OXYPHENBUTAZONE

Details

Stereochemistry	RACEMIC
Molecular Formula	C19H20N2O3.H2O
Molecular Weight	342.389
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

O.CCCCC1C(=O)N(N(C1=O)C2=CC=C(O)C=C2)C3=CC=CC=C3

InChI

InChIKey=CNDQSXOVEQXJOE-UHFFFAOYSA-N

InChI=1S/C19H20N2O3.H2O/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;/h4-8,10-13,17,22H,2-3,9H2,1H3;1H2

HIDE SMILES / InChI

Molecular Formula	H2O
Molecular Weight	18.0153
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	C19H20N2O3
Molecular Weight	324.3737
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

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 But this drug was withdrawn from markets due to bone marrow suppression.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 8504

Conditions

Condition	Modality	Highest Phase	Product
Rheumatoid arthritis 320 Sources: https://www.ncbi.nlm.nih.gov/pubmed/401711	Palliative	Withdrawn	TANDEARIL Approved Use Unknown Launch Date 1960
Osteoarthritis 157 Sources: https://www.ncbi.nlm.nih.gov/pubmed/5033161	Palliative	Withdrawn	TANDEARIL Approved Use Unknown Launch Date 1960
Ankylosing spondylitis 33 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1100983	Palliative	Withdrawn	Unknown Approved Use Unknown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
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
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
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

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
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
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
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

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 Health Status: unhealthy Age Group: 31-72 years Sex: M+F 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 Health Status: unhealthy Age Group: 48 years Sex: F 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 Health Status: unhealthy Age Group: 64 years Sex: F 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 Health Status: unhealthy Age Group: 48 years Sex: F 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 Health Status: unhealthy Age Group: 64 years Sex: F 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	1189693-23-9	https://www.alfa-chemistry.com/cas_1189693-23-9.htm
Alfa Chemistry	AP129204	https://reagents.alfa-chemistry.com/product/oxyphenbutazone-cas-129-20-4-3574.html
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
eNovation Chemicals	D676128	https://www.enovationchem.com/ProductDetails.asp?ProductID=D676128
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
iChemical	EBD29759	http://www.ichemical.com/chemicals/cas-129-20-4
LGC Standards	DRE-C15810000	https://www.lgcstandards.com/US/en/p/DRE-C15810000
mcule	MCULE-3785704527	https://mcule.com/MCULE-3785704527/
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/

PubMed

Title	Date	PubMed
FDA-approved drugs and other compounds tested as inhibitors of human glutathione transferase P1-1.	2013-09-05	23769903
Nonsteroidal anti-inflammatory drug sensitizes Mycobacterium tuberculosis to endogenous and exogenous antimicrobials.	2012-10-02	23012453
Drug-associated acute pancreatitis: twenty-one years of spontaneous reporting in The Netherlands.	1999-09	10484002
Effects of commonly used non steroidal anti-inflammatory drugs on gastric mucosa. A clinical, endoscopic and histopathological study.	1990-09	2266080
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.	1986-10-03	3747087
Oxyphenbutazone-induced sialadenitis, intrahepatic cholestasis and pancreatitis.	1985-09-01	3832725
Study of fatal bone marrow depression with special reference to phenylbutazone and oxyphenbutazone.	1977-06-11	871632
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.	1976-07	1004943
Further studies of the acute effects of phenylbutazone, oxyphenbutazone and indomethacin on the rat kidney.	1976-04	972771
[Acute myelogenous leukemia. Associated with oxyphenbutazone induced aplastic anemia].	1974-08-10	4528134
Drug-induced blood dyscrasias in Sweden.	1973-08-11	4723818
Oxyphenbutazone and aplastic anemia.	1972-11	5079767
[Inhibitory effect of oxyphenbutazone against Mycobacterium tuberculosis in vitro].	1969-02	4976649

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.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:30:51 GMT 2025` Edited by `admin` on `Mon Mar 31 18:30:51 GMT 2025`
Record UNII	H806S4B3NS
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

OXYPHENBUTAZONE

Official Name

English

OXYPHENBUTAZONE MONOHYDRATE

Preferred Name

English

(±)-OXYPHENBUTAZONE MONOHYDRATE

Common Name

English

OXYPHENBUTAZONE [VANDF]

Common Name

English

PHLOGONT

Brand Name

English

PHLOGISTOL

Brand Name

English

OXYPHENBUTAZONE MONOHYDRATE, (±)-

Common Name

English

OXYPHENBUTAZONE [IARC]

Common Name

English

OXYPHENBUTAZONE MONOHYDRATE [MI]

Common Name

English

OXYPHENBUTAZONE HYDRATE

Common Name

English

NSC-757261

Code

English

3,5-PYRAZOLIDINEDIONE, 4-BUTYL-1-(4-HYDROXYPHENYL)-2-PHENYL-, HYDRATE (1:1)

Systematic Name

English

OXIPHENBUTAZONE

Common Name

English

4-BUTYL-1-(P-HYDROXYPHENYL)-2-PHENYL-3,5-PYRAZOLIDINEDIONE MONOHYDRATE

Common Name

English

OXYPHENBUTAZONE [ORANGE BOOK]

Common Name

English

PHLOGASE

Brand Name

English

3,5-PYRAZOLIDINEDIONE, 4-BUTYL-1-(4-HYDROXYPHENYL)-2-PHENYL-, MONOHYDRATE

Systematic Name

English

Classification Tree Code System Code

WHO-VATC

QS01BC02