Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C18H28N2O.ClH |
Molecular Weight | 324.889 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.CCCCN1CCCC[C@H]1C(=O)NC2=C(C)C=CC=C2C
InChI
InChIKey=SIEYLFHKZGLBNX-NTISSMGPSA-N
InChI=1S/C18H28N2O.ClH/c1-4-5-12-20-13-7-6-11-16(20)18(21)19-17-14(2)9-8-10-15(17)3;/h8-10,16H,4-7,11-13H2,1-3H3,(H,19,21);1H/t16-;/m0./s1
Molecular Formula | C18H28N2O |
Molecular Weight | 288.4277 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
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 |
DescriptionCurator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/18728849
Curator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/18728849
Levobupivacaine (CHIROCAINE®) is a (S)-enantiomer of bupivacaine and it is related chemically and pharmacologically to the amino amide class of local anesthetics. Local anesthetics block the generation and the conduction of nerve impulses by increasing the threshold for electrical excitation in the nerve, by slowing propagation of the nerve impulse, and by reducing the rate of rise of the action potential. In general, the progression of anesthesia is related to the diameter, myelination, and conduction velocity of affected nerve fibers. Clinically, the order of loss of nerve function is as follows: 1) pain, 2) temperature, 3) touch, 4) proprioception and 5) skeletal muscle tone. Levobupivacaine (CHIROCAINE®) is a safer alternative for regional anesthesia than bupivacaine. It demonstrated less affinity and strength of depressant effects onto myocardial and central nervous vital centers in pharmacodynamic studies, and a superior pharmacokinetic profile.
CNS Activity
Originator
Sources: https://www.ncbi.nlm.nih.gov/pubmed/18728849
Curator's Comment: Darwin Discovery Ltd., distributed by Purdue Pharma L.P.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL3509 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24249993 |
4.4 µM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | CHIROCAINE Approved UseChirocaine is indicated for the production of local or regional anesthesia for surgery and obstetrics, and for post-operative pain management. Launch Date1999 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
0.582 μg/mL |
75 mg single, epidural dose: 75 mg route of administration: Epidural experiment type: SINGLE co-administered: |
LEVOBUPIVACAINE plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
|
0.811 μg/mL |
112.5 mg single, epidural dose: 112.5 mg route of administration: Epidural experiment type: SINGLE co-administered: |
LEVOBUPIVACAINE plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
|
0.474 μg/mL |
1 mg/kg bw single, brachial plexus block dose: 1 mg/kg bw route of administration: Brachial plexus block experiment type: SINGLE co-administered: |
LEVOBUPIVACAINE plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
|
0.961 μg/mL |
2 mg/kg bw single, brachial plexus block dose: 2 mg/kg bw route of administration: Brachial plexus block experiment type: SINGLE co-administered: |
LEVOBUPIVACAINE plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
3.561 μg × h/mL |
75 mg single, epidural dose: 75 mg route of administration: Epidural experiment type: SINGLE co-administered: |
LEVOBUPIVACAINE plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
|
4.93 μg × h/mL |
112.5 mg single, epidural dose: 112.5 mg route of administration: Epidural experiment type: SINGLE co-administered: |
LEVOBUPIVACAINE plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
|
2.999 μg × h/mL |
1 mg/kg bw single, brachial plexus block dose: 1 mg/kg bw route of administration: Brachial plexus block experiment type: SINGLE co-administered: |
LEVOBUPIVACAINE plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
|
5.311 μg × h/mL |
2 mg/kg bw single, brachial plexus block dose: 2 mg/kg bw route of administration: Brachial plexus block experiment type: SINGLE co-administered: |
LEVOBUPIVACAINE plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
3% |
75 mg single, epidural dose: 75 mg route of administration: Epidural experiment type: SINGLE co-administered: |
LEVOBUPIVACAINE plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
|
3% |
112.5 mg single, epidural dose: 112.5 mg route of administration: Epidural experiment type: SINGLE co-administered: |
LEVOBUPIVACAINE plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
|
3% |
1 mg/kg bw single, brachial plexus block dose: 1 mg/kg bw route of administration: Brachial plexus block experiment type: SINGLE co-administered: |
LEVOBUPIVACAINE plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
|
3% |
2 mg/kg bw single, brachial plexus block dose: 2 mg/kg bw route of administration: Brachial plexus block experiment type: SINGLE co-administered: |
