ROPIVACAINE MESYLATE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C17H26N2O.CH4O3S
Molecular Weight	370.507
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=YPTSIOMXZOPKAF-RSAXXLAASA-N

InChI=1S/C17H26N2O.CH4O3S/c1-4-11-19-12-6-5-10-15(19)17(20)18-16-13(2)8-7-9-14(16)3;1-5(2,3)4/h7-9,15H,4-6,10-12H2,1-3H3,(H,18,20);1H3,(H,2,3,4)/t15-;/m0./s1

HIDE SMILES / InChI

Molecular Formula	CH4O3S
Molecular Weight	96.106
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

Description
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2006/020533s014lbl.pdf | https://www.ncbi.nlm.nih.gov/pubmed/21712863

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

Approval Year

Targets

Primary Target	Pharmacology	Potency
Sodium channel protein type V alpha subunit 49 Target ID: CHEMBL1980 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25692452 \| https://www.ncbi.nlm.nih.gov/pubmed/24852501	Blocker 537	2.73 µM [IC50]
Voltage-gated potassium channel subunit Kv1.5 37 Target ID: CHEMBL4306 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9066339	Blocker 537	80.0 µM [Kd]
HERG 92 Target ID: CHEMBL240 Sources: https://www.ncbi.nlm.nih.gov/pubmed/14665560	Inhibitor 8297	20.0 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Pain 614 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2006/020533s014lbl.pdf	Primary		Approved 8429	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

C_max

Value	Dose	Analyte	Population
1.2 mg/L DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/020533s035lbl.pdf	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 DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/020533s035lbl.pdf	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 DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/020533s035lbl.pdf	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 DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/020533s035lbl.pdf	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 DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/020533s035lbl.pdf	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 DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/020533s035lbl.pdf	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

Value	Dose	Analyte	Population
1.8 mg × h/L DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/020533s035lbl.pdf	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 DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/020533s035lbl.pdf	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 DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/020533s035lbl.pdf	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 DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/020533s035lbl.pdf	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 DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/020533s035lbl.pdf	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 DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/020533s035lbl.pdf	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

T_1/2

Value	Dose	Analyte	Population
1.9 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/020533s035lbl.pdf	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 DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/020533s035lbl.pdf	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 DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/020533s035lbl.pdf	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 DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/020533s035lbl.pdf	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 DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/020533s035lbl.pdf	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 DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/020533s035lbl.pdf	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

Dose	Population	Adverse events
300 mg single, intravascular Overdose Dose: 300 mg Route: intravascular Route: single Dose: 300 mg Sources: https://pubmed.ncbi.nlm.nih.gov/17680197	healthy, 25 years n = 1 Health Status: healthy Age Group: 25 years Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/17680197	Other AEs: Convulsion... Other AEs: Convulsion (1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/17680197

AEs

AE	Significance	Dose	Population
Convulsion	1 patient	300 mg single, intravascular Overdose Dose: 300 mg Route: intravascular Route: single Dose: 300 mg Sources: https://pubmed.ncbi.nlm.nih.gov/17680197	healthy, 25 years n = 1 Health Status: healthy Age Group: 25 years Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/17680197

Sourcing

Vendor/Aggregator	ID	URL
3B Scientific (Wuhan) Corp	3B2-1091	http://www.3bsc.com/index/pro_info.php?id=54807
AA Blocks	AA003U27	https://www.aablocks.com/goods/Goods/detail?id=AA003U27
AEchem Scientific Corp., USA	AE052000	http://www.aechemsc.com/info_products/AE052000.php
AHH Chemical co.,ltd	MT-00051	http://www.ahhchemical.com/product/MT-00051.html
AHH Chemical co.,ltd	MT-58466	http://www.ahhchemical.com/product/MT-58466.html
AK Scientific, Inc. (AKSCI)	K500	http://www.aksci.com/item_detail.php?cat=K500
Acadechem	ACDS-065539	http://www.acadechemical.com/product/140238
Achemo Scientific Limited	AC-11407	http://www.achemo.com/product_view.asp?ID=1297
Achemtek	0104-017125	http://www.achemtek.com/84057-95-4
Alichem	129006366	http://www.alichem.com/en/products/84057-95-4.html
Alsachim	1323	http://www.alsachim.com/product-C2797-glo.bal-view.html
Aurora Fine Chemicals LLC	A24.074.417	http://online.aurorafinechemicals.com/info?ID=A24.074.417
AvaChem Scientific	1627B	http://www.avachem.com/productSearch.asp?1627B
BioSynth	Q-201677	https://www.biosynth.com/en/products/chemical-intermediates/basic-intermediates/products/Q-201677.html
Chem Scene	CS-0009514	http://www.chemscene.com/84057-95-4.html
ChemMol	99156732	http://www.chemmol.com/chemmol/99156732.html
Chemspace	CSSB00020642102	https://chem-space.com/CSSB00020642102
Combi-Blocks	QJ-0876	http://www.combi-blocks.com/cgi-bin/find.cgi?QJ-0876
DC Chemicals	DC9025	http://www.dcchemicals.com/product_show-Ropivacaine_base.html
Glentham Life Sciences	GP7588	http://www.glentham.com/products/product/GP7588/
Hairui	HR126818	http://www.hairuichem.com/en/product/84057-95-4.html
Lab Network	LN01310295	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN01310295
Matrix Scientific	199464	https://www.matrixscientific.com/199464.html
MedChem Express	HY-B0563	https://www.medchemexpress.com/ropivacaine.html
OChem	5072	http://www.ocheminc.com/index.php?act=psearch&pid=057R954
R&D Chemicals	46614	http://www.rdchemicals.com/chemicals.php?mode=details&mol_id=7385
Sinfoo Biotech	S049882	http://www.sinfoobiotech.com/product/1053280
Smolecule	S541801	http://www.smolecule.com/products/s541801
THE BioTek	bt-281981	https://www.thebiotek.com/product/inhibitors/bt-281981
Vitas-M Laboratory	BBL102321	http://www.request.vitasmlab.biz/index.php?option=com_search_stk&Itemid=22&stk=BBL102321&?utm_source=pubchem&utm_medium=p_search_link&utm_campaign=pubchem_search&utm_content=pubchem_slink
Vitas-M Laboratory	STL556120	http://www.request.vitasmlab.biz/index.php?option=com_search_stk&Itemid=22&stk=STL556120&?utm_source=pubchem&utm_medium=p_search_link&utm_campaign=pubchem_search&utm_content=pubchem_slink
abcr GmbH	AB455878	http://www.abcr.com/shop/en/AB455878
eNovation Chemicals	D916755	https://www.enovationchem.com/ProductDetails.asp?ProductID=D916755
iChemical	EBD867674	http://www.ichemical.com/products/84057-95-4.html?utm_source=PubChem&utm_medium=website&utm_campaign=product%20catalogs

