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6-ketoprostaglandin f1 alpha

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Description

6-Ketoprostaglandin F1 alpha: The physiologically active and stable hydrolysis product of EPOPROSTENOL. Found in nearly all mammalian tissue. [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

6-oxoprostaglandin F1alpha : A prostaglandin Falpha that is prostaglandin F1alpha bearing a keto substituent at the 6-position. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID5280888
CHEMBL ID2074840
CHEBI ID28158
SCHEMBL ID4343736
MeSH IDM0023262

Synonyms (64)

Synonym
CHEBI:28158 ,
6-ketoprostaglandin f1alpha
6-oxoprostaglandin f1alpha
(13e,15s)-9alpha,11alpha,15-trihydroxy-6-oxoprost-13-en-1-oic acid
MLS000028869
6-keto prostaglandin f1alpha
smr000058896
SMP2_000282
LMFA03010001
6-oxo-pgf1alpha
6-oxo-prostaglandin f1alpha
6-oxo-9s,11r,15s-trihydroxy-13e-prostenoic acid
BSPBIO_001457
IDI1_033927
6-keto-pgf1a
58962-34-8
6-keto-prostaglandin f1a
C05961
6-keto-pgf1alpha
6-keto-prostaglandin f1alpha
NCGC00161289-02
NCGC00161289-01
NCGC00161289-03
prost-13-en-1-oic acid, 9,11,15-trihydroxy-6-oxo-, (9alpha,11alpha,13e,15s)-
6-ketoprostaglandin f1 alpha
prostaglandin f1a, 6-oxo-
DE7EA974-152E-4B77-88BF-F809636EB050
HMS1989I19
BML1-G02
HMS1791I19
HMS1361I19
SCHEMBL4343736
7-[(1r,2r,3r,5s)-3,5-dihydroxy-2-[(e,3s)-3-hydroxyoct-1-enyl]cyclopentyl]-6-oxoheptanoic acid
pgf1 alpha 6-keto
bdbm82211
cas_58962-34-8
prosta-13-en-1-oic acid, 9,11,15-trihydroxy-6-oxo-, (9alpha,11alpha,13e,15s)-
unii-8urb805jjj
8urb805jjj ,
6-keto-prostaglandin f1-alpha
6-ketoprostaglandin f1|a
CHEMBL2074840
KFGOFTHODYBSGM-ZUNNJUQCSA-N
6-keto pgf1alpha
6-keto-pgf1.alpha.
6-oxo-pgf1.alpha.
prost-13-en-1-oic acid, 9,11,15-trihydroxy-6-oxo-, (9.alpha.,11.alpha.,13e,15s)-
6-ketoprostaglandin f1.alpha.
HMS3402I19
HMS3648L05
6-oxoprostaglandin f1a
6-oxo-9s,11r,15s-trihydroxy-13e-prostenoate
6-oxo-pgf1a
7-((1r,2r,3r,5s)-3,5-dihydroxy-2-((s,e)-3-hydroxyoct-1-enyl)cyclopentyl)-6-oxoheptanoic acid
Q27103534
SR-01000946444-1
sr-01000946444
6-keto-prostaglandin f1 alpha
6-oxo-9alpha,11alpha,15s-trihydroxy-prost-13e-en-1-oic acid
DTXSID001317937
PD020580
CS-0062290
6-keto prostaglandin f1|a
HY-113358

Research Excerpts

Toxicity

ExcerptReferenceRelevance
"The toxic effect of cyclosporine A (CsA) on pancreatic islet beta-cells and the preventive effect of ligustrazine (LIG) on CsA-associated beta-cell toxicity in SD rats were investigated."( [Prevention of toxicity of cyclosporine A on rat pancreatic islet beta-cells by Ligustrazine].
Gu, MJ; Liu, ZM, 1993
)
0.29
" Current hyperosmolar dialysis fluids are toxic to peritoneal cells and inhibit certain host-defence functions."( Dialysis fluid cytotoxicity and inhibition of host defence in cultured human mesothelial cells are neutralized rapidly with incubation in the peritoneum.
Dodd, PD; Gokal, R; Rooney, OB; Walker, MG, 1996
)
0.29
" We concluded that, based on markers of endothelial damage, BPAECs showed no apparent ability to metabolize MCT to a reactive intermediate nor to further metabolize GSH-DHP to a toxic species."( Comparative cytotoxicity of monocrotaline and its metabolites in cultured pulmonary artery endothelial cells.
Dunston, SD; Jones, AD; Lamé, MW; Segall, HJ; Taylor, DW; Wilson, DW, 1997
)
0.3

