Details
Stereochemistry | RACEMIC |
Molecular Formula | C15H23N3O4S |
Molecular Weight | 341.426 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CCN1CCCC1CNC(=O)C2=C(OC)C=CC(=C2)S(N)(=O)=O
InChI
InChIKey=BGRJTUBHPOOWDU-UHFFFAOYSA-N
InChI=1S/C15H23N3O4S/c1-3-18-8-4-5-11(18)10-17-15(19)13-9-12(23(16,20)21)6-7-14(13)22-2/h6-7,9,11H,3-5,8,10H2,1-2H3,(H,17,19)(H2,16,20,21)
Molecular Formula | C15H23N3O4S |
Molecular Weight | 341.426 |
Charge | 0 |
Count |
|
Stereochemistry | RACEMIC |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Optical Activity | ( + / - ) |
DescriptionSources: https://www.drugbank.ca/drugs/DB00391Curator's Comment: description was created based on several sources, including:
https://www.ncbi.nlm.nih.gov/pubmed/6628519
Sources: https://www.drugbank.ca/drugs/DB00391
Curator's Comment: description was created based on several sources, including:
https://www.ncbi.nlm.nih.gov/pubmed/6628519
Sulpiride is an atypical antipsychotic drug (although some texts have referred to it as a typical antipsychotic) of the benzamide class used mainly in the treatment of psychosis associated with schizophrenia and major depressive disorder, and sometimes used in low dosage to treat anxiety and mild depression. Sulpiride is commonly used in Europe, Russia and Japan. Sulpiride is a selective antagonist at dopamine D2 and D3 receptors. This action dominates in doses exceeding 600 mg daily. In doses of 600 to 1,600 mg sulpiride shows mild sedating and antipsychotic activity. Its antipsychotic potency compared to chlorpromazine is only 0.2 (1/5). In low doses (in particular 50 to 200 mg daily) its prominent feature is antagonism of presynaptic inhibitory dopamine receptors accounting for some antidepressant activity and a stimulating effect. Therefore, it is in these doses used as a second line antidepressant. Racemic and L-sulpiride significantly decreased stimulated serum gastrin concentration, but they did not affect fasting serum gastrin or basal and stimulated gastric acidity. D-sulpiride significantly decreased gastric acid secretion, without affecting serum gastrin levels.
CNS Activity
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL217 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21495689 |
10.28 nM [IC50] | ||
Target ID: CHEMBL234 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21495689 |
66.22 nM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Eglonyl Approved UseIndications. Acute and chronic psychosis (confusion, delirium, confusion, agrammatism, abulia), schizophrenia; neurotic state, accompanied by lethargy; psychosomatic symptoms (especially for stomach ulcers and duodenal ulcers and hemorrhagic rektokolite). |
|||
Primary | Eglonyl Approved UseIndications. Acute and chronic psychosis (confusion, delirium, confusion, agrammatism, abulia), schizophrenia; neurotic state, accompanied by lethargy; psychosomatic symptoms (especially for stomach ulcers and duodenal ulcers and hemorrhagic rektokolite). |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
89.8 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23585286/ |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: |
SULPIRIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
9.03 mg × h/L/(mg dose/kg) EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1815069/ |
100 mg single, intravenous dose: 100 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
SULPIRIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
7.81 mg × h/L/(mg dose/kg) EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1815069/ |
100 mg single, intramuscular dose: 100 mg route of administration: Intramuscular experiment type: SINGLE co-administered: |
SULPIRIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
1402.5 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23585286/ |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: |
SULPIRIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
6.47 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1815069/ |
100 mg single, intravenous dose: 100 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
SULPIRIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
7.17 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1815069/ |
100 mg single, intramuscular dose: 100 mg route of administration: Intramuscular experiment type: SINGLE co-administered: |
SULPIRIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
9 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23585286/ |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: |
SULPIRIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
Doses
Dose | Population | Adverse events |
---|---|---|
