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

Details

Stereochemistry ABSOLUTE
Molecular Formula C17H26N2O.ClH.H2O
Molecular Weight 328.877
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ROPIVACAINE HYDROCHLORIDE

SMILES

O.Cl.CCCN1CCCC[C@H]1C(=O)NC2=C(C)C=CC=C2C

InChI

InChIKey=VSHFRHVKMYGBJL-CKUXDGONSA-N
InChI=1S/C17H26N2O.ClH.H2O/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);1H;1H2/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
Treatment of acute systemic toxicity after the rapid intravenous injection of ropivacaine and bupivacaine in the conscious dog.
1991 Oct
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
Tachycardia and convulsions induced by accidental intravascular ropivacaine injection during sciatic block.
2002 May
Successful resuscitation after ropivacaine-induced ventricular fibrillation.
2003 Sep
Ropivacaine-induced asystole: "never again" rather than "here we go again".
2004 Aug
Effects of clonidine pre-treatment on bupivacaine and ropivacaine cardiotoxicity in rats.
2004 Mar
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
Preexisting subclinical neuropathy as a risk factor for nerve injury after continuous ropivacaine administration through a femoral nerve catheter.
2006 Nov
Postoperative analgesia after radical retropubic prostatectomy: a double-blind comparison between low thoracic epidural and patient-controlled intravenous analgesia.
2006 Oct
Ropivacaine-induced cardiac arrest.
2007 Jun
I.V. ropivacaine compared with lidocaine for the treatment of tinnitus.
2008 Aug
Convulsions after ropivacaine 300 mg for brachial plexus block.
2008 Dec
[Grand mal convulsion after an interscalene block with ropivacaine].
2009 Apr
Transient unilateral Horner's syndrome after epidural ropivacaine in a dog.
2009 Jul
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
Immediate intravenous lipid infusion in the successful resuscitation of ropivacaine-induced cardiac arrest after infraclavicular brachial plexus block.
2009 May-Jun
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
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 HYDROCHLORIDE
ORANGE BOOK   USP   USP-RS   VANDF  
Common Name English
ROPIVACAINE HYDROCHLORIDE MONOHYDRATE [EP IMPURITY]
Common Name English
(S)-(-)-1-PROPYLPIPERIDINE-2-CARBOXYLIC ACID (2,6-DIMETHYLPHENYL)AMIDE HYDROCHLORIDE MONOHYDRATE
Systematic Name English
ROPIVACAINE HYDROCHLORIDE MONOHYDRATE [MI]
Common Name English
ROPIVACAINE HYDROCHLORIDE HYDRATE
JAN  
Common Name English
ROPIVACAINE HCL
Common Name English
ROPIVACAINE HYDROCHLORIDE MONOHYDRATE [EP MONOGRAPH]
Common Name English
(S)-(-)-1-PROPYL-2',6'-PIPECOLOXYLIDINE HYDROCHLORIDE MONOHYDRATE
Common Name English
ROPIVACAINE HYDROCHLORIDE [VANDF]
Common Name English
ROPIVACAINE HYDROCHLORIDE MONOHYDRATE
EP   MI   ORANGE BOOK   WHO-DD  
Common Name English
Ropivacaine hydrochloride monohydrate [WHO-DD]
Common Name English
ROPIVACAINE HYDROCHLORIDE MONOHYDRATE [ORANGE BOOK]
Common Name English
NAROPIN
Brand Name English
ROPIVACAINE HYDROCHLORIDE [USP MONOGRAPH]
Common Name English
ROPIVACAINE HYDROCHLORIDE HYDRATE [JAN]
Common Name English
ROPIVACAINE HYDROCHLORIDE [ORANGE BOOK]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C245
Created by admin on Fri Dec 15 15:35:36 GMT 2023 , Edited by admin on Fri Dec 15 15:35:36 GMT 2023
Code System Code Type Description
RS_ITEM_NUM
1605500
Created by admin on Fri Dec 15 15:35:36 GMT 2023 , Edited by admin on Fri Dec 15 15:35:36 GMT 2023
PRIMARY
DAILYMED
V910P86109
Created by admin on Fri Dec 15 15:35:36 GMT 2023 , Edited by admin on Fri Dec 15 15:35:36 GMT 2023
PRIMARY
CHEBI
60803
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PRIMARY
PUBCHEM
6918111
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PRIMARY
NCI_THESAURUS
C52198
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PRIMARY
CHEBI
34954
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PRIMARY
RXCUI
236539
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ALTERNATIVE
EVMPD
SUB22590
Created by admin on Fri Dec 15 15:35:36 GMT 2023 , Edited by admin on Fri Dec 15 15:35:36 GMT 2023
PRIMARY
SMS_ID
100000090606
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PRIMARY
FDA UNII
V910P86109
Created by admin on Fri Dec 15 15:35:36 GMT 2023 , Edited by admin on Fri Dec 15 15:35:36 GMT 2023
PRIMARY
EPA CompTox
DTXSID80927544
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PRIMARY
CAS
132112-35-7
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PRIMARY
ChEMBL
CHEMBL1077896
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PRIMARY
EVMPD
SUB04264MIG
Created by admin on Fri Dec 15 15:35:36 GMT 2023 , Edited by admin on Fri Dec 15 15:35:36 GMT 2023
PRIMARY
RXCUI
1298851
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PRIMARY
DRUG BANK
DBSALT000902
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PRIMARY
MERCK INDEX
m9659
Created by admin on Fri Dec 15 15:35:36 GMT 2023 , Edited by admin on Fri Dec 15 15:35:36 GMT 2023
PRIMARY Merck Index