Dihomo-γ-linolenic acid: Difference between revisions

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			{{redirect\|DGLA\|the algebra\|Differential graded Lie algebra}}
	{{chembox		{{chembox
			\| Watchedfields = changed
			\| verifiedrevid = 291015519
	\| Name = Dihomo-γ-linolenic acid		\| Name = Dihomo-γ-linolenic acid
	\| ImageFile = DGLAnumbering.png		\| ImageFile = DGLAnumbering.png
	\| ImageSize = 250px		\| ImageSize = 250px
	\| ImageName = Dihomo-gamma linolenic acid		\| ImageName = Dihomo-gamma linolenic acid
	\| ~~OtherNames~~ = ''~~cis~~'',''~~cis~~'',''~~cis~~''-8,11,14-~~Eicosatrienoic~~ acid~~<br>DGLA~~		\| PIN = (8''Z'',11''Z'',14''Z'')-Icosa-8,11,14-trienoic acid
			\| OtherNames = ''cis'',''cis'',''cis''-8,11,14-Eicosatrienoic acid; DGLA; Diroleuton ({{abbrlink\|INN\|International Nonproprietary Name}})
	\| Section1 = {{Chembox Identifiers		\| Section1 = {{Chembox Identifiers
	\| CASNo=1783-84-2		\| CASNo=1783-84-2
	\| PubChem=5280581		\| PubChem=5280581
	\| SMILES = ~~{{SMILES\|S=CCCCCC=CCC=CCC=CCCCCCCC(=O)O}} (canonical)<br />{{SMILES\|S=~~CCCCC\C=C/C\C=C/C\C=C/CCCCCCC(=O)O~~}} (isomeric)~~		\| SMILES = CCCCC\C=C/C\C=C/C\C=C/CCCCCCC(=O)O
			\| UNII_Ref = {{fdacite\|correct\|FDA}}
			\| UNII = FC398RK06S\| ChemSpiderID = 4444199
			\| InChI = 1/C20H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h6-7,9-10,12-13H,2-5,8,11,14-19H2,1H3,(H,21,22)/b7-6-,10-9-,13-12-
			\| InChIKey = HOBAELRKJCKHQD-QNEBEIHSBE
			\| StdInChI = 1S/C20H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h6-7,9-10,12-13H,2-5,8,11,14-19H2,1H3,(H,21,22)/b7-6-,10-9-,13-12-
			\| StdInChIKey = HOBAELRKJCKHQD-QNEBEIHSSA-N
	}}		}}
	\| Section2 = {{Chembox Properties		\| Section2 = {{Chembox Properties
	\| ~~Formula =~~ C~~<sub>~~20~~</sub>~~H~~<sub>~~34~~</sub>~~O~~<sub>~~2~~</sub>~~		\| C=20\|H=34\|O=2
		⚫	\| MeltingPt =
	\| MolarMass = 306.483 g/]
⚫	\| MeltingPt =
	}}		}}
	}}		}}

	'''Dihomo-γ-linolenic acid''' ('''DGLA''') is a 20-carbon ]. In physiological literature, it is given the name 20:3 (ω−6). ~~Chemically,~~ DGLA is a ] with a 20-carbon chain and three '']'' double bonds; the first double bond is located at the sixth carbon from the omega end. DGLA is the elongation product of ] (GLA; 18:3, ω−6). GLA, in turn, is a desaturation product of ] (18:2, ω−6).		'''Dihomo-γ-linolenic acid''' ('''DGLA''') is a 20-carbon ] (also called, cis,cis,cis-8,11,14-eicosatrienoic acid). In physiological literature, it is given the name 20:3 (ω−6). DGLA is a ] with a 20-carbon chain and three '']'' double bonds; the first double bond is located at the sixth carbon from the omega end. DGLA is the elongation product of ] (GLA; 18:3, ω−6). GLA, in turn, is a desaturation product (]) of ] (18:2, ω−6). DGLA is made in the body by the elongation of GLA, by an efficient enzyme which does not appear to suffer any form of (dietary) inhibition. DGLA is an extremely uncommon fatty acid, found only in trace amounts in animal products.<ref>Horrobin, D. F., 1990a.
			Gamma linolenic acid.
			Rev. Contemp. Pharmacother. 1, 1-45</ref><ref>Huang, Y.-S. and Mills, D. E. (Eds.), 1996.
			Gamma-linolenic acid metabolism and its roles in nutrition and medicine.
			AOCS Press, Champaign, Illinois, 319 pp.</ref>

