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2180-92-9 molecular structure
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1-butyl-N-(2,6-dimethylphenyl)piperidine-2-carboxamide

ChemBase ID: 182
Molecular Formular: C18H28N2O
Molecular Mass: 288.42772
Monoisotopic Mass: 288.22016353
SMILES and InChIs

SMILES:
O=C(Nc1c(cccc1C)C)C1N(CCCC1)CCCC
Canonical SMILES:
CCCCN1CCCCC1C(=O)Nc1c(C)cccc1C
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)
InChIKey:
LEBVLXFERQHONN-UHFFFAOYSA-N

Cite this record

CBID:182 http://www.chembase.cn/molecule-182.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
1-butyl-N-(2,6-dimethylphenyl)piperidine-2-carboxamide
IUPAC Traditional name
1-butyl-N-(2,6-dimethylphenyl)piperidine-2-carboxamide
bupivacaine
Brand Name
Anekain
Bupivan
Carbostesin
Chirocaine
Marcaina
Marcaine
Marcaine HCL
Marcaine Spinal
Sensorcaine
Sensorcaine-MPF
Sensorcaine-MPF Spinal
Transdur-Bupivacaine
DepoBupivacaine
Synonyms
DL-Bupivacaine
cBupivacaine
Bupivacaina [INN-Spanish]
Bupivacaine HCL
Bupivacaine HCL KIT
Bupivacainum [INN-Latin]
(+-)-Bupivacaine
Bloqueina
LAC-43
DUR-843
bupivacaine
Bupivacaine
Carbostesin
Duracaine
Marcaine
Meaverin-ultra
Narcain
Sensorcaine
Svedocain
Bupivacaine
1-Butyl-N-(2,6-dimethylphenyl)piperidine-2-carboxamide
CAS Number
2180-92-9
PubChem SID
46506768
160963645
PubChem CID
2474

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 13.623539  H Acceptors
H Donor LogD (pH = 5.5) 2.0522962 
LogD (pH = 7.4) 3.8159845  Log P 4.5155187 
Molar Refractivity 90.1933 cm3 Polarizability 34.286346 Å3
Polar Surface Area 32.34 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P 3.31  LOG S -3.47 
Solubility (Water) 9.77e-02 g/l 

PROPERTIES

PROPERTIES

Physical Property Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
2400 mg/L expand Show data source
Hydrophobicity(logP)
3.6 expand Show data source
Mechanism of Action
Blocks the generation and the conduction of nerve impulses, expand Show data source
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 expand Show data source
Purity
95+% expand Show data source
97% expand Show data source
Application(s)
Local anaesthetic expand Show data source

DETAILS

DETAILS

DrugBank DrugBank
DrugBank - DB00297 external link
Item Information
Drug Groups approved; investigational
Description A widely used local anesthetic agent. [PubChem]
Indication 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.
Pharmacology 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.
Toxicity 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.
Affected Organisms
Humans and other mammals
Biotransformation 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.
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.
Half Life 2.7 hours in adults and 8.1 hours in neonates
Protein Binding 95%
Elimination Only 6% of bupivacaine is excreted unchanged in the urine.
References
[Link]
Rosenblatt MA, Abel M, Fischer GW, Itzkovich CJ, Eisenkraft JB: Successful use of a 20% lipid emulsion to resuscitate a patient after a presumed bupivacaine-related cardiac arrest. Anesthesiology. 2006 Jul;105(1):217-8. [Pubmed]
Picard J, Meek T: Lipid emulsion to treat overdose of local anaesthetic: the gift of the glob. Anaesthesia. 2006 Feb;61(2):107-9. [Pubmed]
External Links
Wikipedia
RxList
Drugs.com

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
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  • • U.K. Pat., 1969, Sterling, 1 166 802; CA, 72, 43429, (synth)
  • • Tullar, B.F., J. Med. Chem., 1971, 14, 891, (resoln)
  • • Moore, D.C. et al., Acta Anaesthesiol. Scand., 1977, 21, 109, (rev)
  • • Wiklund, L., Acta Anaesthesiol. Scand., Suppl., 1978, 70, 83, (rev, pharmacol)
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  • • Jones, G.P. et al., J.C.S. Perkin 2, 1987, 415, (struct, conformn)
  • • Slot, H.J.B. et al., Acta Cryst. B, 1990, 46, 842, (cryst struct)
  • • Wilson, T.D., Anal. Profiles Drug Subst., 1990, 19, 59, (rev)
  • • Csregh, I., Acta Cryst. C, 1992, 48, 1794, (cryst struct)
  • • Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 1003
  • • McClellan, K.J. et al., Drugs, 1998, 56, 355-363, (rev)
  • • Sorbera, L.A. et al., Drugs of the Future, 1998, 23, 838-842, (rev)
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  • • Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, BOO000; BOO250; BSI250; BOO500
  • •  Link
  • • Rosenblatt MA, Abel M, Fischer GW, Itzkovich CJ, Eisenkraft JB: Successful use of a 20% lipid emulsion to resuscitate a patient after a presumed bupivacaine-related cardiac arrest. Anesthesiology. 2006 Jul;105(1):217-8. Pubmed
  • • Picard J, Meek T: Lipid emulsion to treat overdose of local anaesthetic: the gift of the glob. Anaesthesia. 2006 Feb;61(2):107-9. Pubmed
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