KMUP 1 | CAS#81996-46-5 | potassium channel opener

MedKoo Cat#: 584514 | Name: KMUP 1

Description:

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

KMUP 1 is a potassium channel opener and stimulator of the NO/sGC/cGMP pathway.

Chemical Structure

KMUP 1

CAS#81996-46-5

Theoretical Analysis

MedKoo Cat#: 584514

Name: KMUP 1

CAS#: 81996-46-5

Chemical Formula: C19H23ClN6O2

Exact Mass: 402.1571

Molecular Weight: 402.88

Elemental Analysis: C, 56.64; H, 5.75; Cl, 8.80; N, 20.86; O, 7.94

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.

Bulk Inquiry

Related CAS #

No Data

Synonym

KMUP 1; KMUP-1; KMUP1

IUPAC/Chemical Name

1H-Purine-2,6-dione, 7-(2-(4-(2-chlorophenyl)-1-piperazinyl)ethyl)-3,7-dihydro-1,3-dimethyl-

InChi Key

NIDVDYQCGWISJZ-UHFFFAOYSA-N

InChi Code

InChI=1S/C19H23ClN6O2/c1-22-17-16(18(27)23(2)19(22)28)26(13-21-17)12-9-24-7-10-25(11-8-24)15-6-4-3-5-14(15)20/h3-6,13H,7-12H2,1-2H3

SMILES Code

O=C(N1C)N(C)C2=C(N(CCN3CCN(C4=CC=CC=C4Cl)CC3)C=N2)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

>3 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

2934.99.03.00

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 402.88 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

