Identification

Name
Fasudil
Accession Number
DB08162  (DB12469)
Type
Small Molecule
Groups
Investigational
Description

Fasudil has been investigated in Carotid Stenosis.

Structure
Thumb
Synonyms
Not Available
External IDs
AT 877 / AT-877 / HA 1077 / HA-1077 / ZK-258594
Product Ingredients
IngredientUNIICASInChI Key
Fasudil hydrochlorideSQ04N8S7BR105628-07-7LFVPBERIVUNMGV-UHFFFAOYSA-N
Categories
UNII
Q0CH43PGXS
CAS number
103745-39-7
Weight
Average: 291.369
Monoisotopic: 291.104147493
Chemical Formula
C14H17N3O2S
InChI Key
NGOGFTYYXHNFQH-UHFFFAOYSA-N
InChI
InChI=1S/C14H17N3O2S/c18-20(19,17-9-2-6-15-8-10-17)14-4-1-3-12-11-16-7-5-13(12)14/h1,3-5,7,11,15H,2,6,8-10H2
IUPAC Name
5-(1,4-diazepane-1-sulfonyl)isoquinoline
SMILES
O=S(=O)(N1CCCNCC1)C1=CC=CC2=C1C=CN=C2

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UcAMP-dependent protein kinase inhibitor alphaNot AvailableHuman
UcAMP-dependent protein kinase catalytic subunit alphaNot AvailableHuman
URho-associated protein kinase 1Not AvailableHuman
URho-associated protein kinase 2Not AvailableHuman
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
PubChem Compound
3547
PubChem Substance
99444633
ChemSpider
3426
BindingDB
14027
ChEMBL
CHEMBL38380
HET
M77
Wikipedia
Fasudil
PDB Entries
1q8w / 2esm / 2f2u / 2gni / 3tku / 5vef

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
2CompletedTreatmentAtherosclerosis / High Blood Cholesterol Level1
2Unknown StatusNot AvailableCarotid Stenosis1
2Unknown StatusTreatmentAmyotrophic Lateral Sclerosis (ALS)1
2, 3RecruitingTreatmentRetinal Vein Occlusions(RVO)1
3CompletedTreatmentRaynaud's Disease / Scleroderma1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.531 mg/mLALOGPS
logP0.16ALOGPS
logP0.32ChemAxon
logS-2.7ALOGPS
pKa (Strongest Basic)8.04ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area62.3 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity77.92 m3·mol-1ChemAxon
Polarizability29.6 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9614
Caco-2 permeable-0.6507
P-glycoprotein substrateSubstrate0.5902
P-glycoprotein inhibitor INon-inhibitor0.616
P-glycoprotein inhibitor IINon-inhibitor0.8386
Renal organic cation transporterNon-inhibitor0.5342
CYP450 2C9 substrateNon-substrate0.7243
CYP450 2D6 substrateNon-substrate0.7464
CYP450 3A4 substrateNon-substrate0.5632
CYP450 1A2 substrateNon-inhibitor0.9046
CYP450 2C9 inhibitorNon-inhibitor0.907
CYP450 2D6 inhibitorInhibitor0.7888
CYP450 2C19 inhibitorNon-inhibitor0.9026
CYP450 3A4 inhibitorInhibitor0.7959
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.73
Ames testNon AMES toxic0.682
CarcinogenicityNon-carcinogens0.8969
BiodegradationNot ready biodegradable0.9793
Rat acute toxicity2.5211 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.7322
hERG inhibition (predictor II)Inhibitor0.5551
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as isoquinolines and derivatives. These are aromatic polycyclic compounds containing an isoquinoline moiety, which consists of a benzene ring fused to a pyridine ring and forming benzo[c]pyridine.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Isoquinolines and derivatives
Sub Class
Not Available
Direct Parent
Isoquinolines and derivatives
Alternative Parents
1,4-diazepanes / Pyridines and derivatives / Organosulfonamides / Benzenoids / Sulfonyls / Heteroaromatic compounds / Dialkylamines / Azacyclic compounds / Organopnictogen compounds / Organic oxides
show 1 more
Substituents
Isoquinoline / 1,4-diazepane / Diazepane / Pyridine / Organosulfonic acid amide / Benzenoid / Organic sulfonic acid or derivatives / Organosulfonic acid or derivatives / Sulfonyl / Heteroaromatic compound
show 12 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Protein kinase a catalytic subunit binding
Specific Function
Extremely potent competitive inhibitor of cAMP-dependent protein kinase activity, this protein interacts with the catalytic subunit of the enzyme after the cAMP-induced dissociation of its regulato...
Gene Name
PKIA
Uniprot ID
P61925
Uniprot Name
cAMP-dependent protein kinase inhibitor alpha
Molecular Weight
7988.435 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Ubiquitin protein ligase binding
Specific Function
Phosphorylates a large number of substrates in the cytoplasm and the nucleus. Regulates the abundance of compartmentalized pools of its regulatory subunits through phosphorylation of PJA2 which bin...
Gene Name
PRKACA
Uniprot ID
P17612
Uniprot Name
cAMP-dependent protein kinase catalytic subunit alpha
Molecular Weight
40589.38 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Protein serine/threonine kinase activity
Specific Function
Protein kinase which is a key regulator of actin cytoskeleton and cell polarity. Involved in regulation of smooth muscle contraction, actin cytoskeleton organization, stress fiber and focal adhesio...
Gene Name
ROCK1
Uniprot ID
Q13464
Uniprot Name
Rho-associated protein kinase 1
Molecular Weight
158173.545 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Structural molecule activity
Specific Function
Protein kinase which is a key regulator of actin cytoskeleton and cell polarity. Involved in regulation of smooth muscle contraction, actin cytoskeleton organization, stress fiber and focal adhesio...
Gene Name
ROCK2
Uniprot ID
O75116
Uniprot Name
Rho-associated protein kinase 2
Molecular Weight
160898.555 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]

Drug created on September 15, 2010 15:28 / Updated on December 01, 2017 17:36