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MedKoo Cat#: 529418 | Name: KR-31378

Description:

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

KR-31378, also known as DNB-001 and MSH-1001, is a K(ATP) channel activator potentially for the treatment of ocular hypertension and glaucoma

Chemical Structure

KR-31378
KR-31378
CAS#335381-68-5

Theoretical Analysis

MedKoo Cat#: 529418

Name: KR-31378

CAS#: 335381-68-5

Chemical Formula: C22H27N5O4

Exact Mass: 425.2063

Molecular Weight: 425.48

Elemental Analysis: C, 62.10; H, 6.40; N, 16.46; O, 15.04

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.
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Related CAS #
No Data
Synonym
DNB-001; KR-31378; MSH-1001; DNB001; KR31378; MSH1001; DNB 001; KR 31378; MSH 1001
IUPAC/Chemical Name
Guanidine, N-((2S,3S,4R)-6-amino-2-(dimethoxymethyl)-3,4-dihydro-3-hydroxy-2-methyl-2H-1-benzopyran-4-yl)-N'-cyano-N''-(phenylmethyl)-
InChi Key
OZHUPJHJQIEDFA-DXIQSLLYSA-N
InChi Code
InChI=1S/C22H27N5O4/c1-22(20(29-2)30-3)19(28)18(16-11-15(24)9-10-17(16)31-22)27-21(26-13-23)25-12-14-7-5-4-6-8-14/h4-11,18-20,28H,12,24H2,1-3H3,(H2,25,26,27)/t18-,19+,22+/m1/s1
SMILES Code
N#CN/C(N[C@H]1[C@H](O)[C@@](C)(C(OC)OC)OC2=CC=C(N)C=C12)=N/CC3=CC=CC=C3
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

