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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
Structure of Cetirizine hydrochloride

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

HIDE SMILES / InChI

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 ( + / - )

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

Description
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.

CNS Activity

Approval Year

Targets

Targets

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
ZYRTEC HIVES RELIEF

Approved Use

Tablets should be administered when both the antihistaminic properties of cetirizine hydrochloride and the nasal decongestant properties of pseudoephedrine hydrochloride are desired.

Launch Date

1995
Palliative
ZYRTEC HIVES RELIEF

Approved Use

Tablets should be administered when both the antihistaminic properties of cetirizine hydrochloride and the nasal decongestant properties of pseudoephedrine hydrochloride are desired.

Launch Date

1995
Palliative
ZYRTEC HIVES RELIEF

Approved Use

Uses 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 Date

1995
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
978.4 ng/mL
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
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
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
6375.6 ng × h/mL
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

T1/2

ValueDoseCo-administeredAnalytePopulation
6.9 h
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
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
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
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

Doses

DosePopulationAdverse events​
180 mg single, oral
Overdose
Dose: 180 mg
Route: oral
Route: single
Dose: 180 mg
Sources:
unhealthy, 18 months
Health Status: unhealthy
Age Group: 18 months
Sex: M
Sources:
270 mg single, oral
Overdose
Dose: 270 mg
Route: oral
Route: single
Dose: 270 mg
Sources:
unhealthy, 18 years
Health Status: unhealthy
Age Group: 18 years
Sex: F
Sources:
Other AEs: Metabolic acidosis, Hypokalemia...
Other AEs:
Metabolic acidosis (grade 5, 1 patient)
Hypokalemia (grade 5, 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:
unhealthy, 18 years
Health Status: unhealthy
Age Group: 18 years
Sex: F
Sources:
Disc. AE: Delusions, Depression...
AEs leading to
discontinuation/dose reduction:
Delusions (1 patient)
Depression (1 patient)
Sources:
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
Health Status: unhealthy
Age Group: 23 months
Sex: M
Sources:
Disc. AE: Insomnia...
AEs leading to
discontinuation/dose reduction:
Insomnia (1 patient)
Sources:
10 mg single, intravenous
Recommended
unhealthy, 39 years
Other AEs: Dyspepsia, Feeling hot...
Other AEs:
Dyspepsia (1%)
Feeling hot (1%)
Dysgeusia (1%)
Headache (1%)
Paresthesia (1%)
Presyncope (1%)
Hyperhidrosis (1%)
Sources:
60 mg single, oral
Overdose
Dose: 60 mg
Route: oral
Route: single
Dose: 60 mg
Sources:
healthy, 4 years
Health Status: healthy
Age Group: 4 years
Sex: M
Sources:
Other AEs: Drowsiness, Sedation...
Other AEs:
Drowsiness (severe, 1 patient)
Sedation (1 patient)
Sources:
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
Health Status: unhealthy
Age Group: 46 years
Sex: M
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
Health Status: unhealthy
Age Group: 6 years
Sex: M
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:
unhealthy, > 12 years
Health Status: unhealthy
Age Group: > 12 years
Sex: M+F
Sources:
Other AEs: Somnolence, Fatigue...
Other AEs:
Somnolence (13.7%)
Fatigue (5.9%)
Dry mouth (5%)
Dizziness (2%)
Pharyngitis (2%)
Sources:
0.24 % 2 times / day multiple, ophthalmic
Recommended
unhealthy, adult
Other AEs: Ocular hyperemia, Visual acuity reduced...
AEs

