Molecular Formula	C14H22N2O
Molecular Weight	234.34
Structure
State	solid
Clearance	The mean systemic clearance observed for intravenously administered lidocaine in a study of 15 adults was approximately 0.64 +/- 0.18 L/min [F4444].
Volume of distribution	The volume of distribution determined for lidocaine is 0.7 to 1.5 L/kg [L5948]. In particular, lidocaine is distributed throughout the total body water [L5930]. Its rate of disappearance from the blood can be described by a two or possibly even three-compartment model [L5930]. There is a rapid disappearance (alpha phase) which is believed to be related to uptake by rapidly equilibrating tissues (tissues with high vascular perfusion, for example) [L5930]. The slower phase is related to distribution to slowly equilibrating tissues (beta phase) and to its metabolism and excretion (gamma phase) [L5930]. Lidocaine's distribution is ultimately throughout all body tissues [L5930]. In general, the more highly perfused organs will show higher concentrations of the agent [L5930]. The highest percentage of this drug will be found in skeletal muscle, mainly due to the mass of muscle rather than an affinity [L5930].
Route of elimination	The excretion of unchanged lidocaine and its metabolites occurs predominantly via the kidney with less than 5% in the unchanged form appearing in the urine [F4349, L5930]. The renal clearance is inversely related to its protein binding affinity and the pH of the urine [L5930]. This suggests by the latter that excretion of lidocaine occurs by non-ionic diffusion [L5930].
Protein binding	The protein binding recorded for lidocaine is about 60 to 80% and is dependent upon the plasma concentration of alpha-1-acid glycoprotein [F4349, L5948]. Such percentage protein binding bestows lidocaine with a medium duration of action when placed in comparison to other local anesthetic agents [L5948].
Half life	The elimination half-life of lidocaine hydrochloride following an intravenous bolus injection is typically 1.5 to 2.0 hours [F4349]. Because of the rapid rate at which lidocaine hydrochloride is metabolized, any condition that affects liver function may alter lidocaine HCl kinetics [F4349]. The half-life may be prolonged two-fold or more in patients with liver dysfunction [F4349].
Absorption	In general, lidocaine is readily absorbed across mucous membranes and damaged skin but poorly through intact skin [F4468]. The agent is quickly absorbed from the upper airway, tracheobronchial tree, and alveoli into the bloodstream [F4468]. And although lidocaine is also well absorbed across the gastrointestinal tract the oral bioavailability is only about 35% as a result of a high degree of first-pass metabolism [F4468]. After injection into tissues, lidocaine is also rapidly absorbed and the absorption rate is affected by both vascularity and the presence of tissue and fat capable of binding lidocaine in the particular tissues [F4468]. The concentration of lidocaine in the blood is subsequently affected by a variety of aspects, including its rate of absorption from the site of injection, the rate of tissue distribution, and the rate of metabolism and excretion [F4349, L5930, L5948]. Subsequently, the systemic absorption of lidocaine is determined by the site of injection, the dosage given, and its pharmacological profile [F4349, L5930, L5948]. The maximum blood concentration occurs following intercostal nerve blockade followed in order of decreasing concentration, the lumbar epidural space, brachial plexus site, and subcutaneous tissue [F4349, L5930, L5948]. The total dose injected regardless of the site is the primary determinant of the absorption rate and blood levels achieved [F4349, L5930, L5948]. There is a linear relationship between the amount of lidocaine injected and the resultant peak anesthetic blood levels [F4349, L5930, L5948]. Nevertheless, it has been observed that lidocaine hydrochloride is completely absorbed following parenteral administration, its rate of absorption depending also on lipid solubility and the presence or absence of a vasoconstrictor agent [F4349, L5930, L5948]. Except for intravascular administration, the highest blood levels are obtained following intercostal nerve block and the lowest after subcutaneous administration [F4349, L5930, L5948]. Additionally, lidocaine crosses the blood-brain and placental barriers, presumably by passive diffusion [F4349].
Trade names	Xylocaine
Description	Local anesthetics

