SHH

OCTANEDIOIC ACID HYDROXYAMIDE PHENYLAMIDE

Created: 1999-07-30
Last modified:  2021-03-01

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Chemical Details

Formal Charge0
Atom Count39
Chiral Atom Count0
Bond Count39
Aromatic Bond Count6
2D diagram of SHH
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Chemical Component Summary

NameOCTANEDIOIC ACID HYDROXYAMIDE PHENYLAMIDE
SynonymsSAHA
Systematic Name (OpenEye OEToolkits)N-hydroxy-N'-phenyl-octanediamide
FormulaC14 H20 N2 O3
Molecular Weight264.32
TypeNON-POLYMER

Chemical Descriptors

TypeProgram Version Descriptor
SMILESACDLabs10.04O=C(Nc1ccccc1)CCCCCCC(=O)NO
SMILESCACTVS3.341ONC(=O)CCCCCCC(=O)Nc1ccccc1
SMILESOpenEye OEToolkits1.5.0c1ccc(cc1)NC(=O)CCCCCCC(=O)NO
Canonical SMILESCACTVS3.341 ONC(=O)CCCCCCC(=O)Nc1ccccc1
Canonical SMILESOpenEye OEToolkits1.5.0 c1ccc(cc1)NC(=O)CCCCCCC(=O)NO
InChIInChI1.03 InChI=1S/C14H20N2O3/c17-13(15-12-8-4-3-5-9-12)10-6-1-2-7-11-14(18)16-19/h3-5,8-9,19H,1-2,6-7,10-11H2,(H,15,17)(H,16,18)
InChIKeyInChI1.03 WAEXFXRVDQXREF-UHFFFAOYSA-N

Drug Info: DrugBank

DrugBank IDDB02546 
NameVorinostat
Groups
  • approved
  • investigational
DescriptionVorinostat (rINN) or suberoylanilide hydroxamic acid (SAHA), is a drug currently under investigation for the treatment of cutaneous T cell lymphoma (CTCL), a type of skin cancer, to be used when the disease persists, gets worse, or comes back during or after treatment with other medicines. It is the first in a new class of agents known as histone deacetylase inhibitors. A recent study suggested that vorinostat also possesses some activity against recurrent glioblastoma multiforme, resulting in a median overall survival of 5.7 months (compared to 4 - 4.4 months in earlier studies). Further brain tumor trials are planned using combinations of vorinostat with other drugs.
Synonyms
  • SAHA
  • Suberanilohydroxamic acid
  • SHH
  • Octanedioic acid hydroxyamide phenylamide
  • Vorinostat
Brand NamesZolinza
IndicationFor the treatment of cutaneous manifestations in patients with cutaneous T-cell lymphoma who have progressive, persistent or recurrent disease on or following two systemic therapies.
Categories
  • Amides
  • Amines
  • Anilides
  • Aniline Compounds
  • Antineoplastic Agents
ATC-CodeL01XH01
CAS number149647-78-9

Drug Targets

NameTarget SequencePharmacological ActionActions
Histone deacetylase 1MAQTQGTRRKVCYYYDGDVGNYYYGQGHPMKPHRIRMTHNLLLNYGLYRK...unknowninhibitor
Histone deacetylase 2MAYSQGGGKKKVCYYYDGDIGNYYYGQGHPMKPHRIRMTHNLLLNYGLYR...unknowninhibitor
Histone deacetylase 3MAKTVAYFYDPDVGNFHYGAGHPMKPHRLALTHSLVLHYGLYKKMIVFKP...unknowninhibitor
Histone deacetylase 6MTSTGQDSTTTRQRRSRQNPQSPPQDSSVTSKRNIKKGAVPRSIPNLAEV...unknowninhibitor
Histone deacetylase 8MEEPEEPADSGQSLVPVYIYSPEYVSMCDSLAKIPKRASMVHSLIEAYAL...unknown
View More
Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

Related Resource References

Resource NameReference
Pharos CHEMBL98
PubChem 5311
ChEMBL CHEMBL98
ChEBI CHEBI:45716
CCDC/CSD IQILAW, IQILAW03, IQILAW01, IQILAW02, FAKMOV
COD 7206988, 7206989, 7206991