AMPIROXICAM

Ampiroxicam
Clinical data
AHFS/ Drugs.com	International Drug Names
Routes of; administration	Oral
ATC code	none;
Legal status
Legal status	In general: ℞ (Prescription only);
Identifiers
	IUPAC name (RS)-Ethyl 1-[2-methyl-1,1-dioxo-3-(pyridin-2-ylcarbamoyl)benzo[e]thiazin-4-yl]oxyethyl carbonate;
CAS Number	99464-64-9 ;
PubChem CID	2176;
ChemSpider	2091 ;
UNII	0PV32JZB1J;
KEGG	D01397 ;
ChEBI	CHEBI:31210 ;
ChEMBL	ChEMBL1909052 ;
CompTox Dashboard ( EPA)	DTXSID6046474 ;
ECHA InfoCard	100.235.757
Chemical and physical data
Formula	C20H21N3O7S
Molar mass	447.46 g·mol−1
3D model ( JSmol)	Interactive image;
Chirality	Racemic mixture
	SMILES CCOC(=O)OC(C)OC1=C(N(S(=O)(=O)C2=CC=CC=C21)C)C(=O)NC3=CC=CC=N3;
	InChI InChI=1S/C20H21N3O7S/c1-4-28-20(25)30-13(2)29-18-14-9-5-6-10-15(14)31(26,27)23(3)17(18)19(24)22-16-11-7-8-12-21-16/h5-13H,4H2,1-3H3,(H,21,22,24) ; Key:LSNWBKACGXCGAJ-UHFFFAOYSA-N ;
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Ampiroxicam ( INN) is a non-steroidal anti-inflammatory drug (NSAID). It is a prodrug of piroxicam.^[1] It has been studied for potential anticancer activity, but preliminary results did not show evidence of such activity.^[2]^[3]

References

^ Carty TJ, Marfat A, Moore PF, Falkner FC, Twomey TM, Weissman A (July 1993). "Ampiroxicam, an anti-inflammatory agent which is a prodrug of piroxicam". Agents and Actions. 39 (3–4): 157–165. doi: 10.1007/BF01998969. PMID 8304243. S2CID 24284281.
^ Choi KH, Shim JH, Huong LD, Cho NP, Cho SD (July 2011). "Inhibition of myeloid cell leukemia-1 by tolfenamic acid induces apoptosis in mucoepidermoid carcinoma". Oral Diseases. 17 (5): 469–475. doi: 10.1111/j.1601-0825.2010.01774.x. PMID 21496182.
^ Shim JH, Shin JA, Jung JY, Choi KH, Choi ES, Cho NP, et al. (March 2011). "Chemopreventive effect of tolfenamic acid on KB human cervical cancer cells and tumor xenograft by downregulating specificity protein 1". European Journal of Cancer Prevention. 20 (2): 102–111. doi: 10.1097/CEJ.0b013e328341e38f. PMID 21131823.

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[pmid8304243-1] Carty TJ, Marfat A, Moore PF, Falkner FC, Twomey TM, Weissman A (July 1993). "Ampiroxicam, an anti-inflammatory agent which is a prodrug of piroxicam". Agents and Actions. 39 (3–4): 157–165. doi: 10.1007/BF01998969. PMID 8304243. S2CID 24284281.

[2] Choi KH, Shim JH, Huong LD, Cho NP, Cho SD (July 2011). "Inhibition of myeloid cell leukemia-1 by tolfenamic acid induces apoptosis in mucoepidermoid carcinoma". Oral Diseases. 17 (5): 469–475. doi: 10.1111/j.1601-0825.2010.01774.x. PMID 21496182.

[3] Shim JH, Shin JA, Jung JY, Choi KH, Choi ES, Cho NP, et al. (March 2011). "Chemopreventive effect of tolfenamic acid on KB human cervical cancer cells and tumor xenograft by downregulating specificity protein 1". European Journal of Cancer Prevention. 20 (2): 102–111. doi: 10.1097/CEJ.0b013e328341e38f. PMID 21131823.

[1]

[2]

[3]

v t e Non-steroidal 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 Hyperforin Nabumetone Nimesulide Oxaceprol Proquazone Superoxide dismutase / orgotein Tenidap
NSAID combinations	Ibuprofen/famotidine Ibuprofen/hydrocodone Ibuprofen/oxycodone Ibuprofen/paracetamol Meloxicam/bupivacaine Naproxen/diphenhydramine Naproxen/esomeprazole
Key: underline indicates initially developed first-in-class compound of specific group; ^# WHO-Essential Medicines; ^† withdrawn drugs; ^‡ veterinary use.
category commons portal

v t e Non-steroidal 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 Hyperforin Nabumetone Nimesulide Oxaceprol Proquazone Superoxide dismutase / orgotein Tenidap
NSAID combinations	Ibuprofen/famotidine Ibuprofen/hydrocodone Ibuprofen/oxycodone Ibuprofen/paracetamol Meloxicam/bupivacaine Naproxen/diphenhydramine Naproxen/esomeprazole
Key: underline indicates initially developed first-in-class compound of specific group; ^# WHO-Essential Medicines; ^† withdrawn drugs; ^‡ veterinary use.
category commons portal

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Clinical data

AHFS/ Drugs.com	International Drug Names
Routes of administration	Oral
ATC code	none
Legal status
Legal status	In general: ℞ (Prescription only)
Identifiers
IUPAC name (RS)-Ethyl 1-[2-methyl-1,1-dioxo-3-(pyridin-2-ylcarbamoyl)benzo[e]thiazin-4-yl]oxyethyl carbonate
CAS Number	99464-64-9^Y
PubChem CID	2176
ChemSpider	2091^Y
UNII	0PV32JZB1J
KEGG	D01397^Y
ChEBI	CHEBI:31210^N
ChEMBL	ChEMBL1909052^N
CompTox Dashboard ( EPA)	DTXSID6046474
ECHA InfoCard	100.235.757
Chemical and physical data
Formula	C₂₀H₂₁N₃O₇S
Molar mass	447.46 g·mol⁻¹
3D model ( JSmol)	Interactive image
Chirality	Racemic mixture
SMILES CCOC(=O)OC(C)OC1=C(N(S(=O)(=O)C2=CC=CC=C21)C)C(=O)NC3=CC=CC=N3
InChI InChI=1S/C20H21N3O7S/c1-4-28-20(25)30-13(2)29-18-14-9-5-6-10-15(14)31(26,27)23(3)17(18)19(24)22-16-11-7-8-12-21-16/h5-13H,4H2,1-3H3,(H,21,22,24)^Y Key:LSNWBKACGXCGAJ-UHFFFAOYSA-N^Y
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