Details
Stereochemistry | RACEMIC |
Molecular Formula | C11H17NO.ClH |
Molecular Weight | 215.72 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.CC(N)COC1=C(C)C=CC=C1C
InChI
InChIKey=NFEIBWMZVIVJLQ-UHFFFAOYSA-N
InChI=1S/C11H17NO.ClH/c1-8-5-4-6-9(2)11(8)13-7-10(3)12;/h4-6,10H,7,12H2,1-3H3;1H
Molecular Formula | C11H17NO |
Molecular Weight | 179.2588 |
Charge | 0 |
Count |
|
Stereochemistry | RACEMIC |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Optical Activity | ( + / - ) |
Molecular Formula | ClH |
Molecular Weight | 36.461 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Mexiletine is a non-selective voltage-gated sodium channel blocker which belongs to the Class IB anti-arrhythmic group of medicines. It is used to treat heart arrhythmias. Mexiletine is also used to treat refractory pain and muscle stiffness resulting in myotonic dystrophy or myotonia congenita. Mexiletine was approved for commercial use in 1985 under the brand name Mexitil, but most marketing efforts have since been discontinued. There has been a continued effort to identify other therapeutic use cases and a number of clinical trials have been conducted including ALS and chronic pain from amputation.
CNS Activity
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: Q14524|||E9PFW7 Gene ID: 6331.0 Gene Symbol: SCN5A Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/16168489 |
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Target ID: Q15858|||Q8WWN4 Gene ID: 6335.0 Gene Symbol: SCN9A Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/26068619 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | MEXITIL Approved UseMexiletine hydrochloride capsules are indicated for the treatment of documented ventricular arrhythmias, such as sustained ventricular tachycardia, that, in the judgment of the physician, are life-threatening. Because of the proarrhythmic effects of mexiletine, its use with lesser arrhythmias is generally not recommended. Treatment of patients with asymptomatic ventricular premature contractions should be avoided. Initiation of mexiletine treatment, as with other antiarrhythmic agents used to treat life-threatening arrhythmias, should be carried out in the hospital. Antiarrhythmic drugs have not been shown to enhance survival in patients with ventricular arrhythmias. Launch Date5.04748802E11 |
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Primary | MEXITIL Approved UseMexiletine hydrochloride capsules are indicated for the treatment of documented ventricular arrhythmias, such as sustained ventricular tachycardia, that, in the judgment of the physician, are life-threatening. Because of the proarrhythmic effects of mexiletine, its use with lesser arrhythmias is generally not recommended. Treatment of patients with asymptomatic ventricular premature contractions should be avoided. Initiation of mexiletine treatment, as with other antiarrhythmic agents used to treat life-threatening arrhythmias, should be carried out in the hospital. Antiarrhythmic drugs have not been shown to enhance survival in patients with ventricular arrhythmias. Launch Date5.04748802E11 |
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Primary | Unknown Approved UseUnknown |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
0.21 μg/mL |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: |
MEXILETINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
1.2 μg/mL |
200 mg 3 times / day multiple, oral dose: 200 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
MEXILETINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
0.59 μg/mL |
100 mg 3 times / day multiple, oral dose: 100 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
MEXILETINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
0.35 μg/mL |
150 mg single, oral dose: 150 mg route of administration: Oral experiment type: SINGLE co-administered: |
MEXILETINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
0.46 μg/mL |
300 mg single, oral dose: 300 mg route of administration: Oral experiment type: SINGLE co-administered: |
MEXILETINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
0.45 μg/mL |
200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered: |
MEXILETINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
0.81 μg/mL |
400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered: |
MEXILETINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
2.96 μg × h/mL |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: |
MEXILETINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
22 μg × h/mL |
200 mg 3 times / day multiple, oral dose: 200 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
MEXILETINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
3.7 μg × h/mL |
100 mg 3 times / day multiple, oral dose: 100 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
MEXILETINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
5.8 μg × h/mL |
150 mg single, oral dose: 150 mg route of administration: Oral experiment type: SINGLE co-administered: |
MEXILETINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
6.7 μg × h/mL |
300 mg single, oral dose: 300 mg route of administration: Oral experiment type: SINGLE co-administered: |
MEXILETINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
7.76 μg × h/mL |
200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered: |
MEXILETINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
8.3 μg × h/mL |
