Apricoxib

Chemical compound

Investigational

Identifiers

IUPAC name

4-[2-(4-Ethoxyphenyl)-4-methyl-1H-pyrrol-1-yl]benzenesulfonamide

CAS Number

197904-84-0

PubChem CID

9820073

DrugBank

DB12378

ChemSpider

7995822

UNII

5X5HB3VZ3Z

KEGG

D08657

CompTox Dashboard (EPA)

DTXSID60173502

Chemical and physical dataFormulaC₁₉H₂₀N₂O₃SMolar mass356.44 g·mol⁻¹3D model (JSmol)

Interactive image

SMILES

CCOC1=CC=C(C=C1)C2=CC(=CN2C3=CC=C(C=C3)S(=O)(=O)N)C

InChI

InChI=1S/C19H20N2O3S/c1-3-24-17-8-4-15(5-9-17)19-12-14(2)13-21(19)16-6-10-18(11-7-16)25(20,22)23/h4-13H,3H2,1-2H3,(H2,20,22,23)
Key:JTMITOKKUMVWRT-UHFFFAOYSA-N

Apricoxib is an experimental anticancer drug and nonsteroidal anti-inflammatory drug (NSAID).^[1] It is a COX-2 inhibitor which is intended to improve standard therapy response in molecularly-defined models of pancreatic cancer.^[2] It was also studied in clinical trials for non-small-cell lung cancer.^[3] Development was abandoned in 2015 due to poor clinical trial results.^[4]

References

^ "Apricoxib (Code C74021)". NCI Thesaurus. National Cancer Institute.
^ Kirane A, Toombs JE, Ostapoff K, Carbon JG, Zaknoen S, Braunfeld J, et al. (September 2012). "Apricoxib, a novel inhibitor of COX-2, markedly improves standard therapy response in molecularly defined models of pancreatic cancer". Clinical Cancer Research. 18 (18): 5031–42. doi:10.1158/1078-0432.CCR-12-0453. PMC 3777527. PMID 22829202.
^ Edelman MJ, Tan MT, Fidler MJ, Sanborn RE, Otterson G, Sequist LV, et al. (January 2015). "Randomized, double-blind, placebo-controlled, multicenter phase II study of the efficacy and safety of apricoxib in combination with either docetaxel or pemetrexed in patients with biomarker-selected non-small-cell lung cancer". Journal of Clinical Oncology. 33 (2): 189–94. doi:10.1200/JCO.2014.55.5789. PMC 4890680. PMID 25452446.
^ "Apricoxib". Adis Insight. Springer Nature Switzerland AG.

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 F_2α (dinoprost) Simenepag Taprenepag

FP (F_2α)Tooltip Prostaglandin F receptor

Agonists: Alfaprostol
Bimatoprost
Carboprost
Cloprostenol
Enprostil
Fluprostenol
Latanoprost
Prostaglandin D₂
Prostaglandin F_2α (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 (TX_A2)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