Details
Stereochemistry | RACEMIC |
Molecular Formula | C17H20F6N2O3 |
Molecular Weight | 414.3427 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
FC(F)(F)COC1=CC(C(=O)NCC2CCCCN2)=C(OCC(F)(F)F)C=C1
InChI
InChIKey=DJBNUMBKLMJRSA-UHFFFAOYSA-N
InChI=1S/C17H20F6N2O3/c18-16(19,20)9-27-12-4-5-14(28-10-17(21,22)23)13(7-12)15(26)25-8-11-3-1-2-6-24-11/h4-5,7,11,24H,1-3,6,8-10H2,(H,25,26)
Molecular Formula | C17H20F6N2O3 |
Molecular Weight | 414.3427 |
Charge | 0 |
Count |
|
Stereochemistry | RACEMIC |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Optical Activity | ( + / - ) |
DescriptionSources: http://www.drugbank.ca/drugs/DB01195Curator's Comment: Description was created based on several sources, including
https://www.drugs.com/pro/flecainide.html
Sources: http://www.drugbank.ca/drugs/DB01195
Curator's Comment: Description was created based on several sources, including
https://www.drugs.com/pro/flecainide.html
Flecainide is a potent anti-arrhythmia agent, effective in a wide range of ventricular and atrial arrhythmias and tachycardias. Flecainide has local anesthetic activity and belongs to the membrane stabilizing (Class 1) group of antiarrhythmic agents; it has electrophysiologic effects characteristic of the IC class of antiarrhythmics. Flecainide acts on sodium channels on the neuronal cell membrane, limiting the spread of seizure activity and reducing seizure propagation. The antiarrhythmic actions are mediated through effects on sodium channels in Purkinje fibers. Flecainide is a sodium channel blocker, binding to voltage gated sodium channels. It stabilizes the neuronal membrane by inhibiting the ionic fluxes required for the initiation and conduction of impulses. Ventricular excitability is depressed and the stimulation threshold of the ventricle is increased during diastole. Flecainide is sold under the trade name Tambocor (manufactured by 3M pharmaceuticals). Flecainide went off-patent on February 10, 2004. In addition to being marketed as Tambocor, it is also available in generic version and under the trade names Almarytm, Apocard, Ecrinal, and Flécaine.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL1980 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21194571 |
67.2 µM [IC50] | ||
Target ID: CHEMBL2072 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20590641 |
18.0 µM [Ki] | ||
Target ID: CHEMBL240 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26159617 |
1.49 µM [IC50] | ||
Target ID: CHEMBL1964 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12875427 |
7.8 µM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Preventing | Flecainide Approved UseIn patients without structural heart disease, Flecainide is indicated for the prevention of
- paroxysmal supraventricular tachycardias (PSVT), including atrioventricular nodal reentrant tachycardia, atrioventricular reentrant tachycardia and other supraventricular tachycardias of unspecified mechanism associated with disabling symptoms
- paroxysmal atrial fibrillation/flutter (PAF) associated with disabling symptoms
Flecainide is also indicated for the prevention of
- documented ventricular arrhythmias, such as sustained ventricular tachycardia (sustained VT), that in the judgment of the physician, are lifethreatening. Launch Date2001 |
|||
Preventing | Flecainide Approved UseIn patients without structural heart disease, Flecainide is indicated for the prevention of
- paroxysmal supraventricular tachycardias (PSVT), including atrioventricular nodal reentrant tachycardia, atrioventricular reentrant tachycardia and other supraventricular tachycardias of unspecified mechanism associated with disabling symptoms
- paroxysmal atrial fibrillation/flutter (PAF) associated with disabling symptoms
Flecainide is also indicated for the prevention of
- documented ventricular arrhythmias, such as sustained ventricular tachycardia (sustained VT), that in the judgment of the physician, are lifethreatening. Launch Date2001 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
