OPC-21268 | CAS#131631-89-5 | V1A receptor antagonist

MedKoo Cat#: 529801 | Name: OPC-21268

Description:

WARNING: This product is for research use only, not for human or veterinary use.

OPC-21268 is a vasopressin 1 (V1A) receptor antagonist potentially for the treatment of heart failure and hypertension.

Chemical Structure

OPC-21268

CAS#131631-89-5

Theoretical Analysis

MedKoo Cat#: 529801

Name: OPC-21268

CAS#: 131631-89-5

Chemical Formula: C26H31N3O4

Exact Mass: 449.2300

Molecular Weight: 449.55

Elemental Analysis: C, 69.47; H, 6.95; N, 9.35; O, 14.24

Price and Availability

Size	Price	Availability
10mg	USD 150.00	Ready to Ship
25mg	USD 250.00	Ready to ship
50mg	USD 450.00	Ready to ship
100mg	USD 750.00	Ready to ship
200mg	USD 1,250.00	Ready to ship
500mg	USD 2,650.00	Ready to ship
1g	USD 3,850.00	Ready to ship
2g	USD 6,250.00	Ready to ship

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Related CAS #

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Synonym

OPC-21268; OPC21268; OPC 21268; Fuscoside

IUPAC/Chemical Name

N-(3-(4-(4-(2-oxo-3,4-dihydroquinolin-1(2H)-yl)piperidine-1-carbonyl)phenoxy)propyl)acetamide

InChi Key

KSNUCNRMDYJBKT-UHFFFAOYSA-N

InChi Code

InChI=1S/C26H31N3O4/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)

SMILES Code

CC(NCCCOC1=CC=C(C(N2CCC(N3C(CCC4=C3C=CC=C4)=O)CC2)=O)C=C1)=O

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Product Data

Product Data

Certificate of Analysis

View CoA: current batch, Lot# C9R06B17

QC Data

View QC data: current batch, Lot# C9R06B17

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

Biological target:

Fuscoside (OPC-2128) is an orally effective, nonpeptide, vasopressin 1 receptor antagonist with an C50 of 0.4 μM.

In vitro activity:

This paper reports the in-vitro characterization of OPC-21268 binding to vasopressin receptors in rat liver and kidney. OPC-21268 caused a concentration-dependent displacement of the selective V1 receptor antagonist radioligand, 125I-labelled [d(CH2)5,sarcosine7]AVP to V1 receptors in both rat liver and kidney medulla membranes. The concentration of OPC-21268 that displaced 50% of specific AVP binding (IC50) was 40 +/- 3 nmol/l for liver V1 and 15 +/- 2 nmol/l for kidney V1 receptors (mean +/- S.E.M.; n = 3). OPC-21268 had little effect on the selective V2 antagonist radioligand [3H]desGly-NH2(9)]d(CH2)5,D-Ile2,Ile4] AVP binding to V2 receptors in renal medulla membranes (IC50 > 0.1 mmol/l). Binding kinetic studies showed that OPC-21268 acted as a competitive antagonist at the liver V1 receptor in vitro. Reference: J Endocrinol. 1993 Aug;138(2):259-66. https://pubmed.ncbi.nlm.nih.gov/8228734/

In vivo activity:

OPC-21268 caused a concentration-dependent displacement of the selective V1 receptor antagonist radioligand, 125I-labelled [d(CH2)5,sarcosine7]AVP to V1 receptors in both rat liver and kidney medulla membranes. The concentration of OPC-21268 that displaced 50% of specific AVP binding (IC50) was 40 +/- 3 nmol/l for liver V1 and 15 +/- 2 nmol/l for kidney V1 receptors (mean +/- S.E.M.; n = 3). OPC-21268 had little effect on the selective V2 antagonist radioligand [3H]desGly-NH2(9)]d(CH2)5,D-Ile2,Ile4] AVP binding to V2 receptors in renal medulla membranes (IC50 > 0.1 mmol/l). After oral administration to rats, OPC-21268 was an effective V1 antagonist in a time- and dose-dependent manner. Binding kinetic studies showed that OPC-21268 acted as a competitive antagonist at the liver V1 receptor in vitro and in vivo. OPC-21268 shows promise as an orally active V1 antagonist. J Endocrinol. 1993 Aug;138(2):259-66. https://pubmed.ncbi.nlm.nih.gov/8228734

