Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C21H26O5 |
Molecular Weight | 358.4281 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 6 / 6 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@@]12CC[C@](O)(C(=O)CO)[C@@]1(C)CC(=O)[C@@]3([H])[C@@]2([H])CCC4=CC(=O)C=C[C@]34C
InChI
InChIKey=XOFYZVNMUHMLCC-ZPOLXVRWSA-N
InChI=1S/C21H26O5/c1-19-7-5-13(23)9-12(19)3-4-14-15-6-8-21(26,17(25)11-22)20(15,2)10-16(24)18(14)19/h5,7,9,14-15,18,22,26H,3-4,6,8,10-11H2,1-2H3/t14-,15-,18+,19-,20-,21-/m0/s1
Molecular Formula | C21H26O5 |
Molecular Weight | 358.4281 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 6 / 6 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
Prednisone is a synthetic anti-inflammatory glucocorticoid derived from cortisone. Prednisone is a corticosteroid indicated as an anti-inflammatory or immunosuppressive agent allergic, dermatologic, gastrointestinal, hematologic, ophthalmologic, nervous system, renal, respiratory, rheumatologic, specific infectious diseases or conditions and organ transplantation; for the treatment of certain endocrine conditions; for palliation of certain neoplastic conditions. The pharmacological effects of prednisone which are due to its corticosteroid properties include: promotion of gluconeogenesis; increased deposition of glycogen in the liver; inhibition of the utilization of glucose; anti-insulin activity; increased catabolism of protein; increased lipolysis; stimulation of fat synthesis and storage; increased glomerular filtration rate and resulting increase in urinary excretion of urate (creatinine excretion remains unchanged); and increased calcium excretion. Depressed production of eosinophils and lymphocytes occurs, but erythropoiesis and production of polymorphonuclear leukocytes are stimulated. Inflammatory processes (edema, fibrin deposition, capillary dilatation, migration of leukocytes and phagocytosis) and the later stages of wound healing (capillary proliferation, deposition of collagen, cicatrization) are inhibited. Prednisone can stimulate secretion of various components of gastric juice. Suppression of the production of corticotropin may lead to suppression of endogenous corticosteroids. Prednisone has slight mineralocorticoid activity, whereby entry of sodium into cells and loss of intracellular potassium is stimulated. This is particularly evident in the kidney, where rapid ion exchange leads to sodium retention and hypertension. Prednisone is completely converted to the active metabolite prednisolone, which is further metabolized mainly in the liver and excreted in the urine as sulfate and glucuronide conjugates. The exposure of prednisolone is 4-6 fold higher than that of prednisone.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2034 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Palliative | RAYOS Approved UseRAYOS is a corticosteroid indicated as an anti-inflammatory or immunosuppressive agent for certain
allergic, dermatologic, gastrointestinal, hematologic, ophthalmologic, nervous system, renal, respiratory, rheumatologic, specific infectious diseases or conditions and organ transplantation; for the treatment of certain endocrine conditions; for palliation of certain neoplastic conditions Launch Date2012 |
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Palliative | RAYOS Approved UseRAYOS is a corticosteroid indicated as an anti-inflammatory or immunosuppressive agent for certain
allergic, dermatologic, gastrointestinal, hematologic, ophthalmologic, nervous system, renal, respiratory, rheumatologic, specific infectious diseases or conditions and organ transplantation; for the treatment of certain endocrine conditions; for palliation of certain neoplastic conditions Launch Date2012 |
|||
Palliative | RAYOS Approved UseRAYOS is a corticosteroid indicated as an anti-inflammatory or immunosuppressive agent for certain
allergic, dermatologic, gastrointestinal, hematologic, ophthalmologic, nervous system, renal, respiratory, rheumatologic, specific infectious diseases or conditions and organ transplantation; for the treatment of certain endocrine conditions; for palliation of certain neoplastic conditions Launch Date2012 |
|||
Palliative | RAYOS Approved UseRAYOS is a corticosteroid indicated as an anti-inflammatory or immunosuppressive agent for certain
allergic, dermatologic, gastrointestinal, hematologic, ophthalmologic, nervous system, renal, respiratory, rheumatologic, specific infectious diseases or conditions and organ transplantation; for the treatment of certain endocrine conditions; for palliation of certain neoplastic conditions Launch Date2012 |
|||
Palliative | RAYOS Approved UseRAYOS is a corticosteroid indicated as an anti-inflammatory or immunosuppressive agent for certain
allergic, dermatologic, gastrointestinal, hematologic, ophthalmologic, nervous system, renal, respiratory, rheumatologic, specific infectious diseases or conditions and organ transplantation; for the treatment of certain endocrine conditions; for palliation of certain neoplastic conditions Launch Date2012 |
|||
Palliative | RAYOS Approved UseRAYOS is a corticosteroid indicated as an anti-inflammatory or immunosuppressive agent for certain