355 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/3094570 |
200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered: |
FLECAINIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
1710 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/3094570 |
2 mg/kg single, intravenous dose: 2 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered: |
FLECAINIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
5979 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/3094570 |
200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered: |
FLECAINIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
6238 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/3094570 |
2 mg/kg single, intravenous dose: 2 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered: |
FLECAINIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
5.9 μg × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/1782978 |
200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered: |
FLECAINIDE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
11.5 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/1782978 |
200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered: |
FLECAINIDE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
60% EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/6364769 |
FLECAINIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
1200 mg single, oral Overdose Dose: 1200 mg Route: oral Route: single Dose: 1200 mg Sources: Page: p.487 |
healthy, 18 n = 1 Health Status: healthy Age Group: 18 Sex: F Population Size: 1 Sources: Page: p.487 |
Disc. AE: Unconsciousness, Cyanosis... AEs leading to discontinuation/dose reduction: Unconsciousness Sources: Page: p.487Cyanosis Bradycardia Arrhythmia |
3800 mg single, oral Overdose Dose: 3800 mg Route: oral Route: single Dose: 3800 mg Co-administed with:: diazepam, p.o(50 mg) Sources: loperamide, p.o(20 mg) |
healthy, 28 n = 1 Health Status: healthy Age Group: 28 Sex: F Population Size: 1 Sources: |
Disc. AE: Polymorphic ventricular tachycardia... AEs leading to discontinuation/dose reduction: Polymorphic ventricular tachycardia Sources: |
10 g single, oral Overdose Dose: 10 g Route: oral Route: single Dose: 10 g Sources: Page: p.423 |
healthy, 36 n = 1 Health Status: healthy Age Group: 36 Sex: M Population Size: 1 Sources: Page: p.423 |
Disc. AE: Ventricular tachycardia, Hypotension... AEs leading to discontinuation/dose reduction: Ventricular tachycardia Sources: Page: p.423Hypotension Cardiopulmonary arrest |
1 g single, oral Overdose Dose: 1 g Route: oral Route: single Dose: 1 g Co-administed with:: lamotrigine, p.o Sources: Page: p.1quetiapine, p.o |
unhealthy, 62 n = 1 Health Status: unhealthy Condition: Atrial fibrillation Age Group: 62 Sex: M Population Size: 1 Sources: Page: p.1 |
Disc. AE: Brugada syndrome, Mental status changes... AEs leading to discontinuation/dose reduction: Brugada syndrome Sources: Page: p.1Mental status changes Fatigue |
200 mg 2 times / day multiple, oral Recommended Dose: 200 mg, 2 times / day Route: oral Route: multiple Dose: 200 mg, 2 times / day Sources: |
unhealthy Health Status: unhealthy Condition: Paroxysmal supraventricular tachycardias|paroxysmal atrial fibrillation/flutter|Sustained ventricular tachycardia Sources: |
Disc. AE: Ventricular tachycardia, Cardiac arrest... AEs leading to discontinuation/dose reduction: Ventricular tachycardia Sources: Cardiac arrest |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Arrhythmia | Disc. AE | 1200 mg single, oral Overdose Dose: 1200 mg Route: oral Route: single Dose: 1200 mg Sources: Page: p.487 |
healthy, 18 n = 1 Health Status: healthy Age Group: 18 Sex: F Population Size: 1 Sources: Page: p.487 |
Bradycardia | Disc. AE | 1200 mg single, oral Overdose Dose: 1200 mg Route: oral Route: single Dose: 1200 mg Sources: Page: p.487 |
healthy, 18 n = 1 Health Status: healthy Age Group: 18 Sex: F Population Size: 1 Sources: Page: p.487 |