	Solvent	mg/mL	mM
Solubility
	DMSO	20.0	44.50

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 449.55 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Jamil KM, Watanabe T, Nakao A, Okuda T, Kurokawa K. Distinct mechanisms of action of V1 antagonists OPC-21268 and [d(CH2)5Tyr(Me)AVP] in mesangial cells. Biochem Biophys Res Commun. 1993 Jun 15;193(2):738-43. doi: 10.1006/bbrc.1993.1687. PMID: 8390252. 2. Burrell LM, Phillips PA, Stephenson J, Risvanis J, Hutchins AM, Johnston CI. Characterization of a novel non-peptide vasopressin V1 receptor antagonist (OPC-21268) in the rat. J Endocrinol. 1993 Aug;138(2):259-66. doi: 10.1677/joe.0.1380259. PMID: 8228734. 3. Yamada Y, Yamamura Y, Chihara T, Onogawa T, Nakamura S, Yamashita T, Mori T, Tominaga M, Yabuuchi Y. OPC-21268, a vasopressin V1 antagonist, produces hypotension in spontaneously hypertensive rats. Hypertension. 1994 Feb;23(2):200-4. doi: 10.1161/01.hyp.23.2.200. PMID: 8307629.

In vitro protocol:

In vivo protocol:

1. Yamada Y, Yamamura Y, Chihara T, Onogawa T, Nakamura S, Yamashita T, Mori T, Tominaga M, Yabuuchi Y. OPC-21268, a vasopressin V1 antagonist, produces hypotension in spontaneously hypertensive rats. Hypertension. 1994 Feb;23(2):200-4. doi: 10.1161/01.hyp.23.2.200. PMID: 8307629.

