Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C17H26N2O |
Molecular Weight | 274.4011 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CCCN1CCCC[C@H]1C(=O)NC2=C(C)C=CC=C2C
InChI
InChIKey=ZKMNUMMKYBVTFN-HNNXBMFYSA-N
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
Molecular Formula | C17H26N2O |
Molecular Weight | 274.4011 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
Ropivacaine is a member of the amino amide class of local anesthetics and is supplied as the pure S-(-)-enantiomer. It produces effects similar to other local anesthetics via reversible inhibition of sodium ion influx in nerve fibers. Ropivacaine is less lipophilic than bupivacaine and is less likely to penetrate large myelinated motor fibers, resulting in a relatively reduced motor blockade. Thus, ropivacaine has a greater degree of motor-sensory differentiation, which could be useful when the motor blockade is undesirable. The reduced lipophilicity is also associated with decreased potential for central nervous system toxicity and cardiotoxicity. Ropivacaine is indicated for the production of local or regional anesthesia for surgery and for acute pain management.
CNS Activity
Sources: https://www.ncbi.nlm.nih.gov/pubmed/21712863 | https://www.ncbi.nlm.nih.gov/pubmed/9564403
Curator's Comment: Ropivacaine exerts CNS toxicity
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL1980 |
2.73 µM [IC50] | ||
Target ID: CHEMBL4306 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9066339 |
80.0 µM [Kd] | ||
Target ID: CHEMBL240 Sources: https://www.ncbi.nlm.nih.gov/pubmed/14665560 |
20.0 µM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | NAROPIN Approved UseRopivacaine Hydrochloride Injection is indicated for the production of local or regional anesthesia for surgery and for acute pain management. Surgical Anesthesia: epidural block for surgery including cesarean section; major nerve block; local infiltration Acute Pain Management: epidural continuous infusion or intermittent bolus, eg, postoperative or labor; local infiltration Launch Date1996 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1.2 mg/L |
40 mg 1 times / day other, intravenous dose: 40 mg route of administration: Intravenous experiment type: OTHER co-administered: |
ROPIVACAINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
1.6 mg/L |
187.5 mg single, epidural dose: 187.5 mg route of administration: Epidural experiment type: SINGLE co-administered: |
ROPIVACAINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE food status: UNKNOWN |
|
2.3 mg/L |
300 mg single, epidural dose: 300 mg route of administration: Epidural experiment type: SINGLE co-administered: |
ROPIVACAINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
2.4 mg/L |
1493 mg other, epidural dose: 1493 mg route of administration: Epidural experiment type: OTHER co-administered: |
ROPIVACAINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
2.8 mg/L |
2075 mg other, epidural dose: 2075 mg route of administration: Epidural experiment type: OTHER co-administered: |
ROPIVACAINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
1.1 mg/L |
150 mg single, epidural dose: 150 mg route of administration: Epidural experiment type: SINGLE co-administered: |
ROPIVACAINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1.8 mg × h/L |
40 mg 1 times / day other, intravenous dose: 40 mg route of administration: Intravenous experiment type: OTHER co-administered: |
ROPIVACAINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
11.3 mg × h/L |
187.5 mg single, epidural dose: 187.5 mg route of administration: Epidural experiment type: SINGLE co-administered: |
ROPIVACAINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE food status: UNKNOWN |
|
13 mg × h/L |
300 mg single, epidural dose: 300 mg route of administration: Epidural experiment type: SINGLE co-administered: |
ROPIVACAINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
135.5 mg × h/L |
1493 mg other, epidural dose: 1493 mg route of administration: Epidural experiment type: OTHER co-administered: |
ROPIVACAINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
145 mg × h/L |
2075 mg other, epidural dose: 2075 mg route of administration: Epidural experiment type: OTHER co-administered: |
ROPIVACAINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
7.2 mg × h/L |
150 mg single, epidural dose: 150 mg route of administration: Epidural experiment type: SINGLE co-administered: |
ROPIVACAINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1.9 h |
40 mg 1 times / day other, intravenous dose: 40 mg route of administration: Intravenous experiment type: OTHER co-administered: |
ROPIVACAINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
7.1 h |
187.5 mg single, epidural dose: 187.5 mg route of administration: Epidural experiment type: SINGLE co-administered: |
ROPIVACAINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE food status: UNKNOWN |
|
6.8 h |
300 mg single, epidural dose: 300 mg route of administration: Epidural experiment type: SINGLE co-administered: |
ROPIVACAINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
5 h |
1493 mg other, epidural dose: 1493 mg route of administration: Epidural experiment type: OTHER co-administered: |
ROPIVACAINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
5.7 h |
2075 mg other, epidural dose: 2075 mg route of administration: Epidural experiment type: OTHER co-administered: |
ROPIVACAINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
5.7 h |
150 mg single, epidural dose: 150 mg route of administration: Epidural experiment type: SINGLE co-administered: |
ROPIVACAINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
300 mg single, intravascular Overdose Dose: 300 mg Route: intravascular Route: single Dose: 300 mg Sources: |
healthy, 25 years n = 1 Health Status: healthy Age Group: 25 years Sex: F Population Size: 1 Sources: |
Other AEs: Convulsion... |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Convulsion | 1 patient | 300 mg single, intravascular Overdose Dose: 300 mg Route: intravascular Route: single Dose: 300 mg Sources: |
healthy, 25 years n = 1 Health Status: healthy Age Group: 25 years Sex: F Population Size: 1 Sources: |
PubMed
Title | Date | PubMed |
---|---|---|
Comparative systemic toxicity of convulsant and supraconvulsant doses of intravenous ropivacaine, bupivacaine, and lidocaine in the conscious dog. | 1989 Dec |
|
Central nervous and cardiovascular effects of i.v. infusions of ropivacaine, bupivacaine and placebo in volunteers. | 1997 May |
|
Convulsions induced by ropivacaine during interscalene brachial plexus block. | 1997 Nov |
|
Ropivacaine inhibits leukocyte rolling, adhesion and CD11b/CD18 expression. | 1997 Oct |
|
Ventricular arrhythmias with or without programmed electrical stimulation after incremental overdosage with lidocaine, bupivacaine, levobupivacaine, and ropivacaine. | 2000 Nov |
|
Patient-controlled interscalene analgesia with ropivacaine 0.2% versus bupivacaine 0.15% after major open shoulder surgery: the effects on hand motor function. | 2001 Jan |
|
Cardiac resuscitation after incremental overdosage with lidocaine, bupivacaine, levobupivacaine, and ropivacaine in anesthetized dogs. | 2001 Jan |
|
Seizure induced by ropivacaine. | 2001 Mar |
|
[Comparison of ropivacaine and bupivacaine for epidural analgesia during labor]. | 2001 May |
|
Systemic toxicity and resuscitation in bupivacaine-, levobupivacaine-, or ropivacaine-infused rats. | 2001 Sep |
|
Ropivacaine-induced convulsion immediately after epidural administration--a case report. | 2002 Mar |
|
Loss of consciousness from epidural sufentanil for labour analgesia. | 2003 May |
|
[Pain control with epidural anesthesia for uterine artery embolization]. | 2004 Apr |
|
Ropivacaine-induced asystole: "never again" rather than "here we go again". | 2004 Aug |
|
[Convulsions induced by ropivacaine after brachial plexus block]. | 2004 Nov |
|
Ectopic expression of clusterin/apolipoprotein J or Bcl-2 decreases the sensitivity of HaCaT cells to toxic effects of ropivacaine. | 2004 Oct |
|
Pain control with low-dose alfentanil in children undergoing minor abdominal and genito-urinary surgery. | 2004 Sep |
|
Transdermal buprenorphine combined with spinal morphine and naropine for pain relief in chronic peripheral vasculopathy. | 2005 Jul-Aug |
|
Prediction of genotoxicity of chemical compounds by statistical learning methods. | 2005 Jun |
|
Successful resuscitation of a patient with ropivacaine-induced asystole after axillary plexus block using lipid infusion. | 2006 Aug |
|
Successful resuscitation of an ASA 3 patient following ropivacaine-induced cardiac arrest. | 2006 Dec |
|
Minimum local anaesthetic dose (MLAD) of intrathecal levobupivacaine and ropivacaine for Caesarean section. | 2006 Feb |
|
Lipid emulsion to treat overdose of local anaesthetic: the gift of the glob. | 2006 Feb |
|
Successful use of a 20% lipid emulsion to resuscitate a patient after a presumed bupivacaine-related cardiac arrest. | 2006 Jul |
|
Long QT 1 mutation KCNQ1A344V increases local anesthetic sensitivity of the slowly activating delayed rectifier potassium current. | 2006 Sep |
|
The effect of epidural sufentanil in ropivacaine on urinary retention in patients undergoing gastrectomy. | 2006 Sep |
|
[Grand mal convulsion after an interscalene block with ropivacaine]. | 2009 Apr |
|
Regional anesthesia for carotid endarterectomy: a comparison between ropivacaine and levobupivacaine. | 2009 May |
|
Local anesthesia with ropivacaine for patients undergoing laparoscopic cholecystectomy. | 2009 May 21 |
|
Repeated intrathecal administration of ropivacaine causes neurotoxicity in rats. | 2009 Nov |
|
Convulsions associated with a low plasma level of local anaesthetics. | 2009 Nov |
|
Lipid emulsion improves recovery from bupivacaine-induced cardiac arrest, but not from ropivacaine- or mepivacaine-induced cardiac arrest. | 2009 Oct |
|
The addition of fentanyl to 1.5 mg/ml ropivacaine has no advantage for paediatric epidural analgesia. | 2009 Sep |
|
Effects of mixture of lidocaine and ropivacaine at different concentrations on the central nervous system and cardiovascular toxicity in rats. | 2010 Jan 5 |
|
Apoptosis and mitochondrial dysfunction in human chondrocytes following exposure to lidocaine, bupivacaine, and ropivacaine. | 2010 Mar |
Sample Use Guides
The dose of any local anesthetic administered varies with the anesthetic procedure, the area to be anesthetized, the vascularity of the tissues, the number of neuronal segments to be blocked, the depth of anesthesia and degree of muscle relaxation required, the duration of anesthesia desired, individual tolerance, and the physical condition of the patient.
