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

Details

Stereochemistry ABSOLUTE
Molecular Formula C17H26N2O.ClH
Molecular Weight 310.862
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ROPIVACAINE HYDROCHLORIDE ANHYDROUS

SMILES

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

InChI

InChIKey=NDNSIBYYUOEUSV-RSAXXLAASA-N
InChI=1S/C17H26N2O.ClH/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/t15-;/m0./s1

HIDE SMILES / InChI

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

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
Convulsions induced by ropivacaine during interscalene brachial plexus block.
1997 Nov
Ropivacaine inhibits leukocyte rolling, adhesion and CD11b/CD18 expression.
1997 Oct
Postoperative extradural infusions in children: preliminary data from a comparison of bupivacaine/diamorphine with plain ropivacaine.
1999
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
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
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
[Hyperbaric subarachnoid ropivacaine in ambulatory surgery: comparative study with hyperbaric bupivacaine].
2002 Feb
Ropivacaine-induced convulsion immediately after epidural administration--a case report.
2002 Mar
Tachycardia and convulsions induced by accidental intravascular ropivacaine injection during sciatic block.
2002 May
[Convulsions induced by ropivacaine after midhumeral block].
2002 Oct
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
Loss of consciousness from epidural sufentanil for labour analgesia.
2003 May
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
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
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
[Transient neurological symptoms in puerperas after epidural analgesia during labor].
2007 Nov-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
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 Dec 15 18:55:03 UTC 2023
Edited
by admin
on Fri Dec 15 18:55:03 UTC 2023
Record UNII
35504LBE2T
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ROPIVACAINE HYDROCHLORIDE ANHYDROUS
Common Name English
(S)-(-)-1-PROPYL-2',6'-PIPECOLOXYLIDINE HYDROCHLORIDE
Common Name English
ROPIVACAINE HYDROCHLORIDE [MART.]
Common Name English
(S)-(-)-1-PROPYLPIPERIDINE-2-CARBOXYLIC ACID (2,6-DIMETHYLPHENYL)AMIDE HYDROCHLORIDE
Systematic Name English
Ropivacaine hydrochloride [WHO-DD]
Common Name English
ROPIVACAINE HYDROCHLORIDE [MI]
Common Name English
Code System Code Type Description
DRUG BANK
DBSALT002892
Created by admin on Fri Dec 15 18:55:03 UTC 2023 , Edited by admin on Fri Dec 15 18:55:03 UTC 2023
PRIMARY
RXCUI
2198974
Created by admin on Fri Dec 15 18:55:03 UTC 2023 , Edited by admin on Fri Dec 15 18:55:03 UTC 2023
PRIMARY
EPA CompTox
DTXSID2048379
Created by admin on Fri Dec 15 18:55:03 UTC 2023 , Edited by admin on Fri Dec 15 18:55:03 UTC 2023
PRIMARY
CAS
98717-15-8
Created by admin on Fri Dec 15 18:55:03 UTC 2023 , Edited by admin on Fri Dec 15 18:55:03 UTC 2023
PRIMARY
EVMPD
SUB23569
Created by admin on Fri Dec 15 18:55:03 UTC 2023 , Edited by admin on Fri Dec 15 18:55:03 UTC 2023
PRIMARY
FDA UNII
35504LBE2T
Created by admin on Fri Dec 15 18:55:03 UTC 2023 , Edited by admin on Fri Dec 15 18:55:03 UTC 2023
PRIMARY
MERCK INDEX
m9659
Created by admin on Fri Dec 15 18:55:03 UTC 2023 , Edited by admin on Fri Dec 15 18:55:03 UTC 2023
PRIMARY Merck Index
PUBCHEM
175804
Created by admin on Fri Dec 15 18:55:03 UTC 2023 , Edited by admin on Fri Dec 15 18:55:03 UTC 2023
PRIMARY
SMS_ID
100000084942
Created by admin on Fri Dec 15 18:55:03 UTC 2023 , Edited by admin on Fri Dec 15 18:55:03 UTC 2023
PRIMARY
DAILYMED
35504LBE2T
Created by admin on Fri Dec 15 18:55:03 UTC 2023 , Edited by admin on Fri Dec 15 18:55:03 UTC 2023
PRIMARY
Related Record Type Details
SOLVATE->ANHYDROUS
PARENT -> SALT/SOLVATE
SUBSTANCE->BASIS OF STRENGTH
Related Record Type Details
ACTIVE MOIETY