U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
Structure of ROPIVACAINE

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

HIDE SMILES / InChI

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

Originator

Curator's Comment: refrence retrieved from https://www.ncbi.nlm.nih.gov/pubmed/8777115

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
NAROPIN

Approved Use

Ropivacaine 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 Date

1996
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
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
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
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
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
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
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
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
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
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
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
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
Doses

Doses

DosePopulationAdverse events​
300 mg single, intravascular
Overdose
Dose: 300 mg
Route: intravascular
Route: single
Dose: 300 mg
Sources:
healthy, 25 years
Health Status: healthy
Age Group: 25 years
Sex: F
Sources:
Other AEs: Convulsion...
Other AEs:
Convulsion (1 patient)
Sources:
AEs

AEs

AESignificanceDosePopulation
Convulsion 1 patient
300 mg single, intravascular
Overdose
Dose: 300 mg
Route: intravascular
Route: single
Dose: 300 mg
Sources:
healthy, 25 years
Health Status: healthy
Age Group: 25 years
Sex: F
Sources:
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Apoptosis and mitochondrial dysfunction in human chondrocytes following exposure to lidocaine, bupivacaine, and ropivacaine.
2010-03
Effects of mixture of lidocaine and ropivacaine at different concentrations on the central nervous system and cardiovascular toxicity in rats.
2010-01-05
Repeated intrathecal administration of ropivacaine causes neurotoxicity in rats.
2009-11
Convulsions associated with a low plasma level of local anaesthetics.
2009-11
Lipid emulsion improves recovery from bupivacaine-induced cardiac arrest, but not from ropivacaine- or mepivacaine-induced cardiac arrest.
2009-10
The addition of fentanyl to 1.5 mg/ml ropivacaine has no advantage for paediatric epidural analgesia.
2009-09
Transient unilateral Horner's syndrome after epidural ropivacaine in a dog.
2009-07
Local anesthesia with ropivacaine for patients undergoing laparoscopic cholecystectomy.
2009-05-21
Immediate intravenous lipid infusion in the successful resuscitation of ropivacaine-induced cardiac arrest after infraclavicular brachial plexus block.
2009-05-14
Regional anesthesia for carotid endarterectomy: a comparison between ropivacaine and levobupivacaine.
2009-05
[Grand mal convulsion after an interscalene block with ropivacaine].
2009-04
Convulsions after ropivacaine 300 mg for brachial plexus block.
2008-12
I.V. ropivacaine compared with lidocaine for the treatment of tinnitus.
2008-08
Successful resuscitation after ropivacaine and lidocaine-induced ventricular arrhythmia following posterior lumbar plexus block in a child.
2008-05
[Transient neurological symptoms in puerperas after epidural analgesia during labor].
2008-03-11
Ropivacaine-induced cardiac arrest.
2007-06
Successful resuscitation of an ASA 3 patient following ropivacaine-induced cardiac arrest.
2006-12
Preexisting subclinical neuropathy as a risk factor for nerve injury after continuous ropivacaine administration through a femoral nerve catheter.
2006-11
Postoperative analgesia after radical retropubic prostatectomy: a double-blind comparison between low thoracic epidural and patient-controlled intravenous analgesia.
2006-10
Long QT 1 mutation KCNQ1A344V increases local anesthetic sensitivity of the slowly activating delayed rectifier potassium current.
2006-09
The effect of epidural sufentanil in ropivacaine on urinary retention in patients undergoing gastrectomy.
2006-09
Successful resuscitation of a patient with ropivacaine-induced asystole after axillary plexus block using lipid infusion.
2006-08
Successful use of a 20% lipid emulsion to resuscitate a patient after a presumed bupivacaine-related cardiac arrest.
2006-07
Minimum local anaesthetic dose (MLAD) of intrathecal levobupivacaine and ropivacaine for Caesarean section.
2006-02
Lipid emulsion to treat overdose of local anaesthetic: the gift of the glob.
2006-02
Transdermal buprenorphine combined with spinal morphine and naropine for pain relief in chronic peripheral vasculopathy.
2005-07-14
Prediction of genotoxicity of chemical compounds by statistical learning methods.
2005-06
[Convulsions induced by ropivacaine after brachial plexus block].
2004-11
Ectopic expression of clusterin/apolipoprotein J or Bcl-2 decreases the sensitivity of HaCaT cells to toxic effects of ropivacaine.
2004-10
Pain control with low-dose alfentanil in children undergoing minor abdominal and genito-urinary surgery.
2004-09
Ropivacaine-induced asystole: "never again" rather than "here we go again".
2004-08
[Pain control with epidural anesthesia for uterine artery embolization].
2004-04
Can ropivacaine and levobupivacaine be used as test doses during regional anesthesia?
2004-04
Effects of clonidine pre-treatment on bupivacaine and ropivacaine cardiotoxicity in rats.
2004-03
Cardiac arrest after injection of ropivacaine for posterior lumbar plexus blockade.
2003-12
Ropivacaine-induced cardiac arrest after peripheral nerve block: successful resuscitation.
2003-12
Successful resuscitation after ropivacaine-induced ventricular fibrillation.
2003-09
Cardiac arrest after interscalene brachial plexus block with ropivacaine and lidocaine.
2003-08
Lipid emulsion infusion rescues dogs from bupivacaine-induced cardiac toxicity.
2003-05-29
Loss of consciousness from epidural sufentanil for labour analgesia.
2003-05
[Epidural anesthesia with ropivacaine vs. bupivacaine in continuous perfusion for the treatment of labor pains].
2003-02
[Convulsions induced by ropivacaine after midhumeral block].
2002-10
Tachycardia and convulsions induced by accidental intravascular ropivacaine injection during sciatic block.
2002-05
[Hyperbaric subarachnoid ropivacaine in ambulatory surgery: comparative study with hyperbaric bupivacaine].
2002-02
Acute toxicity of local anesthetic ropivacaine and mepivacaine during a combined lumbar plexus and sciatic block for hip surgery.
2002
Convulsions induced by ropivacaine during interscalene brachial plexus block.
1997-11
Ropivacaine inhibits leukocyte rolling, adhesion and CD11b/CD18 expression.
1997-10
Central nervous and cardiovascular effects of i.v. infusions of ropivacaine, bupivacaine and placebo in volunteers.
1997-05
Treatment of acute systemic toxicity after the rapid intravenous injection of ropivacaine and bupivacaine in the conscious dog.
1991-10
Comparative systemic toxicity of convulsant and supraconvulsant doses of intravenous ropivacaine, bupivacaine, and lidocaine in the conscious dog.
1989-12
Patents