Toxicity	Dose	Time	Species	Model	Method	Action	Positive criterion	Reference
DEPOLARIZATION								197
MEMBRANE POTENTIAL	339.5 µM	30 mins	mouse	liver mitochondria	Rh123 fluorescence (excitation 485 nm, emission 535 nm) are recorded using a fluorescence multi-well plate reader (mCICCP (20 µM) treatments was considered as the 100% baseline for ΔΨm loss)	decrease	EC20	36
RESPIRATION	> 400 µM	60 mins	mouse	liver mitochondria	Oxygen consumption was monitored with 50nM MitoXpress ( an oxygen-sensitive phosphorescent dye) using a spectrofluorimeter (Tecan Infinite 200; λExcitation 380nm; λEmission 650nm). Rotenone (2µM) was used as 100% baseline for complex I inhibition.	decrease	EC20	36
RESPIRATION	188.2 µM	60 mins	mouse	liver mitochondria	Oxygen consumption was monitored with 50nM MitoXpress ( an oxygen-sensitive phosphorescent dye) using a spectrofluorimeter (Tecan Infinite 200; λExcitation 380nm; λEmission 650nm). Oligomycin A (1µM) was used as 100% baseline for complex II inhibition.	increase	EC20	36
OXYGEN CONSUMPTION RATE (OCR)	300 μM	2 minutes	human	HepG2	Measurement of OCR	Negative	EC50	7
ECAR	300 μM	2 minutes	human	HepG2	Measurement of ECAR	Negative	EC50	7
SWELLING	> 800 µM	30 mins	mouse	liver mitochondria	swelling assay: Absorbance at 545 nm using a fluorescence multi-well plate reader (CaCl2 (50 µM) was considered as the 100% baseline for the swelling )	increase	EC20	36

Target	Dose	Time	Species	Model	Method	Action	Positive criterion	Reference
NADH:ubiquinone reductase	> 400 µM	60 mins	mouse	liver mitochondria	Oxygen consumption was monitored with 50nM MitoXpress ( an oxygen-sensitive phosphorescent dye) using a spectrofluorimeter (Tecan Infinite 200; λExcitation 380nm; λEmission 650nm). Rotenone (2µM) was used as 100% baseline for complex I inhibition.	inhibit	EC20	36
Cytochrome c	> 800 µM	30 mins	mouse	liver mitochondria	Cytochrome c release was evaluated using ELISA kit ( 20 µg/ml Alamethicin was used as 100% baseline)	release	EC20	36

Pictogram	Signal	Statements	Precautionary Statement Codes
	Warning	Aggregated GHS information provided by 285 companies from 7 notifications to the ECHA C&L Inventory. Reported as not meeting GHS hazard criteria by 2 of 285 companies. For more detailed information, please visit ECHA C&L website Of the 6 notification(s) provided by 283 of 285 companies with hazard statement code(s): H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral] Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.	P264, P270, P301+P312, P330, and P501; (The corresponding statement to each P-code can be found at the GHS Classification page.)
	Warning	The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory. H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]	P264, P270, P301+P312, P330, and P501; (The corresponding statement to each P-code can be found at the GHS Classification page.)
	Warning	H302: Harmful if swallowed [Warning Acute toxicity, oral]	P264, P270, P301+P312, P330, and P501; (The corresponding statement to each P-code can be found at the GHS Classification page.)
	Danger	H302: Harmful if swallowed [Warning Acute toxicity, oral] H317: May cause an allergic skin reaction [Warning Sensitization, Skin] H362: May cause harm to breast-fed children [Reproductive toxicity, effects on or via lactation] H370: Causes damage to organs [Danger Specific target organ toxicity, single exposure] H372: Causes damage to organs through prolonged or repeated exposure [Danger Specific target organ toxicity, repeated exposure]	P201, P260, P261, P263, P264, P270, P272, P280, P301+P312, P302+P352, P307+P311, P308+P313, P314, P321, P330, P333+P313, P363, P405, and P501; (The corresponding statement to each P-code can be found at the GHS Classification page.)

