Bupivacaine hydrochloride monohydrate

Chemodex
Product Code: CDX-B0326
Supplier: Chemodex
CodeSizePrice
CDX-B0326-G0011 g£65.00
Quantity:
CDX-B0326-G0055 g£96.00
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Prices exclude any Taxes / VAT

Overview

Regulatory Status: RUO
Shipping:
Ambient
Storage:
+20°C

Images

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Chemical Structure

Chemical Structure

Further Information

Alternate Names/Synonyms:
1-Butyl-N-(2,6-dimethylphenyl)-2-piperidinecarboxamide; 1-Butyl-2',6'-pipecoloxylidide
Appearance:
White to off-white powder.
CAS:
73360-54-0
Class:
6.1
EClass:
32160000
Form (Short):
liquid
GHS Symbol:
GHS06
Handling Advice:
Protect from light and moisture.
Hazards:
H300+H310+H330
InChi:
InChI=1S/C18H28N2O.ClH.H2O/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;1H2
InChiKey:
HUCIWBPMHXGLFM-UHFFFAOYSA-N
Long Description:
Chemical. CAS: 73360-54-0. Formula: C18H28N2O . HCl . H2O. MW: 288.4. 36.5 . 18.0. Synthetic. Bupivacaine is an amino amide local anesthetic that decreases current amplitude and inhibits whole cell K+ currents in Ca2+-activated K+ channels and N-type voltage-gated (KCNA and KCNC) K+ channels. Bupivacaine also inhibits voltage-gated Na+ channels and tandem pore domain (TASK-2/KCNK-5) K+ channels. The compound is cytotoxic at high concentrations inducing apoptosis and/or necrosis by interference with the mitochondrial energy transduction. Shown to inhibit aerobic ATP synthesis by (i) uncoupling of the oxidative phosphorylation (OXPHOS) and (ii) inhibition of the complex I of the respiratory. Other mechanisms include inhibition of the carnitine-acylcarnitine translocase or activation of the mitochondrial permeability transition pore (MPTP). 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. It is employed as cAMP production inhibitor, it acts as a surfactant molecule possessing both hydrophilic and lipophilic properties, adrenergic antagonist and cholinesterase inhibitor.
MDL:
MFCD00941462
Molecular Formula:
C18H28N2O . HCl . H2O
Molecular Weight:
288.4. 36.5 . 18.0
Package Type:
Vial
PG:
II
Precautions:
P260, P264, P280, P284, P301+P310, P302+P350
Product Description:
Bupivacaine is an amino amide local anesthetic that decreases current amplitude and inhibits whole cell K+ currents in Ca2+-activated K+ channels and N-type voltage-gated (KCNA and KCNC) K+ channels. Bupivacaine also inhibits voltage-gated Na+ channels and tandem pore domain (TASK-2/KCNK-5) K+ channels. The compound is cytotoxic at high concentrations inducing apoptosis and/or necrosis by interference with the mitochondrial energy transduction. Shown to inhibit aerobic ATP synthesis by (i) uncoupling of the oxidative phosphorylation (OXPHOS) and (ii) inhibition of the complex I of the respiratory. Other mechanisms include inhibition of the carnitine-acylcarnitine translocase or activation of the mitochondrial permeability transition pore (MPTP). 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. It is employed as cAMP production inhibitor, it acts as a surfactant molecule possessing both hydrophilic and lipophilic properties, adrenergic antagonist and cholinesterase inhibitor.
Purity:
>98% (T)
Signal word:
Danger
SMILES:
CCCCN1CCCCC1C(NC2=C(C)C=CC=C2C)=O.Cl.O
Solubility Chemicals:
Soluble in water (10mg/ml), DMSO (20mg/ml) or ethanol (20mg/ml). Slightly soluble in chloroform or acetone.
Source / Host:
Synthetic
Transportation:
Excepted Quantity
UN Nummer:
2811
UNSPSC Category:
Biochemical Reagents
UNSPSC Number:
12352200
Use & Stability:
Stable for at least 2 years after receipt when stored at RT.

References

(1) F. Sztark, et al.; Anesthesiology 88, 1340 (1998) | (2) G.L. Weinberg, et al.; Anesthesiology 92, 523 (2000) | (3) C.W. Hoenemann, et al.; Anesth. Analg. 93, 628 (2001) | (4) W. Irwin, et al.; J. Biol. Chem. 277, 12221 (2002) | (5) W.H. Kluge, et al.; Scand. J. Clin. Lab Invest. 62, 495 (2002) | (6) A. Unami, et al.; J. Toxicol. Sci. 28, 77 (2003) | (7) C.H. Kindler, et al.; J. Pharmacol. Exp. Ther. 306, 84 (2003) | (8) J. Nilsson, et al.; Biophys. J. 95, 5138 (2008) | (9) O. Cela, et al. ; Mitochondrion 10, 487 (2010) | (10) J. Lu, et al.; Eur. J. Pharmacol. 657, 51 (2011) | (11) M. Harato, et al.; BMC Neurosci. 13, 149 (2012) | (12) P. Martin, et al.; Channels 6, 174 (2012) | (13) M.A. Paganelli & G.K. Popescu; J. Neurosci. 35, 831 (2015)