AEs

AESignificanceDosePopulation
Hypokalemia grade 5, 1 patient
270 mg single, oral
Overdose
Dose: 270 mg
Route: oral
Route: single
Dose: 270 mg
Sources:
unhealthy, 18 years
Health Status: unhealthy
Age Group: 18 years
Sex: F
Sources:
Metabolic acidosis grade 5, 1 patient
270 mg single, oral
Overdose
Dose: 270 mg
Route: oral
Route: single
Dose: 270 mg
Sources:
unhealthy, 18 years
Health Status: unhealthy
Age Group: 18 years
Sex: F
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
Health Status: unhealthy
Age Group: 18 years
Sex: F
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
Health Status: unhealthy
Age Group: 18 years
Sex: F
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
Health Status: unhealthy
Age Group: 23 months
Sex: M
Sources:
Dysgeusia 1%
10 mg single, intravenous
Recommended
unhealthy, 39 years
Dyspepsia 1%
10 mg single, intravenous
Recommended
unhealthy, 39 years
Feeling hot 1%
10 mg single, intravenous
Recommended
unhealthy, 39 years
Headache 1%
10 mg single, intravenous
Recommended
unhealthy, 39 years
Hyperhidrosis 1%
10 mg single, intravenous
Recommended
unhealthy, 39 years
Paresthesia 1%
10 mg single, intravenous
Recommended
unhealthy, 39 years
Presyncope 1%
10 mg single, intravenous
Recommended
unhealthy, 39 years
Sedation 1 patient
60 mg single, oral
Overdose
Dose: 60 mg
Route: oral
Route: single
Dose: 60 mg
Sources:
healthy, 4 years
Health Status: healthy
Age Group: 4 years
Sex: M
Sources:
Drowsiness severe, 1 patient
60 mg single, oral
Overdose
Dose: 60 mg
Route: oral
Route: single
Dose: 60 mg
Sources:
healthy, 4 years
Health Status: healthy
Age Group: 4 years
Sex: M
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
Health Status: unhealthy
Age Group: 6 years
Sex: M
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:
unhealthy, > 12 years
Health Status: unhealthy
Age Group: > 12 years
Sex: M+F
Sources:
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:
unhealthy, > 12 years
Health Status: unhealthy
Age Group: > 12 years
Sex: M+F
Sources:
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:
unhealthy, > 12 years
Health Status: unhealthy
Age Group: > 12 years
Sex: M+F
Sources:
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:
unhealthy, > 12 years
Health Status: unhealthy
Age Group: > 12 years
Sex: M+F
Sources:
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:
unhealthy, > 12 years
Health Status: unhealthy
Age Group: > 12 years
Sex: M+F
Sources:
Visual acuity reduced 0.6%
0.24 % 2 times / day multiple, ophthalmic
Recommended
unhealthy, adult
Ocular hyperemia 2%
0.24 % 2 times / day multiple, ophthalmic
Recommended
unhealthy, adult
Conjunctival hyperemia 5.3%
0.24 % 2 times / day multiple, ophthalmic
Recommended
unhealthy, adult
PubMed

