Details
Stereochemistry | ABSOLUTE |
Molecular Formula | 2C17H18N3O3S.Mg |
Molecular Weight | 713.121 |
Optical Activity | ( - ) |
Defined Stereocenters | 2 / 2 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[Mg++].COC1=CC2=C([N-]C(=N2)[S@@+]([O-])CC3=NC=C(C)C(OC)=C3C)C=C1.COC4=CC5=C([N-]C(=N5)[S@@+]([O-])CC6=NC=C(C)C(OC)=C6C)C=C4
InChI
InChIKey=KWORUUGOSLYAGD-YPPDDXJESA-N
InChI=1S/2C17H18N3O3S.Mg/c2*1-10-8-18-15(11(2)16(10)23-4)9-24(21)17-19-13-6-5-12(22-3)7-14(13)20-17;/h2*5-8H,9H2,1-4H3;/q2*-1;+2/t2*24-;/m00./s1
Molecular Formula | C17H19N3O3S |
Molecular Weight | 345.416 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Molecular Formula | Mg |
Molecular Weight | 24.305 |
Charge | 2 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Esomeprazole strontium is a proton pump inhibitor. It suppresses gastric acid secretion by specific inhibition H+/K+ ATPase in the gastric parietal cell. The S- and R-isomers of omeprazole are protonated and converted in the acidic compartment of the parietal cell forming the active inhibitor, the achiral sulphenamide. By acting specifically on the proton pump, esomeprazole blocks the final step in acid production, thus reducing gastric acidity. The drug is indicated for the treatment of gastroesophageal reflux disease, reduction the risk of NSAID-associated gastric ulcer, eradication of H.pylori, and pathological hypersecretory conditions.
CNS Activity
Sources: https://www.ncbi.nlm.nih.gov/pubmed/11999751
Curator's Comment: Known to be CNS penetrant in mouse. Human data not available
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2095173 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10411559 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | NEXIUM 24HR Approved Usetreats frequent heartburn (occurs 2 or more days a week) Launch Date2014 |
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Primary | PRILOSEC Approved UsePRILOSEC is a proton pump inhibitor indicated for: treatment of duodenal ulcer in adults, treatment of gastric ulcer in adults. Treatment of Gastroesophageal Reflux Disease. Maintenance of healing of erosive esophagitis in pediatric patients and adults. Treatment of pathological hypersecretory conditions in adults. Launch Date2008 |
|||
Primary | PRILOSEC Approved UsePRILOSEC is a proton pump inhibitor indicated for: treatment of duodenal ulcer in adults, treatment of gastric ulcer in adults. Treatment of Gastroesophageal Reflux Disease. Maintenance of healing of erosive esophagitis in pediatric patients and adults. Treatment of pathological hypersecretory conditions in adults. Launch Date2008 |
|||
Primary | PRILOSEC Approved UsePRILOSEC is a proton pump inhibitor indicated for: treatment of duodenal ulcer in adults, treatment of gastric ulcer in adults. Treatment of Gastroesophageal Reflux Disease. Maintenance of healing of erosive esophagitis in pediatric patients and adults. Treatment of pathological hypersecretory conditions in adults. Launch Date1989 |
|||
Primary | PRILOSEC Approved UsePRILOSEC is a proton pump inhibitor indicated for: treatment of duodenal ulcer in adults, treatment of gastric ulcer in adults. Treatment of Gastroesophageal Reflux Disease. Maintenance of healing of erosive esophagitis in pediatric patients and adults. Treatment of pathological hypersecretory conditions in adults. Launch Date2008 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
668 ng/mL |
1 mg/kg single, oral dose: 1 mg/kg route of administration: Oral experiment type: SINGLE co-administered: |
OMEPRAZOLE plasma | Homo sapiens population: UNKNOWN age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
7.5 μM |
40 mg 1 times / day multiple, intravenous dose: 40 mg route of administration: Intravenous experiment type: MULTIPLE co-administered: |
ESOMEPRAZOLE plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1200 nM*h Clinical Trial https://clinicaltrials.gov/ct2/show/NCT01361217 |
20 mg single, oral dose: 20 mg route of administration: oral experiment type: single co-administered: |
OMEPRAZOLE plasma | Homo sapiens population: healthy age: adults sex: food status: |
|
1220 ng × h/mL |
1 mg/kg single, oral dose: 1 mg/kg route of administration: Oral experiment type: SINGLE co-administered: |
OMEPRAZOLE plasma | Homo sapiens population: UNKNOWN age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
1179 nM × h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/2350532 |
20 mg 1 times / day multiple, oral dose: 20 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
OMEPRAZOLE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
16.2 μM × h |
40 mg 1 times / day multiple, intravenous dose: 40 mg route of administration: Intravenous experiment type: MULTIPLE co-administered: |