LEVOBUPIVACAINE plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
142.5 mg single, intravenous Dose: 142.5 mg Route: intravenous Route: single Dose: 142.5 mg Sources: |
unhealthy, 77 years |
|
2 mg/kg single, caudal epidural Dose: 2 mg/kg Route: caudal epidural Route: single Dose: 2 mg/kg Sources: |
unhealthy, < 3 months Health Status: unhealthy Age Group: < 3 months Sex: M+F Sources: |
|
1.75 mg/kg single, subcutaneous Dose: 1.75 mg/kg Route: subcutaneous Route: single Dose: 1.75 mg/kg Sources: |
unhealthy, >66 years Health Status: unhealthy Age Group: >66 years Sex: M+F Sources: |
PubMed
Title | Date | PubMed |
---|---|---|
Safer labelling of levobupivacaine. | 2002 Aug |
|
Levobupivacaina, bupivacaina racemica e ropivacaina nel blocco del plesso brachiale. | 2002 Jul-Aug |
|
Does local anesthetic stereoselectivity or structure predict myocardial depression in anesthetized canines? | 2002 Sep-Oct |
|
The place of ropivacaine in anesthesia. | 2003 |
|
Seizure after levobupivacaine for interscalene brachial plexus block. | 2003 Apr |
|
A response to 'Convulsions following axillary brachial plexus blockade with levobupivacaine', Pirotta D, Sprigge J, Anaesthesia 2002; 57: 1187-9. | 2003 Apr |
|
Epidural levobupivacaine, ropivacaine and bupivacaine in combination with sufentanil in early labour: a randomized trial. | 2003 Aug |
|
A comparison of three different concentrations of levobupivacaine for caudal block in children. | 2003 Aug |
|
Comparison of different concentrations of levobupivacaine for post-operative epidural analgesia. | 2003 Aug |
|
Levobupivacaine versus racemic bupivacaine in spinal anaesthesia for urological surgery. | 2003 Dec |
|
A prospective, randomized, double-blind comparison of epidural levobupivacaine 0.5% with epidural ropivacaine 0.75% for lower limb procedures. | 2003 Dec |
|
A randomized sequential allocation study to determine the minimum effective analgesic concentration of levobupivacaine and ropivacaine in patients receiving epidural analgesia for labor. | 2003 Dec |
|
Relative analgesic potencies of levobupivacaine and ropivacaine for epidural analgesia in labor. | 2003 Dec |
|
Preoperative interscalene block for elective shoulder surgery: loss of benefit over early postoperative block after patient discharge to home. | 2003 Dec |
|
Preincisional local infiltration of levobupivacaine vs ropivacaine for pain control after laparoscopic cholecystectomy. | 2003 Dec |
|
Efficacy and safety of caudal injection of levobupivacaine, 0.25%, in children under 2 years of age undergoing inguinal hernia repair, circumcision or orchidopexy. | 2003 Feb |
|
[The choice of drugs for caudal anaesthesia in children. An overview]. | 2003 Jan |
|
Accidental intravascular injection of levobupivacaine and lidocaine during the transarterial approach to the axillary brachial plexus. | 2003 Jan |
|
Interscalene brachial plexus anesthesia and analgesia for open shoulder surgery: a randomized, double-blinded comparison between levobupivacaine and ropivacaine. | 2003 Jan |
|
Central nervous system and cardiac effects from long-acting amide local anesthetic toxicity in the intact animal model. | 2003 Jan-Feb |
|
The relative toxicity of amitriptyline, bupivacaine, and levobupivacaine administered as rapid infusions in rats. | 2003 Jul |
|
Levobupivacaine versus ropivacaine for sciatic nerve block in the rat. | 2003 Jul-Aug |
|
Convulsions following axillary brachial plexus blockade with levobupivacaine. | 2003 Jun |
|
Intraoperative epidural anesthesia and postoperative analgesia with levobupivacaine for major orthopedic surgery: a double-blind, randomized comparison of racemic bupivacaine and ropivacaine. | 2003 Mar |
|
New local anesthetics. Are they worth the cost? | 2003 Mar |
|
The efficacy and safety of 0.75% levobupivacaine vs 0.75% bupivacaine for peribulbar anaesthesia. | 2003 Mar |
|
Infragluteal-parabiceps sciatic nerve block: an evaluation of a novel approach using a single-injection technique. | 2003 Mar |
|
Continuous epidural infusion of large concentration/small volume versus small concentration/large volume of levobupivacaine for postoperative analgesia. | 2003 Mar |
|
Safe dose of levobupivacaine (Chirocaine) in caudal analgesia in children. | 2003 Mar |
|
Urinary bladder scanning after day-case arthroscopy under spinal anaesthesia: comparison between lidocaine, ropivacaine, and levobupivacaine. | 2003 Mar |
|
Central nervous system toxicity following the administration of levobupivacaine for lumbar plexus block: A report of two cases. | 2003 Mar-Apr |
|
[Prevention of cardiovascular accidents during locoregional anesthesia]. | 2003 May |
|
