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Details

Stereochemistry RACEMIC
Molecular Formula C18H20N3O3S.Na
Molecular Weight 381.4262
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of RABEPRAZOLE SODIUM

SMILES

Cc1c(CS(=O)c2nc3ccccc3[n-]2)nccc1OCCCOC.[Na+]

InChI

InChIKey=KRCQSTCYZUOBHN-UHFFFAOYSA-N
InChI=1S/C18H20N3O3S.Na/c1-13-16(19-9-8-17(13)24-11-5-10-23-2)12-25(22)18-20-14-6-3-4-7-15(14)21-18;/h3-4,6-9H,5,10-12H2,1-2H3;/q-1;+1

HIDE SMILES / InChI

Molecular Formula Na
Molecular Weight 22.9898
Charge 1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C18H21N3O3S
Molecular Weight 359.4444
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment:: http://www.accessdata.fda.gov/drugsatfda_docs/label/1999/20973lbl.pdf

Rabeprazole sodium was discovered by Eisai Co., Ltd. Janssen Pharmaceutica N.V. and Eisai Co., Ltd. have a strategic alliance in which Eisai and Janssen-Cilag co-promote the drug in Germany and the U.K. In the US rabeprazole sodium is co-promoted under the brand name AcipHex by Eisai Inc. and Janssen Pharmaceutica Inc. Pariet is available through Janssen-Cilag in most other countries excluding Japan and some Asian countries. Rabeprazole is an antiulcer drug in the class of proton pump inhibitors. Rabeprazole is a prodrug and is converted to the active sulphenamide form in the acid environment of the parietal cells. Rabeprazole is used to heal and maintain the healing of Erosive or Ulcerative Gastroesophageal Reflux Disease (GERD), for healing Duodenal Ulcers, and for treatment of pathological hypersecretory conditions such as Zollinger-Ellison Syndrome. Rabeprazole suppresses gastric acid secretion by inhibiting the gastric H+, K+ATPase at the secretory surface of the gastric parietal cell and does not exhibit anticholinergic or histamine H2-receptor antagonist properties. Because this enzyme is regarded as the acid (proton) pump within the parietal cell, rabeprazole has been characterized as a gastric proton-pump inhibitor which blocks the final step of gastric acid secretion. In gastric parietal cells, rabeprazole is protonated, accumulates, and is transformed to an active sulfonamide.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
ACIPHEX

Approved Use

ACIPHEX is a proton-pump inhibitor (PPI) indicated in adults for: Healing of Erosive or Ulcerative Gastroesophageal Reflux Disease (GERD) ( ) 1.1 Maintenance of Healing of Erosive or Ulcerative GERD ( ) 1.2 Treatment of Symptomatic GERD ( ) 1.3 Healing of Duodenal Ulcers ( ) 1.4 Eradication to Reduce the Risk of Duodenal Ulcer Recurrence ( ) Helicobacter pylori 1.5 Treatment of Pathological Hypersecretory Conditions, Including Zollinger-Ellison Syndrome ( ) 1.6 In adolescent patients 12 years of age and older for: Short-term treatment of Symptomatic GERD ( ) 1.7 In pediatric patients 1 to 11 years of age for: Treatment of GERD ( ) 1.8 1.1 Healing of Erosive or Ulcerative GERD in Adults ACIPHEX is indicated for short-term (4 to 8 weeks) treatment in the healing and symptomatic relief of erosive or ulcerative gastroesophageal reflux disease (GERD). For those patients who have not healed after 8 weeks of treatment, an additional 8-week course of ACIPHEX may be considered. 1.2 Maintenance of Healing of Erosive or Ulcerative GERD in Adults ACIPHEX is indicated for maintaining healing and reduction in relapse rates of heartburn symptoms in patients with erosive or ulcerative gastroesophageal reflux disease (GERD Maintenance). Controlled studies do not extend beyond 12 months. 1.3 Treatment of Symptomatic GERD in Adults ACIPHEX is indicated for the treatment of daytime and nighttime heartburn and other symptoms associated with GERD in adults 1.4 Healing of Duodenal Ulcers in Adults ACIPHEX is indicated for short-term (up to four weeks) treatment in the healing and symptomatic relief of duodenal ulcers. Most patients heal within four weeks. 1.5 Eradication to Reduce the Risk of Duodenal Ulcer Recurrence in Adults Helicobacter pylori ACIPHEX in combination with amoxicillin and clarithromycin as a three drug regimen, is indicated for the treatment of patients with infection and duodenal ulcer disease (active or history within the past 5 years) to eradicate . Eradication of has been shown to reduce the risk of duodenal ulcer recurrence [ and

