Ifetroban

Ifetroban
Systematic (IUPAC) name

3-[2-({(1S,2R,3S)-3-[4-(pentylcarbamoyl)-1,3-oxazol-2-yl]-7-oxabicyclo[2.2.1]hept-2-yl}methyl)phenyl]propanoic acid
Identifiers
CAS Number	143443-90-7
PubChem	CID 23724921
ChemSpider	58452
UNII	E833KT807K^Y
KEGG	D04500
ChEMBL	CHEMBL2146062
Chemical data
Formula	C₂₅H₃₂N₂O₅
Molar mass	440.53 g/mol
SMILES O=C(NCCCCC)c1nc(oc1)[C@@H]4C2O[C@@H](CC2)[C@@H]4Cc3ccccc3CCC(=O)O

Ifetroban is a potent and selective thromboxane receptor antagonist.^[1]

Synthesis

Ifetroban synthesis: Drugs Future (c.f. Lednicer book 6).

References

↑ Dockens, R.; Santone, K.; Mitroka, J.; Morrison, R.; Jemal, M.; Greene, D.; Barbhaiya, R. (2000). "Disposition of radiolabeled ifetroban in rats, dogs, monkeys, and humans". Drug metabolism and disposition: the biological fate of chemicals 28 (8): 973–980. PMID 10901709.

Prostanoid signaling

Receptor
(ligands)

DP (D₂)

DP₁	Agonists: Prostaglandin D₂ Treprostinil Antagonists: Asapiprant Laropiprant Vidupiprant

DP₂	Agonists: Indometacin Prostaglandin D₂ Antagonists: ADC-3680 AZD-1981 Bay U3405 Fevipiprant MK-1029 MK-7246 OC-459 OC000459 QAV-680 Ramatroban Setipiprant TM30089 Vidupiprant

EP (E₂)

EP₁	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

EP₂	Agonists: Butaprost Misoprostol Prostaglandin E₁ (alprostadil) Prostaglandin E₂ (dinoprostone) Treprostinil Antagonists: AH-6809 PF-04418948 TG 4-155

EP₃	Agonists: Beraprost Carbacyclin Cicaprost Enprostil Iloprost (ciloprost) Isocarbacyclin Latanoprost Misoprostol Prostaglandin D₂ Prostaglandin E₁ (alprostadil) Prostaglandin E₂ (dinoprostone) Remiprostol Sulprostone Antagonists: L-798106

EP₄	Agonists: Lubiprostone Misoprostol Prostaglandin E₁ (alprostadil) Prostaglandin E₂ (dinoprostone) TCS-2510 Antagonists: GW-627368 L-161982 ONO-AE3-208

Unsorted	Agonists: 16,16-Dimethyl Prostaglandin E₂ Aganepag Carboprost Evatanepag Gemeprost Nocloprost Prostaglandin F_2α (dinoprost) Simenepag Taprenepag

FP (F_2α)

IP (I₂)

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)

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)	Aceclofenac Acemetacin Acetanilide Alclofenac Alminoprofen Aloxiprin AM404 Amfenac Ampiroxicam Anitrazafen Antrafenine Apricoxib Aspirin (acetylsalicylic acid) Azapropazone Bendazac Benorilate (benorylate) Benoxaprofen Bromfenac Bucetin Bucloxic acid (blucloxate) Bufexamac Bumadizone Butibufen Carbasalate calcium Carprofen Celecoxib Cimicoxib Cinmetacin Clobuzarit Clometacin Clonixeril Clonixin Curcumin Deracoxib Dexibuprofen Dexindoprofen Dexketoprofen Diclofenac Difenpiramide Diflunisal Dipyrocetyl Droxicam DuP-697 Enolicam Ethenzamide Etodolac Etofenamate Etoricoxib Felbinac Fenbufen Fenclofenac Fenoprofen Fentiazac Firocoxib FK-3311 Floctafenic acid (floctafenate) Floctafenine Flosulide Flufenamic acid (flufenamate) Flumizole Flunixin Flunoxaprofen Fluproquazone Flurbiprofen FR-122047 Glafenine Glimepiride Glucametacin Guacetisal Hyperforin Ibuprofen Ibuproxam Indometacin farnesil Indometacin (indomethacin) Indoprofen Isoxicam Itazigrel Ketoprofen Ketorolac L-655240 L-670596 Licofelone Lonazolac Lornoxicam Loxoprofen Lumiracoxib Magnesium salicylate Mavacoxib Meclofenamic acid (meclofenamate) Mefenamic acid (mefenamate) Meloxicam Menatetrenone (vitamin K₂) Mesalazine (5-aminosalicylic acid) Methyl salicylate Miroprofen Mofezolac Morniflumate Nabumetone Naproxcinod Naproxen NCX-466 NCX-4040 Niflumic acid (niflumate) Nimesulide NS-398 Oxametacin Oxaprozin Oxindanac Pamicogrel Paracetamol (acetaminophen) Parapropamol Parecoxib Phenacetin Piroxicam Pirprofen Polmacoxib Pranoprofen Proglumetacin Propacetamol Resveratrol Robenacoxib Rofecoxib Romazarit Rutecarpine Salacetamide Salicin Salicylamide Salicylic acid (salicylate) Salsalate Satigrel SC-236 SC-560 SC-58125 Sodium salicylate Sulindac Sulindac sulfide Suprofen Talinflumic acid (talinflumate) Tarenflurbil Tenidap Tenoxicam Tepoxalin Tiaprofenic acid (tiaprofenate) Tiflamizole Tilmacoxib Timegadine Tolfenamic acid (tolfenamate) Tolmetin Trifenagrel Triflusal Tropesin Valdecoxib Vedaprofen Zidometacin Zomepirac

PGD₂ synthase	Retinoids Selenium (selenium tetrachloride, sodium selenite, selenium disulfide)

PGE synthase	HQL-79

PGF synthase	Bimatoprost

PGI₂ synthase	Tranylcypromine

TXA synthase	Camonagrel Dazmegrel Dazoxiben Furegrelate Isbogrel Midazogrel Nafagrel Nicogrelate Ozagrel Picotamide Pirmagrel Ridogrel Rolafagrel Samixogrel Terbogrel U63557A

Others

See also: Leukotrienergics

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