Details
Stereochemistry | ACHIRAL |
Molecular Formula | C12H11NO |
Molecular Weight | 185.2223 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
Cc1ccc(=O)n(c1)-c2ccccc2
InChI
InChIKey=ISWRGOKTTBVCFA-UHFFFAOYSA-N
InChI=1S/C12H11NO/c1-10-7-8-12(14)13(9-10)11-5-3-2-4-6-11/h2-9H,1H3
Molecular Formula | C12H11NO |
Molecular Weight | 185.2223 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
DescriptionCurator's Comment:: Description was created based on several sources, including
http://www.ncbi.nlm.nih.gov/pubmed/?term=12010989;
http://www.ncbi.nlm.nih.gov/pubmed/?term=9435445;
https://en.wikipedia.org/wiki/Pirfenidone
Curator's Comment:: Description was created based on several sources, including
http://www.ncbi.nlm.nih.gov/pubmed/?term=12010989;
http://www.ncbi.nlm.nih.gov/pubmed/?term=9435445;
https://en.wikipedia.org/wiki/Pirfenidone
Pirfenidone is a synthetic antifibrotic agent indicated for the treatment of idiopathic pulmonary fibrosis as Esbriet. Pirfenidone inhibits fibroblast, epidermal, platelet-derived, and transforming beta-1 growth factors. It also inhibits DNA synthesis and the production of mRNA for collagen types I and III, resulting in a reduction in radiation-induced fibrosis. Pirfenidone has demonstrated activity in multiple fibrotic conditions however the exact mechanism of action of pirfenidone in the treatment of IPF has not been established.
CNS Activity
Originator
Approval Year
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
6560 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/28808905 |
801 mg single, oral dose: 801 mg route of administration: Oral experiment type: SINGLE co-administered: |
PIRFENIDONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: HIGH-FAT |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
98000 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/28808905 |
801 mg single, oral dose: 801 mg route of administration: Oral experiment type: SINGLE co-administered: |
PIRFENIDONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: HIGH-FAT |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
2.75 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/28808905 |
801 mg single, oral dose: 801 mg route of administration: Oral experiment type: SINGLE co-administered: |
PIRFENIDONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: HIGH-FAT |
|
3 h |
PIRFENIDONE plasma | Homo sapiens population: HEALTHY age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
42% |
PIRFENIDONE plasma | Homo sapiens population: HEALTHY age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
2403 mg 1 times / day steady, oral Recommended Dose: 2403 mg, 1 times / day Route: oral Route: steady Dose: 2403 mg, 1 times / day Sources: |
unhealthy, 67 years (range: 40 - 80 years) n = 623 Health Status: unhealthy Condition: idiopathic pulmonary fibrosis Age Group: 67 years (range: 40 - 80 years) Sex: M+F Population Size: 623 Sources: |
Disc. AE: Rash, Nausea... AEs leading to discontinuation/dose reduction: Rash (1.3%) Sources: Nausea (1.1%) Rash (3%) Nausea (3%) Diarrhea (3%) Photosensitivity reaction (3%) |
2403 mg 1 times / day steady, oral Recommended Dose: 2403 mg, 1 times / day Route: oral Route: steady Dose: 2403 mg, 1 times / day Sources: Page: p. 23 |
unhealthy, 67 years (range: 40 - 80 years) n = 623 Health Status: unhealthy Condition: idiopathic pulmonary fibrosis Age Group: 67 years (range: 40 - 80 years) Sex: M+F Population Size: 623 Sources: Page: p. 23 |
Disc. AE: Weight decreased, Photosensitivity reaction... AEs leading to discontinuation/dose reduction: Weight decreased (0.8%) Sources: Page: p. 23Photosensitivity reaction (0.6%) Respiratory failure (0.5%) Hepatic enzyme increased (0.5%) Bladder cancer (0.5%) Vomiting (0.3%) GERD (0.3%) Malaise (0.3%) Dysgeusia (0.3%) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Nausea | 1.1% Disc. AE |