Pharmacokinetics

ExcerptReferenceRelevance
" Only minor differences in the pharmacokinetic parameters were observed between the younger and elderly patients."( The pharmacokinetics of flurbiprofen in younger and elderly patients with rheumatoid arthritis.
Antal, EJ; Buchanan, WW; Cauvier, H; Grace, EM; Kean, WF; Rischke, J, 1992
)
0.28
" In normotensive subjects with normal renal function, cicletanine was rapidly and regularly absorbed, its apparent elimination half-life established around 7 h, and both its renal clearance (0."( Influence of renal insufficiency on the pharmacokinetics of cicletanine and its effects on the urinary excretion of electrolytes and prostanoids.
Benzoni, D; Cuisinaud, G; Ferry, N; Geoffroy, J; Pozet, N; Sassard, J; Zech, PY, 1988
)
0.27
" To test these possibilities we examined the sex-related differences in (1) vessel wall PGI2 release and its inhibition by and recovery from aspirin in rabbits; (2) the effects of aspirin on platelet aggregation, thromboxane B2 and beta-thromboglobulin (BTG) release in man, and (3) the pharmacokinetic characteristics of aspirin, in both rabbits and man."( The sex-related differences in aspirin pharmacokinetics in rabbits and man and its relationship to antiplatelet effects.
Buchanan, MR; Butt, R; Hirsh, J; Rischke, JA; Rosenfeld, J; Turpie, AG, 1983
)
0.27
" We tested the hypotheses that alterations in the metabolic clearance rate and the half-life of angiotensin II account for reduced pressor dose-responses during gestation and that angiotensin II increases circulating levels of vasodilatory prostaglandins I2 and E2 relative to thromboxane A2."( Angiotensin II metabolic clearance rate and pressor responses in nonpregnant and pregnant women.
Cox, K; Gant, NF; Magness, RR; Rosenfeld, CR, 1994
)
0.29
" The angiotensin II metabolic clearance rate and half-life were similar in nonpregnant and pregnant women: metabolic clearance rate = 85 +/- 10 versus 68 +/- 3 ml/min."( Angiotensin II metabolic clearance rate and pressor responses in nonpregnant and pregnant women.
Cox, K; Gant, NF; Magness, RR; Rosenfeld, CR, 1994
)
0.29
"A selective thromboxane (TX) synthase inhibitor, CS-518, was orally administered to healthy male Japanese volunteers and the pharmacokinetic and pharmacodynamic properties were investigated."( Pharmacokinetic and pharmacodynamic profiles of CS-518, a selective, long-lasting thromboxane synthase inhibitor, after single and multiple oral administration to healthy volunteers.
Inaba, H; Kosuge, K; Mizuno, A; Nagashima, S; Nakashima, M; Uematsu, T, 1994
)
0.29
" In the single-dose study (200, 300, 400 mg), the area under the plasma concentration-time curve (AUC) and the maximum plasma concentration (Cmax) increased non-linearly with dose, while the mean elimination half-life (V0) was essentially unchanged (3."( Pharmacokinetic and pharmacodynamic properties of FK070 (KDI-792), a novel thromboxane receptor antagonist/thromboxane synthetase inhibitor, after single and multiple oral administrations to healthy volunteers.
Kosuge, K; Nakano, M; Nakashima, M; Terakawa, M; Uematsu, T; Umemura, K, 1996
)
0.29
"Terbogrel is a potent agent having two distinct, complimentary pharmacodynamic actions, namely inhibition of thromboxane synthase and antagonism of the TxA2 receptor."( Pharmacokinetics and pharmacodynamics of terbogrel, a combined thromboxane A2 receptor and synthase inhibitor, in healthy subjects.
Guth, BD; Narjes, H; Nehmiz, G; Riedel, A; Schubert, HD; Tanswell, P, 2004
)
0.32

Compound-Compound Interactions

ExcerptReferenceRelevance
"The simultaneous determination of prostaglandin E2 (PGE2), prostaglandin F2 alpha (PGF2 alpha) and 6-oxoprostaglandin F1 alpha (6-oxo-PGF1 alpha) in urine using immunoaffinity chromatography in combination with negative ion chemical ionization gas chromatography-tandem mass spectrometry (NICI-GC-MS-MS) is described."( Simultaneous determination of the primary prostanoids prostaglandin E2, prostaglandin F2 alpha and 6-oxoprostaglandin F1 alpha by immunoaffinity chromatography in combination with negative ion chemical ionization gas chromatography-tandem mass spectrometr
Mackert, G; Reinke, M; Schweer, H; Seyberth, HW, 1989
)
0.28
"These results offer a strong case for exploring the possibility that in humans MMF combined with COX-2 inhibitors has a role in the treatment options for lupus nephritis."( Mycophenolate mofetil combined with a cyclooxygenase-2 inhibitor ameliorates murine lupus nephritis.
Abbate, M; Benigni, A; Casiraghi, F; Corna, D; Noris, M; Pagnoncelli, M; Remuzzi, G; Rottoli, D; Zoja, C, 2001
)
0.31
" The in vivo antithrombotic property of ibudilast (CAS 50847-11-5), a phosphodiesterase 4 (PDE4) inhibitor, was evaluated in a photochemically-induced guinea pig carotid artery thrombosis model in combination with low-dose ASA."( Ibudilast, a phosphodiesterase inhibitor, in combination with low-dose aspirin potently inhibits guinea pig carotid artery thrombosis without extending bleeding time and causing gastric mucosal injury.
Hoshina, K; Manita, S; Matsuzawa, S; Miyata, Y; Ooie, T; Sasahara, T; Sueyoshi, S; Yasue, T, 2012
)
0.38
"Previous studies have found that Panax quinquefolius saponins (PQS) combined with dual antiplatelet therapy (DAPT) of aspirin and clopidogrel enhances antithrombotic effects while reducing gastric mucosal injury induced by DAPT."( Panax quinquefolius saponins combined with dual antiplatelet drug therapy alleviate gastric mucosal injury and thrombogenesis through the COX/PG pathway in a rat model of acute myocardial infarction.
Kou, N; Miao, Y; Qu, H; Shi, DZ; Wang, MM; Xue, M; Yang, B; Yang, L; Zang, MX, 2018
)
0.48
"To explore the anti-platelet aggregation and anti-thrombotic mechanisms of Trichosanthis Fructus combined with aspirin based on network pharmacology and the validation of arteriovenous by pass model in rats."( [Anti-platelet aggregation and anti-thrombotic mechanism of Trichosanthis Fructus combined with aspirin based on network pharmacology].
Bian, YY; Wang, LL; Yan, HY; Zou, CC, 2019
)
0.51
"PNS combined with DAPT increased anti-thrombosis effects of DAPT and mitigated DAPT-related gastric injury."( Panax Notoginseng Saponins Combined with Dual Antiplatelet Drugs Potentiates Anti-Thrombotic Effect with Alleviated Gastric Injury in A Carotid Artery Thrombosis Rat Model.
Gu, Y; Kou, N; Ma, Y; Miao, Y; Shi, D; Tang, Z; Wang, M; Wang, W; Wu, Y; Xue, M; Yang, L, 2022
)
0.72

