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药品详细

Oxazepam(奥沙西泮)

化学结构式图
中文名
奥沙西泮
英文名
Oxazepam
分子式
C15H11ClN2O2
化学名
7-chloro-3-hydroxy-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepin-2-one
分子量
Average: 286.713
Monoisotopic: 286.050905313
CAS号
604-75-1
ATC分类
N05B 未知
药物类型
small molecule
阶段
approved
商品名
同义名
基本介绍

Oxazepam is an intermediate-acting benzodiazepine used to treat alcohol withdrawal and anxiety disorders. Oxazepam is also the metabolite of other benzodiazpines.

生产厂家
  • Actavis elizabeth llc
  • Alpharma us pharmaceuticals division
  • American therapeutics inc
  • Ivax pharmaceuticals inc sub teva pharmaceuticals usa
  • Mutual pharmaceutical co inc
  • Mylan pharmaceuticals inc
  • Parke davis div warner lambert co
  • Quantum pharmics ltd
  • Sandoz inc
  • Watson laboratories inc
封装厂家
参考
Synthesis Reference Not Available
General Reference
  1. Peppers MP: Benzodiazepines for alcohol withdrawal in the elderly and in patients with liver disease. Pharmacotherapy. 1996 Jan-Feb;16(1):49-57. Pubmed
  2. Skerritt JH, Johnston GA: Enhancement of GABA binding by benzodiazepines and related anxiolytics. Eur J Pharmacol. 1983 May 6;89(3-4):193-8. Pubmed
  3. Oelschlager H: [Chemical and pharmacologic aspects of benzodiazepines] Schweiz Rundsch Med Prax. 1989 Jul 4;78(27-28):766-72. Pubmed
  4. Christensen P, Lolk A, Gram LF, Kragh-Sorensen P: Benzodiazepine-induced sedation and cortisol suppression. A placebo-controlled comparison of oxazepam and nitrazepam in healthy male volunteers. Psychopharmacology (Berl). 1992;106(4):511-6. Pubmed
  5. Olive G, Dreux C: [Pharmacologic bases of use of benzodiazepines in pereinatal medicine] Arch Fr Pediatr. 1977 Jan;34(1):74-89. Pubmed
  6. Altamura AC, Moliterno D, Paletta S, Maffini M, Mauri MC, Bareggi S: Understanding the pharmacokinetics of anxiolytic drugs. Expert Opin Drug Metab Toxicol. 2013 Apr;9(4):423-40. doi: 10.1517/17425255.2013.759209. Epub 2013 Jan 21. Pubmed
剂型
规格
化合物类型
Type small molecule
Classes
  • Benzodiazepines
  • Lactams
Substructures
  • Benzodiazepines
  • Hydroxy Compounds
  • Amino Ketones
  • Benzene and Derivatives
  • Aryl Halides
  • Carboxylic Acids and Derivatives
  • Halobenzenes
  • Heterocyclic compounds
  • Aromatic compounds
  • Carboxamides and Derivatives
  • Diazepines
  • Lactams
  • Imines
  • Anilines
适应症
药理
Indication For the treatment of anxiety disorders and alcohol withdrawal.
Pharmacodynamics Oxazepam is believed to stimulate GABA receptors in the ascending reticular activating system. Since GABA is inhibitory, receptor stimulation increases inhibition and blocks both cortical and limbic arousal following stimulation of the brain stem reticular formation.
Mechanism of action Similar to other benzodiazepines, oxazepam exerts its anxiolytic effects by potentiating the effect of gamma-aminobutyric acid (GABA) on GABA-A receptors through a cooperative mechanism of action. GABA receptors are ionotropic chloride-linked channel receptors that produce inhibitory postsynaptic potentials. When activated by GABA, the GABA receptor/chloride ionophore complex undergoes a conformational change that allows the passage of chloride ions through the channel. Benzodiazepines are believed to exert their effect by increasing the effect of GABA at its receptor. Benzodiazepine binding increases chloride conductance in the presence of GABA by increasing the frequency at which the channel opens. In contrast, barbiturates increase chloride conductance in the presence of GABA by prolonging the time in which the channel remains open. There are 18 subtypes of the GABA receptor subunits. The α2 subunit of the α2β3γ2 receptor complex is thought to mediate anxiolytic effects while the α1 subunit of the α1β2γ2 receptor complex is thought to mediate sedative, anticonvulsant and anterograde amnesia effects.
Absorption Well absorbed from the gastrointestinal tract following oral administration however is absorbed at a slower rate compared to other benzodiazepines like diazepam or flurazepam. Time to peak concentration = 2-4 hours. Onset of action is slow, > 3 hours, following oral administration.
Volume of distribution Not Available
Protein binding 80-99%
Metabolism
No active metabolites. It is hepatically metabolized and undergoes glucuronidation. The glucuronidation of the S-isomer is catalyzed by UGT2B15. The glucuronidation of the R-isomer is catalyzed by UGT2B7 and UGT1A9.
Route of elimination This product has a single, major inactive metabolite in man, a glucuronide excreted in the urine.
Half life Mean elimination half-life - 8.2 hours (range of 5.7 to 10.9 hours)
Clearance Not Available
Toxicity Symptoms of overdose include confusion, drowsiness, and lethargy.
Affected organisms
  • Humans and other mammals
Pathways Not Available
理化性质
Properties
State solid
Experimental Properties
Property Value Source
melting point 205-206 °C PhysProp
water solubility 179 mg/L Not Available
logP 2.24 HANSCH,C ET AL. (1995)
Predicted Properties
Property Value Source
water solubility 8.81e-02 g/l ALOGPS
logP 2.01 ALOGPS
logP 2.92 ChemAxon
logS -3.5 ALOGPS
pKa (strongest acidic) 10.61 ChemAxon
pKa (strongest basic) -1.5 ChemAxon
physiological charge 0 ChemAxon
hydrogen acceptor count 3 ChemAxon
hydrogen donor count 2 ChemAxon
polar surface area 61.69 ChemAxon
rotatable bond count 1 ChemAxon
refractivity 77.89 ChemAxon
polarizability 28.38 ChemAxon
药物相互作用
Drug Interaction
Clozapine Increased risk of toxicity
Kava Kava may increase the effect of the benzodiazepine, oxazepam.
Triprolidine The CNS depressants, Triprolidine and Oxazepam, may increase adverse/toxic effects due to additivity. Monitor for increased CNS depressant effects during concomitant therapy.
食物相互作用
  • Avoid alcohol.
  • Avoid excessive quantities of coffee or tea (Caffeine).
  • Take with food.

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