Details
Stereochemistry | RACEMIC |
Molecular Formula | C23H20N2O3S |
Molecular Weight | 404.4834 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
c1ccc(cc1)N2C(=O)C(CCS(=O)c3ccccc3)C(=O)N2c4ccccc4
InChI
InChIKey=MBGGBVCUIVRRBF-UHFFFAOYSA-N
InChI=1S/C23H20N2O3S/c26-22-21(16-17-29(28)20-14-8-3-9-15-20)23(27)25(19-12-6-2-7-13-19)24(22)18-10-4-1-5-11-18/h1-15,21H,16-17H2
Molecular Formula | C23H20N2O3S |
Molecular Weight | 404.4834 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
DescriptionSources: http://www.drugbank.ca/drugs/DB01138Curator's Comment:: Description was created based on several sources, including
https://www.drugs.com/pro/anturane.html
Sources: http://www.drugbank.ca/drugs/DB01138
Curator's Comment:: Description was created based on several sources, including
https://www.drugs.com/pro/anturane.html
Sulfinpyrazone was approved by the U.S. Food and Drug Administration (FDA) on May 13, 1959. It was developed and marketed as Anturane® by Novartis. Sulfinpyrazone is an oral uricosuric agent (pyrazolone derivative) used to treat chronic or intermittent gouty arthritis. Sulfinpyrazone competitively inhibits the reabsorption of uric acid at the proximal convoluted tubule, thereby facilitating urinary excretion of uric acid and decreasing plasma urate concentrations. This is likely done through inhibition of the urate anion transporter (hURAT1) as well as the human organic anion transporter 4 (hOAT4). Sulfinpyrazone is not intended for the treatment of acute attacks because it lacks therapeutically useful analgesic and anti-inflammatory effects. Sulfinpyrazone and its sulfide metabolite possess COX inhibitory effects. Sulfinpyrazone has also been shown to be a UDP-glucuronsyltransferase inhibitor and a very potent CYP2C9 inhibitor. Sulfinpyrazone is also known to be a cystic fibrosis transmembrane conductance regulator (CFTR) inhibitor as well as an inhibitor of several multridrug resistance proteins (MRPs). Branded and generic forms of sulfinpyrazone have been discontinued in the US.
Originator
Sources: http://en.pharmacodia.com/yaodu/html/v1/chemicals/3533fdf780f8ba13f910d329d6da05d3.html
Curator's Comment:: was developed and marketed as Anturane® by Novartis. # Novartis
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL5748 Sources: http://www.drugbank.ca/drugs/DB01138 |
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Target ID: CHEMBL3004 Sources: http://www.drugbank.ca/drugs/DB01138 |
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Target ID: CHEMBL2046258 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10840050 |
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Target ID: CHEMBL6120 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17325024 |
100.0 µM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Anturane Approved UseAnturane is indicated for the treatment of:
Chronic gouty arthritis
Intermittent gouty arthritis Launch Date-3.35836807E11 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
13.4 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3987792/ |
400 mg 2 times / day multiple, oral dose: 400 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
SULFINPYRAZONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
26 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3987792/ |
400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered: |
SULFINPYRAZONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
2.2 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3987792/ |
400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered: |
SULFINPYRAZONE SULFONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
2 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3987792/ |
400 mg 2 times / day multiple, oral dose: 400 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
SULFINPYRAZONE SULFONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
53 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3987792/ |
400 mg 2 times / day multiple, oral dose: 400 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
SULFINPYRAZONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
191.9 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7059415/ |
400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered: |
SULFINPYRAZONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
116 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3987792/ |
400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered: |
SULFINPYRAZONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
79.6 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7059415/ |
200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered: |
SULFINPYRAZONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
13.4 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3987792/ |
400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered: |
SULFINPYRAZONE SULFONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
9.2 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3987792/ |
400 mg 2 times / day multiple, oral dose: 400 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
SULFINPYRAZONE SULFONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
16.5 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7059415/ |
400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered: |
