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药品详细

Promethazine(异丙嗪)

化学结构式图
中文名
异丙嗪
英文名
Promethazine
分子式
C17H20N2S
化学名
dimethyl[1-(10H-phenothiazin-10-yl)propan-2-yl]amine
分子量
Average: 284.419
Monoisotopic: 284.13471934
CAS号
60-87-7
ATC分类
D04A 未知;R06A 未知;R06A 未知
药物类型
small molecule
阶段
approved
商品名
同义名
基本介绍

A phenothiazine derivative with histamine H1-blocking, antimuscarinic, and sedative properties. It is used as an antiallergic, in pruritus, for motion sickness and sedation, and also in animals. [PubChem]

生产厂家
  • Abbott laboratories pharmaceutical products div
  • Able laboratories inc
  • Actavis mid atlantic llc
  • Actavis totowa llc
  • Akorn inc
  • Alpharma us pharmaceuticals division
  • Altana inc
  • Amneal pharmaceuticals
  • Ani pharmaceuticals inc
  • Baxter healthcare corp anesthesia and critical care
  • Bedford laboratories
  • Bioniche pharma usa llc
  • Bristol myers squibb pharma co
  • G and w laboratories inc
  • Hi tech pharmacal co inc
  • Hikma farmaceutica (portugal) sa
  • Hospira inc
  • Impax laboratories inc
  • Ivax pharmaceuticals inc sub teva pharmaceuticals usa
  • Kv pharmaceutical co
  • Kvk tech inc
  • Lannett co inc
  • Marsam pharmaceuticals llc
  • Mutual pharmaceutical co inc
  • Paddock laboratories inc
  • Perrigo new york inc
  • Pharmaceutical assoc inc div beach products
  • Pharmaforce inc
  • Polymedica industries inc
  • Private formulations inc
  • Sandoz inc
  • Sun pharmaceutical industries inc
  • Tablicaps inc
  • Taro pharmaceuticals usa inc
  • Teva parenteral medicines inc
  • Teva pharmaceuticals usa inc
  • Usl pharma inc
  • Victory pharma inc
  • Vintage pharmaceuticals inc
  • Vintage pharmaceuticals llc
  • Watson laboratories inc
  • Whiteworth towne paulsen inc
  • Wockhardt eu operations (swiss) ag
  • Wockhardt ltd
  • Wyeth ayerst laboratories
  • Wyeth pharmaceuticals inc
  • Zydus pharmaceuticals usa inc
封装厂家
参考
Synthesis Reference Not Available
General Reference
  1. Peters RJ Jr, Kelder SH, Markham CM, Yacoubian GS Jr, Peters LA, Ellis A: Beliefs and social norms about codeine and promethazine hydrochloride cough syrup (CPHCS) onset and perceived addiction among urban Houstonian adolescents: an addiction trend in the city of lean. J Drug Educ. 2003;33(4):415-25. Pubmed
剂型
规格
化合物类型
Type small molecule
Classes
  • Phenothiazines
Substructures
  • Ethers
  • Phenothiazines
  • Aliphatic and Aryl Amines
  • Thiazines
  • Benzene and Derivatives
  • Heterocyclic compounds
  • Aromatic compounds
  • Anilines
适应症
药理
Indication For the treatment of allergic disorders, and nausea/vomiting.
Pharmacodynamics Promethazine, a phenothiazine, is an H1-antagonist with anticholinergic, sedative, and antiemetic effects and some local anesthetic properties. Promethazine is used as an antiemetic or to prevent motion sickness.
Mechanism of action Like other H1-antagonists, promethazine competes with free histamine for binding at H1-receptor sites in the GI tract, uterus, large blood vessels, and bronchial muscle. The relief of nausea appears to be related to central anticholinergic actions and may implicate activity on the medullary chemoreceptor trigger zone.
Absorption On average, 88% of a promethazine dose is absorbed after oral administration; however, the absolute bioavailability is only 25% because of first-pass clearance.
Volume of distribution Not Available
Protein binding 93%
Metabolism
Hepatic
Route of elimination Promethazine hydrochloride is metabolized in the liver, with the sulfoxides of promethazine and N-desmethylpromethazine being the predominant metabolites appearing in the urine.
Half life 16-19 hours
Clearance Not Available
Toxicity Symptoms of overdose include mild depression of the central nervous system and cardiovascular system to profound hypotension, respiratory depression, unconsciousness, and sudden death. Other reported reactions include hyperreflexia, hypertonia, ataxia, athetosis, and extensor-plantar reflexes (Babinski reflex). LD50=55mg/kg (I.V. in mice)
Affected organisms
  • Humans and other mammals
Pathways Not Available
理化性质
Properties
State solid
Experimental Properties
Property Value Source
melting point 60 °C PhysProp
boiling point 190-192 °C at 3.00E+00 mm Hg PhysProp
water solubility 15.6 mg/L (at 24 °C) YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP 4.81 HANSCH,C ET AL. (1995)
logS -4.26 ADME Research, USCD
