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
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
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

AUC

ValueDoseCo-administeredAnalytePopulation
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

T1/2

ValueDoseCo-administeredAnalytePopulation
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

Doses

DosePopulationAdverse 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...
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
n = 1
Health Status: healthy
Age Group: 25 years
Sex: F
Population Size: 1
Sources:
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
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
Postoperative extradural infusions in children: preliminary data from a comparison of bupivacaine/diamorphine with plain ropivacaine.
1999
Axillary brachial plexus block with ropivacaine 7.5 mg/ml. A comparative study with bupivacaine 5 mg/ml.
1999 Sep
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
Acute toxicity of local anesthetic ropivacaine and mepivacaine during a combined lumbar plexus and sciatic block for hip surgery.
2002
Ropivacaine-induced convulsion immediately after epidural administration--a case report.
2002 Mar
Ropivacaine-induced cardiac arrest after peripheral nerve block: successful resuscitation.
2003 Dec
Lipid emulsion infusion rescues dogs from bupivacaine-induced cardiac toxicity.
2003 May-Jun
[Pain control with epidural anesthesia for uterine artery embolization].
2004 Apr
Can ropivacaine and levobupivacaine be used as test doses during regional anesthesia?
2004 Apr
Effects of clonidine pre-treatment on bupivacaine and ropivacaine cardiotoxicity in rats.
2004 Mar
Prediction of genotoxicity of chemical compounds by statistical learning methods.
2005 Jun
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
[Transient neurological symptoms in puerperas after epidural analgesia during labor].
2007 Nov-Dec
Convulsions after ropivacaine 300 mg for brachial plexus block.
2008 Dec
[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
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
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.
Name Type Language
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
TLC-590
Code 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
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NDF-RT N0000007681
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NDF-RT N0000175976
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NDF-RT N0000175682
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WHO-ATC N01BB09
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NCI_THESAURUS C245
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Code System Code Type Description
MERCK INDEX
m9659
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PRIMARY Merck Index
RS_ITEM_NUM
1605497
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PRIMARY
EVMPD
SUB10382MIG
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PRIMARY
DAILYMED
7IO5LYA57N
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PRIMARY
EPA CompTox
DTXSID4040187
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PRIMARY
RXCUI
35780
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PRIMARY RxNorm
DRUG BANK
DB00296
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PRIMARY
LACTMED
Ropivacaine
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PRIMARY
INN
5376
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PRIMARY
CHEBI
8890
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PRIMARY
IUPHAR
7602
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PRIMARY
ChEMBL
CHEMBL1077896
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PRIMARY
CAS
84057-95-4
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PRIMARY
FDA UNII
7IO5LYA57N
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PRIMARY
MESH
C037663
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PRIMARY
NCI_THESAURUS
C61932
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PRIMARY
DRUG CENTRAL
2403
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PRIMARY
PUBCHEM
175805
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PRIMARY
SMS_ID
100000084379
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PRIMARY
WIKIPEDIA
ROPIVACAINE
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PRIMARY