| 词条 | Droperidol |
| 释义 |
| UNII_Ref = {{fdacite|correct|FDA}} | UNII = O9U0F09D5X | IUPAC_name = 3-[1-[4-(4-fluorophenyl)-4-oxobutyl]-3,6-dihydro-2H-pyridin-4-yl]-1H-benzimidazol-2-one | image = Droperidol.svg | alt = Skeletal formula of droperidol | image2 = Droperidol-3D-balls.png | alt2 = Ball-and-stick model of droperidol | width = 240 | index_label = | index2_label = | CAS_number = 548-73-2 | ATC_prefix = N05 | ATC_suffix = AD08 | ATC_supplemental = | PubChem = 3168 | ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL = 1108 | DrugBank = DB00450 | KEGG = D00308 | ChemSpiderID = 3056 | SMILES = c1ccc2c(c1)nc(n2C3=CCN(CC3)CCCC(=O)c4ccc(cc4)F)O | StdInChI = 1S/C22H22FN3O2/c23-17-9-7-16(8-10-17)21(27)6-3-13-25-14-11-18(12-15-25)26-20-5-2-1-4-19(20)24-22(26)28/h1-2,4-5,7-11H,3,6,12-15H2,(H,24,28) | StdInChIKey = RMEDXOLNCUSCGS-UHFFFAOYSA-N | SMILES2 = Fc1ccc(cc1)C(=O)CCCN2CC=C(CC2)N3c4ccccc4NC3=O | C=22 | H=22 | F=1 | N=3 | O=2 | molecular_weight = 379.428 g/mol | bioavailability = | protein_bound = | metabolism = Hepatic| elimination_half-life = 2.3 hours | pregnancy_AU = C | pregnancy_US = C | legal_AU = S4 | legal_US = Rx-only | legal_UK = POM | routes_of_administration = Intravenous, Intramuscular }} Droperidol {{IPA|/droʊˈpɛrIdɔːl/}} (Inapsine, Droleptan, Dridol, Xomolix, Innovar [combination with fentanyl]) is an antidopaminergic drug used as an antiemetic (that is, to prevent or treat nausea) and as an antipsychotic. Droperidol is also often used as a sedative in intensive-care treatment. HistoryDiscovered at Janssen Pharmaceutica in 1961, droperidol is a butyrophenone which acts a potent D2 (dopamine receptor) antagonist with some histamine and serotonin antagonist activity.[1] Medical useIt has a central antiemetic action and effectively prevents postoperative nausea and vomiting in adults using doses as low as 0.625 mg. For treatment of nausea and vomiting, droperidol and ondansetron are equally effective; droperidol is more effective than metoclopramide.[2] It has also been used as an antipsychotic in doses ranging from 5 to 10 mg given as an intramuscular injection, generally in cases of severe agitation in a psychotic patient who is refusing oral medication. Its use in intramuscular sedation has been replaced by intramuscular preparations of haloperidol, midazolam, clonazepam and olanzapine. Some practitioners recommend the use of 0.5 mg to 1 mg intravenously for the treatment of vertigo in an otherwise healthy elderly patients who have not responded to Epley maneuvers. Black box warningIn 2001, the FDA changed the labeling requirements for droperidol injection to include a Black Box Warning, citing concerns of QT prolongation and torsades de pointes. The evidence for this is disputed, with 9 reported cases of torsades in 30 years and all of those having received doses in excess of 5 mg.[3] QT prolongation is a dose-related effect,[4] and it appears that droperidol is not a significant risk in low doses. A study in 2015 showed that droperidol is relatively safe and effective for the management of violent and aggressive adult [5]patients in hospital emergency departments in doses of 10mg and above and that there was no increased risk of QT prolongation and torsades de pointes. Side effectsDysphoria, sedation, hypotension resulting from peripheral alpha adrenoceptor blockade, prolongation of QT interval which can lead to torsades de pointes, and extrapyramidal side effects such as dystonic reactions/neuroleptic malignant syndrome.[6]ChemistryDroperidol is synthesized from 1-benzyl-3-carbethoxypiperidin-4-one, which is reacted with o-phenylendiamine. Evidently, the first derivative that is formed under the reaction conditions, 1,5-benzdiazepine, rearranges into 1-(1-benzyl-1,2,3,6-tetrahydro-4-piridyl)-2-benzymidazolone. Debenzylation of the resulting product with hydrogen over a palladium catalyst, and subsequent alkylation of this using 4-chloro-4'-fluorobutyrophenone yields droperidol.