3200 mg 2 times / day multiple, oral Highest studied dose Dose: 3200 mg, 2 times / day Route: oral Route: multiple Dose: 3200 mg, 2 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
Other AEs: Dry mouth, Constipation... Other AEs: Dry mouth (25%) Sources: Constipation (19%) Palpitation (6%) Dizziness (12.5%) Fainting (6%) Increased sweating (6%) Parkinsonism (12.5%) Akathisia (44%) Hyperkinesia (19%) Tardive dyskinesia (6%) Drowsiness (12.5%) Itching (19%) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Dizziness | 12.5% | 3200 mg 2 times / day multiple, oral Highest studied dose Dose: 3200 mg, 2 times / day Route: oral Route: multiple Dose: 3200 mg, 2 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
Drowsiness | 12.5% | 3200 mg 2 times / day multiple, oral Highest studied dose Dose: 3200 mg, 2 times / day Route: oral Route: multiple Dose: 3200 mg, 2 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
Parkinsonism | 12.5% | 3200 mg 2 times / day multiple, oral Highest studied dose Dose: 3200 mg, 2 times / day Route: oral Route: multiple Dose: 3200 mg, 2 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
Constipation | 19% | 3200 mg 2 times / day multiple, oral Highest studied dose Dose: 3200 mg, 2 times / day Route: oral Route: multiple Dose: 3200 mg, 2 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
Hyperkinesia | 19% | 3200 mg 2 times / day multiple, oral Highest studied dose Dose: 3200 mg, 2 times / day Route: oral Route: multiple Dose: 3200 mg, 2 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
Itching | 19% | 3200 mg 2 times / day multiple, oral Highest studied dose Dose: 3200 mg, 2 times / day Route: oral Route: multiple Dose: 3200 mg, 2 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
Dry mouth | 25% | 3200 mg 2 times / day multiple, oral Highest studied dose Dose: 3200 mg, 2 times / day Route: oral Route: multiple Dose: 3200 mg, 2 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
Akathisia | 44% | 3200 mg 2 times / day multiple, oral Highest studied dose Dose: 3200 mg, 2 times / day Route: oral Route: multiple Dose: 3200 mg, 2 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
Fainting | 6% | 3200 mg 2 times / day multiple, oral Highest studied dose Dose: 3200 mg, 2 times / day Route: oral Route: multiple Dose: 3200 mg, 2 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
Increased sweating | 6% | 3200 mg 2 times / day multiple, oral Highest studied dose Dose: 3200 mg, 2 times / day Route: oral Route: multiple Dose: 3200 mg, 2 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
Palpitation | 6% | 3200 mg 2 times / day multiple, oral Highest studied dose Dose: 3200 mg, 2 times / day Route: oral Route: multiple Dose: 3200 mg, 2 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
Tardive dyskinesia | 6% | 3200 mg 2 times / day multiple, oral Highest studied dose Dose: 3200 mg, 2 times / day Route: oral Route: multiple Dose: 3200 mg, 2 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
no [IC50 >10 uM] | ||||
no [IC50 >10 uM] | ||||
no [IC50 >10 uM] | ||||
no [IC50 >10 uM] | ||||
no [IC50 >10 uM] | ||||
no [IC50 >10 uM] | ||||
no [IC50 >10 uM] | ||||
no [IC50 >1000 uM] | ||||
Page: 687.0 |
no | |||
yes [Inhibition 10 uM] | ||||
yes [Inhibition 10 uM] |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
no | ||||
no | ||||
yes [Km 166 uM] | ||||
yes [Km 187.2 uM] | ||||
yes [Km 259.7 uM] | ||||
yes | ||||
yes | ||||
yes | ||||
yes |
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
PubMed
Title | Date | PubMed |
---|---|---|
The role of the globus pallidus D2 subfamily of dopamine receptors in pallidal immediate early gene expression. | 2001 |
|
Short-term modulation of prolactin secretion by melatonin in anestrous ewes following dopamine- and opiate receptor blockade. | 2001 |
|
Consensus on the Practical Use of Amisulpride, an Atypical Antipsychotic, in the Treatment of Schizophrenia. | 2001 |
|
[Initial experiences with amisulpride, an in Germany novel, atypical neuroleptic drug in treatment of adolescents with psychiatric disorders]. | 2001 Aug |
|
Atypical neuroleptic drugs downregulate dopamine sensitivity in rat cortical and striatal astrocytes. | 2001 Aug |
|
A method to evaluate the diffusion rate of drugs from a microdialysis probe through brain tissue. | 2001 Aug 15 |
|
Dopamine D1 and NMDA receptors mediate potentiation of basolateral amygdala-evoked firing of nucleus accumbens neurons. | 2001 Aug 15 |
|
Amphetamine distorts stimulation-dependent dopamine overflow: effects on D2 autoreceptors, transporters, and synaptic vesicle stores. | 2001 Aug 15 |
|
Effects of kappa-opioid receptor agonists on long-term cocaine use and dopamine neurotransmission. | 2001 Aug 24 |