allergic, dermatologic, gastrointestinal, hematologic, ophthalmologic, nervous system, renal, respiratory, rheumatologic, specific infectious diseases or conditions and organ transplantation; for the treatment of certain endocrine conditions; for palliation of certain neoplastic conditions Launch Date2012 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
15.4 μg/L EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/17925494 |
20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered: |
PREDNISONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
97 μg × h/L EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/17925494 |
20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered: |
PREDNISONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
3.85 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/17925494 |
20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered: |
PREDNISONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
50% EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/2199128 |
PREDNISONE plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
100 mg 1 times / day multiple, oral Highest studied dose Dose: 100 mg, 1 times / day Route: oral Route: multiple Dose: 100 mg, 1 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sources: |
|
5 mg 1 times / day steady, oral Recommended Dose: 5 mg, 1 times / day Route: oral Route: steady Dose: 5 mg, 1 times / day Sources: Page: p. 92 |
unhealthy, adult n = 144 Health Status: unhealthy Age Group: adult Population Size: 144 Sources: Page: p. 92 |
Disc. AE: Vertigo, Abdominal pain upper... AEs leading to discontinuation/dose reduction: Vertigo (1%) Sources: Page: p. 92Abdominal pain upper (1%) Gastroesophageal reflux disease (1%) Intestinal functional disorder (1%) Nausea (1%) Dizziness (1%) Aphasia (1%) Headache (1%) Renal pain (1%) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Abdominal pain upper | 1% Disc. AE |
5 mg 1 times / day steady, oral Recommended Dose: 5 mg, 1 times / day Route: oral Route: steady Dose: 5 mg, 1 times / day Sources: Page: p. 92 |
unhealthy, adult n = 144 Health Status: unhealthy Age Group: adult Population Size: 144 Sources: Page: p. 92 |
Aphasia | 1% Disc. AE |
5 mg 1 times / day steady, oral Recommended Dose: 5 mg, 1 times / day Route: oral Route: steady Dose: 5 mg, 1 times / day Sources: Page: p. 92 |
unhealthy, adult n = 144 Health Status: unhealthy Age Group: adult Population Size: 144 Sources: Page: p. 92 |
Dizziness | 1% Disc. AE |
5 mg 1 times / day steady, oral Recommended Dose: 5 mg, 1 times / day Route: oral Route: steady Dose: 5 mg, 1 times / day Sources: Page: p. 92 |
unhealthy, adult n = 144 Health Status: unhealthy Age Group: adult Population Size: 144 Sources: Page: p. 92 |
Gastroesophageal reflux disease | 1% Disc. AE |
5 mg 1 times / day steady, oral Recommended Dose: 5 mg, 1 times / day Route: oral Route: steady Dose: 5 mg, 1 times / day Sources: Page: p. 92 |
unhealthy, adult n = 144 Health Status: unhealthy Age Group: adult Population Size: 144 Sources: Page: p. 92 |
Headache | 1% Disc. AE |
5 mg 1 times / day steady, oral Recommended Dose: 5 mg, 1 times / day Route: oral Route: steady Dose: 5 mg, 1 times / day Sources: Page: p. 92 |
unhealthy, adult n = 144 Health Status: unhealthy Age Group: adult Population Size: 144 Sources: Page: p. 92 |
Intestinal functional disorder | 1% Disc. AE |
5 mg 1 times / day steady, oral Recommended Dose: 5 mg, 1 times / day Route: oral Route: steady Dose: 5 mg, 1 times / day Sources: Page: p. 92 |
unhealthy, adult n = 144 Health Status: unhealthy Age Group: adult Population Size: 144 Sources: Page: p. 92 |
Nausea | 1% Disc. AE |
5 mg 1 times / day steady, oral Recommended Dose: 5 mg, 1 times / day Route: oral Route: steady Dose: 5 mg, 1 times / day Sources: Page: p. 92 |
unhealthy, adult n = 144 Health Status: unhealthy Age Group: adult Population Size: 144 Sources: Page: p. 92 |
Renal pain | 1% Disc. AE |
5 mg 1 times / day steady, oral Recommended Dose: 5 mg, 1 times / day Route: oral Route: steady Dose: 5 mg, 1 times / day Sources: Page: p. 92 |
unhealthy, adult n = 144 Health Status: unhealthy Age Group: adult Population Size: 144 Sources: Page: p. 92 |
Vertigo | 1% Disc. AE |
5 mg 1 times / day steady, oral Recommended Dose: 5 mg, 1 times / day Route: oral Route: steady Dose: 5 mg, 1 times / day Sources: Page: p. 92 |
unhealthy, adult n = 144 Health Status: unhealthy Age Group: adult Population Size: 144 Sources: Page: p. 92 |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: - |
no | |||
Page: - |
no | |||
Page: - |
no | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/15979871/ Page: - |
no | |||
Page: - |
no | |||
Page: - |
no | |||
Page: - |
no | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/15979871/ Page: - |
yes |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: - |
major | |||
Page: - |
minor | |||
Page: - |
yes |
PubMed
Title | Date | PubMed |
---|---|---|
Cytogenetic studies in a patient with acute granulocytic leukemia of seven and one-half years duration. | 1975 Nov |
|
An unusual adverse reaction to self-medication with prednisone: an irrational crime during a fugue-state. | 1976-1977 |
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Spontaneous aortic rupture associated with chronic steroid therapy for rheumatoid arthritis in two cases. | 1979 Feb |
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Low-dose vincristine-associated bilateral vocal cord paralysis. | 1999 Oct |
