1.1.1.188: prostaglandin-F synthase

This is an abbreviated version, for detailed information about prostaglandin-F synthase, go to the full flat file.

Reaction

(5Z,13E)-(15S)-9alpha,11alpha,15-trihydroxyprosta-5,13-dienoate
+
NADP+
=
(5Z,13E)-(15S)-9alpha,15-dihydroxy-11-oxoprosta-5,13-dienoate
+
NADPH
+
H+

Synonyms

20alpha-HSD/PGFS, 20alpha-hydroxysteroid dehydrogenase/prostaglandin F-synthase, AKR1B1, AKR1B3, AKR1B7, AKR1C3, aldo-keto reductase, aldo-keto reductase 1C3, ALDR1, ALR2, DD1, dihydrodiol dehydrogenase 1, m-PGFS, More, NADPH-dependent prostaglandin D2 11-keto reductase, PG endoperoxide reductase, PGD 11-ketoreductase, PGD2 11-ketoreductase, PGD2 11-ketoreductase activity, PGF synthase, PGF synthase I, PGF synthase II, PGF2alpha synthase, PGF2alpha-synthetic activity, PGFS, PGFS I, PGFS-I, PGFS-II, PGFSI, PGFSII, PGH 9-,11-endoperoxide reductase, PGH2 9,11-endoperoxidase, PGH2 9,11-endoperoxide reductase, PGH2 9-,11-endoperoxide reductase, prostaglandin 11-keto reductase, prostaglandin 11-ketoreductase, prostaglandin D2 11-ketoreductase, prostaglandin D2-ketoreductase, prostaglandin F synthase, prostaglandin F synthase I, prostaglandin F synthase II, prostaglandin F synthetase, prostaglandin F2alpha synthase, prostaglandin F2alpha-synthase, prostaglandin-D2 11-reductase, prostaglandin-F2alpha synthase, prostamide/PGF synthase, prostamide/prostaglandin F synthase, reductase, 15-hydroxy-11-oxoprostaglandin, synthetase, prostaglandin F2alpha, type 5 17beta-hydroxysteroid dehydrogenase/prostaglandin F synthase, vas deferens protein

ECTree

     1 Oxidoreductases
         1.1 Acting on the CH-OH group of donors
             1.1.1 With NAD+ or NADP+ as acceptor
                1.1.1.188 prostaglandin-F synthase

Inhibitors

Inhibitors on EC 1.1.1.188 - prostaglandin-F synthase

Please wait a moment until all data is loaded. This message will disappear when all data is loaded.
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
(5Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxy-5-phenylpent-1-en-1-yl]cyclopentyl]-N-ethylhept-5-enamide
-
bimatoprost
(5Z)-7-[(1R,4S,5S,6R)-6-[(1E)-oct-1-en-1-yl]-2-azabicyclo[2.2.1]hept-5-yl]hept-5-enoic acid
-
ONO1370
(5Z)-7-[(1R,4S,5S,6R)-6-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-2-azabicyclo[2.2.1]hept-5-yl]hept-5-enoic acid
-
ONO1349
(5Z)-7-[(1S,4S,5S,6R)-2-methyl-6-[(1E)-oct-1-en-1-yl]-2-azabicyclo[2.2.1]hept-5-yl]hept-5-enoic acid
-
ONO1373
(Z)-7-[(1R,4S,5S,6R)-((E)-6-oct-1-enyl)-2-aza-bicyclo[2.2.1]hept-5-yl]-hept-5-enoic acid
-
inhibition of PGH2 9,11-endoperoxide reductase activity, slight inhibition of prostamide D2 11-ketoreductase and PGD2 11-ketoreductase activity
(Z)-7-[(1R,4S,5S,6R)-2-methyl-6-((E)-oct-1-enyl)-2-aza-bicyclo[2.2.1]hept-5-yl]-hept-5-enoic acid
-
inhibition of PGH2 9,11-endoperoxide reductase activity, slight inhibition of prostamide D2 11-ketoreductase and PGD2 11-ketoreductase activity, competitive, binds to the active site
(Z)-7-[(1R,4S,5S,6R)-6-((E)-(S)-3-hydroxy-oct-1-enyl)-2-aza-bicyclo[2.2.1]hept-5-yl]-hept-5-enoic acid
-
inhibition of PGH2 9,11-endoperoxide reductase activity, slight inhibition of prostamide D2 11-ketoreductase and PGD2 11-ketoreductase activity
1-(4-aminobenzyl)-5-methoxy-2-methylindoleacetic acid
-
-
2-(1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl)-N-((trifluoromethyl)sulfonyl)acetamide
257fold selectivity for isoform AKR1C3 over isoform AKR1C2
3-(1-(4-chlorobenzoyl)-3-ethyl-5-methoxy-1H-indol-2-yl)-propanoic acid
540fold selectivity for isoform AKR1C3 over isoform AKR1C2
3-(1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl)-propanoic acid
257fold selectivity for isoform AKR1C3 over isoform AKR1C2
4-benzoyl-benzoic acid
-
;
4-carboxy-2',4'-dinitrodiphenylamine
-
;
4-carboxy-2-aminodiphenylamine
-
;
4-chloro-N-(4-tolyl)-anthranilic acid
-
;
4-chloro-N-phenylanthranilic acid
-
;
4-nitro-N-phenylanthranilic acid
-
;
4-Nitrobenzaldehyde
-
competitive inhibition of PGD2 but not of PGH2 reduction
5-methyl-N-phenylanthranilic acid
-
;
9,10-phenanthrenequinone
acetate
-
occupies the oxyanion hole of the active site, 2 complex structures
Ag+
-
IC50 = 0.005 mM
AgNO3
-
at 0.05 mM 87-100% inhibition, depending on the substrate
aspirin
-
;
bimatoprost
Cd2+
-
IC50 = 0.95 mM
CdSO4
-
at 5 mM 91-100% inhibition, depending on the substrate
Cu2+
-
IC50 = 0.4 mM
CuSO4
-
at 5 mM 93-96% inhibition, depending on the substrate; the liver-type isozyme is 2fold less sensitive than the lung-type isozyme
FeCl2
-
-
Flufenamic acid
-
nonsteroidal anti-inflammatory drug, binds to both the active site and the beta-hairpin loop at the opposite end of the central beta-barrel, complex structure
flurbiprofen
HgCl2
-
at 1 mM 94-100% inhibition, depending on the substrate; IC50 = 0.3 mM, the liver-type isozyme is 2fold less sensitive than the lung-type isozyme
Ibuprofen
indomethacin
indomethacin methyl ester
-
specific inhibition of isoform AKR1C3 versus AKR1C1 and AKR1C3
interferon tau
-
Meclofenamic acid
Mefenamic acid
-
;
N-(4-chlorobenzoyl)-melatonin
NaF
-
-
naproxen
ONO1349
-
-
ONO1370
-
-
ONO1373
-
-
ponalrestat
-
specific inhibitor developed to block AKR1B1 activity. Application reduces prostaglandin F2alpha production in response to interleukin IL-1beta in both cultured endometrial cells and endometrial explants
rutin
-
binding structure at the substrate binding site
salicylic acid
-
;
sorbinil
sulindac
Tolrestat
Zn2+
-
IC50 = 1.4 mM
ZnSO4
-
at 5 mM 71-100% inhibition, depending on the substrate
Zomepirac
additional information
-