FASUDIL HYDROCHLORIDE HEMIHYDRATE

Possibly Marketed Outside US

Details

Stereochemistry	ACHIRAL
Molecular Formula	2C14H17N3O2S.2ClH.H2O
Molecular Weight	673.675
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure of FASUDIL HYDROCHLORIDE HEMIHYDRATE

SMILES

O.Cl.Cl.O=S(=O)(N1CCCNCC1)C2=CC=CC3=CN=CC=C23.O=S(=O)(N4CCCNCC4)C5=CC=CC6=CN=CC=C56

InChI

InChIKey=AACOJGPCMIDLEY-UHFFFAOYSA-N

InChI=1S/2C14H17N3O2S.2ClH.H2O/c2*18-20(19,17-9-2-6-15-8-10-17)14-4-1-3-12-11-16-7-5-13(12)14;;;/h2*1,3-5,7,11,15H,2,6,8-10H2;2*1H;1H2

HIDE SMILES / InChI

Molecular Formula	ClH
Molecular Weight	36.461
Charge	0
Count	MOL RATIO 2 MOL RATIO (average)

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	C14H17N3O2S
Molecular Weight	291.369
Charge	0
Count	MOL RATIO 2 MOL RATIO (average)

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	H2O
Molecular Weight	18.0153
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description

Fasudil is a potent Rho kinase inhibitor, which was developed by Asahi Kasei. The drug is used in Asia for the prevention of cerebral vasospasm in patients with subarachnoid hemorrhage.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Rho-associated protein kinase 7	Inhibitor 8,504		0.4 µM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Cerebral vasospasm 9	Preventing		Approved 8,583	ERIL

C_max

Value	Dose	Analyte	Population
100.4 ng/mL	0.2 mg/kg bw single, intravenous	FASUDIL plasma	Homo sapiens
215.7 ng/mL	0.4 mg/kg bw single, intravenous	FASUDIL plasma	Homo sapiens
71.7 ng/mL	0.2 mg/kg bw 2 times / day multiple, intravenous	FASUDIL plasma	Homo sapiens
74.8 ng/mL	0.2 mg/kg bw 2 times / day multiple, intravenous	FASUDIL plasma	Homo sapiens
125 ng/mL	30 mg 3 times / day multiple, intravenous	FASUDIL plasma	Homo sapiens
166.9 ng/mL	30 mg 3 times / day multiple, intravenous	FASUDIL plasma	Homo sapiens
126.9 ng/mL	30 mg 3 times / day multiple, intravenous	FASUDIL plasma	Homo sapiens

AUC

Value	Dose	Analyte	Population
46.1 ng × h/mL	0.2 mg/kg bw single, intravenous	FASUDIL plasma	Homo sapiens
94.8 ng × h/mL	0.4 mg/kg bw single, intravenous	FASUDIL plasma	Homo sapiens
27.2 ng × h/mL	0.2 mg/kg bw 2 times / day multiple, intravenous	FASUDIL plasma	Homo sapiens
31.4 ng × h/mL	0.2 mg/kg bw 2 times / day multiple, intravenous	FASUDIL plasma	Homo sapiens
86.9 ng × h/mL	30 mg 3 times / day multiple, intravenous	FASUDIL plasma	Homo sapiens
120 ng × h/mL	30 mg 3 times / day multiple, intravenous	FASUDIL plasma	Homo sapiens
89 ng × h/mL	30 mg 3 times / day multiple, intravenous	FASUDIL plasma	Homo sapiens

T_1/2

Value	Dose	Analyte	Population
14.2 min	0.2 mg/kg bw single, intravenous	FASUDIL plasma	Homo sapiens
15.6 min	0.4 mg/kg bw single, intravenous	FASUDIL plasma	Homo sapiens
10.3 min	0.2 mg/kg bw 2 times / day multiple, intravenous	FASUDIL plasma	Homo sapiens
10.6 min	0.2 mg/kg bw 2 times / day multiple, intravenous	FASUDIL plasma	Homo sapiens
24.4 min	30 mg 3 times / day multiple, intravenous	FASUDIL plasma	Homo sapiens
21.6 min	30 mg 3 times / day multiple, intravenous	FASUDIL plasma	Homo sapiens
28.6 min	30 mg 3 times / day multiple, intravenous	FASUDIL plasma	Homo sapiens

