Details
Stereochemistry | RACEMIC |
Molecular Formula | C21H25ClN2O3.2ClH |
Molecular Weight | 461.81 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.Cl.OC(=O)COCCN1CCN(CC1)C(C2=CC=CC=C2)C3=CC=C(Cl)C=C3
InChI
InChIKey=PGLIUCLTXOYQMV-UHFFFAOYSA-N
InChI=1S/C21H25ClN2O3.2ClH/c22-19-8-6-18(7-9-19)21(17-4-2-1-3-5-17)24-12-10-23(11-13-24)14-15-27-16-20(25)26;;/h1-9,21H,10-16H2,(H,25,26);2*1H
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 |
Molecular Formula | C21H25ClN2O3 |
Molecular Weight | 388.888 |
Charge | 0 |
Count |
|
Stereochemistry | RACEMIC |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Optical Activity | ( + / - ) |
DescriptionSources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2004/19835slr016,21150slr005,30346slr011_zyrtec_lbl.pdfCurator's Comment: description was created based on several sources, including:
https://www.drugs.com/pro/cetirizine.html
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2004/19835slr016,21150slr005,30346slr011_zyrtec_lbl.pdf
Curator's Comment: description was created based on several sources, including:
https://www.drugs.com/pro/cetirizine.html
Cetirizine, a human metabolite of hydroxyzine, is an antihistamine; its principal effects are mediated via selective inhibition of peripheral H1 receptors. It is indicated for the relief of nasal and non-nasal symptoms associated with seasonal or perennial allergic rhinitis, hay fever and chronic idiopathic urticaria. Commonly reported adverse reactions of cetirizine include headache, dry mouth and drowsiness or fatigue. Pharmacokinetic interaction studies with Cetirizine in adults were conducted with pseudoephedrine, antipyrine, ketoconazole, erythromycin and azithromycin. No interactions were observed.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL231 |
8.2 null [pKi] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Palliative | ZYRTEC HIVES RELIEF Approved UseTablets should be administered when both the antihistaminic properties of cetirizine hydrochloride and the nasal decongestant properties of pseudoephedrine hydrochloride are desired. Launch Date1995 |
|||
Palliative | ZYRTEC HIVES RELIEF Approved UseTablets should be administered when both the antihistaminic properties of cetirizine hydrochloride and the nasal decongestant properties of pseudoephedrine hydrochloride are desired. Launch Date1995 |
|||
Palliative | ZYRTEC HIVES RELIEF Approved UseUses temporarily relieves these symptoms due to hay fever or other upper respiratory allergies: •runny nose •sneezing •itchy, watery eyes •itching of the nose or throat Launch Date1995 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
311 ng/mL |
10 mg 1 times / day multiple, oral dose: 10 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
CETIRIZINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
978.4 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2571627/ |
10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered: |
CETIRIZINE plasma | Homo sapiens population: UNHEALTHY age: CHILD sex: FEMALE / MALE food status: FASTED |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
6375.6 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2571627/ |
10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered: |
CETIRIZINE plasma | Homo sapiens population: UNHEALTHY age: CHILD sex: FEMALE / MALE food status: FASTED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
8.3 h |
10 mg 1 times / day multiple, oral dose: 10 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
CETIRIZINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
6.9 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2571627/ |
10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered: |
CETIRIZINE plasma | Homo sapiens population: UNHEALTHY age: CHILD sex: FEMALE / MALE food status: FASTED |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
7% |
10 mg 1 times / day multiple, oral dose: 10 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
CETIRIZINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
