U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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 of OXYPHENBUTAZONE

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 But this drug was withdrawn from markets due to bone marrow suppression.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
TANDEARIL

Approved Use

Unknown

Launch Date

1960
Palliative
TANDEARIL

Approved Use

Unknown

Launch Date

1960
Palliative
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
21.42 μg/mL
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
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
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
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
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

AUC

ValueDoseCo-administeredAnalytePopulation
397.401 μg × h/mL
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
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
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
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
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

Doses

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

AEs

AESignificanceDosePopulation
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:
unhealthy, 48 years
n = 1
Health Status: unhealthy
Condition: progressive shoulder pain
Age Group: 48 years
Sex: F
Population Size: 1
Sources:
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:
unhealthy, 64 years
n = 1
Health Status: unhealthy
Condition: rheumatoid arthritis
Age Group: 64 years
Sex: F
Population Size: 1
Sources:
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
[Inhibitory effect of oxyphenbutazone against Mycobacterium tuberculosis in vitro].
1969 Feb
Oxyphenbutazone and aplastic anemia.
1972 Nov
Drug-induced blood dyscrasias in Sweden.
1973 Aug 11
[Acute myelogenous leukemia. Associated with oxyphenbutazone induced aplastic anemia].
1974 Aug 10
Further studies of the acute effects of phenylbutazone, oxyphenbutazone and indomethacin on the rat kidney.
1976 Apr
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
Study of fatal bone marrow depression with special reference to phenylbutazone and oxyphenbutazone.
1977 Jun 11
Oxyphenbutazone-induced sialadenitis, intrahepatic cholestasis and pancreatitis.
1985 Sep-Oct
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
Effects of commonly used non steroidal anti-inflammatory drugs on gastric mucosa. A clinical, endoscopic and histopathological study.
1990 Sep
Drug-associated acute pancreatitis: twenty-one years of spontaneous reporting in The Netherlands.
1999 Sep
Nonsteroidal anti-inflammatory drug sensitizes Mycobacterium tuberculosis to endogenous and exogenous antimicrobials.
2012 Oct 2
FDA-approved drugs and other compounds tested as inhibitors of human glutathione transferase P1-1.
2013 Sep 5
Patents

Sample Use Guides

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
ORANGE BOOK   VANDF  
USP  
Official 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
OXYPHENBUTAZONE MONOHYDRATE
MI  
Common Name English
Classification Tree Code System Code
WHO-VATC QS01BC02
Created by admin on Fri Dec 15 16:32:34 GMT 2023 , Edited by admin on Fri Dec 15 16:32:34 GMT 2023
WHO-ATC M01AA03
Created by admin on Fri Dec 15 16:32:34 GMT 2023 , Edited by admin on Fri Dec 15 16:32:34 GMT 2023
WHO-ATC S01BC02
Created by admin on Fri Dec 15 16:32:34 GMT 2023 , Edited by admin on Fri Dec 15 16:32:34 GMT 2023
WHO-VATC QM01AA03
Created by admin on Fri Dec 15 16:32:34 GMT 2023 , Edited by admin on Fri Dec 15 16:32:34 GMT 2023
WHO-VATC QM02AA04
Created by admin on Fri Dec 15 16:32:34 GMT 2023 , Edited by admin on Fri Dec 15 16:32:34 GMT 2023
WHO-ATC M02AA04
Created by admin on Fri Dec 15 16:32:34 GMT 2023 , Edited by admin on Fri Dec 15 16:32:34 GMT 2023
NCI_THESAURUS C257
Created by admin on Fri Dec 15 16:32:34 GMT 2023 , Edited by admin on Fri Dec 15 16:32:34 GMT 2023
Code System Code Type Description
SMS_ID
100000083307
Created by admin on Fri Dec 15 16:32:34 GMT 2023 , Edited by admin on Fri Dec 15 16:32:34 GMT 2023
PRIMARY
DRUG CENTRAL
2036
Created by admin on Fri Dec 15 16:32:34 GMT 2023 , Edited by admin on Fri Dec 15 16:32:34 GMT 2023
PRIMARY
MESH
D010113
Created by admin on Fri Dec 15 16:32:34 GMT 2023 , Edited by admin on Fri Dec 15 16:32:34 GMT 2023
PRIMARY
MERCK INDEX
m8341
Created by admin on Fri Dec 15 16:32:34 GMT 2023 , Edited by admin on Fri Dec 15 16:32:34 GMT 2023
PRIMARY Merck Index
CAS
7081-38-1
Created by admin on Fri Dec 15 16:32:34 GMT 2023 , Edited by admin on Fri Dec 15 16:32:34 GMT 2023
PRIMARY
NCI_THESAURUS
C66282
Created by admin on Fri Dec 15 16:32:34 GMT 2023 , Edited by admin on Fri Dec 15 16:32:34 GMT 2023
PRIMARY
PUBCHEM
104811
Created by admin on Fri Dec 15 16:32:34 GMT 2023 , Edited by admin on Fri Dec 15 16:32:34 GMT 2023
PRIMARY
CHEBI
76258
Created by admin on Fri Dec 15 16:32:34 GMT 2023 , Edited by admin on Fri Dec 15 16:32:34 GMT 2023
PRIMARY
FDA UNII
H806S4B3NS
Created by admin on Fri Dec 15 16:32:34 GMT 2023 , Edited by admin on Fri Dec 15 16:32:34 GMT 2023
PRIMARY
ChEMBL
CHEMBL1228
Created by admin on Fri Dec 15 16:32:34 GMT 2023 , Edited by admin on Fri Dec 15 16:32:34 GMT 2023
PRIMARY
DRUG BANK
DB03585
Created by admin on Fri Dec 15 16:32:34 GMT 2023 , Edited by admin on Fri Dec 15 16:32:34 GMT 2023
PRIMARY
CHEBI
76259
Created by admin on Fri Dec 15 16:32:34 GMT 2023 , Edited by admin on Fri Dec 15 16:32:34 GMT 2023
PRIMARY
RXCUI
7816
Created by admin on Fri Dec 15 16:32:34 GMT 2023 , Edited by admin on Fri Dec 15 16:32:34 GMT 2023
PRIMARY RxNorm
WIKIPEDIA
OXYPHENBUTAZONE
Created by admin on Fri Dec 15 16:32:34 GMT 2023 , Edited by admin on Fri Dec 15 16:32:34 GMT 2023
PRIMARY
NSC
757261
Created by admin on Fri Dec 15 16:32:34 GMT 2023 , Edited by admin on Fri Dec 15 16:32:34 GMT 2023
PRIMARY
EPA CompTox
DTXSID90991079
Created by admin on Fri Dec 15 16:32:34 GMT 2023 , Edited by admin on Fri Dec 15 16:32:34 GMT 2023
PRIMARY