Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C26H31N3O4 |
| Molecular Weight | 449.542 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CC(=O)NCCCOC1=CC=C(C=C1)C(=O)N2CCC(CC2)N3C(=O)CCC4=C3C=CC=C4
InChI
InChIKey=KSNUCNRMDYJBKT-UHFFFAOYSA-N
InChI=1S/C26H31N3O4/c1-19(30)27-15-4-18-33-23-10-7-21(8-11-23)26(32)28-16-13-22(14-17-28)29-24-6-3-2-5-20(24)9-12-25(29)31/h2-3,5-8,10-11,22H,4,9,12-18H2,1H3,(H,27,30)
DescriptionCurator's Comment: Description was created based on several sources, including http://adisinsight.springer.com/drugs/800000284 | https://www.ncbi.nlm.nih.gov/pubmed/8228734
Curator's Comment: Description was created based on several sources, including http://adisinsight.springer.com/drugs/800000284 | https://www.ncbi.nlm.nih.gov/pubmed/8228734
OPC-21268, a non-peptide vasopressin V1 receptor antagonist, inhibited oxytocin- and vasopressin-induced contractions of myometrial strips from rats and from full-term pregnant women. OPC-21268, because of its non-peptide structure, is orally active and has been shown to lower blood pressure in a patient with congestive heart failure and in spontaneously hypertensive rats. It also attenuates vasopressin induced bradycardia in rabbits and pressor responses in rats. It has been demonstrated that OPC-21268 exerts its inhibitory action through binding to the vasopressin V1 receptors in rat liver and kidney. Finally, OPC-21268 was reported to be safe and non-toxic in healthy humans. Merck scientists showed that OPC-21268 had significant affinity for the rOTR and the hOTR. OPC-21268 has been in phase II clinical trials by Otsuka for the treatment of heart failure and hypertension. However, this research has been discontinued.
Originator
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Characterization of the human oxytocin receptor stably expressed in 293 human embryonic kidney cells. | 1995 |
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| The human V3 pituitary vasopressin receptor: ligand binding profile and density-dependent signaling pathways. | 1997 Oct |
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| Vasopressin stimulates insulin release from islet cells through V1b receptors: a combined pharmacological/knockout approach. | 2004 Mar |
|
| Impaired arginine-vasopressin-induced aldosterone release from adrenal gland cells in mice lacking the vasopressin V1A receptor. | 2007 Jul 2 |
Patents
Sample Use Guides
Single oral administration of OPC-21268 (100 mg) in hypertensive patients on diets
Route of Administration:
Oral
In Vitro Use Guide
Curator's Comment: In human internal mammary arteries, the non-peptide V1 receptor antagonist, OPC-21268, failed to antagonize vasopressin-induced contraction at low concentrations and potentiated the contraction at higher concentrations (300 nmol/l, P < 0.05). In rat mesenteric resistance arteries, OPC-21268 (10 nmol/l) antagonized vasopressin-induced contraction
In endothelium-intact human coronary artery segments, OPC-21268 (3uM) induced a rightward shift of the vasopressin concentration-response curve.
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131631-89-5
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33U7944QCQ
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DTXSID70927295
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SUBSTANCE RECORD
