Details
Stereochemistry | RACEMIC |
Molecular Formula | C32H41NO2 |
Molecular Weight | 471.6734 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CC(C)(C)C1=CC=C(C=C1)C(O)CCCN2CCC(CC2)C(O)(C3=CC=CC=C3)C4=CC=CC=C4
InChI
InChIKey=GUGOEEXESWIERI-UHFFFAOYSA-N
InChI=1S/C32H41NO2/c1-31(2,3)26-18-16-25(17-19-26)30(34)15-10-22-33-23-20-29(21-24-33)32(35,27-11-6-4-7-12-27)28-13-8-5-9-14-28/h4-9,11-14,16-19,29-30,34-35H,10,15,20-24H2,1-3H3
Molecular Formula | C32H41NO2 |
Molecular Weight | 471.6734 |
Charge | 0 |
Count |
|
Stereochemistry | RACEMIC |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Optical Activity | ( + / - ) |
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL231 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19660947 |
40.0 nM [Ki] |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1.544 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6113858/ |
60 mg single, oral dose: 60 mg route of administration: Oral experiment type: SINGLE co-administered: |
TERFENADINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
4.519 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6113858/ |
180 mg single, oral dose: 180 mg route of administration: Oral experiment type: SINGLE co-administered: |
TERFENADINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
458.1 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1576325/ |
120 mg single, oral dose: 120 mg route of administration: Oral experiment type: SINGLE co-administered: |
TERFENADINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: HIGH-FAT |
|
406.9 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1576325/ |
120 mg single, oral dose: 120 mg route of administration: Oral experiment type: SINGLE co-administered: |
TERFENADINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
11.864 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6113858/ |
60 mg single, oral dose: 60 mg route of administration: Oral experiment type: SINGLE co-administered: |
TERFENADINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
44.341 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6113858/ |
180 mg single, oral dose: 180 mg route of administration: Oral experiment type: SINGLE co-administered: |
TERFENADINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
2712.1 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1576325/ |
120 mg single, oral dose: 120 mg route of administration: Oral experiment type: SINGLE co-administered: |
TERFENADINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: HIGH-FAT |
|
2720.1 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1576325/ |
120 mg single, oral dose: 120 mg route of administration: Oral experiment type: SINGLE co-administered: |
TERFENADINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
11.6 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1576325/ |
120 mg single, oral dose: 120 mg route of administration: Oral experiment type: SINGLE co-administered: |
TERFENADINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: HIGH-FAT |
|
12.6 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1576325/ |
120 mg single, oral dose: 120 mg route of administration: Oral experiment type: SINGLE co-administered: |
TERFENADINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
Doses
Dose | Population | Adverse events |
---|---|---|
180 mg 2 times / day multiple, oral Highest studied dose Dose: 180 mg, 2 times / day Route: oral Route: multiple Dose: 180 mg, 2 times / day Sources: Page: p.203 |
healthy, 18-40 n = 24 Health Status: healthy Age Group: 18-40 Sex: M Population Size: 24 Sources: Page: p.203 |
Other AEs: Electrocardiogram QTc interval prolonged... Other AEs: Electrocardiogram QTc interval prolonged (12.5%) Sources: Page: p.203 |
60 mg 2 times / day multiple, oral Recommended Dose: 60 mg, 2 times / day Route: oral Route: multiple Dose: 60 mg, 2 times / day Sources: Page: p.69 |
unhealthy, 18-45 n = 24 Health Status: unhealthy Condition: Seasonal allergic rhinitis Age Group: 18-45 Sex: M Population Size: 24 Sources: Page: p.69 |
Disc. AE: Headache... Other AEs: Somnolence... AEs leading to discontinuation/dose reduction: Headache (grade 2-3, 8.3%) Other AEs:Somnolence (grade 1, 4.15%) Sources: Page: p.69 |
120 mg 1 times / day multiple, oral Recommended Dose: 120 mg, 1 times / day Route: oral Route: multiple Dose: 120 mg, 1 times / day Sources: Page: p.462 |
