oxytocin   Click here for help

GtoPdb Ligand ID: 2174

Abbreviated name: OT
Synonyms: Otx | Pitocin® | Syntocinon®
Approved drug
oxytocin is an approved drug (FDA (1980))
Compound class: Endogenous peptide in human, mouse or rat
Comment: Endogenous oxytocin is a hormone and neuropeptide, which plays a role in social bonding, sexual reproduction and is required during and after childbirth. Purified oxytocin is used clinically.
Species: Human, Mouse, Rat
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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species

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2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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Canonical SMILES CCC(C1NC(=O)C(Cc2ccc(cc2)O)NC(=O)C(N)CSSCC(NC(=O)C(NC(=O)C(NC1=O)CCC(=O)N)CC(=O)N)C(=O)N1CCCC1C(=O)NC(C(=O)NCC(=O)N)CC(C)C)C
Isomeric SMILES CC[C@@H]([C@@H]1NC(=O)[C@H](Cc2ccc(cc2)O)NC(=O)[C@@H](N)CSSC[C@H](NC(=O)[C@@H](NC(=O)[C@@H](NC1=O)CCC(=O)N)CC(=O)N)C(=O)N1CCC[C@H]1C(=O)N[C@H](C(=O)NCC(=O)N)CC(C)C)C
InChI InChI=1S/C43H66N12O12S2/c1-5-22(4)35-42(66)49-26(12-13-32(45)57)38(62)51-29(17-33(46)58)39(63)53-30(20-69-68-19-25(44)36(60)50-28(40(64)54-35)16-23-8-10-24(56)11-9-23)43(67)55-14-6-7-31(55)41(65)52-27(15-21(2)3)37(61)48-18-34(47)59/h8-11,21-22,25-31,35,56H,5-7,12-20,44H2,1-4H3,(H2,45,57)(H2,46,58)(H2,47,59)(H,48,61)(H,49,66)(H,50,60)(H,51,62)(H,52,65)(H,53,63)(H,54,64)/t22-,25-,26-,27-,28-,29-,30-,31-,35-/m0/s1
InChI Key XNOPRXBHLZRZKH-DSZYJQQASA-N
References
1. Akerlund M, Bossmar T, Brouard R, Kostrzewska A, Laudanski T, Lemancewicz A, Serradeil-Le Gal C, Steinwall M. (1999)
Receptor binding of oxytocin and vasopressin antagonists and inhibitory effects on isolated myometrium from preterm and term pregnant women.
Br J Obstet Gynaecol, 106 (10): 1047-53. [PMID:10519430]
2. Cheng LL, Stoev S, Manning M, Derick S, Pena A, Mimoun MB, Guillon G. (2004)
Design of potent and selective agonists for the human vasopressin V1b receptor based on modifications of [deamino-cys1]arginine vasopressin at position 4.
J Med Chem, 47: 2375-2388. [PMID:15084136]
3. Chini B, Mouillac B, Ala Y, Balestre MN, Trumpp-Kallmeyer S, Hoflack J, Elands J, Hibert M, Manning M, Jard S et al.. (1995)
Tyr115 is the key residue for determining agonist selectivity in the V1a vasopressin receptor.
EMBO J, 14 (10): 2176-82. [PMID:7774575]
4. Chini B, Mouillac B, Balestre MN, Trumpp-Kallmeyer S, Hoflack J, Hibert M, Andriolo M, Pupier S, Jard S, Barberis C. (1996)
Two aromatic residues regulate the response of the human oxytocin receptor to the partial agonist arginine vasopressin.
FEBS Lett, 397 (2-3): 201-6. [PMID:8955347]
5. Cirillo R, Gillio Tos E, Schwarz MK, Quattropani A, Scheer A, Missotten M, Dorbais J, Nichols A, Borrelli F, Giachetti C et al.. (2003)
Pharmacology of (2S,4Z)-N-[(2S)-2-hydroxy-2-phenylethyl]-4-(methoxyimino) -1-[(2'-methyl[1,1'-biphenyl]-4-yl)carbonyl]-2-pyrrolidinecarboxamide, a new potent and selective nonpeptide antagonist of the oxytocin receptor.
J Pharmacol Exp Ther, 306 (1): 253-61. [PMID:12660315]
6. Cotte N, Balestre MN, Aumelas A, Mahé E, Phalipou S, Morin D, Hibert M, Manning M, Durroux T, Barberis C et al.. (2000)
Conserved aromatic residues in the transmembrane region VI of the V1a vasopressin receptor differentiate agonist vs. antagonist ligand binding.
Eur J Biochem, 267 (13): 4253-63. [PMID:10866830]
7. Derick S, Cheng LL, Voirol MJ, Stoev S, Giacomini M, Wo NC, Szeto HH, Ben Mimoun M, Andres M, Gaillard RC et al.. (2002)
