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High purity Fasudil?Hydrochloride CAS:105628-07-7
Cas No: 105628-07-7
USD $ 100.0-500.0 / Gram 1 Gram 99999 Gram/Year Hangzhou Dingyan Chem Co., Ltd Contact Supplier
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USD $ 0.1-0.1 / Gram 1 Gram 100 Metric Ton/Year Xi'an Xszo Chem Co., Ltd. Contact Supplier

105628-07-7 Usage

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

Brand name

Eril

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
InChI:InChI=1/C14H17N3O2S.ClH/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;1H

105628-07-7 Well-known Company Product Price

Brand (Code)Product description CAS number Packaging Price Detail
TCI America (F0839)  Fasudil Hydrochloride  >98.0%(HPLC) 105628-07-7 100mg 1,490.00CNY Detail

105628-07-7SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name Fasudil Hydrochloride

1.2 Other means of identification

Product number -
Other names 5-((1,4-Diazepan-1-yl)sulfonyl)isoquinoline hydrochloride

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:105628-07-7 SDS

105628-07-7Synthetic route

1,4-Diazacycloheptane
505-66-8

1,4-Diazacycloheptane

isoquinoline-5-sulfonyl chloride hydrochloride
105627-79-0

isoquinoline-5-sulfonyl chloride hydrochloride

fasudil hydrochloride
105628-07-7

fasudil hydrochloride

Conditions
ConditionsYield
In dichloromethane at 0 - 50℃; for 2h; Temperature;89%
1,4-Diazacycloheptane
505-66-8

1,4-Diazacycloheptane

isoquinoline-5-sulfonic acid
27655-40-9

isoquinoline-5-sulfonic acid

1-chloro-3,5-dimethoxybenzene
7051-16-3

1-chloro-3,5-dimethoxybenzene

fasudil hydrochloride
105628-07-7

fasudil hydrochloride

Conditions
ConditionsYield
Stage #1: isoquinoline-5-sulfonic acid; 1-chloro-3,5-dimethoxybenzene With 4-methyl-morpholine In chloroform at 10℃; for 4h; Reflux;
Stage #2: 1,4-Diazacycloheptane In chloroform at 30℃; for 3.5h; Reagent/catalyst; Solvent; Reflux; Further stages;
84.4%
fasudil
103745-39-7

fasudil

fasudil hydrochloride
105628-07-7

fasudil hydrochloride

Conditions
ConditionsYield
With hydrogenchloride; pyrographite In methanol; water at 30℃; pH=4.5 - 5;34.9%
1,4-Diazacycloheptane
505-66-8

1,4-Diazacycloheptane

5-isoquinolinesulfonyl chloride
84468-15-5

5-isoquinolinesulfonyl chloride

fasudil hydrochloride
105628-07-7

fasudil hydrochloride

Conditions
ConditionsYield
With water; sodium hydrogencarbonate 2.) CH2Cl2, RT, 1 h; Yield given. Multistep reaction;
isoquinoline-5-sulfonic acid
27655-40-9

isoquinoline-5-sulfonic acid

fasudil hydrochloride
105628-07-7

fasudil hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: thionyl chloride / N,N-dimethyl-formamide / 2 h / Reflux; Large scale
2: ammonia / dichloromethane / 10 °C / Large scale
3: pyrographite; hydrogenchloride / methanol; water / 30 °C / pH 4.5 - 5
View Scheme
fasudil dihydrogen phosphate

fasudil dihydrogen phosphate

fasudil hydrochloride
105628-07-7

fasudil hydrochloride

Conditions
ConditionsYield
Stage #1: fasudil dihydrogen phosphate With sodium hydroxide In water pH=10 - 10.5;
Stage #2: With hydrogenchloride In methanol; water at 50 - 60℃; pH=5 - 5.1;
16.3 g
1,3-dioxoisoindolin-2-yl N2,N6-bis(tert-butoxycarbonyl)lysinate

