Structure via PubChem · Public domain (PubChem)
H-89
Sign in to saveAlso known as H 89, N-[2-(4-BROMOCINNAMYLAMINO)ETHYL]-5-ISOQUINOLINE SULFONAMIDE
H-89 is a protein kinase inhibitor with greatest effect on protein kinase A (PKA). H-89, derived from H-8 (N-[2-(methylamino)ethyl]-5-isoquinoline-sulfonamide), was initially believed to act specifically as an inhibitor of PKA, 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. However, subsequent work has suggested a variety of additional effects such as inhibition of other protein kinases ( values of 80, 120, 135, 2
Chemical data
- Formula
- C20H20BrN3O2S
- Molecular weight
- 446.4 g/mol
- IUPAC name
- N-[2-[[(E)-3-(4-bromophenyl)prop-2-enyl]amino]ethyl]isoquinoline-5-sulfonamide
- SMILES
- C1=CC2=C(C=CN=C2)C(=C1)S(=O)(=O)NCCNC/C=C/C3=CC=C(C=C3)Br
- InChIKey
- ZKZXNDJNWUTGDK-NSCUHMNNSA-N
- XLogP
- 3.5
- Polar surface area
- 79.5 Ų
- H-bond donors
- 2
- H-bond acceptors
- 5
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Research
3,173 papers- Tadalafil Reversed H-89 - and Scopolamine - Induced Spatial Learning Impairments in Male Rats.Drug research · 2021
- H-89 potentiates adipogenesis in 3T3-L1 cells by activating insulin signaling independently of protein kinase A.Life sciences · 2007
- Intrahippocampal co-administration of nicotine and O-acetyl-L-carnitine prevents the H-89-induced spatial learning deficits in Morris water maze.Journal of complementary & integrative medicine · 2022
- Melatonin reverses H-89 induced spatial memory deficit: Involvement of oxidative stress and mitochondrial function.Behavioural brain research · 2017
- H-89, a non-specific inhibitor of protein kinase A, promotes post-ischemic cardiac contractile recovery and reduces infarct size.Journal of cardiovascular pharmacology · 2005
via PubMed
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 445.046
Show 4 more facts
- chemical formula
- C₂₀H₂₀BrN₃O₂S
- isomeric SMILES
- C1=CC2=C(C=CN=C2)C(=C1)S(=O)(=O)NCCNC/C=C/C3=CC=C(C=C3)Br
- canonical SMILES
- C1=CC2=C(C=CN=C2)C(=C1)S(=O)(=O)NCCNCC=CC3=CC=C(C=C3)Br
- subject has role
- protein kinase inhibitors
Sources (1)
via Wikidata · CC0
~1 min read
Encyclopedic overview
1 sectionsContents
- References
{{Chembox |Verifiedfields = changed |Watchedfields = changed |verifiedrevid = 443142728 |ImageFile = H 89 dihydrochloride.svg |PIN = N-(2-{[(2E)-3-(4-Bromophenyl)prop-2-en-1-yl]amino}ethyl)isoquinoline-5-sulfonamide |Section1= |Section2= |Section3= }}
H-89 is a protein kinase inhibitor with greatest effect on protein kinase A (PKA). H-89, derived from H-8 (N-[2-(methylamino)ethyl]-5-isoquinoline-sulfonamide), was initially believed to act specifically as an inhibitor of PKA, 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. However, subsequent work has suggested a variety of additional effects such as inhibition of other protein kinases ( values of 80, 120, 135, 270, 2600 and 2800 nM for S6K1, MSK1, PKA, ROCKII, PKBα and MAPKAP-K1b respectively), and direct inhibition of various potassium currents.
Excerpted from Wikipedia’s “H-89” article, available under the CC BY-SA 4.0 licence.