Glafenine

Glafenine
Clinical data

ATC code	N02BG03 (WHO)
Identifiers
IUPAC name 2,3-Dihydroxypropyl 2-[(7-chloro-4-quinolinyl)amino]benzoate
CAS Number	3820-67-5
PubChem (CID)	3474
ChemSpider	3355
ChEBI	CHEBI:31653^Y
ChEMBL	CHEMBL146095
ECHA InfoCard	100.021.197
Chemical and physical data
Formula	C₁₉H₁₇ClN₂O₄
Molar mass	372.802 g/mol
3D model (Jmol)	Interactive image
Melting point	169 to 170 °C (336 to 338 °F)
SMILES O=C(OCC(O)CO)c1ccccc1Nc2c3ccc(Cl)cc3ncc2
InChI InChI=1S/C19H17ClN2O4/c20-12-5-6-14-17(7-8-21-18(14)9-12)22-16-4-2-1-3-15(16)19(25)26-11-13(24)10-23/h1-9,13,23-24H,10-11H2,(H,21,22) Key:GWOFUCIGLDBNKM-UHFFFAOYSA-N

Glafenine is a non-steroidal anti-inflammatory drug (NSAID). Use of glafenine is limited due to the risk of anaphylaxis and acute kidney failure.^[1]^[2]

References

↑ "Withdrawal of glafenine". The Lancet. 339 (8789): 357. 1992. doi:10.1016/0140-6736(92)91670-4.
↑ Kleinknecht, D; Landais, P; Goldfarb, B (1986). "Analgesic and non-steroidal anti-inflammatory drug-associated acute renal failure: A prospective collaborative study". Clinical nephrology. 25 (6): 275–81. PMID 2873910.

Analgesics (N02A, N02B)

Opioids

Opiates/opium	Codeine^# (+paracetamol, +aspirin) Morphine^# (+naltrexone) Opium Laudanum Paregoric

Semisynthetic	Acetyldihydrocodeine Benzylmorphine Buprenorphine (+naloxone) Desomorphine Diamorphine (heroin) Dihydrocodeine (+paracetamol) Dihydromorphine Ethylmorphine Hydrocodone (+paracetamol, +ibuprofen, +aspirin) Hydromorphinol Hydromorphone Nicocodeine Nicodicodeine Nicomorphine Oxycodone (+paracetamol, +aspirin, +ibuprofen, +naloxone, +naltrexone) Oxymorphone Thebacon

Synthetic	Alphaprodine Anileridine Butorphanol Dextromoramide Dextropropoxyphene Dezocine Fentanyl (+fluanisone) Ketobemidone Levorphanol Meptazinol Methadone Nalbuphine Pentazocine Pethidine Phenadoxone Phenazocine Piminodine Piritramide Propiram Tapentadol Tilidine Tramadol

Paracetamol-type

Acetanilide^‡
Bucetin^‡
Butacetin^‡
Paracetamol (acetaminophen)^#
Parapropamol^‡
Phenacetin^‡
Propacetamol^‡

NSAIDs

Propionates	Fenoprofen Flurbiprofen Ibuprofen^# Ketoprofen Naproxen Oxaprozin

Oxicams	Meloxicam Piroxicam

Acetates	Diclofenac Indometacin Ketorolac Nabumetone Sulindac Tolmetin

COX-2 inhibitors	Celecoxib Etoricoxib Lumiracoxib Parecoxib Rofecoxib ^‡ Valdecoxib ^‡

Fenamates	Meclofenamic acid Mefenamic acid

Salicylates	Aspirin (acetylsalicylic acid)^# (+paracetamol/caffeine) Benorylate Diflunisal Ethenzamide Magnesium salicylate Salicin Salicylamide Salsalate Wintergreen (methyl salicylate)

Pyrazolones	Aminophenazone^‡ Ampyrone Metamizole (dipyrone) Nifenazone Phenazone Propyphenazone

Others	Glafenine

Cannabinoids

Ion channel
modulators

Calcium blockers	Gabapentin Gabapentin enacarbil Pregabalin Ziconotide

Sodium blockers	Carbamazepine Lacosamide Local anesthetics (e.g., cocaine, lidocaine) Mexiletine Nefopam Tricyclic antidepressants (e.g., amitriptyline^#) Na_v1.7/1.8-selective: DSP-2230^§ Funapide^§ PF-05089771^§ Raxatrigine^§

Potassium openers	Flupirtine

Myorelaxants

Others

Camphor
Capsaicin
Clonidine
Ketamine
Menthol
Methoxyflurane
Nefopam
Proglumide
Tricyclic antidepressants (e.g., amitriptyline^#)

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

Prostanoid signaling modulators

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 Omidenepag 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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