Details
Stereochemistry | ACHIRAL |
Molecular Formula | C19H21N5O2 |
Molecular Weight | 351.4031 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CN1CCN(CC1)CC(=O)N2c3ccccc3C(=Nc4cccnc42)O
InChI
InChIKey=RMHMFHUVIITRHF-UHFFFAOYSA-N
InChI=1S/C19H21N5O2/c1-22-9-11-23(12-10-22)13-17(25)24-16-7-3-2-5-14(16)19(26)21-15-6-4-8-20-18(15)24/h2-8H,9-13H2,1H3,(H,21,26)
Molecular Formula | C19H21N5O2 |
Molecular Weight | 351.4031 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Pirenzepine is a M1 muscarinic receptor antagonist, which is prescribed for the treatment of gastric and duodenal ulcer in Europe. The drug preferentially acts on the gastric mucosa to inhibit secretion of both gastric acid and pepsin. Experiment with healthy volunteers demonstrated that pirenzepine passes the blood-brain barrier, but only to a small extent.
CNS Activity
Sources: https://www.ncbi.nlm.nih.gov/pubmed/6941375
Curator's Comment:: Pirenzepine passes the blood-brain barrier, but only to a small extent.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: P11229 Gene ID: 1128.0 Gene Symbol: CHRM1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/21918262 |
192.0 nM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | GASTROZEPIN Approved UseGASTROZEPIN is used for a duodenal ulcer and a benign stomach ulcer. |
|||
Primary | GASTROZEPIN Approved UseGASTROZEPIN is used for a duodenal ulcer and a benign stomach ulcer. |
PubMed
Title | Date | PubMed |
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M3 muscarinic receptor activation of a delayed rectifier potassium current in canine atrial myocytes. | 1999 |
|
A double-blind placebo-controlled case study of the use of donepezil to improve cognition in a schizoaffective disorder patient: functional MRI correlates. | 2001 |
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Pharmacology, distribution and development of muscarinic acetylcholine receptor subtypes in the optic tectum of Rana pipiens. | 2001 |
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First experiences in combination therapy using olanzapine with SSRIs (citalopram, paroxetine) in delusional depression. | 2001 |
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Weight change and atypical antipsychotic treatment in patients with schizophrenia. | 2001 |
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Cardiac safety parameters of olanzapine: comparison with other atypical and typical antipsychotics. | 2001 |
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Evidence for the effectiveness of olanzapine among patients nonresponsive and/or intolerant to risperidone. | 2001 |
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An efficacy analysis of olanzapine treatment data in schizophrenia patients with catatonic signs and symptoms. | 2001 |
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Rapid tranquilization with olanzapine in acute psychosis: a case series. | 2001 |
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Atypical antipsychotics: new directions and new challenges in the treatment of schizophrenia. | 2001 |
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Manic symptoms induced by olanzapine. | 2001 Apr |
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Comment: olanzapine-induced acute pancreatitis. | 2001 Apr |
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Olanzapine overdose. | 2001 Apr |
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Olanzapine-associated priapism. | 2001 Apr |
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Acetylcholine increases intracellular Ca2+ in the rat pituitary folliculostellate cells in primary culture. | 2001 Apr |
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Effects of brucine, a plant alkaloid, on M(1) muscarinic receptors and alpha(1)-adrenoceptors in the rabbit vas deferens preparation. | 2001 Apr |
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Long-term olanzapine treatment: weight change and weight-related health factors in schizophrenia. | 2001 Feb |
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Effects of newer atypical antipsychotics on autonomic neurocardiac function: a comparison between amisulpride, olanzapine, sertindole, and clozapine. | 2001 Feb |
|
Olanzapine plasma concentrations and clinical response: acute phase results of the North American Olanzapine Trial. | 2001 Feb |
|
The economic consequences of a drug-drug interaction. | 2001 Feb |
|
Repeated episodes of hypothermia in a subject treated with haloperidol, levomepromazine, olanzapine, and thioridazine. | 2001 Feb |
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Atypical antipsychotics and cardiovascular risk in schizophrenic patients. | 2001 Feb |
|
Pharmacological characterization of muscarinic receptors in dog isolated ciliary and urinary bladder smooth muscle. | 2001 Feb |
|
Traditional and new antipsychotic drugs differentially alter neurotransmission markers in basal ganglia-thalamocortical neural pathways. | 2001 Feb |
|
Modulation by muscarinic antagonists of the response to carbon dioxide challenge in panic disorder. | 2001 Feb |
|