ESOMEPRAZOLE plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
0.58 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/2350532 |
20 mg 1 times / day multiple, oral dose: 20 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
OMEPRAZOLE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
1.4 h |
40 mg 1 times / day multiple, intravenous dose: 40 mg route of administration: Intravenous experiment type: MULTIPLE co-administered: |
ESOMEPRAZOLE plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
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, 45.2 |
Other AEs: Nausea, Diarrhoea... |
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 Health Status: unhealthy Sources: |
Other AEs: Headache, Abdominal pain... Other AEs: Headache (6.9%) Sources: Abdominal pain (5.2%) Nausea (4%) Diarrhea (3.7%) Vomiting (3.2%) Flatulence (2.7%) Esophageal acid reflux (1.9%) Upper respiratory infection (1.9%) Constipation (1.5%) Dizziness (1.5%) Rash (1.5%) Asthenia (1.3%) Back pain (1.1%) Cough (1.1%) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Headache | 3% | 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, 45.2 |
Diarrhoea | 6% | 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, 45.2 |
Nausea | 7% | 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, 45.2 |
Back pain | 1.1% | 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 Health Status: unhealthy Sources: |
Cough | 1.1% | 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 Health Status: unhealthy Sources: |
Asthenia | 1.3% | 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 Health Status: unhealthy Sources: |
Constipation | 1.5% | 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 Health Status: unhealthy Sources: |
Dizziness | 1.5% | 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 Health Status: unhealthy Sources: |
Rash | 1.5% | 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 Health Status: unhealthy Sources: |
Esophageal acid reflux | 1.9% | 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 Health Status: unhealthy Sources: |
Upper respiratory infection | 1.9% | 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 Health Status: unhealthy Sources: |
Flatulence | 2.7% | 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 Health Status: unhealthy Sources: |
Vomiting | 3.2% | 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 Health Status: unhealthy Sources: |
Diarrhea | 3.7% | 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 Health Status: unhealthy Sources: |
Nausea | 4% | 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 Health Status: unhealthy Sources: |
Abdominal pain | 5.2% | 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 Health Status: unhealthy Sources: |
Headache | 6.9% | 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 Health Status: unhealthy Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
strong [IC50 3.7 uM] | yes (co-administration study) Comment: Esomeprazole administration resulted in a significant increase (1.67‐fold) in the AUC0–∞ of proguanil and a significant decrease (0.522‐fold) in that of cycloguanil |
|||
weak [IC50 >40 uM] | ||||
weak [IC50 >40 uM] | ||||
weak [IC50 >40 uM] | ||||
weak [IC50 >40 uM] | ||||
weak [IC50 >40 uM] | ||||
weak [IC50 >40 uM] | ||||
weak [Ki 150 uM] | weak (co-administration study) Comment: Omeprazole exerts a concentration-dependent inhibition of CYP1A2 activity in man. However, even after single oral doses up to 80 mg, this effect is weak and without clinical relevance |
|||
weak [Ki 367.5 uM] | ||||
weak [Ki 745.1 uM] | ||||
yes [IC50 1.2 uM] | likely (co-administration study) Comment: The frequency of delayed MTX elimination in patients administered esomeprazole was 71.4% Sources: https://pubmed.ncbi.nlm.nih.gov/28801980/ |
|||
yes [IC50 15.7 uM] | ||||
yes [IC50 17.6 uM] | ||||
yes [IC50 17.7 uM] | ||||
yes [IC50 22 uM] | ||||
yes [IC50 4.32 uM] | ||||
yes [IC50 6.7 uM] | ||||
yes [IC50 6.8 uM] | ||||
yes [IC50 84.3 uM] | unlikely (co-administration study) Comment: Coaministration with simvastatin acid unlikely results in DDIs Sources: https://pubmed.ncbi.nlm.nih.gov/25975815/ |
|||
yes [Ki 7.1 uM] | yes (co-administration study) Comment: Omeprazole increased Cmax and AUC of cilostazol by 18% and 26% respectively |
|||
Sources: https://pubmed.ncbi.nlm.nih.gov/10445394/ |
yes | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/12623754/ |
yes | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/12623754/ |
yes | |||
yes | ||||
yes | ||||
yes | ||||
yes | ||||
yes | ||||
Sources: https://pubmed.ncbi.nlm.nih.gov/12538803/ |
yes | yes (expression study) Comment: livers of patients treated with omeprazole showed higher MRP3 protein expression Sources: https://pubmed.ncbi.nlm.nih.gov/12538803/ |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