2403 mg 1 times / day steady, oral Recommended Dose: 2403 mg, 1 times / day Route: oral Route: steady Dose: 2403 mg, 1 times / day Sources: |
unhealthy, 67 years (range: 40 - 80 years) n = 623 Health Status: unhealthy Condition: idiopathic pulmonary fibrosis Age Group: 67 years (range: 40 - 80 years) Sex: M+F Population Size: 623 Sources: |
Rash | 1.3% Disc. AE |
2403 mg 1 times / day steady, oral Recommended Dose: 2403 mg, 1 times / day Route: oral Route: steady Dose: 2403 mg, 1 times / day Sources: |
unhealthy, 67 years (range: 40 - 80 years) n = 623 Health Status: unhealthy Condition: idiopathic pulmonary fibrosis Age Group: 67 years (range: 40 - 80 years) Sex: M+F Population Size: 623 Sources: |
Diarrhea | 3% Disc. AE |
2403 mg 1 times / day steady, oral Recommended Dose: 2403 mg, 1 times / day Route: oral Route: steady Dose: 2403 mg, 1 times / day Sources: |
unhealthy, 67 years (range: 40 - 80 years) n = 623 Health Status: unhealthy Condition: idiopathic pulmonary fibrosis Age Group: 67 years (range: 40 - 80 years) Sex: M+F Population Size: 623 Sources: |
Nausea | 3% Disc. AE |
2403 mg 1 times / day steady, oral Recommended Dose: 2403 mg, 1 times / day Route: oral Route: steady Dose: 2403 mg, 1 times / day Sources: |
unhealthy, 67 years (range: 40 - 80 years) n = 623 Health Status: unhealthy Condition: idiopathic pulmonary fibrosis Age Group: 67 years (range: 40 - 80 years) Sex: M+F Population Size: 623 Sources: |
Photosensitivity reaction | 3% Disc. AE |
2403 mg 1 times / day steady, oral Recommended Dose: 2403 mg, 1 times / day Route: oral Route: steady Dose: 2403 mg, 1 times / day Sources: |
unhealthy, 67 years (range: 40 - 80 years) n = 623 Health Status: unhealthy Condition: idiopathic pulmonary fibrosis Age Group: 67 years (range: 40 - 80 years) Sex: M+F Population Size: 623 Sources: |
Rash | 3% Disc. AE |
2403 mg 1 times / day steady, oral Recommended Dose: 2403 mg, 1 times / day Route: oral Route: steady Dose: 2403 mg, 1 times / day Sources: |
unhealthy, 67 years (range: 40 - 80 years) n = 623 Health Status: unhealthy Condition: idiopathic pulmonary fibrosis Age Group: 67 years (range: 40 - 80 years) Sex: M+F Population Size: 623 Sources: |
Dysgeusia | 0.3% Disc. AE |
2403 mg 1 times / day steady, oral Recommended Dose: 2403 mg, 1 times / day Route: oral Route: steady Dose: 2403 mg, 1 times / day Sources: Page: p. 23 |
unhealthy, 67 years (range: 40 - 80 years) n = 623 Health Status: unhealthy Condition: idiopathic pulmonary fibrosis Age Group: 67 years (range: 40 - 80 years) Sex: M+F Population Size: 623 Sources: Page: p. 23 |
GERD | 0.3% Disc. AE |
2403 mg 1 times / day steady, oral Recommended Dose: 2403 mg, 1 times / day Route: oral Route: steady Dose: 2403 mg, 1 times / day Sources: Page: p. 23 |
unhealthy, 67 years (range: 40 - 80 years) n = 623 Health Status: unhealthy Condition: idiopathic pulmonary fibrosis Age Group: 67 years (range: 40 - 80 years) Sex: M+F Population Size: 623 Sources: Page: p. 23 |
Malaise | 0.3% Disc. AE |
2403 mg 1 times / day steady, oral Recommended Dose: 2403 mg, 1 times / day Route: oral Route: steady Dose: 2403 mg, 1 times / day Sources: Page: p. 23 |
unhealthy, 67 years (range: 40 - 80 years) n = 623 Health Status: unhealthy Condition: idiopathic pulmonary fibrosis Age Group: 67 years (range: 40 - 80 years) Sex: M+F Population Size: 623 Sources: Page: p. 23 |
Vomiting | 0.3% Disc. AE |
2403 mg 1 times / day steady, oral Recommended Dose: 2403 mg, 1 times / day Route: oral Route: steady Dose: 2403 mg, 1 times / day Sources: Page: p. 23 |
unhealthy, 67 years (range: 40 - 80 years) n = 623 Health Status: unhealthy Condition: idiopathic pulmonary fibrosis Age Group: 67 years (range: 40 - 80 years) Sex: M+F Population Size: 623 Sources: Page: p. 23 |
Bladder cancer | 0.5% Disc. AE |
2403 mg 1 times / day steady, oral Recommended Dose: 2403 mg, 1 times / day Route: oral Route: steady Dose: 2403 mg, 1 times / day Sources: Page: p. 23 |