	== Biological effects==		== Biological effects==
	The ] metabolites of DGLA are:		The ] metabolites of DGLA are:
	* Series-1 ]s (thromboxanes with 1 double-bond), via the ] pathways.		* Series-1 ]s (thromboxanes with 1 double-bond), via the ] pathways.
	* Series-1 ]s, via the COX-1 and COX-2 pathways.<ref>{{cite journal \| ~~author~~=Fan, Yang-Yi ~~and~~ Robert S. ~~Chapkin~~ \| title=Importance of Dietary γ-Linolenic Acid in Human Health and Nutrition ~~\| url=http://jn.nutrition.org/cgi/content/full/128/9/1411~~ \| date= ] ~~] \| accessdate= 2007-10-16~~ \| journal =Journal of Nutrition \| volume = 128 \|issue = 9 \|pages = ~~1411–1414~~ \| pmid=9732298 \| ~~month~~=~~Sep~~ \| ~~day~~=01}}</ref>		* Series-1 ]s, via the COX-1 and COX-2 pathways.<ref>{{cite journal \|author1=Fan, Yang-Yi \|author2=Chapkin, Robert S. \| title=Importance of Dietary γ-Linolenic Acid in Human Health and Nutrition \| date=9 September 1998 \| journal=Journal of Nutrition \| volume=128 \| issue=9 \| pages=1411–4 \| pmid=9732298 \| doi=10.1093/jn/128.9.1411 \| doi-access=free}}</ref>
	* A 15-hydroxyl derivative that blocks the transformation of ] to ]s.<ref>{{cite ~~web~~\| ~~author~~= Belch, Jill JF ~~and~~ ~~Alexander~~ ~~Hill~~\| title=Evening primrose oil and borage oil in rheumatologic conditions\|~~month~~=~~January~~ \| ~~year~~=2000\| ~~url~~= ~~http://www~~.ajcn~~.org/cgi/content/full~~/71/1/352S\|~~accessdate~~=~~February~~ 12\|~~accessyear~~=~~2006~~}}</ref>		* A 15-hydroxyl derivative that blocks the transformation of ] to ]s.<ref>{{cite journal \|author1=Belch, Jill J.F. \|author-link=Jill Belch \|author2=Hill, Alexander \|title=Evening primrose oil and borage oil in rheumatologic conditions \|journal=The American Journal of Clinical Nutrition \|date=January 2000 \|volume=71 \|issue=1 Suppl \|pages=352S–6S \|doi=10.1093/ajcn/71.1.352S \|pmid=10617996 \|doi-access=free }}</ref>

	All of these effects are anti-inflammatory. This is in marked contrast with the analogous metabolites of ] (AA) which are the series-2 thromboxanes and prostanoids and the series-4 leukotrienes. In addition to yielding anti-inflammatory eicosanoids, DGLA ] with AA for COX and lipoxygenase, inhibiting the production of AA's eicosanoids.		All of these effects are anti-inflammatory. This is in marked contrast with the analogous metabolites of ] (AA), which are the series-2 thromboxanes and prostanoids and the series-4 leukotrienes. In addition to yielding anti-inflammatory eicosanoids, DGLA ] with AA for COX and lipoxygenase, inhibiting the production of AA's eicosanoids.

