Details
Stereochemistry | RACEMIC |
Molecular Formula | C19H20N2O3 |
Molecular Weight | 324.3737 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CCCCC1C(=O)N(N(C1=O)C2=CC=C(O)C=C2)C3=CC=CC=C3
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
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 But this drug was withdrawn from markets due to bone marrow suppression.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
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL2094253 Sources: https://www.ncbi.nlm.nih.gov/pubmed/3108222 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Palliative | TANDEARIL Approved UseUnknown Launch Date1960 |
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Palliative | TANDEARIL Approved UseUnknown Launch Date1960 |
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Palliative | Unknown Approved UseUnknown |
Cmax
Value | Dose | Co-administered | Analyte | Population |
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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 | Co-administered | 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: |
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
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: |
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: |
PubMed
Title | Date | PubMed |
---|---|---|
Oxyphenbutazone and aplastic anemia. | 1972 Nov |
|
[Acute myelogenous leukemia. Associated with oxyphenbutazone induced aplastic anemia]. | 1974 Aug 10 |
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Study of fatal bone marrow depression with special reference to phenylbutazone and oxyphenbutazone. | 1977 Jun 11 |
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Oxyphenbutazone-induced sialadenitis, intrahepatic cholestasis and pancreatitis. | 1985 Sep-Oct |
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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 |
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FDA-approved drugs and other compounds tested as inhibitors of human glutathione transferase P1-1. | 2013 Sep 5 |
Sample Use Guides
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/6616956
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.
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Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C257
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WHO-ATC |
M02AA04
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WHO-ATC |
S01BC02
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M01AA03
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76258
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SUB09572MIG
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4641
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76259
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3144
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DTXSID1045291
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Rapostan
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783
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m8341
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204-936-2
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129-20-4
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C74597
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A7D84513GV
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526053
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ACTIVE MOIETY
SALT/SOLVATE (PARENT)
SALT/SOLVATE (PARENT)