ARGIPRESTOCIN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C43H67N15O12S2
Molecular Weight	1050.215
Optical Activity	UNSPECIFIED
Defined Stereocenters	9 / 9
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@]1(NC(=O)[C@H](CC2=CC=C(O)C=C2)NC(=O)[C@@H](N)CSSC[C@H](NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CCC(N)=O)NC1=O)C(=O)N3CCC[C@H]3C(=O)N[C@@H](CCCNC(N)=N)C(=O)NCC(N)=O)[C@@H](C)CC

InChI

InChIKey=OXDZADMCOWPSOC-BQGUCLBMSA-N

InChI=1S/C43H67N15O12S2/c1-3-21(2)34-41(69)53-26(12-13-31(45)60)37(65)55-28(17-32(46)61)38(66)56-29(20-72-71-19-24(44)35(63)54-27(39(67)57-34)16-22-8-10-23(59)11-9-22)42(70)58-15-5-7-30(58)40(68)52-25(6-4-14-50-43(48)49)36(64)51-18-33(47)62/h8-11,21,24-30,34,59H,3-7,12-20,44H2,1-2H3,(H2,45,60)(H2,46,61)(H2,47,62)(H,51,64)(H,52,68)(H,53,69)(H,54,63)(H,55,65)(H,56,66)(H,57,67)(H4,48,49,50)/t21-,24-,25-,26-,27-,28-,29-,30-,34-/m0/s1

HIDE SMILES / InChI

Description
Sources: https://uu.diva-portal.org/smash/get/diva2:171489/FULLTEXT01.pdf
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/16480986 | https://www.ncbi.nlm.nih.gov/pubmed/16288753 | https://www.ncbi.nlm.nih.gov/pubmed/23809437 | https://www.ncbi.nlm.nih.gov/pubmed/25102443

Arginine vasotocin (Argiprestocin, AVT) is the non-mammalian homologue of arginine vasopressin (AVP) and was first synthesized as an AVP analogue. It was later found in non-mammalian vertebrates and induces similar physiological effects as AVP. AVT is considered the primary antidiuretic hormone. AVT functions to regulate expression of social and reproductive behaviors.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
arginine vasopressin receptor 1B 1 Target ID: 428263.0 Gene Symbol: AVPR1B Sources: https://www.ncbi.nlm.nih.gov/pubmed/8162166 \| https://www.ncbi.nlm.nih.gov/pubmed/19215402 \| https://www.ncbi.nlm.nih.gov/pubmed/9835346	Agonist 2678		0.48 nM [Kd]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2578

PubMed

Title	Date	PubMed
Ventricular extrasystoles induced by epinephrine, nicotine, ethanol, and vasopressin in dogs with myocardial lesions.	1969 Jul	4185489
Responses of the rat foetus to maternal injections of adrenaline and vasopressin.	1971 Oct	4945727
Effect of vasopressin administration on renal haemodynamic changes in rats treated with ACTH.	1973 Oct 22	4358912
An approach to the control of massive hemorrhage in cyclophosphamide-induced cystitis by intravenous vasopressin: a case report.	1978 Aug	671649
Cyproterone acetate-promoted prevention of renal cortical necrosis following testosterone and vasopressin administration.	1979 Feb	465307
[Prevention of testosterone-vasopressin induced necrosis of the kidney cortex by cyproterone acetate].	1979 Jul	503094
[Effect of lysyl vasopressin and vasotocin on a disorder of the conditioned avoidance reaction by a serotonin receptor blockader].	1983 Feb	6824771
Evidence that apomorphine induces penile erection and yawning by releasing oxytocin in the central nervous system.	1989 May 30	2767126
Penile erection and yawning induced by oxytocin and related peptides: structure-activity relationship.	1989 May-Jun	2780415
Pulmonary vasodilatory response to neurohypophyseal peptides in the rat.	1992 Aug	1399968
Effect of hypotension and hyperosmolality on vasopressin and ACTH responses to hypoglycemia in conscious dogs.	1992 Aug	1324617
Vasopressin in the treatment of milrinone-induced hypotension in severe heart failure.	2000 Feb 15	10728962
Vasopressin as an alternative to norepinephrine in the treatment of milrinone-induced hypotension.	2000 Jan	10667533
Acute renal failure secondary to milrinone in a patient with cardiac amyloidosis.	2002 Aug	12148128
Vasoplegic syndrome after off-pump coronary artery bypass surgery: an unusual complication.	2004	15745296
Non-muscle myosin II and myosin light chain kinase are downstream targets for vasopressin signaling in the renal collecting duct.	2004 Nov 19	15347643
Vasotocin and vasopressin stimulation of the chloride secretion in the human bronchial epithelial cell line, 16HBE14o-.	2005 Apr	15685210
Central oxytocinergic and dopaminergic mechanisms regulating penile erection in conscious rats.	2005 Aug	16005055
Vasopressin-stimulated CFTR Cl- currents are increased in the renal collecting duct cells of a mouse model of Liddle's syndrome.	2005 Jan 1	15513933
Case report: profound hypotension associated with labetalol therapy in a patient with cerebral aneurysms and subarachnoid hemorrhage.	2006 Jul	16803915
Comparative hemodynamic effects of vasopressin and norepinephrine after milrinone-induced hypotension in off-pump coronary artery bypass surgical patients.	2006 Jun	16675238
Protective effects of echinocystic acid isolated from Gleditsia sinensis Lam. against acute myocardial ischemia.	2010 Jan	19573579
Potential candidate genomic biomarkers of drug induced vascular injury in the rat.	2011 Dec 1	21983523

Sample Use Guides

In Vivo Use Guide

fish: 10 ug/g caused a progressive increase of electric organ discharges rate. green anole lizard: 15 ug regulates reptile social behavior

Route of Administration: Intraperitoneal

In Vitro Use Guide

In vitro stimulation of the aquatic Xenopus urinary bladder with 10 nM Argiprestocin (arginine vasotocin) had no clear effect on the subcellular distribution of urinary bladder-type aquaporin, AQP-x2. When the Argiprestocin concentration was increased to 1 uM, however, AQP-x2 was partially transferred to the apical plasma membrane.

Name

Type

Language

ARGIPRESTOCIN

Official Name

English

8-ARGININEOXYTOCIN

Common Name

English

argiprestocin [INN]

Common Name

English

ARGININE VASOTOCIN [MI]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C548