unhealthy, 19-66 n = 41 Health Status: unhealthy Condition: Adverse reactions to specific immunotherapy with Hymenoptera venom Age Group: 19-66 Sex: M+F Population Size: 41 Sources: Page: p.462 |
Disc. AE: Nausea, Headache... AEs leading to discontinuation/dose reduction: Nausea (2.4%) Sources: Page: p.462Headache (2.4%) |
60 mg single, oral Recommended Dose: 60 mg Route: oral Route: single Dose: 60 mg Sources: Page: p.406 |
healthy, 23-40 n = 12 Health Status: healthy Age Group: 23-40 Sex: M Population Size: 12 Sources: Page: p.406 |
|
240 mg single, oral Highest studied dose Dose: 240 mg Route: oral Route: single Dose: 240 mg Sources: Page: p.610 |
healthy, 23-47 n = 12 Health Status: healthy Age Group: 23-47 Sex: F Population Size: 12 Sources: Page: p.610 |
Other AEs: Driving ability disturbed... |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Electrocardiogram QTc interval prolonged | 12.5% | 180 mg 2 times / day multiple, oral Highest studied dose Dose: 180 mg, 2 times / day Route: oral Route: multiple Dose: 180 mg, 2 times / day Sources: Page: p.203 |
healthy, 18-40 n = 24 Health Status: healthy Age Group: 18-40 Sex: M Population Size: 24 Sources: Page: p.203 |
Somnolence | grade 1, 4.15% | 60 mg 2 times / day multiple, oral Recommended Dose: 60 mg, 2 times / day Route: oral Route: multiple Dose: 60 mg, 2 times / day Sources: Page: p.69 |
unhealthy, 18-45 n = 24 Health Status: unhealthy Condition: Seasonal allergic rhinitis Age Group: 18-45 Sex: M Population Size: 24 Sources: Page: p.69 |
Headache | grade 2-3, 8.3% Disc. AE |
60 mg 2 times / day multiple, oral Recommended Dose: 60 mg, 2 times / day Route: oral Route: multiple Dose: 60 mg, 2 times / day Sources: Page: p.69 |
unhealthy, 18-45 n = 24 Health Status: unhealthy Condition: Seasonal allergic rhinitis Age Group: 18-45 Sex: M Population Size: 24 Sources: Page: p.69 |
Headache | 2.4% Disc. AE |
120 mg 1 times / day multiple, oral Recommended Dose: 120 mg, 1 times / day Route: oral Route: multiple Dose: 120 mg, 1 times / day Sources: Page: p.462 |
unhealthy, 19-66 n = 41 Health Status: unhealthy Condition: Adverse reactions to specific immunotherapy with Hymenoptera venom Age Group: 19-66 Sex: M+F Population Size: 41 Sources: Page: p.462 |
Nausea | 2.4% Disc. AE |
120 mg 1 times / day multiple, oral Recommended Dose: 120 mg, 1 times / day Route: oral Route: multiple Dose: 120 mg, 1 times / day Sources: Page: p.462 |
unhealthy, 19-66 n = 41 Health Status: unhealthy Condition: Adverse reactions to specific immunotherapy with Hymenoptera venom Age Group: 19-66 Sex: M+F Population Size: 41 Sources: Page: p.462 |
Driving ability disturbed | 240 mg single, oral Highest studied dose Dose: 240 mg Route: oral Route: single Dose: 240 mg Sources: Page: p.610 |
healthy, 23-47 n = 12 Health Status: healthy Age Group: 23-47 Sex: F Population Size: 12 Sources: Page: p.610 |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://pubmed.ncbi.nlm.nih.gov/15133245/ Page: 6.0 |
yes [IC50 23 uM] | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/21612343/ Page: 17.0 |
yes [IC50 41 uM] | |||
Page: 2.0 |
yes [IC50 <10 uM] | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/16495056/ Page: 1.0 |
yes [Ki 0.16 uM] | |||
yes [Ki 3.6 uM] | ||||
yes [Ki 5 uM] |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
yes | ||||
Sources: https://pubmed.ncbi.nlm.nih.gov/17180728/ Page: 8.0 |
yes | |||
Page: 1.0 |
yes | likely (co-administration study) Comment: From abstract: a drug interaction between terfenadine and ketoconazole resulted in the elevated terfenadine levels in plasma and in the cardiotoxicity previously seen only in cases of terfenadine overdose. Page: 1.0 |
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
PubMed
Title | Date | PubMed |
---|---|---|
Impact of rhinitis on airway inflammation: biological and therapeutic implications. | 2001 |
|
[The effect of second generation histamine antagonists on the heart]. | 2001 |
|
Drug-induced cholestasis. | 2001 Apr |
|
Problems of heart rate correction in assessment of drug-induced QT interval prolongation. | 2001 Apr |
|
Identification of functionally variant MDR1 alleles among European Americans and African Americans. | 2001 Aug |
|
Effects of supratherapeutic doses of ebastine and terfenadine on the QT interval. | 2001 Aug |
|
Ugly wait at the counter. Insurer pushes to make allergy drugs nonprescription. | 2001 Aug 6 |
|
