SIGUAZODAN

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 Search

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

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	1
Optical Activity	( + / - )

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/3390657 | https://www.ncbi.nlm.nih.gov/pubmed/2158847 | https://www.ncbi.nlm.nih.gov/pubmed/1665307 | https://www.ncbi.nlm.nih.gov/pubmed/8035322

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 Target	Pharmacology	Condition	Potency
Phosphodiesterase 3 60 Target ID: CHEMBL2094125 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7925608	Inhibitor 8297		117.0 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Congestive heart failure 54 Sources: https://www.ncbi.nlm.nih.gov/pubmed/3390657	Primary		Preclinical	Unknown Approved Use Unknown
Asthma 241 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8035322 https://www.ncbi.nlm.nih.gov/pubmed/1665307	Primary		Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Hypoxic vasoconstriction of rat main pulmonary artery: role of endogenous nitric oxide, potassium channels, and phosphodiesterase inhibition.	2001 Aug	11483882
Relaxant effects of selective phosphodiesterase inhibitors on U46619 precontracted human intralobar pulmonary arteries and role of potassium channels.	2002 Jul	12072589
Phosphodiesterase 4 inhibitors modulate beta2-adrenoceptor agonist-induced human airway hyperresponsiveness.	2006 Oct 12	16820175
Cyclic-AMP-dependent proliferation of a human osteoblast cell line (HOS cells) induced by hydroxyapatite: effect of exogenous nitric oxide.	2008 Aug	18788505
Superiority of combined phosphodiesterase PDE3/PDE4 inhibition over PDE4 inhibition alone on glucocorticoid- and long-acting β2-adrenoceptor agonist-induced gene expression in human airway epithelial cells.	2015 Jan	25324049

Patents

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 Created by `admin` on `Fri Dec 15 16:11:10 GMT 2023` Edited by `admin` on `Fri Dec 15 16:11:10 GMT 2023`
Record UNII	5E4UI00UQJ
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

SIGUAZODAN

Official Name

English

SK&F-94836

Code

English

SK&F 94836

Code

English

siguazodan [INN]

Common Name

English

SKF-94836

Code

English

GUANIDINE, N-CYANO-N'-METHYL-N''-(4-(1,4,5,6-TETRAHYDRO-4-METHYL-6-OXO-3-PYRIDAZINYL)PHENYL)-, (±)-

Systematic Name

English

Classification Tree Code System Code

NCI_THESAURUS

C744