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  1. World Encyclopedia
  2. Prostanoid - Wikipedia
Prostanoid - Wikipedia
From Wikipedia, the free encyclopedia
Class of biomolecules regulating inflammatory response
Main articles: Prostaglandin, Prostacyclin, and Thromboxane

In molecular biology, prostanoids are active lipid mediators that regulate inflammatory response. Prostanoids are a subclass of eicosanoids consisting of the prostaglandins (mediators of inflammatory and anaphylactic reactions), the thromboxanes (mediators of vasoconstriction), and the prostacyclins (active in the resolution phase of inflammation).[citation needed] Prostanoids are seen to target NSAIDS which allow for therapeutic potential. Prostanoids are present within areas of the body such as the gastrointestinal tract, urinary tract, respiratory and cardiovascular systems, reproductive tract and vascular system. Prostanoids can even be seen with aid to the water and ion transportation within cells.

History

[edit]

Prostanoids were discovered through biological research studies conducted in the 1930s.[1][2] The first discovery was seen through semen by a Swedish Physiologist Ulf von Euler, who assumed they originated from the prostate. After intensive study throughout the 1960-1970s Sune K. Bergström and Bengt Ingemar Samuelsson and British biochemist Sir John Robert Vane were able to understand the function and chemical formation of Prostanoids: receiving a Nobel Prize for their analysis of prostanoids.

Biosynthesis of prostaglandins

[edit]
Prostaglandin H2
PGD synthase
PGD2
PGJ2
PGE
synthase
PGE2
PGA2
PGB2
Prostacyclin synthase
PGI2
6-keto-PGFα
PGE 9-
ketoreductase
PGF2
Thromboxane-A
synthase
TXA2

Cyclooxygenase (COX) catalyzes the conversion of the free essential fatty acids to prostanoids by a two-step process. In the first step, two molecules of O2 are added as two peroxide linkages and a 5-member carbon ring is forged near the middle of the fatty acid chain. This forms the short-lived, unstable intermediate Prostaglandin G (PGG). One of the peroxide linkages sheds a single oxygen, forming PGH. (See diagrams and more detail at Cyclooxygenase). All other prostanoids originate from PGH (as PGH1, PGH2, or PGH3).

The image at right shows how PGH2 (derived from Arachidonic acid) is converted:

  • By PGE synthetase into PGE2 (which in turn is converted into PGF2)
  • By PGD synthetase into PGD2
  • By Prostacyclin synthase into prostacyclin (PGI2)
  • By Thromboxane synthase into thromboxanes TXA

Arachidonic acid is made up of a 20-Carbon unnatural poly unsaturated Omega-fatty acid.[citation needed] Arachidonic acid presents within the phospholipid bi-layer as well as in the plasma membrane of a cell. With Arachidonic acid prostaglandins are formed through synthesis and oxygenation of enzymes. Active lipids in the oxylipin family derive from the synthesis of Cyclooxygenase or Prostaglandins.

The three classes of prostanoids have distinctive rings in the center of the molecule. They differ in their structures and do not share common structure as Thromboxane. The PGH compounds (parents to all the rest) have a 5-carbon ring, bridged by two oxygens (a peroxide.) The derived prostaglandins contain a single, unsaturated 5-carbon ring. In prostacyclins, this ring is conjoined to another oxygen-containing ring. In thromboxanes the ring becomes a 6-member ring with one oxygen.

Production of PGE2 in bacterial and viral infections appear to be stimulated by certain cytokines, e.g., interleukin-1.[3]

See also

[edit]
  • Prostaglandin
  • Prostaglandin receptors
  • Prostanoid receptors
  • Essential fatty acid
  • Isoprostane
  • Prostacyclin

References

[edit]
  1. ^ Christie, William (Bill) W. "Prostanoids: Prostaglandins, Prostacyclins and Thromboxanes". www.lipidmaps.org. Retrieved 2022-05-12.
  2. ^ "prostaglandin | Definition, Function, Synthesis, & Facts | Britannica". www.britannica.com. Retrieved 2022-05-12.
  3. ^ University of Kansas Medical Center (2004). "Eicosanoids and Inflammation" (PDF). Archived from the original (PDF) on 2005-05-16. Retrieved 2007-01-05.