Launch Date

935020800000
Primary
ACIPHEX

Approved Use

ACIPHEX is a proton-pump inhibitor (PPI) indicated in adults for: Healing of Erosive or Ulcerative Gastroesophageal Reflux Disease (GERD) ( ) 1.1 Maintenance of Healing of Erosive or Ulcerative GERD ( ) 1.2 Treatment of Symptomatic GERD ( ) 1.3 Healing of Duodenal Ulcers ( ) 1.4 Eradication to Reduce the Risk of Duodenal Ulcer Recurrence ( ) Helicobacter pylori 1.5 Treatment of Pathological Hypersecretory Conditions, Including Zollinger-Ellison Syndrome ( ) 1.6 In adolescent patients 12 years of age and older for: Short-term treatment of Symptomatic GERD ( ) 1.7 In pediatric patients 1 to 11 years of age for: Treatment of GERD ( ) 1.8 1.1 Healing of Erosive or Ulcerative GERD in Adults ACIPHEX is indicated for short-term (4 to 8 weeks) treatment in the healing and symptomatic relief of erosive or ulcerative gastroesophageal reflux disease (GERD). For those patients who have not healed after 8 weeks of treatment, an additional 8-week course of ACIPHEX may be considered. 1.2 Maintenance of Healing of Erosive or Ulcerative GERD in Adults ACIPHEX is indicated for maintaining healing and reduction in relapse rates of heartburn symptoms in patients with erosive or ulcerative gastroesophageal reflux disease (GERD Maintenance). Controlled studies do not extend beyond 12 months. 1.3 Treatment of Symptomatic GERD in Adults ACIPHEX is indicated for the treatment of daytime and nighttime heartburn and other symptoms associated with GERD in adults 1.4 Healing of Duodenal Ulcers in Adults ACIPHEX is indicated for short-term (up to four weeks) treatment in the healing and symptomatic relief of duodenal ulcers. Most patients heal within four weeks. 1.5 Eradication to Reduce the Risk of Duodenal Ulcer Recurrence in Adults Helicobacter pylori ACIPHEX in combination with amoxicillin and clarithromycin as a three drug regimen, is indicated for the treatment of patients with infection and duodenal ulcer disease (active or history within the past 5 years) to eradicate . Eradication of has been shown to reduce the risk of duodenal ulcer recurrence [ and

Launch Date

935020800000
Primary
ACIPHEX

Approved Use

ACIPHEX is a proton-pump inhibitor (PPI) indicated in adults for: Healing of Erosive or Ulcerative Gastroesophageal Reflux Disease (GERD) ( ) 1.1 Maintenance of Healing of Erosive or Ulcerative GERD ( ) 1.2 Treatment of Symptomatic GERD ( ) 1.3 Healing of Duodenal Ulcers ( ) 1.4 Eradication to Reduce the Risk of Duodenal Ulcer Recurrence ( ) Helicobacter pylori 1.5 Treatment of Pathological Hypersecretory Conditions, Including Zollinger-Ellison Syndrome ( ) 1.6 In adolescent patients 12 years of age and older for: Short-term treatment of Symptomatic GERD ( ) 1.7 In pediatric patients 1 to 11 years of age for: Treatment of GERD ( ) 1.8 1.1 Healing of Erosive or Ulcerative GERD in Adults ACIPHEX is indicated for short-term (4 to 8 weeks) treatment in the healing and symptomatic relief of erosive or ulcerative gastroesophageal reflux disease (GERD). For those patients who have not healed after 8 weeks of treatment, an additional 8-week course of ACIPHEX may be considered. 1.2 Maintenance of Healing of Erosive or Ulcerative GERD in Adults ACIPHEX is indicated for maintaining healing and reduction in relapse rates of heartburn symptoms in patients with erosive or ulcerative gastroesophageal reflux disease (GERD Maintenance). Controlled studies do not extend beyond 12 months. 1.3 Treatment of Symptomatic GERD in Adults ACIPHEX is indicated for the treatment of daytime and nighttime heartburn and other symptoms associated with GERD in adults 1.4 Healing of Duodenal Ulcers in Adults ACIPHEX is indicated for short-term (up to four weeks) treatment in the healing and symptomatic relief of duodenal ulcers. Most patients heal within four weeks. 1.5 Eradication to Reduce the Risk of Duodenal Ulcer Recurrence in Adults Helicobacter pylori ACIPHEX in combination with amoxicillin and clarithromycin as a three drug regimen, is indicated for the treatment of patients with infection and duodenal ulcer disease (active or history within the past 5 years) to eradicate . Eradication of has been shown to reduce the risk of duodenal ulcer recurrence [ and

