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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2016/07/11 01:04:56」(JST)

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Droperidol /droʊˈpɛrIdɔːl/ (Inapsine, Droleptan, Dridol, Xomolix, Innovar [combination with fentanyl]) is an antidopaminergic drug used as an antiemetic and antipsychotic. Droperidol is also often used for neuroleptanalgesic anesthesia and sedation in intensive-care treatment.

History and use

Discovered at Janssen Pharmaceutica in 1961, droperidol is a butyrophenone, and is a potent D₂ (dopamine receptor) antagonist with some histamine and serotonin antagonist activity.^[1] It has a central antiemetic action and effectively prevents postoperative nausea and vomiting in adults using doses as low as 0.625 mg.^[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 Its use in intramuscular sedation has been replaced by intramuscular preparations of haloperidol, midazolam, clonazepam and olanzapine.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 warning

In 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.

Side effects

Dysphoria, 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.^[5]

Chemistry

Droperidol 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.

C. Janssen, NV Res. Lab., GB 989755 (1962).
Janssen, P. A. J.; 1963, Belgian Patent BE 626307 .
F.J. Gardocki, J. Janssen, U.S. Patent 3,141,823 (1964).
P.A.J. Janssen, U.S. Patent 3,161,645 (1964).

(See pimozide article for proposed mechanism of intramolecular rearrangement.)

References

^ Peroutka SJ, Synder SH (December 1980). "Relationship of neuroleptic drug effects at brain dopamine, serotonin, alpha-adrenergic, and histamine receptors to clinical potency". The American Journal of Psychiatry 137 (12): 1518–22. PMID 6108081. Retrieved 2009-06-21.
^ Domino KB, Anderson EA, Polissar NL, Posner KL (June 1999). "Comparative efficacy and safety of ondansetron, droperidol, and metoclopramide for preventing postoperative nausea and vomiting: a meta-analysis". Anesthesia and Analgesia 88 (6): 1370–9. doi:10.1097/00000539-000000000-00000. PMID 10357347.
^ Kao LW, Kirk MA, Evers SJ, Rosenfeld SH (April 2003). "Droperidol, QT prolongation, and sudden death: what is the evidence?". Annals of Emergency Medicine 41 (4): 546–58. doi:10.1067/mem.2003.110. PMID 12658255.
^ Lischke V, Behne M, Doelken P, Schledt U, Probst S, Vettermann J (November 1994). "Droperidol causes a dose-dependent prolongation of the QT interval". Anesthesia and Analgesia 79 (5): 983–6. doi:10.1213/00000539-000000000-00000. PMID 7978420.
^ Park CK, Choi HY, Oh IY, Kim MS (2002). "Acute dystonia by droperidol during intravenous patient-controlled analgesia in young patients". J. Korean Med. Sci. 17 (5): 715–7. doi:10.3346/jkms.2002.17.5.715. PMC 3054934. PMID 12378031. Retrieved 2015-01-15.

UpToDate Contents

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1. 妊娠の悪心および嘔吐の治療および転帰 treatment and outcome of nausea and vomiting of pregnancy
2. 第1世代抗精神病剤：薬理学、投与、および副作用の比較 first generation antipsychotic medications pharmacology administration and comparative side effects
3. 制吐剤の特性 characteristics of antiemetic drugs
4. 消化管内視鏡検査のための中等度鎮静の代替薬および補助薬 alternatives and adjuncts to moderate procedural sedation for gastrointestinal endoscopy
5. 興奮または暴力的になった成人の評価と救急対応 assessment and emergency management of the acutely agitated or violent adult

English Journal

Compatibility of butorphanol and droperidol in 0.9% sodium chloride injection.

Chen FC, Fang BX, Li P, Yang JG, Zhou BH.SourceFu-Chao Chen, M.Pharm., is Hospital Pharmacist; Bao-Xia Fang, B.S.Pharm., is Hospital Pharmacist; and Peng Li, Pharm.D., is Director, Department of Pharmacy, Dongfeng Hospital (DH), Hubei University of Medicine, Hubei, Republic of China.
American journal of health-system pharmacy : AJHP : official journal of the American Society of Health-System Pharmacists.Am J Health Syst Pharm.2013 Mar 15;70(6):515-9. doi: 10.2146/ajhp120324.
PURPOSE: The compatibility and stability of butorphanol tartrate and droperidol in polyvinyl chloride (PVC) bags and glass bottles stored at 4°C and 25°C for up to 15 days were studied.METHODS: Admixtures were assessed initially and for 15 days after preparation in PVC bags and glass bottles using
PMID 23456405

A granisetron-droperidol combination prevents postoperative vomiting in children: retraction.

