Amisulpride
JFDA label: SOLIAN 100mg tablet
Mechanism of Action
Antagonist of Serotonin (5-HT) receptor — Serotonin (5-HT) receptor antagonist; Antagonist of Dopamine receptors; D2 & D3 — Dopamine receptors; D2 & D3 antagonist
| Target | Action | Gene / class |
|---|---|---|
| Dopamine receptors; D2 & D3 efficacy | ANTAGONIST | |
| Serotonin (5-HT) receptor efficacy | ANTAGONIST |
Indications
Approved
- Postoperative Nausea and Vomiting — post operative nausea and vomiting
- Psychotic Disorders — psychosis
Off-label
- Anxiety
- Bipolar Disorder
- Dementia
- Depressive Disorder
- Nausea
- Schizophrenia
Adverse Reactions
Cardiac disorders (6)
Uncommon Bradycardia
Rare Cardiac arrest · Cardiac disorder · Ventricular arrhythmia · Ventricular fibrillation · Ventricular tachycardia
Vascular disorders (5)
Very Common Hypotension
Common Hypertension · Orthostatic hypotension
Rare Deep vein thrombosis · Embolism venous
Nervous system disorders (8)
Very Common Akathisia · Dyskinesia · Dystonia · Tremor
Common Dizziness · Headache · Somnolence
Uncommon Tardive dyskinesia
Blood and lymphatic system disorders (3)
Rare Agranulocytosis · Leukopenia · Neutropenia
Immune system disorders (2)
Uncommon Hypersensitivity · Immune system disorder
Endocrine disorders (1)
Very Common Endocrine disorder
Metabolism and nutrition disorders (1)
Uncommon Hyperglycaemia
Gastrointestinal disorders (9)
Very Common Constipation · Dry mouth · Gastrointestinal disorder · Nausea · Vomiting
Common Abdominal pain · Diarrhoea · Dyspepsia · Gastrointestinal pain
Skin and subcutaneous tissue disorders (5)
Common Hyperhidrosis · Pruritus · Skin disorder
Rare Angioedema · Urticaria
Musculoskeletal and connective tissue disorders (2)
Very Common Muscle rigidity · Muscle spasms
Psychiatric disorders (5)
Very Common Agitation · Anxiety · Insomnia
Common Aggression · Depression
Reproductive system and breast disorders (5)
Common Amenorrhoea · Galactorrhoea · Menstrual disorder · Vaginal inflammation
Rare Pregnancy
Infections and infestations (1)
Common Vaginal infection
Investigations (2)
Very Common Weight increased
Common Weight decreased
General disorders and administration site conditions (16)
Very Common Extrapyramidal disorder · Hypokinesia · Oculogyric crisis · Salivary hypersecretion · Trismus
Common Asthenia · Fatigue · Nervousness · Suicide attempt · Tension
Uncommon Cardiovascular disorder
Rare Angiopathy · Drug withdrawal syndrome · Nervous system disorder · Sudden death · Torsade de pointes
Neoplasms benign, malignant and unspecified (incl cysts and polyps) (1)
Rare Neuroleptic malignant syndrome
Respiratory, thoracic and mediastinal disorders (1)
Rare Pulmonary embolism
Pregnancy & Lactation
Pregnancy
Lactation
Excretion of amisulpride into breastmilk is higher than with other pharmacologically similar drugs.
Chemistry & Properties
| Formula | C17H27N3O4S |
|---|---|
| Molecular weight | 369.49 g/mol |
| IUPAC name | 4-amino-N-[(1-ethylpyrrolidin-2-yl)methyl]-5-ethylsulfonyl-2-methoxybenzamide |
| CAS | 71675-85-9 |
| PubChem CID | 2159 |
| InChIKey | NTJOBXMMWNYJFB-UHFFFAOYSA-N |
| logP | 1.29 (XLogP 1.5) |
| Polar surface area | 101.73 Ų |
| H-bond acceptors / donors | 6 / 2 |
| Drug-likeness (QED) | 0.70 |
| Lipinski violations | 0 |
SMILES
CCN1CCCC1CNC(=O)c1cc(S(=O)(=O)CC)c(N)cc1OCBiology & Pharmacokinetics
Pharmacokinetics
| BBB penetrant | Yes |
|---|
Enzyme interactions
| Enzyme | Role | Detail |
|---|---|---|
| CYP2C19 | Substrate | — |
Receptor binding (top 20)
| Target | Action | Affinity |
|---|---|---|
| DOPAMINE D2 (DRD2) | Binding | pKi 8.7 |
| DOPAMINE D3 (DRD3) | Binding | pKi 8.6 |