major | yes (co-administration study) Comment: When voriconazole was given with omeprazole to healthy subjects, it significantly increased the steady-state Cmax and AUC0-24 of omeprazole, an average of 2 times and 4 times, respectively |
|||
major | yes (co-administration study) Comment: Drugs known to induce CYP2C19 or CYP3A4 (such as rifampin) may lead to decreased omeprazole serum levels. In a cross-over study in 12 healthy male subjects, St John’s wort, an inducer of CYP3A4, decreased the systemic exposure of omeprazole in CYP2C19 poor metabolisers (Cmax and AUC decreased by 37.5% and 37.9%, respectively) and extensive metabolisers (Cmax and AUC decreased by 49.6% and 43.9%, respectively) |
|||
minor | ||||
minor | ||||
minor | ||||
no | ||||
yes | yes (co-administration study) Comment: Drugs which induce CYP2C19 or CYP3A4 (such as St. John’s Wort or rifampin) can substantially decrease esomeprazole concentrations |
|||
yes | yes (pharmacogenomic study) Comment: Drugs which induce CYP2C19 or CYP3A4 (such as St. John’s Wort or rifampin) can substantially decrease esomeprazole concentrations; The CYP2C19 isoenzyme exhibits polymorphism in the metabolism of esomeprazole, since some 3% of Caucasians and 15–20% of Asians lack CYP2C19 and are termed poor metabolizers. At steady state, the ratio of AUC in poor metabolizers to AUC in the rest of the population (normal metabolizers) is approximately 2 |
PubMed
Title | Date | PubMed |
---|---|---|
Pharmacokinetic study of esomeprazole in the elderly. | 2001 |
|
The risk of upper gastrointestinal complications associated with nonsteroidal anti-inflammatory drugs, glucocorticoids, acetaminophen, and combinations of these agents. | 2001 |
|
Effect of Lactobacillus GG supplementation on antibiotic-associated gastrointestinal side effects during Helicobacter pylori eradication therapy: a pilot study. | 2001 |
|
Which patients with ulcer- or reflux-like dyspepsia will respond favorably to omeprazole? | 2001 Apr |
|
Antireflux surgery in children suffering from reflux-associated respiratory disease? | 2001 Apr |
|
Pantoprazole and cyclosporine or tacrolimus. | 2001 Apr |
|
Maximal acid reflux control for Barrett's oesophagus: feasible and effective. | 2001 Apr |
|
Nitrofurantoin quadruple therapy for Helicobacter pylori infection: effect of metronidazole resistance. | 2001 Apr |
|
Effects of lansoprazole, clarithromycin and pH gradient on uptake of [14C]amoxycillin into rat gastric tissue. | 2001 Apr |
|
A new cause of Zollinger-Ellison syndrome: non-small cell lung cancer. | 2001 Apr |
|
Effect of the treatment of Helicobacter pylori infection on gastric emptying and its influence on the glycaemic control in type 1 diabetes mellitus. | 2001 Apr |
|
Differentiation between reinfection and recrudescence of helicobacter pylori strains using PCR-based restriction fragment length polymorphism analysis. | 2001 Feb |
|
Gastroesophageal reflux disease and Barrett's esophagus. | 2001 Feb |
|
[Suppressive effect of lansoprazole on anti-Candida activity of murine macrophages]. | 2001 Feb |
|
Re: Ammonia cannot explain the effect of H. pylori on omeprazole-induced acid suppression. | 2001 Feb |
|
A randomized, pharmacokinetic and pharmacodynamic, cross-over study of duodenal or jejunal administration compared to nasogastric administration of omeprazole suspension in patients at risk for stress ulcers. | 2001 Feb |
|
Increased acid and bile reflux in Barrett's esophagus compared to reflux esophagitis, and effect of proton pump inhibitor therapy. | 2001 Feb |
|
Comparison of the efficacy and safety of different formulations of omeprazole-based triple therapies in the treatment of Helicobacter pylori-positive peptic ulcer. | 2001 Feb |
|
Early stage gastric MALT lymphoma with high-grade component cured by Helicobacter pylori eradication. | 2001 Feb |
|
Antibiotic-resistance patterns of Helicobacter pylori in Croatia: cohort study. | 2001 Feb |
|
The prescribing of acid suppressants prior to the endoscopic diagnosis of Barrett's oesophagus and oesophagitis. | 2001 Feb |
|
[Prevalence and treatment of Helicobacter pylori in gastro-duodenal ulcers. An experience in Liege]. | 2001 Jan |
|
Upper gastrointestinal bleeding as a metastatic manifestation of breast cancer: a case report and review of the literature. | 2001 Jan |
|
Gastroesophageal reflux disease: extraesophageal manifestations and therapy. | 2001 Jan |
|
Management of GERD: medical versus surgical. | 2001 Jan |
|
Randomized study of two "rescue" therapies for Helicobacter pylori-infected patients after failure of standard triple therapies. | 2001 Jan |
|
