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| Name | Promazine | |||||||||||||||||||||||||||||||||||||||
| Accession Number | DB00420 (APRD00358) | |||||||||||||||||||||||||||||||||||||||
| Type | small molecule | |||||||||||||||||||||||||||||||||||||||
| Groups | approved | |||||||||||||||||||||||||||||||||||||||
| Description | A phenothiazine with actions similar to chlorpromazine but with less antipsychotic activity. It is primarily used in short-term treatment of disturbed behavior and as an antiemetic. [PubChem] |
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| Structure |
Download: MOL | SDF | SMILES | InChI Display: 2D Structure | 3D Structure |
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| Brand mixtures | Not Available | |||||||||||||||||||||||||||||||||||||||
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| CAS number | 58-40-2 | |||||||||||||||||||||||||||||||||||||||
| Weight |
Average: 284.419 Monoisotopic: 284.13471934 |
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| Chemical Formula | C17H20N2S | |||||||||||||||||||||||||||||||||||||||
| InChI Key | InChIKey=ZGUGWUXLJSTTMA-UHFFFAOYSA-N | |||||||||||||||||||||||||||||||||||||||
| InChI |
InChI=1S/C17H20N2S/c1-18(2)12-7-13-19-14-8-3-5-10-16(14)20-17-11-6-4-9-15(17)19/h3-6,8-11H,7,12-13H2,1-2H3
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| IUPAC Name |
dimethyl[3-(10H-phenothiazin-10-yl)propyl]amine
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| SMILES |
CN(C)CCCN1C2=CC=CC=C2SC2=CC=CC=C12
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| Mass Spec | show (9.05 KB) | |||||||||||||||||||||||||||||||||||||||
| Taxonomy | ||||||||||||||||||||||||||||||||||||||||
| Kingdom | Organic | |||||||||||||||||||||||||||||||||||||||
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| Pharmacology | ||||||||||||||||||||||||||||||||||||||||
| Indication | Used as an adjunct for short term treatment of moderate and severe psychomotor agitation. Also used to treat agitation or restlessness in the elderly. | |||||||||||||||||||||||||||||||||||||||
| Pharmacodynamics | Promazine belongs to a group of medications known as the phenothiazine antipsychotics. It acts by blocking a variety of receptors in the brain, particularly dopamine receptors. Dopamine is involved in transmitting signals between brain cells. When there is an excess amount of dopamine in the brain it causes over-stimulation of dopamine receptors. These receptors normally act to modify behaviour and over-stimulation may result in psychotic illness. Promazine hydrochloride blocks these receptors and stops them becoming over-stimulated, thereby helping to control psychotic illness. Promazine has weak extrapyramidal and autonomic side effects which lead to its use in the elderly, for restless or psychotic patients. Its anti-psychotic effect is also weaker and it is not useful in general psychiatry. | |||||||||||||||||||||||||||||||||||||||
| Mechanism of action | Promazine is an antagonist at types 1, 2, and 4 dopamine receptors, 5-HT receptor types 2A and 2C, muscarinic receptors 1 through 5, alpha(1)-receptors, and histamine H1-receptors. Promazine's antipsychotic effect is due to antagonism at dopamine and serotonin type 2 receptors, with greater activity at serotonin 5-HT2 receptors than at dopamine type-2 receptors. This may explain the lack of extrapyramidal effects. Promazine does not appear to block dopamine within the tubero-infundibular tract, explaining the lower incidence of hyperprolactinemia than with typical antipsychotic agents or risperidone. Antagonism at muscarinic receptors, H1-receptors, and alpha(1)-receptors also occurs with promazine. | |||||||||||||||||||||||||||||||||||||||
| Absorption | Absorption may be erratic and peak plasma concentrations show large interindividual differences. | |||||||||||||||||||||||||||||||||||||||
| Volume of distribution | Not Available | |||||||||||||||||||||||||||||||||||||||
| Protein binding | 94% | |||||||||||||||||||||||||||||||||||||||
| Metabolism | Hepatic, primarily to N-desmethylpromazine and promazine sulfoxide. | |||||||||||||||||||||||||||||||||||||||
| Route of elimination | Not Available | |||||||||||||||||||||||||||||||||||||||
| Half life | Not Available | |||||||||||||||||||||||||||||||||||||||
| Clearance | Not Available | |||||||||||||||||||||||||||||||||||||||
| Toxicity | Side effects include: extrapyramidal symptoms, drowsiness, weight gain, dry mouth, constipation, endocrine effects (such as gynaecomastia and menstrual disturbance), sensitivity to sunlight and haemolytic anaemia. | |||||||||||||||||||||||||||||||||||||||
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| Pathways | Not Available | |||||||||||||||||||||||||||||||||||||||
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DrugBank does not sell nor buy drugs. Pricing information is supplied for informational
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| Patents | Not Available | |||||||||||||||||||||||||||||||||||||||
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| State | liquid | |||||||||||||||||||||||||||||||||||||||
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| Synthesis Reference | Not Available | |||||||||||||||||||||||||||||||||||||||
| General Reference | Not Available | |||||||||||||||||||||||||||||||||||||||
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| PDB Entries | Not Available | |||||||||||||||||||||||||||||||||||||||
| FDA label | Not Available | |||||||||||||||||||||||||||||||||||||||
| MSDS | show (75.4 KB) | |||||||||||||||||||||||||||||||||||||||
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| Food Interactions | Not Available | |||||||||||||||||||||||||||||||||||||||
| Targets |
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Pharmacological action: yes