1,3-dioxoisoindolin-2-yl N2,N6-bis(tert-butoxycarbonyl)lysinate

fasudil hydrochloride
105628-07-7

fasudil hydrochloride

C30H46N4O6S

C30H46N4O6S

Conditions
ConditionsYield
With 1,1'-binaphthyl-2,2'-diyl hydrogenphosphate; [4,4’-bis(1,1-dimethylethyl)-2,2’-bipyridine-N1,N1‘]bis [3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-N]phenyl-C]iridium(III) hexafluorophosphate In N,N-dimethyl acetamide; water at 20℃; for 5h; Schlenk technique; Irradiation; Inert atmosphere;91%
4-nitrophenyl 2-(2-(pyridin-2-yl)disulfanyl)ethyl carbonate
874302-76-8

4-nitrophenyl 2-(2-(pyridin-2-yl)disulfanyl)ethyl carbonate

fasudil hydrochloride
105628-07-7

fasudil hydrochloride

2-(pyridin-2-yldisulfanyl)ethyl 4-(isoquinolin-5-ylsulfonyl)-1,4-diazepane-1-carboxylate

2-(pyridin-2-yldisulfanyl)ethyl 4-(isoquinolin-5-ylsulfonyl)-1,4-diazepane-1-carboxylate

Conditions
ConditionsYield
With triethylamine In dichloromethane90%
4-cyclohexyl-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylic acid diethyl ester
1539-59-9

4-cyclohexyl-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylic acid diethyl ester

fasudil hydrochloride
105628-07-7

fasudil hydrochloride

5‐((1,4‐diazepan‐1‐yl)sulfonyl)‐1‐cyclohexylisoquinoline

5‐((1,4‐diazepan‐1‐yl)sulfonyl)‐1‐cyclohexylisoquinoline

Conditions
ConditionsYield
With sodium persulfate; trifluoroacetic acid In water; acetonitrile at 20℃; for 18h; Inert atmosphere;84%
fasudil hydrochloride
105628-07-7

fasudil hydrochloride

C14H17N3O3S

C14H17N3O3S

Conditions
ConditionsYield
Stage #1: fasudil hydrochloride With sodium hydrogencarbonate for 0.5h; pH=5 - 6;
Stage #2: With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 30℃; for 1h;
82.17%
O-(4-nitrophenyl)-O’-propargylcarbonate
228111-40-8

O-(4-nitrophenyl)-O’-propargylcarbonate

fasudil hydrochloride
105628-07-7

fasudil hydrochloride

prop-2-yn-1-yl 4-(isoquinolin-5-ylsulfonyl)-1,4-diazepane-1-carboxylate

prop-2-yn-1-yl 4-(isoquinolin-5-ylsulfonyl)-1,4-diazepane-1-carboxylate

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃;73.5%
diethyl 4-((benzyloxy)methyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate

diethyl 4-((benzyloxy)methyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate

fasudil hydrochloride
105628-07-7

fasudil hydrochloride

5-((1,4-diazepan-1-yl)sulfonyl)-1-((benzyloxy)methyl)isoquinoline

5-((1,4-diazepan-1-yl)sulfonyl)-1-((benzyloxy)methyl)isoquinoline

Conditions
ConditionsYield
With sodium persulfate; trifluoroacetic acid In water; acetonitrile at 20℃; for 18h; Inert atmosphere;51%
2-oxo-2-(piperidin-1-yl)acetic acid
4706-33-6

