H-89

For the Heath H-89 microcomputer, see Zenith Z-89.

H-89
Names

IUPAC name N-[2-[[3-(4-Bromophenyl)-2-propenyl]amino]ethyl]-5-isoquinolinesulfonamide
Identifiers
CAS Number	127243-85-0^Y
3D model (Jmol)	Interactive image
ChEBI	CHEBI:47495^N
ChEMBL	ChEMBL104264^N
ChemSpider	395827^N
ECHA InfoCard	100.201.023
IUPHAR/BPS	5983
PubChem	449241
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 in Water
Solubility	up to 100 mM DMSO
Hazards
Main hazards	Exposure may cause irritation to eyes, mucous membranes, upper respiratory tract and skin.
S-phrases	S22 - Do not breathe dust S24/25 - Avoid contact with skin and eyes S36/37/39 - Wear suitable protective clothing, gloves and eye/face protection
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

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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