Organism	Test type	Route	Dose (normalized dose)	Effect	Source
infant	TDLo	oral	1632mg/kg/1W- (1632mg/kg)		Clinical Pediatrics Vol. 22, Pg. 190, 1983.
infant	TDLo	intravenous	10mg/kg (10mg/kg)		Journal of Toxicology, Clinical Toxicology. Vol. 28, Pg. 101, 1990.
mouse	LD50	intramuscular	177mg/kg (177mg/kg)		Drug Development Research. Vol. 21, Pg. 277, 1990.
mouse	LD50	intraperitoneal	63mg/kg (63mg/kg)		Archives Internationales de Pharmacodynamie et de Therapie. Vol. 274, Pg. 253, 1985.
rat	LD50	subcutaneous	570mg/kg (570mg/kg)		Research Progress in Organic-Biological and Medicinal Chemistry. Vol. 2, Pg. 299, 1970.
rabbit	LD50	intratracheal	28mg/kg (28mg/kg)		Archives Internationales de Pharmacodynamie et de Therapie. Vol. 200, Pg. 359, 1972.
mouse	LD50	intravenous	15mg/kg (15mg/kg)		Journal of Pharmacy and Pharmacology. Vol. 14, Pg. 48T, 1962.
rabbit	LD50	intravenous	25600ug/kg (25.6mg/kg)		Drugs in Japan Vol. 6, Pg. 879, 1982.
man	TDLo	intravenous	7143ug/kg (7.143mg/kg)	cardiac: pulse rate increase without fall in bp	Chest. Vol. 61, Pg. 682, 1972.
dog	LDLo	intravenous	65700ug/kg (65.7mg/kg)		Journal de Pharmacologie. Vol. 2, Pg. 240, 1971.
mouse	LD50	subcutaneous	163mg/kg (163mg/kg)		Proceedings of the Society for Experimental Biology and Medicine. Vol. 103, Pg. 353, 1960.
rat	LD50	intraperitoneal	122mg/kg (122mg/kg)		Journal of Pharmacology and Experimental Therapeutics. Vol. 111, Pg. 224, 1954.
frog	LD50	parenteral	159mg/kg (159mg/kg)		Archives Internationales de Pharmacodynamie et de Therapie. Vol. 289, Pg. 278, 1987.
man	TDLo	implant	5714ug/kg (5.714mg/kg)	behavioral: convulsions or effect on seizure threshold	Canadian Medical Association Journal. Vol. 137, Pg. 219, 1987.
mouse	LD50	oral	220mg/kg (220mg/kg)		Research Progress in Organic-Biological and Medicinal Chemistry. Vol. 2, Pg. 299, 1970.
guinea pig	LD50	intravenous	24500ug/kg (24.5mg/kg)		Archives Internationales de Pharmacodynamie et de Therapie. Vol. 113, Pg. 313, 1958.
infant	TDLo	oral	1600ug/kg/9H- (1.6mg/kg)	behavioral: convulsions or effect on seizure threshold	Annals of Emergency Medicine. Vol. 17, Pg. 725, 1988.
man	TDLo	intravenous	9mg/kg/4H-C (9mg/kg)	cardiac: cardiomyopathy including infarction	Drug Intelligence and Clinical Pharmacy. Vol. 19, Pg. 669, 1985.
child	TDLo	intravenous	60mg/kg/1H (60mg/kg)		Journal of Toxicology, Clinical Toxicology. Vol. 24, Pg. 51, 1986.
rat	LD50	intravenous	21mg/kg (21mg/kg)		Research Progress in Organic-Biological and Medicinal Chemistry. Vol. 2, Pg. 299, 1970.

Acute coronary syndrome

Acute myocardial infarction

Agitation

Anal fissure

Anal pruritus

Anorectal discomfort

Arrhythmia

Arthropod bite

Bladder pain

Cardiac arrest

Cardiovascular insufficiency

Cystitis

Cystitis noninfective

Discomfort

Eczema

Haemorrhoids

Herpes zoster

Myocardial infarction

Oesophagitis

Oropharyngeal discomfort

Oropharyngeal pain

Pain

Photosensitivity reaction

Post gastric surgery syndrome

Post herpetic neuralgia

Pruritus

Pruritus genital

Retching

Sunburn

Tenderness

Toxicity to various agents

Urethritis

Urethritis noninfective

Ventricular arrhythmia

Vulvovaginal pruritus

Nausea (0.02)

Vomiting (0.01)