	Taken orally in a small study, DGLA produced antithrombotic effects.<ref name="pmid338112">{{cite journal		Taken orally in a small study, DGLA produced ] effects.<ref name="pmid338112">{{cite journal
	\|~~author~~=Kernoff PB, Willis AL, Stone KJ, Davies JA, McNicol GP		\|vauthors=Kernoff PB, Willis AL, Stone KJ, Davies JA, McNicol GP \|title=Antithrombotic potential of dihomo-γ-linolenic acid in man
		⚫	\|journal=British Medical Journal
	\|title=Antithrombotic potential of dihomo-γ-linolenic acid in man
⚫	\|journal=British ~~medical~~ ~~journal~~
	\|volume=2		\|volume=2
	\|issue=6100		\|issue=6100
	\|pages=~~1441–4~~		\|pages=1441–1444
	\|year=1977		\|year=1977
	\|pmid=338112		\|pmid=338112
			\|doi=10.1136/bmj.2.6100.1441
			\|pmc=1632618
	}}</ref> Supplementing dietary GLA increases serum DGLA, as well as serum AA levels.<ref name="pmid9237935">{{cite journal		}}</ref> Supplementing dietary GLA increases serum DGLA, as well as serum AA levels.<ref name="pmid9237935">{{cite journal
	\|author=Johnson MM~~, Swan DD, Surette ME, ''et al.''~~		\|author=Johnson MM
	\|title=Dietary supplementation with γ-linolenic acid alters fatty acid content and eicosanoid production in healthy humans		\|title=Dietary supplementation with γ-linolenic acid alters fatty acid content and eicosanoid production in healthy humans
	\|journal=J. Nutr.		\|journal=J. Nutr.
Line 45:		Line 59:
	\|year=1997		\|year=1997
	\|pmid=9237935		\|pmid=9237935
			\|name-list-style=vanc\|author2=Swan DD
			\|author3=Surette ME
			\|display-authors=3
			\|last4=Stegner
			\|first4=J
			\|last5=Chilton
			\|first5=T
			\|last6=Fonteh
			\|first6=AN
			\|last7=Chilton
			\|first7=FH
			\|doi=10.1093/jn/127.8.1435
			\|doi-access=free
	}}</ref> Cosupplementation with GLA and EPA lowers serum AA levels by blocking Δ-5-desaturase activity, while also lowering leukotriene synthesis in neutrophils.<ref name="pmid10917903">{{cite journal		}}</ref> Cosupplementation with GLA and EPA lowers serum AA levels by blocking Δ-5-desaturase activity, while also lowering leukotriene synthesis in neutrophils.<ref name="pmid10917903">{{cite journal
	\|~~author~~=Barham JB, Edens MB, Fonteh AN, Johnson MM, Easter L, Chilton FH		\|vauthors=Barham JB, Edens MB, Fonteh AN, Johnson MM, Easter L, Chilton FH \|title=Addition of eicosapentaenoic acid to gamma-linolenic acid-supplemented diets prevents serum arachidonic acid accumulation in humans
	\|title=Addition of eicosapentaenoic acid to gamma-linolenic acid-supplemented diets prevents serum arachidonic acid accumulation in humans
	\|journal=J. Nutr.		\|journal=J. Nutr.
	\|volume=130		\|volume=130
	\|issue=8		\|issue=8
	\|pages=1925–31		\|pages=1925–31
	\|~~year~~=2000		\|date=August 2000
			\|doi=10.1093/jn/130.8.1925
	\|month=August
	\|pmid=10917903		\|pmid=10917903
			\|doi-access=free
	}}</ref>		}}</ref>

	] is a rich source of γ-linolenic acid—the dietary precursor to DGLA.]]		] is a rich source of γ-linolenic acid—the dietary precursor to DGLA.]]

			== See also ==
			* ]

	==References==		==References==
	{{~~reflist~~}}		{{Reflist}}

	{{Fatty acids}}		{{Fatty acids}}
			{{Prostanoidergics}}
			{{Leukotrienergics}}

			{{DEFAULTSORT:Dihomo-gamma-linolenic acid}}
⚫	]
	]		]
		⚫	]


	{{biochem-stub}}

	]
	]

Latest revision as of 01:53, 19 July 2024

"DGLA" redirects here. For the algebra, see Differential graded Lie algebra.