[No authors listed]
Anesthesia and analgesia.Anesth Analg.2013 Mar;116(3):743. doi: 10.1213/ANE.0b013e31828ac36f.
PMID 23439824

Japanese Journal

術後の嘔気・嘔吐 : 選択的ニューロキニン１受容体拮抗薬が及ぼす影響

門田尚子,堤保夫,大下修造,角田奈美,田中克哉,Kadota Takako,Tsutsumi Yasuo,Oshita Syuzo,Kakuta Nami,Tanaka. Katsuya
四国医学雑誌 67(3-4), 143-146, 2011-08-25
… Primary control of nausea and vomiting arises from the centralpattern generator for vomiting located in the medulla oblongara.Traditionally, the most common anti-emetics used to treat PONV include serotonin ５-hydroxytryptamine type３antagonists such as ondansetron, corticosteroids, like dexamethasone,or droperidol, which is a neuroleptic. …
NAID 120003558662

Human plasma quantification of droperidol and ondansetron used in preventing postoperative nausea and vomiting with a LC/ESI/MS/MS method

ALVAREZ Jean-Claude,CHARBIT Beny,GRASSIN-DELYLE Stanislas,DEMOLIS Jean-Louis,FUNCK-BRENTANO Christian,ABE Emuri
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 879(2), 186-190, 2011-01-15
NAID 10029025845

「ドロペリドール」

Droperidol
Systematic (IUPAC) name
	3-[1-[4-(4-fluorophenyl)-4-oxobutyl]-3,6-dihydro-2H-pyridin-4-yl]-1H-benzimidazol-2-one
Clinical data
Pregnancy; category	C (US);
Routes of; administration	Intravenous, Intramuscular
Legal status
Legal status	UK: POM (Prescription only); US: ℞-only;
Pharmacokinetic data
Metabolism	Hepatic
Biological half-life	2.3 hours
Identifiers
CAS Number	548-73-2
ATC code	N05AD08 (WHO)
PubChem	CID 3168
DrugBank	DB00450
ChemSpider	3056
UNII	O9U0F09D5X
KEGG	D00308
ChEMBL	CHEMBL1108
Chemical data
Formula	C22H22FN3O2
Molar mass	379.428 g/mol
	SMILES c1ccc2c(c1)nc(n2C3=CCN(CC3)CCCC(=O)c4ccc(cc4)F)O ; ; Fc1ccc(cc1)C(=O)CCCN2CC=C(CC2)N3c4ccccc4NC3=O ;
	InChI InChI=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) ; Key:RMEDXOLNCUSCGS-UHFFFAOYSA-N ;

　　[★]

英: droperidol
商: ドロレプタン

全身麻酔薬

ニューロレプト麻酔

向精神薬(抗精神病薬)であるハロペリドールに似た性質を持つが、ニューロレプト麻酔法のためにフェンタニルと組み合わせて用いられる

適応

ニューロレプト麻酔法による全身麻酔

[Per-1] Peroutka SJ, Synder SH (December 1980). "Relationship of neuroleptic drug effects at brain dopamine, serotonin, alpha-adrenergic, and histamine receptors to clinical potency". The American Journal of Psychiatry 137 (12): 1518–22. PMID 6108081. Retrieved 2009-06-21.

[pmid10357347-2] Domino KB, Anderson EA, Polissar NL, Posner KL (June 1999). "Comparative efficacy and safety of ondansetron, droperidol, and metoclopramide for preventing postoperative nausea and vomiting: a meta-analysis". Anesthesia and Analgesia 88 (6): 1370–9. doi:10.1097/00000539-000000000-00000. PMID 10357347.

[Kao-3] Kao LW, Kirk MA, Evers SJ, Rosenfeld SH (April 2003). "Droperidol, QT prolongation, and sudden death: what is the evidence?". Annals of Emergency Medicine 41 (4): 546–58. doi:10.1067/mem.2003.110. PMID 12658255.

[4] Lischke V, Behne M, Doelken P, Schledt U, Probst S, Vettermann J (November 1994). "Droperidol causes a dose-dependent prolongation of the QT interval". Anesthesia and Analgesia 79 (5): 983–6. doi:10.1213/00000539-000000000-00000. PMID 7978420.

[pmid12378031-5] Park CK, Choi HY, Oh IY, Kim MS (2002). "Acute dystonia by droperidol during intravenous patient-controlled analgesia in young patients". J. Korean Med. Sci. 17 (5): 715–7. doi:10.3346/jkms.2002.17.5.715. PMC 3054934. PMID 12378031. Retrieved 2015-01-15.

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droperidol