(2,6-dimethylphenyl)carbamoylmethyl-diethyl-azanium	.alpha.-(Diethylamino)-2,6-acetoxylidide	.alpha.-Diethylamino-2,6-acetoxylidide
.alpha.-Diethylamino-2,6-dimethylacetanilide	.alpha.-Diethylaminoaceto-2,6-xylidide	.omega.-Diethylamino-2,6-dimethylacetanilide
137-58-6	2', 2-(diethylamino)-	2',6'-Acetoxylidide, 2-(diethylamino)-
2-(Diethylamino)-2'',6''-acetoxylidide	2-(Diethylamino)-2',6'-acetoxylidide	2-(Diethylamino)-N-(2,6-Dimethylphenyl)ethanamide
2-(Diethylamino)-N-(2,6-dimethylphenyl)-acetamide	2-(Diethylamino)-N-(2,6-dimethylphenyl)acetamide	2-(Diethylamino)-N-(2,6-dimethylphenyl)acetamide #
2-Diethylamino-N-(2,6-dimethyl-phenyl)-acetamide	2-Diethylamino-N-(2,6-dimethylphenyl)acetamide	4-12-00-02538 (Beilstein Handbook Reference)
6108-05-0 (MONOHYDROCHLORIDE MONOHYDRATE))	91484-71-8	98PI200987
A18187	AB00053581	AB00053581-27
AB00053581-28	AB00053581_29	AB00053581_30
AB2000065	AC-10282	AKOS001026768
ANW-42187	ARONIS23855	AS-13718
Acetamide, 2-(diethylamino)-N-(2,6-dimethylphenyl)-	Alphacaine	Alphacaine;Xylocaine;lignocaine
Anestacon	BBL005525	BCP09081
BDBM50017662	BIDD:GT0342	BPBio1_000197
BRD-K52662033-001-02-6	BRD-K52662033-003-05-5	BRD-K52662033-003-14-7
BRN 2215784	BSPBio_000179	BSPBio_001359
BSPBio_003004	Bio1_000379	Bio1_000868
Bio1_001357	Bio2_000079	Bio2_000559
C07073	C14H22N2O	CAS-137-58-6
CAS-73-78-9	CCG-100824	CDS1_000283
CHEBI:6456	CHEMBL79	CPD000058189
CS-2070	CTK3J2126	Cappicaine
Certified Reference Material	Cito optadren	Cuivasil
D00358	DB00281	DSSTox_CID_25166
DSSTox_GSID_45166	DSSTox_RID_80716	DTXSID1045166
Dalcaine	Dentipatch	Dentipatch (TN)
Diethylaminoacet-2,6-xylidide	Diethylaminoaceto-2,6-xylidide	Dilocaine
DivK1c_000174	DivK1c_001323	Duncaine
EINECS 205-302-8	ELA-Max	EMBOLEX
Epitope ID:116205	Esracaine	FT-0082378
FT-0600570	GTPL2623	Gravocain
HMS1791D21	HMS1989D21	HMS2051C21
HMS2089E15	HMS2235O14	HMS3371J04
HMS3393C21	HMS3428O07	HMS3651G09
HMS548M19	HSDB 3350	HY-B0185
IDI1_000174	IDI1_033829	Isicaina
Isicaine	J10173	Jetocaine
K-4450	KBio1_000174	KBio2_000079
KBio2_001598	KBio2_002647	KBio2_004166
KBio2_005215	KBio2_006734	KBio3_000157
KBio3_000158	KBio3_002224	KBioGR_000079
KBioGR_000599	KBioSS_000079	KBioSS_001598
KS-000046GY	L-Caine	L0156
LIDOCAINE (73-58-6 (MONOHYDROCHLORIDE)	LIDOPEN	LQZ
LS-805	Leostesin	Lida-Mantle
Lidaform HC (Salt/Mix)	Lidamantle HC (Salt/Mix)	Lidocaina
Lidocaina [INN-Spanish]	Lidocaine (Alphacaine)	Lidocaine (JP17/USP/INN)
Lidocaine (VAN)	Lidocaine 1.0 mg/ml in Methanol	Lidocaine Base
Lidocaine Hydrocarbonate	Lidocaine Monohydrochloride	Lidocaine [USAN:INN:JAN]