Dihomo-γ-linolenic acid
Names

Preferred IUPAC name (8Z,11Z,14Z)-Icosa-8,11,14-trienoic acid
Other names cis,cis,cis-8,11,14-Eicosatrienoic acid; DGLA; Diroleuton (INNTooltip International Nonproprietary Name)
Identifiers
CAS Number	1783-84-2
3D model (JSmol)	Interactive image
ChemSpider	4444199
ECHA InfoCard	100.015.667
PubChem CID	5280581
UNII	FC398RK06S
CompTox Dashboard (EPA)	DTXSID00912351
InChI InChI=1S/C20H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h6-7,9-10,12-13H,2-5,8,11,14-19H2,1H3,(H,21,22)/b7-6-,10-9-,13-12-Key: HOBAELRKJCKHQD-QNEBEIHSSA-N InChI=1/C20H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h6-7,9-10,12-13H,2-5,8,11,14-19H2,1H3,(H,21,22)/b7-6-,10-9-,13-12-Key: HOBAELRKJCKHQD-QNEBEIHSBE
SMILES CCCCC\C=C/C\C=C/C\C=C/CCCCCCC(=O)O
Properties
Chemical formula	C₂₀H₃₄O₂
Molar mass	306.490 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Y verify (what is ?) Infobox references

Chemical compound

Dihomo-γ-linolenic acid (DGLA) is a 20-carbon ω−6 fatty acid (also called, cis,cis,cis-8,11,14-eicosatrienoic acid). In physiological literature, it is given the name 20:3 (ω−6). DGLA is a carboxylic acid with a 20-carbon chain and three cis double bonds; the first double bond is located at the sixth carbon from the omega end. DGLA is the elongation product of γ-linolenic acid (GLA; 18:3, ω−6). GLA, in turn, is a desaturation product (Delta 6 desaturase) of linoleic acid (18:2, ω−6). DGLA is made in the body by the elongation of GLA, by an efficient enzyme which does not appear to suffer any form of (dietary) inhibition. DGLA is an extremely uncommon fatty acid, found only in trace amounts in animal products.

Biological effects

The eicosanoid metabolites of DGLA are:

Series-1 thromboxanes (thromboxanes with 1 double-bond), via the COX-1 and COX-2 pathways.
Series-1 prostanoids, via the COX-1 and COX-2 pathways.
A 15-hydroxyl derivative that blocks the transformation of arachidonic acid to leukotrienes.

All of these effects are anti-inflammatory. This is in marked contrast with the analogous metabolites of arachidonic acid (AA), which are the series-2 thromboxanes and prostanoids and the series-4 leukotrienes. In addition to yielding anti-inflammatory eicosanoids, DGLA competes with AA for COX and lipoxygenase, inhibiting the production of AA's eicosanoids.

Taken orally in a small study, DGLA produced antithrombotic effects. Supplementing dietary GLA increases serum DGLA, as well as serum AA levels. Cosupplementation with GLA and EPA lowers serum AA levels by blocking Δ-5-desaturase activity, while also lowering leukotriene synthesis in neutrophils.

References

Horrobin, D. F., 1990a. Gamma linolenic acid. Rev. Contemp. Pharmacother. 1, 1-45
Huang, Y.-S. and Mills, D. E. (Eds.), 1996. Gamma-linolenic acid metabolism and its roles in nutrition and medicine. AOCS Press, Champaign, Illinois, 319 pp.
Fan, Yang-Yi; Chapkin, Robert S. (9 September 1998). "Importance of Dietary γ-Linolenic Acid in Human Health and Nutrition". Journal of Nutrition. 128 (9): 1411–4. doi:10.1093/jn/128.9.1411. PMID 9732298.
Belch, Jill J.F.; Hill, Alexander (January 2000). "Evening primrose oil and borage oil in rheumatologic conditions". The American Journal of Clinical Nutrition. 71 (1 Suppl): 352S – 6S. doi:10.1093/ajcn/71.1.352S. PMID 10617996.
Kernoff PB, Willis AL, Stone KJ, Davies JA, McNicol GP (1977). "Antithrombotic potential of dihomo-γ-linolenic acid in man". British Medical Journal. 2 (6100): 1441–1444. doi:10.1136/bmj.2.6100.1441. PMC 1632618. PMID 338112.
Johnson MM, Swan DD, Surette ME, et al. (1997). "Dietary supplementation with γ-linolenic acid alters fatty acid content and eicosanoid production in healthy humans". J. Nutr. 127 (8): 1435–44. doi:10.1093/jn/127.8.1435. PMID 9237935.
Barham JB, Edens MB, Fonteh AN, Johnson MM, Easter L, Chilton FH (August 2000). "Addition of eicosapentaenoic acid to gamma-linolenic acid-supplemented diets prevents serum arachidonic acid accumulation in humans". J. Nutr. 130 (8): 1925–31. doi:10.1093/jn/130.8.1925. PMID 10917903.