Bioavailability

ExcerptReferenceRelevance
"4 microM) inhibitory activities, was found to be orally bioavailable with a long duration of action and offered effective protection against mortality in a collagen-epinephrine-induced pulmonary thromboembolism model in mice."( 3,4-Dihydroquinolin-2(1H)-ones as combined inhibitors of thromboxane A2 synthase and cAMP phosphodiesterase.
Bruno, JJ; Hirschfeld, DR; Maloney, PJ; Martinez, GR; Walker, KA; Yang, DS, 1992
)
0.28
" The synthesis of prostacyclin and its bioavailability may be an important local determinant for metastasis."( Biological half-life of prostacyclin and 6-oxo-PGF1 alpha levels in plasma of patients with colonic cancer.
Peskar, BA; Polterauer, P; Sinzinger, H, 1986
)
0.27
" Bioavailability was 50% due to a pronounced first-pass effect."( Single intravenous and oral doses of fenflumizole: pharmacokinetics and effects on prostanoid formation.
Arnold, E; Midskov, C; Rasmussen, SN; Vinge, E, 1985
)
0.27
" In the present study, we evaluated the potential of omeprazole to interfere with the bioavailability of aspirin administered to rats either alone or complexed with the zwitterionic phospholipid, dipalmitoylphosphatidylcholine (DPPC)."( Effect of omeprazole on the bioavailability of unmodified and phospholipid-complexed aspirin in rats.
Dial, EJ; Felder, TB; Giraud, MN; Illich, PA; Lichtenberger, LM; Sanduja, SK, 1997
)
0.3
"Gastric absorption of aspirin and its relative bioavailability were reduced by an antisecretory dose of omeprazole; its inhibitory effect on gastric prostaglandin synthesis was consequently attenuated."( Effect of omeprazole on the bioavailability of unmodified and phospholipid-complexed aspirin in rats.
Dial, EJ; Felder, TB; Giraud, MN; Illich, PA; Lichtenberger, LM; Sanduja, SK, 1997
)
0.3
" The failure of a receptor blocker of leukotrienes to moderate disease expression suggests either a less important role for these chemicals in AOM or an insufficient bioavailability of the specific MK 571 inhibitor."( Expression of acute otitis media after receptor blockade of platelet activating factor, thromboxane, and leukotrienes in the chinchilla.
Alper, CM; Burckart, GJ; Diven, WF; Doyle, WJ; Evans, RW; Jaffe, R, 1998
)
0.3
"Our results, obtained in healthy women in recent menopause, indicate that the ratio between vasodilator (NOx and prostacyclin) and vasoconstrictor (ET) bioavailability shifted towards the previous ones after O-ET, while it remained unchanged after T-ET; moreover, catecholamines levels were reduced by both treatments already from 1 month of therapy."( Estrogen therapy effects on different vasoactive factors in recent postmenopausal healthy women.
Maffei, S; Mercuri, A; Vassalle, C; Zucchelli, GC, 2006
)
0.33
"In the mouse model of dilated cardiomyopathy, endothelial dysfunction in coronary circulation is present in the late but not the early stage of heart failure pathology and is characterized by a decrease in NO bioavailability and a compensatory increase in PGI(2)."( NO and PGI(2) in coronary endothelial dysfunction in transgenic mice with dilated cardiomyopathy.
Chlopicki, S; Csanyi, G; Drelicharz, L; Gebska, A; Guzik, T; Heinze-Paluchowska, S; Jasinski, A; Kozlovski, V; Mende, U; Olszanecki, R; Skorka, T; Wojnar, L, 2008
)
0.35
" These results show that transient reduction in NO bioavailability does not modify thromboresistance in healthy mice after exercise."( Vascular Nitric Oxide-Superoxide Balance and Thrombus Formation after Acute Exercise.
Chlopicki, S; Czarny, J; Proniewski, B; Przyborowski, K; Sitek, B; Smeda, M; Zakrzewska, A; Zoladz, JA, 2018
)
0.48

