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Details

Stereochemistry ABSOLUTE
Molecular Formula C17H26N2O
Molecular Weight 274.4018
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ROPIVACAINE

SMILES

CCCN1CCCC[C@@]1([H])C(=Nc2c(C)cccc2C)O

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 274.4018
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

8.4352323E11
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
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
[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
Acute toxicity of local anesthetic ropivacaine and mepivacaine during a combined lumbar plexus and sciatic block for hip surgery.
2002
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
[Epidural anesthesia with ropivacaine vs. bupivacaine in continuous perfusion for the treatment of labor pains].
2003 Feb
Lipid emulsion infusion rescues dogs from bupivacaine-induced cardiac toxicity.
2003 May-Jun
Successful resuscitation after ropivacaine-induced ventricular fibrillation.
2003 Sep
[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
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
[Convulsions induced by ropivacaine after brachial plexus block].
2004 Nov
Ectopic expression of clusterin/apolipoprotein J or Bcl-2 decreases the sensitivity of HaCaT cells to toxic effects of ropivacaine.
2004 Oct
Pain control with low-dose alfentanil in children undergoing minor abdominal and genito-urinary surgery.
2004 Sep
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
Successful resuscitation of a patient with ropivacaine-induced asystole after axillary plexus block using lipid infusion.
2006 Aug
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
Successful use of a 20% lipid emulsion to resuscitate a patient after a presumed bupivacaine-related cardiac arrest.
2006 Jul
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
Long QT 1 mutation KCNQ1A344V increases local anesthetic sensitivity of the slowly activating delayed rectifier potassium current.
2006 Sep
The effect of epidural sufentanil in ropivacaine on urinary retention in patients undergoing gastrectomy.
2006 Sep
Ropivacaine-induced cardiac arrest.
2007 Jun
[Transient neurological symptoms in puerperas after epidural analgesia during labor].
2007 Nov-Dec
I.V. ropivacaine compared with lidocaine for the treatment of tinnitus.
2008 Aug
Convulsions after ropivacaine 300 mg for brachial plexus block.
2008 Dec
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
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.
Substance Class Chemical
Created
by admin
on Fri Jun 25 22:46:07 UTC 2021
Edited
by admin
on Fri Jun 25 22:46:07 UTC 2021
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 Fri Jun 25 22:46:07 UTC 2021 , Edited by admin on Fri Jun 25 22:46:07 UTC 2021
NDF-RT N0000007681
Created by admin on Fri Jun 25 22:46:07 UTC 2021 , Edited by admin on Fri Jun 25 22:46:07 UTC 2021
NDF-RT N0000175976
Created by admin on Fri Jun 25 22:46:07 UTC 2021 , Edited by admin on Fri Jun 25 22:46:07 UTC 2021
NDF-RT N0000175682
Created by admin on Fri Jun 25 22:46:07 UTC 2021 , Edited by admin on Fri Jun 25 22:46:07 UTC 2021
WHO-ATC N01BB09
Created by admin on Fri Jun 25 22:46:07 UTC 2021 , Edited by admin on Fri Jun 25 22:46:07 UTC 2021
NCI_THESAURUS C245
Created by admin on Fri Jun 25 22:46:07 UTC 2021 , Edited by admin on Fri Jun 25 22:46:07 UTC 2021
Code System Code Type Description
MERCK INDEX
M9659
Created by admin on Fri Jun 25 22:46:07 UTC 2021 , Edited by admin on Fri Jun 25 22:46:07 UTC 2021
PRIMARY Merck Index
EVMPD
SUB10382MIG
Created by admin on Fri Jun 25 22:46:07 UTC 2021 , Edited by admin on Fri Jun 25 22:46:07 UTC 2021
PRIMARY
EPA CompTox
84057-95-4
Created by admin on Fri Jun 25 22:46:07 UTC 2021 , Edited by admin on Fri Jun 25 22:46:07 UTC 2021
PRIMARY
RXCUI
35780
Created by admin on Fri Jun 25 22:46:07 UTC 2021 , Edited by admin on Fri Jun 25 22:46:07 UTC 2021
PRIMARY RxNorm
DRUG BANK
DB00296
Created by admin on Fri Jun 25 22:46:07 UTC 2021 , Edited by admin on Fri Jun 25 22:46:07 UTC 2021
PRIMARY
USP_CATALOG
1605497
Created by admin on Fri Jun 25 22:46:07 UTC 2021 , Edited by admin on Fri Jun 25 22:46:07 UTC 2021
PRIMARY USP-RS
LACTMED
Ropivacaine
Created by admin on Fri Jun 25 22:46:07 UTC 2021 , Edited by admin on Fri Jun 25 22:46:07 UTC 2021
PRIMARY
INN
5376
Created by admin on Fri Jun 25 22:46:07 UTC 2021 , Edited by admin on Fri Jun 25 22:46:07 UTC 2021
PRIMARY
IUPHAR
7602
Created by admin on Fri Jun 25 22:46:07 UTC 2021 , Edited by admin on Fri Jun 25 22:46:07 UTC 2021
PRIMARY
ChEMBL
CHEMBL1077896
Created by admin on Fri Jun 25 22:46:07 UTC 2021 , Edited by admin on Fri Jun 25 22:46:07 UTC 2021
PRIMARY
CAS
84057-95-4
Created by admin on Fri Jun 25 22:46:07 UTC 2021 , Edited by admin on Fri Jun 25 22:46:07 UTC 2021
PRIMARY
FDA UNII
7IO5LYA57N
Created by admin on Fri Jun 25 22:46:07 UTC 2021 , Edited by admin on Fri Jun 25 22:46:07 UTC 2021
PRIMARY
MESH
C037663
Created by admin on Fri Jun 25 22:46:07 UTC 2021 , Edited by admin on Fri Jun 25 22:46:07 UTC 2021
PRIMARY
NCI_THESAURUS
C61932
Created by admin on Fri Jun 25 22:46:07 UTC 2021 , Edited by admin on Fri Jun 25 22:46:07 UTC 2021
PRIMARY
DRUG CENTRAL
2403
Created by admin on Fri Jun 25 22:46:07 UTC 2021 , Edited by admin on Fri Jun 25 22:46:07 UTC 2021
PRIMARY
PUBCHEM
175805
Created by admin on Fri Jun 25 22:46:07 UTC 2021 , Edited by admin on Fri Jun 25 22:46:07 UTC 2021
PRIMARY
WIKIPEDIA
ROPIVACAINE
Created by admin on Fri Jun 25 22:46:07 UTC 2021 , Edited by admin on Fri Jun 25 22:46:07 UTC 2021
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