Lipo-oxytocin-1

Chemical compound

Lipo-oxytocin-1
Identifiers

IUPAC name [4-[[7-(2-amino-2-oxoethyl)-4-[2-[[1-[(2-amino-2-oxoethyl)amino]-4-methyl-1-oxopentan-2-yl]carbamoyl]pyrrolidine-1-carbonyl]-10-(3-amino-3-oxopropyl)-13-butan-2-yl-19-(hexadecanoylamino)-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentazacycloicos-16-yl]methyl]phenyl] hexadecanoate
PubChem CID	156963489
Chemical and physical data
Formula	C₇₅H₁₂₆N₁₂O₁₄S₂
Molar mass	1484.02 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES CCCCCCCCCCCCCCCC(=O)NC1CSSCC(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC1=O)CC2=CC=C(C=C2)OC(=O)CCCCCCCCCCCCCCC)C(C)CC)CCC(=O)N)CC(=O)N)C(=O)N3CCCC3C(=O)NC(CC(C)C)C(=O)NCC(=O)N
InChI InChI=1S/C75H126N12O14S2/c1-7-10-12-14-16-18-20-22-24-26-28-30-32-36-65(91)80-59-49-102-103-50-60(75(100)87-44-34-35-61(87)73(98)84-56(45-51(4)5)68(93)79-48-64(78)90)85-70(95)58(47-63(77)89)83-69(94)55(42-43-62(76)88)81-74(99)67(52(6)9-3)86-71(96)57(82-72(59)97)46-53-38-40-54(41-39-53)101-66(92)37-33-31-29-27-25-23-21-19-17-15-13-11-8-2/h38-41,51-52,55-61,67H,7-37,42-50H2,1-6H3,(H2,76,88)(H2,77,89)(H2,78,90)(H,79,93)(H,80,91)(H,81,99)(H,82,97)(H,83,94)(H,84,98)(H,85,95)(H,86,96) Key:SEKXRJKQJZKAIR-UHFFFAOYSA-N

Lipo-oxytocin-1 (LOT-1) is a synthetic peptide and derivative of oxytocin that acts as an agonist of the oxytocin receptor.^[1] The lipidation strategy was applied to oxytocin to create a new peptide with improved pharmacokinetics.^[1] LOT-1 consists of oxytocin conjugated with two palmitoyl groups.^[1] After adjusting for molecular weight (LOT-1 is ~1.5x the weight of oxytocin), oxytocin and LOT-1 are equipotent.^[1] In addition, LOT-1 appears to have a significantly longer duration of effect relative to that of oxytocin.^[1] It has yet to be determined whether LOT-1 possesses improved blood-brain-barrier permeability relative to oxytocin.^[1]

References

^ ^a ^b ^c ^d ^e ^f Mizuno A, Cherepanov SM, Kikuchi Y, Fakhrul AA, Akther S, Deguchi K, Yoshihara T, Ishihara K, Shuto S, Higashida H (2015). "Lipo-oxytocin-1, a Novel Oxytocin Analog Conjugated with Two Palmitoyl Groups, Has Long-Lasting Effects on Anxiety-Related Behavior and Social Avoidance in CD157 Knockout Mice". Brain Sci. 5 (1): 3–13. doi:10.3390/brainsci5010003. PMC 4390788. PMID 25612002.

Oxytocin and vasopressin receptor modulators

Oxytocin

Agonists: Peptide: Aspartocin
Carbetocin
Cargutocin
Demoxytocin
Lipo-oxytocin-1
Merotocin
Nacartocin
Oxytocin
PF-06478939
PF-06655075 (PF1)
TGOT
Vasotocin (argiprestocin); Non-peptide: CA7
LIT-001
TC OT 39
WAY-267464
WJ0679

Antagonists: Peptide: Atosiban
Tocinoic acid; Non-peptide: Barusiban
Cligosiban
Epelsiban
Erlosiban
IX-01
L-368,899
L-371,257
L-372,662
Nolasiban
Retosiban
SSR-126768
WAY-162720

Vasopressin

V_1A	Agonists: Felypressin Lypressin Ornipressin Selepressin Terlipressin Vasopressin (argipressin) Vasotocin (argiprestocin) Antagonists: Atosiban Balovaptan Conivaptan FR-218944 JNJ-17079166 JNJ-17308616 LIT-001 LY-307174 PF-184563 Relcovaptan 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 Brezivaptan Nelivaptan ORG-52186 (SCH-740935) TASP-0233278 TASP-0390325 Ligands: TASP-699
V₂	Agonists: Desmopressin Felypressin LIT-001 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: Balovaptan Ribuvaptan RWJ-339489 VMAX-367 VMAX-372 VMAX-382 YM-222546 Other inhibitors: Demeclocycline Lithium (lithium carbonate)