Lidocaine [USP:INN:BAN:JAN]	Lidocaine solution, 1.0 mg/mL in methanol, ampule of 1 mL, certified reference material	Lidocaine(Alphacaine)
Lidocaine, 97.5%	Lidocaine, British Pharmacopoeia (BP) Reference Standard	Lidocaine, European Pharmacopoeia (EP) Reference Standard
Lidocaine, Pharmaceutical Secondary Standard	Lidocaine, United States Pharmacopeia (USP) Reference Standard	Lidocaine, analytical standard
Lidocaine, powder	LidocaineHClH2O	Lidocainum
Lidocainum [INN-Latin]	Lidocaton	Lidoderm
Lidothesin (Salt/Mix)	Lignocaine	Lignocaine base
Lignocaine base 100 microg/mL in Methanol	Lignocainum	Lopac-L-5647
Lopac0_000669	M620	MCULE-9294700940
MFCD00026733	MLS000069724	MLS000758263
MLS001074177	MLS001423964	Maricaine
Maybridge1_002571	N-(2,6-Dimethylphenyl)-N2,N2-diethylglycinamide	N-(2,6-dimethylphenyl)-N(2),N(2)-diethylglycinamide
N-(2,6-dimethylphenyl)-N~2~,N~2~-diethylglycinamide	N1-(2,6-dimethylphenyl)-2-(diethylamino)acetamide	N1-(2,6-dimethylphenyl)-N2,N2-diethylglycinamide
NC00074	NCGC00015611-01	NCGC00015611-02
NCGC00015611-03	NCGC00015611-04	NCGC00015611-05
NCGC00015611-06	NCGC00015611-07	NCGC00015611-08
NCGC00015611-09	NCGC00015611-10	NCGC00015611-11
NCGC00015611-12	NCGC00015611-13	NCGC00015611-14
NCGC00015611-15	NCGC00015611-16	NCGC00015611-18
NCGC00022176-05	NCGC00022176-06	NCGC00022176-07
NCGC00022176-08	NCGC00022176-09	NINDS_000174
NNJVILVZKWQKPM-UHFFFAOYSA-N	NSC 40030	NSC-40030
NSC40030	Neosporin Plus (Salt/Mix)	N~1~-(2,6-dimethylphenyl)-N~2~,N~2~-diethylglycinamide
Octocaine	Opera_ID_385	Prestwick0_000050
Prestwick1_000050	Prestwick2_000050	Prestwick3_000050
Q216935	Qualigens	RTR-031283
Remicaine	Rucaina	SAM001247018
SB19118	SBB080556	SBI-0050648.P004
SC-19460	SCHEMBL15689	SCHEMBL17967359
SMR000058189	SPBio_001525	SPBio_002100
ST023341	STK552033	SW196598-4
Solcain	Spectrum2_001343	Spectrum3_001392
Spectrum4_000070	Spectrum5_001549	Spectrum_001118
TR-031283	Tox21_110183	Tox21_110183_1
UNII-98PI200987	Versatis	W-108233
WLN: 2N2 & 1VMR B1 F1	Xilina	Xilocaina
Xilocaina [Italian]	Xllina	Xycaine
Xylestesin	Xylesthesin	Xyline
Xylocain	Xylocaine	Xylocaine (TN)
Xylocaine CO2	Xylocitin	Xyloneural (Salt/Mix)
Xyloneural (free base)	Xylotox	Z55135799
ZINC20237	ZTlido	Zingo (Salt/Mix)
Ztilido	alfa-Dietilamino-2,6-dimetilacetanilide	alfa-Dietilamino-2,6-dimetilacetanilide [Italian]
alpha-Diethylamino-2,6-dimethylacetanilide	lidocaine	s1357

DrugBank Name	Lidocaine
DrugBank	DB00281
CAS Number	137-58-6, 34941-90-7, 73-78-9, 91484-71-8
PubChem Compound	3676
KEGG Compound ID	C07073
KEGG Drug	D00358
PubChem.Substance	46505060
ChEBI	6456
PharmGKB	PA450226
ChemSpider	3548
BindingDB	50017662.0
TTD	DAP000121
Wikipedia	Lidocaine
HET	LQZ
DPD	10225|9471