400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered: |
MEXILETINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
9.4 h |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: |
MEXILETINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
9.9 h |
200 mg 3 times / day multiple, oral dose: 200 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
MEXILETINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
14.1 h |
100 mg 3 times / day multiple, oral dose: 100 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
MEXILETINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
10.8 h |
150 mg single, oral dose: 150 mg route of administration: Oral experiment type: SINGLE co-administered: |
MEXILETINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
10 h |
300 mg single, oral dose: 300 mg route of administration: Oral experiment type: SINGLE co-administered: |
MEXILETINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
11.1 h |
200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered: |
MEXILETINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
7 h |
400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered: |
MEXILETINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
40% |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: |
MEXILETINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
500 mg single, intramuscular Highest studied dose Dose: 500 mg Route: intramuscular Route: single Dose: 500 mg Sources: Page: p.24, 25 |
unhealthy, 55-78 n = 9 Health Status: unhealthy Condition: Myocardial infarction Age Group: 55-78 Sex: M+F Population Size: 9 Sources: Page: p.24, 25 |
|
400 mg 3 times / day multiple, oral MTD Dose: 400 mg, 3 times / day Route: oral Route: multiple Dose: 400 mg, 3 times / day Sources: Page: p.132 |
unhealthy, 55.5 n = 16 Health Status: unhealthy Condition: Ventricular arrhythmias Age Group: 55.5 Sex: M+F Population Size: 16 Sources: Page: p.132 |
|
200 mg 3 times / day multiple, oral Recommended Dose: 200 mg, 3 times / day Route: oral Route: multiple Dose: 200 mg, 3 times / day Sources: Page: p.105, 106, 112 |
unhealthy n = 25 Health Status: unhealthy Condition: Myotonic disorders Population Size: 25 Sources: Page: p.105, 106, 112 |
Disc. AE: Tachycardia... AEs leading to discontinuation/dose reduction: Tachycardia (severe, 4%) Sources: Page: p.105, 106, 112 |
200 mg 3 times / day multiple, oral (max) Recommended Dose: 200 mg, 3 times / day Route: oral Route: multiple Dose: 200 mg, 3 times / day Sources: Page: p.109 |
unhealthy n = 39 Health Status: unhealthy Condition: Myotonic disorders Population Size: 39 Sources: Page: p.109 |
Disc. AE: Diarrhea... AEs leading to discontinuation/dose reduction: Diarrhea (2.6%) Sources: Page: p.109 |
200 mg 3 times / day multiple, oral Recommended Dose: 200 mg, 3 times / day Route: oral Route: multiple Dose: 200 mg, 3 times / day Sources: Page: p.109 |
unhealthy n = 58 Health Status: unhealthy Condition: Myotonic disorders Population Size: 58 Sources: Page: p.109 |
Disc. AE: Migraine, Gastrointestinal discomfort... AEs leading to discontinuation/dose reduction: Migraine (1.7%) Sources: Page: p.109Gastrointestinal discomfort (1.7%) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Tachycardia | severe, 4% Disc. AE |
200 mg 3 times / day multiple, oral Recommended Dose: 200 mg, 3 times / day Route: oral Route: multiple Dose: 200 mg, 3 times / day Sources: Page: p.105, 106, 112 |
unhealthy n = 25 Health Status: unhealthy Condition: Myotonic disorders Population Size: 25 Sources: Page: p.105, 106, 112 |
Diarrhea | 2.6% Disc. AE |
200 mg 3 times / day multiple, oral (max) Recommended Dose: 200 mg, 3 times / day Route: oral Route: multiple Dose: 200 mg, 3 times / day Sources: Page: p.109 |
unhealthy n = 39 Health Status: unhealthy Condition: Myotonic disorders Population Size: 39 Sources: Page: p.109 |
Gastrointestinal discomfort | 1.7% Disc. AE |
200 mg 3 times / day multiple, oral Recommended Dose: 200 mg, 3 times / day Route: oral Route: multiple Dose: 200 mg, 3 times / day Sources: Page: p.109 |
unhealthy n = 58 Health Status: unhealthy Condition: Myotonic disorders Population Size: 58 Sources: Page: p.109 |
Migraine | 1.7% Disc. AE |
200 mg 3 times / day multiple, oral Recommended Dose: 200 mg, 3 times / day Route: oral Route: multiple Dose: 200 mg, 3 times / day Sources: Page: p.109 |
unhealthy n = 58 Health Status: unhealthy Condition: Myotonic disorders Population Size: 58 Sources: Page: p.109 |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: 18, 44 |
likely | |||
Page: 1, 2 |
major | |||
Page: 1, 2 |
minor | yes (co-administration study) Comment: coadminitration with fluvoxamine decreased mexiletine clearance by 38% Page: 1, 2 |
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
PubMed
Title | Date | PubMed |
---|---|---|
Facilitation of ventricular tachyarrhythmia induction by isoproterenol. | 1984 Oct 1 |
|
Inhibition of sympathetic nervous system by mexiletine, an antiarrhythmic agent, and its antagonism against ouabain. | 1985 |
|
Mexiletine: long-term follow-up of a patient with prolonged QT interval and quinidine-induced torsades de pointes. | 1985 Feb |
|
[2 cases of lidocaine-resistant ventricular tachycardia treated with i.v. mexiletine during complicated acute myocardial infarct]. | 1987 Nov 30 |
|
General pharmacological studies on N-(2,6-dimethylphenyl)-8-pyrrolizidineacetamide hydrochloride hemihydrate. 1st communication: effect on the central nervous system. | 1988 Oct |