Esomeprazole once daily for 6 months is effective therapy for maintaining healed erosive esophagitis and for controlling gastroesophageal reflux disease symptoms: a randomized, double-blind, placebo-controlled study of efficacy and safety. | 2001 Jan |
|
Changes in pulmonary hyperinflation and bronchial hyperresponsiveness following treatment with lansoprazole in children with cystic fibrosis. | 2001 Jan |
|
Hypergastrinemia promotes adenoma progression in the APC(Min-/+) mouse model of familial adenomatous polyposis. | 2001 Jan 15 |
|
Propylene glycol toxicosis in a llama. | 2001 Jan 15 |
|
Effect of polaprezinc on impaired healing of chronic gastric ulcers in adjuvant-induced arthritic rats--role of insulin-like growth factors (IGF)-1. | 2001 Jan-Feb |
|
The effect of culture results for Helicobacter pylori on the choice of treatment following failure of initial eradication. | 2001 Mar |
|
Pharmacodynamic modeling of lansoprazole using an indirect irreversible response model. | 2001 Mar |
|
Pharmacokinetic differences between lansoprazole enantiomers and contribution of cytochrome P450 isoforms to enantioselective metabolism of lansoprazole in dogs. | 2001 Mar |
|
Effect of genotypic differences in CYP2C19 on cure rates for Helicobacter pylori infection by triple therapy with a proton pump inhibitor, amoxicillin, and clarithromycin. | 2001 Mar |
|
Stereoselective pharmacokinetics of pantoprazole, a proton pump inhibitor, in extensive and poor metabolizers of S-mephenytoin. | 2001 Mar |
|
A case of gastric plasmacytoma associated with Helicobacter pylori infection: improvement of abnormal endoscopic and EUS findings after H. pylori eradication. | 2001 Mar |
|
Bioequivalence evaluation of lansoprazole 30-mg capsules (Lanfast and Lanzor) in healthy volunteers. | 2001 Mar |
|
Five-day proton pump inhibitor-based quadruple therapy regimen is more effective than 7-day triple therapy regimen for Helicobacter pylori infection. | 2001 Mar |
|
Clarithromycin vs. furazolidone in quadruple therapy regimens for the treatment of Helicobacter pylori in a population with a high metronidazole resistance rate. | 2001 Mar |
|
One-week ranitidine bismuth citrate-based triple therapy for the eradication of Helicobacter pylori in Hong Kong with high prevalence of metronidazole resistance. | 2001 Mar |
|
Esomeprazole 20 mg maintains symptom control in endoscopy-negative gastro-oesophageal reflux disease: a controlled trial of 'on-demand' therapy for 6 months. | 2001 Mar |
|
Predictive factors for regression of gastric MALT lymphoma after anti-Helicobacter pylori treatment. | 2001 Mar |
|
Improvement in atrophic gastritis and intestinal metaplasia in patients in whom Helicobacter pylori was eradicated. | 2001 Mar 6 |
|
[Heartburn. Only a harmless symptom?]. | 2001 Mar 8 |
|
Haloperidol-stomach lesions attenuation by pentadecapeptide BPC 157, omeprazole, bromocriptine, but not atropine, lansoprazole, pantoprazole, ranitidine, cimetidine and misoprostol in mice. | 2001 Mar 9 |
|
New OTC drugs and devices 2000: a selective review. | 2001 Mar-Apr |
|
Omeprazole therapy and salivary flow rate in duodenal ulcer patients. | 2001 Mar-Apr |
|
Microsatellite instability at D18S61 is associated with no regression of gastric mucosa-associated lymphoid tissue lymphoma after Helicobacter pylori eradication. | 2001 Mar-Apr |
|
c-myc gene mutation in gastric mucosa-associated lymphoid tissue (MALT) lymphoma and diffuse large B-cell lymphoma. | 2001 Mar-Apr |
Patents
Sample Use Guides
Active Duodenal Ulcer: 20 mg Once daily for 4 weeks. Some patients may require an addition 4 weeks.
Gastric Ulcer: oral dose is 40 mg once daily for 4-8 weeks.
Gastroesophageal Reflux Disease: The recommended adult oral dose for the treatment of patients with symptomatic GERD and no esophageal lesions is 20 mg daily for up to 4 weeks. The recommended adult oral dose for the treatment of patients with erosive esophagitis and accompanying symptoms due to GERD is 20 mg daily for 4 to 8 weeks.
Route of Administration:
Oral
Pretreatment of omeprazole (10-6 - 10-4M) dose-dependently inhibits neutrophil adherence and respiratory burst induced by H. pylori. These evidences imply that omeprazole may exhibit a beneficial effect on H. pylori-associated gastric mucosal damage caused by activated neutrophils.
Substance Class |
Chemical
Created
by
admin
on
Edited
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by
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on
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Record UNII |
925R0D7W1O
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Record Status |
Validated (UNII)
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Record Version |
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