H-89

H-89 is a protein kinase inhibitor with greatest effect on protein kinase A (PKA).^[2] H-89, derived from H-8 (N-[2-(methylamino)ethyl]-5-isoquinoline-sulfonamide),^[3] was initially believed to act specifically as an inhibitor of PKA,^[4] being 30 times more potent than H-8 at inhibiting PKA and 10 times less potent at inhibiting protein kinase G. It achieves this through competitive inhibition of the adenosine triphosphate (ATP) site on the PKA catalytic subunit.^[5] However, subsequent work has suggested a variety of additional effects such as inhibition of other protein kinases (IC₅₀ values of 80, 120, 135, 270, 2600 and 2800 nM for S6K1, MSK1, PKA, ROCKII, PKBα and MAPKAP-K1b respectively),^[6] and direct inhibition of various potassium currents.^[7]

Quick facts Names, Identifiers ...

H-89

Names
Preferred IUPAC name N-(2-{[(2E)-3-(4-Bromophenyl)prop-2-en-1-yl]amino}ethyl)isoquinoline-5-sulfonamide
Identifiers
CAS Number	127243-85-0 Y
3D model (JSmol)	Interactive image
Abbreviations	H-89 H89
ChEBI	CHEBI:47495 Y
ChEMBL	ChEMBL104264 Y
ChemSpider	395827 Y
DrugBank	DB07995
ECHA InfoCard	100.201.023
EC Number	675-767-3
IUPHAR/BPS	5983
PubChem CID	449241
UNII	M876330O56 Y
CompTox Dashboard (EPA)	DTXSID801022528
InChI InChI=1S/C20H20BrN3O2S/c21-18-8-6-16(7-9-18)3-2-11-22-13-14-24-27(25,26)20-5-1-4-17-15-23-12-10-19(17)20/h1-10,12,15,22,24H,11,13-14H2/b3-2+ N Key: ZKZXNDJNWUTGDK-NSCUHMNNSA-N N InChI=1/C20H20BrN3O2S/c21-18-8-6-16(7-9-18)3-2-11-22-13-14-24-27(25,26)20-5-1-4-17-15-23-12-10-19(17)20/h1-10,12,15,22,24H,11,13-14H2/b3-2+ Key: ZKZXNDJNWUTGDK-NSCUHMNNBL
SMILES c1cc2cnccc2c(c1)S(=O)(=O)NCCNC/C=C/c3ccc(cc3)Br
Properties
Chemical formula	C20H20BrN3O2S
Molar mass	446.36 g·mol−1
Solubility in water	Soluble to 25 mM
Solubility in other solvents	up to 100 mM in DMSO
Hazards
Occupational safety and health (OHS/OSH):
Main hazards	Exposure may cause irritation to eyes, mucous membranes, upper respiratory tract, and skin.
GHS labelling:[1]
Pictograms
Signal word	Warning
Hazard statements	H302, H312, H315, H319, H332, H335
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is YN ?) Infobox references

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In addition to its use in studying mechanisms of cell signalling, H-89 has also been used experimentally in vivo. H-89 has been shown to increase the threshold and latency of pentylenetetrazol-induced seizures ^[8] and decrease morphine withdrawal symptoms in mice.^[9]