Dosage Studied

ExcerptRelevanceReference
" 7e, 9e, 13a, 13d, 18, 20, 21, and 23, when dosed orally in conscious spontaneously hypertensive rats."( 3,4-Dihydroquinolin-2(1H)-ones as combined inhibitors of thromboxane A2 synthase and cAMP phosphodiesterase.
Bruno, JJ; Hirschfeld, DR; Maloney, PJ; Martinez, GR; Walker, KA; Yang, DS, 1992
)
0.28
"6MNA, the active metabolite of the non-acidic anti-inflammatory drug nabumetone, was investigated using intravenous administration for effects on (a) carrageenan paw oedema and gastric irritancy compared to either oral nabumetone or both oral and intravenous indomethacin when given acutely and (b) gastrointestinal irritancy when given in repeat dosing studies."( Anti-inflammatory and gastrointestinal effects of nabumetone or its active metabolite, 6MNA (6-methoxy-2-naphthylacetic acid): comparison with indomethacin.
Blower, PR; Gentry, C; Kelvin, AS; Melarange, R; Neil, C; O'Connell, C; Toseland, CD, 1992
)
0.28
" To explain this phenomenon, 6-keto-PGF1 alpha and von Willebrand factor were dosed in the incubation media."( In vitro platelets/endothelial cells interactions in presence of acetylsalicylic acid at various dosages.
de Sèze, O; Doutremepuich, C; Lalanne, MC; Ramboer, I, 1992
)
0.28
" (d) Yohimbine, but not prazosin, suppressed the noradrenaline dose-response curve for prostaglandin production."( Noradrenaline-induced prostaglandin production by sympathetic postganglionic neurons is mediated by alpha 2-adrenergic receptors.
Goldyne, ME; Gonzales, R; Levine, JD; Sherbourne, CD, 1991
)
0.28
" Tachyphylaxis was not noted in 5 control pigs given sequential repeats of the PAF dosing series."( In vivo enhancement of platelet activating factor-induced prostacyclin production by OKY-046, a selective inhibitor of thromboxane A2 synthase.
Davenport, NJ; Feuerstein, GZ; Goldstein, RE, 1991
)
0.28
" Dose-response curves for platelet aggregation to collagen were obtained in the presence and absence of 1 nmol/L PGI2 to quantify the antiaggregation effects of PGI2."( Inhibition of platelet aggregation by prostacyclin is attenuated after exercise in patients with angina pectoris.
Ashikaga, T; Kishi, Y; Numano, F, 1992
)
0.28
"The pharmacokinetics of flurbiprofen (Ansaid Tablets, Upjohn Company of Canada, Don Mills, Ontario) were evaluated in both younger (40 to 60 years) and elderly (65 to 83 years) rheumatoid arthritic patients after both a 100-mg single-dose administration and at steady state during a 100-mg twice-a-day dosage regimen."( The pharmacokinetics of flurbiprofen in younger and elderly patients with rheumatoid arthritis.
Antal, EJ; Buchanan, WW; Cauvier, H; Grace, EM; Kean, WF; Rischke, J, 1992
)
0.28
" Linear regression analysis of the average for each dose from three different placentas was used to determine the dose-response relationship."( Dose-related action of gonadotropin-releasing hormone on basal prostanoid production from the human term placenta.
Forman, J; Kang, IS; Koong, MK; Siler-Khodr, TM, 1991
)
0.28
" Infusing endotoxin at a higher dosage (40 ng."( Imbalance between plasma levels of thromboxane B2 and 6-keto-prostaglandin F1 alpha during subacute endotoxin-induced hyperdynamic sepsis or multiple organ failure syndrome in sheep.
Morel, DR; Pittet, JF, 1991
)
0.28
" The results indicate that (i) colloidal bismuth subcitrate-induced stimulation of endogenous prostacyclin content ("adaptive cytoprotection") of rat gastroduodenal mucosa may contribute to its therapeutic effect; (ii) the effect of colloidal bismuth subcitrate is not due exclusively to the bismuth content of the molecule, but seems to be connected with the structure of colloidal bismuth subcitrate itself; (iii) the effect seems to be dose-dependent, showing a dose-response relationship."( Colloidal bismuth subcitrate evokes adaptive cytoprotection in rat gastric mucosa.
Balint, GA, 1991
)
0.28
" Dosage of PGI2 was 2-5 ng/kg/min intravenous drip."( [Treatment of acute cerebral infarction with PGI2--evaluating the clinical effect and observation of dynamic changes in plasma TXB2 and 6-keto PGF1 alpha levels].
Zhao, J, 1991
)
0.28
" A dose-response curve was carried out using this free radical-generating system and differing levels of captopril."( Captopril, an ACE inhibitor, for optimizing reperfusion after acute myocardial infarction.
Das, DK; Engelman, RM; Iyengar, J; Rousou, JA, 1991
)
0.28
" Gastroduodenal mucosal damage was assessed 2 hours after aspirin dosage by video-endoscopic techniques."( Age does not influence acute aspirin-induced gastric mucosal damage.
Avots-Avotins, A; Bjorkman, DJ; Mitchell, MD; Moore, JG, 1991
)
0.28
" Platelet function and urinary prostaglandin production were assessed immediately before and on the seventh day of dosing in both studies and in the second study, repeated on the tenth day of dosing."( Selective inhibition of platelet cyclooxygenase with controlled release, low-dose aspirin.
McLeod, LJ; Roberts, MS; Seville, PR; Vial, JH, 1990
)
0.28
" In addition, the similarity of the dose-response curves for the bradykinin-mediated increase in Ca2+, PGE2, and cAMP (half-maximal stimulation of 12, 11, and 13 nM, respectively) and the ability of the B2-antagonist (B4307) to block each of these effects of bradykinin suggest that all three effects are mediated by the same bradykinin (B2) receptor."( Effects of kinins on cultured arterial smooth muscle.
Breckon, R; Dixon, BS; Fortune, J; Linas, SL; Marzec-Calvert, R; Stewart, JM; Vavrek, RJ, 1990
)
0.28
" The inhibitory effect of cilostazol on platelet aggregation was potentiated by the presence of endothelial cells, and the slope of the dose-response curves were identified to be as the same between both experiments in the presence and the absence of endothelial cells."( Potentiation of anti-platelet aggregating activity of cilostazol with vascular endothelial cells.
Chijiwa, T; Igawa, T; Kato, S; Kawamura, K; Kimura, Y; Shimidzu, S; Shiragiku, T; Tani, T; Unemi, F, 1990
)
0.28
" It showed that a larger dosage of CP, which could inhibited the synthesis of both TXA2 and PGI2, its mechanism of action needs further study."( [Effects of Codonopsis pilosulae on the synthesis of thromboxane A2 and prostacyclin].
