CAS 27262-47-1|Levobupivacaine

Introduction：Basic information about CAS 27262-47-1|Levobupivacaine, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
Common NameLevobupivacaine
CAS Number27262-47-1Molecular Weight288.428
Density1.0±0.1 g/cm3Boiling Point423.4±45.0 °C at 760 mmHg
Molecular FormulaC18H28N2OMelting Point254ºC (dec.)(lit.)
MSDS/Flash Point209.9±28.7 °C

Names

Namelevobupivacaine
SynonymMore Synonyms

Levobupivacaine BiologicalActivity

DescriptionLevobupivacaine ((S)-(-)-Bupivacaine) is a long-acting amide local anaesthetic. Levobupivacaine exerts anaesthetic and analgesic effects through reversible blockade of neuronal sodium channel. Levobupivacaine can inhibit impulse transmission and conduction in cardiovascular and other tissues, possessing certain cardiac and CNS toxicity. Levobupivacaine is metabolized by hepatic cytochrome P450 (CYP450) enzymes in vivo. Levobupivacaine can also induce ferroptosis by miR-489-3p/SLC7A11 signaling in gastric cancer[1][2][3].
Related CatalogSignaling Pathways >>Membrane Transporter/Ion Channel >>Sodium ChannelResearch Areas >>CancerSignaling Pathways >>Apoptosis >>FerroptosisResearch Areas >>Neurological Disease
Target

Sodium channels, Ferroptosis[1][2]

In VitroLevobupivacaine (0-4 mM; 24 h) does not affect the viability of GES-1 cells but inhibits the viability of HGC27 and SGC7901 cells[2]. Levobupivacaine (2 mM; 24, 48 or 72 h) enhances Erastin-induced inhibitory impact on HGC27 and SGC7901 cell viabilities; induces the levels of Fe2+, iron, and lipid ROS[2]. Levobupivacaine (2 mM; 24 h) enhances the expression of miR-489-3p in HGC27 and SGC7901 cells, increases the levels of Fe2+ and iron[2]. Cell Viability Assay[2] Cell Line: GES-1, HGC27 and SGC790 Concentration: 0, 0.5, 1, 2 and 4 mM Incubation Time: 24 h Result: Did not affect the viability of normal gastric epithelial GES-1 cell lines but inhibited the viability of HGC27 and SGC7901 cells in a dose-dependent manner. Cell Viability Assay[2] Cell Line: HGC27 and SGC7901 (incubated with 5 μM erastin) Concentration: 2 mM Incubation Time: 24, 48 or 72 h Result: Enhanced erastin-induced inhibitory impact on HGC27 and SGC7901 cell viabilities; induced the levels of Fe2+, iron, and lipid ROS. RT-PCR[2] Cell Line: HGC27 and SGC7901 (incubated with 5 μM erastin) Concentration: 2 mM Incubation Time: 24 h Result: Enhanced the expression of miR-489-3p in HGC27 and SGC7901 cells, increased the levels of Fe2+ and iron.
In VivoLevobupivacaine (40 μmol/kg; IP; once daily for 25 days) significantly inhibits SGC7901 cell growth, and enhances the lipid ROS accumulation[2]. Levobupivacaine (5 or 36 mg/kg; IP; single dosage) increases the latency to partial seizures and prevents the occurrence of generalized seizures at low dosage; reduces the latency to N-methyl-d-aspartate (NMDA)-induced seizures and increased seizure severity at high dosage[3]. Animal Model: CD1 mice (30-35 g; induced epileptic seizures by injecting with NMDA)[3] Dosage: 5 or 36 mg/kg Administration: IP; single dosage Result: Increased the latency to partial seizures and prevented the occurrence of generalized seizures at 5 mg/kg; reduced the latency to NMDA-induced seizures and increased seizure severity at 36 mg/kg. Animal Model: SCID nude mice (6-8 weeks; subcutaneously injected with 5×106 SGC7901 cells)[2] Dosage: 40 μmol/kg Administration: IP; once daily for 25 days Result: Significantly inhibited SGC7901 cell growth, and enhanced the lipid ROS accumulation.
References

[1]. Sanford M, et al. Levobupivacaine: a review of its use in regional anaesthesia and pain management. Drugs. 2010 Apr 16;70(6):761-91.

