OXYPHENBUTAZONE PIPERAZINE

US Previously Marketed

Details

Stereochemistry	RACEMIC
Molecular Formula	C19H20N2O3.C4H10N2
Molecular Weight	410.5093
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C1CNCCN1.CCCCC2C(=O)N(N(C2=O)C3=CC=C(O)C=C3)C4=CC=CC=C4

InChI

InChIKey=FHVBBQCPAGHXED-UHFFFAOYSA-N

InChI=1S/C19H20N2O3.C4H10N2/c1-2-3-9-17-18(23)20(14-7-5-4-6-8-14)21(19(17)24)15-10-12-16(22)13-11-15;1-2-6-4-3-5-1/h4-8,10-13,17,22H,2-3,9H2,1H3;5-6H,1-4H2

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/5033161 | https://www.ncbi.nlm.nih.gov/pubmed/401711

Oxyphenbutazone is a non-steroidal anti-inflammatory drug, cyclooxygenase (prostaglandin synthetase) inhibitors which was marked under brand name tandearil for the treatment rheumatic disorders such as ankylosing spondylitis, osteoarthritis, and rheumatoid arthritis. But this drug was withdrawn from markets due to bone marrow suppression.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Cyclooxygenase 89 Target ID: CHEMBL2094253 Sources: https://www.ncbi.nlm.nih.gov/pubmed/3108222	Inhibitor 8297

Conditions

Condition	Modality	Highest Phase	Product
Rheumatoid arthritis 316 Sources: https://www.ncbi.nlm.nih.gov/pubmed/401711	Palliative	Withdrawn	TANDEARIL Approved Use Unknown Launch Date 1960
Osteoarthritis 157 Sources: https://www.ncbi.nlm.nih.gov/pubmed/5033161	Palliative	Withdrawn	TANDEARIL Approved Use Unknown Launch Date 1960
Ankylosing spondylitis 33 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1100983	Palliative	Withdrawn	Unknown Approved Use Unknown

C_max

Value	Dose	Analyte	Population
21.42 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10518246/	97.49 mg single, oral dose: 97.49 mg route of administration: Oral experiment type: SINGLE co-administered:	OXYPHENBUTAZONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
12 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10518246/	94.99 mg single, oral dose: 94.99 mg route of administration: Oral experiment type: SINGLE co-administered:	OXYPHENBUTAZONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
18.24 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10518246/	95.75 mg single, oral dose: 95.75 mg route of administration: Oral experiment type: SINGLE co-administered:	OXYPHENBUTAZONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
24.05 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10518246/	98.82 mg single, oral dose: 98.82 mg route of administration: Oral experiment type: SINGLE co-administered:	OXYPHENBUTAZONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
24.54 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10518246/	95.38 mg single, oral dose: 95.38 mg route of administration: Oral experiment type: SINGLE co-administered:	OXYPHENBUTAZONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED

AUC

Value	Dose	Analyte	Population
397.401 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10518246/	97.49 mg single, oral dose: 97.49 mg route of administration: Oral experiment type: SINGLE co-administered:	OXYPHENBUTAZONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
285.932 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10518246/	94.99 mg single, oral dose: 94.99 mg route of administration: Oral experiment type: SINGLE co-administered:	OXYPHENBUTAZONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
381.688 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10518246/	95.75 mg single, oral dose: 95.75 mg route of administration: Oral experiment type: SINGLE co-administered:	OXYPHENBUTAZONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
463.858 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10518246/	98.82 mg single, oral dose: 98.82 mg route of administration: Oral experiment type: SINGLE co-administered:	OXYPHENBUTAZONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
482.606 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10518246/	95.38 mg single, oral dose: 95.38 mg route of administration: Oral experiment type: SINGLE co-administered:	OXYPHENBUTAZONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED

Doses

Dose	Population	Adverse events
800 mg 1 times / day multiple, oral Studied dose Dose: 800 mg, 1 times / day Route: oral Route: multiple Dose: 800 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/4184850	unhealthy, 31-72 years n = 66 Health Status: unhealthy Condition: gout Age Group: 31-72 years Sex: M+F Population Size: 66 Sources: https://pubmed.ncbi.nlm.nih.gov/4184850	Sources: https://pubmed.ncbi.nlm.nih.gov/4184850
200 mg 3 times / day multiple, oral Dose: 200 mg, 3 times / day Route: oral Route: multiple Dose: 200 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/7368966	unhealthy, 48 years n = 1 Health Status: unhealthy Condition: progressive shoulder pain Age Group: 48 years Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/7368966	Disc. AE: Bone marrow granuloma... AEs leading to discontinuation/dose reduction: Bone marrow granuloma (1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/7368966
100 mg 2 times / day multiple, oral Dose: 100 mg, 2 times / day Route: oral Route: multiple Dose: 100 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/13684302	unhealthy, 64 years n = 1 Health Status: unhealthy Condition: rheumatoid arthritis Age Group: 64 years Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/13684302	Disc. AE: Thrombocytopenic purpura... AEs leading to discontinuation/dose reduction: Thrombocytopenic purpura (1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/13684302

AEs

AE	Significance	Dose	Population
Bone marrow granuloma	1 patient Disc. AE	200 mg 3 times / day multiple, oral Dose: 200 mg, 3 times / day Route: oral Route: multiple Dose: 200 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/7368966	unhealthy, 48 years n = 1 Health Status: unhealthy Condition: progressive shoulder pain Age Group: 48 years Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/7368966
Thrombocytopenic purpura	1 patient Disc. AE	100 mg 2 times / day multiple, oral Dose: 100 mg, 2 times / day Route: oral Route: multiple Dose: 100 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/13684302	unhealthy, 64 years n = 1 Health Status: unhealthy Condition: rheumatoid arthritis Age Group: 64 years Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/13684302