| D2 receptor (DRD2) | Antagonist | pKi 7.8 |
| D3 | Binding | pKi 7.8 |
| 5-HT2B (HTR2B) | Binding | pKi 7.5 |
| 5-HT7 (HTR7) | Binding | pKi 7.4 |
| Alpha2A | Binding | pKi 7.0 |
| Alpha2B | Binding | pKi 6.3 |
| Alpha2C | Binding | pKi 6.0 |
| adrenergic Alpha2A (ADRA2A) | Binding | pKi 6.0 |
| 5-HT1D (HTR1D) | Binding | pKi 5.9 |
| adrenergic Alpha2C (ADRA2C) | Binding | pKi 5.8 |
| D4 | Binding | pKi 5.8 |
| 5-HT1B (HTR1B) | Binding | pKi 5.8 |
| DOPAMINE D4 (DRD4) | Binding | pKi 5.6 |
Transporters
BCRP (Inhibitor)BCRP (Inhibitor)BSEP (Inhibitor)BSEP (Inhibitor)MATE2 (Inhibitor)MDR1 (Inhibitor)MRP1 (Inhibitor)MRP2 (Inhibitor)MRP3 (Inhibitor)MRP4 (Inhibitor)OAT1 (Inhibitor)OAT3 (Inhibitor)OATP1B1 (Inhibitor)OATP1B3 (Inhibitor)OATP1B3 (Inhibitor)OCT1 (Inhibitor)OCT2 (Inhibitor)P-gp (Inhibitor)BCRP (Substrate)MATE2 (Substrate)MDR1 (Substrate)OCT1 (Substrate)OCTN1 (Substrate)OCTN2 (Substrate)P-gp (Substrate)
Drug–drug interactions (100+, DDInter)
| Interacting drug | Severity | Management |
|---|---|---|
| Abarelix | major | |
| Abiraterone | major | |
| Alimemazine | major | |
| Anagrelide | major | |
| Apalutamide | major | |
| Arsenic trioxide | major | |
| Astemizole | major | |
| Bicalutamide | major | |
| Bosutinib | major | |
| Cabozantinib | major | |
| Ceritinib | major | |
| Chloroquine | major | |
| Cilostazol | major | |
| Cisapride | major | |
| Clarithromycin | major | |
| Crizotinib | major | |
| Dasatinib | major | |
| Daunorubicin | major | |
| Daunorubicin (liposomal) | major | |
| Degarelix | major | |
| Dolasetron | major | |
| Doxepin | major | |
| Doxepin (topical) | major | |
| Doxorubicin | major | |
| Doxorubicin (liposomal) | major | |
| Encorafenib | major | |
| Entrectinib | major | |
| Enzalutamide | major | |
| Epirubicin | major | |
| Eribulin | major | |
| Erythromycin | major | |
| Fingolimod | major | |
| Fluconazole | major | |
| Flutamide | major | |
| Gilteritinib | major | |
| Glasdegib | major | |
| Goserelin | major | |
| Granisetron | major | |
| Halofantrine | major | |
| Histrelin | major |
Showing 40 of 100+.
Registered Products (17)
| Brand | Form / strength | Pack | Agent | Citizen (JOD) |
|---|---|---|---|---|
| Amilian | Tablet 50 mg | 30 tab pack varies | Al-Taqqadom Pharmaceutical Industries | 7.020 |
| Amex 50 Tablet | Tablet 50 mg | 30 tab | Jordan Sweden Medical & Sterilization Co. | 7.500 |
| Percepta | Tablet 50 mg | 30 tab | UNITED PHARM.MFG.CO.LTD(UPM)/JORDAN | 7.500 |
| Amex | Tablet 100 mg | 30 tab | Jordan Sweden Medical & Sterilization Co. | 7.880 |
| Amilian | Tablet 100 mg | 30 tab pack varies | Al-Taqqadom Pharmaceutical Industries | 8.180 |
| Percepta | Tablet 100 mg | 30 tab | UNITED PHARM.MFG.CO.LTD(UPM)/JORDAN | 8.180 |
| Solian Tab | Tablet 50 mg | 30 tab | Ulfa Pharma Co. | 9.370 |
| SOLIAN | Tablet 100 mg | 30 tab | Ulfa Pharma Co. | 10.510 |
| Amex | Tablet 200 mg | 30 tab | Jordan Sweden Medical & Sterilization Co. | 16.810 |
| Amilian | Tablet 200 mg | 30 tab pack varies | Al-Taqqadom Pharmaceutical Industries | 16.810 |
| Percepta | Tablet 200 mg | 30 tab | UNITED PHARM.MFG.CO.LTD(UPM)/JORDAN | 16.810 |
| SOLIAN | Tablet 200 mg | 30 tab | Ulfa Pharma Co. | 21.010 |
| Amex | Tablet 400 mg | 30 tab | Jordan Sweden Medical & Sterilization Co. | 36.540 |
| Percepta | Tablet 400 mg | 30 tab | UNITED PHARM.MFG.CO.LTD(UPM)/JORDAN | 40.000 |
| Amilian | Tablet 50 mg | 1000 tab pack varies | Al-Taqqadom Pharmaceutical Industries | 198.860 |
| Amilian | Tablet 100 mg | 1000 tab pack varies | Al-Taqqadom Pharmaceutical Industries | 231.710 |
| Amilian | Tablet 200 mg | 1000 tab pack varies | Al-Taqqadom Pharmaceutical Industries | 476.280 |