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Details

Stereochemistry RACEMIC
Molecular Formula C19H20N2O3
Molecular Weight 324.3744
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of OXYPHENBUTAZONE ANHYDROUS

SMILES

CCCCC1C(=O)N(c2ccccc2)N(c3ccc(cc3)O)C1=O

InChI

InChIKey=HFHZKZSRXITVMK-UHFFFAOYSA-N
InChI=1S/C19H20N2O3/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

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 But this drug was withdrawn from markets due to bone marrow suppression.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

-2.84947186E11
Palliative
TANDEARIL

Approved Use

Unknown

Launch Date

-2.84947186E11
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
Oxyphenbutazone and aplastic anemia.
1972 Nov
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
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 ANHYDROUS
Common Name English
CROVARIL
Brand Name English
4-BUTYL-1-(P-HYDROXYPHENYL)-2-PHENYL-3,5-PYRAZOLIDINEDIONE
Common Name English
3,5-PYRAZOLIDINEDIONE, 4-BUTYL-1-(4-HYDROXYPHENYL)-2-PHENYL-
Systematic Name English
G-27202
Code English
3,5-PYRAZOLIDINEDIONE, 4-BUTYL-1-(P-HYDROXYPHENYL)-2-PHENYL-
Systematic Name English
CALIFORNIT
Brand Name English
OXYPHENBUTAZONE [WHO-DD]
Common Name English
OXYPHENBUTAZONE [INN]
Common Name English
VISUBUTINA
Brand Name English
RAPOSTAN
Brand Name English
FLOGITOLO
Brand Name English
NSC-526053
Code English
(+/-)-OXYPHENBUTAZONE ANHYDROUS
Common Name English
NEO-FARMADOL
Brand Name English
OXAZOLIDIN
Systematic Name English
SUGANRIL
Common Name English
FLOGORIL
Brand Name English
OXYPHENBUTAZONE [MI]
Common Name English
OXYPHENBUTAZONE ANHYDROUS, (+/-)-
Common Name English
RO-04-4410
Code English
OXALID
Brand Name English
FRABEL
Brand Name English
TANDEARIL
Brand Name English
OXYPHENBUTAZONE [HSDB]
Common Name English
REOZON
Brand Name English
Classification Tree Code System Code
NCI_THESAURUS C257
Created by admin on Sat Jun 26 12:04:11 UTC 2021 , Edited by admin on Sat Jun 26 12:04:11 UTC 2021
WHO-ATC M02AA04
Created by admin on Sat Jun 26 12:04:11 UTC 2021 , Edited by admin on Sat Jun 26 12:04:11 UTC 2021
WHO-ATC S01BC02
Created by admin on Sat Jun 26 12:04:11 UTC 2021 , Edited by admin on Sat Jun 26 12:04:11 UTC 2021
WHO-ATC M01AA03
Created by admin on Sat Jun 26 12:04:11 UTC 2021 , Edited by admin on Sat Jun 26 12:04:11 UTC 2021
Code System Code Type Description
EVMPD
SUB09572MIG
Created by admin on Sat Jun 26 12:04:11 UTC 2021 , Edited by admin on Sat Jun 26 12:04:11 UTC 2021
PRIMARY
PUBCHEM
4641
Created by admin on Sat Jun 26 12:04:11 UTC 2021 , Edited by admin on Sat Jun 26 12:04:11 UTC 2021
PRIMARY
HSDB
3144
Created by admin on Sat Jun 26 12:04:11 UTC 2021 , Edited by admin on Sat Jun 26 12:04:11 UTC 2021
PRIMARY
EPA CompTox
129-20-4
Created by admin on Sat Jun 26 12:04:11 UTC 2021 , Edited by admin on Sat Jun 26 12:04:11 UTC 2021
PRIMARY
WIKIPEDIA
Rapostan
Created by admin on Sat Jun 26 12:04:11 UTC 2021 , Edited by admin on Sat Jun 26 12:04:11 UTC 2021
PRIMARY
INN
783
Created by admin on Sat Jun 26 12:04:11 UTC 2021 , Edited by admin on Sat Jun 26 12:04:11 UTC 2021
PRIMARY
MERCK INDEX
M8341
Created by admin on Sat Jun 26 12:04:11 UTC 2021 , Edited by admin on Sat Jun 26 12:04:11 UTC 2021
PRIMARY Merck Index
ECHA (EC/EINECS)
204-936-2
Created by admin on Sat Jun 26 12:04:11 UTC 2021 , Edited by admin on Sat Jun 26 12:04:11 UTC 2021
PRIMARY
CAS
129-20-4
Created by admin on Sat Jun 26 12:04:11 UTC 2021 , Edited by admin on Sat Jun 26 12:04:11 UTC 2021
PRIMARY
NCI_THESAURUS
C74597
Created by admin on Sat Jun 26 12:04:11 UTC 2021 , Edited by admin on Sat Jun 26 12:04:11 UTC 2021
PRIMARY
FDA UNII
A7D84513GV
Created by admin on Sat Jun 26 12:04:11 UTC 2021 , Edited by admin on Sat Jun 26 12:04:11 UTC 2021
PRIMARY