Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C14H16N2O4 |
Molecular Weight | 276.2878 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 2 / 2 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@@]1([C@H](O)C(C)(C)OC2=CC=C(C=C12)C#N)N(O)C(C)=O
InChI
InChIKey=IWTCFIIOUXJOOV-OLZOCXBDSA-N
InChI=1S/C14H16N2O4/c1-8(17)16(19)12-10-6-9(7-15)4-5-11(10)20-14(2,3)13(12)18/h4-6,12-13,18-19H,1-3H3/t12-,13+/m1/s1
Y-26763 is an active metabolite of Y-27152. Y-26763 is the novel K channel opener. It has been found to activate K channels in both cardiac myocytes and in smooth muscle cells from various tissues, suggesting that the compound has a non-specific effect on SUR1 and SUR2 channel subunits. Y-26763 well tolerated in healthy volunteers, and its pharmacologic effects were likely caused by vasodilation, which could make it an effective antihypertensive agent. At doses of 0.5 mg or higher, participants experienced headaches and palpitations, which were probably due to the vasodilatory effects and did not require treatment. Y-26763 partially protected against glycerol-induced acute renal failure. Also, it reduces infarct volume in focal cerebral ischemia in rats.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL2071 Sources: https://www.ncbi.nlm.nih.gov/pubmed/14975702 |
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Target ID: CHEMBL1971 Sources: https://www.ncbi.nlm.nih.gov/pubmed/14975702 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | Unknown Approved UseUnknown |
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Preventing | Unknown Approved UseUnknown |
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Preventing | Unknown Approved UseUnknown |
Doses
Dose | Population | Adverse events |
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1 mg 1 times / day multiple, oral (unknown) Highest studied dose Dose: 1 mg, 1 times / day Route: oral Route: multiple Dose: 1 mg, 1 times / day Sources: |
healthy n = 9 Health Status: healthy Sex: M Food Status: UNKNOWN Population Size: 9 Sources: |
Other AEs: headache... |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
headache | 1 mg 1 times / day multiple, oral (unknown) Highest studied dose Dose: 1 mg, 1 times / day Route: oral Route: multiple Dose: 1 mg, 1 times / day Sources: |
healthy n = 9 Health Status: healthy Sex: M Food Status: UNKNOWN Population Size: 9 Sources: |
PubMed
Title | Date | PubMed |
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Y-26763 protects the working rat myocardium from ischemia/reperfusion injury through opening of KATP channels. | 1996 Dec 19 |
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Age-related changes in response of brain stem vessels to opening of ATP-sensitive potassium channels. | 1997 Jan |
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Role of potassium channels in halothane-epinephrine arrhythmias. | 1998 Jun |
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Long-term effects of benidipine on cerebral vasoreactivity in hypertensive rats. | 2002 Mar 8 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/8739023
Curator's Comment: Y-27152 itself is pharmacologically inert and is converted to its active form, Y-26763, after oral administration.
In the first phase, single doses of 0.1, 0.25, 0.5, 0.75, and 1.0 mg of Y-27152 were given after overnight fasts in a dose-escalating manner. The 0.75-mg dose was given both after an overnight fast or after food to examine the effects of food intake. In the second phase, multiple doses of Y-27152 were taken after meals once daily for 7 consecutive days. In part A of this phase, either placebo or 0.5 mg of Y-27152 was taken for 7 days, and in part B of this phase 0.5-, 0.75-, and 1.0-mg doses were taken in a dose-escalating manner for 1,3, and 3 days, respectively.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/1578381
Y-26763 concentration dependently relaxed the contraction induced by 20 mM KCL in rat aortic rings with an IC50 value of 0.027 uM, being ineffective against 80 mM KCL contraction.
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DTXSID80155562
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127408-31-5
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121878
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ACTIVE MOIETY
PARENT (METABOLITE ACTIVE)