v t e Lipids: fatty acids
Saturated	Propionic (C3) Butyric (C4) Valeric (C5) Caproic (C6) Enanthic (C7) Caprylic (C8) Pelargonic (C9) Capric (C10) Undecylic (C11) Lauric (C12) Tridecylic (C13) Myristic (C14) Pentadecylic (C15) Palmitic (C16) Margaric (C17) Stearic (C18) Nonadecylic (C19) Arachidic (C20) Heneicosylic (C21) Behenic (C22) Tricosylic (C23) Lignoceric (C24) Pentacosylic (C25) Cerotic (C26) Carboceric (C27) Montanic (C28) Nonacosylic (C29) Melissic (C30) Hentriacontylic (C31) Lacceroic (C32) Psyllic (C33) Geddic (C34) Ceroplastic (C35) Hexatriacontylic (C36) Heptatriacontanoic (C37) Octatriacontanoic (C38) Nonatriacontanoic (C39) Tetracontanoic (C40)
ω−3 Unsaturated	Octenoic (8:1) Decenoic (10:1) Decadienoic (10:2) Lauroleic (12:1) Laurolinoleic (12:2) Myristovaccenic (14:1) Myristolinoleic (14:2) Myristolinolenic (14:3) Palmitolinolenic (16:3) Palmitidonic (16:4) α-Linolenic (18:3) Stearidonic (18:4) α-Parinaric (18:4) Dihomo-α-linolenic (20:3) Eicosatetraenoic (20:4) Eicosapentaenoic (20:5) Clupanodonic (22:5) Docosahexaenoic (22:6) 9,12,15,18,21-Tetracosapentaenoic (24:5) 6,9,12,15,18,21-Tetracosahexaenoic (24:6)
ω−5 Unsaturated	Myristoleic (14:1) Palmitovaccenic (16:1) α-Eleostearic (18:3) β-Eleostearic (trans-18:3) Punicic (18:3) 7,10,13-Octadecatrienoic (18:3) 9,12,15-Eicosatrienoic (20:3) β-Eicosatetraenoic (20:4)
ω−6 Unsaturated	8-Tetradecenoic (14:1) 12-Octadecenoic (18:1) Linoleic (18:2) Linolelaidic (trans-18:2) γ-Linolenic (18:3) Calendic (18:3) Pinolenic (18:3) Dihomo-linoleic (20:2) Dihomo-γ-linolenic (20:3) Sciadonic (20:3) Arachidonic (20:4) Adrenic (22:4) Osbond (22:5)
ω−7 Unsaturated	Palmitoleic (16:1) Vaccenic (18:1) Rumenic (18:2) Paullinic (20:1) 7,10,13-Eicosatrienoic (20:3)
ω−9 Unsaturated	Oleic (18:1) Elaidic (trans-18:1) Gondoic (20:1) Erucic (22:1) Nervonic (24:1) 8,11-Eicosadienoic (20:2) Mead (20:3)
ω−10 Unsaturated	Sapienic (16:1)
ω−11 Unsaturated	Gadoleic (20:1)
ω−12 Unsaturated	4-Hexadecenoic (16:1) Petroselinic (18:1) 8-Eicosenoic (20:1)

Prostanoid signaling modulators

Receptor
(ligands)