180 mg single, oral Overdose |
unhealthy, 18 months n = 1 Health Status: unhealthy Age Group: 18 months Sex: M Population Size: 1 Sources: |
|
270 mg single, oral Overdose |
unhealthy, 18 years n = 1 Health Status: unhealthy Age Group: 18 years Sex: F Population Size: 1 Sources: |
Other AEs: Metabolic acidosis, Hypokalemia... Other AEs: Metabolic acidosis (grade 5, 1 patient) Sources: Hypokalemia (grade 5, 1 patient) |
10 mg 1 times / day multiple, oral Recommended Dose: 10 mg, 1 times / day Route: oral Route: multiple Dose: 10 mg, 1 times / day Sources: |
unhealthy, 18 years n = 1 Health Status: unhealthy Condition: allergic rhinitis Age Group: 18 years Sex: F Population Size: 1 Sources: |
Disc. AE: Delusions, Depression... AEs leading to discontinuation/dose reduction: Delusions (1 patient) Sources: Depression (1 patient) |
2.5 mg 1 times / day multiple, oral Dose: 2.5 mg, 1 times / day Route: oral Route: multiple Dose: 2.5 mg, 1 times / day Sources: |
unhealthy, 23 months n = 1 Health Status: unhealthy Condition: chronic rhinitis Age Group: 23 months Sex: M Population Size: 1 Sources: |
Disc. AE: Insomnia... AEs leading to discontinuation/dose reduction: Insomnia (1 patient) Sources: |
10 mg single, intravenous Recommended Dose: 10 mg Route: intravenous Route: single Dose: 10 mg Sources: |
unhealthy, 39 years n = 127 Health Status: unhealthy Condition: acute urticaria Age Group: 39 years Sex: M+F Population Size: 127 Sources: |
Other AEs: Dyspepsia, Feeling hot... Other AEs: Dyspepsia (1%) Sources: Feeling hot (1%) Dysgeusia (1%) Headache (1%) Paresthesia (1%) Presyncope (1%) Hyperhidrosis (1%) |
60 mg single, oral Overdose |
healthy, 4 years n = 1 Health Status: healthy Age Group: 4 years Sex: M Population Size: 1 Sources: |
Other AEs: Drowsiness, Sedation... Other AEs: Drowsiness (severe, 1 patient) Sources: Sedation (1 patient) |
50 mg 1 times / day multiple, oral Dose: 50 mg, 1 times / day Route: oral Route: multiple Dose: 50 mg, 1 times / day Sources: |
unhealthy, 46 years n = 1 Health Status: unhealthy Condition: chronic idiopathic urticaria Age Group: 46 years Sex: M Population Size: 1 Sources: |
|
5 mg 1 times / day multiple, oral Dose: 5 mg, 1 times / day Route: oral Route: multiple Dose: 5 mg, 1 times / day Sources: |
unhealthy, 6 years n = 1 Health Status: unhealthy Condition: allergic rhinitis Age Group: 6 years Sex: M Population Size: 1 Sources: |
Disc. AE: Dystonic reaction... AEs leading to discontinuation/dose reduction: Dystonic reaction (1 patient) Sources: |
10 mg 1 times / day multiple, oral Recommended Dose: 10 mg, 1 times / day Route: oral Route: multiple Dose: 10 mg, 1 times / day Sources: Page: p. 24 |
unhealthy, > 12 years n = 2034 Health Status: unhealthy Age Group: > 12 years Sex: M+F Population Size: 2034 Sources: Page: p. 24 |
Other AEs: Somnolence, Fatigue... Other AEs: Somnolence (13.7%) Sources: Page: p. 24Fatigue (5.9%) Dry mouth (5%) Dizziness (2%) Pharyngitis (2%) |
0.24 % 2 times / day multiple, ophthalmic Recommended Dose: 0.24 %, 2 times / day Route: ophthalmic Route: multiple Dose: 0.24 %, 2 times / day Sources: |
unhealthy, adult n = 511 Health Status: unhealthy Condition: ocular itching Age Group: adult Population Size: 511 Sources: |
Other AEs: Ocular hyperemia, Visual acuity reduced... Other AEs: Ocular hyperemia (2%) Sources: Visual acuity reduced (0.6%) Conjunctival hyperemia (5.3%) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Hypokalemia | grade 5, 1 patient | 270 mg single, oral Overdose |
unhealthy, 18 years n = 1 Health Status: unhealthy Age Group: 18 years Sex: F Population Size: 1 Sources: |
Metabolic acidosis | grade 5, 1 patient | 270 mg single, oral Overdose |
unhealthy, 18 years n = 1 Health Status: unhealthy Age Group: 18 years Sex: F Population Size: 1 Sources: |
Delusions | 1 patient Disc. AE |
10 mg 1 times / day multiple, oral Recommended Dose: 10 mg, 1 times / day Route: oral Route: multiple Dose: 10 mg, 1 times / day Sources: |
