Proglumetacin

Proglumetacin
	Structure of proglumetacin
Clinical data
Trade names	Afloxan, Protaxon, Proxil
Other names	3-[4-[2-[2-[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetyl]oxyethyl]piperazin-1-yl]propyl 4-(benzoylamino)-5-(dipropylamino)-5-oxopentanoate
AHFS/Drugs.com	International Drug Names
ATC code	M01AB14 (WHO) ;
Pharmacokinetic data
Metabolism	Hepatic. Undergoes enterohepatic recirculation
Identifiers
	IUPAC name 3-{4-[2-({[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]acetyl}oxy)ethyl]piperazin-1-yl}propyl N2-benzoyl-N,N-dipropyl-α-glutaminate;
CAS Number	57132-53-3 59209-40-4;
PubChem CID	4921;
ChemSpider	4752 ;
UNII	FV919079LU;
ChEBI	CHEBI:76263;
CompTox Dashboard (EPA)	DTXSID0048842 ;
Chemical and physical data
Formula	C46H58ClN5O8
Molar mass	844.45 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCCN(CCC)C(=O)C(CCC(=O)OCCCN1CCN(CCOC(=O)Cc2c(C)n(C(=O)c3ccc(Cl)cc3)c3ccc(OC)cc23)CC1)NC(=O)c1ccccc1;
	InChI InChI=1S/C46H58ClN5O8/c1-5-21-51(22-6-2)46(57)40(48-44(55)34-11-8-7-9-12-34)18-20-42(53)59-29-10-23-49-24-26-50(27-25-49)28-30-60-43(54)32-38-33(3)52(41-19-17-37(58-4)31-39(38)41)45(56)35-13-15-36(47)16-14-35/h7-9,11-17,19,31,40H,5-6,10,18,20-30,32H2,1-4H3,(H,48,55) ; Key:PTXGHCGBYMQQIG-UHFFFAOYSA-N ;
	(verify)

Proglumetacin (usually supplied as the maleate salt) is a nonsteroidal anti-inflammatory drug (NSAID). It is a codrug (that is, a mutual prodrug) of indometacin and proglumide.^[1] After oral intake, it is absorbed and metabolized to indometacin and proglumide. These two substances are then released into the system in a 1:1 molar ratio.

Indometacin contributes to the anti-inflammatory effect, while proglumide has antisecretory effects that helps prevent injury to the stomach lining.

References

↑ Setnikar I, Arigoni R, Chisté R, Makovec F, Revel L (1987). "Plasma levels of proglumetacin and its metabolites after intravenous or oral administration in the dog". Arzneimittel-Forschung. 37 (6): 698–702. PMID 3663267.

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[1] Setnikar I, Arigoni R, Chisté R, Makovec F, Revel L (1987). "Plasma levels of proglumetacin and its metabolites after intravenous or oral administration in the dog". Arzneimittel-Forschung. 37 (6): 698–702. PMID 3663267.

[1]

v t e Nonsteroidal anti-inflammatory drugs (NSAIDs) (primarily M01A and M02A, also N02BA)
pyrazolones / pyrazolidines	Aminophenazone Ampyrone Azapropazone Clofezone Difenamizole Famprofazone Feprazone Kebuzone Metamizole Mofebutazone Morazone Nifenazone Oxyphenbutazone Phenazone Phenylbutazone Propyphenazone Sulfinpyrazone Suxibuzone^‡
salicylates	Aspirin (acetylsalicylic acid)^# Aloxiprin Benorylate Carbasalate calcium Diflunisal Dipyrocetyl Ethenzamide Guacetisal Magnesium salicylate Methyl salicylate Salsalate Salicin Salicylamide Salicylic acid (salicylate) Sodium salicylate
acetic acid derivatives and related substances	Aceclofenac Acemetacin Alclofenac Amfenac Bendazac Bromfenac Bufexamac Bumadizone Diclofenac Difenpiramide Etodolac Felbinac Fenclozic acid Fentiazac Indometacin Indometacin farnesil Isoxepac Ketorolac Lonazolac Mofezolac Oxametacin Prodolic acid Proglumetacin Sulindac Tiopinac Tolmetin Zomepirac^†
oxicams	Ampiroxicam Droxicam Isoxicam Lornoxicam Meloxicam Piroxicam Pivoxicam Tenoxicam
propionic acid derivatives (profens)	Alminoprofen Benoxaprofen^† Carprofen^‡ Dexibuprofen Dexketoprofen Fenbufen Fenoprofen Flunoxaprofen Flurbiprofen Ibuprofen^# Ibuproxam Indoprofen^† Ketoprofen Loxoprofen Miroprofen Naproxen Oxaprozin Pelubiprofen Piketoprofen Pirprofen Suprofen Tarenflurbil Tepoxalin^‡ Tiaprofenic acid Vedaprofen^‡ Zaltoprofen COX-inhibiting nitric oxide donator: Naproxcinod
n-arylanthranilic acids (fenamates)	Azapropazone Clonixin Etofenamate Floctafenine Flufenamic acid Flunixin Flutiazin Glafenine^† Meclofenamic acid Mefenamic acid Morniflumate Niflumic acid Tolfenamic acid
COX-2 inhibitors (coxibs)	Apricoxib Celecoxib (+tramadol) Cimicoxib^‡ Deracoxib^‡ Etoricoxib Firocoxib^‡ Lumiracoxib^† Mavacoxib^‡ Parecoxib Robenacoxib^‡ Rofecoxib^† Valdecoxib^†
other	Aminopropionitrile Benzydamine Chondroitin sulfate Diacerein Fluproquazone Glucosamine Glycosaminoglycan Grapiprant^‡ Hyperforin Nabumetone Nimesulide Oxaceprol Proquazone Superoxide dismutase / orgotein Tenidap
NSAID combinations	Ibuprofen/famotidine Ibuprofen/hydrocodone Ibuprofen/oxycodone Ibuprofen/paracetamol Meloxicam/bupivacaine Meloxicam/rizatriptan Naproxen/diphenhydramine Naproxen/esomeprazole
Key: underline indicates initially developed first-in-class compound of specific group; ^#WHO-Essential Medicines; ^†withdrawn drugs; ^‡veterinary use.
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