5-(1,4-diazepane-1-sulfonyl)isoquinolin-1-ol hydrochloride

• ChemBase ID: 154243
• Molecular Formular: C14H18ClN3O3S
• Molecular Mass: 343.82902
• Monoisotopic Mass: 343.07574013
• SMILES: c1cc2c(ccnc2O)c(c1)S(=O)(=O)N1CCCNCC1.Cl
• Canonical SMILES: Oc1nccc2c1cccc2S(=O)(=O)N1CCNCCC1.Cl
• InChI: InChI=1S/C14H17N3O3S.ClH/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);1H
• InChIKey: XWWFOUVDVJGNNG-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-(1,4-diazepane-1-sulfonyl)isoquinolin-1-ol hydrochloride
• IUPAC Traditional name: hydroxyfasudil hydrochloride
• Synonyms: 1-(1-Hydroxy-5-isoquinolinesulfonyl)homopiperazine hydrochloride hydrate; Hydroxyfasudil hydrochloride hydrate; 1-(1-Hydroxy-5-isoquinolinesulfonyl)homopiperazine Hydrochloride; 5-[(Hexahydro-1H-1,4-diazepin-1-yl)sulfonyl]-1(2H)-isoquinolinone; HA1100 Hydrochloride; Hydroxy Fasudil Hydrochloride

Database IDs

• CAS Number: 155558-32-0; 155558-32-0(anhydrous)
• MDL Number: MFCD06411567
• PubChem SID: 162248382; 24724499
• PubChem CID: 11371328

CALCULATED PROPERTIES

• Acid pKa: 11.086961
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): -1.8469429
• LogD (pH = 7.4): -0.1131061
• Log P: 0.61335665
• Molar Refractivity: 80.2178 cm^3
• Polarizability: 32.829594 Å^3
• Polar Surface Area: 82.53 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Aqueous Acid; H2O: >5 mg/mL; Methanol (Sparingly)
• Apperance: Off-White Solid; white solid
• Melting Point: >250°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Compostion: The two peaks show the equilibrim between the two tautomers
• Empirical Formula (Hill Notation): C14H17N3O3S · HCl · xH2O

DETAILS

Sigma Aldrich - H4413

Biochem/physiol Actions
Rho-kinase inhibitor.

Toronto Research Chemicals - H942380

A metabolite of Fasudil. A cell-permeable, hydroxylated metabolite of HA 1077 that displays anti-anginal properties. Reported to inhibit the Rho kinase-mediated (ROCK) contraction both in vitro and in vivo.

REFERENCES

• Shimokawa, H., et al.: Cardiovasc. Res., 43, 1029 (1999)
• Takemoto, M., et al.: Circulation, 106, 57 (1999)
• Ito, K., et al.: J. Physiol., 546, 823 (1999)