Wang, S; Zhu, G, 1990
)
0.28
" Cumulative dose-response curves of the alpha 1-agonists l-phenylephrine or cirazoline applied luminally in rat tail arteries and in side branches of canine femoral arteries were identical to those obtained by adventitial application in the intact arteries, and were not modified by removal of the endothelium (eliminating acetylcholine-induced dilations)."( Endothelium-mediated dilations contribute to the polarity of the arterial wall in vasomotion induced by alpha 2-adrenergic agonists.
Busse, R; Holtz, J; Kuon, E; Matsuda, H,
)
0.13
" CyA dosage and plasma level were similar in hypertensive and normotensive patients."( Hypertension in bone marrow transplanted patients.
De Plaen, JF; Ferrant, A; Michaux, JL; van Ypersele de Strihou, C, 1989
)
0.28
"Eight patients with chronic heart failure classified as NYHA class II to III (group 1) and nine patients with acute decompensated heart failure classified as NYHA class IV (group 2) were treated with piretanide at a dosage of 12 mg administered intravenously."( [Piretanide in chronic and acute decompensated heart failure. Effect on hemodynamics and vasoactive hormones].
Hopf, R; Kaltenbach, M; Kirsten, R; Nelson, K; Pooth, R; Sievert, H; Vens-Cappell, F, 1989
)
0.28
" In aortic thrombus formation in rabbits, the platelet 5-HT release reaction and platelet destruction could be reduced by the compound, meanwhile aortic thrombosis was inhibited with a clear correlation between drug dosage and its efficacy."( [Inhibitory effects of new-breviscapine on thrombosis in vivo].
Wang, ZY, 1989
)
0.28
" During long-term dosing with the synthetic inhibitor, inhibition of thromboxane biosynthesis was incomplete, which would permit continued thromboxane-dependent platelet aggregation to occur."( Increased thromboxane biosynthesis in a human preparation of platelet activation: biochemical and functional consequences of selective inhibition of thromboxane synthase.
Doran, JB; FitzGerald, GA; Reilly, IA; Smith, B, 1986
)
0.27
"The effect of 7 consecutive days dosing with anti-inflammatory drugs on rat gastric mucosal PGE2 and 6-keto-PGF1 alpha concentrations were studied."( A subchronic study of the effect of etodolac on the gastric mucosal prostaglandin levels in the rat.
Cohen, R; Gilliar, J; Lee, DK; Mulder, B; Smith, T, 1986
)
0.27
" A dose-response curve was achieved for all three cyclooxygenase products with the calcium ionophore A23187."( Human peritoneal eosinophils and formation of arachidonate cyclooxygenase products.
Foegh, ML; Maddox, YT; Ramwell, PW, 1986
)
0.27
"OH) radical was observed to affect cyclooxygenase metabolism in a dose-response manner."( Gender-related variations and interaction of human neutrophil cyclooxygenase and oxidative burst metabolites.
Bellanti, JA; Mallery, SR; Ramwell, PW; Zeligs, BJ, 1986
)
0.27
" Isolated rings (circular preparations) obtained from rat thoracic aortae responded to increasing concentrations of NE with dose-dependent tonic enhancement, not significantly affected by the presence of indomethacin (10(-6)M); whereas, preincubation with phentolamine (10(-6)M), yohimbine (10(-7)M) or prazosin (10(-8)M), shifted significantly to the right points of the positive inotropic dose-response curve for NE."( Possible prostacyclin involvement on disparate tonic responses to "in vitro" norepinephrine in circular and in longitudinal preparations from rat thoracic aorta.
Chaud, M; Franchi, AM; Gimeno, AL; Gimeno, MA, 1987
)
0.27
" Here we report on a study including 41 patients with peripheral arterial disease and/or coronary heart disease before treatment and after receiving ASA in an individually controlled dosage regimen."( Individually controlled acetylsalicyclic acid (ASA) in the long-term treatment of patients with arteriosclerosis.
Heine, H; Misselwitz, F; Norden, C, 1988
)
0.27
" The importance of the findings for the clinical efficacy of this dosage schedule is considered."( Effects of a phenylbutazone paste in ponies: model of acute nonimmune inflammation.
Higgins, AJ; Lees, P, 1986
)
0.27
" TxB2 generation was inhibited with a dose-response curve, 2 microM being the lowest dazmegrel concentration giving 100% inhibition."( Dissociation between thromboxane generation and metastatic potential in cells from a murine fibrosarcoma. Studies with a selective thromboxane synthase inhibitor.
Bolognese Dalessandro, AP; de Gaetano, G; Donati, MB; Lampugnani, MG; Niewiarowska, A; Vicenzi, E, 1987
)
0.27
" In addition to these present results, AR 12463 reduced significantly the mean arterial blood pressure of spontaneously hypertensive rats (at a dosage of 20 mg/kg/d administered orally for 2 weeks) in contrast to the same dosage of trapidil."( [The effect of trapidil and the trapidil derivative AR 12463 on blood pressure and thromboxane formation in spontaneously hypertensive rats].
Mest, HJ; Steinborn, C; Taube, C, 1987
)
0.27
" Blood samples were drawn 0, 2, 4, and 6 hours and 7 days after dosing for determination in serum (from untreated or in vitro indomethacin-treated portions of the blood) of TxA2 and PGI2 by radioimmunoassay of their stable metabolites (TxB2 and 6-keto-PGF1 alpha)."( Kinetics of ibuprofen effect on platelet and endothelial prostanoid release.
Beyers, BJ; Bowen, RJ; Longenecker, GL; Shah, AK; Swift, IA, 1985
)
0.27
" Dose-response curves for purinergic stimulation of PGI2 release showed that ADP was equipotent with ATP, while AMP and adenosine were virtually inactive."( Purinoceptor mediated stimulation of prostacyclin release in the porcine pulmonary vasculature.
Hellewell, PG; Pearson, JD, 1984
)
0.27
" The daily dosage ceiling was increased to 10 mg."( Some biochemical correlates of panic attacks with agoraphobia and their response to a new treatment.
Coleman, JH; Greenblatt, DJ; Jones, KJ; Levine, PH; Orsulak, PJ; Peterson, M; Schildkraut, JJ; Sheehan, DV; Uzogara, E; Watkins, D, 1984
)
0.27
