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 Date9.3381119E11 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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 |
|
0.582 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 |
|
0.961 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 |
---|---|---|---|---|
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 |
|
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 |
|
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% |
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% |
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% |
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 n = 1 Health Status: unhealthy Age Group: 77 years Sex: F Population Size: 1 Sources: |
|
2 mg/kg single, caudal epidural Dose: 2 mg/kg Route: caudal epidural Route: single Dose: 2 mg/kg Sources: |
unhealthy, < 3 months n = 22 Health Status: unhealthy Age Group: < 3 months Sex: M+F Population Size: 22 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 n = 12 Health Status: unhealthy Age Group: >66 years Sex: M+F Population Size: 12 Sources: |
PubMed
Title | Date | PubMed |
---|---|---|
Levobupivacaine. | 2001 Apr |
|
Cardiac resuscitation after incremental overdosage with lidocaine, bupivacaine, levobupivacaine, and ropivacaine in anesthetized dogs. | 2001 Jan |
|
Does prior administration of enoxaparin influence the effects of levobupivacaine on blood clotting? Assessment using the Thrombelastograph. | 2001 Jun |
|
[Peripheral nerve block. An overview of new developments in an old technique]. | 2001 May |
|
Systemic toxicity of levobupivacaine, bupivacaine, and ropivacaine during continuous intravenous infusion to nonpregnant and pregnant ewes. | 2001 Nov |
|
[Levobupivacaine in obstetric analgesia and anaesthesia]. | 2001 Sep |
|
A comparison of epidural levobupivacaine 0.5% with or without epinephrine for lumbar spine surgery. | 2001 Sep |
|
Systemic toxicity and resuscitation in bupivacaine-, levobupivacaine-, or ropivacaine-infused rats. | 2001 Sep |
|
Local anaesthesia in elective inguinal hernia repair: a randomised, double-blind study comparing the efficacy of levobupivacaine with racemic bupivacaine. | 2002 |
|
Cardiac and CNS toxicity of levobupivacaine: strengths of evidence for advantage over bupivacaine. | 2002 |
|
Effects of levobupivacaine, ropivacaine and bupivacaine on HERG channels: stereoselective bupivacaine block. | 2002 Dec |
|
Safety and efficacy of levobupivacaine for postoperative pain relief after the surgical removal of impacted third molars: a comparison with lignocaine and adrenaline. | 2002 Dec |
|
Levobupivacaine versus racemic bupivacaine for spinal anesthesia. | 2002 Jan |
|
Levobupivacaina, bupivacaina racemica e ropivacaina nel blocco del plesso brachiale. | 2002 Jul-Aug |
|
A comparative study of the safety and efficacy of 0.5% levobupivacaine and 0.5% bupivacaine for epidural anesthesia in subjects undergoing elective caesarean section. | 2002 Mar |
|
Clinical properties of levobupivacaine or racemic bupivacaine for sciatic nerve block. | 2002 Mar |
|
Periosteal infusion of bupivacaine/morphine post sternal fracture: a new analgesic technique. | 2002 May-Jun |
|
The place of ropivacaine in anesthesia. | 2003 |
|
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 |
|
A prospective, randomized, double-blind comparison of epidural levobupivacaine 0.5% with epidural ropivacaine 0.75% for lower limb procedures. | 2003 Dec |
|
Preincisional local infiltration of levobupivacaine vs ropivacaine for pain control after laparoscopic cholecystectomy. | 2003 Dec |
|
The relative toxicity of amitriptyline, bupivacaine, and levobupivacaine administered as rapid infusions in rats. | 2003 Jul |
|
Convulsions following axillary brachial plexus blockade with levobupivacaine. | 2003 Jun |
|
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 |
|
Urinary bladder scanning after day-case arthroscopy under spinal anaesthesia: comparison between lidocaine, ropivacaine, and levobupivacaine. | 2003 Mar |
|
[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 |
|
Comparison of the effects of intrathecal ropivacaine, levobupivacaine, and bupivacaine for Caesarean section. | 2003 Nov |
|
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 |
|
Can ropivacaine and levobupivacaine be used as test doses during regional anesthesia? | 2004 Apr |
|
Pharmacokinetics of levobupivacaine 0.25% following caudal administration in children under 2 years of age. | 2004 Feb |
|
Levobupivacaine for pediatric spinal anesthesia. | 2004 Jan |
|
Epidural test dose with levobupivacaine and ropivacaine: determination of ED(50) motor block after spinal administration. | 2004 Jun |
|
High-dose bupivacaine, levobupivacaine and ropivacaine in axillary brachial plexus block. | 2004 May |
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
Fri Dec 16 18:32:12 UTC 2022
by
admin
on
Fri Dec 16 18:32:12 UTC 2022
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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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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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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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