PubMed

Title	Date	PubMed
Comparative systemic toxicity of convulsant and supraconvulsant doses of intravenous ropivacaine, bupivacaine, and lidocaine in the conscious dog.	1989 Dec	2511782
Central nervous and cardiovascular effects of i.v. infusions of ropivacaine, bupivacaine and placebo in volunteers.	1997 May	9175963
Convulsions induced by ropivacaine during interscalene brachial plexus block.	1997 Nov	9356113
Ropivacaine inhibits leukocyte rolling, adhesion and CD11b/CD18 expression.	1997 Oct	9336308
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	11133631
Cardiac resuscitation after incremental overdosage with lidocaine, bupivacaine, levobupivacaine, and ropivacaine in anesthetized dogs.	2001 Jan	11133597
Seizure induced by ropivacaine.	2001 Mar	11261529
[Comparison of ropivacaine and bupivacaine for epidural analgesia during labor].	2001 May	11412729
Systemic toxicity and resuscitation in bupivacaine-, levobupivacaine-, or ropivacaine-infused rats.	2001 Sep	11524350
Ropivacaine-induced cardiac arrest after peripheral nerve block: successful resuscitation.	2003 Dec	14639161
Pain control with low-dose alfentanil in children undergoing minor abdominal and genito-urinary surgery.	2004 Sep	15595588
Transdermal buprenorphine combined with spinal morphine and naropine for pain relief in chronic peripheral vasculopathy.	2005 Jul-Aug	16012418
Prediction of genotoxicity of chemical compounds by statistical learning methods.	2005 Jun	15962942
Postoperative analgesia after radical retropubic prostatectomy: a double-blind comparison between low thoracic epidural and patient-controlled intravenous analgesia.	2006 Oct	17006078
Long QT 1 mutation KCNQ1A344V increases local anesthetic sensitivity of the slowly activating delayed rectifier potassium current.	2006 Sep	16931984
Convulsions after ropivacaine 300 mg for brachial plexus block.	2008 Dec	18936039
Successful resuscitation after ropivacaine and lidocaine-induced ventricular arrhythmia following posterior lumbar plexus block in a child.	2008 May	18420879
Regional anesthesia for carotid endarterectomy: a comparison between ropivacaine and levobupivacaine.	2009 May	19412143
Local anesthesia with ropivacaine for patients undergoing laparoscopic cholecystectomy.	2009 May 21	19452582
Immediate intravenous lipid infusion in the successful resuscitation of ropivacaine-induced cardiac arrest after infraclavicular brachial plexus block.	2009 May-Jun	19436186
Effects of mixture of lidocaine and ropivacaine at different concentrations on the central nervous system and cardiovascular toxicity in rats.	2010 Jan 5	20137580

Patents

Sample Use Guides

In Vivo Use Guide

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

In Vitro Use Guide

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 11:09:45 UTC 2023` Edited by `admin` on `Sat Dec 16 11:09:45 UTC 2023`
Record UNII	MJO2D2C5RI
Record Status	`Validated (UNII)`
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Name

Type

Language

ROPIVACAINE MESYLATE

Common Name

English

ROPIVACAINE MESILATE

Common Name

English

Ropivacaine mesylate [WHO-DD]

Common Name

English

ROPIVACAINE METHANESULFONATE

Common Name

English

(2S)-N-(2,6-DIMETHYLPHENYL)-1-PROPYL-2-PIPERIDINECARBOXAMIDE MONOMETHANESULFONATE

Systematic Name

English

Code System Code Type Description

EVMPD

SUB130761