Actions: antagonist This is one of the five types (D1 to D5) of receptors for dopamine. The activity of this receptor is mediated by G proteins which inhibit adenylyl cyclase Organism class: humanUniProt ID: P14416 ![]() Gene: DRD2 ![]() Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report ![]() References: 2. 5-hydroxytryptamine 2A receptor Pharmacological action: unknownActions: antagonist This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. This receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system. This receptor is involved in tracheal smooth muscle contraction, bronchoconstriction, and control of aldosterone production Organism class: humanUniProt ID: P28223 ![]() Gene: HTR2A ![]() Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report ![]() References:
3. 5-hydroxytryptamine 2C receptor Pharmacological action: unknownActions: antagonist This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. This receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system Organism class: humanUniProt ID: P28335 ![]() Gene: HTR2C ![]() Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report ![]() References:
Pharmacological action: unknown
Actions: antagonist This is one of the five types (D1 to D5) of receptors for dopamine. The activity of this receptor is mediated by G proteins which activate adenylyl cyclase Organism class: humanUniProt ID: P21728 ![]() Gene: DRD1 ![]() Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report ![]() References:
Pharmacological action: unknown
Actions: antagonist This is one of the five types (D1 to D5) of receptors for dopamine. The activity of this receptor is mediated by G proteins which inhibit adenylyl cyclase Organism class: humanUniProt ID: P21917 ![]() Gene: DRD4 ![]() Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report ![]() References: 6. Muscarinic acetylcholine receptor M4 Pharmacological action: unknownActions: antagonist The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is inhibition of adenylate cyclase Organism class: humanUniProt ID: P08173 ![]() Gene: CHRM4 ![]() Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report ![]() References: 7. Muscarinic acetylcholine receptor M2 Pharmacological action: unknownActions: antagonist The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is adenylate cyclase inhibition Organism class: humanUniProt ID: P08172 ![]() Gene: CHRM2 ![]() Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report ![]() References: 8. Muscarinic acetylcholine receptor M3 Pharmacological action: unknownActions: antagonist The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is Pi turnover Organism class: humanUniProt ID: P20309 ![]() Gene: CHRM3 ![]() Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report ![]() References: 9. Muscarinic acetylcholine receptor M1 Pharmacological action: unknownActions: antagonist The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is Pi turnover Organism class: humanUniProt ID: P11229 ![]() Gene: CHRM1 ![]() Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report ![]() References: 10. Alpha-1B adrenergic receptor Pharmacological action: unknownActions: antagonist This alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol- calcium second messenger system Organism class: humanUniProt ID: P35368 ![]() Gene: ADRA1B ![]() Protein Sequence: FASTA SNPs: SNPJam Report ![]() References: 11. Muscarinic acetylcholine receptor M5 Pharmacological action: unknownActions: antagonist The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is Pi turnover Organism class: humanUniProt ID: P08912 ![]() Gene: CHRM5 ![]() Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report ![]() References:
12. Alpha-1A adrenergic receptor Pharmacological action: unknownActions: antagonist This alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol- calcium second messenger system. Its effect is mediated by G(q) and G(11) proteins Organism class: humanUniProt ID: P35348 ![]() Gene: ADRA1A ![]() Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report ![]() References:
Pharmacological action: unknown
Actions: antagonist In peripheral tissues, the H1 subclass of histamine receptors mediates the contraction of smooth muscles, increase in capillary permeability due to contraction of terminal venules, and catecholamine release from adrenal medulla, as well as mediating neurotransmission in the central nervous system Organism class: humanUniProt ID: P35367 ![]() Gene: HRH1 ![]() Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report ![]() References:
14. Alpha-1D adrenergic receptor Pharmacological action: unknownActions: antagonist This alpha-adrenergic receptor mediates its effect through the influx of extracellular calcium Organism class: humanUniProt ID: P25100 ![]() Gene: ADRA1D ![]() Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report ![]() References: |
| Enzymes |
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Actions: substrate
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine UniProt ID: P33261![]() Gene: CYP2C19 ![]() Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report ![]() References:
Actions: substrate
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen UniProt ID: P05177![]() Gene: CYP1A2 Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report ![]() References:
Actions: substrate
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4- hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. The enzyme also hydroxylates etoposide UniProt ID: P08684![]() Gene: CYP3A4 Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report ![]() References:
Actions: substrate
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S- warfarin, diclofenac, phenytoin, tolbutamide and losartan UniProt ID: P11712![]() Gene: CYP2C9 Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report ![]() References:
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