For treatment of postoperative pain, the following technique can be recommended: If regional anesthesia was not used intraoperatively, then an initial epidural block with 5-7 mL Naropin is induced via an epidural catheter. Analgesia is maintained with an infusion of Naropin, 2 mg/mL (0.2%). Clinical studies have demonstrated that infusion rates of 6-14 mL (12-28 mg) per hour provide adequate analgesia with nonprogressive motor block. With this technique a significant reduction in the need for opioids was demonstrated. Clinical experience supports the use of Naropin epidural infusions for up to 72 hours.
Route of Administration:
Parenteral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27863837
Dorsal root ganglion neurons were isolated from the SD rats and cultured in vitro. The mRNA of the CaMK II subtype in dorsal root ganglion neurons were detected by real-time PCR. As well as, the dorsal root ganglion neurons were treated with ropivacaine hydrochloride in different concentration (1mM,2mM, 3mM and 4mM) for the same exposure time of 4h, or different exposure time (0h,2h,3h,4h and 6h) at the same concentration(3mM). The changes of the mRNA expression of the CaMK II subtype were observed with real-time PCR. All subtype mRNA of the CaMK II, CaMK IIα, CaMK IIβ, CaMK II δ, CaMK IIγ, can be detected in dorsal root ganglion neurons. With the increased of the concentration and exposure time of the ropivacaine hydrochloride, all the subtype mRNA expression increased. Ropivacaine hydrochloride up-regulate the CaMK IIβ, CaMK IIδ, CaMK IIg mRNA expression with the concentration and exposure time increasing.
Substance Class |
Chemical
Created
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on
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Record UNII |
7IO5LYA57N
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Record Status |
Validated (UNII)
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WHO-VATC |
QN01BB09
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N0000007681
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N0000175976
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N0000175682
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N01BB09
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NCI_THESAURUS |
C245
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1605497
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Ropivacaine
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ROPIVACAINE
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Related Record | Type | Details | ||
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SALT/SOLVATE -> PARENT | |||
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EXCRETED UNCHANGED |
URINE
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SALT/SOLVATE -> PARENT | |||
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BINDER->LIGAND |
BINDING
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METABOLIC ENZYME -> SUBSTRATE | |||
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SALT/SOLVATE -> PARENT | |||
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METABOLIC ENZYME -> SUBSTRATE |
Related Record | Type | Details | ||
---|---|---|---|---|
|
METABOLITE -> PARENT |
2% of dose;
MINOR
URINE
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METABOLITE -> PARENT | |||
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METABOLITE -> PARENT |
Tentatively identified in the urine of some volunteers, accounting fof about 4-15% of the dose
MINOR
URINE
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METABOLITE -> PARENT |
Have a pharmacological activity in animal models less than that of ropivacaine
|
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METABOLITE -> PARENT |
MAJOR
URINE
|
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METABOLITE -> PARENT |
MINOR
URINE
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METABOLITE -> PARENT |
Have a pharmacological activity in animal models less than that of ropivacaine
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METABOLITE -> PARENT |
Have a pharmacological activity in animal models less than that of ropivacaine
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METABOLITE -> PARENT |
3% of dose
MINOR
URINE
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Related Record | Type | Details | ||
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ACTIVE MOIETY |
Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Volume of Distribution | PHARMACOKINETIC |
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INTRAVASCULAR ADMINISTRATION |
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Biological Half-life | PHARMACOKINETIC |
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INTRAVASCULAR ADMINISTRATION |
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