1-(5-ISOQUINOLINESULFONYL)-2-METHYLPIPERAZINE

Details

Stereochemistry	RACEMIC
Molecular Formula	C14H17N3O2S
Molecular Weight	291.369
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure of 1-(5-ISOQUINOLINESULFONYL)-2-METHYLPIPERAZINE

SMILES

CC1CNCCN1S(=O)(=O)C2=CC=CC3=CN=CC=C23

InChI

InChIKey=BDVFVCGFMNCYPV-UHFFFAOYSA-N

InChI=1S/C14H17N3O2S/c1-11-9-16-7-8-17(11)20(18,19)14-4-2-3-12-10-15-6-5-13(12)14/h2-6,10-11,16H,7-9H2,1H3

HIDE SMILES / InChI

Description

1-(5-isoquinolinylsulfonyl)-2-methylpiperazine (H-7) is an inhibitor of cAMP-dependent, cGMP-dependent, and Ca2+-phospholipid-dependent (protein kinase C) protein kinases at roughly equal concentrations. It is widely used to study protein kinase signaling both in vitro and in vivo.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Protein kinase C (PKC) 44	Inhibitor 8,504	6.0 µM [Ki]
cAMP-dependent protein kinase (PKA) 18	Inhibitor 8,504	3.0 µM [Ki]
cGMP-dependent protein kinase activity 2	Inhibitor 8,504	5.8 µM [Ki]

Conditions

Condition	Modality	Highest Phase	Product
Pain 619	Primary	Preclinical	Unknown
Opioid dependence 21	Primary	Preclinical	Unknown
Pulmonary edema 25	Primary	Preclinical	Unknown

PubMed

Show entries

Title	Date	PubMed
MAP kinase-independent induction of proto-oncogene c-fos mRNA by hemin in human cells.	1999 Jun 24	10381381
A novel drug delivery system as prophylaxis for cerebral vasospasm.	2001	11563290
Effect of Fasudil HCl, a protein kinase inhibitor, on cerebral vasospasm.	2001	11563286
Direct autocrine inhibition and cAMP-dependent potentiation of single L-type Ca2+ channels in bovine chromaffin cells.	2001 Apr 1	11283226
H-7 and fetal calf serum (FCS) act synergistically to increase apoptosis in the KB line of human oral carcinoma cells.	2001 Aug	11521953

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Patents

Sample Use Guides

In Vivo Use Guide

rats: 1 or 10 nmol/microl/h 1-(5-isoquinolinesulfonyl)-2-methylpiperazine dihydrochloride (H-7) intracerebroventricularly (i.c.v.) via osmotic minipumps. mice: mechanical allodynia was inhibited by intrathecal injection of 5 or 10 pmol 1-(5-isoquinolinesulfonyl)-2-methylpiperazine (H-7)

Route of Administration: Other

In Vitro Use Guide

1-(5-isoquinolinesulfonyl)-2-methylpiperazine dihydrochloride (H-7) inhibited the PMA-induced promiscuous lympholysis with IC50 value of 4 uM. H-7 (20-100 microM) induced apoptosis in SH-SY5Y cells characterized by DNA fragmentation and chromatin condensation.

Show entries

Name

Type

Language

1-(5-ISOQUINOLINESULFONYL)-2-METHYLPIPERAZINE

Systematic Name

English

(±)-1-(5-ISOQUINOLINESULFONYL)-2-METHYLPIPERAZINE

Preferred Name

English

PIPERAZINE, 1-(5-ISOQUINOLINYLSULFONYL)-2-METHYL-

Systematic Name

English

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Code System

Code

Type

Description

EPA CompTox

DTXSID401004756

PRIMARY

DRUG BANK

DB07996

PRIMARY

FDA UNII

487H9Q0F9N

PRIMARY

CAS

84477-87-2

PRIMARY

CHEBI

43385

PRIMARY

Showing 1 to 5 of 6 entries

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SUBSTANCE RECORD


					487H9Q0F9N

1-(5-ISOQUINOLINESULFONYL)-2-METHYLPIPERAZINE

SMILES

InChI

Description<div class="info-popup-container"><div><span class="pop-sub-key ">Sources:&nbsp;</span><span class="pop-sub-val"><span class="ext-link"><a target="_self" href="https://www.ncbi.nlm.nih.gov/pubmed/6238627">https://www.ncbi.nlm.nih.gov/pubmed/6238627</a></span></span></div></div>

CNS Activity

Originator

Approval Year

Targets

Conditions

PubMed

Patents

Sample Use Guides

Description