PubMed

TitleDatePubMed
Cetirizine and loratadine: a comparison using the ED50 in skin reactions.
2000 Mar-Apr
Clinical prescribing of allergic rhinitis medication in the preschool and young school-age child: what are the options?
2001
Cetirizine reduces the number of tryptase-positive mast cells in psoriatic patients: a double-blind controlled study.
2001
Treatment of severe seasonal rhinoconjunctivitis by a combination of azelastine nasal spray and eye drops: a double-blind, double-placebo study.
2001
Twenty-four hours of activity of cetirizine and fexofenadine in the skin.
2001 Apr
Newer antihistamines.
2001 Apr 30
[The allergic pregnant woman].
2001 Dec
[Prednicarbate and cetirizin dihydrochloride in the treatment of atopic eczema in the acute phase in children].
2001 Jan
Effects of monotherapy with intra-nasal corticosteroid or combined oral histamine and leukotriene receptor antagonists in seasonal allergic rhinitis.
2001 Jan
Urticaria induced by cetirizine.
2001 Jan
Effect of cetirizine on bronchial hyperresponsiveness in patients with seasonal allergic rhinitis and asthma.
2001 Jan
Double-blind multicenter study on the efficacy and tolerability of cetirizine compared with oxatomide in chronic idiopathic urticaria in preschool children.
2001 Jul
Severe hepatitis in a patient taking cetirizine.
2001 Jul 17
Antihistamines and the torsade de point in children with allergic rhinitis.
2001 Jul-Aug
Burn wound itch control using H1 and H2 antagonists.
2001 Jul-Aug
Stanozolol in chronic urticaria: a double blind, placebo controlled trial.
2001 Jun
[Co-administration of histamine H1 antagonist and oral anticoagulants].
2001 Jun-Jul
Local safety of intranasal triamcinolone acetonide: clinical and histological aspects of nasal mucosa in the long-term treatment of perennial allergic rhinitis.
2001 Mar
An investigation into the effects of cetirizine on cognitive function and psychomotor performance in healthy volunteers.
2001 Mar
Lipophilicity behaviour of the Zwitterionic antihistamine cetirizine in phosphatidylcholine liposomes/water systems.
2001 May
Acute urticaria with elevated circulating interleukin-6 is resistant to anti-histamine treatment.
2001 May
[The course of allergy: principles for early diagnosis, prevention and early therapy of allergic diseases].
2001 May
Preclinical comparison of ebastine and other second generation H1-antihistamines.
2001 Oct
Antiallergic/antiasthmatic effect of novel antiallergic hexapeptide-95/220 in various experimental models.
2001 Sep
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
Potential cardiac toxicity of H1-antihistamines.
2002
Pharmacokinetics of cetirizine in tear fluid after a single oral dose.
2002
Photosensitivity disorders: cause, effect and management.
2002
Effects of antihistamines on leukotriene and cytokine release from dispersed nasal polyp cells.
2002
[The first case of lasting pigmented toxidermia induced by cetirizine (Zyrtec, Virlix) and ticlopidine].
2002 Apr
Major role for the carboxylic function of cetirizine and levocetirizine in their binding characteristics to human H1-histamine-receptors.
2002 Apr
Binding characteristics of [3H]levocetirizine to cloned human H1-histamine-receptors expressed in CHO cells.
2002 Apr
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
Cardiotoxicity of new antihistamines and cisapride.
2002 Feb 28
Titrimetric and spectrophotometric assay of some antihistamines through the determination of the chloride of their hydrochlorides.
2002 Jan
Randomised controlled trial of butterbur and cetirizine for treating seasonal allergic rhinitis.
2002 Jan 19
Gateways to clinical trials.
2002 Jan-Feb
Lack of effect of single and repeated doses of levocetirizine, a new antihistamine drug, on cognitive and psychomotor functions in healthy volunteers.
2002 Jul
Immune changes in patients with advanced breast cancer undergoing chemotherapy with taxanes.
2002 Jul 1
Extractionless and sensitive method for high-throughput quantitation of cetirizine in human plasma samples by liquid chromatography-tandem mass spectrometry.
2002 Jun 25
Comparative activity of cetirizine and mizolastine on histamine-induced skin wheal and flare responses at 24 h.
2002 Mar
Gateways to clinical trials.
2002 May
Urticarial intolerance reaction to cetirizine.
2002 May
Development and validation of a HPLC method for the determination of cetirizine in pharmaceutical dosage forms.
2002 May
Treating seasonal allergic rhinitis. Trial does not show that there is no difference between butterbur and cetirizine.
2002 May 25
Patents

