KMUP-1   Click here for help

GtoPdb Ligand ID: 8896

Synonyms: KMUP 1
Compound class: Synthetic organic
Comment: KMUP-1 is a novel xanthine-based activator of soluble guanylyl cyclase (sGC) (acts to enhance cGMP levels) reported to be useful clinically for tracheal relaxation [1]. It also has anti-inflammatory actions. Studies in aninals suggest this compound may also be a candidate for clinical investigation as a treatment for pulmonary arterial hypertension [2] or erectile dysfunction [3].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 5
Hydrogen bond donors 0
Rotatable bonds 4
Topological polar surface area 68.3
Molecular weight 402.16
XLogP 3.96
No. Lipinski's rules broken 0
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Canonical SMILES Clc1ccccc1N1CCN(CC1)CCn1cnc2c1c(=O)n(C)c(=O)n2C
Isomeric SMILES Clc1ccccc1N1CCN(CC1)CCn1cnc2c1c(=O)n(C)c(=O)n2C
InChI 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
1. Chen I-J, Wu B-N, Yeh J-L. (2008)
Anti-inflammation activity of newly synthesized xanthine derivatives kmup-1 and kmup-3.
Patent number: US20080081816 A1. Assignee: Kaohsiung Medical University. Priority date: 03/10/2006. Publication date: 03/04/2008.
2. Dai ZK, Cheng YJ, Chung HH, Wu JR, Chen IJ, Wu BN. (2010)
KMUP-1 ameliorates monocrotaline-induced pulmonary arterial hypertension through the modulation of Ca2+ sensitization and K+-channel.
Life Sci, 86 (19-20): 747-55. [PMID:20303989]
3. Lin RJ, Wu BN, Lo YC, Shen KP, Lin YT, Huang CH, Chen IJ. (2002)
KMUP-1 relaxes rabbit corpus cavernosum smooth muscle in vitro and in vivo: involvement of cyclic GMP and K(+) channels.
Br J Pharmacol, 135 (5): 1159-66. [PMID:11877322]
4. Liu CM, Lo YC, Wu BN, Wu WJ, Chou YH, Huang CH, An LM, Chen IJ. (2007)
cGMP-enhancing- and alpha1A/alpha1D-adrenoceptor blockade-derived inhibition of Rho-kinase by KMUP-1 provides optimal prostate relaxation and epithelial cell anti-proliferation efficacy.
Prostate, 67 (13): 1397-410. [PMID:17639498]
5. Lo YC, Tseng YT, Liu CM, Wu BN, Wu SN. (2015)
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, 172 (21): 5110-22. [PMID:26276211]
6. Wu BN, Lin RJ, Lin CY, Shen KP, Chiang LC, Chen IJ. (2001)
A xanthine-based KMUP-1 with cyclic GMP enhancing and K(+) channels opening activities in rat aortic smooth muscle.
Br J Pharmacol, 134 (2): 265-74. [PMID:11564644]
7. Wu BN, Lin RJ, Lo YC, Shen KP, Wang CC, Lin YT, Chen IJ. (2004)
KMUP-1, a xanthine derivative, induces relaxation of guinea-pig isolated trachea: the role of the epithelium, cyclic nucleotides and K+ channels.
Br J Pharmacol, 142 (7): 1105-14. [PMID:15237094]