H-89

H-89
Names
	IUPAC name N-[2-[[3-(4-Bromophenyl)-2-propenyl]amino]ethyl]-5-isoquinolinesulfonamide
Identifiers
CAS Number	127243-85-0 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:47495 ;
ChEMBL	ChEMBL104264 ;
ChemSpider	395827 ;
ECHA InfoCard	100.201.023
IUPHAR/BPS	5983;
PubChem CID	449241;
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+ Key: ZKZXNDJNWUTGDK-NSCUHMNNSA-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 in Water
Solubility	up to 100 mM DMSO
Hazards
	Occupational safety and health (OHS/OSH):
Main hazards	Exposure may cause irritation to eyes, mucous membranes, upper respiratory tract and skin.
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

H-89 is a Protein kinase A inhibitor that also inhibits several other kinases (IC50 values are 80, 120, 135, 270, 2600 and 2800 nM for S6K1, MSK1, PKA, ROCKII, PKBα and MAPKAP-K1b).^[1]^[2] H-89 blocks PKA actions through competitive inhibition of the adenosine triphosphate (ATP) site on the PKA catalytic subunit.^[3]

H-89 and seizure

Recent study showed that using H-89 in the pentylenetetrazol-induced seizure in the wild type mice increase seizure threshold and latency.^[4]

H-89 and morphine withdrawal syndrome

The effect of H-89 (0.5, 1, 5 mg/kg) has been studied in morphine withdrawal syndrome in wild-type mice. The results indicated that H-89 significantly reduced the morphine withdrawal syndrome. In addition, results show that combination of H-89 with bucladesine as a cAMP analog has a additive attenuating effect on morphine withdrawal syndrome ^[5]

References

^ Marunaka, Yoshinori; Niisato, Naomi (2003). "H89, an inhibitor of protein kinase A (PKA), stimulates Na+ transport by translocating an epithelial Na+ channel (ENaC) in fetal rat alveolar type II epithelium". Biochemical Pharmacology. 66 (6): 1083–9. doi:10.1016/S0006-2952(03)00456-8. PMID 12963496.
^ Lochner, A.; Moolman, J. A. (2006). "The Many Faces of H89: A Review". Cardiovascular Drug Reviews. 24 (3–4): 261–74. doi:10.1111/j.1527-3466.2006.00261.x. PMID 17214602.
^ Murray, A. J. (2008). "Pharmacological PKA Inhibition: All May Not Be What It Seems". Science Signaling. 1 (22): re4. doi:10.1126/scisignal.122re4. PMID 18523239.
^ Hosseini-Zare, Mahshid Sadat; Salehi, Forouz; Seyedi, Seyedeh Yalda; Azami, Kian; Ghadiri, Tahereh; Mobasseri, Mohammad; Gholizadeh, Shervin; Beyer, Cordian; Sharifzadeh, Mohammad (2011). "Effects of pentoxifylline and H-89 on epileptogenic activity of bucladesine in pentylenetetrazol-treated mice". European Journal of Pharmacology. 670 (2–3): 464–70. doi:10.1016/j.ejphar.2011.09.026. PMID 21946102.
^ Seyedi, Seyedeh Y.; Salehi, Forouz; Payandemehr, Borna; Hossein, Sara; Hosseini-Zare, Mahshid S.; Nassireslami, Ehsan; Yazdi, Behnoosh B.; Sharifzadeh, Mohammad (2014). "Dual effect of cAMP agonist on ameliorative function of PKA inhibitor in morphine-dependent mice". Fundamental & Clinical Pharmacology. 28 (4): 445–54. doi:10.1111/fcp.12045. PMID 24033391.

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[1] Marunaka, Yoshinori; Niisato, Naomi (2003). "H89, an inhibitor of protein kinase A (PKA), stimulates Na+ transport by translocating an epithelial Na+ channel (ENaC) in fetal rat alveolar type II epithelium". Biochemical Pharmacology. 66 (6): 1083–9. doi:10.1016/S0006-2952(03)00456-8. PMID 12963496.

[2] Lochner, A.; Moolman, J. A. (2006). "The Many Faces of H89: A Review". Cardiovascular Drug Reviews. 24 (3–4): 261–74. doi:10.1111/j.1527-3466.2006.00261.x. PMID 17214602.

[example_web_reference-3] Murray, A. J. (2008). "Pharmacological PKA Inhibition: All May Not Be What It Seems". Science Signaling. 1 (22): re4. doi:10.1126/scisignal.122re4. PMID 18523239.

[4] Hosseini-Zare, Mahshid Sadat; Salehi, Forouz; Seyedi, Seyedeh Yalda; Azami, Kian; Ghadiri, Tahereh; Mobasseri, Mohammad; Gholizadeh, Shervin; Beyer, Cordian; Sharifzadeh, Mohammad (2011). "Effects of pentoxifylline and H-89 on epileptogenic activity of bucladesine in pentylenetetrazol-treated mice". European Journal of Pharmacology. 670 (2–3): 464–70. doi:10.1016/j.ejphar.2011.09.026. PMID 21946102.

[5] Seyedi, Seyedeh Y.; Salehi, Forouz; Payandemehr, Borna; Hossein, Sara; Hosseini-Zare, Mahshid S.; Nassireslami, Ehsan; Yazdi, Behnoosh B.; Sharifzadeh, Mohammad (2014). "Dual effect of cAMP agonist on ameliorative function of PKA inhibitor in morphine-dependent mice". Fundamental & Clinical Pharmacology. 28 (4): 445–54. doi:10.1111/fcp.12045. PMID 24033391.

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