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Details

Stereochemistry ABSOLUTE
Molecular Formula C43H67N15O12S2
Molecular Weight 1050.2193
Optical Activity UNSPECIFIED
Defined Stereocenters 9 / 9
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ARGIPRESTOCIN

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

Molecular Formula C43H67N15O12S2
Molecular Weight 1050.2193
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 9 / 9
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
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

Curator's Comment: Argiprestocin (arginine vasotocin) functions in CNS of primarily submammalian vertebrates. Argiprestocin is absent in mammals.

Originator

Curator's Comment: reference retrieved from https://uu.diva-portal.org/smash/get/diva2:171489/FULLTEXT01.pdf

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Potential candidate genomic biomarkers of drug induced vascular injury in the rat.
2011-12-01
Protective effects of echinocystic acid isolated from Gleditsia sinensis Lam. against acute myocardial ischemia.
2010-01
Case report: profound hypotension associated with labetalol therapy in a patient with cerebral aneurysms and subarachnoid hemorrhage.
2006-07
Comparative hemodynamic effects of vasopressin and norepinephrine after milrinone-induced hypotension in off-pump coronary artery bypass surgical patients.
2006-06
Central oxytocinergic and dopaminergic mechanisms regulating penile erection in conscious rats.
2005-08
Vasotocin and vasopressin stimulation of the chloride secretion in the human bronchial epithelial cell line, 16HBE14o-.
2005-04
Vasopressin-stimulated CFTR Cl- currents are increased in the renal collecting duct cells of a mouse model of Liddle's syndrome.
2005-01-01
Non-muscle myosin II and myosin light chain kinase are downstream targets for vasopressin signaling in the renal collecting duct.
2004-11-19
Vasoplegic syndrome after off-pump coronary artery bypass surgery: an unusual complication.
2004
Acute renal failure secondary to milrinone in a patient with cardiac amyloidosis.
2002-08
Vasopressin in the treatment of milrinone-induced hypotension in severe heart failure.
2000-02-15
Vasopressin as an alternative to norepinephrine in the treatment of milrinone-induced hypotension.
2000-01
Pulmonary vasodilatory response to neurohypophyseal peptides in the rat.
1992-08
Effect of hypotension and hyperosmolality on vasopressin and ACTH responses to hypoglycemia in conscious dogs.
1992-08
Evidence that apomorphine induces penile erection and yawning by releasing oxytocin in the central nervous system.
1989-05-30
Penile erection and yawning induced by oxytocin and related peptides: structure-activity relationship.
1989-05-01
[Effect of lysyl vasopressin and vasotocin on a disorder of the conditioned avoidance reaction by a serotonin receptor blockader].
1983-02
[Prevention of testosterone-vasopressin induced necrosis of the kidney cortex by cyproterone acetate].
1979-07
Cyproterone acetate-promoted prevention of renal cortical necrosis following testosterone and vasopressin administration.
1979-02
An approach to the control of massive hemorrhage in cyclophosphamide-induced cystitis by intravenous vasopressin: a case report.
1978-08
Effect of vasopressin administration on renal haemodynamic changes in rats treated with ACTH.
1973-10-22
Responses of the rat foetus to maternal injections of adrenaline and vasopressin.
1971-10
Ventricular extrasystoles induced by epinephrine, nicotine, ethanol, and vasopressin in dogs with myocardial lesions.
1969-07

Sample Use Guides

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 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.
Substance Class Chemical
Created
by admin
on Mon Mar 31 18:19:42 GMT 2025
Edited
by admin
on Mon Mar 31 18:19:42 GMT 2025
Record UNII
W6S6URY8OF
Record Status FAILED
Record Version
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Name Type Language
ARGIPRESTOCIN
INN  
INN  
Official Name English
ARGININE VASOTOCIN [MI]
Preferred Name English
8-ARGININEOXYTOCIN
Common Name English
argiprestocin [INN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C548
Created by admin on Mon Mar 31 18:19:42 GMT 2025 , Edited by admin on Mon Mar 31 18:19:42 GMT 2025
Code System Code Type Description
MERCK INDEX
m11399
Created by admin on Mon Mar 31 18:19:42 GMT 2025 , Edited by admin on Mon Mar 31 18:19:42 GMT 2025
PRIMARY Merck Index
PUBCHEM
10034060
Created by admin on Mon Mar 31 18:19:42 GMT 2025 , Edited by admin on Mon Mar 31 18:19:42 GMT 2025
PRIMARY
SMS_ID
100000086599
Created by admin on Mon Mar 31 18:19:42 GMT 2025 , Edited by admin on Mon Mar 31 18:19:42 GMT 2025
PRIMARY
INN
1483
Created by admin on Mon Mar 31 18:19:42 GMT 2025 , Edited by admin on Mon Mar 31 18:19:42 GMT 2025
PRIMARY
FDA UNII
W6S6URY8OF
Created by admin on Mon Mar 31 18:19:42 GMT 2025 , Edited by admin on Mon Mar 31 18:19:42 GMT 2025
PRIMARY
WIKIPEDIA
Vasotocin
Created by admin on Mon Mar 31 18:19:42 GMT 2025 , Edited by admin on Mon Mar 31 18:19:42 GMT 2025
PRIMARY
CHEBI
78364
Created by admin on Mon Mar 31 18:19:42 GMT 2025 , Edited by admin on Mon Mar 31 18:19:42 GMT 2025
PRIMARY
NCI_THESAURUS
C87380
Created by admin on Mon Mar 31 18:19:42 GMT 2025 , Edited by admin on Mon Mar 31 18:19:42 GMT 2025
PRIMARY
ChEMBL
CHEMBL2370156
Created by admin on Mon Mar 31 18:19:42 GMT 2025 , Edited by admin on Mon Mar 31 18:19:42 GMT 2025
PRIMARY
EVMPD
SUB05562MIG
Created by admin on Mon Mar 31 18:19:42 GMT 2025 , Edited by admin on Mon Mar 31 18:19:42 GMT 2025
PRIMARY
CAS
113-80-4
Created by admin on Mon Mar 31 18:19:42 GMT 2025 , Edited by admin on Mon Mar 31 18:19:42 GMT 2025
PRIMARY
EPA CompTox
DTXSID40873492
Created by admin on Mon Mar 31 18:19:42 GMT 2025 , Edited by admin on Mon Mar 31 18:19:42 GMT 2025
PRIMARY
Related Record Type Details
ACTIVE MOIETY