Cyanosis | Disc. AE | 1200 mg single, oral Overdose Dose: 1200 mg Route: oral Route: single Dose: 1200 mg Sources: Page: p.487 |
healthy, 18 n = 1 Health Status: healthy Age Group: 18 Sex: F Population Size: 1 Sources: Page: p.487 |
Unconsciousness | Disc. AE | 1200 mg single, oral Overdose Dose: 1200 mg Route: oral Route: single Dose: 1200 mg Sources: Page: p.487 |
healthy, 18 n = 1 Health Status: healthy Age Group: 18 Sex: F Population Size: 1 Sources: Page: p.487 |
Polymorphic ventricular tachycardia | Disc. AE | 3800 mg single, oral Overdose Dose: 3800 mg Route: oral Route: single Dose: 3800 mg Co-administed with:: diazepam, p.o(50 mg) Sources: loperamide, p.o(20 mg) |
healthy, 28 n = 1 Health Status: healthy Age Group: 28 Sex: F Population Size: 1 Sources: |
Cardiopulmonary arrest | Disc. AE | 10 g single, oral Overdose Dose: 10 g Route: oral Route: single Dose: 10 g Sources: Page: p.423 |
healthy, 36 n = 1 Health Status: healthy Age Group: 36 Sex: M Population Size: 1 Sources: Page: p.423 |
Hypotension | Disc. AE | 10 g single, oral Overdose Dose: 10 g Route: oral Route: single Dose: 10 g Sources: Page: p.423 |
healthy, 36 n = 1 Health Status: healthy Age Group: 36 Sex: M Population Size: 1 Sources: Page: p.423 |
Ventricular tachycardia | Disc. AE | 10 g single, oral Overdose Dose: 10 g Route: oral Route: single Dose: 10 g Sources: Page: p.423 |
healthy, 36 n = 1 Health Status: healthy Age Group: 36 Sex: M Population Size: 1 Sources: Page: p.423 |
Brugada syndrome | Disc. AE | 1 g single, oral Overdose Dose: 1 g Route: oral Route: single Dose: 1 g Co-administed with:: lamotrigine, p.o Sources: Page: p.1quetiapine, p.o |
unhealthy, 62 n = 1 Health Status: unhealthy Condition: Atrial fibrillation Age Group: 62 Sex: M Population Size: 1 Sources: Page: p.1 |
Fatigue | Disc. AE | 1 g single, oral Overdose Dose: 1 g Route: oral Route: single Dose: 1 g Co-administed with:: lamotrigine, p.o Sources: Page: p.1quetiapine, p.o |
unhealthy, 62 n = 1 Health Status: unhealthy Condition: Atrial fibrillation Age Group: 62 Sex: M Population Size: 1 Sources: Page: p.1 |
Mental status changes | Disc. AE | 1 g single, oral Overdose Dose: 1 g Route: oral Route: single Dose: 1 g Co-administed with:: lamotrigine, p.o Sources: Page: p.1quetiapine, p.o |
unhealthy, 62 n = 1 Health Status: unhealthy Condition: Atrial fibrillation Age Group: 62 Sex: M Population Size: 1 Sources: Page: p.1 |
Cardiac arrest | Disc. AE | 200 mg 2 times / day multiple, oral Recommended Dose: 200 mg, 2 times / day Route: oral Route: multiple Dose: 200 mg, 2 times / day Sources: |
unhealthy Health Status: unhealthy Condition: Paroxysmal supraventricular tachycardias|paroxysmal atrial fibrillation/flutter|Sustained ventricular tachycardia Sources: |
Ventricular tachycardia | Disc. AE | 200 mg 2 times / day multiple, oral Recommended Dose: 200 mg, 2 times / day Route: oral Route: multiple Dose: 200 mg, 2 times / day Sources: |
unhealthy Health Status: unhealthy Condition: Paroxysmal supraventricular tachycardias|paroxysmal atrial fibrillation/flutter|Sustained ventricular tachycardia Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
yes [IC50 0.44 uM] | ||||
yes [IC50 0.49 uM] | ||||
yes [IC50 191 uM] |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
yes | ||||
yes | yes (co-administration study) Comment: During the period in which the CYP2D6 inhibitor paroxetine was administered, the flecainide AUC in extensive and intermediate metabolizers was increased to 128.5% of basal values (90% CI, 122.2%– 135.2%) and 116.6% of basal values (90% CI, 107.3%–126.8%). However, poor metabolizers exhibited no alterations in AUC after administration of paroxetine (pharmacogenomic studies were also performed) |
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
PubMed
Title | Date | PubMed |
---|---|---|
Comparative haemodynamic effects of intravenous lignocaine, disopyramide and flecainide in uncomplicated acute myocardial infarction. | 1986 Dec |
|
