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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 ClH
Molecular Weight 36.461
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula H2O
Molecular Weight 18.0153
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
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
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

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 TargetPharmacologyConditionPotency
2.73 µM [IC50]
80.0 µM [Kd]
20.0 µM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
NAROPIN

Cmax

ValueDoseCo-administeredAnalytePopulation
2.4 mg/L
1493 mg other, epidural
ROPIVACAINE plasma
Homo sapiens
2.8 mg/L
2075 mg other, epidural
ROPIVACAINE plasma
Homo sapiens
1.1 mg/L
150 mg single, epidural
ROPIVACAINE plasma
Homo sapiens
1.6 mg/L
187.5 mg single, epidural
ROPIVACAINE plasma
Homo sapiens
2.3 mg/L
300 mg single, epidural
ROPIVACAINE plasma
Homo sapiens
1.2 mg/L
40 mg 1 times / day other, intravenous
ROPIVACAINE plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
135.5 mg × h/L
1493 mg other, epidural
ROPIVACAINE plasma
Homo sapiens
145 mg × h/L
2075 mg other, epidural
ROPIVACAINE plasma
Homo sapiens
7.2 mg × h/L
150 mg single, epidural
ROPIVACAINE plasma
Homo sapiens
11.3 mg × h/L
187.5 mg single, epidural
ROPIVACAINE plasma
Homo sapiens
13 mg × h/L
300 mg single, epidural
ROPIVACAINE plasma
Homo sapiens
1.8 mg × h/L
40 mg 1 times / day other, intravenous
ROPIVACAINE plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
5 h
1493 mg other, epidural
ROPIVACAINE plasma
Homo sapiens
5.7 h
2075 mg other, epidural
ROPIVACAINE plasma
Homo sapiens
5.7 h
150 mg single, epidural
ROPIVACAINE plasma
Homo sapiens
7.1 h
187.5 mg single, epidural
ROPIVACAINE plasma
Homo sapiens
6.8 h
300 mg single, epidural
ROPIVACAINE plasma
Homo sapiens
1.9 h
40 mg 1 times / day other, intravenous
ROPIVACAINE plasma
Homo sapiens

Doses

AEs

PubMed

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
Record UNII
V910P86109
Record Status Validated (UNII)
Record Version