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Lamotrigine as prophylaxis against steroid-induced mania. | 1999 Oct |
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Delayed generalized allergic reactions to corticosteroids. | 2000 |
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Acute neurotoxicity in children with B-lineage acute lymphoblastic leukemia (B-ALL) treated with intermediate risk protocols. | 2000 Nov |
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Leucocytoclastic vasculitis and indinavir. | 2000 Nov |
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Pulmonary mucosa-associated lymphoid tissue lymphoma in a patient with common variable immunodeficiency syndrome. | 2001 |
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Cyclophosphamide and antithymocyte globulin to condition patients with aplastic anemia for allogeneic marrow transplantations: the experience in four centers. | 2001 |
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Hodgkin's disease: clinical presentation and treatment. | 2001 |
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Current status of cytotoxic chemotherapy in hormone refractory prostate cancer. | 2001 Feb |
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The usefulness of quantitative orbital magnetic resonance imaging in Graves' ophthalmopathy. | 2001 Feb |
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Interstitial nephritis in patients with inflammatory bowel disease treated with mesalamine. | 2001 Feb |
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Recalcitrant allergic contact dermatitis from azathioprine tablets. | 2001 Feb |
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Idiopathic IgA nephropathy with segmental necrotizing lesions of the capillary wall. | 2001 Feb |
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Interferon alfa 2b as maintenance therapy in poor risk diffuse large B-cell lymphoma in complete remission after intensive CHOP-BLEO regimens. | 2001 Feb |
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Time course of 21-hydroxylase antibodies and long-term remission of subclinical autoimmune adrenalitis after corticosteroid therapy: case report. | 2001 Feb |
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Adult Gaucher disease in association with primary malignant bone tumors. | 2001 Feb 1 |
|
Long-term results of combined-modality therapy for locally advanced breast cancer with ipsilateral supraclavicular metastases: The University of Texas M.D. Anderson Cancer Center experience. | 2001 Feb 1 |
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Sample size calculations for the two-sample problem using the multiplicative intensity model. | 2001 Feb 28 |
|
Two-year effects of alendronate on bone mineral density and vertebral fracture in patients receiving glucocorticoids: a randomized, double-blind, placebo-controlled extension trial. | 2001 Jan |
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Nocardia pleural empyema complicating anti-Jo1 positive polymyositis during immunoglobulin and steroid therapy. | 2001 Jan |
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Plasmapheresis as an effective treatment for opsoclonus-myoclonus syndrome. | 2001 Jan |
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Longitudinal assessment of everolimus in de novo renal transplant recipients over the first post-transplant year: pharmacokinetics, exposure-response relationships, and influence on cyclosporine. | 2001 Jan |
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Persistent paraneoplastic neurologic syndrome after successful therapy of Hodgkin's disease. | 2001 Jan |
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A high serum-soluble interleukin-2 receptor level is associated with a poor outcome of aggressive non-Hodgkin's lymphoma. | 2001 Jan |
|
Multiple myeloma in elderly patients: presenting features and outcome. | 2001 Jan |
|
Immunosuppression as adjuvant therapy for biliary atresia. | 2001 Jan |
|
Biliary stricture secondary to donor B-cell lymphoma after orthotopic liver transplantation. | 2001 Jan |
|
Efficacy of parenteral methotrexate in refractory Crohn's disease. | 2001 Jan |
|
Diabetes insipidus and anterior pituitary insufficiency as presenting features of Wegener's granulomatosis. | 2001 Jan |
|
Cause of high variability in drug dissolution testing and its impact on setting tolerances. | 2001 Jan |
|
Dose-response analysis for radiotherapy delivered to patients with intermediate-grade and large-cell immunoblastic lymphomas that have completely responded to CHOP-based induction chemotherapy. | 2001 Jan 1 |
|
Flutamide versus prednisone in patients with prostate cancer symptomatically progressing after androgen-ablative therapy: a phase III study of the European organization for research and treatment of cancer genitourinary group. | 2001 Jan 1 |
|
High-dose therapy and autologous bone marrow transplantation for follicular lymphoma in first complete or partial remission: results of a phase II clinical trial. | 2001 Jan 15 |
|
Combined treatment of giant-cell arteritis with methotrexate and prednisone. a randomized, double-blind, placebo-controlled trial. | 2001 Jan 16 |
|