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Eicosanoids
Precursor
  • Arachidonic acid
Prostanoids
Prostaglandins (PG)
Precursor
  • H2
Active
D/J
  • D2
E/F
  • E2 (Dinoprostone)
  • E1 (Alprostadil)
  • F2α (Dinoprost):
I
  • I2 (Prostacyclin/Epoprostenol):
Thromboxanes (TX)
  • A2
  • B2
Leukotrienes (LT)
Precursor
  • Arachidonic acid 5-hydroperoxide
Initial
  • A4
  • B4
SRS-A
  • C4
  • D4
  • E4
Eoxins (EX)
Precursor
  • Arachidonic acid 15-hydroperoxide
Eoxins
  • A4
  • C4
  • D4
  • E4
Nonclassic
  • Lipoxins (LX) (A4, B4)
  • Virodhamine
By function
  • bronchoconstriction
    • PGD2
    • TXA2
    • LTC4
    • LTD4
    • LTE4
  • vasoconstriction
    • PGF2α
    • TXA2
    • TXB2
  • vasodilation
    • PGE2
    • PGI2
    • LTC4
    • LTD4
    • LTE4
  • platelets: induce
    • TXA2
  • inhibit
    • PGD2
    • PGI2
  • leukocytes: induce
    • TXA2
    • LTB4
  • inhibit
    • PGD2
    • PGE2
  • fever stimulation:
    • PGE2
  • labor stimulation:
    • PGE2 (Dinoprostone)
    • PGF2α (Dinoprost)
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Prostanoid signaling modulators
Receptor
(ligands)
DP (D2)Tooltip Prostaglandin D2 receptor
DP1Tooltip Prostaglandin D2 receptor 1
  • Agonists: Prostaglandin D2
  • Treprostinil
  • Antagonists: Asapiprant
  • Laropiprant
  • Vidupiprant
DP2Tooltip Prostaglandin D2 receptor 2
  • Agonists: Indometacin
  • Prostaglandin D2
  • Antagonists: ADC-3680
  • AZD-1981
  • Bay U3405
  • Fevipiprant
  • MK-1029
  • MK-7246
  • QAV-680
  • Ramatroban
  • Setipiprant
  • Timapiprant
  • TM30089
  • Vidupiprant
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 F2α (dinoprost)
  • Simenepag
  • Taprenepag
FP (F2α)Tooltip Prostaglandin F receptor
  • Agonists: Alfaprostol
  • Bimatoprost
  • Carboprost
  • Cloprostenol
  • Enprostil
  • Fluprostenol
  • Latanoprost
  • Prostaglandin D2
  • Prostaglandin F2α (dinoprost)
  • Sulotroban
  • Tafluprost
  • Travoprost
  • Unoprostone
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 (TXA2)Tooltip Thromboxane receptor
  • Agonists: Carbocyclic thromboxane A2
  • I-BOP
  • Thromboxane A2
  • U-46619
  • Vapiprost
  • Antagonists: 12-HETE
  • 13-APA
  • AA-2414
  • Argatroban
  • Bay U3405
  • BMS-180,291
  • Daltroban
  • Domitroban
  • EP-045
  • GR-32191
  • ICI-185282
  • ICI-192605
  • Ifetroban
  • Imitrodast
  • L-655240
  • L-670596
  • Linotroban
  • Mipitroban
  • ONO-3708
  • ONO-11120
  • Picotamide
  • Pinane thromboxane A2
  • Ramatroban
  • Ridogrel
  • S-145
  • Samixogrel
  • Seratrodast
  • SQ-28,668
  • SQ-29,548
  • Sulotroban
  • Terbogrel
  • Terutroban
  • TRA-418
Unsorted
  • Arbaprostil
  • Ataprost
  • Ciprostene
  • Clinprost
  • Cobiprostone
  • Delprostenate
  • Deprostil
  • Dimoxaprost
  • Doxaprost
  • Ecraprost
  • Eganoprost
  • Enisoprost
  • Eptaloprost
  • Esuberaprost
  • Etiproston
  • Fenprostalene
  • Flunoprost
  • Froxiprost
  • Lanproston
  • Limaprost
  • Luprostiol
  • Meteneprost
  • Mexiprostil
  • Naxaprostene
  • Nileprost
  • Nocloprost
  • Ornoprostil
  • Oxoprostol
  • Penprostene
  • Pimilprost
  • Piriprost
  • Posaraprost
  • Prostalene
  • Rioprostil
  • Rivenprost
  • Rosaprostol
  • Spiriprostil
  • Tiaprost
  • Tilsuprost
  • Tiprostanide
  • Trimoprostil
  • Viprostol
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
  • Precursors: Linoleic acid
  • γ-Linolenic acid (gamolenic acid)
  • Dihomo-γ-linolenic acid
  • Diacylglycerol
  • Arachidonic acid
  • Prostaglandin G2
  • Prostaglandin H2
See also
Receptor/signaling modulators
Leukotriene signaling modulators
Stub icon

This biochemistry article is a stub. You can help Wikipedia by adding missing information.

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Retrieved from "https://teknopedia.ac.id/w/index.php?title=Prostanoid&oldid=1329980186"
Categories:
  • Prostaglandins
  • Eicosanoids
  • Biochemistry stubs
Hidden categories:
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  • Short description is different from Wikidata
  • All articles with unsourced statements
  • Articles with unsourced statements from December 2025
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