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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
Pricing and availability is not currently available.

Quality Level

100

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 a vasopressin V1a selective antagonist.
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

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Certificates of Analysis (COA)

Lot/Batch Number
090M4638V
090M4638

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[Renal action of vasopressin].
Masami Sasaki et al.
Nihon rinsho. Japanese journal of clinical medicine, 64 Suppl 2, 257-264 (2006-03-10)
A E Bogolepova
Zhurnal evoliutsionnoi biokhimii i fiziologii, 47(1), 49-53 (2011-04-08)
Active transport of sodium ions across the isolated abdominal skin of the frog Rana temporaria after application of arginine-vasotocin (AVT) and 1-deamino-arginine-vasotocin (1dAVT) was studied by measurement of the short-circuit current (SCC). The maximal increase in the SCC values (26
A B Roald et al.
Acta physiologica Scandinavica, 182(2), 197-204 (2004-09-29)
Arginine vasopressin (AVP) might influence urinary concentration ability by altering the intrarenal distribution of glomerular filtration rate (GFR). To study this possibility we have measured the intracortical distribution of GFR following acute AVP-V1 receptor stimulation in anaesthetized female Sprague-Dawley (SPD)
C Serradeil-Le Gal et al.
Progress in brain research, 139, 197-210 (2002-11-20)
The involvement of vasopressin (AVP) in several pathological states has been reported recently and the selective blockade of the different AVP receptors could offer new clinical perspectives. During the past few years, various selective, orally active AVP V1a (OPC-21268, SR49059
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
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