Launch Date

935020800000
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
1.54 ng/mL
10 mg single, oral
dose: 10 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
RABEPRAZOLE blood
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
0.406 μg/mL
20 mg single, oral
dose: 20 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
RABEPRAZOLE unknown
Homo sapiens
population: HEALTHY
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
2.5 μg/mL
80 mg single, oral
dose: 80 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
RABEPRAZOLE unknown
Homo sapiens
population: HEALTHY
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
2.15 ng × h/mL
10 mg single, oral
dose: 10 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
RABEPRAZOLE blood
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
0.809 μg × h/mL
20 mg single, oral
dose: 20 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
RABEPRAZOLE unknown
Homo sapiens
population: HEALTHY
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
5.212 μg × h/mL
80 mg single, oral
dose: 80 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
RABEPRAZOLE unknown
Homo sapiens
population: HEALTHY
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
3.46 h
10 mg single, oral
dose: 10 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
RABEPRAZOLE blood
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
1.02 h
20 mg single, oral
dose: 20 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
RABEPRAZOLE unknown
Homo sapiens
population: HEALTHY
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
1.21 h
80 mg single, oral
dose: 80 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
RABEPRAZOLE unknown
Homo sapiens
population: HEALTHY
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
40 mg single, oral
Recommended
Dose: 40 mg
Route: oral
Route: single
Dose: 40 mg
Sources:
healthy, 22.5 ± 3.9
Health Status: healthy
Age Group: 22.5 ± 3.9
Sex: M
Sources:
40 mg 1 times / day multiple, oral
Recommended
Dose: 40 mg, 1 times / day
Route: oral
Route: multiple
Dose: 40 mg, 1 times / day
Sources:
unhealthy, 41
Health Status: unhealthy
Age Group: 41
Sex: M+F
Sources:
20 mg 1 times / day multiple, oral
Recommended
Dose: 20 mg, 1 times / day
Route: oral
Route: multiple
Dose: 20 mg, 1 times / day
Sources:
unhealthy, 45.5
Health Status: unhealthy
Age Group: 45.5
Sex: M+F
Sources:
PubMed