SULFINPYRAZONE SULFONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
5.7 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7059415/ |
200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered: |
SULFINPYRAZONE SULFONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
9.96 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3987792/ |
400 mg 2 times / day multiple, oral dose: 400 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
SULFINPYRAZONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
4.17 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7059415/ |
400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered: |
SULFINPYRAZONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
3.8 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3987792/ |
400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered: |
SULFINPYRAZONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
3.79 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7059415/ |
200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered: |
SULFINPYRAZONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
3.6 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3987792/ |
400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered: |
SULFINPYRAZONE SULFONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
3.3 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3987792/ |
400 mg 2 times / day multiple, oral dose: 400 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
SULFINPYRAZONE SULFONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
3.8 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7059415/ |
400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered: |
SULFINPYRAZONE SULFONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
Doses
Dose | Population | Adverse events |
---|---|---|
1000 mg single, oral Overdose |
healthy, 24 n = 1 Health Status: healthy Age Group: 24 Sex: M Population Size: 1 Sources: |
Other AEs: Acute renal failure... |
1000 mg multiple, oral (max) Recommended Dose: 1000 mg Route: oral Route: multiple Dose: 1000 mg Sources: Page: p.2 |
unhealthy Health Status: unhealthy Condition: Thrombosis Sources: Page: p.2 |
Other AEs: Acute renal failure... Other AEs: Acute renal failure (low incidence) Sources: Page: p.2 |
400 mg 2 times / day multiple, oral (max) Recommended Dose: 400 mg, 2 times / day Route: oral Route: multiple Dose: 400 mg, 2 times / day Sources: Page: p.4 |
unhealthy Health Status: unhealthy Condition: Gouty arthritis Sources: Page: p.4 |
Disc. AE: Skin rash... AEs leading to discontinuation/dose reduction: Skin rash (rare) Sources: Page: p.4 |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Acute renal failure | 1000 mg single, oral Overdose |
healthy, 24 n = 1 Health Status: healthy Age Group: 24 Sex: M Population Size: 1 Sources: |
|
Acute renal failure | low incidence | 1000 mg multiple, oral (max) Recommended Dose: 1000 mg Route: oral Route: multiple Dose: 1000 mg Sources: Page: p.2 |
unhealthy Health Status: unhealthy Condition: Thrombosis Sources: Page: p.2 |
Skin rash | rare Disc. AE |
400 mg 2 times / day multiple, oral (max) Recommended Dose: 400 mg, 2 times / day Route: oral Route: multiple Dose: 400 mg, 2 times / day Sources: Page: p.4 |
unhealthy Health Status: unhealthy Condition: Gouty arthritis Sources: Page: p.4 |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://pubmed.ncbi.nlm.nih.gov/14977870/ |
weak | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/16337112/ Page: 6.0 |
yes [IC50 103 uM] | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/16381668/ Page: 6.0 |
yes [IC50 11 uM] | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/16381668/ Page: 6.0 |
yes [IC50 158 uM] | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/16381668/ Page: 6.0 |
yes [IC50 16 uM] | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/16381668/ Page: 6.0 |
yes [IC50 187 uM] | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/16381668/ Page: 6.0 |
yes [IC50 267 uM] | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/16381668/ Page: 6.0 |
yes [IC50 2741 uM] | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/16381668/ Page: 6.0 |
yes [IC50 402 uM] | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/12695538/ Page: 9.0 |
yes [IC50 420 uM] | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/16381668/ Page: 6.0 |
yes [IC50 46 uM] | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/16381668/ Page: 6.0 |
yes [IC50 58 uM] | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/16381668/ Page: 6.0 |
yes [IC50 651 uM] | |||
yes [Ki 230 uM] | ||||
Sources: https://pubmed.ncbi.nlm.nih.gov/11996015/ Page: 77.0 |
yes | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/10219967/ Page: 1.0 |
yes | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/11996015/ Page: 184.0 |
yes | |||
yes | ||||
yes |
PubMed
Title | Date | PubMed |
---|---|---|
Acute myelomonocytic leukaemia and multiple myeloma after sulphinpyrazone and colchicine treatment of gout. | 1976 Jul 10 |
|
Sulphinpyrazone-induced acute renal failure. | 1981 Feb 21 |
|
Sulfinpyrazone induced uric acid urolithiasis with acute renal failure. | 1981 Jul |
|
Sulphinpyrazone--induced decrease in renal function: a review of reports with discussion of pathogenesis. | 1982 |