DP (D₂)Tooltip Prostaglandin D2 receptor

DP₁Tooltip Prostaglandin D2 receptor 1

Agonists: Prostaglandin D₂
Treprostinil

DP₂Tooltip Prostaglandin D2 receptor 2

Agonists: Indometacin
Prostaglandin D₂

EP (E₂)Tooltip Prostaglandin E2 receptor

EP₁Tooltip Prostaglandin EP1 receptor	Agonists: Beraprost Enprostil Iloprost (ciloprost) Latanoprost Lubiprostone Misoprostol Prostaglandin E₁ (alprostadil) Prostaglandin E₂ (dinoprostone) Sulprostone Antagonists: AH-6809 ONO-8130 SC-19220 SC-51089 SC-51322
EP₂Tooltip Prostaglandin EP2 receptor	Agonists: Butaprost Misoprostol Prostaglandin E₁ (alprostadil) Prostaglandin E₂ (dinoprostone) Treprostinil Antagonists: AH-6809 PF-04418948 TG 4-155
EP₃Tooltip Prostaglandin EP3 receptor	Agonists: Beraprost Carbacyclin Cicaprost Enprostil Iloprost (ciloprost) Isocarbacyclin Latanoprost Misoprostol Prostaglandin D₂ Prostaglandin E₁ (alprostadil) Prostaglandin E₂ (dinoprostone) Remiprostol Ricinoleic acid Sulprostone Antagonists: L-798106
EP₄Tooltip Prostaglandin EP4 receptor	Agonists: Lubiprostone Misoprostol Prostaglandin E₁ (alprostadil) Prostaglandin E₂ (dinoprostone) TCS-2510 Antagonists: Grapiprant GW-627368 L-161982 ONO-AE3-208
Unsorted	Agonists: 16,16-Dimethyl Prostaglandin E₂ Aganepag Carboprost Evatanepag Gemeprost Nocloprost Omidenepag Prostaglandin F_2α (dinoprost) Simenepag Taprenepag

FP (F_2α)Tooltip Prostaglandin F receptor

IP (I₂)Tooltip Prostacyclin receptor

Agonists: ACT-333679
AFP-07
Beraprost
BMY-45778
Carbacyclin
Cicaprost
Iloprost (ciloprost)
Isocarbacyclin
MRE-269
NS-304
Prostacyclin (prostaglandin I₂, epoprostenol)
Prostaglandin E₁ (alprostadil)
Ralinepag
Selexipag
Taprostene
TRA-418
Treprostinil

Antagonists: RO1138452

TP (TX_A2)Tooltip Thromboxane receptor

Agonists: Carbocyclic thromboxane A₂
I-BOP
Thromboxane A₂
U-46619
Vapiprost

Unsorted

Enzyme
(inhibitors)

COX (PTGS)	Salicylic acids: Aloxiprin Aspirin (acetylsalicylic acid) Benorilate (benorylate) Carbasalate calcium Diflunisal Dipyrocetyl Ethenzamide Guacetisal Magnesium salicylate Mesalazine (5-aminosalicylic acid) Methyl salicylate Salacetamide Salicin Salicylamide Salicylate (salicylic acid) Salsalate Sodium salicylate Triflusal; Acetic acids: Aceclofenac Acemetacin Aclofenac Amfenac Alclofenac Bendazac Bromfenac Bufexamac Bumadizone Cinmetacin Clometacin Diclofenac Difenpiramide Etodolac Felbinac Fenclofenac Fentiazac Glucametacin Indometacin (indomethacin) Indometacin farnesil Ketorolac Lonazolac Mofezolac Nabumetone Oxametacin Oxindanac Proglumetacin Sulindac Sulindac sulfide Tolmetin Zidometacin Zomepirac; Propionic acids: Alminoprofen Benoxaprofen Bucloxic acid (blucloxate) Butibufen Carprofen Dexibuprofen Dexindoprofen Dexketoprofen Fenbufen Fenoprofen Flunoxaprofen Flurbiprofen Ibuprofen Ibuproxam Indoprofen Ketoprofen Loxoprofen Miroprofen Naproxen Naproxcinod Oxaprozin Pirprofen Pranoprofen Suprofen Tarenflurbil Tepoxalin Tiaprofenic acid (tiaprofenate) Vedaprofen; Anthranilic acids (fenamic acids): Etofenamic acid (etofenamate) Floctafenic acid (floctafenate) Flufenamic acid (flufenamate) Meclofenamic acid (meclofenamate) Mefenamic acid (mefenamate) Morniflumic acid (morniflumate) Niflumic acid (niflumate) Talinflumic acid (talinflumate) Tolfenamic acid (tolfenamate); Pyrazolones: Azapropazone Dipyrone Isopyrin Oxyphenbutazone Phenylbutazone; Enolic acids (oxicams): Ampiroxicam Droxicam Enolicam Isoxicam Lornoxicam Meloxicam Piroxicam Tenoxicam; 4-Aminoquinolines: Antrafenine Floctafenine Glafenine; Quinazolines: Fluproquazone Proquazone; Aminonicotinic acids: Clonixeril Clonixin Flunixin; Sulfonanilides: Flosulide Nimesulide; Aminophenols (anilines): Acetanilide AM-404 (N-arachidonoylaminophenol) Bucetin Paracetamol (acetaminophen) Parapropamol Phenacetin Propacetamol; Selective COX-2 inhibitors (coxibs): Apricoxib Celecoxib Cimicoxib Deracoxib Etoricoxib Firocoxib Lumiracoxib Mavacoxib Parecoxib Polmacoxib Robenacoxib Rofecoxib Tilmacoxib Valdecoxib; Others/unsorted: Anitrazafen Clobuzarit Curcumin DuP-697 FK-3311 Flumizole FR-122047 Glimepiride Hyperforin Itazigrel L-655240 L-670596 Licofelone Menatetrenone (vitamin K₂) NCX-466 NCX-4040 NS-398 Pamicogrel Resveratrol Romazarit Rosmarinic acid Rutecarpine Satigrel SC-236 SC-560 SC-58125 Tenidap Tiflamizole Timegadine Trifenagrel Tropesin
PGD₂STooltip Prostaglandin D synthase	Retinoids Selenium (selenium tetrachloride, sodium selenite, selenium disulfide)
PGESTooltip Prostaglandin E synthase	HQL-79
PGFSTooltip Prostaglandin F synthase	Bimatoprost
PGI₂STooltip Prostacyclin synthase	Tranylcypromine
TXASTooltip Thromboxane A synthase	Camonagrel Dazmegrel Dazoxiben Furegrelate Isbogrel Midazogrel Nafagrel Nicogrelate Ozagrel Picotamide Pirmagrel Ridogrel Rolafagrel Samixogrel Terbogrel U63557A

