Fasudil hydrochloride Chemical Properties

Melting point:

220.5°; mp 219.3° (Shirotani)

storage temp. 

Inert atmosphere,Store in freezer, under -20°C

solubility 

H₂O: >200 mg/mL

form 

solid

color 

white

Water Solubility 

Soluble in water and dimethyl sulfoxide. Insoluble in ethanol.

Merck 

14,3942

Stability:

Stable for 2 years from date of purchase as supplied. Solutions in DMSO or distilled water may be stored at -20° for up to 1 month.

InChI

InChI=1S/C14H17N3O2S.2ClH/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;2*1H

InChIKey

LFVPBERIVUNMGV-UHFFFAOYSA-N

SMILES

N1(S(C2=CC=CC3=C2C=CN=C3)(=O)=O)CCCNCC1.[H]Cl.[H]Cl

CAS DataBase Reference

105628-07-7(CAS DataBase Reference)

Safety Information

Risk Statements 

22

Safety Statements 

36-60

WGK Germany 

3

RTECS 

HM4031166

HS Code 

29339900

Toxicity

LD50 in mice, rats (mg/kg): 67.5, 59.9 i.v.; 124.5, 123.2 s.c.; 273.9, 335.0 orally (Koga)

MSDS

• Language:English Provider:SigmaAldrich

Fasudil hydrochloride Usage And Synthesis

Indications and Usage

Fasudil Hydrochloride is a new drug with a wide range of pharmacological effects, developed by Asahi Kasei Corporation (Japan.) It is a cardiovascular and cerebrovascular drug which improves symptoms of ischemic cerebrovascular disease such as cerebral vasospasm following subarachnoid hemorrhage. It has significant neuroprotective and therapeutic effects for ischemic cerebrovascular disease, and is suited for clinical use, particularly at the grassroots level to reduce mortality and improve quality of life.

Mechanisms of Action

Fasudil Hydrochloride is an isoquinoline sulfonamide derivative which can relax separated cerebral blood vessels, inhibit the shrinkage of separated blood vessels caused by calcium influx, inhibit different mechanisms of brain blood vessel contraction from contractile agents, and inhibit intracellular calcium ion activity without reducing calcium ion concentration. Fasudil Hydrochloride is an RHO kinase inhibitor which dilates vessels, reduces tension of endothelial cells, and improves microcirculation of brain tissue without producing or exacerbating diversion of blood to the brain, by increasing activity of myosin light chain phosphatase. At the same time, it can protect nerves against apoptosis and promote their regeneration. Fasudil Hydrochloride promotes recovery of neural function and reduces clinical symptoms.

Adverse reactions

Adverse reactions after use can include intracranial hemorrhage, gastrointestinal bleeding, pulmonary hemorrhage, nasal bleeding, subcutaneous bleeding, and loss of consciousness, etc., as well as abnormal liver function. Low blood pressure, anemia, leukopenia, renal dysfunction, polyuria, rashes, and fever, etc. occur occasionally.

Warnings and Precautions

Patients with intracranial hemorrhage or possibility thereof, or low blood pressure, should not use. Patients with diabetes mellitus, cerebral arterial sclerosis, severe disturbance of consciousness, subarachnoid hemorrhages with cerebrovascular disorders, and liver or kidney dysfunction, or those over 70 years old, pregnant, or children should use with caution. Breastfeeding women should stop while using the drug. Fasudil Hydrochloride can only be administered via intravenous drip.

Description

Fasudil hydrochloride, a novel calcium antagonistic vasodilator, was marketed for the treatment of cerebral vasospasm following subarachnoid hemorrhage (SAH). Fasudil is also a potent inhibitor of myosin light chain kinase and protein kinase C. In contrast to other calcium channel blockers, which regulate the influx of calcium ions through the cell membrane but not involved in the intracellular regulatory mechanism of the calcium, fasudil was suggested to have an intracellular mode of action in relaxing vascular smooth muscle. In patients with neurological deficits due to vasospasm, fasudil decreased the occurrence of angiographic severe and symptomatic vasospasm and cerebral infarction without decreasing systemic blood pressure. Fasudil is reportedly in clinical trials for acute ischemic stroke, sequelae of cerebral vascular diseases and angina pectoris.

Originator

Asahi Chemical (Japan)

Uses

Fasudil monohydrochloride is used in the prevention and treating cardiovascular and cerebrovascular diseases. It is also used in the inhibition of proliferation of vascular smooth muscle cells. It serves as a selective Rho-associated protein kinase (ROCK) inhibitor. Further, it protects against methyl mercury-induced axonal degeneration.

Uses

vasodilator, potent Rho-kinase inhibitor

Definition

ChEBI: Fasudil hydrochloride is a hydrochloride obtained by reaction of fasudil with one equivalent of hydrochloric acid. It has a role as an antihypertensive agent, a calcium channel blocker, an EC 2.7.11.1 (non-specific serine/threonine protein kinase) inhibitor, a neuroprotective agent, a nootropic agent and a vasodilator agent. It contains a fasudil(1+).

brand name

Eril

storage

Room temperature

References

1) Davies et al. (2000), Specificity and mechanism of action of some commonly used protein kinase inhibitors; Biochem. J., 351 95 2) Anwar et al. (2013), Signal transduction and modulating pathways in tryptamine-evoked vasopressor responses of the rat isolated perfused mesenteric bed; Vascul. Pharmacol., 58 140 3) Jiang et al. (2012), Fasudil, a rho-kinase inhibitor, attenuates bleomycin-induced pulmonary fibrosis in mice; Int. J. Mol. Sci., 13 8293

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