Dysarthria and visual hallucinations due to flecainide toxicity. | 1986 Jan |
|
Flecainide acetate in the treatment of tachycardias associated with Mahaim fibres. | 1987 Aug |
|
[Drug-induced intrahepatic cholestasis caused by flecainide acetate and enalapril]. | 1987 Mar |
|
Flecainide-induced sustained ventricular tachycardia successfully treated with lidocaine. | 1987 Sep |
|
Rapid suppression of flecainide-induced incessant ventricular tachycardia with high-dose intravenous amiodarone. | 1988 Apr |
|
[Central nervous system side effects due to anti-arrhythmia therapy. Psychotic depression due to flecainide]. | 1988 Mar 11 |
|
Prevention of symptomatic recurrences of paroxysmal atrial fibrillation in patients initially tolerating antiarrhythmic therapy. A multicenter, double-blind, crossover study of flecainide and placebo with transtelephonic monitoring. Flecainide Supraventricular Tachycardia Study Group. | 1989 Dec |
|
Cardioprotective effects of various class I antiarrhythmic drugs in canine hearts. | 1989 Jul |
|
[Bidirectional tachycardia during therapy with lorajmine]. | 1989 Oct |
|
Generalized seizures as the presentation of flecainide toxicity. | 1989 Oct |
|
Acute urinary retention associated with flecainide. | 1990 Jan-Feb |
|
Serious interactions of sotalol with amiodarone and flecainide. | 1990 Mar 5 |
|
Amiodarone toxicity: myopathy and neuropathy. | 1990 May |
|
[Effects of oral flecainide treatment of refractory tachyarrhythmias]. | 1990 May |
|
Combined application of class I antiarrhythmic drugs causes "additive", "reductive", or "synergistic" sodium channel block in cardiac muscles. | 1990 Nov |
|
Relative efficacy and safety of intravenous drugs for termination of sustained ventricular tachycardia. | 1990 Sep 15 |
|
Proarrhythmia, cardiac arrest and death in young patients receiving encainide and flecainide. The Pediatric Electrophysiology Group. | 1991 Aug |
|
Flecainide acetate treatment of paroxysmal supraventricular tachycardia and paroxysmal atrial fibrillation: dose-response studies. The Flecainide Supraventricular Tachycardia Study Group. | 1991 Feb |
|
Safety and efficacy of oral flecainide therapy in patients with atrioventricular re-entrant tachycardia. | 1991 Feb 1 |
|
Flecainide acetate prevents recurrence of symptomatic paroxysmal supraventricular tachycardia. The Flecainide Supraventricular Tachycardia Study Group. | 1991 Jan |
|
Reversion of recent-onset atrial fibrillation to sinus rhythm by intravenous flecainide. | 1991 Jan 15 |
|
Mortality and morbidity in patients receiving encainide, flecainide, or placebo. The Cardiac Arrhythmia Suppression Trial. | 1991 Mar 21 |
|
Flecainide in quinidine-resistant atrial fibrillation. | 1992 Aug 20 |
|
Effects of advancing age on the efficacy and side effects of antiarrhythmic drugs in post-myocardial infarction patients with ventricular arrhythmias. The CAST Investigators. | 1992 Jul |
|
Use of ibutilide in cardioversion of patients with atrial fibrillation or atrial flutter treated with class IC agents. | 2004 Aug 18 |
|
Electrocardiographical case. Asymptomatic patient with ST-segment elevation. | 2004 Nov |
|
A toxicogenomic approach to drug-induced phospholipidosis: analysis of its induction mechanism and establishment of a novel in vitro screening system. | 2005 Feb |
|
Long-term results of hybrid therapy in patients with atrial fibrillation who develop atrial flutter during flecainide infusion. | 2005 Jan |
|
Assessment of serum flecainide trough levels in patients with tachyarrhythmia. | 2005 Jan |
|
Flecainide-induced neuropathy. | 2005 Sep |
|
Long-term protection of central axons with phenytoin in monophasic and chronic-relapsing EAE. | 2006 Dec |
|
Management of atrial fibrillation. | 2007 |
|
Further evidence of inherited long QT syndrome gene mutations in antiarrhythmic drug-associated torsades de pointes. | 2007 May |
|
Flecainide cardiotoxicity precipitated by electrolyte imbalance. Caution with thiazide diuretics. | 2007 May |
|
