ロピバカイン
S-ロピバカイン · (2S)-1-プロピル-2-(2,6-ジメチルフェニル)カルバモイルピペリジン · ロピバカイン · (2S)-1-プロピル-N-(2,6-ジメチルフェニル)ピペリジン-2-カルボアミド · (S)-ロピバカイン · (2S)-N-(2,6-ジメチルフェニル)-1-プロピルピペリジン-2-カルボキサミド · Naropin · (S)-N-(2,6-Dimethylphenyl)-1-propylpiperidine-2-carboxamide
識別子と物理属性
| CAS No. | 84057-95-4 |
|---|---|
| 分子式 | C17H26N2O |
| 平均分子量 | 274.4 g/mol |
| 単同位体質量 | 274.20451345 g/mol |
| SMILES | CCCN1CCCC[C@H]1C(=O)Nc1c(C)cccc1C |
| InChIKey | ZKMNUMMKYBVTFN-HNNXBMFYSA-N |
| PubChem CID | 175805 |
| ChEMBL | CHEMBL1077896 |
| ChEBI | CHEBI:8890 |
| EC No. | 617-525-1 |
| DTXSID | DTXSID4040187 |
| 現地名 | ロピバカイン |
化学・物理的性質
| XLogP | 2.9 |
|---|---|
| 極性表面積 | 32.3 |
| 水素結合供与体数 | 1 |
| 水素結合受容体数 | 2 |
| 回転可能結合数 | 4 |
| 重原子数 | 20 |
| 形式電荷 | 0 |
| 複雑度 | 308 |
| 医薬品 | Pharmaceuticals -> Listed in ZINC15 |
| LogP（分配係数） | 32.89 |
| 溶解度 | 2.53e-01 g/L水酸 (微量)、クロロホルム (微量)、DMSO (微量)、メタノール (微量) |
| Human Drugs | Breast FeedingLactationMilk, HumanAnesthetics, Local |
| Physical Description | Solid |
| Dissociation Constants | 8.07 |
| 融点 | 144-146° |
| 比旋光度 | D25 -82.0° (c = 2 in methanol) |
| 沸点 | 410.2±45.0 °C(Predicted) |
| 密度 | 1.044±0.06 g/cm3(Predicted) |
| 貯蔵条件 | Refrigerator |
| 外観・状態 | 個体 |
| pKa（酸解離定数） | 8.16(at 25℃) |
| 色 | ホワイトからオフホワイト |
| 主な用途 | 医薬品低分子化合物 |
| InChI | 1S/C17H26N2O/c1-4-11-19-12-6-5-10-15(19)17(20)18-16-13(2)8-7-9-14(16)3/h7-9,15H,4-6,10-12H2,1-3H3,(H,18,20)/t15-/m0/s1 |
| InChIKey | ZKMNUMMKYBVTFN-HNNXBMFYSA-N |
| SMILES | N1([C@@H](CCCC1)C(=O)Nc2c(cccc2C)C)CCC |
| CAS データベース | 84057-95-4(CAS DataBase Reference) |
安全性と法規制
| GHS 分類 | WarningH302 (86.7%): Harmful if swallowed [Warning Acute toxicity, oral]P261, P264, P264+P265, P270, P271, P273, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, P321, P330, P332+P317, P337+P317, P362+P364, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 15 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral] |
|---|---|
| 規制情報 | Status: Active Update: 11-10-2017 https://echa.europa.eu/registration-dossier/-/registered-dossier/20732 |
| Hazard Classes and Categories | Acute Tox. 4 (86.7%)Acute Tox. 4 (100%) |
| Treatment | The first step in the management of systemic toxic reactions consists of immediate attention to the establishment and maintenance of a patent airway and effective assisted or controlled ventilation with 100% oxygen with a delivery system capable of permitting immediate positive airway pressure by mask. Circulation should be assisted as necessary. If necessary, use drugs to control convulsions. Intravenous barbiturates, anticonvulsant agents, or muscle relaxants should only be administered by those familiar with their use. Immediately after the institution of these ventilatory measures, the adequacy of the circulation should be evaluated. Supportive treatment of circulatory depression may require administration of intravenous fluids, and, when appropriate, a vasopressor dictated by the clinical situation (such as ephedrine or epinephrine to enhance myocardial contractile force). (L1712) |
| 健康影響 | Systemic exposure to excessive quantities of lidocaine mainly result in central nervous system (CNS) and cardiovascular effects. CNS effects may include CNS excitation(nervousness, tingling around the mouth) followed by depression. [Wikipedia] |
| 有害作用 | Ropivacaine is generally well-tolerated. A pooled analysis from controlled clinical trials (n=1,661), in which patients received ropivacaine concentrations from 0.125% to 1% for nerve blocks, indicates that the most common adverse reactions are hypotension (32%), nausea (17%), vomiting (7%), bradycardia (6%), and headache (7%). A similar side effect profile occurred in patients who received bupivacaine concentrations of 0.25% to 0.75%. Overall, adverse events with ropivacaine are rare when it is properly administered. |
