General Information of Drug (ID: DMJBOCR)

Drug Name
Levacecarnine hci
Synonyms
Levocarnitine; L-carnitine; 541-15-1; vitamin BT; (R)-Carnitine; Carnitor; (-)-Carnitine; Carnitine; Karnitin; (-)-L-Carnitine; L-(-)-Carnitine; Levocarnitina; Carnitene; Levocarnitinum; Metina; L-Carnitine inner salt; Carniking; Carnovis; Carnitolo; Carnilean; Carrier; Lefcar; Carnitine, (-)-; L-carnitine Base; Levocarnitinum [Latin]; Levocarnitina [Spanish]; ST 198; L(-)-Carnitine; Carniking 50; (3R)-3-hydroxy-4-(trimethylammonio)butanoate; Levocarnitine [USAN:INN]; gamma-Trimethyl-beta-hydroxybutyrobetaine; bicarnesine; Nicetile (TN); L-Carnitine
Indication
Disease Entry ICD 11 Status REF
Cognitive impairment 6D71 Approved [1]
Medium chain acyl-CoA dehydrogenase deficiency N.A. Approved [2]
Nutritional deficiency 5B50-5B71 Approved [3]
Postpoliomyelitis syndrome N.A. Approved [2]
Ulcerative colitis DD71 Approved [2]
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 161.2
Logarithm of the Partition Coefficient (xlogp) -0.2
Rotatable Bond Count (rotbonds) 3
Hydrogen Bond Donor Count (hbonddonor) 1
Hydrogen Bond Acceptor Count (hbondacc) 3
ADMET Property
Absorption Tmax
The time to maximum plasma concentration (Tmax) is 3.3 h []
Bioavailability
The bioavailability of drug is 15% []
Clearance
The total body clearance of drug is 4 L/h []
Half-life
The concentration or amount of drug in body reduced by one-half in 17.4 hours [4]
Metabolism
The drug is metabolized via the bacterial microflora []
MRTD
The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 305.15909 micromolar/kg/day [5]
Unbound Fraction
The unbound fraction of drug in plasma is 1% [4]
Vd
The volume of distribution (Vd) of drug is 29.0 +/- 7.1 L []
Chemical Identifiers
Formula
C7H15NO3
IUPAC Name
(3R)-3-hydroxy-4-(trimethylazaniumyl)butanoate
Canonical SMILES
C[N+](C)(C)C[C@@H](CC(=O)[O-])O
InChI
InChI=1S/C7H15NO3/c1-8(2,3)5-6(9)4-7(10)11/h6,9H,4-5H2,1-3H3/t6-/m1/s1
InChIKey
PHIQHXFUZVPYII-ZCFIWIBFSA-N
Cross-matching ID
PubChem CID
10917
ChEBI ID
CHEBI:16347
CAS Number
541-15-1
DrugBank ID
DB00583
TTD ID
D0G8SQ
VARIDT ID
DR00255
INTEDE ID
DR0936
ACDINA ID
D00359
Combinatorial Drugs (CBD) Click to Jump to the Detailed CBD Information of This Drug
Repurposed Drugs (RPD) Click to Jump to the Detailed RPD Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Carnitine O-palmitoyltransferase I (CPT1B) TTDL0NY CPT1B_HUMAN Activator [6]

