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105628-07-7

Basic Information
CAS No.: 105628-07-7
Name: Fasudil hydrochloride
Molecular Structure:
Molecular Structure of 105628-07-7 (Fasudil hydrochloride)
Formula: C14H18ClN3O2S
Molecular Weight: 327.83
Synonyms: Isoquinoline,5-[(hexahydro-1H-1,4-diazepin-1-yl)sulfonyl]-, hydrochloride (1:1);1H-1,4-Diazepine,hexahydro-1-(5-isoquinolinylsulfonyl)-, monohydrochloride (9CI);1-(5-Isoquinolinesulfonyl)homopiperazine hydrochloride;Fasudilhydrochloride;
EINECS: 805-833-0
Density:
Melting Point: 220.5°; mp 219.3° (Shirotani)
Boiling Point: 506.2 °C at 760 mmHg
Flash Point: 259.9 °C
Solubility: Water solubility: >200 mg/mL
Appearance: white solid
Hazard Symbols:
Risk Codes: 22
Safety: 36-60
Transport Information:
PSA: 70.68000
LogP: 4.17030
Synthetic route
505-66-8

1,4-Diazacycloheptane

105627-79-0

isoquinoline-5-sulfonyl chloride hydrochloride

105628-07-7

fasudil hydrochloride

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

1,4-Diazacycloheptane

27655-40-9

isoquinoline-5-sulfonic acid

7051-16-3

1-chloro-3,5-dimethoxybenzene

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%
105628-07-7

fasudil hydrochloride

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

1,4-Diazacycloheptane

84468-15-5

5-isoquinolinesulfonyl chloride

105628-07-7

fasudil hydrochloride

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

isoquinoline-5-sulfonic acid

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

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

105628-07-7

fasudil hydrochloride

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%
874302-76-8

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

105628-07-7

fasudil hydrochloride

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

Conditions
ConditionsYield
With triethylamine In dichloromethane90%
1539-59-9

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

105628-07-7

fasudil hydrochloride

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%
105628-07-7

fasudil hydrochloride

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%
228111-40-8

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

105628-07-7

fasudil hydrochloride

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

105628-07-7

fasudil hydrochloride

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%
4706-33-6

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

105628-07-7

fasudil hydrochloride

(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%
105628-07-7

fasudil hydrochloride

98-89-5

Cyclohexanecarboxylic acid

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%
105628-07-7

fasudil hydrochloride

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
105628-07-7

fasudil hydrochloride

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

fasudil hydrochloride

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
105628-07-7

fasudil hydrochloride

fasudil dihydrogen phosphate

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

fasudil hydrochloride

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
105628-07-7

fasudil hydrochloride

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
108-24-7

acetic anhydride

105628-07-7

fasudil hydrochloride

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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Specification

The CAS registry number of Fasudil hydrochloride is 105628-07-7. The IUPAC name is 5-(1,4-diazepan-1-ylsulfonyl)isoquinoline hydrochloride. In addition, the molecular formula is C14H18ClN3O2S and the molecular weight is 327.83. It is also called 1-(5-isoquinolinesulfonyl)homopiperazine hydrochloride. What's more, it should be stored in a cool and dry place.

Physical properties about Fasudil hydrochloride are: (1)ACD/LogP: 1.19; (2)# of Rule of 5 Violations: 0; (3)#H bond acceptors: 5; (4)#H bond donors: 1; (5)#Freely Rotating Bonds: 2; (6)Polar Surface Area: 61.89 Å2; (7)Flash Point: 259.9 °C; (8)Enthalpy of Vaporization: 77.6 kJ/mol; (9)Boiling Point: 506.2 °C at 760 mmHg; (10)Vapour Pressure: 2.27E-10 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES: O=S(=O)(c2c1ccncc1ccc2)N3CCCNCC3.Cl
(2)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
(3)InChIKey: LFVPBERIVUNMGV-UHFFFAOYAY

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
monkey LD50 intravenous 20mg/kg (20mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 26, Pg. 740, 1995.
mouse LD50 intravenous 67600ug/kg (67.6mg/kg) SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: STRAUB TAIL
Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 20(Suppl,
mouse LD50 oral 274mg/kg (274mg/kg) SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE

BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 20(Suppl,
mouse LD50 subcutaneous 124mg/kg (124mg/kg) SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)
Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 20(Suppl,
rat LD50 intravenous 59900ug/kg (59.9mg/kg) SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF SALIVARY GLANDS
Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 20(Suppl,
rat LD50 oral 335mg/kg (335mg/kg) SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE

BEHAVIORAL: TREMOR

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 20(Suppl,
rat LD50 subcutaneous 123mg/kg (123mg/kg) SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE

BEHAVIORAL: TREMOR

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 20(Suppl,

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