| 暴露経路 | Epidural. Bioavailability is 87%-98% following epidural administration. |
| 毒性の概要 | Signs and Symptoms of OverdoseLocal 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. |
| Signs and Symptoms | 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. |
| Carcinogen Classification | No indication of carcinogenicity to humans (not listed by IARC). |
| Effects During Pregnancy and Lactation | ◉ Summary of Use during Lactation |
| 水環境危害等級（WGK） | WGK 1 |
| 税関コード | 2933399090 |
| 危険等級 | STOT SE 1STOT SE 3 |
| 貯蔵分類 | 6.1D - Non-combustible acute toxic Cat.3toxic hazardous materials or hazardous materials causing chronic effects |
用途
説明
Ropivacaine is an aminoamide local anaesthetic drug commonly marketed by AstraZeneca under the trade name Naropin. Naropin was launched in 1996 in Australia, Denmark, Finland, the Netherlands and Sweden as a local anesthetic. It can be prepared in a number of ways the most efficient involves a three step sequence beginning with L-pipecolic acid. This compound is the first one in this family to be produced as the pure (S)- enantiomer. The (R)-enantiomer has been shown to have cardiotoxic effects. Thus ropivicaine has less cardiovascular and CNS toxicity than bupivacaine. It is a Na channel blocker that is specific for affecting nerve fibers responsible for transmission of pain (Aδ and C) with no effect on fibers responsible for motor function (Aβ). Clinically, it has distinct advantages over bupivacaine. Its effects are slower in onset, less intense and have a shorter duration. This is a result of extensive metabolism in the liver to the 3-hydroxy isomer by CYPIA2 isoenzyme.Ropivacaine is an anesthetic (numbing medicine) that blocks the nerve impulses that send pain signals to your brain.Ropivacaine is used as a local (in only one area) anesthesia for a spinal block, also called an epidural. The medication is used to provide anesthesia during a surgery or C-section, or to ease labor pains.https://www.drugs.com/mtm/ropivacaine.html
使用
Ropivacaine is a pure S(-)-enantiomer of propivacaine. It is a long-acting amide local anesthetic that has efficacy and potency nearly as high as bupivacaine and levobupivacaine but has lower CNS and cvS toxicity. If there are any differences between bupivacaine and ropivacaine it is the slightly shorter period of activity in spinal and epidural applications and a lowered ability to penetrate large motor nerves. It is the reduced lipophilicity that contributed to the lowered penetration of the motor nerves, combined with its stereoselective properties that allows ropivacaine to have significantly reduced Cvs toxicity compared to bupivacaine (Simpson et al. 2005). Ropivacaine has a diphasic effect on peripheral vasculature-it is vasoconstrictive when injected at a concentration below 0.5 w/v% and there is dilation at concentrations over 1 w/v% (Cederholm et al. 1992).Ropivacaine HCl is an anaesthetic agent and blocks impulse conduction in nerve fibres through inhibiting sodium ion influx reversibly.http://www.selleckchem.com/products/ropivacaine-hcl.html
一般的な説明
The recognized increase in cardiotoxicity of one bupivacaineisomer led to the stereospecific production of ropivacaine asthe single “S” (-) enantiomer. Ropivacaine is the propylanalog of mepivacaine (methyl) and bupivacaine (butyl). ThepKa of the tertiary nitrogen is 8.1, and it displays the same degreeof protein binding as bupivacaine ( 94%). Althoughropivacaine has similar properties as bupivacaine, it displaysless cardiotoxicity. The shortened alkyl chain gives it approximatelyone third of the lipid solubility of bupivacaine.