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A dopaminergic mechanism is involved in the 'anxiogenic-like' response induced by chronic amphetamine treatment: a behavioral and neurochemical study. | 2001 Aug 3 |
|
Intra-supraoptic nucleus sulpiride improves anorexia in tumor-bearing rats. | 2001 Aug 8 |
|
Hypothalamic dopaminergic receptor expressions in anorexia of tumor-bearing rats. | 2001 Dec |
|
[Participation of the dopaminergic brain system in effects of glucocorticoid hormones]. | 2001 Jul |
|
D2-like dopamine receptor activation excites rat dorsal raphe 5-HT neurons in vitro. | 2001 Jul |
|
Dopamine D2 receptor mediated presynaptic inhibition of striatopallidal GABA(A) IPSCs in vitro. | 2001 Jul |
|
A single blind comparison of amisulpride, fluoxetine and clomipramine in the treatment of restricting anorectics. | 2001 Jul |
|
Adenosine A2A agonist CGS 21680 decreases the affinity of dopamine D2 receptors for dopamine in human striatum. | 2001 Jul 3 |
|
Sulpiride in the treatment of somatoform disorders: results of a European observational study to characterize the responder profile. | 2001 Jul-Aug |
|
[Anti-stress effect of nitric oxide]. | 2001 Jul-Aug |
|
[Pseudoneurotic schizophrenia: a case report]. | 2001 Jul-Aug |
|
Pharmacological characterization of the D1- and D2-like dopamine receptors from the brain of the leopard frog, Rana pipiens. | 2001 Jun |
|
Neuroendocrine responsivities of the pituitary dopamine system in male schizophrenic patients during treatment with clozapine, olanzapine, risperidone, sulpiride, or haloperidol. | 2001 Jun |
|
The role of medial prefrontal cortical dopamine in spontaneous flexibility in the rat. | 2001 Jun |
|
The prolactin response to sulpiride in major depression: the role of the D2 receptor in depression. | 2001 Jun |
|
Accumbens dopamine mechanisms in sucrose intake. | 2001 Jun 15 |
|
Dopamine D2-like receptors and amino acid-induced glomerular hyperfiltration in humans. | 2001 May |
|
Attenuation of morphine dependence and withdrawal in rats by venlafaxine, a serotonin and noradrenaline reuptake inhibitor. | 2001 May 25 |
|
Faster response on amisulpride 50 mg versus sertraline 50-100 mg in patients with dysthymia or double depression: a randomized, double-blind, parallel group study. | 2001 Nov |
|
Dopaminergic modulation of grooming behavior in virgin and pregnant rats. | 2001 Nov |
|
Involvement of serotonergic and dopaminergic mechanisms in hyperthermia induced by a serotonin-releasing drug, p-chloroamphetamine in mice. | 2001 Nov 2 |
|
Postnatal decrease of sodium current density in rat pituitary melanotropes following the onset of dopaminergic innervation. | 2001 Nov 27 |
|
Dopaminergic and cholinergic antagonism in a novel-object detection task with rats. | 2001 Nov 29 |
|
Development of a high-performance liquid chromatographic method for bioanalytical applications with sulpiride. | 2001 Nov 5 |
|
Prevalence of obesity in adolescent and young adult patients with and without schizophrenia and in relationship to antipsychotic medication. | 2001 Nov-Dec |
|
Catalepsy induced by a blockade of dopamine D1 or D2 receptors was reversed by a concomitant blockade of adenosine A(2A) receptors in the caudate-putamen of rats. | 2001 Oct |
|
Dopamine mediates striatal malonate toxicity via dopamine transporter-dependent generation of reactive oxygen species and D2 but not D1 receptor activation. | 2001 Oct |
|
The effects of dopamine and its antagonists on directional delay-period activity of prefrontal neurons in monkeys during an oculomotor delayed-response task. | 2001 Oct |
|
Characterization of the role of medial prefrontal cortex dopamine receptors in cocaine-induced locomotor activity. | 2001 Oct |
|
Inverse agonist actions of typical and atypical antipsychotic drugs at the human 5-hydroxytryptamine(2C) receptor. | 2001 Oct |
|
Changes in muscle tone are regulated by D1 and D2 dopamine receptors in the ventral striatum and D1 receptors in the substantia nigra. | 2001 Oct |
|
Novel Ca2+ dependence and time course of somatodendritic dopamine release: substantia nigra versus striatum. | 2001 Oct 1 |
|
Potentiation of opioid analgesia in dopamine2 receptor knock-out mice: evidence for a tonically active anti-opioid system. | 2001 Oct 1 |
|
Hypothalamic CRH mRNA levels are differentially modulated by repeated 'binge' cocaine with or without D(1) dopamine receptor blockade. | 2001 Oct 19 |
|
Detection of pharmacologically mediated changes in cerebral activity by functional magnetic resonance imaging: the effects of sulpiride in the brain of the anaesthetised rat. | 2001 Oct 19 |
|
Modulation of dopamine uptake in rat nucleus accumbens: effect of specific dopamine receptor antagonists and sigma ligands. | 2001 Oct 26 |
