vasopressin   Click here for help

GtoPdb Ligand ID: 2168

Abbreviated name: AVP
Synonyms: ADH | antidiuretic hormone | arginine vasopressin | argipressin
Approved drug
vasopressin is an approved drug (FDA (date of approval not specified))
Comment: The approved drug is administered as an injection, as indicated by the INN.

As with all large peptide molecules, there is some ambiguity in representations of the stereochemistry of vasopressin, therefore the chemical structure shown here may differ slightly from that shown on other resouces linked to from the table above.
Species: Human, Mouse, Rat
Click here for help
IUPHAR Pharmacology Education Project (PEP) logo

View more information in the IUPHAR Pharmacology Education Project: vasopressin

2D Structure
Click here for help
Click here for structure editor
Click here for help
Canonical SMILES NC(=O)CC1NC(=O)C(CCC(=O)N)NC(=O)C(Cc2ccccc2)NC(=O)C(Cc2ccc(cc2)O)NC(=O)C(CSSCC(NC1=O)C(=O)N1CCCC1C(=O)NC(C(=O)NCC(=O)N)CCCN=C(N)N)N
Isomeric SMILES NC(=O)C[C@@H]1NC(=O)[C@H](CCC(=O)N)NC(=O)[C@H](Cc2ccccc2)NC(=O)[C@H](Cc2ccc(cc2)O)NC(=O)[C@H](CSSC[C@H](NC1=O)C(=O)N1CCC[C@H]1C(=O)N[C@H](C(=O)NCC(=O)N)CCCN=C(N)N)N
InChI InChI=1S/C46H65N15O12S2/c47-27-22-74-75-23-33(45(73)61-17-5-9-34(61)44(72)56-28(8-4-16-53-46(51)52)39(67)54-21-37(50)65)60-43(71)32(20-36(49)64)59-40(68)29(14-15-35(48)63)55-41(69)31(18-24-6-2-1-3-7-24)58-42(70)30(57-38(27)66)19-25-10-12-26(62)13-11-25/h1-3,6-7,10-13,27-34,62H,4-5,8-9,14-23,47H2,(H2,48,63)(H2,49,64)(H2,50,65)(H,54,67)(H,55,69)(H,56,72)(H,57,66)(H,58,70)(H,59,68)(H,60,71)(H4,51,52,53)/t27-,28-,29-,30-,31-,32-,33-,34-/m0/s1
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. Breton C, Chellil H, Kabbaj-Benmansour M, Carnazzi E, Seyer R, Phalipou S, Morin D, Durroux T, Zingg H, Barberis C et al.. (2001)
Direct identification of human oxytocin receptor-binding domains using a photoactivatable cyclic peptide antagonist: comparison with the human V1a vasopressin receptor.
J Biol Chem, 276 (29): 26931-41. [PMID:11337500]
3. 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]
4. 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]
5. 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]
6. 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]
7. 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]
8. 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]
9. 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]
10. 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]
11. 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]
12. 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]
13. 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]
14. 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]
15. 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]
16. 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]
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 YM087, a potent, nonpeptide human vasopressin V1A and V2 receptor antagonist.
Naunyn Schmiedebergs Arch Pharmacol, 357 (1): 63-9. [PMID:9459574]
18. 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]
19. 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]
20. 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]
21. 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]