Ethnic differences in clinical response to corticosteroid treatment of acute renal allograft rejection. | 2001 Jan 27 |
|
Autologous bone marrow transplantation for aggressive non-Hodgkin's lymphoma: lessons learned and challenges remaining. | 2001 Jan 3 |
|
Use of biological markers of airway inflammation to detect the efficacy of nurse-delivered asthma education. | 2001 Jan-Feb |
|
Depression or hypoactive delirium? A report of ciprofloxacin-induced mental disorder in a patient with chronic obstructive pulmonary disease. | 2001 Jan-Feb |
Sample Use Guides
The initial dosage of RAYOS (prednisone) may vary from 5 to 60 mg per day depending on the specific disease entity being treated based on relative potency.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/8608650
Peripheral blood lymphocytes (PBL) or peripheral CD4(+) and CD8(+) T cell subsets were cultured in the presence of prednisone (PDN) at 10(-3)-10(-12)M concentrations for 72, 96 and 120h. Apoptosis is clearly increased by PDN and the apoptotic effect of PDN is stronger on CD8(+) than on CD4(+) T lymphocytes.
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 15:51:36 GMT 2023
by
admin
on
Fri Dec 15 15:51:36 GMT 2023
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Record UNII |
VB0R961HZT
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Record Status |
Validated (UNII)
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Record Version |
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-
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Classification Tree | Code System | Code | ||
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WHO-ATC |
H02AB07
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WHO-ATC |
A07EA03
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WHO-VATC |
QH02AB07
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NCI_THESAURUS |
C521
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IARC | Prednisone | ||
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WHO-VATC |
QH02AB57
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CFR |
21 CFR 522.1890
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LIVERTOX |
795
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NDF-RT |
N0000175450
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WHO-VATC |
QA07EA03
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NDF-RT |
N0000175576
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C770
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8640
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3168
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m9112
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PRIMARY | Merck Index | ||
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1559006
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VB0R961HZT
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8382
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536
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DB00635
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2253
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200-160-3
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7096
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SUB10020MIG
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VB0R961HZT
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1559505
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100000091943
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5865
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D011241
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DTXSID4021185
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Prednisone
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CHEMBL635
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10023
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53-03-2
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PREDNISONE
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METABOLIC ENZYME -> SUBSTRATE |
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METABOLITE -> PARENT |
MINOR
URINE
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METABOLITE -> PARENT |
MINOR
URINE
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METABOLITE -> PARENT |
MINOR
URINE
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METABOLITE ACTIVE -> PRODRUG |
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METABOLITE -> PARENT |
MINOR
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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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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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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Biological Half-life | PHARMACOKINETIC |
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MAXIMUM TOLERATED DOSE | TOXICITY |
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Volume of Distribution | PHARMACOKINETIC |
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Tmax | PHARMACOKINETIC |
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PREDNISOLONE (ACTIVE METABOLITE), ORAL PHARMACOKINETIC PHARMACOKINETIC |
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ORAL BIOAVAILABILITY | PHARMACOKINETIC |
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