OPC-21268
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MedKoo CAT#: 529801

CAS#: 131631-89-5

Description: OPC-21268 is a vasopressin 1 receptor antagonist potentially for the treatment of heart failure and hypertension.


Chemical Structure

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OPC-21268
CAS# 131631-89-5

Theoretical Analysis

MedKoo Cat#: 529801
Name: OPC-21268
CAS#: 131631-89-5
Chemical Formula: C26H31N3O4
Exact Mass: 449.23
Molecular Weight: 449.550
Elemental Analysis: C, 69.47; H, 6.95; N, 9.35; O, 14.24

Price and Availability

Size Price Availability Quantity
10mg USD 150 Ready to Ship
25mg USD 250 Ready to ship
50mg USD 450 Ready to ship
100mg USD 750 Ready to ship
200mg USD 1250 Ready to ship
500mg USD 2650 Ready to ship
1g USD 3850 Ready to ship
2g USD 6250 Ready to ship
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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:

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

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 20.0 44.50

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.

Recalculate based on batch purity %
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: 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.
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.

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1: Shinoura H, Take H, Itoh S, Hirasawa A, Inoue K, Ohno Y, Hashimoto K, Tsujimoto G. Key amino acids of vasopressin V1a receptor responsible for the species difference in the affinity of OPC-21268. FEBS Lett. 2000 Jan 28;466(2-3):255-8. Erratum in: FEBS Lett 2000 Jun 2;474(2-3):257. PubMed PMID: 10682838.

2: Sugimoto I, Narimiya N, Odagiri M, Ohnishi A, Tanaka T. Protective effect of a vasopressin-1 selective antagonist, OPC-21268, against ethanol-induced damage of the rat gastric wall. Dig Dis Sci. 1999 Mar;44(3):503-9. PubMed PMID: 10080141.

3: Bemana I, Nagao S. Treatment of brain edema with a nonpeptide arginine vasopressin V1 receptor antagonist OPC-21268 in rats. Neurosurgery. 1999 Jan;44(1):148-54; discussion 154-5. PubMed PMID: 9894975.

4: Kawano Y, Matsuoka H, Nishikimi T, Takishita S, Omae T. The role of vasopressin in essential hypertension. Plasma levels and effects of the V1 receptor antagonist OPC-21268 during different dietary sodium intakes. Am J Hypertens. 1997 Nov;10(11):1240-4. PubMed PMID: 9397242.

5: Otsuka F, Ogura T, Yamauchi T, Oishi T, Hashimoto M, Mimura Y, Makino H. Effects of OPC-21268, a vasopressin V1-receptor antagonist, on expression of growth factors from glomeruli in spontaneously hypertensive rats. Regul Pept. 1997 Oct 31;72(2-3):87-95. PubMed PMID: 9652981.

6: Bemana I, Takahashi E, Nakamura T, Kuyama H, Nagao S. OPC-21268, an orally effective, nonpeptide arginine vasopressin V1 receptor antagonist reduces vasogenic brain edema. Acta Neurochir Suppl. 1997;70:194-7. PubMed PMID: 9416320.

7: Mimura Y, Ogura T, Hayakawa N, Otsuka F, Hashimoto M, Yamauchi T, Makino H, Ogawa N. In vitro macro- and microautoradiographic localization of V1 and V2 receptors in the rat kidney using OPC-21268 and OPC-31260. Nephron. 1997;76(3):331-6. PubMed PMID: 9226235.

8: Kurihara I, Saito T, Obara K, Shoji Y, Hirai M, Soma J, Sato H, Imai Y, Abe K. Effect of a nonpeptide vasopressin V1 antagonist (OPC-21268) on experimental accelerated focal glomerulosclerosis. Nephron. 1996;73(4):629-36. PubMed PMID: 8856262.

9: 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. PubMed PMID: 19732288.

10: Chihara T, Nakamura S, Onogawa T, Yamashita T, Yamamura Y, Mori T, Tominaga M, Yabuuchi Y. OPC-21268 antagonizes arginine vasopressin-induced vasoconstrictor response in the spinally-anesthetized dog. Jpn J Pharmacol. 1995 Jul;68(3):345-7. PubMed PMID: 7474558.

11: Atke A, Vilhardt H, Hauzerova L, Barth T, Andersen LF. Effects of the non-peptide inhibitor OPC-21268 on oxytocin and vasopressin stimulation of rat and human myometrium. Eur J Pharmacol. 1995 Jul 25;281(1):63-8. PubMed PMID: 8566118.

12: Naitoh M, Suzuki H, Murakami M, Matsumoto A, Arakawa K, Ichihara A, Nakamoto H, Oka K, Yamamura Y, Saruta T. Effects of oral AVP receptor antagonists OPC-21268 and OPC-31260 on congestive heart failure in conscious dogs. Am J Physiol. 1994 Dec;267(6 Pt 2):H2245-54. PubMed PMID: 7810724.

13: Shinouraa2 H, Takea2 H, Itohb S, Hirasawaa A, Inouec K, Ohnoc Y, Hashimotod K, Tsujimotoa G. Corrigendum to: key amino acids of vasopressin V1a receptor responsible for the species difference in the affinity of OPC-21268 (FEBS 23227). FEBS Lett. 2000 Jun 2;474(2-3):257. PubMed PMID: 10838096.

14: 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. PubMed PMID: 18555070.

15: 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. PubMed PMID: 8307629.

16: Li X, Kribben A, Wieder ED, Tsai P, Nemenoff RA, Schrier RW. Inhibition of vasopressin action in vascular smooth muscle by the V1 antagonist OPC-21268. Hypertension. 1994 Feb;23(2):217-22. PubMed PMID: 8307632.

17: 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. PubMed PMID: 8228734.

18: 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. PubMed PMID: 8390252.

19: Masaki H, Imaizumi T, Harada S, Momohara M, Hirooka Y, Takeshita A. Effects of a novel orally effective V1-receptor antagonist, OPC-21268, on AVP-induced sympathoinhibition. Am J Physiol. 1993 Jun;264(6 Pt 2):R1089-94. PubMed PMID: 8391757.

20: Nakamura T, Sakamaki T, Kurashina T, Hoshino J, Sato K, Ono Z, Murata K. Effect of vasopressin V (OPC-21268) and V2 (OPC-31260) antagonists on renal hemodynamics and excretory function. Life Sci. 1994;55(4):PL67-72. PubMed PMID: 8028441.