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

Molecular Formula H2O
Molecular Weight 18.0153
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
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
Postoperative extradural infusions in children: preliminary data from a comparison of bupivacaine/diamorphine with plain ropivacaine.
1999
Studies on sulfation of synthesized metabolites from the local anesthetics ropivacaine and lidocaine using human cloned sulfotransferases.
1999 Sep
[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
Cardiac arrest after interscalene brachial plexus block with ropivacaine and lidocaine.
2003 Aug
Cardiac arrest after injection of ropivacaine for posterior lumbar plexus blockade.
2003 Dec
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
Prediction of genotoxicity of chemical compounds by statistical learning methods.
2005 Jun
Successful use of a 20% lipid emulsion to resuscitate a patient after a presumed bupivacaine-related cardiac arrest.
2006 Jul
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
Successful resuscitation after ropivacaine and lidocaine-induced ventricular arrhythmia following posterior lumbar plexus block in a child.
2008 May
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
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 Fri Dec 15 15:35:36 GMT 2023
Edited
by admin
on Fri Dec 15 15:35:36 GMT 2023
Record UNII
V910P86109
Record Status Validated (UNII)
Record Version
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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
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PRIMARY
CHEBI
60803
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PRIMARY
PUBCHEM
6918111
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PRIMARY
NCI_THESAURUS
C52198
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
34954
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
236539
Created by admin on Fri Dec 15 15:35:36 GMT 2023 , Edited by admin on Fri Dec 15 15:35:36 GMT 2023
ALTERNATIVE
EVMPD
SUB22590
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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
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
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
Related Record Type Details
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BASIS OF STRENGTH->SUBSTANCE
ASSAY (TITRATION)
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BASIS OF STRENGTH->SUBSTANCE
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ANHYDROUS->SOLVATE
PARENT -> SALT/SOLVATE
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CHROMATOGRAPHIC PURITY (HPLC/UV)
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IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
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IMPURITY -> PARENT
Capillary electrophoresis
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ACTIVE MOIETY