Sourcing

Vendor/Aggregator	ID	URL
001 Chemical	DY516431	https://www.001chemical.com/chem/129-20-4
3B Scientific (Wuhan) Corp	3B3-044109	http://www.3bsc.com/index/pro_info.php?id=76308
AA Blocks	AA007NNF	https://www.aablocks.com/goods/Goods/detail?id=AA007NNF
Alfa Chemistry	AP129204	https://reagents.alfa-chemistry.com/product/oxyphenbutazone-cas-129-20-4-3574.html
Alfa Chemistry	1189693-23-9	https://www.alfa-chemistry.com/cas_1189693-23-9.htm
Angene	AGN-PC-07Y4TY	http://www.angenechemical.com/productshow/AGN-PC-07Y4TY.html
BioChemPartner	BCP20014	http://www.biochempartner.com/129-20-4-BCP20014
BioSynth	J-005659	https://www.biosynth.com/en/products/all-products/products/J-005659.html
Chem Scene	CS-0013099	http://www.chemscene.com/129-20-4.html
ChemMol	49415819	http://www.chemmol.com/chemmol/49415819.html
Chemspace	CSSB00000079366	https://chem-space.com/CSSB00000079366
DC Chemicals	DC32086	http://www.dcchemicals.com//product_show-G-29701.html
Finetech	FT-0673468	http://www.finetechnology-ind.com/prod/detail/pub/129-20-4.html
Hairui	HR143044	http://www.hairuichem.com/en/product/129-20-4.html
LGC Standards	DRE-C15810000	https://www.lgcstandards.com/US/en/p/DRE-C15810000
MedChem Express	HY-B1355A	https://www.medchemexpress.com/oxyphenbutazone.html
Molcore	MC516431	https://www.molcore.com/product/129-20-4
Smolecule	S538429	http://www.smolecule.com/products/s538429
THE BioTek	bt-278083	https://www.thebiotek.com/product/inhibitors/bt-278083
Vesino Industrial Co Ltd	VZ36732	http://www.vsnchem.com/goto/product/39397/
eNovation Chemicals	D676128	https://www.enovationchem.com/ProductDetails.asp?ProductID=D676128
iChemical	EBD29759	http://www.ichemical.com/chemicals/cas-129-20-4
mcule	MCULE-3785704527	https://mcule.com/MCULE-3785704527/

PubMed

Title	Date	PubMed
[Inhibitory effect of oxyphenbutazone against Mycobacterium tuberculosis in vitro].	1969 Feb	4976649
Oxyphenbutazone and aplastic anemia.	1972 Nov	5079767
Drug-induced blood dyscrasias in Sweden.	1973 Aug 11	4723818
[Acute myelogenous leukemia. Associated with oxyphenbutazone induced aplastic anemia].	1974 Aug 10	4528134
Further studies of the acute effects of phenylbutazone, oxyphenbutazone and indomethacin on the rat kidney.	1976 Apr	972771
Studies on the modification of renal lesions due to aspirin and oxyphenbutazone in the rat and the effects on the kidney of 2:4 dinitrophenol.	1976 Jul	1004943
Study of fatal bone marrow depression with special reference to phenylbutazone and oxyphenbutazone.	1977 Jun 11	871632
Oxyphenbutazone-induced sialadenitis, intrahepatic cholestasis and pancreatitis.	1985 Sep-Oct	3832725
Risks of agranulocytosis and aplastic anemia. A first report of their relation to drug use with special reference to analgesics. The International Agranulocytosis and Aplastic Anemia Study.	1986 Oct 3	3747087
Effects of commonly used non steroidal anti-inflammatory drugs on gastric mucosa. A clinical, endoscopic and histopathological study.	1990 Sep	2266080
Drug-associated acute pancreatitis: twenty-one years of spontaneous reporting in The Netherlands.	1999 Sep	10484002
Nonsteroidal anti-inflammatory drug sensitizes Mycobacterium tuberculosis to endogenous and exogenous antimicrobials.	2012 Oct 2	23012453
FDA-approved drugs and other compounds tested as inhibitors of human glutathione transferase P1-1.	2013 Sep 5	23769903

Patents

Sample Use Guides

In Vivo Use Guide

4 to 9 mg/kg/day

Route of Administration: Oral

In Vitro Use Guide

It was investigated the possibility of oxyphenbutazone (OPh) inhibited the complement system and thus ameliorated the acute pathological changes induced by immune complexes. Treatment of fresh human serum with OPh inhibited both the classical and alternative complement (C) pathway activities in a dose-dependent fashion with a 50% inhibition dose 1.3 mg/ml. OPh was shown to form complexes with C5, thereby inhibiting the interaction between C3b and C5 and the cleavage of the latter into phlogistic fragments.

Name

Type

Language

OXYPHENBUTAZONE PIPERAZINE

Common Name

English

Oxyphenbutazone piperazine [WHO-DD]

Common Name

English

3,5-PYRAZOLIDINEDIONE, 4-BUTYL-1-(4-HYDROXYPHENYL)-2-PHENYL-, COMPD. WITH PIPERAZINE (1:1)

Systematic Name

English

Code System Code Type Description

FDA UNII

86B165MRR5