|
Acute renal failure following sulfinpyrazone therapy. | 1982 Apr |
|
[Sulfinpyrazone-associated renal failure (author's transl)]. | 1982 Jul 9 |
|
Non oliguric acute renal failure after treatment with sulfinpyrazone. | 1982 May |
|
Transcoronary platelet thromboxane A2 formation without platelet trapping in patients with coronary stenosis-effect of sulphinpyrazone treatment. | 1983 Dec 30 |
|
Oliguric acute renal failure after treatment with sulfinpyrazone. | 1983 Jan |
|
Sulfinpyrazone-associated acute renal failure. | 1983 Jul |
|
Decrease in renal function due to sulphinpyrazone treatment early after myocardial infarction. | 1983 Mar |
|
Acute renal failure secondary to sulfinpyrazone treatment after myocardial infarction. | 1984 |
|
Sulfinpyrazone: risk for renal insufficiency. | 1984 Mar |
|
Development of an in vitro reporter gene assay to assess xenobiotic induction of the human CYP3A4 gene. | 1997 Oct-Dec |
|
Acute renal failure due to sulfinpyrazone. | 1998 May |
|
A reporter gene assay to assess the molecular mechanisms of xenobiotic-dependent induction of the human CYP3A4 gene in vitro. | 1999 Mar |
|
Comparison of furosemide and vinblastine secretion from cell lines overexpressing multidrug resistance protein (P-glycoprotein) and multidrug resistance-associated proteins (MRP1 and MRP2). | 2002 |
|
Essential requirements for substrate binding affinity and selectivity toward human CYP2 family enzymes. | 2003 Jan 1 |
|
Functional expression of the multidrug resistance protein 1 in microglia. | 2003 Oct |
|
Glutathione S-transferase M1 and multidrug resistance protein 1 act in synergy to protect melanoma cells from vincristine effects. | 2004 Apr |
|
Role of multidrug resistance protein 2 (MRP2, ABCC2) in alkylating agent detoxification: MRP2 potentiates glutathione S-transferase A1-1-mediated resistance to chlorambucil cytotoxicity. | 2004 Jan |
|
Regulation of CYP2B6 in primary human hepatocytes by prototypical inducers. | 2004 Mar |
|
Prediction of CYP2C9-mediated drug-drug interactions: a comparison using data from recombinant enzymes and human hepatocytes. | 2005 Nov |
|
Use of immortalized human hepatocytes to predict the magnitude of clinical drug-drug interactions caused by CYP3A4 induction. | 2006 Oct |
|
In silico prediction of pregnane X receptor activators by machine learning approaches. | 2007 Jan |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.drugs.com/dosage/anturane.html
Initial
200-400 mg daily in two divided doses, with meals or milk, gradually increasing when necessary to full maintenance dosage in one week.
Maintenance
400 mg daily, given in two divided doses, as above. This dosage may be increased to 800 mg daily, if necessary, and may sometimes be reduced to as low as 200 mg daily after the blood urate level has been controlled.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/10840050
Sulfinpyrazone (2.5 mM) inhibited the MRP5-mediated PMEA efflux from resistant 293/MRP5 cells
Substance Class |
Chemical
Created
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admin
on
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Fri Jun 25 21:16:10 UTC 2021
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on
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Record UNII |
V6OFU47K3W
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Validated (UNII)
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NCI_THESAURUS |
C921
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WHO-ATC |
M04AB02
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LIVERTOX |
913
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WHO-VATC |
QM04AB02
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200-357-4
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C47739
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57-96-5
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DB01138
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D013442
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M10349
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1637008
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10205
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SULFINPYRAZONE
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TARGET -> INHIBITOR | |||
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BINDER->LIGAND |
BINDING
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METABOLIC ENZYME -> INDUCER | |||
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METABOLIC ENZYME -> INDUCER | |||
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TRANSPORTER -> INHIBITOR | |||
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TARGET -> INHIBITOR |
Related Record | Type | Details | ||
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METABOLITE -> PARENT | |||
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METABOLITE -> PARENT |
Related Record | Type | Details | ||
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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Related Record | Type | Details | ||
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ACTIVE MOIETY |
Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Biological Half-life | PHARMACOKINETIC |
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