Details
Stereochemistry | ACHIRAL |
Molecular Formula | C15H16O2 |
Molecular Weight | 228.2863 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
COC1=CC2=C(C=C1)C=C(CCC(C)=O)C=C2
InChI
InChIKey=BLXXJMDCKKHMKV-UHFFFAOYSA-N
InChI=1S/C15H16O2/c1-11(16)3-4-12-5-6-14-10-15(17-2)8-7-13(14)9-12/h5-10H,3-4H2,1-2H3
Molecular Formula | C15H16O2 |
Molecular Weight | 228.2863 |
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/DB00461Curator's Comment: Description was created based on several sources, including
https://www.drugs.com/cdi/nabumetone.html
Sources: http://www.drugbank.ca/drugs/DB00461
Curator's Comment: Description was created based on several sources, including
https://www.drugs.com/cdi/nabumetone.html
Nabumetone is a naphthylalkanone. Is is a non-selective prostaglandin G/H synthase (a.k.a. cyclooxygenase or COX) inhibitor that acts on both prostaglandin G/H synthase 1 and 2 (COX-1 and -2). Prostaglandin G/H synthase catalyzes the conversion of arachidonic acid to prostaglandin G2 and prostaglandin G2 to prostaglandin H2. Prostaglandin H2 is the precursor to a number of prostaglandins involved in fever, pain, swelling, inflammation, and platelet aggregation. The parent compound is a prodrug that undergoes hepatic biotransformation to the active compound, 6-methoxy-2-naphthylacetic acid (6MNA). The analgesic, antipyretic and anti-inflammatory effects of NSAIDs occur as a result of decreased prostaglandin synthesis. The parent compound is a prodrug, which undergoes hepatic biotransformation to the active component, 6-methoxy-2-naphthylacetic acid (6MNA), that is a potent inhibitor of prostaglandin synthesis, most likely through binding to the COX-2 and COX-1 receptors. Nabumetone is used for acute and chronic treatment of signs and symptoms of osteoarthritis and rheumatoid arthritis. Nabumetone has been developed by Beecham. It is available under numerous brand names, such as Relafen, Relifex, and Gambaran.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL221 Sources: http://www.drugbank.ca/drugs/DB00461 |
149.0 µM [IC50] | ||
Target ID: CHEMBL230 Sources: http://www.drugbank.ca/drugs/DB00461 |
230.0 µM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Nabumetone Approved UseNabumetone tablets are indicated for relief of signs and symptoms of osteoarthritis and rheumatoid arthritis. Launch Date9.5921281E11 |
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Primary | Nabumetone Approved UseNabumetone tablets are indicated for relief of signs and symptoms of osteoarthritis and rheumatoid arthritis. Launch Date9.5921281E11 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
52.3 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2744071/ |
1000 mg 1 times / day steady-state, oral dose: 1000 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
6-METHOXY-2-NAPHTHYLACETIC ACID plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
66.7 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2744071/ |
1000 mg 1 times / day steady-state, oral dose: 1000 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
6-METHOXY-2-NAPHTHYLACETIC ACID plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
21.9 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2744071/ |
1000 mg single, oral dose: 1000 mg route of administration: Oral experiment type: SINGLE co-administered: |
6-METHOXY-2-NAPHTHYLACETIC ACID plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
33.7 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2744071/ |
1000 mg single, oral dose: 1000 mg route of administration: Oral experiment type: SINGLE co-administered: |
6-METHOXY-2-NAPHTHYLACETIC ACID plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
13.48 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12763542/ |
1000 mg single, oral dose: 1000 mg route of administration: Oral experiment type: SINGLE co-administered: |
NABUMETONE plasma | Homo sapiens population: HEALTHY age: UNKNOWN sex: MALE food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1022 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2744071/ |
1000 mg 1 times / day steady-state, oral dose: 1000 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
6-METHOXY-2-NAPHTHYLACETIC ACID plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
1270 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2744071/ |
1000 mg 1 times / day steady-state, oral dose: 1000 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
6-METHOXY-2-NAPHTHYLACETIC ACID plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
1120 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2744071/ |
1000 mg single, oral dose: 1000 mg route of administration: Oral experiment type: SINGLE co-administered: |