Second generation antihistamines in the treatment of seasonal allergic rhinitis due to Parietaria and cypress pollen. | 2001 Dec |
|
Evaluation of the safety of fexofenadine from experience gained in general practice use in England in 1997. | 2001 Jul |
|
Safety of fexofenadine in children treated for seasonal allergic rhinitis. | 2001 Jul |
|
Assessing the effect of intranasal steroids on growth. | 2001 Jul |
|
Antihistamines and the torsade de point in children with allergic rhinitis. | 2001 Jul-Aug |
|
Delusion of worm infestation associated with clarithromycin in a patient on peritoneal dialysis. | 2001 Jul-Aug |
|
Inhibition of human CYP1A2 activity in vitro by methylxanthines: potent competitive inhibition by 8-phenyltheophylline. | 2001 Mar |
|
Cooperativity of alpha-naphthoflavone in cytochrome P450 3A-dependent drug oxidation activities in hepatic and intestinal microsomes from mouse and human. | 2001 May |
|
A descriptive analysis of the use and cost of new-generation antihistamines in the treatment of allergic rhinitis: a retrospective database analysis. | 2001 May |
|
The canine Purkinje fiber: an in vitro model system for acquired long QT syndrome and drug-induced arrhythmogenesis. | 2001 May |
|
Fexofenadine reduces nasal congestion in perennial allergic rhinitis. | 2001 Nov |
|
Assay of terfenadine in pharmaceutical formulation and human plasma by adsorptive stripping voltammetry. | 2001 Nov |
|
Inhibition of depolarization-induced [3H]noradrenaline release from SH-SY5Y human neuroblastoma cells by some second-generation H(1) receptor antagonists through blockade of store-operated Ca(2+) channels (SOCs). | 2001 Nov 1 |
|
[Efficacy and safety of fexofenadine and cetirizine in the treatment of allergic rhinitis]. | 2001 Nov-Dec |
|
The costs of nonsedating antihistamine therapy for allergic rhinitis in managed care: an updated analysis. | 2001 Oct |
|
Effects of a new antiallergic drug, VUF-K-8788, on infiltration of lung parenchyma by eosinophils in guinea pigs and eosinophil-adhesion to human umbilical vein endothelial cells (HUVEC). | 2001 Oct |
|
Pharmacological characterization of the leukocyte kinetics after intranasal antigen challenge in a guinea pig model of allergic rhinitis. | 2001 Sep |
|
Potential cardiac toxicity of H1-antihistamines. | 2002 |
|
[Comparative antihistamine and anti-allergic effects of various antihistamine preparations]. | 2002 |
|
Grapefruit juice reduces the oral bioavailability of fexofenadine but not desloratadine. | 2002 |
|
Pharmacokinetic profile of zafirlukast. | 2002 |
|
[Chronic idiopathic urticaria: effectiveness of fexofenadine. A double-blind, placebo controlled study with 21 patients]. | 2002 Apr 10 |
|
The relationship of clinical QT prolongation to outcome in the conscious dog using a beat-to-beat QT-RR interval assessment. | 2002 Aug |
|
Are antihistamines useful in managing asthma? | 2002 Feb |
|
Cardiotoxicity of new antihistamines and cisapride. | 2002 Feb 28 |
|
An evaluation of the effects of high-dose fexofenadine on the central nervous system: a double-blind, placebo-controlled study in healthy volunteers. | 2002 Jan |
|
A comparison of once daily fexofenadine versus the combination of montelukast plus loratadine on domiciliary nasal peak flow and symptoms in seasonal allergic rhinitis. | 2002 Jan |
|
Fruit juices inhibit organic anion transporting polypeptide-mediated drug uptake to decrease the oral availability of fexofenadine. | 2002 Jan |
|
Induction of multidrug resistance-1 and cytochrome P450 mRNAs in human mononuclear cells by rifampin. | 2002 Jan |
|
Determination of fexofenadine in human plasma and urine by liquid chromatography-mass spectrometry. | 2002 Jan 25 |
|
Fexofenadine modulates T-cell function, preventing allergen-induced airway inflammation and hyperresponsiveness. | 2002 Jul |
|
Role of lung inflammatory mediators as a cause of exercise-induced arterial hypoxemia in young athletes. | 2002 Jul |
|
Chronic urticaria and angioedema. | 2002 Jul 18 |
|
Simultaneous determination of fexofenadine and its related compounds by HPLC. | 2002 Jul 20 |
|
Drug eruption and liver injury caused by terfenadine and oxatomide. | 2002 Jul-Aug |
|
Next generation antihistamines: therapeutic rationale, accomplishments and advances. | 2002 Jun |
|
Pharmacological rescue of human K(+) channel long-QT2 mutations: human ether-a-go-go-related gene rescue without block. | 2002 Jun 18 |
|