1: Verzicco I, Tedeschi S, Graiani G, Bongrani A, Carnevali ML, Dancelli S, Zappa J, Mattei S, Bovino A, Cavazzini S, Rocco R, Calvi A, Palladini B, Volpi R, Cannone V, Coghi P, Borghetti A, Cabassi A. Evidence for a Prehypertensive Water Dysregulation Affecting the Development of Hypertension: Results of Very Early Treatment of Vasopressin V1 and V2 Antagonism in Spontaneously Hypertensive Rats. Front Cardiovasc Med. 2022 Jun 1;9:897244. doi: 10.3389/fcvm.2022.897244. PMID: 35722114; PMCID: PMC9198251. 2: Underwood CF, Burke PGR, Kumar NN, Goodchild AK, McMullan S, Phillips JK, Hildreth CM. Upregulated Angiotensin Ia Receptors in the Hypothalamic Paraventricular Nucleus Sensitize Neuroendocrine Vasopressin Release and Blood Pressure in a Rodent Model of Polycystic Kidney Disease. Neuroendocrinology. 2022;112(12):1200-1213. doi: 10.1159/000525337. Epub 2022 Jun 2. PMID: 35654013. 3: Huang JH, Chen YC, Lu YY, Lin YK, Chen SA, Chen YJ. Arginine vasopressin modulates electrical activity and calcium homeostasis in pulmonary vein cardiomyocytes. J Biomed Sci. 2019 Sep 17;26(1):71. doi: 10.1186/s12929-019-0564-3. PMID: 31530276; PMCID: PMC6747756. 4: Underwood CF, Boyd R, Phillips JK, Hildreth CM. Increased excitatory regulation of the hypothalamic paraventricular nucleus and circulating vasopressin results in the hypertension observed in polycystic kidney disease. J Hypertens. 2019 Jan;37(1):109-115. doi: 10.1097/HJH.0000000000001841. PMID: 30015755. 5: Ikeda T, Iwanaga Y, Watanabe H, Morooka H, Akahoshi Y, Fujiki H, Miyazaki S. Effects of Long-term Blockade of Vasopressin Receptor Types 1a and 2 on Cardiac and Renal Damage in a Rat Model of Hypertensive Heart Failure. J Cardiovasc Pharmacol. 2015 Nov;66(5):487-96. doi: 10.1097/FJC.0000000000000300. PMID: 26248278. 6: Masuki S, Sumiyoshi E, Koshimizu TA, Qian J, Higuchi K, Tsujimoto G, Nose H. Voluntary locomotion linked with cerebral activation is mediated by vasopressin V1a receptors in free-moving mice. J Physiol. 2013 Jul 15;591(14):3651-65. doi: 10.1113/jphysiol.2013.251876. Epub 2013 May 13. PMID: 23671158; PMCID: PMC3731620. 7: Bogolepova AE. [Opposite actions of different doses of arginine-vasotocin and 1-deamino-arginine-vasotocin on sodium ion transport in skin of the frog Rana temporaria]. Zh Evol Biokhim Fiziol. 2011 Jan-Feb;47(1):49-53. Russian. PMID: 21469341. 8: Karavashkina TA, Kutina AV, Shakhmatova EI, Natochin YV. Mechanism of 1-deamino-arginine vasotocin induced natriuresis in rats. Gen Comp Endocrinol. 2011 Feb 1;170(3):460-7. doi: 10.1016/j.ygcen.2010.10.020. Epub 2010 Nov 2. PMID: 21050856. 9: Takada M, Fujimaki-Aoba K, Hokari S. Effects of arginine vasotocin and mesotocin on the activation and development of amiloride-blockable short-circuit current across larval, adult, and cultured larval bullfrog skins. J Comp Physiol B. 2010 Mar;180(3):393-402. doi: 10.1007/s00360-009-0424-7. Epub 2009 Dec 1. PMID: 19949800. 10: Aoyagi T, Kusakawa S, Sanbe A, Hiroyama M, Fujiwara Y, Yamauchi J, Tanoue A. Enhanced effect of neuropeptide Y on food intake caused by blockade of the V(1A) vasopressin receptor. Eur J Pharmacol. 2009 Nov 10;622(1-3):32-6. doi: 10.1016/j.ejphar.2009.09.017. Epub 2009 Sep 17. PMID: 19766110. 11: Kato K, Kannan H, Ohta H, Kemuriyama T, Maruyama S, Tandai-Hiruma M, Sato Y, Nakazato M, Nishimori T, Ishida Y, Onaka T, Nishida Y. Central endogenous vasopressin induced by central salt-loading participates in body fluid homeostasis through modulatory effects on neurones of the paraventricular nucleus in conscious rats. J Neuroendocrinol. 2009 Nov;21(11):921-34. doi: 10.1111/j.1365-2826.2009.01915.x. Epub 2009 Sep 1. PMID: 19732288. 12: Maejima S, Yamada T, Hamada T, Matsuda K, Uchiyama M. Effects of hypertonic stimuli and arginine vasotocin (AVT) on water absorption response in Japanese treefrog, Hyla japonica. Gen Comp Endocrinol. 2008 Jun;157(2):196-202. doi: 10.1016/j.ygcen.2008.04.014. Epub 2008 May 3. PMID: 18555070. 13: Natochin IuV, Kanashkina TA, Shakhmatova EI, Bespalova ZhD, Mordvintsev DIu, Poliak IaL. [Effects of vasotocin analogs on excretion of Na+, K+, and Mg2+ ions via rat kidney]. Eksp Klin Farmakol. 2008 Mar-Apr;71(2):32-5. Russian. PMID: 18488904. 14: Yamada T, Nishio T, Sano Y, Kawago K, Matsuda K, Uchiyama M. Effects of arginine vasotocin and vasopressin receptor antagonists on Na+ and Cl- transport in the isolated skin of two frog species, Hyla japonica and Rana nigromaculata. Gen Comp Endocrinol. 2008 May 15;157(1):63-9. doi: 10.1016/j.ygcen.2008.03.022. Epub 2008 Mar 31. PMID: 18448104. 15: Kawano T, Tanaka K, Nazari H, Oshita S, Takahashi A, Nakaya Y. The effects of extracellular pH on vasopressin inhibition of ATP-sensitive K+ channels in vascular smooth muscle cells. Anesth Analg. 2007 Dec;105(6):1714-9, table of contents. doi: 10.1213/01.ane.0000290334.91624.2f. PMID: 18042872. 16: Natochin IuV, Kanashkina TA, Mordvintsev D, Shakhmatova EI. [Vasopressin receptors: structure and stimulation by 1-deamino-arginine-vasotocin in rats]. Ross Fiziol Zh Im I M Sechenova. 2007 Jun;93(6):625-34. Russian. PMID: 17850020. 17: O'Connor PM, Cowley AW Jr. Vasopressin-induced nitric oxide production in rat inner medullary collecting duct is dependent on V2 receptor activation of the phosphoinositide pathway. Am J Physiol Renal Physiol. 2007 Aug;293(2):F526-32. doi: 10.1152/ajprenal.00052.2007. Epub 2007 May 16. PMID: 17507604. 18: Birumachi J, Hiroyama M, Fujiwara Y, Aoyagi T, Sanbe A, Tanoue A. Impaired arginine-vasopressin-induced aldosterone release from adrenal gland cells in mice lacking the vasopressin V1A receptor. Eur J Pharmacol. 2007 Jul 2;566(1-3):226-30. doi: 10.1016/j.ejphar.2007.03.022. Epub 2007 Mar 24. PMID: 17449028. 19: Hagedorn TM, Carlin RW, Schultz BD. Oxytocin and vasopressin stimulate anion secretion by human and porcine vas deferens epithelia. Biol Reprod. 2007 Sep;77(3):416-24. doi: 10.1095/biolreprod.106.056762. Epub 2007 Apr 18. PMID: 17442854. 20: Hiroyama M, Wang S, Aoyagi T, Oikawa R, Sanbe A, Takeo S, Tanoue A. Vasopressin promotes cardiomyocyte hypertrophy via the vasopressin V1A receptor in neonatal mice. Eur J Pharmacol. 2007 Mar 22;559(2-3):89-97. doi: 10.1016/j.ejphar.2006.12.010. Epub 2006 Dec 29. PMID: 17275806.