Identification

Name
Hydroxyfasudil
Accession Number
DB04707
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
  • Hydroxy-Fasudil
Categories
UNII
Not Available
CAS number
105628-72-6
Weight
Average: 307.368
Monoisotopic: 307.099062115
Chemical Formula
C14H17N3O3S
InChI Key
ZAVGJDAFCZAWSZ-UHFFFAOYSA-N
InChI
InChI=1S/C14H17N3O3S/c18-14-12-3-1-4-13(11(12)5-7-16-14)21(19,20)17-9-2-6-15-8-10-17/h1,3-5,7,15H,2,6,8-10H2,(H,16,18)
IUPAC Name
5-(1,4-diazepane-1-sulfonyl)isoquinolin-1-ol
SMILES
OC1=C2C=CC=C(C2=CC=N1)S(=O)(=O)N1CCCNCC1

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
URho-associated protein kinase 1
inhibitor
Human
UcAMP-dependent protein kinase catalytic subunit alphaNot AvailableHuman
UcAMP-dependent protein kinase inhibitor alphaNot 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
DrugInteractionDrug group
DexketoprofenThe risk or severity of adverse effects can be increased when Dexketoprofen is combined with Hydroxyfasudil.Approved, Investigational
MecamylamineThe risk or severity of adverse effects can be increased when Hydroxyfasudil is combined with Mecamylamine.Approved
Food Interactions
Not Available

References

General References
Not Available
External Links
PubChem Compound
3064778
PubChem Substance
46508609
ChemSpider
2325236
BindingDB
50027431
ChEMBL
CHEMBL1233300
Therapeutic Targets Database
DNC000754
HET
HFS
PDB Entries
2erz / 2etk

Clinical Trials

Clinical Trials
Not Available

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 Solubility0.659 mg/mLALOGPS
logP-0.04ALOGPS
logP0.61ChemAxon
logS-2.7ALOGPS
pKa (Strongest Acidic)11.09ChemAxon
pKa (Strongest Basic)8.04ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area82.53 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity80.22 m3·mol-1ChemAxon
Polarizability31.07 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.997
Blood Brain Barrier+0.8489
Caco-2 permeable-0.6723
P-glycoprotein substrateSubstrate0.6958
P-glycoprotein inhibitor INon-inhibitor0.6954
P-glycoprotein inhibitor IINon-inhibitor0.9625
Renal organic cation transporterNon-inhibitor0.6941
CYP450 2C9 substrateNon-substrate0.6207
CYP450 2D6 substrateNon-substrate0.7713
CYP450 3A4 substrateNon-substrate0.5402
CYP450 1A2 substrateNon-inhibitor0.8454
CYP450 2C9 inhibitorNon-inhibitor0.8777
CYP450 2D6 inhibitorNon-inhibitor0.6308
CYP450 2C19 inhibitorNon-inhibitor0.8427
CYP450 3A4 inhibitorInhibitor0.5648
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.846
Ames testNon AMES toxic0.6497
CarcinogenicityNon-carcinogens0.8222
BiodegradationNot ready biodegradable0.956
Rat acute toxicity2.3948 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9302
hERG inhibition (predictor II)Inhibitor0.5474
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 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 isoquinolones and derivatives. These are aromatic polycyclic compounds containing a ketone bearing isoquinoline moiety.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Isoquinolines and derivatives
Sub Class
Isoquinolones and derivatives
Direct Parent
Isoquinolones and derivatives
Alternative Parents
Pyridinones / 1,4-diazepanes / Organosulfonamides / Benzenoids / Sulfonyls / Heteroaromatic compounds / Lactams / Dialkylamines / Azacyclic compounds / Organopnictogen compounds
show 3 more
Substituents
Isoquinolone / 1,4-diazepane / Diazepane / Pyridinone / Pyridine / Benzenoid / Organosulfonic acid amide / Heteroaromatic compound / Sulfonyl / Organosulfonic acid or derivatives
show 15 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
isoquinolines, N-sulfonyldiazepane (CHEBI:43149)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
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. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
  2. 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 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]

Drug created on September 11, 2007 11:49 / Updated on December 01, 2017 15:31