Tìm theo
Bupivacaine
Các tên gọi khác (11 ) :
  • (+-)-Bupivacaine
  • (RS)-bupivacaine
  • 1-Butyl-2',6'-pipecoloxylidide
  • 1-Butyl-N-(2,6-dimethylphenyl)-2-piperidinecarboxamide
  • Bupivacaina
  • Bupivacaine
  • Bupivacainum
  • Carbostesin
  • dl-1-Butyl-2',6'-pipecoloxylidide
  • DL-Bupivacaine
  • Racemic bupivacaine
Thuốc gây tê
Thuốc Gốc
Small Molecule
CAS: 2180-92-9
ATC: N01BB01, N01BB10
ĐG : APP Pharmaceuticals , http://www.apppharma.com
CTHH: C18H28N2O
PTK: 288.4277
A widely used local anesthetic agent. [PubChem]
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)
InChI Key
InChIKey=LEBVLXFERQHONN-UHFFFAOYSA-N
IUPAC Name
1-butyl-N-(2,6-dimethylphenyl)piperidine-2-carboxamide
Traditional IUPAC Name
(+-)-bupivacaine
SMILES
CCCCN1CCCCC1C(=O)NC1=C(C)C=CC=C1C
Độ tan chảy
107-108 °C
Độ hòa tan
2400 mg/L (at 25 °C)
logP
3.41
logS
-3.5
pKa (strongest acidic)
13.62
pKa (Strongest Basic)
8
PSA
32.34 Å2
Refractivity
90.19 m3·mol-1
Polarizability
34.19 Å3
Rotatable Bond Count
5
H Bond Acceptor Count
2
H Bond Donor Count
1
Physiological Charge
1
Number of Rings
2
Bioavailability
1
Rule of Five
true
Ghose Filter
true
pKa
8.1
Dược Lực Học : Bupivacaine is a widely used local anesthetic agent. Bupivacaine is often administered by spinal injection prior to total hip arthroplasty. It is also commonly injected into surgical wound sites to reduce pain for up to 20 hours after surgery. In comparison to other local anesthetics it has a long duration of action. It is also the most toxic to the heart when administered in large doses. This problem has led to the use of other long-acting local anaesthetics:ropivacaine and levobupivacaine. Levobupivacaine is a derivative, specifically an enantiomer, of bupivacaine. Systemic absorption of local anesthetics produces effects on the cardiovascular and central nervous systems. At blood concentrations achieved with therapeutic doses, changes in cardiac conduction, excitability, refractoriness, contractility, and peripheral vascular resistance are minimal. However, toxic blood concentrations depress cardiac conduction and excitability, which may lead to atrioventricular block, ventricular arrhythmias and to cardiac arrest, sometimes resulting in fatalities. In addition, myocardial contractility is depressed and peripheral vasodilation occurs, leading to decreased cardiac output and arterial blood pressure. Following systemic absorption, local anesthetics can produce central nervous system stimulation, depression or both.
Cơ Chế Tác Dụng : A widely used local anesthetic agent. [PubChem] Local anesthetics such as bupivacaine 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. Bupivacaine binds to the intracellular portion of sodium channels and blocks sodium influx into nerve cells, which prevents depolarization. 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. The analgesic effects of Bupivicaine are thought to potentially be due to its binding to the prostaglandin E2 receptors, subtype EP1 (PGE2EP1), which inhibits the production of prostaglandins, thereby reducing fever, inflammation, and hyperalgesia.
Dược Động Học :
▧ Absorption :
The rate of systemic absorption of local anesthetics is dependent upon the total dose and concentration of drug administered, the route of administration, the vascularity of the administration site, and the presence or absence of epinephrine in the anesthetic solution.
▧ Protein binding :
95%
▧ Metabolism :
Amide-type local anesthetics such as bupivacaine are metabolized primarily in the liver via conjugation with glucuronic acid. The major metabolite of bupivacaine is 2,6-pipecoloxylidine, which is mainly catalyzed via cytochrome P450 3A4.
▧ Route of Elimination :
Only 6% of bupivacaine is excreted unchanged in the urine.
▧ Half Life :
2.7 hours in adults and 8.1 hours in neonates
Độc Tính : The mean seizure dosage of bupivacaine in rhesus monkeys was found to be 4.4 mg/kg with mean arterial plasma concentration of 4.5 mcg/mL. The intravenous and subcutaneous LD 50 in mice is 6 to 8 mg/kg and 38 to 54 mg/kg respectively. Recent clinical data from patients experiencing local anesthetic induced convulsions demonstrated rapid development of hypoxia, hypercarbia, and acidosis with bupivacaine within a minute of the onset of convulsions. These observations suggest that oxygen consumption and carbon dioxide production are greatly increased during local anesthetic convulsions and emphasize the importance of immediate and effective ventilation with oxygen which may avoid cardiac arrest.
Chỉ Định : 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.
Tương Tác Thuốc :
  • Conivaptan Conivaptan may increase the serum concentration of CYP3A4 Substrates such as bupivacaine. Upon completion/discontinuation of conivaptan, allow at least 7 days before initiating therapy with drugs that are CYP3A4 substrates.
Liều Lượng & Cách Dùng : Liquid - Infiltration
Solution - Epidural
Solution - Infiltration
Solution - Intraspinal
Dữ Kiện Thương Mại
Giá thị trường
Nhà Sản Xuất
  • Công ty : Sun
    Sản phẩm biệt dược : Bupivan
  • Công ty : AstraZeneca
    Sản phẩm biệt dược : Carbostesin
  • Công ty :
    Sản phẩm biệt dược : EXPAREL
  • Công ty : AstraZeneca
    Sản phẩm biệt dược : Marcain
  • Công ty : AstraZeneca
    Sản phẩm biệt dược : Marcaina
  • Sản phẩm biệt dược : Marcaine
  • Công ty : Astra Zeneca
    Sản phẩm biệt dược : Sensorcaine
  • Công ty : Astra Zeneca
    Sản phẩm biệt dược : Sensorcaine-MPF
  • Công ty : Septodont
    Sản phẩm biệt dược : Vivacaine
Đóng gói
Tài Liệu Tham Khảo Thêm
drugbank
http://www.drugbank.ca/drugs/DB00297
PubChem Compound
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=2474
PubChem Substance
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=46506768
KEGG Compound
http://www.genome.jp/dbget-bin/www_bget?cpd:C07529
ChemSpider
http://www.chemspider.com/Chemical-Structure.2380.html
National Drug Code Directory
http://www.hipaaspace.com/Medical_Billing/Coding/National.Drug.Codes/PDF/0409-1761-02
PharmGKB
http://www.pharmgkb.org/drug/PA135057240
Wikipedia
http://en.wikipedia.org/wiki/Bupivacaine
RxList
http://www.rxlist.com/cgi/generic2/bupivacaine.htm
Drugs.com
http://www.drugs.com/cdi/bupivacaine-solution.html
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