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O1016

Sigma-Aldrich

OPC-21268 hydrate

≥98% (HPLC)

Synonym(s):

1-{1-[4(3-acetylaminopropoxy)benzoyl]-4-piperidyl}-3,4-dihydro-2(1H)-quinolinone hydrate, N-[3-[4-[[4-(3,4-dihydro-2-oxo-1(2H)-quinolinyl)-1-piperidinyl]carbonyl]phenoxy]propyl]-acetamide hydrate

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About This Item

Empirical Formula (Hill Notation):
C26H31N3O4 · xH2O
CAS Number:
131631-89-5
Molecular Weight:
449.54 (anhydrous basis)
MDL number:
MFCD18632552
UNSPSC Code:
51111800
PubChem Substance ID:
329818893
NACRES:
NA.77

Assay

≥98% (HPLC)

form

powder

color

white to off-white

solubility

DMSO: ≥20 mg/mL

originator

Merck & Co., Inc., Kenilworth, NJ, U.S.

storage temp.

2-8°C

SMILES string

O.CC(=O)NCCCOc1ccc(cc1)C(=O)N2CCC(CC2)N3C(=O)CCc4ccccc34

InChI

1S/C26H31N3O4.H2O/c1-19(30)27-15-4-18-33-23-10-7-21(8-11-23)26(32)28-16-13-22(14-17-28)29-24-6-3-2-5-20(24)9-12-25(29)31;/h2-3,5-8,10-11,22H,4,9,12-18H2,1H3,(H,27,30);1H2

InChI key

QTCWOUIERWBMQV-UHFFFAOYSA-N

Biochem/physiol Actions

OPC-21268 is one of 2 non-peptide V1a selective antagonists, along with SR-49059. Arginine vasopressin (AVP) is a hormone that plays an important part in circulatory and water homoeostasis and is important in renal hemodynamic alterations, water retention, and cardiac remodeling in congestive heart failure (CHF). There are three AVP receptor subtypes-V1a, V1b, and V2 - all belong to the large rhodopsin-like G-protein-coupled receptor family. V(1a) antagonists improve water balance and cardiac hypertrophy in CHF and might be beneficial for the treatment of water retention and cardiac remodeling in CHF.

Features and Benefits

This compound was developed by Merck & Co., Inc., Kenilworth, NJ, U.S.. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Pictograms

Exclamation markEnvironment
GHS07,GHS09

Signal Word

Warning

Hazard Statements

H302,H400

Precautionary Statements

P273 - P301 + P312 + P330

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Acute 1

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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James Walter Ferguson et al.
Clinical science (London, England : 1979), 105(1), 1-8 (2003-03-18)
Vasopressin, or antidiuretic hormone, is a peptide hormone that is released from the posterior pituitary gland in response to changes in blood pressure and plasma osmolality. The main pathophysiological states associated with high plasma vasopressin concentrations are cirrhosis, cardiac failure
Chun-Ping Chu et al.
Neuroscience research, 53(2), 147-155 (2005-07-26)
The present study is an investigation of the responses of the cardiovascular system and Fos expression to intracerebroventricular (i.c.v.) administration of hypertonic saline (HS) in conscious arginine vasopressin (AVP)-overexpressing transgenic (Tg) and control rats. Central HS (0.3, 0.67, or 1.0M
Sho Maejima et al.
General and comparative endocrinology, 157(2), 196-202 (2008-06-17)
Anuran amphibians do not drink orally but absorb water osmotically through the highly permeable ventral skin. In this cutaneous water absorption, roles of the putative cerebral osmoreceptors and functions of arginine vasotocin (AVT) were examined in the central nervous system
Nina Japundzić-Zigon et al.
Journal of pharmacological sciences, 95(1), 47-55 (2004-05-22)
Effects of V(1) (OPC-21268) and V(2) (OPC-31260) vasopressin antagonists on blood pressure (BP) short-term variability were investigated in adult spontaneously hypertensive rats (SHR) under basal conditions and after the stimulation of vasopressin release by hemorrhage. BP was recorded intra-arterially and
Iu V Natochin et al.
Rossiiskii fiziologicheskii zhurnal imeni I.M. Sechenova, 93(6), 625-634 (2007-09-14)
In experiments on non-anesthetized female Wistar rats, it has been shown that injection of 1-deamino-arginine-vasotocin (1dAVT) increases sodium excretion and solute-free water reabsorption. Antagonists of V1-receptors (OPC-31260, Otsuka Pharmaceutical Co., Ltd., Japan) eliminates the effect water reabsorption whereas antagonist of
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