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药品详细

Ropivacaine(罗哌卡因)

化学结构式图
中文名
罗哌卡因
英文名
Ropivacaine
分子式
C17H26N2O
化学名
(2S)-N-(2,6-dimethylphenyl)-1-propylpiperidine-2-carboxamide
分子量
Average: 274.4011
Monoisotopic: 274.204513464
CAS号
84057-95-4
ATC分类
N01B 未知
药物类型
small molecule
阶段
approved
商品名
同义名
基本介绍

Ropivacaine is a local anaesthetic drug belonging to the amino amide group. The name ropivacaine refers to both the racemate and the marketed S-enantiomer. Ropivacaine hydrochloride is commonly marketed by AstraZeneca under the trade name Naropin. [Wikipedia]

生产厂家
  • App pharmaceuticals llc
封装厂家
参考
Synthesis Reference Not Available
General Reference
  1. Weinberg G, Ripper R, Feinstein DL, Hoffman W: Lipid emulsion infusion rescues dogs from bupivacaine-induced cardiac toxicity. Reg Anesth Pain Med. 2003 May-Jun;28(3):198-202. Pubmed
  2. Picard J, Meek T: Lipid emulsion to treat overdose of local anaesthetic: the gift of the glob. Anaesthesia. 2006 Feb;61(2):107-9. Pubmed
  3. Rosenblatt MA, Abel M, Fischer GW, Itzkovich CJ, Eisenkraft JB: Successful use of a 20% lipid emulsion to resuscitate a patient after a presumed bupivacaine-related cardiac arrest. Anesthesiology. 2006 Jul;105(1):217-8. Pubmed
剂型
规格
化合物类型
Type small molecule
Classes Not Available
Substructures Not Available
适应症
药理
Indication Used in obstetric anesthesia and regional anesthesia for surgery.
Pharmacodynamics Ropivacaine, a local anesthetic agent, is indicated for the production of local or regional anesthesia or analgesia for surgery, for oral surgery procedures, for diagnostic and therapeutic procedures, and for obstetrical procedures.
Mechanism of action Local anesthetics such as Ropivacaine block the generation and the conduction of nerve impulses, presumably by increasing the threshold for electrical excitation in the nerve, by slowing the propagation of the nerve impulse, and by reducing the rate of rise of the action potential. Specifically, they block the sodium-channel and decrease chances of depolarization and consequent action potentials. In general, the progression of anesthesia is related to the diameter, myelination and conduction velocity of affected nerve fibers.
Absorption Bioavailability is 87%–98% following epidural administration.
Volume of distribution Not Available
Protein binding 94%, mainly to a1-acid glycoprotein
Metabolism
Hepatic

Important The metabolism module of DrugBank is currently in beta. Questions or suggestions? Please contact us.

Substrate Enzymes Product
Ropivacaine
3-hydroxyropivacaine Details
Route of elimination Ropivacaine is extensively metabolized in the liver, predominantly by aromatic hydroxylation mediated by cytochrome P4501A to 3-hydroxy ropivacaine. After a single IV dose approximately 37% of the total dose is excreted in the urine as both free and conjugated 3-hydroxy ropivacaine. In total, 86% of the ropivacaine dose is excreted in the urine after intravenous administration of which only 1% relates to unchanged drug.
Half life Approximately 4.2 hours.
Clearance
  • 387 +/- 107 mL/min
  • unbound plasma clearance=7.2 +/- 1.6 L/min
Toxicity Systemic exposure to excessive quantities of ropivacaine mainly result in central nervous system (CNS) and cardiovascular effects – CNS effects usually occur at lower blood plasma concentrations and additional cardiovascular effects present at higher concentrations, though cardiovascular collapse may also occur with low concentrations. CNS effects may include CNS excitation (nervousness, tingling around the mouth, tinnitus, tremor, dizziness, blurred vision, seizures) followed by depression (drowsiness, loss of consciousness, respiratory depression and apnea). Cardiovascular effects include hypotension, bradycardia, arrhythmias, and/or cardiac arrest – some of which may be due to hypoxemia secondary to respiratory depression.
Affected organisms
  • Humans and other mammals
Pathways
Pathway Name SMPDB ID
Smp00404 Ropivacaine Pathway SMP00404
理化性质
Properties
State solid
Experimental Properties
Property Value Source
water solubility 57.6 mg/L Not Available
logP 2.90 HANSCH,C ET AL. (1995)
pKa 8.07 Not Available
Predicted Properties
Property Value Source
water solubility 2.53e-01 g/l ALOGPS
logP 2.91 ALOGPS
logP 4.07 ChemAxon
logS -3 ALOGPS
pKa (strongest acidic) 13.62 ChemAxon
pKa (strongest basic) 7.82 ChemAxon
physiological charge 1 ChemAxon
hydrogen acceptor count 2 ChemAxon
hydrogen donor count 1 ChemAxon
polar surface area 32.34 ChemAxon
rotatable bond count 4 ChemAxon
refractivity 85.59 ChemAxon
polarizability 32.31 ChemAxon
药物相互作用
Drug Interaction
Fluvoxamine Increases the effect and toxicity of ropivacaine
食物相互作用
Not Available

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