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
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
by admin
on Wed Apr 02 06:56:20 GMT 2025
Edited
by admin
on Wed Apr 02 06:56:20 GMT 2025
Record UNII
7IO5LYA57N
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TLC-590
Preferred Name English
ROPIVACAINE
INN   MI   USP-RS   VANDF   WHO-DD  
INN  
Official Name English
ROPIVACAINE [VANDF]
Common Name English
TLC590
Code English
ROPIVACAINE [USP-RS]
Common Name English
(S)-(-)-1-PROPYLPIPERIDINE-2-CARBOXYLIC ACID (2,6-DIMETHYLPHENYL)AMIDE
Systematic Name English
ROPIVACAINE [MI]
Common Name English
Ropivacaine [WHO-DD]
Common Name English
(S)-(-)-1-PROPYL-2',6'-PIPECOLOXYLIDINE
Common Name English
ropivacaine [INN]
Common Name English
ROPIVICAINE
Common Name English
Classification Tree Code System Code
WHO-VATC QN01BB09
Created by admin on Wed Apr 02 06:56:20 GMT 2025 , Edited by admin on Wed Apr 02 06:56:20 GMT 2025
NDF-RT N0000007681
Created by admin on Wed Apr 02 06:56:20 GMT 2025 , Edited by admin on Wed Apr 02 06:56:20 GMT 2025
NDF-RT N0000175976
Created by admin on Wed Apr 02 06:56:20 GMT 2025 , Edited by admin on Wed Apr 02 06:56:20 GMT 2025
NDF-RT N0000175682
Created by admin on Wed Apr 02 06:56:20 GMT 2025 , Edited by admin on Wed Apr 02 06:56:20 GMT 2025
WHO-ATC N01BB09
Created by admin on Wed Apr 02 06:56:20 GMT 2025 , Edited by admin on Wed Apr 02 06:56:20 GMT 2025
NCI_THESAURUS C245
Created by admin on Wed Apr 02 06:56:20 GMT 2025 , Edited by admin on Wed Apr 02 06:56:20 GMT 2025
Code System Code Type Description
MERCK INDEX
m9659
Created by admin on Wed Apr 02 06:56:20 GMT 2025 , Edited by admin on Wed Apr 02 06:56:20 GMT 2025
PRIMARY Merck Index
RS_ITEM_NUM
1605497
Created by admin on Wed Apr 02 06:56:20 GMT 2025 , Edited by admin on Wed Apr 02 06:56:20 GMT 2025
PRIMARY
EVMPD
SUB10382MIG
Created by admin on Wed Apr 02 06:56:20 GMT 2025 , Edited by admin on Wed Apr 02 06:56:20 GMT 2025
PRIMARY
DAILYMED
7IO5LYA57N
Created by admin on Wed Apr 02 06:56:20 GMT 2025 , Edited by admin on Wed Apr 02 06:56:20 GMT 2025
PRIMARY
EPA CompTox
DTXSID4040187
Created by admin on Wed Apr 02 06:56:20 GMT 2025 , Edited by admin on Wed Apr 02 06:56:20 GMT 2025
PRIMARY
RXCUI
35780
Created by admin on Wed Apr 02 06:56:20 GMT 2025 , Edited by admin on Wed Apr 02 06:56:20 GMT 2025
PRIMARY RxNorm
DRUG BANK
DB00296
Created by admin on Wed Apr 02 06:56:20 GMT 2025 , Edited by admin on Wed Apr 02 06:56:20 GMT 2025
PRIMARY
LACTMED
Ropivacaine
Created by admin on Wed Apr 02 06:56:20 GMT 2025 , Edited by admin on Wed Apr 02 06:56:20 GMT 2025
