| Stereochemistry | RACEMIC |
| Molecular Formula | C22H29N3O3.ClH |
| Molecular Weight | 419.945 |
| Optical Activity | ( + / - ) |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.CCN(CC)CCCCC(NC(=O)C1=CC=C(C=C1)[N+]([O-])=O)C2=CC=CC=C2
InChI
InChIKey=CHCBAYRWJULIDW-UHFFFAOYSA-N
InChI=1S/C22H29N3O3.ClH/c1-3-24(4-2)17-9-8-12-21(18-10-6-5-7-11-18)23-22(26)19-13-15-20(16-14-19)25(27)28;/h5-7,10-11,13-16,21H,3-4,8-9,12,17H2,1-2H3,(H,23,26);1H
| Molecular Formula | ClH |
| Molecular Weight | 36.461 |
| Charge | 0 |
| Count |
MOL RATIO
1 MOL RATIO (average) |
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
| Molecular Formula | C22H29N3O3 |
| Molecular Weight | 383.484 |
| Charge | 0 |
| Count |
MOL RATIO
1 MOL RATIO (average) |
| Stereochemistry | RACEMIC |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Optical Activity | ( + / - ) |
Nebentan (YM598) is an orally active synthetic substituted phenylethenesulfonamide. As a selective endothelin A receptor antagonist, YM598 inhibits endothelin-mediated mechanisms involved in tumor cell growth and progression, angiogenesis, and metastasis. The inhibitory dissociation constant value of YM598 was 0.772 nM for native human ETA receptors, and 143 nM for native human ETB subtypes. The calculated selectivity ratio of YM598 for ETA versus ETB receptors was 222. In pithed rats, YM598 inhibited the big endothelin-1 (1 nmol/kg)-induced pressor response in a dose-dependent manner, after both intravenous and oral administration. YM598 showed not only superior antagonistic activity and higher-selectivity for endothelin ET(A) receptor in vitro, but at least a 30-fold higher potency in vivo than bosentan.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
PubMed
Sample Use Guides
In the in vivo study, endothelin-1 induced the elevation of non-prostatic urethral pressure as well as prostatic urethral pressure even in the presence of tamsulosin (10 microg/kg, i.v.) in anesthetized male dogs. Nebentan (0.1-3 mg/kg, i.v.) inhibited these endothelin-1-induced contractile responses in a dose-dependent fashion.
Route of Administration:
Intravenous
In the in vitro study, endothelin-1 induced contractile responses in isolated rabbit bladder base, urethra, and prostate tissues. Nebentan (10(-7)-10(-5) M) antagonized endothelin-1-induced contractile responses without affecting the maximal responses. YM598 inhibited [125I]endothelin-1 binding to cloned human endothelin ET(A) and ET(B) receptor, with K(i) of 0.697 and 569 nM, and inhibited endothelin-1-induced increases in intracellular Ca(2+) concentration in human and rat endothelin ET(A) receptor. YM598 also inhibited endothelin-1-induced vasoconstriction in isolated rat aorta with a pA(2) value of 7.6.
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PARENT -> SALT/SOLVATE |
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