The Relationship Between HIV Infection and Cardiovascular Disease. | 2008 Aug |
|
Drug therapy considerations in arrhythmias in children. | 2008 Aug 1 |
|
Ventricular dysfunction: tachycardia induced cardiomyopathy. | 2008 May 1 |
|
ECGs in the ED. | 2008 Nov |
|
Role of cytochrome P450 in drug interactions. | 2008 Oct 18 |
|
A preliminary assessment of the effects of ATI-2042 in subjects with paroxysmal atrial fibrillation using implanted pacemaker methodology. | 2009 Apr |
|
Is flecainide dangerous in long QT-3 patients? | 2009 Jan |
|
Delirium in a patient with toxic flecainide plasma concentrations: the role of a pharmacokinetic drug interaction with paroxetine. | 2009 Jul |
|
Effects of antiarrhythmic drugs on the hyperpolarization-activated cyclic nucleotide-gated channel current. | 2009 Jun |
|
A case of flecainide-induced hyponatremia. | 2009 Oct |
|
Tpeak-Tend interval and Tpeak-Tend/QT ratio as markers of ventricular tachycardia inducibility in subjects with Brugada ECG phenotype. | 2010 Feb |
|
Tachycardia due to atrial flutter with rapid 1:1 conduction following treatment of atrial fibrillation with flecainide. | 2010 Mar 10 |
|
Selective regulation of cardiac organic cation transporter novel type 2 (OCTN2) in dilated cardiomyopathy. | 2011 Jun |
|
Comparison of a genomic and a multiplex cell imaging approach for the detection of phospholipidosis. | 2011 Oct |
|
Estimating the risk of drug-induced proarrhythmia using human induced pluripotent stem cell-derived cardiomyocytes. | 2011 Sep |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.drugs.com/dosage/flecainide.html
Usual Adult Dose for Ventricular Tachycardia
Initial dose: 100 mg orally every 12 hours.
Maintenance dose: May be increased in increments of 50 mg bid every 4 days until efficacy is achieved. Most patients with SUSTAINED VT do not require more than 150 mg every 12 hours (300 mg/day), and the maximum dose recommended is 400 mg/day.
Usual Adult Dose for Atrial Fibrillation
Initial dose: 50 mg orally every 12 hours.
Maintenance dose: May be increased in increments of 50 mg bid every 4 days until efficacy is achieved.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/25219538
Flecainide produced a dose-dependent prolongation of the cardiac action potential at 1 and 3uM in human pluripotent stem cell-derived cardiomyocytes.
Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 17:45:40 GMT 2023
by
admin
on
Sat Dec 16 17:45:40 GMT 2023
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Record UNII |
K94FTS1806
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Record Status |
Validated (UNII)
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Record Version |
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NDF-RT |
N0000175426
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WHO-VATC |
QC01BC04
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NBK548023
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FDA ORPHAN DRUG |
536716
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C01BC04
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NCI_THESAURUS |
C47793
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NCI_THESAURUS |
C93038
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m5400
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3356
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Flecainide
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100000080972
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CHEMBL652
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2560
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4096
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SALT/SOLVATE -> PARENT | |||
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TARGET -> INHIBITOR |
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METABOLITE -> PARENT | |||
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METABOLITE -> PARENT |
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ACTIVE MOIETY |