[1-deamino-4-cyclohexylalanine] arginine vasopressin: a potent and specific agonist for vasopressin V1b receptors.
Endocrinology, 143 (12): 4655-64. [PMID:12446593]
8. Griffante C, Green A, Curcuruto O, Haslam CP, Dickinson BA, Arban R. (2005)
Selectivity of d[Cha4]AVP and SSR149415 at human vasopressin and oxytocin receptors: evidence that SSR149415 is a mixed vasopressin V1b/oxytocin receptor antagonist.
Br J Pharmacol, 146: 744-751. [PMID:16158071]
9. Jasper JR, Harrell CM, O'Brien JA, Pettibone DJ. (1995)
Characterization of the human oxytocin receptor stably expressed in 293 human embryonic kidney cells.
Life Sci, 57 (24): 2253-61. [PMID:7475979]
10. Kimura T, Makino Y, Saji F, Takemura M, Inoue T, Kikuchi T, Kubota Y, Azuma C, Nobunaga T, Tokugawa Y et al.. (1994)
Molecular characterization of a cloned human oxytocin receptor.
Eur J Endocrinol, 131 (4): 385-90. [PMID:7921228]
11. Nakamura S, Yamamura Y, Itoh S, Hirano T, Tsujimae K, Aoyama M, Kondo K, Ogawa H, Shinohara T, Kan K et al.. (2000)
Characterization of a novel nonpeptide vasopressin V(2)-agonist, OPC-51803, in cells transfected human vasopressin receptor subtypes.
Br J Pharmacol, 129 (8): 1700-6. [PMID:10780976]
12. Pena A, Murat B, Trueba M, Ventura MA, Wo NC, Szeto HH, Cheng LL, Stoev S, Guillon G, Manning M. (2007)
Design and synthesis of the first selective agonists for the rat vasopressin V(1b) receptor: based on modifications of deamino-[Cys1]arginine vasopressin at positions 4 and 8.
J Med Chem, 50: 835-847. [PMID:17300166]
13. Phalipou S, Cotte N, Carnazzi E, Seyer R, Mahe E, Jard S, Barberis C, Mouillac B. (1997)
Mapping peptide-binding domains of the human V1a vasopressin receptor with a photoactivatable linear peptide antagonist.
J Biol Chem, 272 (42): 26536-44. [PMID:9334232]
14. Saito M, Tahara A, Sugimoto T. (1997)
1-desamino-8-D-arginine vasopressin (DDAVP) as an agonist on V1b vasopressin receptor.
Biochem Pharmacol, 53: 1711-1717. [PMID:9264324]
15. Serradeil-Le Gal C, Raufaste D, Double-Cazanave E, Guillon G, Garcia C, Pascal M, Maffrand JP. (2000)
Binding properties of a selective tritiated vasopressin V2 receptor antagonist, [H]-SR 121463.
Kidney Int, 58 (4): 1613-22. [PMID:11012895]
16. Tahara A, Saito M, Sugimoto T, Tomura Y, Wada K, Kusayama T, Tsukada J, Ishii N, Yatsu T, Uchida W et al.. (1998)
Pharmacological characterization of YM087, a potent, nonpeptide human vasopressin V1A and V2 receptor antagonist.
Naunyn Schmiedebergs Arch Pharmacol, 357 (1): 63-9. [PMID:9459574]
17. Tahara A, Saito M, Sugimoto T, Tomura Y, Wada K, Kusayama T, Tsukada J, Ishii N, Yatsu T, Uchida W et al.. (1998)
Pharmacological characterization of the human vasopressin receptor subtypes stably expressed in Chinese hamster ovary cells.
Br J Pharmacol, 125 (7): 1463-70. [PMID:9884074]
18. Thibonnier M, Auzan C, Madhun Z, Wilkins P, Berti-Mattera L, Clauser E. (1994)
Molecular cloning, sequencing, and functional expression of a cDNA encoding the human V1a vasopressin receptor.
J Biol Chem, 269 (5): 3304-10. [PMID:8106369]
19. Thibonnier M, Preston JA, Dulin N, Wilkins PL, Berti-Mattera LN, Mattera R. (1997)
The human V3 pituitary vasopressin receptor: ligand binding profile and density-dependent signaling pathways.
Endocrinology, 138 (10): 4109-22. [PMID:9322919]
20. Yamamura Y, Nakamura S, Itoh S, Hirano T, Onogawa T, Yamashita T, Yamada Y, Tsujimae K, Aoyama M, Kotosai K et al.. (1998)
OPC-41061, a highly potent human vasopressin V2-receptor antagonist: pharmacological profile and aquaretic effect by single and multiple oral dosing in rats.
J Pharmacol Exp Ther, 287 (3): 860-7. [PMID:9864265]