unhealthy, 18 years n = 1 Health Status: unhealthy Condition: allergic rhinitis Age Group: 18 years Sex: F Population Size: 1 Sources: |
Depression | 1 patient Disc. AE |
10 mg 1 times / day multiple, oral Recommended Dose: 10 mg, 1 times / day Route: oral Route: multiple Dose: 10 mg, 1 times / day Sources: |
unhealthy, 18 years n = 1 Health Status: unhealthy Condition: allergic rhinitis Age Group: 18 years Sex: F Population Size: 1 Sources: |
Insomnia | 1 patient Disc. AE |
2.5 mg 1 times / day multiple, oral Dose: 2.5 mg, 1 times / day Route: oral Route: multiple Dose: 2.5 mg, 1 times / day Sources: |
unhealthy, 23 months n = 1 Health Status: unhealthy Condition: chronic rhinitis Age Group: 23 months Sex: M Population Size: 1 Sources: |
Dysgeusia | 1% | 10 mg single, intravenous Recommended Dose: 10 mg Route: intravenous Route: single Dose: 10 mg Sources: |
unhealthy, 39 years n = 127 Health Status: unhealthy Condition: acute urticaria Age Group: 39 years Sex: M+F Population Size: 127 Sources: |
Dyspepsia | 1% | 10 mg single, intravenous Recommended Dose: 10 mg Route: intravenous Route: single Dose: 10 mg Sources: |
unhealthy, 39 years n = 127 Health Status: unhealthy Condition: acute urticaria Age Group: 39 years Sex: M+F Population Size: 127 Sources: |
Feeling hot | 1% | 10 mg single, intravenous Recommended Dose: 10 mg Route: intravenous Route: single Dose: 10 mg Sources: |
unhealthy, 39 years n = 127 Health Status: unhealthy Condition: acute urticaria Age Group: 39 years Sex: M+F Population Size: 127 Sources: |
Headache | 1% | 10 mg single, intravenous Recommended Dose: 10 mg Route: intravenous Route: single Dose: 10 mg Sources: |
unhealthy, 39 years n = 127 Health Status: unhealthy Condition: acute urticaria Age Group: 39 years Sex: M+F Population Size: 127 Sources: |
Hyperhidrosis | 1% | 10 mg single, intravenous Recommended Dose: 10 mg Route: intravenous Route: single Dose: 10 mg Sources: |
unhealthy, 39 years n = 127 Health Status: unhealthy Condition: acute urticaria Age Group: 39 years Sex: M+F Population Size: 127 Sources: |
Paresthesia | 1% | 10 mg single, intravenous Recommended Dose: 10 mg Route: intravenous Route: single Dose: 10 mg Sources: |
unhealthy, 39 years n = 127 Health Status: unhealthy Condition: acute urticaria Age Group: 39 years Sex: M+F Population Size: 127 Sources: |
Presyncope | 1% | 10 mg single, intravenous Recommended Dose: 10 mg Route: intravenous Route: single Dose: 10 mg Sources: |
unhealthy, 39 years n = 127 Health Status: unhealthy Condition: acute urticaria Age Group: 39 years Sex: M+F Population Size: 127 Sources: |
Sedation | 1 patient | 60 mg single, oral Overdose |
healthy, 4 years n = 1 Health Status: healthy Age Group: 4 years Sex: M Population Size: 1 Sources: |
Drowsiness | severe, 1 patient | 60 mg single, oral Overdose |
healthy, 4 years n = 1 Health Status: healthy Age Group: 4 years Sex: M Population Size: 1 Sources: |
Dystonic reaction | 1 patient Disc. AE |
5 mg 1 times / day multiple, oral Dose: 5 mg, 1 times / day Route: oral Route: multiple Dose: 5 mg, 1 times / day Sources: |
unhealthy, 6 years n = 1 Health Status: unhealthy Condition: allergic rhinitis Age Group: 6 years Sex: M Population Size: 1 Sources: |
Somnolence | 13.7% | 10 mg 1 times / day multiple, oral Recommended Dose: 10 mg, 1 times / day Route: oral Route: multiple Dose: 10 mg, 1 times / day Sources: Page: p. 24 |
unhealthy, > 12 years n = 2034 Health Status: unhealthy Age Group: > 12 years Sex: M+F Population Size: 2034 Sources: Page: p. 24 |
Dizziness | 2% | 10 mg 1 times / day multiple, oral Recommended Dose: 10 mg, 1 times / day Route: oral Route: multiple Dose: 10 mg, 1 times / day Sources: Page: p. 24 |
unhealthy, > 12 years n = 2034 Health Status: unhealthy Age Group: > 12 years Sex: M+F Population Size: 2034 Sources: Page: p. 24 |
Pharyngitis | 2% | 10 mg 1 times / day multiple, oral Recommended Dose: 10 mg, 1 times / day Route: oral Route: multiple Dose: 10 mg, 1 times / day Sources: Page: p. 24 |
unhealthy, > 12 years n = 2034 Health Status: unhealthy Age Group: > 12 years Sex: M+F Population Size: 2034 Sources: Page: p. 24 |