[2]. Mao SH, et al. Levobupivacaine Induces Ferroptosis by miR-489-3p/SLC7A11 Signaling in Gastric Cancer. Front Pharmacol. 2021 Jun 9;12:681338.

[3]. Marganella C, et al. Comparative effects of levobupivacaine and racemic bupivacaine on excitotoxic neuronal death in culture and N-methyl-D-aspartate-induced seizures in mice. Eur J Pharmacol. 2005 Aug 22;518(2-3):111-5.

Chemical & Physical Properties

Density1.0±0.1 g/cm3
Boiling Point423.4±45.0 °C at 760 mmHg
Melting Point254ºC (dec.)(lit.)
Molecular FormulaC18H28N2O
Molecular Weight288.428
Flash Point209.9±28.7 °C
Exact Mass288.220154
PSA32.34000
LogP3.64
Vapour Pressure0.0±1.0 mmHg at 25°C
Index of Refraction1.547
InChIKeyLEBVLXFERQHONN-INIZCTEOSA-N
SMILESCCCCN1CCCCC1C(=O)Nc1c(C)cccc1C

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
TK6090000
CHEMICAL NAME :
2',6'-Pipecoloxylidide, 1-butyl-, L-(-)-
CAS REGISTRY NUMBER :
27262-47-1
LAST UPDATED :
199112
DATA ITEMS CITED :
7
MOLECULAR FORMULA :
C18-H28-N2-O
MOLECULAR WEIGHT :
288.48
WISWESSER LINE NOTATION :
T6NTJ A4 BVMR B1 F1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
52 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
APTOA6 Acta Pharmacologica et Toxicologica. (Copenhagen, Denmark) V.1-59, 1945-86. For publisher information, see PHTOEH Volume(issue)/page/year: 31,273,1972
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
7200 ug/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
APTOA6 Acta Pharmacologica et Toxicologica. (Copenhagen, Denmark) V.1-59, 1945-86. For publisher information, see PHTOEH Volume(issue)/page/year: 31,273,1972
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
100 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
APTOA6 Acta Pharmacologica et Toxicologica. (Copenhagen, Denmark) V.1-59, 1945-86. For publisher information, see PHTOEH Volume(issue)/page/year: 31,273,1972
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
9600 ug/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
APTOA6 Acta Pharmacologica et Toxicologica. (Copenhagen, Denmark) V.1-59, 1945-86. For publisher information, see PHTOEH Volume(issue)/page/year: 31,273,1972
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rabbit
DOSE/DURATION :
9700 ug/kg
TOXIC EFFECTS :
Behavioral - convulsions or effect on seizure threshold
REFERENCE :
APTOA6 Acta Pharmacologica et Toxicologica. (Copenhagen, Denmark) V.1-59, 1945-86. For publisher information, see PHTOEH Volume(issue)/page/year: 31,273,1972
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Parenteral
SPECIES OBSERVED :
Rodent - rabbit
DOSE/DURATION :
>120 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 26,78,1976
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intratracheal
SPECIES OBSERVED :
Rodent - rabbit
DOSE/DURATION :
14 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 26,78,1976

Safety Information

Hazard CodesXn: Harmful;T+: Very toxic;
RIDADRUN 2811 6
HS Code2933399090

Customs

HS Code2933399090
Summary2933399090. other compounds containing an unfused pyridine ring (whether or not hydrogenated) in the structure. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

Synonyms

2-Piperidinecarboxamide, 1-butyl-N-(2,6-dimethylphenyl)-, (2S)-
(2S)-1-Butyl-N-(2,6-dimethylphenyl)piperidine-2-carboxamide
L-(-)-Bupivacaine
2',6'-Pipecoloxylidide,1-butyl-,L-(-)
1-Butyl-N-(2,6-dimethylphenyl)-piperidine-2-carboxamide
(-)-Bupivacaine
Levobupivacaine
1-butyl-piperidine-2-carboxylic acid-(2,6-dimethyl-anilide)
(S)-(-)-Bupivacaine
(S)-Bupivacaine
(2S)-1-Butyl-N-(2,6-dimethylphenyl)-2-piperidinecarboxamide
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