6-METHOXY-2-NAPHTHYLACETIC ACID plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
2150 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2744071/ |
1000 mg single, oral dose: 1000 mg route of administration: Oral experiment type: SINGLE co-administered: |
6-METHOXY-2-NAPHTHYLACETIC ACID plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
204.98 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12763542/ |
1000 mg single, oral dose: 1000 mg route of administration: Oral experiment type: SINGLE co-administered: |
NABUMETONE plasma | Homo sapiens population: HEALTHY age: UNKNOWN sex: MALE food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
27.5 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2744071/ |
1000 mg 1 times / day steady-state, oral dose: 1000 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
6-METHOXY-2-NAPHTHYLACETIC ACID plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
34.2 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2744071/ |
1000 mg 1 times / day steady-state, oral dose: 1000 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
6-METHOXY-2-NAPHTHYLACETIC ACID plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
26.3 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2744071/ |
1000 mg single, oral dose: 1000 mg route of administration: Oral experiment type: SINGLE co-administered: |
6-METHOXY-2-NAPHTHYLACETIC ACID plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
38.8 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2744071/ |
1000 mg single, oral dose: 1000 mg route of administration: Oral experiment type: SINGLE co-administered: |
6-METHOXY-2-NAPHTHYLACETIC ACID plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
16.82 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12763542/ |
1000 mg single, oral dose: 1000 mg route of administration: Oral experiment type: SINGLE co-administered: |
NABUMETONE plasma | Homo sapiens population: HEALTHY age: UNKNOWN sex: MALE food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
2 g 1 times / day steady, oral (max) Recommended Dose: 2 g, 1 times / day Route: oral Route: steady Dose: 2 g, 1 times / day Sources: Page: 9 |
unhealthy, adult n = 1677 Health Status: unhealthy Condition: rheumatoid arthritis and osteoarthritis Age Group: adult Sex: unknown Population Size: 1677 Sources: Page: 9 |
Disc. AE: Diarrhea, Dyspepsia... AEs leading to discontinuation/dose reduction: Diarrhea (1.3%) Sources: Page: 9Dyspepsia (0.8%) Abdominal pain (1.1%) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Dyspepsia | 0.8% Disc. AE |
2 g 1 times / day steady, oral (max) Recommended Dose: 2 g, 1 times / day Route: oral Route: steady Dose: 2 g, 1 times / day Sources: Page: 9 |
unhealthy, adult n = 1677 Health Status: unhealthy Condition: rheumatoid arthritis and osteoarthritis Age Group: adult Sex: unknown Population Size: 1677 Sources: Page: 9 |
Abdominal pain | 1.1% Disc. AE |
2 g 1 times / day steady, oral (max) Recommended Dose: 2 g, 1 times / day Route: oral Route: steady Dose: 2 g, 1 times / day Sources: Page: 9 |
unhealthy, adult n = 1677 Health Status: unhealthy Condition: rheumatoid arthritis and osteoarthritis Age Group: adult Sex: unknown Population Size: 1677 Sources: Page: 9 |
Diarrhea | 1.3% Disc. AE |
2 g 1 times / day steady, oral (max) Recommended Dose: 2 g, 1 times / day Route: oral Route: steady Dose: 2 g, 1 times / day Sources: Page: 9 |
unhealthy, adult n = 1677 Health Status: unhealthy Condition: rheumatoid arthritis and osteoarthritis Age Group: adult Sex: unknown Population Size: 1677 Sources: Page: 9 |
PubMed
Title | Date | PubMed |
---|---|---|
Rofecoxib: a review of its use in the management of osteoarthritis, acute pain and rheumatoid arthritis. | 2001 |
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Risk of upper gastrointestinal bleeding and perforation associated with low-dose aspirin as plain and enteric-coated formulations. | 2001 |
|
[Laparoscopic splenectomy in pediatric hematologic diseases]. | 2001 Apr |
|
A multicenter, randomized, controlled trial to evaluate the safety profile, tolerability, and efficacy of rofecoxib in advanced elderly patients with osteoarthritis. | 2001 Apr |
|
Inhibitors of cyclooxygenase-2 (COX-2) suppressed the proliferation and differentiation of human leukaemia cell lines. | 2001 Aug |
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Cyclooxygenase selectivity of non-steroid anti-inflammatory drugs in humans: ex vivo evaluation. | 2001 Aug 24 |
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Effects of NSAIDs on cryoprobe-induced gastric ulcer healing in rats. | 2001 Dec |