Drug Transporter (DTP)
DTP Name DTP ID UniProt ID MOA REF
Carnitine/acylcarnitine translocase (SLC25A20) DTQOUM4 MCAT_HUMAN Substrate [7]
Monocarboxylate transporter 9 (SLC16A9) DTQK5O9 MOT9_HUMAN Substrate [8]
Fly-like putative transporter 2 (SLC22A16) DTPATLS S22AG_HUMAN Substrate [9]
Alanine/serine/cysteine/threonine transporter 2 (SLC1A5) DTW7AE3 AAAT_HUMAN Substrate [10]
Organic cation/carnitine transporter 1 (SLC22A4) DT2EG60 S22A4_HUMAN Substrate [11]
Organic cation/carnitine transporter 2 (SLC22A5) DT3HUVD S22A5_HUMAN Substrate [12]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 2E1 (CYP2E1) DEVDYN7 CP2E1_HUMAN Substrate [13]
Carnitine O-acetyltransferase (CRAT) DEIGQCY CACP_HUMAN Substrate [14]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Gamma-butyrobetaine dioxygenase (BBOX1) OTKEX4RK BODG_HUMAN Biotransformations [15]
Organic cation/carnitine transporter 2 (SLC22A5) OTC36TYB S22A5_HUMAN Gene/Protein Processing [16]
Solute carrier family 22 member 4 (SLC22A4) OT4LOVI9 S22A4_HUMAN Regulation of Drug Effects [17]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Drug Inactive Ingredient(s) (DIG) and Formulation(s) of This Drug

DIG
DIG Name DIG ID PubChem CID Functional Classification
Magnesium stearate E00208 11177 lubricant
Povidone E00667 Not Available Binding agent; Coating agent; Disintegrant; Film/membrane-forming agent; Solubilizing agent; Suspending agent
Pharmaceutical Formulation
Formulation Name Drug Dosage Dosage Form Route
Levocarnitine 330 mg tablet 330 mg Oral Tablet Oral
Jump to Detail Pharmaceutical Formulation Page of This Drug

References

1 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services. 2015
2 A standard database for drug repositioning. Sci Data. 2017 Mar 14;4:170029.
3 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 4780).
4 Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
5 Estimating the safe starting dose in phase I clinical trials and no observed effect level based on QSAR modeling of the human maximum recommended daily dose
6 Central ghrelin regulates peripheral lipid metabolism in a growth hormone-independent fashion. Endocrinology. 2009 Oct;150(10):4562-74.
7 Molecular and functional analysis of SLC25A20 mutations causing carnitine-acylcarnitine translocase deficiency. Hum Mutat. 2004 Oct;24(4):312-20.
8 Histological characterization of orphan transporter MCT14 (SLC16A14) shows abundant expression in mouse CNS and kidney. BMC Neurosci. 2016 Jul 1;17(1):43.
9 The human carnitine transporter SLC22A16 mediates high affinity uptake of the anticancer polyamine analogue bleomycin-A5. J Biol Chem. 2010 Feb 26;285(9):6275-84.
10 A polarized localization of amino acid/carnitine transporter B(0,+) (ATB(0,+)) in the blood-brain barrier. Biochem Biophys Res Commun. 2008 Nov 14;376(2):267-70.
11 Spontaneous development of intestinal and colonic atrophy and inflammation in the carnitine-deficient jvs (OCTN2(-/-)) mice. Mol Genet Metab. 2007 Dec;92(4):315-24.
12 Colistin is substrate of the carnitine/organic cation transporter 2 (OCTN2, SLC22A5). Drug Metab Dispos. 2017 Dec;45(12):1240-1244.
13 Modulation of ethanol-mediated CYP2E1 induction by clofibrate and L-carnitine in rat liver. Biol Pharm Bull. 1993 Dec;16(12):1240-3.
14 Structural and mutational characterization of L-carnitine binding to human carnitine acetyltransferase. J Struct Biol. 2004 Jun;146(3):416-24.
15 The disruption of L-carnitine metabolism by aluminum toxicity and oxidative stress promotes dyslipidemia in human astrocytic and hepatic cells. Toxicol Lett. 2011 Jun 24;203(3):219-26. doi: 10.1016/j.toxlet.2011.03.019. Epub 2011 Mar 23.
16 Clozapine-induced reduction of l-carnitine reabsorption via inhibition/down-regulation of renal carnitine/organic cation transporter 2 contributes to liver lipid metabolic disorder in mice. Toxicol Appl Pharmacol. 2019 Jan 15;363:47-56. doi: 10.1016/j.taap.2018.11.007. Epub 2018 Nov 19.
17 Transcellular movement of hydroxyurea is mediated by specific solute carrier transporters. Exp Hematol. 2011 Apr;39(4):446-56.