" Thus, intravenous PGI2 to a dosage of 10 ng/kg/min is a safe and effective systemic, pulmonary and coronary arterial vasodilator in patients with CAD and stable angina pectoris."( Hemodynamic effects of intravenous prostacyclin in stable angina pectoris.
Campbell, WB; Firth, BG; Hillis, LD; Winniford, MD, 1983
)
0.27
" However, we cannot exclude the possibility that intermittent bolus-like dosing of nicotine from cigarettes could have different effects from those produced by continually released transdermal nicotine."( Nicotine effects on eicosanoid formation and hemostatic function: comparison of transdermal nicotine and cigarette smoking.
Benowitz, NL; Fitzgerald, GA; Wilson, M; Zhang, Q, 1993
)
0.29
"01) suggest that a hypercoagulable state persists in low dosage OC users."( Large increase in plasmatic 11-dehydro-TxB2 levels due to oral contraceptives.
Donnez, J; Grandjean, P; Lavenne, E; Schlit, AF, 1995
)
0.29
" Increases in perfusion pressure in response to bolus injections of U46619 were used to construct dose-response curves."( Reduced thromboxane receptor affinity and vasoconstrictor responses in placentae from diabetic pregnancies.
Hollander, AM; Mento, PF; Wilkes, BM, 1994
)
0.29
" Dose-response curves, the hemodynamic effects of prostacyclin (20 micrograms/kg) and its inhibitor indomethacin and measurements of plasma and urinary levels of 6-keto-prostaglandin F1 alpha were compared in three groups of six rats each: normal, with portal vein stenosis and with secondary biliary cirrhosis."( Role of prostacyclin in hemodynamic alterations in conscious rats with extrahepatic or intrahepatic portal hypertension.
Cailmail, S; Lebrec, D; Moreau, R; Oberti, F; Pipy, B; Sogni, P, 1993
)
0.29
"We compared the effect of different aspirin schedules, dosages, and formulations on various bleeding time parameters including bleeding time, plasma and total blood volume, and levels of the stable metabolites of thromboxane A2 (TXA2) and prostacyclin (PGI2) (respectively, TXB2 and 6-keto-prostaglandin F1 alpha (6-keto-PGF1 alpha)) to determine the optimal dosage and formulation of aspirin to inhibit TXA2 production while sparing PGI2."( The effect of regular and enteric-coated aspirin on bleeding time, thromboxane, and prostacyclin.
Ebbeling, L; Gerrard, JM; Gow, JA, 1993
)
0.29
" The dose-response relationship of indomethacin for inhibition of prostaglandin formation and rebamipide-induced protection correlated well and 5 mg/kg indomethacin completely prevented the protective effect of rebamipide."( Stimulation of prostaglandin biosynthesis mediates gastroprotective effect of rebamipide in rats.
Kleine, A; Kluge, S; Peskar, BM, 1993
)
0.29
" The optimal dose remains uncertain, but the initial dosage of 40-60 micrograms/day given in three to four doses for adult patients is considered to be acceptable."( [Short- and long-term effects of the new oral prostacyclin analogue, beraprost sodium, in patients with severe pulmonary hypertension].
Hashiguchi, R; Matsuo, N; Matsuura, H; Morishita, T; Muto, H; Nakayama, T; Ozawa, Y; Saito, T; Saji, T; Yamazaki, J, 1996
)
0.29
" The effects of four days' dosing of a selective thromboxane A2 (TXA2) synthetase inhibitor, DP-1904 (DP), on prostanoid metabolism, were also studied."( Abnormal prostanoid metabolism in lupus nephritis and the effects of a thromboxane A2 synthetase inhibitor, DP-1904.
Homma, M; Ichikawa, Y; Tojo, T; Yoshida, T, 1996
)
0.29
" Although its ability to inhibit the cyclooxygenase pathway was readily observed in whole blood and in vivo, tenidap's 5-LO blockade could not be demonstrated by ionophore stimulated human blood, nor after oral dosing in rat models in which peritoneal leukotriene products were measured after challenge with three different stimuli."( Tenidap inhibits 5-lipoxygenase product formation in vitro, but this activity is not observed in three animal models.
Carty, TJ; Cheng, JD; Ernest, MJ; Eskra, JD; Griffiths, RJ; Joseph, PA; Kadin, SB; Loose, LD; Moore, PF; Murase, S; Nagahisa, A; Pazoles, PP; Pillar, JS; Sweeney, FJ, 1997
)
0.3
"To observe the pathological changes of liver sinusoidal endothelial cells, the regional perfusion with different dosage of 5-FU was performed by using modified rat's model of ILP."( [The injury of liver sinusoidal endothelial cells in a rat's isolated liver perfusion (ILP) model for regional chemotherapy].
Xia, S; Xing, X, 1996
)
0.29
" In contrast, repeated dosing (7 days) with ridogrel (3 to 25 mg/kg/day), had an antihypertensive effect in 12-week-old stroke-prone spontaneously hypertensive rats."( Effects of ridogrel, a thromboxane synthase inhibitor and receptor antagonist, on blood pressure in the spontaneously hypertensive rat.
Quest, DW; Wilson, TW, 1998
)
0.3
" These findings suggest that, following ocular trauma, temporal changes occur in ICB PG synthetic activity that may impact on the selection of an optimal dosing paradigm for efficacy testing of topically administered NSAIDs."( Transient loss of prostaglandin synthetic capacity in rabbit iris-ciliary body following anterior chamber paracentesis.
Brady, MT; Gamache, DA; Graff, G; Spellman, JM; Yanni, JM, 1998
)
0.3
" In study 1, AA-2414 + Px produced a dose-response inhibition of Px-induced increases in perfusion pressure, vascular resistance, and maternal secretion of lipid peroxides and TXB2."( AA-2414, an antioxidant and thromboxane receptor blocker, completely inhibits peroxide-induced vasoconstriction in the human placenta.
Killian, A; Walsh, SW; Wang, Y, 1999
)
0.3
"This study was carried out to determine the efficacy of and dose-response relationships to inhaled aerosolized prostacyclin (IAP), when used as a selective pulmonary vasodilator (SPV) in patients with severe hypoxemia due to ARDS."( Dose-response to inhaled aerosolized prostacyclin for hypoxemia due to ARDS.
Barden, A; Bulsara, MK; Michalopoulos, N; Roberts, BL; van Heerden, PV, 2000
)
0.31
" To address this hypothesis, we used dosing with nimesulide, which inhibited COX-2 ex vivo, depressed urinary 2,3 dinor 6-keto PGF(1alpha) by approximately 60% but had no effect on thromboxane formation by platelets, which only express COX-1."( Acceleration of atherogenesis by COX-1-dependent prostanoid formation in low density lipoprotein receptor knockout mice.
