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
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
Convulsions induced by ropivacaine during interscalene brachial plexus block.
1997 Nov
Ropivacaine inhibits leukocyte rolling, adhesion and CD11b/CD18 expression.
1997 Oct
A multicentre trial of ropivacaine 7.5 mg x ml(-1) vs bupivacaine 5 mg x ml(-1) for supra clavicular brachial plexus anesthesia.
1999 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
Seizure induced by ropivacaine.
2001 Mar
[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
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
Postoperative analgesia after radical retropubic prostatectomy: a double-blind comparison between low thoracic epidural and patient-controlled intravenous analgesia.
2006 Oct
I.V. ropivacaine compared with lidocaine for the treatment of tinnitus.
2008 Aug
Successful resuscitation after ropivacaine and lidocaine-induced ventricular arrhythmia following posterior lumbar plexus block in a child.
2008 May
[Grand mal convulsion after an interscalene block with ropivacaine].
2009 Apr
Regional anesthesia for carotid endarterectomy: a comparison between ropivacaine and levobupivacaine.
2009 May
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
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 Sat Dec 16 15:56:19 GMT 2023
Edited
by admin
on Sat Dec 16 15:56:19 GMT 2023
Record UNII
7IO5LYA57N
Record Status Validated (UNII)
Record Version
  • Download
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
Created by admin on Sat Dec 16 15:56:21 GMT 2023 , Edited by admin on Sat Dec 16 15:56:21 GMT 2023
NDF-RT N0000007681
Created by admin on Sat Dec 16 15:56:21 GMT 2023 , Edited by admin on Sat Dec 16 15:56:21 GMT 2023
NDF-RT N0000175976
Created by admin on Sat Dec 16 15:56:21 GMT 2023 , Edited by admin on Sat Dec 16 15:56:21 GMT 2023
NDF-RT N0000175682
Created by admin on Sat Dec 16 15:56:21 GMT 2023 , Edited by admin on Sat Dec 16 15:56:21 GMT 2023
WHO-ATC N01BB09
Created by admin on Sat Dec 16 15:56:21 GMT 2023 , Edited by admin on Sat Dec 16 15:56:21 GMT 2023
NCI_THESAURUS C245
Created by admin on Sat Dec 16 15:56:21 GMT 2023 , Edited by admin on Sat Dec 16 15:56:21 GMT 2023
Code System Code Type Description
MERCK INDEX
m9659
Created by admin on Sat Dec 16 15:56:21 GMT 2023 , Edited by admin on Sat Dec 16 15:56:21 GMT 2023
PRIMARY Merck Index
RS_ITEM_NUM
1605497
Created by admin on Sat Dec 16 15:56:21 GMT 2023 , Edited by admin on Sat Dec 16 15:56:21 GMT 2023
PRIMARY
EVMPD
SUB10382MIG
Created by admin on Sat Dec 16 15:56:21 GMT 2023 , Edited by admin on Sat Dec 16 15:56:21 GMT 2023
PRIMARY
DAILYMED
7IO5LYA57N
Created by admin on Sat Dec 16 15:56:21 GMT 2023 , Edited by admin on Sat Dec 16 15:56:21 GMT 2023
PRIMARY
EPA CompTox
DTXSID4040187
Created by admin on Sat Dec 16 15:56:21 GMT 2023 , Edited by admin on Sat Dec 16 15:56:21 GMT 2023
PRIMARY
RXCUI
35780
Created by admin on Sat Dec 16 15:56:21 GMT 2023 , Edited by admin on Sat Dec 16 15:56:21 GMT 2023
PRIMARY RxNorm
DRUG BANK
DB00296
Created by admin on Sat Dec 16 15:56:21 GMT 2023 , Edited by admin on Sat Dec 16 15:56:21 GMT 2023
PRIMARY
LACTMED
Ropivacaine
Created by admin on Sat Dec 16 15:56:21 GMT 2023 , Edited by admin on Sat Dec 16 15:56:21 GMT 2023
PRIMARY
INN
5376
Created by admin on Sat Dec 16 15:56:21 GMT 2023 , Edited by admin on Sat Dec 16 15:56:21 GMT 2023
PRIMARY
CHEBI
8890
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PRIMARY
IUPHAR
7602
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PRIMARY
ChEMBL
CHEMBL1077896
Created by admin on Sat Dec 16 15:56:21 GMT 2023 , Edited by admin on Sat Dec 16 15:56:21 GMT 2023
PRIMARY
CAS
84057-95-4
Created by admin on Sat Dec 16 15:56:21 GMT 2023 , Edited by admin on Sat Dec 16 15:56:21 GMT 2023
PRIMARY
FDA UNII
7IO5LYA57N
Created by admin on Sat Dec 16 15:56:21 GMT 2023 , Edited by admin on Sat Dec 16 15:56:21 GMT 2023
PRIMARY
MESH
C037663
Created by admin on Sat Dec 16 15:56:21 GMT 2023 , Edited by admin on Sat Dec 16 15:56:21 GMT 2023
PRIMARY
NCI_THESAURUS
C61932
Created by admin on Sat Dec 16 15:56:21 GMT 2023 , Edited by admin on Sat Dec 16 15:56:21 GMT 2023
PRIMARY
DRUG CENTRAL
2403
Created by admin on Sat Dec 16 15:56:21 GMT 2023 , Edited by admin on Sat Dec 16 15:56:21 GMT 2023
PRIMARY
PUBCHEM
175805
Created by admin on Sat Dec 16 15:56:21 GMT 2023 , Edited by admin on Sat Dec 16 15:56:21 GMT 2023
PRIMARY
SMS_ID
100000084379
Created by admin on Sat Dec 16 15:56:21 GMT 2023 , Edited by admin on Sat Dec 16 15:56:21 GMT 2023
PRIMARY
WIKIPEDIA
ROPIVACAINE
Created by admin on Sat Dec 16 15:56:21 GMT 2023 , Edited by admin on Sat Dec 16 15:56:21 GMT 2023
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