Levobupivacaine

Các tên gọi khác (6 ) :

(-)-Bupivacaine
(S)-1-Butyl-2',6'-pipecoloxylidide
(S)-Bupivacaine
L-(-)-1-Butyl-2',6'-pipecoloxylidide
L-(-)-Bupivacaine
Levobupivacaine

Thuốc gây tê

Thuốc Gốc

Small Molecule

CAS: 27262-47-1

ĐG : Ben Venue Laboratories Inc. , http://www.benvenue.com

CTHH: C₁₈H₂₈N₂O

PTK: 288.4277

Levobupivacaine is an amino-amide local anaesthetic drug belonging to the family of n-alkylsubstituted pipecoloxylidide. It is the S-enantiomer of bupivacaine. Levobupivacaine hydrochloride is commonly marketed by AstraZeneca under the trade name Chirocaine. Compared to bupivacaine, levobupivacaine is associated with less vasodilation and has a longer duration of action. It is approximately 13 per cent less potent (by molarity) than racemic bupivacaine.Levobupivacaine is indicated for local anaesthesia including infiltration, nerve block, ophthalmic, epidural and intrathecal anaesthesia in adults; and infiltration analgesia in children. Adverse drug reactions (ADRs) are rare when it is administered correctly. Most ADRs relate to administration technique (resulting in systemic exposure) or pharmacological effects of anesthesia, however allergic reactions can rarely occur. [Wikipedia]

Nhận Dạng Quốc Tế & Đặc Tính Hóa Học

Công thức hóa học

C₁₈H₂₈N₂O

Phân tử khối

288.4277

Monoisotopic mass

288.220163528

InChI

InChI=1S/C18H28N2O/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)/t16-/m0/s1

InChI Key

InChIKey=LEBVLXFERQHONN-INIZCTEOSA-N

IUPAC Name

(2S)-1-butyl-N-(2,6-dimethylphenyl)piperidine-2-carboxamide

Traditional IUPAC Name

levobupivacaine

SMILES

CCCCN1CCCC[C@H]1C(=O)NC1=C(C)C=CC=C1C

Độ hòa tan

9.77e-02 g/l

logP

3.6

logS

-3.5

pKa (strongest acidic)

13.62

pKa (Strongest Basic)

PSA

32.34 Å²

Refractivity

90.19 m³·mol^-1

Polarizability

34.45 Å³

Rotatable Bond Count

H Bond Acceptor Count

H Bond Donor Count

Physiological Charge

Number of Rings

Bioavailability

Rule of Five

true

Ghose Filter

true

pKa

8.1

Dược Lực Học : Levobupivacaine, a local anesthetic agent, is indicated for the production of local or regional anesthesia or analgesia for surgery, for oral surgery procedures, for diagnostic and therapeutic procedures, and for obstetrical procedures.

Cơ Chế Tác Dụng : Levobupivacaine is an amino-amide local anaesthetic drug belonging to the family of n-alkylsubstituted pipecoloxylidide. It is the S-enantiomer of bupivacaine. Levobupivacaine hydrochloride is commonly marketed by AstraZeneca under the trade name Chirocaine. Compared to bupivacaine, levobupivacaine is associated with less vasodilation and has a longer duration of action. It is approximately 13 per cent less potent (by molarity) than racemic bupivacaine.Levobupivacaine is indicated for local anaesthesia including infiltration, nerve block, ophthalmic, epidural and intrathecal anaesthesia in adults; and infiltration analgesia in children. Adverse drug reactions (ADRs) are rare when it is administered correctly. Most ADRs relate to administration technique (resulting in systemic exposure) or pharmacological effects of anesthesia, however allergic reactions can rarely occur. [Wikipedia] Local anesthetics such as Levobupivacaine block the generation and the conduction of nerve impulses, presumably by increasing the threshold for electrical excitation in the nerve, by slowing the 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. Specifically, the drug binds to the intracellular portion of sodium channels and blocks sodium influx into nerve cells, which prevents depolarization.

Dược Động Học :

▧ Absorption :
The plasma concentration of levobupivacaine following therapeutic administration depends on dose and also on route of administration, because absorption from the site of administration is affected by the vascularity of the tissue. Peak levels in blood were reached approximately 30 minutes after epidural administration, and doses up to 150 mg resulted in mean C_max levels of up to 1.2 µg/mL.
▧ Volume of Distribution :
66.91 ±18.23 L [after intravenous administration of 40 mg in healthy volunteers]
▧ Protein binding :
>97%
▧ Metabolism :
Levobupivacaine is extensively metabolized with no unchanged levobupivacaine detected in urine or feces. In vitro studies using [14 C] levobupivacaine showed that CYP3A4 isoform and CYP1A2 isoform mediate the metabolism of levobupivacaine to desbutyl levobupivacaine and 3-hydroxy levobupivacaine, respectively. In vivo, the 3-hydroxy levobupivacaine appears to undergo further transformation to glucuronide and sulfate conjugates. Metabolic inversion of levobupivacaine to R(+)-bupivacaine was not evident both in vitro and in vivo.
▧ Route of Elimination :
Following intravenous administration, recovery of the radiolabelled dose of levobupivacaine was essentially quantitative with a mean total of about 95% being recovered in urine and feces in 48 hours. Of this 95%, about 71% was in urine while 24% was in feces.
▧ Half Life :
3.3 hours
▧ Clearance :
39.06 ±13.29 L/h [after intravenous administration of 40 mg in healthy volunteers]

Độc Tính : LD50: 5.1mg/kg in rabbit, intravenous; 18mg/kg in rabbit, oral; 207mg/kg in rabbit, parenteral; 63mg/kg in rat, subcutaneous (Archives Internationales de Pharmacodynamie et de Therapie. Vol. 200, Pg. 359, 1972.) Levobupivacaine appears to cause less myocardial depression than both bupivacaine and ropivacaine, despite being in higher concentrations.

Chỉ Định : For the production of local or regional anesthesia for surgery and obstetrics, and for post-operative pain management

Liều Lượng & Cách Dùng : Solution - Parenteral

Dữ Kiện Thương Mại

Nhà Sản Xuất

Công ty : Abbott Laboratories

Sản phẩm biệt dược : Chirocaine

Đóng gói

Công ty : Ben Venue Laboratories Inc.

Website : http://www.benvenue.com
Công ty : Purdue Pharma LP

Website : http://www.purduepharma.com

Tài Liệu Tham Khảo Thêm

drugbank

http://www.drugbank.ca/drugs/DB01002

PubChem Compound

http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=92253

PubChem Substance

http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=46505295

KEGG Compound

http://www.genome.jp/dbget-bin/www_bget?cpd:C07887

ChemSpider

http://www.chemspider.com/Chemical-Structure.83289.html

PharmGKB

http://www.pharmgkb.org/drug/PA164754741

Wikipedia

http://en.wikipedia.org/wiki/Levobupivacaine

RxList

http://www.rxlist.com/cgi/generic2/levobupivacaine.htm

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