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

MedKoo CAT#: 326667

CAS#: 81840-15-5

Description: Vesnarinone is a cardiotonic agent, mixed phosphodiesterase 3 inhibitor and ion-channel modifier that has modest, dose-dependent, positive inotropic activity, but minimal negative chronotropic activity. Vesnarinone improves ventricular performance most in patients with the worst degree of heart failure.


Price and Availability

Size
Price

10mg
USD 150
100mg
USD 750
1g
USD 2950
Size
Price

25mg
USD 250
200mg
USD 1250
2g
USD 4250
Size
Price

50mg
USD 450
500mg
USD 2250
5g
USD 7950

Vesnarinone, purity > 98%, is in stock. The same day shipping out after order is received. Delivery time: overnight (USA/Canada); 3-5 days (worldwide).


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 326667
Name: Vesnarinone
CAS#: 81840-15-5
Chemical Formula: C22H25N3O4
Exact Mass: 395.1845
Molecular Weight: 395.459
Elemental Analysis: C, 66.82; H, 6.37; N, 10.63; O, 16.18


Synonym: RG-0210; RG 0210; RG0210; OPC-8212; OPC 8212; OPC8212; Piteranometozine; Vesnarinone; Arkin; Arkin-Z.

IUPAC/Chemical Name: 6-[4-(3,4-dimethoxybenzoyl)piperazin-1-yl]-3,4-dihydro-1H-quinolin-2-one

InChi Key: ZVNYJIZDIRKMBF-UHFFFAOYSA-N

InChi Code: InChI=1S/C22H25N3O4/c1-28-19-7-3-16(14-20(19)29-2)22(27)25-11-9-24(10-12-25)17-5-6-18-15(13-17)4-8-21(26)23-18/h3,5-7,13-14H,4,8-12H2,1-2H3,(H,23,26)

SMILES Code: O=C1NC2=C(C=C(N3CCN(C(C4=CC=C(OC)C(OC)=C4)=O)CC3)C=C2)CC1


Technical Data

Appearance:
White to off-white solid powder

Purity:
>97% (or refer to the Certificate of Analysis)

Certificate of Analysis:

Safety Data Sheet (MSDS):

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, not in water

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).

Harmonized System Code:
293490


References

1: Hotta K, Nashimoto A, Yasumura E, Suzuki M, Azuma M, Iizumi Y, Shima D, Nabeshima R, Hiramoto M, Okada A, Sakata-Sogawa K, Tokunaga M, Ito T, Ando H, Sakamoto S, Kabe Y, Aizawa S, Imai T, Yamaguchi Y, Watanabe H, Handa H. Vesnarinone suppresses TNFα mRNA expression by inhibiting valosin-containing protein. Mol Pharmacol. 2013 May;83(5):930-8. doi: 10.1124/mol.112.081935. Epub 2013 Feb 7. PubMed PMID: 23393163.

2: Uchida D, Onoue T, Begum NM, Kuribayashi N, Tomizuka Y, Tamatani T, Nagai H, Miyamoto Y. Vesnarinone downregulates CXCR4 expression via upregulation of Krüppel-like factor 2 in oral cancer cells. Mol Cancer. 2009 Aug 12;8:62. doi: 10.1186/1476-4598-8-62. PubMed PMID: 19671192; PubMed Central PMCID: PMC2738650.

3: Inage M, Nakamura H, Saito H, Abe S, Hino T, Takabatake N, Terashita K, Ogura M, Kato S, Hosokawa T, Sata M, Tomoike H. Vesnarinone represses the fibrotic changes in murine lung injury induced by bleomycin. Int J Biol Sci. 2009;5(4):304-10. Epub 2009 Apr 16. PubMed PMID: 19381349; PubMed Central PMCID: PMC2669598.

4: Harada K, Supriatno, Yoshida H, Sato M. Vesnarinone inhibits angiogenesis and tumorigenicity of human oral squamous cell carcinoma cells by suppressing the expression of vascular endothelial growth factor and interleukin-8. Int J Oncol. 2005 Dec;27(6):1489-97. PubMed PMID: 16273203.

5: Gardner I, Popović M, Zahid N, Uetrecht JP. A comparison of the covalent binding of clozapine, procainamide, and vesnarinone to human neutrophils in vitro and rat tissues in vitro and in vivo. Chem Res Toxicol. 2005 Sep;18(9):1384-94. PubMed PMID: 16167830.