1: Liou SF, Hsu JH, Chen YT, Chen IJ, Yeh JL. KMUP-1 Attenuates Endothelin-1-Induced Cardiomyocyte Hypertrophy through Activation of Heme Oxygenase-1 and Suppression of the Akt/GSK-3β, Calcineurin/NFATc4 and RhoA/ROCK Pathways. Molecules. 2015 Jun 5;20(6):10435-49. doi: 10.3390/molecules200610435. PubMed PMID: 26056815. 2: Dai ZK, Liu YW, Hsu JH, Yeh JL, Chen IJ, Wu JR, Wu BN. The Xanthine Derivative KMUP-1 Attenuates Serotonin-Induced Vasoconstriction and K⁺-Channel Inhibitory Activity via the PKC Pathway in Pulmonary Arteries. Int J Biol Sci. 2015 Apr 25;11(6):633-42. doi: 10.7150/ijbs.11127. eCollection 2015. PubMed PMID: 25999786; PubMed Central PMCID: PMC4440253. 3: Liou SF, Hsu JH, Chu HC, Lin HH, Chen IJ, Yeh JL. KMUP-1 Promotes Osteoblast Differentiation Through cAMP and cGMP Pathways and Signaling of BMP-2/Smad1/5/8 and Wnt/β-Catenin. J Cell Physiol. 2015 Sep;230(9):2038-48. doi: 10.1002/jcp.24904. PubMed PMID: 25536014. 4: Lo YC, Tseng YT, Liu CM, Wu BN, Wu SN. Actions of KMUP-1, a xanthine and piperazine derivative, on voltage-gated Na(+) and Ca(2+) -activated K(+) currents in GH3 pituitary tumour cells. Br J Pharmacol. 2015 Nov;172(21):5110-22. doi: 10.1111/bph.13276. Epub 2015 Oct 25. PubMed PMID: 26276211; PubMed Central PMCID: PMC4687803. 5: Wu JR, Kao LP, Wu BN, Dai ZK, Wang YY, Chai CY, Chen IJ. Buffered l-ascorbic acid, alone or bound to KMUP-1 or sildenafil, reduces vascular endothelium growth factor and restores endothelium nitric oxide synthase in hypoxic pulmonary artery. Kaohsiung J Med Sci. 2015 May;31(5):241-54. doi: 10.1016/j.kjms.2015.02.005. Epub 2015 Mar 23. PubMed PMID: 25910559. 6: Kuo KK, Wu BN, Liu CP, Yang TY, Kao LP, Wu JR, Lai WT, Chen IJ. Xanthine-based KMUP-1 improves HDL via PPARγ/SR-B1, LDL via LDLRs, and HSL via PKA/PKG for hepatic fat loss. J Lipid Res. 2015 Nov;56(11):2070-84. doi: 10.1194/jlr.M057547. Epub 2015 Sep 8. PubMed PMID: 26351364; PubMed Central PMCID: PMC4617394. 7: Dai ZK, Lin TC, Liou JC, Cheng KI, Chen JY, Chu LW, Chen IJ, Wu BN. Xanthine derivative KMUP-1 reduces inflammation and hyperalgesia in a bilateral chronic constriction injury model by suppressing MAPK and NFκB activation. Mol Pharm. 2014 May 5;11(5):1621-31. doi: 10.1021/mp5000086. Epub 2014 Apr 7. PubMed PMID: 24669856. 8: Liu CP, Kuo MS, Wu BN, Chai CY, Huang HT, Chung PW, Chen IJ. NO-releasing xanthine KMUP-1 bonded by simvastatin attenuates bleomycin-induced lung inflammation and delayed fibrosis. Pulm Pharmacol Ther. 2014 Feb;27(1):17-28. doi: 10.1016/j.pupt.2013.03.003. Epub 2013 Mar 19. PubMed PMID: 23518214. 9: Liu CP, Hsieh CH, Wu BN, Yeh JL, Dai ZK, Chai CY, Chen IJ. Inhaled KMUP-1 Prevents Allergic Pulmonary Vascular Inflammation and Remodeling via NO and Suppressed MMP-9 and ICAM-1/VCAM-1. Inflamm Allergy Drug Targets. 2012 Aug 1;11(4):251-61. PubMed PMID: 22452605. 10: Kuo KK, Wu BN, Chiu EY, Tseng CJ, Yeh JL, Liu CP, Chai CY, Chen IJ. NO donor KMUP-1 improves hepatic ischemia-reperfusion and hypoxic cell injury by inhibiting oxidative stress and pro-inflammatory signaling. Int J Immunopathol Pharmacol. 2013 Jan-Mar;26(1):93-106. PubMed PMID: 23527712. 11: Liou SF, Hsu JH, Lin IL, Ho ML, Hsu PC, Chen LW, Chen IJ, Yeh JL. KMUP-1 suppresses RANKL-induced osteoclastogenesis and prevents ovariectomy-induced bone loss: roles of MAPKs, Akt, NF-κB and calcium/calcineurin/NFATc1 pathways. PLoS One. 2013 Jul 25;8(7):e69468. doi: 10.1371/journal.pone.0069468. Print 2013. PubMed PMID: 23936022; PubMed Central PMCID: PMC3723916. 12: Wu BN, Kuo KK, Chen YH, Chang CT, Huang HT, Chai CY, Dai ZK, Chen IJ. Theophylline-Based KMUP-1 Improves Steatohepatitis via MMP-9/IL-10 and Lipolysis via HSL/p-HSL in Obese Mice. Int J Mol Sci. 2016 Aug 17;17(8). pii: E1345. doi: 10.3390/ijms17081345. PubMed PMID: 27548140; PubMed Central PMCID: PMC5000741. 13: Chen JY, Cheng KI, Tsai YL, Hong YR, Howng SL, Kwan AL, Chen IJ, Wu BN. Potassium-channel openers KMUP-1 and pinacidil prevent subarachnoid hemorrhage-induced vasospasm by restoring the BKCa-channel activity. Shock. 2012 Aug;38(2):203-12. doi: 10.1097/SHK.0b013e31825b2d82. PubMed PMID: 22576001. 14: Chung CL, Tsai HP, Lee KS, Chen KI, Wu SC, Kuo YH, Winardi W, Chen IC, Kwan AL. Assisted peripheral nerve recovery by KMUP-1, an activator of large-conductance Ca(2+)-activated potassium channel, in a rat model of sciatic nerve crush injury. Acta Neurochir (Wien). 2012 Oct;154(10):1773-9. doi: 10.1007/s00701-012-1433-y. Epub 2012 Jul 8. PubMed PMID: 22772399. 15: Yeh JL, Liu CP, Hsu JH, Tseng CJ, Wu PJ, Wang YY, Wu JR, Chen IJ. KMUP-1 inhibits hypertension-induced left ventricular hypertrophy through regulation of nitric oxide synthases, ERK1/2, and calcineurin. Kaohsiung J Med Sci. 2012 Nov;28(11):567-76. doi: 10.1016/j.kjms.2012.04.022. Epub 2012 Jul 25. PubMed PMID: 23140764. 16: Dai ZK, Kao CL, Hsieh SL, Chen IJ, Wu BN. Restoration of uridine 5'-triphosphate-suppressed delayed rectifying K(+) currents by an NO activator KMUP-1 involves RhoA/Rho kinase signaling in pulmonary artery smooth muscle cells. Kaohsiung J Med Sci. 2016 Dec;32(12):607-613. doi: 10.1016/j.kjms.2016.09.008. Epub 2016 Oct 27. PubMed PMID: 27914611. 17: Wu JR, Hsu JH, Dai ZK, Wu BN, Chen IJ, Liou SF, Yeh JL. Activation of endothelial NO synthase by a xanthine derivative ameliorates hypoxia-induced apoptosis in endothelial progenitor cells. J Pharm Pharmacol. 2016 Jun;68(6):810-8. doi: 10.1111/jphp.12555. Epub 2016 Apr 25. PubMed PMID: 27109251. 18: Wu BN, Chen HY, Liu CP, Hsu LY, Chen IJ. KMUP-1 inhibits H441 lung epithelial cell growth, migration and proinflammation via increased NO/CGMP and inhibited RHO kinase/VEGF signaling pathways. Int J Immunopathol Pharmacol. 2011 Oct-Dec;24(4):925-39. PubMed PMID: 22230399. 19: Liu CP, Dai ZK, Huang CH, Yeh JL, Wu BN, Wu JR, Chen IJ. Endothelial nitric oxide synthase-enhancing G-protein coupled receptor antagonist inhibits pulmonary artery hypertension by endothelin-1-dependent and endothelin-1-independent pathways in a monocrotaline model. Kaohsiung J Med Sci. 2014 Jun;30(6):267-78. doi: 10.1016/j.kjms.2014.02.014. Epub 2014 Apr 30. PubMed PMID: 24835346. 20: Yeh JL, Hsu JH, Wu PJ, Liou SF, Liu CP, Chen IJ, Wu BN, Dai ZK, Wu JR. KMUP-1 attenuates isoprenaline-induced cardiac hypertrophy in rats through NO/cGMP/PKG and ERK1/2/calcineurin A pathways. Br J Pharmacol. 2010 Mar;159(5):1151-60. doi: 10.1111/j.1476-5381.2009.00587.x. Epub 2010 Feb 2. PubMed PMID: 20132211; PubMed Central PMCID: PMC2839273.