PubMed

TitleDatePubMed
Rabeprazole: an update of its use in acid-related disorders.
2001
Relative efficacies of gastric proton-pump inhibitors on a milligram basis: desired and undesired SH reactions. Impact of chirality.
2001
Efficacy of Helicobacter pylori eradication therapies: a single centre observational study.
2001
Effects of pirenzepine, omeprazole, lansoprazole, and rabeprazole on human neutrophil functions.
2001 Apr
Helicobacter pylori eradication: do we have another ace up our sleeve?
2001 Dec
Effects of CYP2C19 genotypic differences in the metabolism of omeprazole and rabeprazole on intragastric pH.
2001 Dec
Duodenal mucosa-associated lymphoid tissue lymphoma treated by eradication of Helicobacter pylori: report of 2 cases including EUS findings.
2001 Dec
The effect of oral administration of Lactobacillus GG on antibiotic-associated gastrointestinal side-effects during Helicobacter pylori eradication therapy.
2001 Feb
Healing and relapse rates in gastroesophageal reflux disease treated with the newer proton-pump inhibitors lansoprazole, rabeprazole, and pantoprazole compared with omeprazole, ranitidine, and placebo: evidence from randomized clinical trials.
2001 Jul
Cost-effectiveness of proton-pump inhibitors for maintenance therapy of erosive reflux esophagitis.
2001 Jul 15
Acute fulminant hepatitis after treatment with rabeprazole and terbinafine.
2001 Jul 9
Training in the step-down inhibitory avoidance task time-dependently increases cAMP-dependent protein kinase activity in the entorhinal cortex.
2001 Jun
Inhibitory action of a novel proton pump inhibitor, rabeprazole, and its thioether derivative against the growth and motility of clarithromycin-resistant Helicobacter pylori.
2001 Jun
[Safety profile of pariet clinical use (a literature review)].
2001 May
Effects of CYP2C19 gene polymorphism on cure rates for Helicobacter pylori infection by triple therapy with proton pump inhibitor (omeprazole or rabeprazole), amoxycillin and clarithromycin in Japan.
2001 Nov
Efficacy of triple therapy with rabeprazole for Helicobacter pylori infection and CYP2C19 genetic polymorphism.
2001 Sep
[Pariet in eradication therapy plans].
2002
[Seven-day antihelicobacter therapy of duodenal ulcer associated with Helicobacter pylori and prospects for treating patients].
2002
[Effectiveness of pariet (rabeprazole) in the treatment of gastroesophageal reflux disease (at the reflux-esophagitis stage)].
2002
[Regeneration of the esophagus epitheliocytes. Evaluation of pariet efficacy in the treatment of patients with reflux esophagitis].
2002
[Inhibitors of proton pump in the treatment of non-ulcer functional dyspepsia of the reflux-like type].
2002
The effects of rabeprazole on parietal cells and enterochromaffin-like cells in rats: a comparison with omeprazole.
2002
[Regeneration of the gastric epitheliocytes during treatment of duodenal ulcer with pariet].
2002 Apr
Treatment and management of Helicobacter pylori infection.
2002 Dec
[Proton pump inhibitors: Rabeprazole].
2002 Feb
[Continuation of acid suppression therapy after H. pylori eradication].
2002 Feb
[High dose dual PPI/AMPC therapy for the treatment of Helicobacter pylori infection after failure of usual standard triple PPI/AMPC/CAM therapy: CYP2C19 polymorphism].
2002 Feb
[Proton pump inhibitor-based quadruple therapy regimen for Helicobacter pylori infection].
2002 Feb
[Dual therapy for Helicobacter pylori resistance to anti microbial agents].
2002 Feb
Treatment with a proton pump inhibitor promotes corpus gastritis in patients with Helicobacter pylori-infected antrum-predominant gastritis.
2002 Jan
Gateways to clinical trials.
2002 Jan-Feb
[Evaluation of efficacy, safety and tolerability rabeprazole in treatment of acid-peptic diseases ].
2002 Jan-Mar
Rabeprazole.
2002 Jan-Mar
Impact of proton pump inhibitor utilization patterns on gastroesophageal reflux disease-related costs.
2002 Jul
Measuring symptom distress and health-related quality of life in clinical trials of gastroesophageal reflux disease treatment: further validation of the Gastroesophageal Reflux Disease Symptom Assessment Scale (GSAS).
2002 Jul
Randomized open trial for comparison of proton pump inhibitors in triple therapy for Helicobacter pylori infection in relation to CYP2C19 genotype.
2002 Jul
The efficacy of lafutidine in improving preoperative gastric fluid property: a comparison with ranitidine and rabeprazole.
2002 Jul
Proton pump inhibitors: an update.
2002 Jul 15
Polymorphism of CYP2C19 and gastric emptying in patients with proton pump inhibitor-resistant gastric ulcers.
2002 Jul-Aug
Rabeprazole in nonerosive gastroesophageal reflux disease: a randomized placebo-controlled trial.
2002 Jun
Single vs. double dose of a proton pump inhibitor in triple therapy for Helicobacter pylori eradication: a meta-analysis.
2002 Jun
Onset of symptom relief with rabeprazole: a community-based, open-label assessment of patients with erosive oesophagitis.
2002 Mar
Effect of different probiotic preparations on anti-helicobacter pylori therapy-related side effects: a parallel group, triple blind, placebo-controlled study.
2002 Nov
Effects of rabeprazole, lansoprazole and omeprazole on intragastric pH in CYP2C19 extensive metabolizers.
2002 Oct
Rabeprazole: pharmacokinetics and pharmacokinetic drug interactions.
2002 Sep
Patents