6: Truter SL, Dumlao TF, Lee JA, Lee E, Supino PG, Borer JS. Vesnarinone-mediated alterations of gene expression in cardiac fibroblasts from aortic regurgitant hearts. Am J Ther. 2004 Sep-Oct;11(5):328-36. PubMed PMID: 15356428.

7: Bertolet BD. Precautions for use and adverse effects of vesnarinone: potential mechanisms and future therapies. Drug Saf. 2004;27 Suppl 1:11-8. Review. PubMed PMID: 15293849.

8: Feldman AM. Clinical characteristics of vesnarinone. Drug Saf. 2004;27 Suppl 1:1-9. Review. PubMed PMID: 15293848.

9: Young JB. The best of times, the worst of times: the wealth and poverty of heart failure pharmacotherapies: is there a role for vesnarinone? Drug Saf. 2004;27 Suppl 1:3 p following table of contents. PubMed PMID: 15293847.

10: Sekar KS, Bramer SL. Extended application of an LC-MS/MS method for the analysis of vesnarinone and its metabolites in human urine and dialysate fluid. J Pharm Biomed Anal. 2003 Nov 24;33(4):711-7. PubMed PMID: 14623597.

11: Kawamata H, Omotehara F, Nakashiro K, Uchida D, Hino S, Fujimori T. Vesnarinone: a differentiation-inducing anti-cancer drug. Anticancer Drugs. 2003 Jul;14(6):391-5. Review. PubMed PMID: 12853878.

12: Omotehara F, Nakashiro K, Uchida D, Hino S, Fujimori T, Kawamata H. Transcriptional activation of cyclin-dependent kinase inhibitor, p21waf1 gene by treatment with a differentiation inducing agent, vesnarinone in a human salivary gland cancer cell line. J Exp Clin Cancer Res. 2003 Mar;22(1):57-60. PubMed PMID: 12725323.

13: Omotehara F, Kawamata H, Uchida D, Hino S, Nakashiro K, Fujimori T. Vesnarinone, a differentiation inducing drug, directly activates p21(waf1) gene promoter via Sp1 sites in a human salivary gland cancer cell line. Br J Cancer. 2002 Oct 21;87(9):1042-6. PubMed PMID: 12434298; PubMed Central PMCID: PMC2364327.

14: Isaka K, Fujito A, Sagawa Y, Yudate T, Nishi H, Ito H, Takayama M. Induction of apoptosis in human choriocarcinoma cell lines by treatment with 3,4-dihydro-6-[4-(3,4-dimethoxybenzoyl)-1-piperazinyl]-2(1H)-quinolinone (vesnarinone). Oncol Rep. 2002 Nov-Dec;9(6):1299-305. PubMed PMID: 12375038.

15: Kondo T, Suzuki Y, Kitano T, Iwai K, Watanabe M, Umehara H, Daido N, Domae N, Tashima M, Uchiyama T, Okazaki T. Vesnarinone causes oxidative damage by inhibiting catalase function through ceramide action in myeloid cell apoptosis. Mol Pharmacol. 2002 Mar;61(3):620-7. PubMed PMID: 11854443.

16: Khalaf W, Maina C, Byers J, Harvey W. Interferon-alpha 2b and vesnarinone influence levels of tumor necrosis factor-alpha, apoptosis, or interleukin 6 in ESKOL, a hairy cell leukemic cell line. A potential cytokine and oncogene relationship regulating apoptosis is suggested. Leuk Res. 2002 Feb;26(2):169-77. PubMed PMID: 11755467.

17: Cheng JH, Kamiya K, Kodama I. Carvedilol and vesnarinone: new antiarrhythmic approach in heart failure therapy. Acta Pharmacol Sin. 2001 Mar;22(3):193-200. Review. PubMed PMID: 11742564.

18: Deswal A, Petersen NJ, Feldman AM, White BG, Mann DL. Effects of vesnarinone on peripheral circulating levels of cytokines and cytokine receptors in patients with heart failure: a report from the Vesnarinone Trial. Chest. 2001 Aug;120(2):453-9. PubMed PMID: 11502643.

19: Kamiya K, Mitcheson JS, Yasui K, Kodama I, Sanguinetti MC. Open channel block of HERG K(+) channels by vesnarinone. Mol Pharmacol. 2001 Aug;60(2):244-53. PubMed PMID: 11455010.

20: Deswal A, Petersen NJ, Feldman AM, Young JB, White BG, Mann DL. Cytokines and cytokine receptors in advanced heart failure: an analysis of the cytokine database from the Vesnarinone trial (VEST). Circulation. 2001 Apr 24;103(16):2055-9. PubMed PMID: 11319194.