Ropivacaine
Naropin · (S)-N-(2,6-Dimethylphenyl)-1-propylpiperidine-2-carboxamide · S-ROPIVACAINE · ROPIVACAINE MESYLATER · RopivacaineHcl/MesylateBase · Seduron · Naropine · ROPIVACAINE
식별자 및 물리적 특성
| CAS No. | 84057-95-4 |
|---|---|
| 분자식 | C17H26N2O |
| 평균 분자량 | 274.4 g/mol |
| 단동위원소 질량 | 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 |
화학 및 물리적 성질
| XLogP | 2.9 |
|---|---|
| 극성 표면적 | 32.3 |
| 수소 결합 공여자 수 | 1 |
| 수소 결합 수용자 수 | 2 |
| 회전 가능 결합 수 | 4 |
| 무거운 원자 수 | 20 |
| 형식 전하 | 0 |
| 복잡도 | 308 |
| 의약품 | Pharmaceuticals -> Listed in ZINC15 |
| LogP(분배 계수) | 32.89 |
| 용해도 | 2.53e-01 g/L수용액 (약간 용해됨), 클로로포름 (약간 용해됨), DMSO (약간 용해됨) |
| Human Drugs | Breast FeedingLactationMilk, HumanAnesthetics, Local |
| Physical Description | Solid |
| Dissociation Constants | 8.07 |
| 녹는점 | 144-146° |
| 끓는 점 | 410.2±45.0 °C(Predicted) |
| 밀도 | 1.044±0.06 g/cm3(Predicted) |
| 저장 조건 | Refrigerator |
| 물리적 상태 | 고체 |
| pKa(산도 계수) | 8.16(at 25℃) |
| 색상 | 흰색에서 황백색까지 |
| 주요 응용 | 소분자 약용 |
| 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 |
안전 및 규제
| GHS 분류 | 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] |
|---|---|
| 규제 정보 | 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) |
| 건강 영향 | 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] |
| 유해 작용 | 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. |
용도
개요
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
용도
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
일반 설명
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.