|
[Incompatibility of olanzapine and amisulpride in multisystemic myotonic myopathy]. | 2001 Sep |
|
Physostigmine as treatment for severe CNS anticholinergic toxicity. | 2001 Sep |
|
Dopamine D4 receptor activation inhibits presynaptically glutamatergic neurotransmission in the rat supraoptic nucleus. | 2001 Sep |
|
Differential time-course profiles of dopamine release and uptake changes induced by three dopamine uptake inhibitors. | 2001 Sep 15 |
|
Repeated treatment with imipramine, fluvoxamine and tranylcypromine decreases the number of escape failures by activating dopaminergic systems in a rat learned helplessness test. | 2001 Sep 7 |
Sample Use Guides
400mg twice daily the doctor may reduce the dose to 200mg twice daily or increase it to a maximum of 1200mg twice daily
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/21495689
CHO-K1 D3R cells (DiscoveRx) were seeded at a density of 5000 cells/well in 384-well black, clear-bottom plates. Following 24 h of incubation, the cells were treated with multiple concentrations of the Sulpiride (0-10 μM) in Hanks’ balanced buffer solution containing 2% DMSO. Following a 10 min preincubation, the cells were next treated with an EC95 dose of dopamine (100 nM) and then incubated at 37 C for 90 min. DiscoveRx reagent (2.5) was then added to cells followed by a 60 min incubation at room temperature. Luminescence was measured on a Hamamatsu FDSS μ-cell reader.
Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 19:29:54 GMT 2025
by
admin
on
Mon Mar 31 19:29:54 GMT 2025
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Record UNII |
7MNE9M8287
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Record Status |
Validated (UNII)
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Record Version |
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Classification Tree | Code System | Code | ||
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WHO-ATC |
N05AL01
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NCI_THESAURUS |
C66883
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WHO-VATC |
QN05AL01
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Code System | Code | Type | Description | ||
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DTXSID1042574
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PRIMARY | |||
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7MNE9M8287
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PRIMARY | |||
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C87713
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PRIMARY | |||
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DB00391
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7MNE9M8287
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CHEMBL26
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95204-38-9
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15676-16-1
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PRIMARY | |||
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5355
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SUB10758MIG
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757850
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10239
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239-753-7
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5501
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D013469
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2359
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Sulpiride
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SULPIRIDE
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32168
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m10389
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PRIMARY | Merck Index | ||
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100000091056
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23672-06-2
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SUPERSEDED | |||
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2537
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51061-74-6
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SALT/SOLVATE -> PARENT | |||
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LABELED -> NON-LABELED |
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
Iron (2.4.9): maximum 10 ppm.
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (TLC)
EP
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IMPURITY -> PARENT |
Chlorides (2.4.4): maximum 100 ppm.
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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ACTIVE MOIETY |