Sample Use Guides

Erosive or Ulcerative Gastroesophageal Reflux Disease: 20 mg delayed-release tablet to be taken once daily for four to eight weeks.
Route of Administration: Oral
The MICs of rabeprazole sodium (RPZ) against 133 clinical Helicobacter pylori strains revealed a higher degree of activity. The 133 H. pylori strains tested were recent clinical isolates from different patients with chronic gastritis and gastric and/or duodenal ulcer. The final concentrations prepared in the wells of the microplates were from 0.031 to 64 μg/ml for RPZ.
Substance Class Chemical
Created
by admin
on Fri Jun 25 21:08:47 UTC 2021
Edited
by admin
on Fri Jun 25 21:08:47 UTC 2021
Record UNII
3L36P16U4R
Record Status Validated (UNII)
Record Version
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Name Type Language
RABEPRAZOLE SODIUM
MART.   ORANGE BOOK   USAN   USP-RS   WHO-DD  
USAN  
Official Name English
ACIPHEX
Brand Name English
E-3810 SODIUM
Code English
SODIUM RABEPRAZOLE
JAN  
Common Name English
RABEPRAZOLE SODIUM [ORANGE BOOK]
Common Name English
RABEPRAZOLE SODIUM [JAN]
Common Name English
LY307640 SODIUM
Code English
LY-307640 SODIUM
Code English
NSC-759270
Code English
RABEPRAZOLE NA [VANDF]
Common Name English
RABEPRAZOLE SODIUM [USP MONOGRAPH]
Common Name English
RABEPRAZOLE SODIUM [USAN]
Common Name English
IDIAZOLE
Brand Name English
RABEPRAZOLE SODIUM [EP MONOGRAPH]
Common Name English
2-(((4-(3-METHOXYPROPOXY)-3-METHYL-2-PYRIDYL)METHYL)SULFINYL)BENZIMIDAZOLE SODIUM SALT
Common Name English
RABEPRAZOLE NA
VANDF  
Common Name English
RABEPRAZOLE SODIUM SALT
MI  
Common Name English
RABEPRAZOLE SODIUM [MART.]
Common Name English
PARIET
Brand Name English
RABEPRAZOLE SODIUM [WHO-DD]
Common Name English
RABEPRAZOLE SODIUM [USP-RS]
Common Name English
RABEPRAZOLE SODIUM SALT [MI]
Common Name English
1H-BENZIMIDAZOLE, 2-(((4-(3-METHOXYPROPOXY)-3-METHYL-2-PYRIDINYL)METHYL)SULFINYL)-, SODIUM SALT
Common Name English
Code System Code Type Description
ChEMBL
CHEMBL1219
Created by admin on Fri Jun 25 21:08:47 UTC 2021 , Edited by admin on Fri Jun 25 21:08:47 UTC 2021
PRIMARY
MERCK INDEX
M9476
Created by admin on Fri Jun 25 21:08:47 UTC 2021 , Edited by admin on Fri Jun 25 21:08:47 UTC 2021
PRIMARY Merck Index
EVMPD
SUB04192MIG
Created by admin on Fri Jun 25 21:08:47 UTC 2021 , Edited by admin on Fri Jun 25 21:08:47 UTC 2021
PRIMARY
FDA UNII
3L36P16U4R
Created by admin on Fri Jun 25 21:08:47 UTC 2021 , Edited by admin on Fri Jun 25 21:08:47 UTC 2021
PRIMARY
PUBCHEM
14720269
Created by admin on Fri Jun 25 21:08:47 UTC 2021 , Edited by admin on Fri Jun 25 21:08:47 UTC 2021
PRIMARY
RXCUI
226868
Created by admin on Fri Jun 25 21:08:47 UTC 2021 , Edited by admin on Fri Jun 25 21:08:47 UTC 2021
PRIMARY RxNorm
DRUG BANK
DBSALT000552
Created by admin on Fri Jun 25 21:08:47 UTC 2021 , Edited by admin on Fri Jun 25 21:08:47 UTC 2021
PRIMARY
EPA CompTox
117976-90-6
Created by admin on Fri Jun 25 21:08:47 UTC 2021 , Edited by admin on Fri Jun 25 21:08:47 UTC 2021
PRIMARY
NCI_THESAURUS
C80692
Created by admin on Fri Jun 25 21:08:47 UTC 2021 , Edited by admin on Fri Jun 25 21:08:47 UTC 2021
PRIMARY
USP_CATALOG
1598019
Created by admin on Fri Jun 25 21:08:47 UTC 2021 , Edited by admin on Fri Jun 25 21:08:47 UTC 2021
PRIMARY USP-RS
CAS
117976-90-6
Created by admin on Fri Jun 25 21:08:47 UTC 2021 , Edited by admin on Fri Jun 25 21:08:47 UTC 2021
PRIMARY
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TARGET -> INHIBITOR
PARENT -> SALT/SOLVATE
METABOLIC ENZYME -> SUBSTRATE
METABOLIC ENZYME -> SUBSTRATE
TARGET -> INHIBITOR
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IMPURITY -> PARENT
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IMPURITY -> PARENT
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IMPURITY -> PARENT
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EP
IMPURITY -> PARENT
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IMPURITY -> PARENT
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IMPURITY -> PARENT
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IMPURITY -> PARENT
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IMPURITY -> PARENT
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IMPURITY -> PARENT
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IMPURITY -> PARENT
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IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
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IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
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IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
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ACTIVE MOIETY