|
Cardioprotective effects of various class I antiarrhythmic drugs in canine hearts. | 1989 Jul |
|
Long-term effect of mexiletine on left ventricular function and relation to suppression of ventricular arrhythmia. | 1990 Nov 15 |
|
Mexiletine's antifibrillatory actions are limited by the occurrence of convulsions in conscious animals. | 1992 Jan 21 |
|
Neurotoxicity of lidocaine combined with mexiletine. | 1993 Dec |
|
Usefulness of oral quinidine-mexiletine combination therapy for sustained ventricular tachyarrhythmias as assessed by programmed electrical stimulation when quinidine monotherapy has failed. | 1994 Apr |
|
Mexiletine-induced severe skin eruption, fever, eosinophilia, atypical lymphocytosis, and liver dysfunction. | 1997 Oct |
|
Effects of mexiletine on algogenic mediator-induced nociceptive responses in mice. | 1999 Jul-Aug |
|
Effects of mexiletine on the canine cardiovascular system complicating cisapride overdose: potential utility of mexiletine for the treatment of drug-induced long QT syndrome. | 2000 Aug |
|
Mexiletine block of wild-type and inactivation-deficient human skeletal muscle hNav1.4 Na+ channels. | 2004 Feb 1 |
|
Analysis of human Nav1.8 expressed in SH-SY5Y neuroblastoma cells. | 2005 Dec 28 |
|
Effect of mexiletine on vincristine-induced painful neuropathy in mice. | 2006 Apr 24 |
|
Digoxin and mexiletine sensitivity in a Collie with the MDR1 mutation. | 2006 Mar-Apr |
|
Experimental studies of potential analgesics for the treatment of chemotherapy-evoked painful peripheral neuropathies. | 2008 Jul-Aug |
|
Pharmacological characterization and gene expression profiling of an L5/L6 spinal nerve ligation model for neuropathic pain in mice. | 2008 May 2 |
|
Effects of antiarrhythmic drugs on the hyperpolarization-activated cyclic nucleotide-gated channel current. | 2009 Jun |
|
Synergistic drug-cytokine induction of hepatocellular death as an in vitro approach for the study of inflammation-associated idiosyncratic drug hepatotoxicity. | 2009 Jun 15 |
Sample Use Guides
Mexiletine dosage must be individualized on the basis of response and tolerance. Administration with food is recommended. Initiate Mexiletine hydrochloride therapy with 200 mg every 8 hours when rapid control of arrhythmia is not essential. A minimum of two to three days between dose adjustments is recommended. The dose may be adjusted up or down in 50 or 100 mg increments. Most patients achieve satisfactory control with between 200 - 300 mg every 8 hours.The total daily dose should not exceed 400 mg.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/26068619
HEK293 cells stably expressing human homolog of human Nav1.5 and human Nav1.7 channels were maintained under standard tissue culture conditions (5% CO2; 37°C) in Dulbecco’s modified Eagle’s medium and F-12 medium mixture at 1:1 supplemented with 10% fetal bovine serum under selection of antibiotic G418 with a concentration of 500 μg/mL. Cells were passaged every three days with 0.25% Trypsin-EDTA. Whole-cell recordings were performed 18–24 h after plating at room temperature. Whole-cell patch-clamp recordings were conducted at room temperature (22–25°C) using an EPC-10 USB amplifier. The pipette solution contained (in mM): 140 CsF, 10 NaCl, 1 EGTA, and 10 HEPES; pH 7.3 with CsOH. The bath solution for recording contained (in mM): 140 NaCl, 3 KCl, 10 HEPES, 1 MgCl2, 1 CaCl2; pH 7.3 with NaOH. Mexiletine was diluted in bath solution to the desired concentration. Bath application of 0.3 mM mexiletine resulted in a reduction of Nav1.5 or Nav1.7 currents, while V1/2 values were not significantly shifted for even up to 1.0 mM.
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 17:32:22 UTC 2023
by
admin
on
Fri Dec 15 17:32:22 UTC 2023
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Record UNII |
606D60IS38
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Record Status |
Validated (UNII)
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Record Version |
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Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C47793
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EU-Orphan Drug |
EU/3/14/1353
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NCI_THESAURUS |
C93038
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5370-01-4
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X-90
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1443250
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21467
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226-362-1
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m7518
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606D60IS38
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6917
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100000092433
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SUB03281MIG
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142138
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25670-67-1
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758639
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C652
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CHEMBL558
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IMPURITY -> PARENT |
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IMPURITY -> PARENT |
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IMPURITY -> PARENT |
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