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

Structure Search

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

Molecular Formula	C14H17N3O2S
Molecular Weight	291.369
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/6238627

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 Target ID: CHEMBL2093867 Sources: https://www.ncbi.nlm.nih.gov/pubmed/6238627 \| https://www.ncbi.nlm.nih.gov/pubmed/3390230	Inhibitor 8504	6.0 µM [Ki]
cAMP-dependent protein kinase (PKA) 18 Target ID: CHEMBL2094138 Sources: https://www.ncbi.nlm.nih.gov/pubmed/6238627	Inhibitor 8504	3.0 µM [Ki]
cGMP-dependent protein kinase activity 2 Target ID: GO:0004692 Sources: https://www.ncbi.nlm.nih.gov/pubmed/6238627	Inhibitor 8504	5.8 µM [Ki]

Conditions

Condition	Modality	Highest Phase	Product
Pain 619 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17473449	Primary	Preclinical	Unknown Approved Use Unknown
Opioid dependence 21 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9570513 https://www.ncbi.nlm.nih.gov/pubmed/8549612 https://www.ncbi.nlm.nih.gov/pubmed/10922515	Primary	Preclinical	Unknown Approved Use Unknown
Pulmonary edema 25 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2705544	Primary	Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Involvement of rho-kinase in agonists-induced contractions of arteriosclerotic human arteries.	2002-02-01	11834523
Nucleotide-evoked relaxation of rat vas deferens: possible mechanisms.	2002-02-01	11834257
Pharmacological characterization of the P2X(7) receptor on human macrophages using the patch-clamp technique.	2002-02	11819036
Estrogen inhibition of PTH-stimulated osteoclast formation and attachment in vitro: involvement of both PKA and PKC.	2002-02	11796519
CaMKII is activated and translocated to the secretory apical membrane during cholinergically conveyed gastric acid secretion.	2002-02	11781141
Human macrophage adhesion on fibronectin: the role of substratum and intracellular signalling kinases.	2002-02	11781139
Encapsulation of an antivasospastic drug, fasudil, into liposomes, and in vitro stability of the fasudil-loaded liposomes.	2002-01-31	11790490
The transcriptional co-activators CBP and p300 are activated via phenylephrine through the p42/p44 MAPK cascade.	2002-01-25	11705990
Protein kinase C increases 11beta-hydroxysteroid dehydrogenase oxidation and inhibits reduction in rat Leydig cells.	2002-01-10	11780917
Involvement of protein kinase C and tyrosin kinase in tumoricidal activation of macrophage induced by Streptococcus pneumoniae type II capsular polysaccharide.	2002-01	11789663
A protein kinase inhibitor as an antimycobacterial agent.	2001-12-18	11750829
Possible involvement of Rho-kinase in the pathogenesis of hypertension in humans.	2001-12-01	11751708
Investigation of the inhibitory effects of HA-1077 and Y-32885 on the translocation of PKCbetaI, PKCbetaII and PKCzeta in human neutrophils.	2001-12	11817672
Effects of anti-myosin drugs on anaphase chromosome movement and cytokinesis in crane-fly primary spermatocytes.	2001-12	11807939
Effects of calcium, calmodulin, protein kinase C and protein tyrosine kinases on volume-activated taurine efflux in human erythroleukemia cells.	2001-12	11748589
Antianginal effects of hydroxyfasudil, a Rho-kinase inhibitor, in a canine model of effort angina.	2001-12	11739249
Serine phosphorylation of GH-activated signal transducer and activator of transcription 5a (STAT5a) and STAT5b: impact on STAT5 transcriptional activity.	2001-12	11731617
Protein kinase inhibitors and the dynamics of tight junction opening and closing in A6 cell monolayers.	2001-11-15	11719854
Phosphorylation is involved in the activation of metal-regulatory transcription factor 1 in response to metal ions.	2001-11-09	11551972
Regulation of matrix metalloproteinase-2 production by cytokines and pharmacological agents in human pulp cell cultures.	2001-11	11716080