FitzGerald, GA; Li, H; Praticò, D; Tillmann, C; Zhang, ZB, 2001
)
0.31
"Clearances of inulin and PAH decreased progressively after CsA dosage while renal vascular resistance increased."( Pathophysiology of cyclosporine-induced nephrotoxicity in humans: a role for nitric oxide?
Bernemann, A; Bickeböller, R; Gossmann, J; Raab, HP; Radounikli, A; Schellinski, O; Scheuermann, EH, 2001
)
0.31
" Moreover, effects of ridogrel (RID, an antagonist of TxA 2/PGH2 receptors and inhibitor of thromboxane synthetase) were analysed by cumulative dose-response curves to SER in the presence and in the absence of the NO synthase inhibitor N(omega)-nitro-L-arginine (NOLA)."( Serotonin hypersensitivity in aorta of two kidney-two clip hypertensive rats: calcium contribution and prostanoids-nitric oxide interactions.
Celentano, MM; Damiano, PF; de la Riva, IJ; Puyó, AM; Rosón, MI; Speziale, E; Vega, GW, 2001
)
0.31
" Our studies with RIA showed that: at the dosage of inhibiting platelet aggregation, ASAA was found to inhibit the formation of cyclooxygenase pathway metabolites TXB2 in platelets."( [Effects of acetylsalvianolic acid A on arachidonic acid metabolism in platelets].
Xu, L; Yu, W, 1998
)
0.3
" The binding properties of 6-keto-prostaglandin F1alpha toward its antibody and the bioluminescent properties of aequorin were retained in the conjugate, which was then used to generate a dose-response curve for the analyte in a convenient microtiter plate format."( Determination of prostacyclin in plasma through a bioluminescent immunoassay for 6-keto-prostaglandin F1alpha: implication of dosage in patients with primary pulmonary hypertension.
Daunert, S; Deo, SK; Desai, UA; Hyland, KV; Poon, M, 2002
)
0.31
" A portal perfusion pressure dose-response curve to methoxamine was performed in control and cirrhotic rat livers preincubated with vehicle, the nitric oxide synthase blocker N(G)-nitro-L-arginine (L-NNA), indomethacin cyclooxygenase (COX) inhibitor, L-NNA + indomethacin, or the thromboxane (TX) A(2) receptor blocker SQ 29,548."( Cyclooxygenase-derived products modulate the increased intrahepatic resistance of cirrhotic rat livers.
Abraldes, JG; Bosch, J; Bragulat, M; Corominola, H; García-Pagán, JC; Graupera, M; Peralta, C; Rodés, J, 2003
)
0.32
"3% (mean+/-SD), respectively, and of the urinary excretion of 11-dehydro-TXB2, an index of systemic biosynthesis of TXA2 in vivo, by 85+/-8% and 78+/-7%, respectively, that persisted throughout the dosing interval."( Clinical pharmacology of platelet, monocyte, and vascular cyclooxygenase inhibition by naproxen and low-dose aspirin in healthy subjects.
Capone, ML; Di Gregorio, P; Grana, M; Merciaro, G; Minuz, P; Patrignani, P; Patrono, C; Ricciotti, E; Sciulli, MG; Tacconelli, S, 2004
)
0.32
" BQ123 (1 microm) caused a rightward shift in the ET-1 dose-response curve, while indomethacin at a threshold concentration (28 nm) tended to have an opposite effect."( Endothelin-induced constriction of the ductus venosus in fetal sheep: developmental aspects and possible interaction with vasodilatory prostaglandin.
Adeagbo, AS; Coceani, F; Kelsey, L, 2004
)
0.32
" Efficacy of medicine in groups with high dosage was stronger than those with low dosage."( [Physiological effects of cold and cool Chinese herbal medicine of channel tropism of stomach on rats with stomach-heat syndrome].
Guo, BJ; Li, XE; Li, XM; Liu, JZ; Sun, GB, 2007
)
0.34
" Platelet aggregation induced by ADP and dosing of prostanoid products 6-keto-PGF1alpha, TXB2, PGE2 and LTB4 were also performed."( Modifications produced by selective inhibitors of cyclooxygenase and ultra low dose aspirin on platelet activity in portal hypertension.
Aguejouf, O; Belon, P; Desplat, V; Doutremepuich, C; Eizayaga, FX, 2007
)
0.34
"This multicenter, double-blind, randomized, placebo-controlled, parallel-group study assessed renal function during dosing with etoricoxib 90 mg daily, celecoxib 200 mg twice daily, and naproxen 500 mg twice daily."( Effects of etoricoxib and comparator nonsteroidal anti-inflammatory drugs on urinary sodium excretion, blood pressure, and other renal function indicators in elderly subjects consuming a controlled sodium diet.
Gertz, BJ; Gottesdiener, KM; Hilliard, DA; Hreniuk, D; Lasseter, KC; Miller, J; Schwartz, JI; Snyder, KM; Thach, C, 2007
)
0.34
" A dose-response profile revealed a noncompetitive property of VRQ397; correspondingly, VRQ397 bound specifically to V2R-expressing cells could not displace its natural ligand, AVP, but modulated AVP binding kinetics (dissociation rate)."( VRQ397 (CRAVKY): a novel noncompetitive V2 receptor antagonist.
Beauregard, K; Bouvier, M; Brault, S; Chemtob, S; Duhamel, F; Gobeil, F; Guillon, G; Hamdan, FF; Hamel, D; Hardy, P; Heveker, N; Hou, X; Joyal, JS; Kaul, R; Lahaie, I; Lubell, WD; Nedev, H; Quiniou, C; Rihakova, L; Sapieha, P; Saragovi, HU; Shao, Z, 2009
)
0.35
" A twice daily (bid) dosing is necessary to fully inhibit TXA2."( In vivo prostacyclin biosynthesis and effects of different aspirin regimens in patients with essential thrombocythaemia.
Barbieri, SS; Cavalca, V; Dragani, A; Pagliaccia, F; Patrono, C; Porro, B; Rocca, B; Squellerio, I; Tremoli, E; Veglia, F, 2014
)
0.4
" Twenty four hours ERPF and GFR estimated by para-aminohippurate and sinistrin clearance were performed at baseline and at the end of each 10-day dosing period."( A randomized cross-over comparison of short-term exposure of once-daily extended release tacrolimus and twice-daily tacrolimus on renal function in healthy volunteers.
Cherney, DZ; Lai, V; Moon, KH; Schulz, MZ; Zaltzman, JS, 2014
)
0.4
" Peak inhibition of urinary metabolite excretion across 8 hours following dosing was the primary end point."( Inhibition of prostacyclin and thromboxane biosynthesis in healthy volunteers by single and multiple doses of acetaminophen and indomethacin.
Gottesdiener, KM; Greenberg, HE; Mehta, A; Musser, BJ; Schwartz, JI; Taggart, WV; Tanaka, WK, 2015
)
0.42
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (2)