Preparing Stock Solutions

The following data is based on the product molecular weight 425.48 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
1: Choi A, Choi JS, Yoon YJ, Kim KA, Joo CK. KR-31378, a potassium-channel opener, induces the protection of retinal ganglion cells in rat retinal ischemic models. J Pharmacol Sci. 2009 Apr;109(4):511-7. PubMed PMID: 19372634. 2: Hwang GS, Oh KS, Koo HN, Seo HW, You KH, Lee BH. Effects of KR-31378, a novel ATP-sensitive potassium channel activator, on hypertrophy of H9c2 cells and on cardiac dysfunction in rats with congestive heart failure. Eur J Pharmacol. 2006 Jul 1;540(1-3):131-8. PubMed PMID: 16729997. 3: Lee CH, Choi KY, Kim YJ, Kim WG. Neuroprotective effect of KR-31378, a novel potassium channel activator, on spinal cord ischemic injury in rabbits. J Invest Surg. 2005 Nov-Dec;18(6):297-304. PubMed PMID: 16319050. 4: Kim MY, Lee S, Yi KY, Yoo SE, Lee DH, Lim H, Kim HS, Lee SH, Baik EJ, Moon CH, Jung YS. Protective effect of KR-31378 on oxidative stress in cardiac myocytes. Arch Pharm Res. 2005 Dec;28(12):1358-64. PubMed PMID: 16392669. 5: Moon CH, Kim MY, Kim MJ, Kim MH, Lee S, Yi KY, Yoo SE, Lee DH, Lim H, Kim HS, Lee SH, Baik EJ, Jung YS. KR-31378, a novel benzopyran analog, attenuates hypoxia-induced cell death via mitochondrial KATP channel and protein kinase C-epsilon in heart-derived H9c2 cells. Eur J Pharmacol. 2004 Dec 3;506(1):27-35. PubMed PMID: 15588621. 6: Kim KY, Lee JH, Park JH, Yoo MA, Kwak YG, Kim SO, Yoo SE, Hong KW. Anti-apoptotic action of (2S,3S,4R)-N"-cyano-N-(6-amino-3,4-dihydro-3-hydroxy-2-methyl-2-dimethoxymethyl-2 H-benzopyran-4-yl)-N'-benzylguanidine (KR-31378) by suppression of the phosphatase and tensin homolog deleted from chromosome 10 phosphorylation and increased phosphorylation of casein kinase2/Akt/ cyclic AMP response element binding protein via maxi-K channel opening in neuronal cells. Eur J Pharmacol. 2004 Aug 30;497(3):267-77. PubMed PMID: 15336944. 7: Won R, Lim JY, Lee SY, Park JH, Sohn NW. Neuroprotective effect of KR-31378 via KATP channel opening against ischemic insult. Biol Pharm Bull. 2004 Aug;27(8):1285-8. PubMed PMID: 15305038. 8: Jung YS, Lee DH, Lim H, Yi KY, Yoo SE, Kim E. KR-31378 protects cardiac H9c2 cells from chemical hypoxia-induced cell death via inhibition of JNK/p38 MAPK activation. Jpn J Physiol. 2004 Dec;54(6):575-83. PubMed PMID: 15760490. 9: Kim SO, Cho IS, Gu HK, Lee DH, Lim H, Yoo SE. KR-31378 protects neurons from ischemia-reperfusion brain injury by attenuating lipid peroxidation and glutathione loss. Eur J Pharmacol. 2004 Mar 8;487(1-3):81-91. PubMed PMID: 15033379. 10: Kim SO, Kwak SH, Lee BH, Lee DH, Lim H, Yoo SE, Chung HJ, Lee MG. Dose-dependent pharmacokinetics of KR-31378, a new neuroprotective agent for ischaemia-reperfusion damage in dogs. Biopharm Drug Dispos. 2004 Apr;25(3):143-8. PubMed PMID: 15083503. 11: Kim J, Nam KH, Kim SO, Choi JH, Kim HC, Yang SD, Kang JH, Ryu YH, Oh GT, Yoo SE. KR-31378 ameliorates atherosclerosis by blocking monocyte recruitment in hypercholestrolemic mice. FASEB J. 2004 Apr;18(6):714-6. PubMed PMID: 14766797. 12: Jeong TC, Kim JY, Ji HY, Lee DH, Kim SO, Lim H, Yoo SE, Lee HS. Effects of a new neuroprotective agent KR-31378 on liver cytochrome P450s in male Sprague Dawley rats. Arch Pharm Res. 2003 Oct;26(10):800-4. PubMed PMID: 14609126. 13: Sohn YT, Park BY. Characterization of the physicochemical properties of KR-31378. Arch Pharm Res. 2003 Jul;26(7):526-31. PubMed PMID: 12934643. 14: Ki J, Ji HY, Yoo SE, Kim SO, Lee DH, Lim H, Lee HS. Simultaneous determination of the novel neuroprotective agent KR-31378 and its metabolite KR-31612 using high performance liquid chromatography with tandem mass spectrometry in human plasma. Arch Pharm Res. 2002 Oct;25(5):647-51. PubMed PMID: 12433199. 15: Hong KW, Kim KY, Lee JH, Shin HK, Kwak YG, Kim SO, Lim H, Yoo SE. Neuroprotective effect of (2S,3S,4R)-N"-cyano-N-(6-amino-3, 4-dihydro-3-hydroxy-2-methyl-2-dimethoxymethyl-2H-benzopyran-4-yl)-N'-benzylguani dine (KR-31378), a benzopyran analog, against focal ischemic brain damage in rats. J Pharmacol Exp Ther. 2002 Apr;301(1):210-6. PubMed PMID: 11907175. 16: Kim HJ, Kim SH, Kim SO, Lee DH, Lim H, Yoo SE, Lee MG. Dose-dependent pharmacokinetics of a new neuroprotective agent for ischemia-reperfusion damage, KR-31378, in rats. Biopharm Drug Dispos. 2000 Oct;21(7):279-84. PubMed PMID: 11512127. 17: Lee MH, Kim HJ, Kim SH, Kim SO, Lee DH, Lim H, Yoo SE, Lee MG. High-performance liquid chromatographic analysis of a new neuroprotective agent for ischemia-reperfusion damage, KR-31378. Res Commun Mol Pathol Pharmacol. 2001 Mar-Apr;109(3-4):249-56. PubMed PMID: 11758654. 18: Lee MH, Kim HJ, Kim SH, Kim SO, Lee DH, Lim H, Yoo SE, Lee MG. Blood partition and protein binding of a new neuroprotective agent for ischemia-reperfusion damage, KR-31378. Res Commun Mol Pathol Pharmacol. 2001;110(5-6):361-70. PubMed PMID: 12889527. 19: Kim KY, Kim BG, Kim SO, Yoo SE, Kwak YG, Chae SW, Hong KW. Prevention of lipopolysaccharide-induced apoptosis by (2S,3S,4R)-N"-cyano-N-(6-amino-3,4-dihydro-3-hydroxy-2-methyl-2-dimethoxymethyl-2 H-benzopyran-4-yl)-N'-benzylguanidine, a benzopyran analog, in endothelial cells. J Pharmacol Exp Ther. 2002 Feb;300(2):535-42. PubMed PMID: 11805214. 20: Kim NS, Yoo HH, Lee MW, Kim HS, Kim DH. Disposition and metabolism of (2S,3S,4R)-N''-cyano-N-(6-amino-3,4-dihydro-3-hydroxy-2-methyl-2-dimethoxy methyl-2H-benzopyran-4-yl)-N'-benzylguanidine, a novel neuroprotective agent for ischemia-reperfusion damage, in rats. Xenobiotica. 2007 May;37(5):534-48. PubMed PMID: 17523055.