Others

See also: Receptor/signaling modulators; Leukotriene signaling modulators

Leukotriene signaling modulators

Receptor
(ligands)

BLTTooltip Leukotriene B4 receptor

BLT₁Tooltip Leukotriene B4 receptor 1

BLT₂Tooltip Leukotriene B4 receptor 2

Antagonists: CP-195543
LY-255283
ZK-158252

CysLTTooltip Cysteinyl leukotriene receptor

CysLT₁Tooltip Cysteinyl leukotriene receptor 1

CysLT₂Tooltip Cysteinyl leukotriene receptor 2

Antagonists: BAYu9773
BAYu9916

CysLT_ETooltip Cysteinyl leukotriene receptor E

Agonists: Leukotriene E₄

Enzyme
(inhibitors)

5-LOXTooltip Arachidonate 5-lipoxygenase	2-TEDC Baicalein BW-A4C BW-B70C Caffeic acid CDC CJ-13610 Curcumin Fenleuton Hyperforin Hypericum perforatum (St. John's Wort) Meclofenamic acid (meclofenamate) Minocycline N-Stearoyldopamine Timegadine Zileuton FLAPTooltip Arachidonate 5-lipoxygenase-activating protein inhibitors: AM-103 AM-679 BAYx1005 MK-591 MK-886
12-LOXTooltip Arachidonate 12-lipoxygenase	2-TEDC 3-Methoxytropolone Baicalein CDC
15-LOXTooltip Arachidonate 15-lipoxygenase	2-TEDC CDC Luteolin PD-146176
LTA₄HTooltip Leukotriene A4 hydrolase	Acebilustat Captopril DG-051 Fosinoprilat JNJ-26993135 SA-6541 SC-57461A Ubenimex (bestatin)
LTB₄HTooltip Leukotriene B4 ω-hydroxylase	17-Octadecynoic acid
LTC₄STooltip Leukotriene C4 synthase	Azelastine MK-886
LTC₄HTooltip Leukotriene C4 hydrolase	Acivicin Serine-borate complex
LTD₄Tooltip Leukotriene D4 hydrolase	Cilastatin Ubenimex (bestatin)

Others

See also: Receptor/signaling modulators; Prostanoid signaling modulators

Categories:

Latest revision as of 01:53, 19 July 2024

Biological effects

See also

References