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Details

Stereochemistry ABSOLUTE
Molecular Formula C15H20N6O6
Molecular Weight 380.3559
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TRABODENOSON

SMILES

O[C@@H]1[C@@H](CO[N+]([O-])=O)O[C@H]([C@@H]1O)N2C=NC3=C2N=CN=C3NC4CCCC4

InChI

InChIKey=AQLVRTWKJDTWQQ-SDBHATRESA-N
InChI=1S/C15H20N6O6/c22-11-9(5-26-21(24)25)27-15(12(11)23)20-7-18-10-13(16-6-17-14(10)20)19-8-3-1-2-4-8/h6-9,11-12,15,22-23H,1-5H2,(H,16,17,19)/t9-,11-,12-,15-/m1/s1

HIDE SMILES / InChI

Molecular Formula C15H20N6O6
Molecular Weight 380.3559
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 4 / 4
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Trabodenoson is a potent (Ki = 0.97 nM) and selective (>10,000- fold vs. adenosine 2 receptor) adenosine 1 receptor agonist. Ex vivo, trabodenoson (100 nM to 3 uM) progressively prolonged A-V-nodal conduction without reducing left ventricular function or coronary resistance. In vivo, trabodenoson up to a dose of 50 ug/kg did not reduce the carotid arterial blood pressure. Twice-daily ocular doses of trabodenoson, from 50 to 500 ug, were well tolerated and showed a dose-related decrease in intraocular pressure that was statistically significant and clinically relevant at 500 ug in patients with ocular hypertension or primary open-angle glaucoma. Trabodenoson had been in phase III clinical trial for the treatment of glaucoma and ocular hypertension. However, this development was discontinued.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

PubMed

Patents

Sample Use Guides

In Vivo Use Guide
50, 100, or 200 ug for 14 days or 500 ug for 28 days
Route of Administration: Topical
Substance Class Chemical
Record UNII
1T237110W4
Record Status Validated (UNII)
Record Version