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Literature summary for 1.1.1.B40 extracted from

  • Olson, S.; Aster, S.D.; Brown, K.; Carbin, L.; Graham, D.W.; Hermanowski-Vosatka, A.; LeGrand, C.B.; Mundt, S.S.; Robbins, M.A.; Schaeffer, J.M.; Slossberg, L.H.; Szymonifka, M.J.; Thieringer, R.; Wright, S.D.; Balkovec, J.M.
    Adamantyl triazoles as selective inhibitors of 11beta-hydroxysteroid dehydrogenase type 1 (2005), Bioorg. Med. Chem. Lett., 15, 4359-4362.
    View publication on PubMed

Inhibitors

Inhibitors Comment Organism Structure
3-((3r,5r,7r)-adamantan-1-yl)-6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a]azepine isozyme 11beta-HSD1 IC50: 74 nM, isozyme 11beta-HSD2 IC50: 0.004 mM Homo sapiens
3-((3r,5r,7r)-adamantan-1-yl)-6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a]azepine isozyme 11beta-HSD1 IC50: 74 nM, isozyme 11beta-HSD2 IC50: 0.004 mM Mus musculus
3-(3,4,7-trimethyltricyclo[3.3.1.13,7]dec-1-yl)-6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a]azepine isozyme 11beta-HSD1 IC50: 180 nM, isozyme 11beta-HSD2 IC50: 0.004 mM Homo sapiens
3-(3,4,7-trimethyltricyclo[3.3.1.13,7]dec-1-yl)-6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a]azepine isozyme 11beta-HSD1 IC50: 180 nM, isozyme 11beta-HSD2 IC50: 0.004 mM Mus musculus
3-(3,4-dimethyltricyclo[3.3.1.13,7]dec-1-yl)-6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a]azepine isozyme 11beta-HSD1 IC50: 13 nM, isozyme 11beta-HSD2 IC50: 0.00255 mM Homo sapiens
3-(3,4-dimethyltricyclo[3.3.1.13,7]dec-1-yl)-6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a]azepine isozyme 11beta-HSD1 IC50: 13 nM, isozyme 11beta-HSD2 IC50: 0.00255 mM Mus musculus
3-(3,5-dimethyladamantylmethyl)-6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a]azepine isozyme 11beta-HSD1 IC50: 36 nM, isozyme 11beta-HSD2 IC50: 0.0176 mM Homo sapiens
3-(3,5-dimethyladamantylmethyl)-6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a]azepine isozyme 11beta-HSD1 IC50: 36 nM, isozyme 11beta-HSD2 IC50: 0.0176 mM Mus musculus
3-(3-bromotricyclo[3.3.1.13,7]dec-1-yl)-6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a]azepine isozyme 11beta-HSD1 IC50: 23 nM, isozyme 11beta-HSD2 IC50: 0.004 mM Homo sapiens
3-(3-bromotricyclo[3.3.1.13,7]dec-1-yl)-6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a]azepine isozyme 11beta-HSD1 IC50: 23 nM, isozyme 11beta-HSD2 IC50: 0.004 mM Mus musculus
3-(3-fluorotricyclo[3.3.1.13,7]dec-1-yl)-6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a]azepine isozyme 11beta-HSD1 IC50: 37 nM, isozyme 11beta-HSD2 IC50: 0.004 mM Homo sapiens
3-(3-fluorotricyclo[3.3.1.13,7]dec-1-yl)-6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a]azepine isozyme 11beta-HSD1 IC50: 37 nM, isozyme 11beta-HSD2 IC50: 0.004 mM Mus musculus
3-(3-phenyltricyclo[3.3.1.13,7]dec-1-yl)-6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a]azepine isozyme 11beta-HSD1 IC50: 2.3 nM, isozyme 11beta-HSD2 IC50: 23 nM Homo sapiens
3-(3-phenyltricyclo[3.3.1.13,7]dec-1-yl)-6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a]azepine isozyme 11beta-HSD1 IC50: 2.3 nM, isozyme 11beta-HSD2 IC50: 23 nM Mus musculus
3-(6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a]azepin-3-yl)tricyclo[3.3.1.13,7]decan-1-ol isozyme 11beta-HSD1 IC50: 739 nM, isozyme 11beta-HSD2 IC50: 0.004 mM Homo sapiens
3-(6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a]azepin-3-yl)tricyclo[3.3.1.13,7]decan-1-ol isozyme 11beta-HSD1 IC50: 739 nM, isozyme 11beta-HSD2 IC50: 0.004 mM Mus musculus
3-(adamantan-1-yl)-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridine isozyme 11beta-HSD1 IC50: 7.8 nM, isozyme 11beta-HSD2 IC50: above 0.003 mM Homo sapiens
3-(adamantan-1-yl)-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridine isozyme 11beta-HSD1 IC50: 98 nM, isozyme 11beta-HSD2 IC50: above 0.01 mM Mus musculus
3-(tricyclo[3.3.1.13,7]dec-1-yl)-6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a]azepine isozyme 11beta-HSD1 IC50: 7.7 nM, isozyme 11beta-HSD2 IC50: 0.004 mM Homo sapiens
3-(tricyclo[3.3.1.13,7]dec-1-yl)-6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a]azepine isozyme 11beta-HSD1 IC50: 7.7 nM, isozyme 11beta-HSD2 IC50: 0.004 mM Mus musculus
adamantyl triazoles eight derivatives of different ring size, IC50 of 1.4-2180 nM for isozyme 11beta-HSD1, and of 8.7-2000 nM for isozyme 11beta-HSD2, the IC50 value decreases with increasing ring size, overview Homo sapiens
adamantyl triazoles eight derivatives of different ring size, IC50 of 1.4-2180 nM for isozyme 11beta-HSD1, and of 8.7-2000 nM for isozyme 11beta-HSD2, the IC50 value decreases with increasing ring size, overview Mus musculus
n-alkyl-substituted adamantyl triazoles substituted with methyl to butyl groups, IC50: of 3-72 nM for isozyme 11beta-HSD1, and of about 0.004 mM for isozyme 11beta-HSD2, overview Homo sapiens
n-alkyl-substituted adamantyl triazoles substituted with methyl to butyl groups, IC50: of 3-72 nM for isozyme 11beta-HSD1, and of about 0.004 mM for isozyme 11beta-HSD2, overview Mus musculus

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
cortisol + NAD+ Homo sapiens isozyme 11beta-HSD2 catalyzes the reverse reaction with cofactor NAD+ cortisone + NADH
-
ir
cortisol + NAD+ Mus musculus isozyme 11beta-HSD2 catalyzes the reverse reaction with cofactor NAD+ cortisone + NADH
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ir

Organism

Organism UniProt Comment Textmining
Homo sapiens P80365 isozymes 11beta-HSD1 and 11beta-HSD2
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Mus musculus P51661 isozymes 11beta-HSD1 and 11beta-HSD2
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Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
cortisol + NAD+ isozyme 11beta-HSD2 catalyzes the reverse reaction with cofactor NAD+ Homo sapiens cortisone + NADH
-
ir
cortisol + NAD+ isozyme 11beta-HSD2 catalyzes the reverse reaction with cofactor NAD+ Mus musculus cortisone + NADH
-
ir

Synonyms

Synonyms Comment Organism
11beta-HSD2
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Homo sapiens
11beta-HSD2
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Mus musculus