RoleDescription
human metaboliteAny mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
mouse metaboliteAny mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Drug Classes (1)

ClassDescription
prostaglandins Falpha
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Pathways (48)

PathwayProteinsCompounds
Metabolism14961108
Metabolism of lipids500463
Fatty acid metabolism113203
Arachidonic acid metabolism3682
Synthesis of Prostaglandins (PG) and Thromboxanes (TX)1135
Arachidonic Acid Metabolism2966
Leukotriene C4 Synthesis Deficiency2966
Piroxicam Action Pathway2967
Acetylsalicylic Acid Action Pathway2967
Etodolac Action Pathway2967
Ketoprofen Action Pathway2967
Ibuprofen Action Pathway5076
Rofecoxib Action Pathway2967
Diclofenac Action Pathway2967
Sulindac Action Pathway2967
Celecoxib Action Pathway3573
Ketorolac Action Pathway2967
Suprofen Action Pathway2967
Bromfenac Action Pathway2967
Indomethacin Action Pathway3067
Mefenamic Acid Action Pathway2967
Oxaprozin Action Pathway2967
Nabumetone Action Pathway2967
Naproxen Action Pathway2967
Diflunisal Action Pathway2967
Meloxicam Action Pathway2967
Valdecoxib Action Pathway2967
Antipyrine Action Pathway2967
Antrafenine Action Pathway2967
Carprofen Action Pathway2967
Etoricoxib Action Pathway2967
Fenoprofen Action Pathway2967
Flurbiprofen Action Pathway2967
Magnesium Salicylate Action Pathway2967
Lumiracoxib Action Pathway2967
Lornoxicam Action Pathway2967
Phenylbutazone Action Pathway2967
Nepafenac Action Pathway2967
Trisalicylate-Choline Action Pathway2967
Tolmetin Action Pathway2967
Tiaprofenic Acid Action Pathway2967
Tenoxicam Action Pathway2967
Salsalate Action Pathway2967
Salicylate-Sodium Action Pathway2967
Salicylic Acid Action Pathway2967
Acetaminophen Action Pathway2967
Eicosanoid metabolism via cyclooxygenases (COX)137
Arachidonic acid (AA, ARA) oxylipin metabolism076
Arachidonic acid metabolism via COX (Cyclooxygenase) pathway035

Protein Targets (1)

Other Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Solute carrier organic anion transporter family member 2A1Rattus norvegicus (Norway rat)Km7.56900.07001.65207.5690AID681576
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (5)

Assay IDTitleYearJournalArticle
AID1347154Primary screen GU AMC qHTS for Zika virus inhibitors2020Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49
Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors.
AID1508630Primary qHTS for small molecule stabilizers of the endoplasmic reticulum resident proteome: Secreted ER Calcium Modulated Protein (SERCaMP) assay2021Cell reports, 04-27, Volume: 35, Issue:4
A target-agnostic screen identifies approved drugs to stabilize the endoplasmic reticulum-resident proteome.
AID588519A screen for compounds that inhibit viral RNA polymerase binding and polymerization activities2011Antiviral research, Sep, Volume: 91, Issue:3
High-throughput screening identification of poliovirus RNA-dependent RNA polymerase inhibitors.
AID540299A screen for compounds that inhibit the MenB enzyme of Mycobacterium tuberculosis2010Bioorganic & medicinal chemistry letters, Nov-01, Volume: 20, Issue:21
Synthesis and SAR studies of 1,4-benzoxazine MenB inhibitors: novel antibacterial agents against Mycobacterium tuberculosis.
AID681576TP_TRANSPORTER: uptake in PGT-expressing HeLa cells1995Science (New York, N.Y.), May-12, Volume: 268, Issue:5212
Identification and characterization of a prostaglandin transporter.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (4,651)

TimeframeStudies, This Drug (%)All Drugs %
pre-19902277 (48.96)18.7374
1990's1693 (36.40)18.2507
2000's509 (10.94)29.6817
2010's158 (3.40)24.3611
2020's14 (0.30)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.20

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index12.20 (24.57)
Research Supply Index8.54 (2.92)
Research Growth Index4.12 (4.65)
Search Engine Demand Index10.37 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (12.20)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials294 (6.08%)5.53%
Reviews31 (0.64%)6.00%
Case Studies20 (0.41%)4.05%
Observational0 (0.00%)0.25%
Other4,487 (92.86%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]