fasudil   

GtoPdb Ligand ID: 5181

Synonyms: dihydrochloride fasudil | HA 1077 | HA1077
fasudil is an approved drug (1995)
Compound class: Synthetic organic
Comment: Fasudil is a potent inhibitor of the Rho-kinases ROCK1 and ROCK2.
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2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 5
Hydrogen bond donors 1
Rotatable bonds 2
Topological polar surface area 70.68
Molecular weight 291.1
XLogP 0.89
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Canonical SMILES O=S(=O)(c1cccc2c1ccnc2)N1CCNCCC1
Isomeric SMILES O=S(=O)(c1cccc2c1ccnc2)N1CCNCCC1
InChI InChI=1S/C14H17N3O2S/c18-20(19,17-9-2-6-15-8-10-17)14-4-1-3-12-11-16-7-5-13(12)14/h1,3-5,7,11,15H,2,6,8-10H2
InChI Key NGOGFTYYXHNFQH-UHFFFAOYSA-N
References
1. Anastassiadis T, Deacon SW, Devarajan K, Ma H, Peterson JR. (2011)
Comprehensive assay of kinase catalytic activity reveals features of kinase inhibitor selectivity.
Nat. Biotechnol., 29 (11): 1039-45. [PMID:22037377]
2. Asano T, Suzuki T, Tsuchiya M, Satoh S, Ikegaki I, Shibuya M, Suzuki Y, Hidaka H. (1989)
Vasodilator actions of HA1077 in vitro and in vivo putatively mediated by the inhibition of protein kinase.
Br. J. Pharmacol., 98 (4): 1091-100. [PMID:2611484]
3. Doggrell SA. (2005)
Rho-kinase inhibitors show promise in pulmonary hypertension.
Expert Opin Investig Drugs, 14 (9): 1157-9. [PMID:16144499]
4. Gao Y, Davies SP, Augustin M, Woodward A, Patel UA, Kovelman R, Harvey KJ. (2013)
A broad activity screen in support of a chemogenomic map for kinase signalling research and drug discovery.
Biochem. J., 451 (2): 313-28. [PMID:23398362]
5. Huentelman MJ, Stephan DA, Talboom J, Corneveaux JJ, Reiman DM, Gerber JD, Barnes CA, Alexander GE, Reiman EM, Bimonte-Nelson HA. (2009)
Peripheral delivery of a ROCK inhibitor improves learning and working memory.
Behav. Neurosci., 123 (1): 218-23. [PMID:19170447]
6. Löhn M, Plettenburg O, Ivashchenko Y, Kannt A, Hofmeister A, Kadereit D, Schaefer M, Linz W, Kohlmann M, Herbert JM et al.. (2009)
Pharmacological characterization of SAR407899, a novel rho-kinase inhibitor.
Hypertension, 54 (3): 676-83. [PMID:19597037]
7. Ray P, Wright J, Adam J, Bennett J, Boucharens S, Black D, Cook A, Brown AR, Epemolu O, Fletcher D et al.. (2011)
Fragment-based discovery of 6-substituted isoquinolin-1-amine based ROCK-I inhibitors.
Bioorg. Med. Chem. Lett., 21 (1): 97-101. [PMID:21145740]
8. Shibuya M, Suzuki Y. (1993)
[Treatment of cerebral vasospasm by a protein kinase inhibitor AT 877].
No To Shinkei, 45 (9): 819-24. [PMID:8217408]