-life of 2 to 3 minutes, OT-12 shows a terminal half-life with depot subcutaneous injection of 24 hours in rodents.[2][1] It is thought that in humans the half-life of OT-12 by this route would be further much longer and could potentially allow for administration once every 1 to 2 weeks.[1] Despite not crossing into the brain, OT-12 has been found to suppress food intake and decrease body weight when given by subcutaneous injection in rodents.[2][1] The chemical synthesis of OT-12 has been described.[1] OT-12 was first described in the scientific literature by Elsa Pflimlin and colleagues by 2020.[2][1]

See also

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References

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  1. 1 2 3 4 5 6 7 8 9 10 Pflimlin E, Zhou Z, Amso Z, Fu Q, Lee C, Muppiddi A, et al. (January 2020). "Engineering a Potent, Long-Acting, and Periphery-Restricted Oxytocin Receptor Agonist with Anorexigenic and Body Weight Reducing Effects". Journal of Medicinal Chemistry. 63 (1): 382–390. doi:10.1021/acs.jmedchem.9b01862. PMID 31850759.
  2. 1 2 3 4 5 6 Cid-Jofré V, Moreno M, Reyes-Parada M, Renard GM (November 2021). "Role of Oxytocin and Vasopressin in Neuropsychiatric Disorders: Therapeutic Potential of Agonists and Antagonists". International Journal of Molecular Sciences. 22 (21) 12077. doi:10.3390/ijms222112077. PMC 8584779. PMID 34769501. On the other hand, OT-12, a potent and long-lasting OT analog has been shown as a powerful OTR agonist with a promising anorexigenic activity. Incorporating fatty acid moieties onto the backbone peptide of OT, results in low in vitro activity with AVP-Rs, improvement in plasma half-life in mice compared to OT and carbetocin, and a significant reduction in body weight in a mouse model of obesity [177].