Intrathecal application with liposome-entrapped Fasudil for cerebral vasospasm following subarachnoid hemorrhage in rats.	2001-11	11683605
Induction of manganese superoxide dismutase by tumour necrosis factor-alpha in human endometrial stromal cells.	2001-11	11675473
Morphine inhibits indolactam V-induced U937 cell adhesion and gelatinase secretion.	2001-11	11598903
Stimulation of cardiac glucose transport by inhibitors of oxidative phosphorylation.	2001-10-05	11681625
Effect of Leishmania donovani lipophosphoglycan on ornithine decarboxylase activity in macrophages.	2001-10	11695367
Regulation of the rat NHE3 gene promoter by sodium butyrate.	2001-10	11557515
Role of protein kinase C in myogenic calcium-contraction coupling of rat cannulated mesenteric small arteries.	2001-10	11553027
Role of Na(+)/H(+) exchanger during O(2) deprivation in mouse CA1 neurons.	2001-10	11546657
Differential influence of cAMP on the expression of the three subtypes (ATA1, ATA2, and ATA3) of the amino acid transport system A.	2001-09-14	11566196
Involvement of Rho-kinase in vascular remodeling caused by long-term inhibition of nitric oxide synthesis in rats.	2001-09-07	11553365
Ameliorative effect of vasopressin-(4-9) through vasopressin V(1A) receptor on scopolamine-induced impairments of rat spatial memory in the eight-arm radial maze.	2001-09-07	11553362
Antiischemic properties of fasudil in experimental models of vasospastic angina.	2001-09	11676196
Novel protein kinase C delta isoform insensitive to caspase-3.	2001-09	11558579
PP1 inhibitors depolarize Hermissenda photoreceptors and reduce K+ currents.	2001-09	11535678
Dependency of detrusor contractions on calcium sensitization and calcium entry through LOE-908-sensitive channels.	2001-09	11522599
Effects of second messengers on gap junctional intercellular communication of ovine luteal cells throughout the estrous cycle.	2001-09	11514341
Functional characterization of P2Y and P2X receptors in human eosinophils.	2001-09	11473359
P2Y(11) receptor expression by human lymphocytes: evidence for two cAMP-linked purinoceptors.	2001-08-31	11527539
Effect of oleoresin capsicum (OC) and ortho-chlorobenzylidene malononitrile (CS) on ciliary beat frequency.	2001-08-28	11522366
Pharmacological profile of hydroxy fasudil as a selective rho kinase inhibitor on ischemic brain damage.	2001-08-10	11531167
Sea urchin sperm cation-selective channels directly modulated by cAMP.	2001-08-10	11513865
H-7 and fetal calf serum (FCS) act synergistically to increase apoptosis in the KB line of human oral carcinoma cells.	2001-08	11521953
Spl phosphorylation induced by serum stimulates the human alpha2(I) collagen gene expression.	2001-08	11511308
Effects of protein kinase inhibitor, HA1077, on intraocular pressure and outflow facility in rabbit eyes.	2001-08	11483085
Modulation of GABA-augmented norepinephrine release in female rat brain slices by opioids and adenosine.	2001-07	11565619
Angiotensin II type 1 receptor modulation of L-type calcium currents in guinea-pig ventricular cells.	2001-06	11780430
A novel drug delivery system as prophylaxis for cerebral vasospasm.	2001	11563290
Combined administration of Fasudil hydrochloride and nitroglycerin for treatment of cerebral vasospasm.	2001	11563287
Effect of Fasudil HCl, a protein kinase inhibitor, on cerebral vasospasm.	2001	11563286
Microtubule disruption modulates the Rho-kinase pathway in vascular smooth muscle.	2001	11519742

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.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:30:53 GMT 2025` Edited by `admin` on `Mon Mar 31 18:30:53 GMT 2025`
Record UNII	487H9Q0F9N
Record Status	`Validated (UNII)`
Record Version

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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

Code System Code Type Description

EPA CompTox

DTXSID401004756