PRIMARY
INN
5376
Created by admin on Wed Apr 02 06:56:20 GMT 2025 , Edited by admin on Wed Apr 02 06:56:20 GMT 2025
PRIMARY
CHEBI
8890
Created by admin on Wed Apr 02 06:56:20 GMT 2025 , Edited by admin on Wed Apr 02 06:56:20 GMT 2025
PRIMARY
IUPHAR
7602
Created by admin on Wed Apr 02 06:56:20 GMT 2025 , Edited by admin on Wed Apr 02 06:56:20 GMT 2025
PRIMARY
ChEMBL
CHEMBL1077896
Created by admin on Wed Apr 02 06:56:20 GMT 2025 , Edited by admin on Wed Apr 02 06:56:20 GMT 2025
PRIMARY
CAS
84057-95-4
Created by admin on Wed Apr 02 06:56:20 GMT 2025 , Edited by admin on Wed Apr 02 06:56:20 GMT 2025
PRIMARY
FDA UNII
7IO5LYA57N
Created by admin on Wed Apr 02 06:56:20 GMT 2025 , Edited by admin on Wed Apr 02 06:56:20 GMT 2025
PRIMARY
MESH
C037663
Created by admin on Wed Apr 02 06:56:20 GMT 2025 , Edited by admin on Wed Apr 02 06:56:20 GMT 2025
PRIMARY
NCI_THESAURUS
C61932
Created by admin on Wed Apr 02 06:56:20 GMT 2025 , Edited by admin on Wed Apr 02 06:56:20 GMT 2025
PRIMARY
DRUG CENTRAL
2403
Created by admin on Wed Apr 02 06:56:20 GMT 2025 , Edited by admin on Wed Apr 02 06:56:20 GMT 2025
PRIMARY
PUBCHEM
175805
Created by admin on Wed Apr 02 06:56:20 GMT 2025 , Edited by admin on Wed Apr 02 06:56:20 GMT 2025
PRIMARY
SMS_ID
100000084379
Created by admin on Wed Apr 02 06:56:20 GMT 2025 , Edited by admin on Wed Apr 02 06:56:20 GMT 2025
PRIMARY
WIKIPEDIA
ROPIVACAINE
Created by admin on Wed Apr 02 06:56:20 GMT 2025 , Edited by admin on Wed Apr 02 06:56:20 GMT 2025
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
EXCRETED UNCHANGED
URINE
SALT/SOLVATE -> PARENT
BINDER->LIGAND
BINDING
METABOLIC ENZYME -> SUBSTRATE
SALT/SOLVATE -> PARENT
METABOLIC ENZYME -> SUBSTRATE
Related Record Type Details
METABOLITE -> PARENT
2% of dose;
MINOR
URINE
METABOLITE -> PARENT
METABOLITE -> PARENT
Tentatively identified in the urine of some volunteers, accounting fof about 4-15% of the dose
MINOR
URINE
METABOLITE -> PARENT
Have a pharmacological activity in animal models less than that of ropivacaine
METABOLITE -> PARENT
MAJOR
URINE
METABOLITE -> PARENT
MINOR
URINE
METABOLITE -> PARENT
Have a pharmacological activity in animal models less than that of ropivacaine
METABOLITE -> PARENT
Have a pharmacological activity in animal models less than that of ropivacaine
METABOLITE -> PARENT
3% of dose
MINOR
URINE
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Volume of Distribution PHARMACOKINETIC INTRAVASCULAR ADMINISTRATION

Biological Half-life PHARMACOKINETIC INTRAVASCULAR ADMINISTRATION