Dry mouth | 5% | 10 mg 1 times / day multiple, oral Recommended Dose: 10 mg, 1 times / day Route: oral Route: multiple Dose: 10 mg, 1 times / day Sources: Page: p. 24 |
unhealthy, > 12 years n = 2034 Health Status: unhealthy Age Group: > 12 years Sex: M+F Population Size: 2034 Sources: Page: p. 24 |
Fatigue | 5.9% | 10 mg 1 times / day multiple, oral Recommended Dose: 10 mg, 1 times / day Route: oral Route: multiple Dose: 10 mg, 1 times / day Sources: Page: p. 24 |
unhealthy, > 12 years n = 2034 Health Status: unhealthy Age Group: > 12 years Sex: M+F Population Size: 2034 Sources: Page: p. 24 |
Visual acuity reduced | 0.6% | 0.24 % 2 times / day multiple, ophthalmic Recommended Dose: 0.24 %, 2 times / day Route: ophthalmic Route: multiple Dose: 0.24 %, 2 times / day Sources: |
unhealthy, adult n = 511 Health Status: unhealthy Condition: ocular itching Age Group: adult Population Size: 511 Sources: |
Ocular hyperemia | 2% | 0.24 % 2 times / day multiple, ophthalmic Recommended Dose: 0.24 %, 2 times / day Route: ophthalmic Route: multiple Dose: 0.24 %, 2 times / day Sources: |
unhealthy, adult n = 511 Health Status: unhealthy Condition: ocular itching Age Group: adult Population Size: 511 Sources: |
Conjunctival hyperemia | 5.3% | 0.24 % 2 times / day multiple, ophthalmic Recommended Dose: 0.24 %, 2 times / day Route: ophthalmic Route: multiple Dose: 0.24 %, 2 times / day Sources: |
unhealthy, adult n = 511 Health Status: unhealthy Condition: ocular itching Age Group: adult Population Size: 511 Sources: |
PubMed
Title | Date | PubMed |
---|---|---|
Measurement of interstitial cetirizine concentrations in human skin: correlation of drug levels with inhibition of histamine-induced skin responses. | 1999 Jun |
|
The acute and sub-chronic effects of levocetirizine, cetirizine, loratadine, promethazine and placebo on cognitive function, psychomotor performance, and weal and flare. | 2001 |
|
Twenty-four hours of activity of cetirizine and fexofenadine in the skin. | 2001 Apr |
|
Sure outcomes of random events: a model for clinical trials. | 2001 Feb 28 |
|
[Prednicarbate and cetirizin dihydrochloride in the treatment of atopic eczema in the acute phase in children]. | 2001 Jan |
|
Stability of cetirizine dihydrochloride in solid state. | 2001 Jan-Feb |
|
Lipophilicity behaviour of the Zwitterionic antihistamine cetirizine in phosphatidylcholine liposomes/water systems. | 2001 May |
|
[The course of allergy: principles for early diagnosis, prevention and early therapy of allergic diseases]. | 2001 May |
|
Efficacy and safety of an oral formulation of cetirizine and prolonged-release pseudoephedrine versus xylometazoline nasal spray in nasal congestion. | 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 |
|
Multiwavelength spectrophotometric resolution of the micro-equilibria of cetirizine. | 2001 Oct |
|
Cetirizine inhibits skin reactions but not mediator release in immediate and developing late-phase allergic cutaneous reactions. A double-blind, placebo-controlled study. | 2001 Sep |
|
Serum tryptase in allergic rhinitis: effect of cetirizine and fluticasone propionate treatment. | 2001 Sep-Oct |
|
Pharmacokinetics of cetirizine in tear fluid after a single oral dose. | 2002 |
|
Photosensitivity disorders: cause, effect and management. | 2002 |
|
A double-blind, randomized, single-dose, crossover comparison of levocetirizine with ebastine, fexofenadine, loratadine, mizolastine, and placebo: suppression of histamine-induced wheal-and-flare response during 24 hours in healthy male subjects. | 2002 Feb |
|
Binding characteristics of cetirizine and levocetirizine to human H(1) histamine receptors: contribution of Lys(191) and Thr(194). | 2002 Feb |
|
Randomised controlled trial of butterbur and cetirizine for treating seasonal allergic rhinitis. | 2002 Jan 19 |
|
Immune changes in patients with advanced breast cancer undergoing chemotherapy with taxanes. | 2002 Jul 1 |
|