F_unbound

Value	Dose	Co-administered	Analyte	Population
63.8%	0.2 mg/kg bw single, intravenous		FASUDIL plasma	Homo sapiens

Doses

Show entries

Dose	Population	Adverse events
30 mg 3 times / day multiple, intravenous Studied dose	unhealthy, ADULT	Other AEs: AST increased, ALT increased...
40 mg 3 times / day multiple, intravenous Studied dose	unhealthy, ADULT
60 mg 1 times / day multiple, intravenous Studied dose	unhealthy, ADULT

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AEs

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AE	Significance	Dose	Population
ALP increased	2%	30 mg 3 times / day multiple, intravenous Studied dose	unhealthy, ADULT
AST increased	2%	30 mg 3 times / day multiple, intravenous Studied dose	unhealthy, ADULT
Gamma-glutamyltransferase increased	2%	30 mg 3 times / day multiple, intravenous Studied dose	unhealthy, ADULT
ALT increased	4%	30 mg 3 times / day multiple, intravenous Studied dose	unhealthy, ADULT

Showing 1 to 4 of 4 entries

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PubMed

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Title	Date	PubMed
Effect of Fasudil HCl, a protein kinase inhibitor, on cerebral vasospasm.	2001	11563286
Efficacy of intrathecal liposomal fasudil for experimental cerebral vasospasm after subarachnoid hemorrhage.	2001 Apr	11322450
Pharmacological profile of hydroxy fasudil as a selective rho kinase inhibitor on ischemic brain damage.	2001 Aug 10	11531167
Antianginal effects of hydroxyfasudil, a Rho-kinase inhibitor, in a canine model of effort angina.	2001 Dec	11739249
Rho-associated kinase phosphorylates MARCKS in human neuronal cells.	2001 Jan 26	11162562

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Patents

Sample Use Guides

In Vivo Use Guide

The recommended dosage is 30 mg fasudil hydrochloride should be diluted in 50-100 mL solution and administered by intravenous infusion over 30 minutes 2-3 times daily.

Route of Administration: Intravenous

In Vitro Use Guide

The rat aortic rings were contracted by KCl; when the contraction reached a plateau, fasudil was added at concentrations from 10(-9) to 10(-5) M. The relaxation IC50 was 0.74 uM. When rabbit aortic rings were used, IC50 values were 37,15 uM and 27,54 uM for KCl and Methoxamine-induced contraction, respectively.

Substance Class	Chemical
Record UNII	LI4L0R5Y7T
Record Status	`Validated (UNII)`
Record Version

Show entries

Name

Type

Language

FASUDIL HYDROCHLORIDE HYDRATE

Preferred Name

English

FASUDIL HYDROCHLORIDE HEMIHYDRATE

Common Name

English

1H-1,4-DIAZEPINE, HEXAHYDRO-1-(5-ISOQUINOLINYLSULFONYL)-, MONOHYDROCHLORIDE, HYDRATE (2:1)

Common Name

English

5-(HEXAHYDRO-1H-1,4-DIAZEPINE-1-YLSULFONYL)ISOQUINOLINE HYDROCHLORIDE HEMIHYDRATE

Common Name

English

ISOQUINOLINE, 5-((HEXAHYDRO-1H-1,4-DIAZEPIN-1-YL)SULFONYL)-, HYDROCHLORIDE, HYDRATE (2:2:1)

Systematic Name

English

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Code System

Code

Type

Description

CAS

186694-02-0

PRIMARY

FDA UNII

LI4L0R5Y7T

PRIMARY

PUBCHEM

23724856

PRIMARY

EPA CompTox

DTXSID80171929

PRIMARY

SMS_ID

300000017637

PRIMARY

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ANHYDROUS->SOLVATE


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FASUDIL

PARENT -> SALT/SOLVATE

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FASUDIL

ACTIVE MOIETY

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SMILES

InChI

Originator

Approval Year

Targets

Conditions

Cmax

AUC

T1/2

Funbound

Doses

AEs

PubMed

Patents

Sample Use Guides

C_max

T_1/2

F_unbound