Fasudil

HCID 3547CAS 103745-39-7
Substructure searchFind similar structures

Basic information

Standard SMILES
O=S(=O)(c1cccc2cnccc12)N1CCCNCC1
InChIKey
NGOGFTYYXHNFQH-UHFFFAOYSA-N
Molecular formula
C14H17N3O2S
Average molar mass
291.37 g/mol
Monoisotopic mass
291.10414778

Overview

Fasudil is an isoquinoline substituted by a (1,4-diazepan-1-yl)sulfonyl group at position 5. It is a Rho-kinase inhibitor and its hydrochloride hydrate form is approved for the treatment of cerebral vasospasm and cerebral ischemia. It has a role as a geroprotector, a vasodilator agent, an antihypertensive agent, a calcium channel blocker, an EC 2.7.11.1 (non-specific serine/threonine protein kinase) inhibitor, a neuroprotective agent and a nootropic agent. It is a member of isoquinolines and a N-sulfonyldiazepane. It is a conjugate base of a fasudil(1+).

Names & identifiers

Preferred name
Fasudil
IUPAC
5-(1,4-diazepan-1-ylsulfonyl)isoquinoline
English name
FASUDIL
Molecular formula
C14H17N3O2S
Molecular weight
291.37

Names & synonyms

Fasudil103745-39-7ha-1077HA1077AT-877Fasudilum1H-1,4-Diazepine, hexahydro-1-(5-isoquinolinylsulfonyl)-HA 1077AT 8771-(5-Isoquinolinesulfonyl)homopiperazineQ0CH43PGXSHexahydro-1-(5-isoquinolinylsulfonyl)-1H-1,4-diazepine
Show more names
Fasudil HCIHA-1077：ErilFASUDIL USP/EP/BPFasudil HydrchlorideFasudil hydrochloridFasudilum [inn-latin]H-1077 dihydrochloride
NSC-759827ZK-258594AT8775-[(Hexahydro-1H-1,4-diazepin-1-yl)sulfonyl]isoquinolineDTXSID4048569CHEBI:438715-((HEXAHYDRO-1H-1,4-DIAZEPIN-1-YL)SULFONYL)ISOQUINOLINERefChem:597170

Database identifiers

CAS
103745-39-7
PubChem CID
3547
DTXSID
DTXSID4048569
ChEMBL
CHEMBL38380
ChEBI
CHEBI:43871
UNII
Q0CH43PGXS
EC Number
816-154-4
Nikkaji
J227.600C

Properties

Computed structural properties

XLogP
1
Topological polar surface area
70.7 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
5
Rotatable bonds
2
Heavy atoms
20

Experimental & physicochemical properties

DrugsPharmaceuticals -> Listed in ZINC15

Physicochemical properties

Boiling point
506.2 · 506.2±60.0 °C(Predicted)
Density
1.289 · 1.289±0.06 g/cm3(Predicted)
storage temp.
Store at RT
solubility
2 O: · H2O: >200 mg/mL
form
solid
pka
9.73 · 9.73±0.20(Predicted)

Safety & regulation

GHS classification

GHS Classification · 4 items

Warning

H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.

Hazard information

Hazard Classes and CategoriesSkin Irrit. 2 (100%)

Safety data

wgk
3
rtecs
HM4031166
hs_code
29334900
Toxicity
mouse,LD50,unreported,73500ug/kg (73.5mg/kg),United States Patent Document. Vol. #4678783,
Signal word
Warning
Symbol(GHS)
GHS07

Chemistry & industry

Pharmacology

ATC Code · 2 items

C - Cardiovascular system

QC - Cardiovascular system

MeSH Pharmacological Classification · 3 items

A class of drugs that act by selective inhibition of calcium influx through cellular membranes.

Drugs used to cause dilation of the blood vessels.

Agents that inhibit PROTEIN KINASES.

Applications · 4 items

Usesvasodilator (cerebral), Ca antagonist

UsesA potent calcium antagonist vasodilator which is considered to act by employing different mechanisms from the usual calcium channel blockers since it inhibits (1) calcium ionophore A23187 induced co ntraction in arterial strips and (2) phenylephrine induced contraction in calcium free media suggesting that its site of action is in the intracellular space. Also reported to potently inhibit Rho- associated Kinase (ROCK IC50= 10.7 uM).

UsesFasudil is a protein kinase A inhibitor and may be used in medicinal combinations for hepatitis treatment.

General DescriptionA cell-permeable, reversible, and ATP-competitive Ca2+ antagonist with anti-vasospastic properties. Inhibits protein kinase A (Ki = 1.6 μM), protein kinase G (Ki = 1.6 μM), and myosin light chain kinase (Ki = 3.6 μM). Also reported to potently inhibit Rho-associated kinase (ROCK; IC50 = 10.7 μM). Prevents apoptosis and enhances the survival and cloning efficiency of dissociated hES cells without affecting their pluripotency.

Upstream & downstream products

Upstream raw materials

Downstream products

Suppliers50 total

上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
湖北万得化工有限公司15377098680 15377098680 · [email protected]
上海优宁维生物科技股份有限公司15921930842 15921930842 · [email protected]
湖北科乐精细化工有限公司027-59101668 19945030958 · [email protected]
LGM Pharma1-(800)-881-8210 · [email protected]
Additional notes · 1 item

DefinitionChEBI: Fasudil is an isoquinoline substituted by a (1,4-diazepan-1-yl)sulfonyl group at position 5. It is a Rho-kinase inhibitor and its hydrochloride hydrate form is approved for the treatment of cerebral vasospasm and cerebral ischemia. It has a role as a geroprotector, an EC 2.7.11.1 (non-specific serine/threonine protein kinase) inhibitor, a vasodilator agent, a nootropic agent, a neuroprotective agent, an antihypertensive agent and a calcium channel blocker. It is a N-sulfonyldiazepane and a member of isoquinolines. It is a conjugate base of a fasudil(1+).

Related reactions

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