General Information of the Compound
Compound ID
CP0076729
Compound Name
LEVOBUPIVACAINE HYDROCHLORIDE
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Synonyms
(2S)-1-butyl-N-(2,6-dimethylphenyl)piperidine-2-carboxamide
(S)-1-Butyl-2',6'-pipecoloxylidide
(S)-bupivacaine
Chirocaine (TN)
L(-)-Bupivacaine
L-(-)-1-Butyl-2',6'-pipecoloxylidide
L-(-)-bupivacaine
Levobupivacaine
Levobupivacaine (INN)
Levobupivacaine [INN:BAN]
Novabupi
Novabupi (TN)
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Structure
Formula
C18H28N2O
Molecular Weight
288.435
Canonical SMILES
CCCCN1CCCC[C@H]1C(=O)Nc1c(C)cccc1C
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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)/t16-/m0/s1
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InChIKey
LEBVLXFERQHONN-INIZCTEOSA-N
CAS
27262-47-1
Physicochemical Property
logP
3.89654
Rotatable Bonds
5
Heavy Atom Count
21
Polar Areas
32.34
Hydrogen Bond Donor Count
1
Hydrogen Bond Acceptor Count
2
Complexity
21

"RO5" indicates the cutoff set by lipinski's rule of five:

(1) Molecular weight less than 500 Dalton;

(2) xlogp less than 5;

(3) No more than 5 hbonddonor (Hydrogen Bond Donor Count);

(4) No more than 10 hbondacc (Hydrogen Bond Acceptor Count);

(5) No more than 10 rotbonds (Rotatable Bond Count).

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PubChem ID
CID: 92253
SID: 14775644
ChEMBL ID
CHEMBL1201193
DrugBank ID
DB01002
Map of Molecular Bioactivity Related to the Compound
Map of Molecular Bioactivity Related to the Compound

Compound
Cell Line
Protein

Bioactivity Value:

<= 0.1 μM
> 0.1 μM and <= 10 μM
> 10 μM
Imprecise Activity
Table of Molecular Bioactivities Related to the Compound
Protein ID: PT00817, Cytochrome P450 2D6
Cell-based Assay
Cell Line ID Cell Line Name Cell Line Organism
CL000023 BTI-Tn-5B1-4 Trichoplusia ni (Cabbage looper)  1
1
IC50 = 196.4 nM
   TI
   LI
   LO
   TS
Biochemical Assays
1 Potency = 501.2 nM
Clinical Information about the Compound
Drug 1 ( Levobupivacaine )
Drug Name Levobupivacaine
Company AstraZeneca
Indication
Anaesthesia
Approved