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Management of nonsteroidal anti-inflammatory drug-related peptic ulcer bleeding. | 2001 Jan 8 |
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Association of immunological disorders in lethal side effect of NSAIDs on beta-glucan-administered mice. | 2001 Jul |
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The effects of nabumetone, a cyclooxygenase-2 inhibitor, on cisplatin-induced 5-hydroxytryptamine release from the isolated rat ileum. | 2001 Jul-Aug |
|
Prolonged activation of mitogen-activated protein kinases during NSAID-induced apoptosis in HT-29 colon cancer cells. | 2001 Jun |
|
[Evaluation of early biomarkers of cartilage degeneration in the diagnosis and clinico-therapeutic monitoring of primary osteoarthrosis]. | 2001 May-Jun |
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2, 4-diamino-6- hydroxy pyrimidine inhibits NSAIDs induced nitrosyl-complex EPR signals and ulcer in rat jejunum. | 2002 Apr 18 |
|
Drug-induced erythroderma with high fever. | 2002 Feb |
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A comparison of the effects of nabumetone vs meloxicam on serum thromboxane B2 and platelet function in healthy volunteers. | 2002 Jun |
|
In vitro investigation of the effects of cyclooxygenase-2 inhibitors on contractile activity of the equine dorsal and ventral colon. | 2002 Nov |
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Drug-induced erythroderma with high fever--is it drug hypersensitivity syndrome? | 2003 Apr |
|
An open label study to establish dosing recommendations for nabumetone in juvenile rheumatoid arthritis. | 2003 Apr |
|
[Nabumetone is an alternative]. | 2003 Apr 24 |
|
Selection of drugs to test the specificity of the Tg.AC assay by screening for induction of the gadd153 promoter in vitro. | 2003 Aug |
|
Effects of nabumetone, celecoxib, and ibuprofen on blood pressure control in hypertensive patients on angiotensin converting enzyme inhibitors. | 2003 Feb |
|
Analysis of nabumetone in human plasma by HPLC. Application to single dose pharmacokinetic studies. | 2003 Jun 1 |
|
Development of apoptosis-resistant dihydrofolate reductase-deficient Chinese hamster ovary cell line. | 2003 Jun 30 |
|
[Meta-analysis on the effect and adverse reaction on patients with osteoarthritis and rheumatoid arthritis treated with non-steroidal anti-inflammatory drugs]. | 2003 Nov |
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Selective COX-2 inhibition and cardiovascular effects: a review of the rofecoxib development program. | 2003 Oct |
|
Spontaneous reports of hypertension leading to hospitalisation in association with rofecoxib, celecoxib, nabumetone and oxaprozin. | 2004 |
|
In vitro investigation of the effects of nonsteroidal anti-inflammatory drugs, prostaglandin E2, and prostaglandin F2alpha on contractile activity of the third compartment of the stomach of llamas. | 2004 Feb |
|
General principles of pharmaceutical solid polymorphism: a supramolecular perspective. | 2004 Feb 23 |
|
Risk factors of adverse drug reaction from non-steroidal anti-inflammatory drugs in Shanghai patients with arthropathy. | 2004 Mar |
|
Identification and determination of phase II nabumetone metabolites by high-performance liquid chromatography with photodiode array and mass spectrometric detection. | 2004 Mar 26 |
|
Effects of dietary anticarcinogens and nonsteroidal anti-inflammatory drugs on rat gastrointestinal UDP-glucuronosyltransferases. | 2004 Mar-Apr |
|
A population based historical cohort study of the mortality associated with nabumetone, Arthrotec, diclofenac, and naproxen. | 2004 May |
|
Efficacy and safety of rofecoxib 12.5 mg versus nabumetone 1,000 mg in patients with osteoarthritis of the knee: a randomized controlled trial. | 2004 May |
|
Calculation of cyclodextrin binding affinities: energy, entropy, and implications for drug design. | 2004 Nov |
|
[Reflections on COX, Vioxx and Relifex. Increased cardiovascular risk following selective COX-2 inhibition]. | 2004 Nov 25 |
|
Pulp-dentine complex changes and root resorption during intrusive orthodontic tooth movement in patients prescribed nabumetone. | 2005 Jan |
|
Prediction of genotoxicity of chemical compounds by statistical learning methods. | 2005 Jun |
|
Development and validation of a reversed-phase liquid chromatographic method for separation and simultaneous determination of COX-2 inhibitors in pharmaceuticals and its application to biological fluids. | 2005 Jun |
|
Comparative effects of indomethacin and nabumetone on urine and electrolyte output in conscious rats. | 2005 Nov |
|
Picture of the month. Stevens-Johnson Syndrome. | 2006 Aug |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.drugs.com/dosage/nabumetone.html