pKa 9.1 SANGSTER (1994)
Predicted Properties
Property Value Source
water solubility 2.45e-02 g/l ALOGPS
logP 4.52 ALOGPS
logP 4.29 ChemAxon
logS -4.1 ALOGPS
pKa (strongest basic) 9.05 ChemAxon
physiological charge 1 ChemAxon
hydrogen acceptor count 2 ChemAxon
hydrogen donor count 0 ChemAxon
polar surface area 6.48 ChemAxon
rotatable bond count 3 ChemAxon
refractivity 88.5 ChemAxon
polarizability 32.38 ChemAxon
药物相互作用
Drug Interaction
Amphetamine Decreased anorexic effect, may increase pyschotic symptoms
Benzphetamine Antipsychotics may diminish the stimulatory effect of Amphetamines. Monitor effectiveness of amphetamine therapy when altering concurrent antipsychotic therapy as antipsychotic agents may impair the stimulatory effect of amphetamines.
Bromocriptine The phenothiazine decreases the effect of bromocriptine
Cisapride Increased risk of cardiotoxicity and arrhythmias
Desvenlafaxine Increased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome.
Dexfenfluramine Decreased anorexic effect, may increase pyschotic symptoms.
Dextroamphetamine Decreased anorexic effect, may increase pyschotic symptoms
Diethylpropion Decreased anorexic effect, may increase psychotic symptoms.
Donepezil Possible antagonism of action
Fenfluramine Decreased anorexic effect, may increase psychotic symptoms.
Galantamine Possible antagonism of action
Gatifloxacin Increased risk of cardiotoxicity and arrhythmias
Grepafloxacin Increased risk of cardiotoxicity and arrhythmias
Guanethidine Promethazine may decrease the effect of guanethidine.
Levofloxacin Increased risk of cardiotoxicity and arrhythmias
Mazindol Decreased anorexic effect, may increase psychotic symptoms.
Methamphetamine Decreased anorexic effect, may increase pyschotic symptoms
Metrizamide Increased risk of convulsions
Phendimetrazine Decreased anorexic effect, may increase pyschotic symptoms
Phenmetrazine Decreased anorexic effect, may increase pyschotic symptoms
Phentermine Decreased anorexic effect, may increase psychotic symptoms.
Phenylpropanolamine Decreased anorexic effect, may increase psychotic symptoms.
Rivastigmine Possible antagonism of action
Sparfloxacin Increased risk of cardiotoxicity and arrhythmias
Tacrine The therapeutic effects of the central acetylcholinesterase inhibitor, Tacrine, and/or the anticholinergic, Promethazine, may be reduced due to antagonism. The interaction may be beneficial when the anticholinergic action is a side effect. Monitor for decreased efficacy of both agents.
Terbinafine Terbinafine may reduce the metabolism and clearance of Promethazine. Consider alternate therapy or monitor for therapeutic/adverse effects of Promethazine if Terbinafine is initiated, discontinued or dose changed.
Terfenadine Increased risk of cardiotoxicity and arrhythmias
Thiotepa Thiotepa, a strong CYP2B6 inhibitor, may decrease the metabolism and clearance of Promethazine, a CYP2B6 substrate. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of Promethazine if Thiotepa is initiated, discontinued or dose changed.
Tramadol Increased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome.
Tranylcypromine Increased risk of serotonin syndrome. Use caution during concomitant therapy and monitor for symptoms of serotonin syndrome.
Trazodone Increased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome.
Trimethobenzamide Trimethobenzamide and Promethazine, two anticholinergics, may cause additive anticholinergic effects and enhance their adverse/toxic effects. Monitor for enhanced anticholinergic effects.
Trimipramine Increased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome.
Triprolidine Triprolidine and Promethazine, two anticholinergics, may cause additive anticholinergic effects and enhance their adverse/toxic effects. Monitor for enhanced anticholinergic effects.
Trospium Trospium and Promethazine, two anticholinergics, may cause additive anticholinergic effects and enhanced adverse/toxic effects. Monitor for enhanced anticholinergic effects.
Venlafaxine Increased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome.
Zolmitriptan Use of two serotonin modulators, such as zolmitriptan and promethazine, increases the risk of serotonin syndrome. Consider alternate therapy or monitor for serotonin syndrome during concomitant therapy.
食物相互作用
  • Take with food to reduce irritation. Avoid alcohol.

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