unhealthy, 67 years (range: 40 - 80 years) n = 623 Health Status: unhealthy Condition: idiopathic pulmonary fibrosis Age Group: 67 years (range: 40 - 80 years) Sex: M+F Population Size: 623 Sources: Page: p. 23 |
Hepatic enzyme increased | 0.5% Disc. AE |
2403 mg 1 times / day steady, oral Recommended Dose: 2403 mg, 1 times / day Route: oral Route: steady Dose: 2403 mg, 1 times / day Sources: Page: p. 23 |
unhealthy, 67 years (range: 40 - 80 years) n = 623 Health Status: unhealthy Condition: idiopathic pulmonary fibrosis Age Group: 67 years (range: 40 - 80 years) Sex: M+F Population Size: 623 Sources: Page: p. 23 |
Respiratory failure | 0.5% Disc. AE |
2403 mg 1 times / day steady, oral Recommended Dose: 2403 mg, 1 times / day Route: oral Route: steady Dose: 2403 mg, 1 times / day Sources: Page: p. 23 |
unhealthy, 67 years (range: 40 - 80 years) n = 623 Health Status: unhealthy Condition: idiopathic pulmonary fibrosis Age Group: 67 years (range: 40 - 80 years) Sex: M+F Population Size: 623 Sources: Page: p. 23 |
Photosensitivity reaction | 0.6% Disc. AE |
2403 mg 1 times / day steady, oral Recommended Dose: 2403 mg, 1 times / day Route: oral Route: steady Dose: 2403 mg, 1 times / day Sources: Page: p. 23 |
unhealthy, 67 years (range: 40 - 80 years) n = 623 Health Status: unhealthy Condition: idiopathic pulmonary fibrosis Age Group: 67 years (range: 40 - 80 years) Sex: M+F Population Size: 623 Sources: Page: p. 23 |
Weight decreased | 0.8% Disc. AE |
2403 mg 1 times / day steady, oral Recommended Dose: 2403 mg, 1 times / day Route: oral Route: steady Dose: 2403 mg, 1 times / day Sources: Page: p. 23 |
unhealthy, 67 years (range: 40 - 80 years) n = 623 Health Status: unhealthy Condition: idiopathic pulmonary fibrosis Age Group: 67 years (range: 40 - 80 years) Sex: M+F Population Size: 623 Sources: Page: p. 23 |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Drug as perpetrator
Drug as victim
PubMed
Title | Date | PubMed |
---|---|---|
Modulation of articular chondrocyte activity by pirfenidone. | 2003 |
|
Idiopathic pulmonary fibrosis: emerging concepts on pharmacotherapy. | 2004 Aug |
|
Transforming growth factor-beta: a clinical target for the treatment of diabetic nephropathy. | 2004 Dec |
|
Pirfenidone. | 2004 Feb |
|
Pirfenidone attenuates expression of HSP47 in murine bleomycin-induced pulmonary fibrosis. | 2004 Jul |
|
Prevention of progressive fibrosis in chronic renal diseases: antifibrotic agents. | 2004 Jul-Aug |
|
Pirfenidone inhibits obliterative airway disease in a murine heterotopic tracheal transplant model. | 2004 Mar 15 |
|
Gateways to clinical trials. | 2004 May |
|
Potential nonhormonal therapeutics for medical treatment of leiomyomas. | 2004 May |
|
The anti-fibrotic effect of pirfenidone in rat liver fibrosis is mediated by downregulation of procollagen alpha1(I), TIMP-1 and MMP-2. | 2004 Nov |
|
Pirfenidone inhibits the induction of iNOS stimulated by interleukin-1beta at a step of NF-kappaB DNA binding in hepatocytes. | 2004 Nov |
|
Pharmacokinetics of orally administered pirfenidone in male and female beagles. | 2004 Oct |
|
Effect of pirfenidone on induction of chemokines in rat hepatocytes. | 2004 Sep |
|
Effects of pirfenidone on endotoxin-induced liver injury after partial hepatectomy in rats. | 2004 Sep |
|
Pirfenidone protects endotoxin-induced liver injury after hepatic ischemia in rats. | 2004 Sep |
|
Primary progressive multiple sclerosis : current and future treatment options. | 2005 |
|
Protection of pirfenidone against an early phase of oleic acid-induced acute lung injury in rats. | 2005 Apr |
|
Retardation of kidney failure -- applying principles to practice. | 2005 Jan |
|
Pirfenidone and candesartan ameliorate morphological damage in mild chronic anti-GBM nephritis in rats. | 2005 Jan |
|