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
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 Mon Mar 31 18:49:09 GMT 2025
Edited
by admin
on Mon Mar 31 18:49:09 GMT 2025
Record UNII
64O047KTOA
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
Cetirizine hydrochloride
JAN   MART.   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD  
USAN  
Official Name English
Cetirizine dihydrochloride
EP   MI  
Preferred Name English
Cetirizine hydrochloride [USP MONOGRAPH]
Common Name English
Cetirizine hydrochloride [VANDF]
Common Name English
Cetirizine HCL
Common Name English
Acetic acid, [2-[4-[(4-chlorophenyl)phenylmethyl]-1-piperazinyl]ethoxy]-, dihydrochloride, (±)-
Common Name English
QUZYTTIR
Brand Name English
Cetirizine dihydrochloride [EP MONOGRAPH]
Common Name English
Cetirizine hydrochloride [USP-RS]
Common Name English
NSC-759102
Code English
(±)-(2-(4-(P-Chloro-a-phenylbenzyl)-1-piperazinyl)ethoxy)acetic acid, dihydrochloride
Systematic Name English
ZYRTEC
Brand Name English
Cetirizine hydrochloride [ORANGE BOOK]
Common Name English
Cetirizine dihydrochloride [MI]
Common Name English
Cetrine
Brand Name English
Cetirizine hydrochloride [MART.]
Common Name English
Cetirizine hydrochloride [JAN]
Common Name English
P-071
Code English
2-(2-[4-[(4-Chlorophenyl)(phenyl)methyl]piperazin-1-yl]ethoxy)acetic acid dihydrochloride
Systematic Name English
Cetirizine hydrochloride [USAN]
Common Name English
ZERVIATE
Brand Name English
Cetirizine hydrochloride [WHO-DD]
Common Name English
P071
Code English
ZYRTEC-D COMPONENT CETIRIZINE HYDROCHLORIDE
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C29578
Created by admin on Mon Mar 31 18:49:09 GMT 2025 , Edited by admin on Mon Mar 31 18:49:09 GMT 2025
Code System Code Type Description
RXCUI
203150
Created by admin on Mon Mar 31 18:49:09 GMT 2025 , Edited by admin on Mon Mar 31 18:49:09 GMT 2025
PRIMARY RxNorm
EVMPD
SUB11803MIG
Created by admin on Mon Mar 31 18:49:09 GMT 2025 , Edited by admin on Mon Mar 31 18:49:09 GMT 2025
PRIMARY
DAILYMED
64O047KTOA
Created by admin on Mon Mar 31 18:49:09 GMT 2025 , Edited by admin on Mon Mar 31 18:49:09 GMT 2025
PRIMARY
EPA CompTox
DTXSID2044268
Created by admin on Mon Mar 31 18:49:09 GMT 2025 , Edited by admin on Mon Mar 31 18:49:09 GMT 2025
PRIMARY
RS_ITEM_NUM
1102929
Created by admin on Mon Mar 31 18:49:09 GMT 2025 , Edited by admin on Mon Mar 31 18:49:09 GMT 2025
PRIMARY
SMS_ID
100000091468
Created by admin on Mon Mar 31 18:49:09 GMT 2025 , Edited by admin on Mon Mar 31 18:49:09 GMT 2025
PRIMARY
USAN
X-17
Created by admin on Mon Mar 31 18:49:09 GMT 2025 , Edited by admin on Mon Mar 31 18:49:09 GMT 2025
PRIMARY
MERCK INDEX
m3291
Created by admin on Mon Mar 31 18:49:09 GMT 2025 , Edited by admin on Mon Mar 31 18:49:09 GMT 2025
PRIMARY Merck Index
CAS
83881-52-1
Created by admin on Mon Mar 31 18:49:09 GMT 2025 , Edited by admin on Mon Mar 31 18:49:09 GMT 2025
PRIMARY
NCI_THESAURUS
C28920
Created by admin on Mon Mar 31 18:49:09 GMT 2025 , Edited by admin on Mon Mar 31 18:49:09 GMT 2025
PRIMARY
PUBCHEM
55182
Created by admin on Mon Mar 31 18:49:09 GMT 2025 , Edited by admin on Mon Mar 31 18:49:09 GMT 2025
PRIMARY
FDA UNII
64O047KTOA
Created by admin on Mon Mar 31 18:49:09 GMT 2025 , Edited by admin on Mon Mar 31 18:49:09 GMT 2025
PRIMARY
DRUG BANK
DBSALT001214
Created by admin on Mon Mar 31 18:49:09 GMT 2025 , Edited by admin on Mon Mar 31 18:49:09 GMT 2025
PRIMARY
NSC
759102
Created by admin on Mon Mar 31 18:49:09 GMT 2025 , Edited by admin on Mon Mar 31 18:49:09 GMT 2025
PRIMARY
ChEMBL
CHEMBL1000
Created by admin on Mon Mar 31 18:49:09 GMT 2025 , Edited by admin on Mon Mar 31 18:49:09 GMT 2025
PRIMARY
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For the calculation of content, multiply the peak areas by 0.7
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For the calculation of content, multiply the peak areas by 0.6
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For the calculation of content, multiply the peak areas by 1.9
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IMPURITY -> PARENT
For the calculation of content, multiply the peak areas by 1.3
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ACTIVE MOIETY