(See pimozide article for proposed mechanism of intramolecular rearrangement.) References1. ^{{cite journal| vauthors = Peroutka SJ, Synder SH| title = Relationship of neuroleptic drug effects at brain dopamine, serotonin, alpha-adrenergic, and histamine receptors to clinical potency| journal = The American Journal of Psychiatry| volume = 137| issue = 12| pages = 1518–22|date=December 1980| pmid = 6108081| url = http://ajp.psychiatryonline.org/cgi/reprint/137/12/1518| accessdate = 2009-06-21| doi=10.1176/ajp.137.12.1518}} 2. ^{{cite journal| vauthors = Domino KB, Anderson EA, Polissar NL, Posner KL| title = Comparative efficacy and safety of ondansetron, droperidol, and metoclopramide for preventing postoperative nausea and vomiting: a meta-analysis| journal = Anesthesia and Analgesia| volume = 88| issue = 6| pages = 1370–9|date=June 1999| pmid = 10357347| doi = 10.1213/00000539-199906000-00032}} 3. ^{{cite journal| vauthors = Kao LW, Kirk MA, Evers SJ, Rosenfeld SH| title = Droperidol, QT prolongation, and sudden death: what is the evidence?| journal = Annals of Emergency Medicine| volume = 41| issue = 4| pages = 546–58|date=April 2003| pmid = 12658255| doi = 10.1067/mem.2003.110}} 4. ^{{cite journal| vauthors = Lischke V, Behne M, Doelken P, Schledt U, Probst S, Vettermann J| title = Droperidol causes a dose-dependent prolongation of the QT interval| journal = Anesthesia and Analgesia| volume = 79| issue = 5| pages = 983–6|date=November 1994| pmid = 7978420| doi = 10.1213/00000539-199411000-00028}} 5. ^{{cite journal |last1=Calver |first1=Leonie |last2=Page |first2=Colin |last3=Downes |first3=Michael |last4=Chan |first4=Betty |last5=Kinnear |first5=Frances |last6=Wheatley |first6=Luke |last7=Spain |first7=David |last8=Ibister |first8=Geoffrey |title=The safety and effectiveness of droperidol for sedation of acute behavioral disturbance in the emergency department |journal=Annals of Emergency Medicine |date=September 2015 |volume=66 |issue=3 |pages=231–238 |url=https://www.annemergmed.com/article/S0196-0644(15)00222-X/pdf |accessdate=18 July 2018}} 6. ^{{cite journal|vauthors=Park CK, Choi HY, Oh IY, Kim MS |title=Acute dystonia by droperidol during intravenous patient-controlled analgesia in young patients |journal=J. Korean Med. Sci. |volume=17 |issue=5 |pages=715–7 |year=2002 |pmid=12378031 |pmc=3054934 |doi= 10.3346/jkms.2002.17.5.715}} Further reading
| title = Pharmacodynamics | titlestyle = background:#ccccff | list1 ={{Acetylcholine receptor modulators}}{{Dopamine receptor modulators}}{{Histamine receptor modulators}}{{Serotonin receptor modulators}} }} 10 : Antiemetics|Belgian inventions|Benzimidazoles|Butyrophenone antipsychotics|Janssen Pharmaceutica|Lactams|Fluoroarenes|Tetrahydropyridines|Ureas|Typical antipsychotics |
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