Drug Information

General Information
Drug ID
DR00255
Drug Name
L-carnitine
Synonyms
(-)-(R)-3-Hydroxy-4-(trimethylammonio)butyrate; (-)-Carnitine; (-)-L-Carnitin; (-)-L-Carnitine; (3-Carboxy-2-hydroxypropyl)trimethyl-ammonium hydroxide, inner salt; (3R)-3-hydroxy-4-(trimethylammonio)butanoate; (3R)-3-hydroxy-4-(trimethylazaniumyl)butanoate; (L-3-Carboxy-2-hydroxypropyl)trimethylammonium hydroxide, inner salt; (R)-(3-Carboxy-2-hydroxypropyl)trimethylammonium hydroxide; (R)-(3-Carboxy-2-hydroxypropyl)trimethylammonium hydroxide, inner salt; (R)-3-Hydroxy-4-(trimethylammonio)butyrate; (R)-3-Hydroxy-4-trimethylammoniobutyrate; (R)-Carnitine; 1-CARNITINE; 1-Propanaminium, 3-carboxy-2-hydroxy-N,N,N-trimethyl-, hydroxide, inner salt; 1-Propanaminium, 3-carboxy-2-hydroxy-N,N,N-trimethyl-, inner salt, (2R)-(9CI); 3-Carboxy-2-hydroxy-N,N,N-trimethyl-1-propanaminium hydroxide, inner salt; 3-Carboxy-2-hydroxy-N,N,N-trimethyl-1-propanaminium hydroxide, innersalt; 3-carboxy-2-hydroxy-N,N,N-trimethyl-1-propanaminium; Ammonium, (3-carboxy-2-hydroxypropyl)trimethyl-, hydroxide, inner salt, L-(8CI); Ammonium, (3-carboxy-2-hydroxypropyl)trimethyl-, hydroxide,inner salt; Bicarnesine; C-1985; Carnicor; Carniking; Carniking 50; Carnilean; Carnitene; Carnitine; Carnitine (L-form); Carnitolo; Carnitor; Carnitor (TN); Carnovis; Carrier; DRG-0211; Gamma-Trimethyl-ammonium-beta-hydroxybutirate; Gamma-Trimethyl-beta-hydroxybutyrobetaine; Karnitin; L-(-)-Carnitine; L-Carnitine inner salt; L-carnitine Base; L-gamma-trimethyl-beta-hydroxybutyrobetaine; Lefcar; Levocarnitina; Levocarnitina [Spanish]; Levocarnitine; Levocarnitine (JAN/USP/INN); Levocarnitine [USAN:INN]; Levocarnitinum; Levocarnitinum [Latin]; Metina; R-(-)-3-hydroxy-4-trimethylaminobutyrate; ST 198; Vitamin B T; Vitamin BT
Drug Type
Small molecular drug
Indication Nutritional deficiency [ICD11:5B7Z] Approved [1]
Therapeutic Class
Vitamins
Structure
3D MOL 2D MOL
Formula
C7H15NO3
Canonical SMILES
C[N+](C)(C)CC(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
CAS Number
CAS 541-15-1
Pharmaceutical Properties Molecular Weight 161.2 Topological Polar Surface Area 60.4
Heavy Atom Count 11 Rotatable Bond Count 3
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 3
XLogP
-0.2
PubChem CID
10917
PubChem SID
103332887 ,103944816 ,104324626 ,115354359 ,118307976 ,12125266 ,124360711 ,124757780 ,124811873 ,125164584 ,126603600 ,126608844 ,131318133 ,131549872 ,134224069 ,134338232 ,134975930 ,135692459 ,136903840 ,137003561 ,141954380 ,143433319 ,143857297 ,15120307 ,15171033 ,2207 ,24892238 ,29279278 ,3612 ,46475651 ,46505864 ,48416167 ,49747058 ,49833446 ,49867038 ,53788226 ,56312758 ,56320717 ,56320718 ,57326565 ,77300350 ,7849237 ,8145671 ,8157930 ,841764 ,85165027 ,87565251 ,91146345 ,92308023 ,93166761
ChEBI ID
ChEBI:16347
TTD Drug ID
D0G8SQ
DT(s) Transporting This Drug ASCT2 Transporter Info Alanine/serine/cysteine/threonine transporter 2 Substrate [2]
CACT Transporter Info Carnitine/acylcarnitine translocase Substrate [3]
FLIPT2 Transporter Info Fly-like putative transporter 2 Substrate [4]
MCT9 Transporter Info Monocarboxylate transporter 9 Substrate [5]
OCTN1 Transporter Info Organic cation/carnitine transporter 1 Substrate [6]
OCTN2 Transporter Info Organic cation/carnitine transporter 2 Substrate [7]
Drug-Transporter Activity Data
Drug-Transporter Activity Data FLIPT2 Transporter Info Km =20 microM Oocytes-FLIPT2 [8]
OCTN2 Transporter Info Km =3.5 microM Human cervical cancer cell line (Hela)-OCTN2 [9]
OCTN2 Transporter Info Km =2.66 microM Human embryonic kidney cells (HEK293)-OCTN2 [10]
OCTN2 Transporter Info Km =4.3 microM Human embryonic kidney cells (HEK293)-OCTN2 [11]
OCTN2 Transporter Info Km =10.9 microM Human embryonic kidney cells (HEK293)-OCTN2 [11]
OCTN2 Transporter Info Km =14.07 microM Human enterocyte-like 2 cells (Caco-2)-OCTN2 [12]
OCTN2 Transporter Info Km =4.8 microM Oocytes-OCTN2 [13]
OCTN2 Transporter Info Km =54 microM Rat brain endothelial cells-OCTN2 [14]
References
1 L-carnitine was approved by FDA. The official website of the U.S. Food and Drug Administration. (2019)
2 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.
3 Molecular and functional analysis of SLC25A20 mutations causing carnitine-acylcarnitine translocase deficiency. Hum Mutat. 2004 Oct;24(4):312-20.
4 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.
5 Histological characterization of orphan transporter MCT14 (SLC16A14) shows abundant expression in mouse CNS and kidney. BMC Neurosci. 2016 Jul 1;17(1):43.
6 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.
7 Colistin is substrate of the carnitine/organic cation transporter 2 (OCTN2, SLC22A5). Drug Metab Dispos. 2017 Dec;45(12):1240-1244.
8 Molecular identification of a novel carnitine transporter specific to human testis. Insights into the mechanism of carnitine recognition. J Biol Chem. 2002 Sep 27;277(39):36262-71.
9 beta-lactam antibiotics as substrates for OCTN2, an organic cation/carnitine transporter. J Biol Chem. 2000 Jan 21;275(3):1699-707.
10 Na(+)-coupled transport of L-carnitine via high-affinity carnitine transporter OCTN2 and its subcellular localization in kidney. Biochim Biophys Acta. 2001 Jun 6;1512(2):273-84.
11 Na(+)-dependent carnitine transport by organic cation transporter (OCTN2): its pharmacological and toxicological relevance. J Pharmacol Exp Ther. 1999 Nov;291(2):778-84.
12 Expression and localization of organic cation/carnitine transporter OCTN2 in Caco-2 cells. Am J Physiol Gastrointest Liver Physiol. 2003 May;284(5):G863-71.
13 Functional and pharmacological characterization of human Na(+)-carnitine cotransporter hOCTN2. Am J Physiol Renal Physiol. 2000 Sep;279(3):F584-91.
14 Molecular cloning and functional characterization of the OCTN2 transporter at the RBE4 cells, an in vitro model of the blood-brain barrier. Brain Res. 2003 Apr 4;968(1):69-79.

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