The novel antifibrotic agent pirfenidone attenuates the profibrotic environment generated by calcineurin inhibitors in the rat salt-depletion model. | 2005 Jan-Feb |
|
[Drug treatments for idiopathic pulmonary fibrosis]. | 2005 Jun |
|
Treatment of idiopathic pulmonary fibrosis: is there anything new? | 2005 Jun |
|
Pirfenidone inhibits lung allograft fibrosis through L-arginine-arginase pathway. | 2005 Jun |
|
Expression of HSP47 in usual interstitial pneumonia and nonspecific interstitial pneumonia. | 2005 Jun 14 |
|
[Interstitial pneumonia]. | 2005 May |
|
Double-blind, placebo-controlled trial of pirfenidone in patients with idiopathic pulmonary fibrosis. | 2005 May 1 |
|
Pirfenidone for the treatment of idiopathic pulmonary fibrosis: therapeutic potential prompts further investigation. | 2005 Nov |
|
The questionable efficacy of pirfenidone in IPF. | 2005 Nov 1 |
|
Poor choice of primary outcome in a clinical trial of pirfenidone in patients with IPF. | 2005 Nov 1 |
|
Sequential testing for efficacy in clinical trials with non-transient effects. | 2005 Nov 15 |
|
Gateways to clinical trials. | 2005 Oct |
|
Pirfenidone inhibits obliterative airway disease in mouse tracheal allografts. | 2005 Oct |
|
Pirfenidone inhibits inflammatory responses and ameliorates allograft injury in a rat lung transplant model. | 2005 Sep |
|
Symptomatic and disease-modifying therapies for multiple sclerosis: recent developments: highlights of the 9th Annual Meeting of the Americas Committee for Treatment and Research in Multiple Sclerosis, October 3, 2004, Toronto, Ontario, Canada. | 2005 Winter |
|
Pulmonary fibrosis in hermansky-pudlak syndrome. a case report and review. | 2006 |
|
Pirfenidone and chronic progressive obliterative airway disease. | 2006 Apr |
|
[Pulmonary fibrosis--a therapeutic dilemma?]. | 2006 Apr 15 |
|
Simple determination of pirfenidone in rat plasma via high-performance liquid chromatography. | 2006 Dec |
|
EM703 improves bleomycin-induced pulmonary fibrosis in mice by the inhibition of TGF-beta signaling in lung fibroblasts. | 2006 Jan 27 |
|
Promising pharmacologic innovations in treating pulmonary fibrosis. | 2006 Jun |
|
[Newly developed therapeutic drugs for idiopathic interstitial pneumonias]. | 2006 Jun 10 |
|
Therapeutic management of idiopathic pulmonary fibrosis: an evidence-based approach. | 2006 Mar |
|
Pirfenidone: anti-fibrotic agent with a potential therapeutic role in the management of transplantation patients. | 2006 May 1 |
|
A pilot study in patients with established advanced liver fibrosis using pirfenidone. | 2006 Nov |
|
Pirfenidone prevents the development of a vulnerable substrate for atrial fibrillation in a canine model of heart failure. | 2006 Oct 17 |
|
Long-term administration of pirfenidone improves cardiac function in mdx mice. | 2006 Sep |
|
Pirfenidone modulates airway responsiveness, inflammation, and remodeling after repeated challenge. | 2006 Sep |
|
Influence of pirfenidone on airway hyperresponsiveness and inflammation in a Brown-Norway rat model of asthma. | 2007 |
|
A comparison of factors associated with collagen metabolism in different skeletal muscles from dystrophic (mdx) mice: impact of pirfenidone. | 2007 Feb |
|
Pirfenidone in patients with idiopathic pulmonary fibrosis (CAPACITY): two randomised trials. | 2011 May 21 |
Sample Use Guides
The recommended daily maintenance dosage is 801 mg (three 267 mg capsules) three times a day with food for a total of 2403 mg/day. Doses should be taken at the same
time each day. Upon initiation of treatment, titrate to the full dosage of nine capsules per day over a 14-day
period as follows: 1 capsule three times days 1 through 7; 2 capsules three times a day days 8 through 14; 3 capsules three times a day days 15 onward.
Route of Administration:
Oral
In Vitro Use Guide
Sources: http://www.ncbi.nlm.nih.gov/pubmed/?term=9435445
0.01, 0.1, 0.3, and 1.0 mg/mL in in cultured myometrial and leiomyoma smooth muscle cells.