Stability of sufentanil and levobupivacaine solutions and a mixture in a 0.9% sodium chloride infusion stored in polypropylene syringes. | 2003 May |
|
Efficacy, safety, and pharmacokinetics of levobupivacaine with and without fentanyl after continuous epidural infusion in children: a multicenter trial. | 2003 Nov |
|
Comparison of the effects of intrathecal ropivacaine, levobupivacaine, and bupivacaine for Caesarean section. | 2003 Nov |
|
The relative motor blocking potencies of bupivacaine and levobupivacaine in labor. | 2003 Nov |
|
Perioperative thoracic epidural analgesia in aortic surgery: role of levobupivacaine. | 2003 Oct |
|
Levobupivacaine 0.25% compared with ropivacaine 0.25% by the caudal route in children. | 2003 Oct |
|
Pulmonary uptake of ropivacaine and levobupivacaine in rabbits. | 2003 Sep |
|
Onset time, quality of blockade, and duration of three-in-one blocks with levobupivacaine and bupivacaine. | 2003 Sep |
|
Severe phantom leg pain in an amputee after lumbar plexus block. | 2003 Sep-Oct |
|
A comparison of levobupivacaine 0.5% and racemic bupivacaine 0.5% for extradural anesthesia for caesarean section. | 2003 Sep-Oct |
|
Comparison of patient-controlled epidural bolus administration of 0.1% ropivacaine and 0.1% levobupivacaine, both with 0.0002% fentanyl, for analgesia during labour. | 2004 Feb |
|
A comparison of duration of analgesia of intrathecal 2.5 mg of bupivacaine, ropivacaine, and levobupivacaine in combined spinal epidural analgesia for patients in labor. | 2004 Jan |
|
Levobupivacaine for pediatric spinal anesthesia. | 2004 Jan |
|
Local anaesthetic sensitivities of cloned HERG channels from human heart: comparison with HERG/MiRP1 and HERG/MiRP1 T8A. | 2004 Jan |
|
Long-term stability of sufentanil citrate with levobupivacaine hydrochloride in 0.9% sodium chloride infusion PVC bags at 4 degrees C. | 2004 Jul |
|
[Levobupivacaine in obstetric analgesia and anaesthesia. Where is its place?]. | 2004 Jul |
|
Evidence that intravenous vasopressors can affect rostral spread of spinal anesthesia in pregnancy. | 2004 Jul |
|
Intraoperative and postoperative analgesia with subcutaneous ring block of the penis with levobupivacaine for circumcision in children. | 2004 Jun |
Sample Use Guides
Surgical anaesthesia: epidural for surgery 10-20 mL (50-150 mg), epidural for cesarean section 20-30 mL (100-150 mg), peripheral nerve 30 mL or 0.4 mL/kg (75-150 mg or 1-2 mg/kg), ophthalmic 5-15 mL (37.5-112.5 mg), local infiltration 60 mL (150 mg).
Pain management: epidural for labor analgesia 10-20 mL (25-50 mg), epidural for post-operative pain 4-10 mL/h (5-25 mg/h).
Route of Administration:
Intravenous
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/16418020
The antagonist activity of levobupivacaine was tested at the human nicotinic acetylcholine (nACh), murine N-methyl-d-aspartate (NMDA), murine gamma-aminobutyric acid(A) (GABA(A)), and human 5-hydroxytryptamine(3A) (5-HT(3A)) receptors expressed in Xenopus oocytes using a 2-voltage clamp technique. The IC50 of levobupivacaine were 950 uM, 65 uM and 85 uM for NMDA, 5-HT(3A), and nACh receptors, respectively. Inhibition of the GABA(A) receptor required concentrations in excess of 10 mM.
Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 18:12:21 GMT 2025
by
admin
on
Mon Mar 31 18:12:21 GMT 2025
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Record UNII |
J998RDZ51I
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Record Status |
Validated (UNII)
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Record Version |
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-
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NCI_THESAURUS |
C245
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CHEMBL1201193
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DTXSID9046071
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J998RDZ51I
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SUB02904MIG
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KK-63
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C61805
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100000090489
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259454
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m2769
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27262-48-2
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DBSALT000834
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117965
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31772
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RACEMATE -> ENANTIOMER |
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PARENT -> SALT/SOLVATE |
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ACTIVE MOIETY |
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