Rehospitalization rates of chronically ill schizophrenic patients discharged on a regimen of risperidone, olanzapine, or conventional antipsychotics. | 2001 Feb |
|
Muscarinic receptor subtypes and calcium signaling in Fischer rat thyroid cells. | 2001 Feb 1 |
|
Characterisation of the prejunctional inhibitory muscarinic receptor on cholinergic nerves in the rat urinary bladder. | 2001 Feb 16 |
|
A novel augmentation strategy for treating resistant major depression. | 2001 Jan |
|
Lowered seizure threshold on olanzapine. | 2001 Jan |
|
Consistency of atypical antipsychotic superiority to placebo in recent clinical trials. | 2001 Jan 1 |
|
Double-blind comparison of olanzapine versus clozapine in schizophrenic patients clinically eligible for treatment with clozapine. | 2001 Jan 1 |
|
Dopamine transporter density in young patients with schizophrenia assessed with [123]FP-CIT SPECT. | 2001 Jan 15 |
|
[Olanzapine and pregnancy]. | 2001 Jan 21 |
|
Interleukin-2 and interleukin-4 increase the survival of retinal ganglion cells in culture. | 2001 Jan 22 |
|
[Subjective and objective evaluation of treating schizophrenia with classic or atypical drugs]. | 2001 Jan-Feb |
|
[Obsessive-compulsive disorders in adolescents with diagnosed schizophrenia]. | 2001 Jan-Feb |
|
Dementia with Lewy bodies in Down's syndrome. | 2001 Mar |
|
Effects of antimanic mood-stabilizing drugs on fetuses, neonates, and nursing infants. | 2001 Mar |
|
Olanzapine-lnduced hyperglycemic nonketonic coma. | 2001 Mar |
|
Autoantibodies against neonatal heart M1 muscarinic acetylcholine receptor in children with congenital heart block. | 2001 Mar |
|
5-HT(2A) and D(2) receptor blockade increases cortical DA release via 5-HT(1A) receptor activation: a possible mechanism of atypical antipsychotic-induced cortical dopamine release. | 2001 Mar |
|
Low blood glucose and olanzapine. | 2001 Mar |
|
Insulin and leptin levels in patients with schizophrenia or related psychoses--a comparison between different antipsychotic agents. | 2001 Mar 1 |
|
Quantitative determination of olanzapine in rat brain tissue by high-performance liquid chromatography with electrochemical detection. | 2001 Mar 5 |
|
Separation of olanzapine, carbamazepine and their main metabolites by capillary electrophoresis with pseudo-stationary phases. | 2001 Mar 5 |
|
The antinociceptive and sedative effects of carbachol and oxycodone administered into brainstem pontine reticular formation and spinal subarachnoid space in rats. | 2001 May |
|
Expression of multiple subtypes of muscarinic receptors and cellular distribution in the human heart. | 2001 May |
|
Long-term effects of olanzapine, risperidone, and quetiapine on dopamine receptor types in regions of rat brain: implications for antipsychotic drug treatment. | 2001 May |
|
Antibodies against human putamen in adolescents with anorexia nervosa. | 2001 May |
Patents
Sample Use Guides
Gastric and duodenal ulcers: 1 tablet (GASTROZEPIN 50 mg) 2 times daily (morning and evening). Severe and complicated gastric and duodenal ulcers: 1 tablet (GASTROZEPINE 50 mg) 3 times daily.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/1972408
Muscle strips from the canine gall-bladder were treated with pirenzepine (10(-9)-10(-5) M). Pirenzepine antagonized muscle contractions in response to acetylcholine (10(-9)-10(-2) M) and CCK-8 (10(-11)-10(-6) M) in a significant manner.
Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Jun 26 04:03:26 UTC 2021
by
admin
on
Sat Jun 26 04:03:26 UTC 2021
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Record UNII |
3G0285N20N
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Record Status |
Validated (UNII)
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Record Version |
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WHO-ATC |
A02BX03
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NCI_THESAURUS |
C29704
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WHO-VATC |
QA02BX03
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D010890
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28797-61-7
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2200
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DB00670
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4848
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M8874
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PIRENZEPINE
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28797-61-7
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328
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3G0285N20N
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CHEMBL9967
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C76002
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8352
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3476
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SUB09904MIG
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249-228-4
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Related Record | Type | Details | ||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT |
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ACTIVE MOIETY |