Initial dose: 1000 mg orally once a day
Maintenance dose: 1500 to 2000 mg orally per day in 1 or 2 divided doses
Maximum dose: 2000 mg/day
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/18976171
Nabumetone (50 ug/ml) was found to significantly increase COX-2 at mRNA levels but directly suppress the concentration of PGE2 in culture medium of human intervertebral disc cells.
Substance Class |
Chemical
Created
by
admin
on
Edited
Wed Jul 05 23:15:39 UTC 2023
by
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on
Wed Jul 05 23:15:39 UTC 2023
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Record UNII |
LW0TIW155Z
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Record Status |
Validated (UNII)
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Record Version |
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WHO-ATC |
M01AX01
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FDA ORPHAN DRUG |
255207
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NCI_THESAURUS |
C54679
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WHO-VATC |
QM01AX01
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NDF-RT |
N0000000160
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NDF-RT |
N0000175722
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NCI_THESAURUS |
C257
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NDF-RT |
N0000175721
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LIVERTOX |
NBK548909
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100000092274
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Nabumetone
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LW0TIW155Z
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7443
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31448
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1449518
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C47627
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SUB09107MIG
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M7698
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DB00461
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42924-53-8
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C035605
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4855
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CHEMBL1070
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4409
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DTXSID4045472
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7245
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NABUMETONE
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LW0TIW155Z
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758623
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1863
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Related Record | Type | Details | ||
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BASIS OF STRENGTH->SUBSTANCE |
ASSAY (HPLC)
EP
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BASIS OF STRENGTH->SUBSTANCE |
ASSAY (HPLC)
USP
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METABOLIC ENZYME -> SUBSTRATE | |||
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BINDER->LIGAND |
BINDING
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Related Record | Type | Details | ||
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METABOLITE -> PARENT |
URINE
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METABOLITE -> PARENT | |||
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METABOLITE -> PARENT |
URINE
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METABOLITE ACTIVE -> PARENT |
has anti-inflammatory activity in animals; more potent inhibitor of prostaglandin synthesis than nabumetone
MAJOR
PLASMA
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Related Record | Type | Details | ||
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
UNSPECIFIED
EP
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IMPURITY -> PARENT |
UNSPECIFIED
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
UNSPECIFIED
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
UNSPECIFIED
EP
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IMPURITY -> PARENT |
UNSPECIFIED
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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Volume of Distribution | PHARMACOKINETIC |
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Tmax | PHARMACOKINETIC |
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AT STEADY-STATE |
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Tmax | PHARMACOKINETIC |
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DOSE |
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