Intradermal cholinergic agonists induce itch-associated response via M3 muscarinic acetylcholine receptors in mice. | 2002 Mar |
|
Evaluation of cytokines in nasal secretions after nasal antigen challenge: lack of influence of antihistamines. | 2002 May |
|
MDR1 gene polymorphisms and disposition of the P-glycoprotein substrate fexofenadine. | 2002 May |
|
Three-dimensional quantitative structure-activity relationship for inhibition of human ether-a-go-go-related gene potassium channel. | 2002 May |
|
Delineation of the protective action of zinc sulfate on ulcerative colitis in rats. | 2002 May 17 |
|
Do standard doses of frequently prescribed drugs cause preventable adverse effects in women? | 2002 Spring |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/6129869
Terfenadine 20 mg 3 times a day
Route of Administration:
Oral
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 16:20:28 GMT 2023
by
admin
on
Fri Dec 15 16:20:28 GMT 2023
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Record UNII |
7BA5G9Y06Q
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Record Status |
Validated (UNII)
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Record Version |
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NCI_THESAURUS |
C29578
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WHO-ATC |
R06AX12
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WHO-VATC |
QR06AX12
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LIVERTOX |
939
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D016593
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256-710-8
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758627
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Terfenadine
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50679-08-8
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SUB10920MIG
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C29494
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3674
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7BA5G9Y06Q
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42330
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2600
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CHEMBL17157
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665802
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m10576
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100000082708
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2608
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DTXSID2023642
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DB00342
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6508
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Related Record | Type | Details | ||
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METABOLIC ENZYME -> INHIBITOR |
IC50
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TRANSPORTER -> INHIBITOR | |||
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BINDER->LIGAND |
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METABOLIC ENZYME -> SUBSTRATE | |||
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METABOLIC ENZYME -> SUBSTRATE | |||
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TARGET -> INHIBITOR |
BINDING
IC50
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METABOLIC ENZYME -> SUBSTRATE |
Related Record | Type | Details | ||
---|---|---|---|---|
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METABOLITE ACTIVE -> PARENT |
MAJOR
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METABOLITE -> PARENT |
URINE
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METABOLITE -> PARENT |
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URINE
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METABOLITE -> PARENT |
URINE
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METABOLITE -> PARENT |
URINE
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IMPURITY -> PARENT |
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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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||
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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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Related Record | Type | Details | ||
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ACTIVE MOIETY |
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