Indoprofen

Indoprofen
	File:Indoprofen.svg
Clinical data
Routes of; administration	Oral
ATC code	M01AE10 (WHO) ;
Legal status
Legal status	Withdrawn;
Pharmacokinetic data
Bioavailability	High (rapid and complete absorption)
Metabolism	Glucuronidation
Elimination half-life	2.3 hours
Excretion	Renal
Identifiers
	IUPAC name 2-[4-(1-oxo-1,3-dihydro-2H-isoindol-2-yl); phenyl]propanoic acid;
CAS Number	31842-01-0 check;
PubChem CID	3718;
DrugBank	DB08951 check;
ChemSpider	3587 check;
UNII	CPE46ZU14N;
KEGG	D04530 check;
ChEBI	CHEBI:76162 check;
ChEMBL	ChEMBL15870 check;
E number	{{#property:P628}}
CompTox Dashboard (EPA)	{{#property:P3117}}Lua error in Module:EditAtWikidata at line 29: attempt to index field 'wikibase' (a nil value).;
ECHA InfoCard	{{#property:P2566}}Lua error in Module:EditAtWikidata at line 29: attempt to index field 'wikibase' (a nil value).
Chemical and physical data
Formula	C17H15NO3
Molar mass	281.311 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C(O)C(c1ccc(cc1)N3C(=O)c2ccccc2C3)C;
	InChI InChI=1S/C17H15NO3/c1-11(17(20)21)12-6-8-14(9-7-12)18-10-13-4-2-3-5-15(13)16(18)19/h2-9,11H,10H2,1H3,(H,20,21) check; Key:RJMIEHBSYVWVIN-UHFFFAOYSA-N check;

Indoprofen is a nonsteroidal anti-inflammatory drug (NSAID). It was withdrawn worldwide in the 1980s after postmarketing reports of severe gastrointestinal bleeding.^[1]

A 2004 study using high-throughput screening found indoprofen to increase production of the survival of motor neuron protein, suggesting it may provide insight into treatments for spinal muscular atrophies.^[1]^[2]

Synthesis

The isoindolone ring system forms the nucleus for this profen NSAID.

File:Indoprofen synthesis.svg

The nitro group in 2-(4-nitrophenyl)propionic acid (1) is reduced using iron and hydrochloric acid to give 2-(4-aminophenyl)propionic acid (2). Reaction with phthalic anhydride then gives the phthalimide (4). Treatment with zinc in acetic acid yields indoprofen after reduction of one of the amide groups.^[3]^[4]^[5]

References

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[1]

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[5]

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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Indoprofen

Synthesis

See also

References

Navigation menu

Clinical data
File:Indoprofen.svg
Routes of administration	Oral
ATC code	M01AE10 (WHO)
Legal status
Legal status	Withdrawn
Pharmacokinetic data
Bioavailability	High (rapid and complete absorption)
Metabolism	Glucuronidation
Elimination half-life	2.3 hours
Excretion	Renal
Identifiers
IUPAC name 2-[4-(1-oxo-1,3-dihydro-2H-isoindol-2-yl) phenyl]propanoic acid
CAS Number	31842-01-0^checkY
PubChem CID	3718
DrugBank	DB08951^checkY
ChemSpider	3587^checkY
UNII	CPE46ZU14N
KEGG	D04530^checkY
ChEBI	CHEBI:76162^checkY
ChEMBL	ChEMBL15870^checkY
E number	{{#property:P628}}
CompTox Dashboard (EPA)	{{#property:P3117}}Lua error in Module:EditAtWikidata at line 29: attempt to index field 'wikibase' (a nil value).
ECHA InfoCard	{{#property:P2566}}Lua error in Module:EditAtWikidata at line 29: attempt to index field 'wikibase' (a nil value).
Chemical and physical data
Formula	C₁₇H₁₅NO₃
Molar mass	281.311 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES O=C(O)C(c1ccc(cc1)N3C(=O)c2ccccc2C3)C
InChI InChI=1S/C17H15NO3/c1-11(17(20)21)12-6-8-14(9-7-12)18-10-13-4-2-3-5-15(13)16(18)19/h2-9,11H,10H2,1H3,(H,20,21)^checkY Key:RJMIEHBSYVWVIN-UHFFFAOYSA-N^checkY

Indoprofen

Synthesis

See also

References

Navigation menu

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