2-oxo-2-(piperidin-1-yl)acetic acid

fasudil hydrochloride
105628-07-7

fasudil hydrochloride

(5-((1,4-diazepan-1-yl)sulfonyl)isoquinoline-1-yl)(piperidin-1-yl)methanone

(5-((1,4-diazepan-1-yl)sulfonyl)isoquinoline-1-yl)(piperidin-1-yl)methanone

Conditions
ConditionsYield
With ammonium peroxydisulfate In water; dimethyl sulfoxide at 50℃; for 16h;50%
fasudil hydrochloride
105628-07-7

fasudil hydrochloride

Cyclohexanecarboxylic acid
98-89-5

Cyclohexanecarboxylic acid

5‐((1,4‐diazepan‐1‐yl)sulfonyl)‐1‐cyclohexylisoquinoline

5‐((1,4‐diazepan‐1‐yl)sulfonyl)‐1‐cyclohexylisoquinoline

Conditions
ConditionsYield
With dipotassium peroxodisulfate In water; dimethyl sulfoxide at 40℃; for 16h; Minisci Aromatic Substitution; Inert atmosphere; Schlenk technique; Sealed tube;44%
fasudil hydrochloride
105628-07-7

fasudil hydrochloride

6H-1-(5-isoquinolinesulfonyl)-4-(β-hydroxyethyl)-1,4-diazepane

6H-1-(5-isoquinolinesulfonyl)-4-(β-hydroxyethyl)-1,4-diazepane

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium hydrogencarbonate / water / 0.5 h / pH 5 - 6
2: triethylamine / dichloromethane / 30 h / 20 °C
View Scheme
fasudil hydrochloride
105628-07-7

fasudil hydrochloride

fasudil
103745-39-7

fasudil

Conditions
ConditionsYield
With sodium hydrogencarbonate In water for 0.5h; pH=5 - 6;
fasudil hydrochloride
105628-07-7

fasudil hydrochloride

4-(isoquinoline-5-sulfonyl)-[1,4]diazepane-1-carboxylic acid tert-butyl ester
612483-90-6

4-(isoquinoline-5-sulfonyl)-[1,4]diazepane-1-carboxylic acid tert-butyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium hydrogencarbonate / water / 0.5 h / pH 5 - 6
2: triethylamine / dichloromethane / 2 h / 0 - 5 °C
View Scheme
fasudil hydrochloride
105628-07-7

fasudil hydrochloride

fasudil dihydrogen phosphate

fasudil dihydrogen phosphate

Conditions
ConditionsYield
With potassium dihydrogenphosphate In methanol; water at 25 - 30℃; Reagent/catalyst; Temperature;30.1 g
fasudil hydrochloride
105628-07-7

fasudil hydrochloride

C21H29N3O5S

C21H29N3O5S

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: triethylamine / dichloromethane / 2 h / 0 °C
2: [4,4’-bis(1,1-dimethylethyl)-2,2’-bipyridine-N1,N1‘]bis [3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-N]phenyl-C]iridium(III) hexafluorophosphate; trifluoroacetic acid / N,N-dimethyl acetamide / 24 h / 20 °C / Inert atmosphere; Irradiation
View Scheme
fasudil hydrochloride
105628-07-7

fasudil hydrochloride

5-((4-acetyl-1,4-diazepan-1-yl)sulfonyl)isoquinoline-1-carbaldehyde

5-((4-acetyl-1,4-diazepan-1-yl)sulfonyl)isoquinoline-1-carbaldehyde

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: triethylamine / dichloromethane / 2 h / 0 °C
2: [4,4’-bis(1,1-dimethylethyl)-2,2’-bipyridine-N1,N1‘]bis [3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-N]phenyl-C]iridium(III) hexafluorophosphate; trifluoroacetic acid / N,N-dimethyl acetamide / 24 h / 20 °C / Inert atmosphere; Irradiation
3: hydrogenchloride / N,N-dimethyl acetamide; 1,4-dioxane / 6 h
View Scheme
acetic anhydride
108-24-7

acetic anhydride

fasudil hydrochloride
105628-07-7

fasudil hydrochloride

1-(4-((1-cyclohexylisoquinolin-5-yl)sulfonyl)-1,4-diazepan-1-yl)ethan-1-one
1422972-00-6

1-(4-((1-cyclohexylisoquinolin-5-yl)sulfonyl)-1,4-diazepan-1-yl)ethan-1-one

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0℃; for 2h;897 mg
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