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Details

Stereochemistry RACEMIC
Molecular Formula C14H16N6O
Molecular Weight 284.3164
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of SIGUAZODAN

SMILES

CN\C(NC#N)=N/C1=CC=C(C=C1)C2=NNC(=O)CC2C

InChI

InChIKey=NUHPODZZKHQQET-UHFFFAOYSA-N
InChI=1S/C14H16N6O/c1-9-7-12(21)19-20-13(9)10-3-5-11(6-4-10)18-14(16-2)17-8-15/h3-6,9H,7H2,1-2H3,(H,19,21)(H2,16,17,18)

HIDE SMILES / InChI

Molecular Formula C14H16N6O
Molecular Weight 284.3164
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 1
Optical Activity ( + / - )

Description

Siguazodan is a selective inhibitor of phosphodiesterase 3. It caused significant increases in cardiac output and stroke volume. It is orally active inotropic/vasodilator agent with a sustained duration in vivo. Siguazodan has potential utility in the treatment of congestive heart failure. Siguazodan has anti-platelet actions over the same concentration range that it is an inotrope and vasodilator. Siguazodan caused bronchodilation. In combination with phosphodiesterase 4, it may be useful in the therapy of asthma.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
117.0 nM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown
Primary
Unknown

PubMed

Sample Use Guides

In Vivo Use Guide
Dog: 25, 50 and 100 ug/kg
Route of Administration: Intravenous
In Vitro Use Guide
Among the ways in which cyclic AMP inhibits platelet function is a reduction in signal transduction and in Ca2+ mobilization. Therefore examined the effect of siguazodan on stimulated increases in [Ca2+]i in quin 2-loaded platelets resuspended in HEPES-buffered saline was examined. Siguazodan, was able to inhibit almost completely the [Ca2+]i elevation evoked by 20 uM ADP. The calculated ICjo for this effect was 1.5 uM
Substance Class Chemical
Record UNII
5E4UI00UQJ
Record Status Validated (UNII)
Record Version