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Jun 25 21:07:05 UTC 2021
by
admin
on
Fri Jun 25 21:07:05 UTC 2021
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Record UNII |
D7NLD2JX7U
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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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FDA ORPHAN DRUG |
727219
Created by
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EU-Orphan Drug |
EU/3/04/241
Created by
admin on Fri Jun 25 21:07:06 UTC 2021 , Edited by admin on Fri Jun 25 21:07:06 UTC 2021
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FDA ORPHAN DRUG |
436914
Created by
admin on Fri Jun 25 21:07:06 UTC 2021 , Edited by admin on Fri Jun 25 21:07:06 UTC 2021
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EMA ASSESSMENT REPORTS |
ESBRIET (AUTHORISED: IDIOPATHIC PULMONARY FIBROSIS)
Created by
admin on Fri Jun 25 21:07:06 UTC 2021 , Edited by admin on Fri Jun 25 21:07:06 UTC 2021
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NDF-RT |
N0000191420
Created by
admin on Fri Jun 25 21:07:06 UTC 2021 , Edited by admin on Fri Jun 25 21:07:06 UTC 2021
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NCI_THESAURUS |
C257
Created by
admin on Fri Jun 25 21:07:06 UTC 2021 , Edited by admin on Fri Jun 25 21:07:06 UTC 2021
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NCI_THESAURUS |
C797
Created by
admin on Fri Jun 25 21:07:06 UTC 2021 , Edited by admin on Fri Jun 25 21:07:06 UTC 2021
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WHO-ATC |
L04AX05
Created by
admin on Fri Jun 25 21:07:06 UTC 2021 , Edited by admin on Fri Jun 25 21:07:06 UTC 2021
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FDA ORPHAN DRUG |
177903
Created by
admin on Fri Jun 25 21:07:06 UTC 2021 , Edited by admin on Fri Jun 25 21:07:06 UTC 2021
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WHO-VATC |
QL04AX05
Created by
admin on Fri Jun 25 21:07:06 UTC 2021 , Edited by admin on Fri Jun 25 21:07:06 UTC 2021
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FDA ORPHAN DRUG |
411113
Created by
admin on Fri Jun 25 21:07:06 UTC 2021 , Edited by admin on Fri Jun 25 21:07:06 UTC 2021
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Code System | Code | Type | Description | ||
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C2635
Created by
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PRIMARY | |||
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D7NLD2JX7U
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PRIMARY | |||
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4224
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PRIMARY | |||
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3825
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PRIMARY | |||
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CHEMBL1256391
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PRIMARY | |||
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7532
Created by
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PRIMARY | |||
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M8876
Created by
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PRIMARY | Merck Index | ||
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PIRFENIDONE
Created by
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PRIMARY | |||
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40632
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PRIMARY | |||
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C093844
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PRIMARY | |||
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53179-13-8
Created by
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PRIMARY | |||
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8340
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1592254
Created by
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SUB09907MIG
Created by
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PRIMARY | |||
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53179-13-8
Created by
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PRIMARY | |||
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N0000007575
Created by
admin on Fri Jun 25 21:07:06 UTC 2021 , Edited by admin on Fri Jun 25 21:07:06 UTC 2021
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PRIMARY | Pyridones [Chemical/Ingredient] | ||
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DB04951
Created by
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PRIMARY | |||
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PIRESPA
Created by
admin on Fri Jun 25 21:07:06 UTC 2021 , Edited by admin on Fri Jun 25 21:07:06 UTC 2021
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PRIMARY | APPROVED OCTOBER 2008 |
Related Record | Type | Details | ||
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LABELED -> NON-LABELED | |||
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METABOLIC ENZYME -> SUBSTRATE |
MAJOR
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BINDER->LIGAND |
BINDING
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Related Record | Type | Details | ||
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METABOLITE INACTIVE -> PARENT |
In vitro profiling studies in hepatocytes and liver microsomes have shown that ESBRIET is primarily metabolized in the liver by CYP1A2 and multiple other CYPs (CYP2C9, 2C19, 2D6, and 2E1).
MAJOR
PLASMA; URINE
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ACTIVE MOIETY |
Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Volume of Distribution | PHARMACOKINETIC |
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MULTIPLE DOSE ADMINISTRATION |
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Tmax | PHARMACOKINETIC |
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ORAL ADMINISTRATION |
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Tmax | PHARMACOKINETIC |
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FED CONDITION |
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Biological Half-life | PHARMACOKINETIC |
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