Bucetin

Chemical compound

Bucetin

Clinical data
ATC code|

* N02BE04 (WHO)

Identifiers

IUPAC name

* N-(4-Ethoxyphenyl)-3-hydroxybutanamide

CAS Number|

* 1083-57-4 Y

PubChem CID|

* 14130

ChemSpider|

* 13507

UNII|

* 6M7CVQ8PF8

ChEMBL|

* ChEMBL1697856

CompTox Dashboard (EPA)|

* DTXSID6020721

ECHA InfoCard| 100.012.827
Chemical and physical data
Formula| C12H17NO3
Molar mass| 223.272 g·mol−1
3D model (JSmol)|

* Interactive image

SMILES

* O=C(Nc1ccc(OCC)cc1)CC(O)C

InChI

* InChI=1S/C12H17NO3/c1-3-16-11-6-4-10(5-7-11)13-12(15)8-9(2)14/h4-7,9,14H,3,8H2,1-2H3,(H,13,15)

* Key:LIAWQASKBFCRNR-UHFFFAOYSA-N

Bucetin (INN, BAN) is an analgesic and antipyretic that is no longer marketed.[1][2] Chemically, it is similar to phenacetin with which it shares the risk of carcinogenesis.[3] Bucetin was withdrawn from use in 1986 due to renal toxicity.[4]

## See also

[edit]

* Analgesic nephropathy
* List of withdrawn drugs

## References

[edit]

1. ^ J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 184–. ISBN 978-1-4757-2085-3.
2. ^ "WHOCC - ATC/DDD Index". WHO Collaborating Centre for Drug Statistics Methodology. December 19, 2013.
3. ^ Togei K, Sano N, Maeda T, Shibata M, Otsuka H (November 1987). "Carcinogenicity of bucetin in (C57BL/6 X C3H)F1 mice". Journal of the National Cancer Institute. 79 (5): 1151–8. doi:10.1093/jnci/79.5.1151. PMID 3479641.
4. ^ Fung M, Thornton A, Mybeck K, Wu JH, Hornbuckle K, Muniz E (2001). "Evaluation of the Characteristics of Safety Withdrawal of Prescription Drugs from Worldwide Pharmaceutical Markets-1960 to 1999". Drug Information Journal. 35: 293–317. doi:10.1177/009286150103500134. S2CID 73036562.

* 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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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 F2α (dinoprost)
* Simenepag
* Taprenepag

FP (F2α)Tooltip Prostaglandin F receptor|

* Agonists: Alfaprostol
* Bimatoprost
* Carboprost
* Cloprostenol
* Enprostil
* Fluprostenol
* Latanoprost
* Prostaglandin D2
* Prostaglandin F2α (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 (TXA2)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

Others|

* Precursors: Linoleic acid
* γ-Linolenic acid (gamolenic acid)
* Dihomo-γ-linolenic acid
* Diacylglycerol
* Arachidonic acid
* Prostaglandin G2
* Prostaglandin H2

See also
Receptor/signaling modulators
Leukotriene signaling modulators

Look up bucetin in Wiktionary, the free dictionary.

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|

* v
* t
* e

*[CID]: Compound ID
*[EPA]: U.S. Environmental Protection Agency
*[v]: View this template
*[t]: Discuss this template
*[e]: Edit this template
*[DP (D2)]: Prostaglandin D2 receptor
*[DP1]: Prostaglandin D2 receptor 1
*[DP2]: Prostaglandin D2 receptor 2
*[EP (E2)]: Prostaglandin E2 receptor
*[EP1]: Prostaglandin EP1 receptor
*[EP2]: Prostaglandin EP2 receptor
*[EP3]: Prostaglandin EP3 receptor
*[EP4]: Prostaglandin EP4 receptor
*[FP (F2α)]: Prostaglandin F receptor
*[IP (I2)]: Prostacyclin receptor
*[TP (TXA2)]: Thromboxane receptor
*[COX]: Cyclooxygenase
*[PTGS]: prostaglandin G/H synthase
*[PGD2S]: Prostaglandin D synthase
*[PGES]: Prostaglandin E synthase
*[PGFS]: Prostaglandin F synthase
*[PGI2S]: Prostacyclin synthase
*[TXAS]: Thromboxane A synthase