Clinical data | |
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Trade names | Pirazidol |
Routes of administration | Oral |
ATC code |
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Legal status | |
Legal status |
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Pharmacokinetic data | |
Bioavailability | 20–30% |
Protein binding | 95% |
Metabolism | hepatic |
Onset of action | 2 to 8 hours |
Elimination half-life | up to 8 days [1] |
Excretion | urine (50–70%), feces (25–45%) |
Identifiers | |
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CAS Number | |
PubChem CID | |
IUPHAR/BPS | |
DrugBank | |
ChemSpider | |
UNII | |
KEGG | |
ChEMBL | |
CompTox Dashboard ( EPA) | |
Chemical and physical data | |
Formula | C15H18N2 |
Molar mass | 226.323 g·mol−1 |
3D model ( JSmol) | |
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Pirlindole (Lifril, Pyrazidol) is mainly a reversible inhibitor of monoamine oxidase A (RIMA) and secondly a SNRI which was developed and is used in Russia as an antidepressant. [2] It is structurally and pharmacologically related to metralindole.
The Fischer indole synthesis between p-Tolylhydrazine Hydrochloride [637-60-5] (1) and 1,2-Cyclohexanedione [765-87-7] (2) gives 6-methyl-2,3,4,9-tetrahydrocarbazol-1-one [3449-48-7] (3). Imine formation with ethanolamine [141-43-5] (4) gives CID:2838578 (5). Halogenation with phosphorus oxychloride gives (6). [13] Intramolcular alkylation with the indole nitrogen resulted in Dehydropirlindole [75804-32-9] (7). Reduction of the imine with sodium borohydride completes the synthesis of pirlindole (8).
Clinical data | |
---|---|
Trade names | Pirazidol |
Routes of administration | Oral |
ATC code |
|
Legal status | |
Legal status |
|
Pharmacokinetic data | |
Bioavailability | 20–30% |
Protein binding | 95% |
Metabolism | hepatic |
Onset of action | 2 to 8 hours |
Elimination half-life | up to 8 days [1] |
Excretion | urine (50–70%), feces (25–45%) |
Identifiers | |
| |
CAS Number | |
PubChem CID | |
IUPHAR/BPS | |
DrugBank | |
ChemSpider | |
UNII | |
KEGG | |
ChEMBL | |
CompTox Dashboard ( EPA) | |
Chemical and physical data | |
Formula | C15H18N2 |
Molar mass | 226.323 g·mol−1 |
3D model ( JSmol) | |
|
Pirlindole (Lifril, Pyrazidol) is mainly a reversible inhibitor of monoamine oxidase A (RIMA) and secondly a SNRI which was developed and is used in Russia as an antidepressant. [2] It is structurally and pharmacologically related to metralindole.
The Fischer indole synthesis between p-Tolylhydrazine Hydrochloride [637-60-5] (1) and 1,2-Cyclohexanedione [765-87-7] (2) gives 6-methyl-2,3,4,9-tetrahydrocarbazol-1-one [3449-48-7] (3). Imine formation with ethanolamine [141-43-5] (4) gives CID:2838578 (5). Halogenation with phosphorus oxychloride gives (6). [13] Intramolcular alkylation with the indole nitrogen resulted in Dehydropirlindole [75804-32-9] (7). Reduction of the imine with sodium borohydride completes the synthesis of pirlindole (8).