Compound: Levobupivacaine
SMILES: O=C(Nc1c(cccc1C)C)[C@H]2N(CCCC2)CCCC
InChIKey: LEBVLXFERQHONN-INIZCTEOSA-N
Synonyms: Levobupivacaine, 27262-47-1, (S)-bupivacaine, (-)-bupivacaine, L-(-)-bupivacaine, (2S)-1-butyl-N-(2,6-dimethylphenyl)piperidine-2-carboxamide, Levobupivacaina, Novabupi, (S)-1-Butyl-2',6'-pipecoloxylidide, L-bupivacaine, Bupivacaine, (s)-, Bupivacaine, (-)-, L-(-)-1-Butyl-2',6'-pipecoloxylidide, A5H73K9U3W, CHEBI:6149, DTXSID8048496, 2',6'-Pipecoloxylidide, 1-butyl-, L-(-)-, 2-Piperidinecarboxamide, 1-butyl-N-(2,6-dimethylphenyl)-, (2S)-, (s)-1-butyl-n-(2,6-dimethylphenyl)-2-piperidinecarboxamide, (2S)-1-butyl-N-(2,6-dimethylphenyl)piperidine-2-carboximidic acid, levobupivacainum, Bupivacaine (-)-, RefChem:153196, DTXCID8028470, N01BB10, 690-076-7, L(-)-Bupivacaine, (S)-(-)-Bupivacaine, (S)-1-Butyl-N-(2,6-dimethylphenyl)piperidine-2-carboxamide, (2S)-1-butyl-N-(2,6-dimethylphenyl)-2-piperidinecarboxamide, Bupivacaine (-)-form, Levobupivacaine (INN), MFCD00936851, LEVOBUPIVACAINE [INN], Levobupivacaine [INN:BAN], Levobupivacaine free base, Novabupi (TN), NCGC00159482-02, UNII-A5H73K9U3W, 27262-47-1 (free base), Epitope ID:1597623, SCHEMBL34537, BIDD:GT0471, LEVOBUPIVACAINE [VANDF], GTPL7211, orb1307450, LEVOBUPIVACAINE [MART.], CHEMBL1201193, LEVOBUPIVACAINE [WHO-DD], GLXC-06557, HY-B0653, BUPIVACAINE (-)-FORM [MI], BDBM50350791, BDBM50417951, EBC-03922, s5181, AKOS016340525, DB01002, FB19357, KS-5195, NCGC00016733-01, NCGC00159482-03, DA-54878, SY465927, CAS-18010-40-7, (S)-Bupivacaine; Ropivacaine EP Impurity A, CS-0009570, NS00077944, C07887, D08116, D87861, Q3272027, Z2242128693, (2~{S})-1-butyl-~{N}-(2,6-dimethylphenyl)piperidine-2-carboxamide, ROPIVACAINE HYDROCHLORIDE MONOHYDRATE IMPURITY A [EP IMPURITY], 41148-30-5, OJ0
Theoretical properties:
molecular_formula: C18H28N2O
molecular_weight: 288.4 g/mol
exact_mass: 288.220163521 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 1
hydrogen_bond_acceptor_count: 2
rotatable_bond_count: 5
heavy_atom_count: 21
topological_polar_surface_area: 32.3 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
solubility: 9.77e-02 g/L
Descriptions:
pubchem: Levobupivacaine is the (S)-()-enantiomer of bupivacaine. It has a role as a local anaesthetic, an EC 3.1.1.8 (cholinesterase) inhibitor, an adrenergic antagonist, an amphiphile and an EC 3.6.3.8 (Ca(2+)-transporting ATPase) inhibitor. It is a conjugate base of a levobupivacaine(1+). It is an enantiomer of a dextrobupivacaine.
chebi: The (<i>S</i>)-(−)-enantiomer of bupivacaine.
chembl: LEVOBUPIVACAINE is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.
wikipedia: Levobupivacaine (rINN) is a local anaesthetic drug indicated for minor and major surgical anaesthesia and pain management. It is a long-acting amide-type local anaesthetic that blocks nerve impulses by inhibiting sodium ion influx into the nerve cells. Levobupivacaine is the S-enantiomer of racemic bupivacaine and therefore similar in pharmacological effects. The drug typically starts taking effect within 15 minutes and can last up to 16 hours depending on factors such as site of administration and dosage.
Levobupivacaine was designed, in the late 1970s, to be a safer and more effective alternative to bupivacaine, which had been associated with a higher risk of cardiotoxicity. 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 and has a longer motor block onset time. Ropivacaine is, next to levobupivacaine, another less cardiotoxic alternative to bupivacaine.
Levobupivacaine hydrochloride is commonly marketed by AbbVie under the trade name Chirocaine. In Europe, Chirocaine is available – prescription only – in concentrations ranging from 0.625 mg/mL to 7.5 mg/mL.