Comparison of cetirizine, ebastine and loratadine in the treatment of immediate mosquito-bite allergy. | 2002 Jun |
|
Extractionless and sensitive method for high-throughput quantitation of cetirizine in human plasma samples by liquid chromatography-tandem mass spectrometry. | 2002 Jun 25 |
|
Effects of emedastine and cetirizine, alone and with alcohol, on actual driving of males and females. | 2002 Mar |
|
[Already allergic to pollen in early childhood. Can future asthma still be prevented?]. | 2002 Mar 7 |
|
Gateways to clinical trials. | 2002 May |
|
Urticarial intolerance reaction to cetirizine. | 2002 May |
|
Treating seasonal allergic rhinitis. Well designed experiments should have been used. | 2002 May 25 |
Sample Use Guides
1 to 2 tablets once daily depending upon severity of symptoms; do not take more than 2 tablets in 24 hours
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/7741033
Cetirizine (10 micrograms/ml) significantly enhanced IL-1 release by human monocytes stimulated by a weak LPS concentration (1 microgram/ml) but could not modify the maximal increase of IL-1 release induced by 10 micrograms/ml of LPS. It did not exert any effect on resting cells. Cetirizine (0.1-10 micrograms/ml) enhanced PGE2 release by resting human monocytes. Concentrations of 1 and 10 micrograms/ml enhanced PGE2 release by LPS-stimulated monocytes, and by healthy and inflamed rat macrophages.
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 17:35:58 GMT 2023
by
admin
on
Fri Dec 15 17:35:58 GMT 2023
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Record UNII |
64O047KTOA
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Record Status |
Validated (UNII)
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Record Version |
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-
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NCI_THESAURUS |
C29578
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SUB11803MIG
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m3291
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83881-52-1
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759102
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CHEMBL1000
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Related Record | Type | Details | ||
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TRANSPORTER -> INHIBITOR | |||
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PARENT -> SALT/SOLVATE | |||
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BASIS OF STRENGTH->SUBSTANCE |
ASSAY (HPLC)
USP
|
Related Record | Type | Details | ||
---|---|---|---|---|
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
|
||
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
|
||
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
|
||
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
|
||
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
|
||
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
||
|
IMPURITY -> PARENT | |||
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
|
||
|
IMPURITY -> PARENT |
For the calculation of content, multiply the peak areas by 0.7
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
||
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
|
||
|
IMPURITY -> PARENT |
For the calculation of content, multiply the peak areas by 0.6
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
||
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
|
||
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
||
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
|
||
|
IMPURITY -> PARENT |
For the calculation of content, multiply the peak areas by 1.9
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
||
|
IMPURITY -> PARENT |
For the calculation of content, multiply the peak areas by 1.3
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
||
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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Related Record | Type | Details | ||
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ACTIVE MOIETY |