U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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 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 ( + / - )

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
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
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

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
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
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

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
n = 1
Health Status: unhealthy
Age Group: 18 months
Sex: M
Population Size: 1
Sources:
270 mg single, oral
Overdose
Dose: 270 mg
Route: oral
Route: single
Dose: 270 mg
Sources:
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)
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
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)
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
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
unhealthy, 39 years
n = 127
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
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)
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
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%)
Fatigue (5.9%)
Dry mouth (5%)
Dizziness (2%)
Pharyngitis (2%)
Sources: Page: p. 24
0.24 % 2 times / day multiple, ophthalmic
Recommended
unhealthy, adult
n = 511
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
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
Dose: 270 mg
Route: oral
Route: single
Dose: 270 mg
Sources:
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
unhealthy, 39 years
n = 127
Dyspepsia 1%
10 mg single, intravenous
Recommended
unhealthy, 39 years
n = 127
Feeling hot 1%
10 mg single, intravenous
Recommended
unhealthy, 39 years
n = 127
Headache 1%
10 mg single, intravenous
Recommended
unhealthy, 39 years
n = 127
Hyperhidrosis 1%
10 mg single, intravenous
Recommended
unhealthy, 39 years
n = 127
Paresthesia 1%
10 mg single, intravenous
Recommended
unhealthy, 39 years
n = 127
Presyncope 1%
10 mg single, intravenous
Recommended
unhealthy, 39 years
n = 127
Sedation 1 patient
60 mg single, oral
Overdose
Dose: 60 mg
Route: oral
Route: single
Dose: 60 mg
Sources:
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
Dose: 60 mg
Route: oral
Route: single
Dose: 60 mg
Sources:
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
unhealthy, adult
n = 511
Ocular hyperemia 2%
0.24 % 2 times / day multiple, ophthalmic
Recommended
unhealthy, adult
n = 511
Conjunctival hyperemia 5.3%
0.24 % 2 times / day multiple, ophthalmic
Recommended
unhealthy, adult
n = 511
PubMed

PubMed

TitleDatePubMed
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
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 Fri Dec 15 17:35:58 GMT 2023
Edited
by admin
on Fri Dec 15 17:35:58 GMT 2023
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 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
Common 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-(P-CHLORO-ALPHA-PHENYLBENZYL)1-PIPERAZINYL)ETHOXY) ACETIC ACID DIHYDROCHLORIDE
Systematic Name English
CETIRIZINE HYDROCHLORIDE [USAN]
Common Name English
CETIRIZINE HYDROCHLORIDE COMPONENT OF ZYRTEC-D
Common Name English
ZERVIATE
Brand Name English
CETIRIZINE DIHYDROCHLORIDE
EP   MI  
Common Name English
Cetirizine hydrochloride [WHO-DD]
Common Name English
P 071
Code English
ZYRTEC-D COMPONENT CETIRIZINE HYDROCHLORIDE
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C29578
Created by admin on Fri Dec 15 17:35:58 GMT 2023 , Edited by admin on Fri Dec 15 17:35:58 GMT 2023
Code System Code Type Description
RXCUI
203150
Created by admin on Fri Dec 15 17:35:58 GMT 2023 , Edited by admin on Fri Dec 15 17:35:58 GMT 2023
PRIMARY RxNorm
EVMPD
SUB11803MIG
Created by admin on Fri Dec 15 17:35:58 GMT 2023 , Edited by admin on Fri Dec 15 17:35:58 GMT 2023
PRIMARY
DAILYMED
64O047KTOA
Created by admin on Fri Dec 15 17:35:58 GMT 2023 , Edited by admin on Fri Dec 15 17:35:58 GMT 2023
PRIMARY
EPA CompTox
DTXSID2044268
Created by admin on Fri Dec 15 17:35:58 GMT 2023 , Edited by admin on Fri Dec 15 17:35:58 GMT 2023
PRIMARY
RS_ITEM_NUM
1102929
Created by admin on Fri Dec 15 17:35:58 GMT 2023 , Edited by admin on Fri Dec 15 17:35:58 GMT 2023
PRIMARY
SMS_ID
100000091468
Created by admin on Fri Dec 15 17:35:58 GMT 2023 , Edited by admin on Fri Dec 15 17:35:58 GMT 2023
PRIMARY
USAN
X-17
Created by admin on Fri Dec 15 17:35:58 GMT 2023 , Edited by admin on Fri Dec 15 17:35:58 GMT 2023
PRIMARY
MERCK INDEX
m3291
Created by admin on Fri Dec 15 17:35:58 GMT 2023 , Edited by admin on Fri Dec 15 17:35:58 GMT 2023
PRIMARY Merck Index
CAS
83881-52-1
Created by admin on Fri Dec 15 17:35:58 GMT 2023 , Edited by admin on Fri Dec 15 17:35:58 GMT 2023
PRIMARY
NCI_THESAURUS
C28920
Created by admin on Fri Dec 15 17:35:58 GMT 2023 , Edited by admin on Fri Dec 15 17:35:58 GMT 2023
PRIMARY
PUBCHEM
55182
Created by admin on Fri Dec 15 17:35:58 GMT 2023 , Edited by admin on Fri Dec 15 17:35:58 GMT 2023
PRIMARY
FDA UNII
64O047KTOA
Created by admin on Fri Dec 15 17:35:58 GMT 2023 , Edited by admin on Fri Dec 15 17:35:58 GMT 2023
PRIMARY
DRUG BANK
DBSALT001214
Created by admin on Fri Dec 15 17:35:58 GMT 2023 , Edited by admin on Fri Dec 15 17:35:58 GMT 2023
PRIMARY
NSC
759102
Created by admin on Fri Dec 15 17:35:58 GMT 2023 , Edited by admin on Fri Dec 15 17:35:58 GMT 2023
PRIMARY
ChEMBL
CHEMBL1000
Created by admin on Fri Dec 15 17:35:58 GMT 2023 , Edited by admin on Fri Dec 15 17:35:58 GMT 2023
PRIMARY
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