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labetalol 🐶 Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definition	Drug id	CAS RN
aromatic ring -CH(-OH)-CH2-NH-R	1531	36894-69-6

Description:

Molecule	Description
Molfile Inchi Smiles Synonyms: labetalol labetalol hydrochloride albetol ibidomide labetalol HCl SCH 19927 SCH-19927	A salicylamide derivative that is a non-cardioselective blocker of BETA-ADRENERGIC RECEPTORS and ALPHA-1 ADRENERGIC RECEPTORS. Molecular weight: 328.41 Formula: C19H24N2O3 CLOGP: 2.50 LIPINSKI: 0 HAC: 5 HDO: 4 TPSA: 95.58 ALOGS: -4.75 ROTB: 8 Status: OFP Legend: OFP - off patent OFM - off market ONP - on patent

Molecule

Description

Molfile Inchi Smiles

Synonyms:

labetalol
labetalol hydrochloride
albetol
ibidomide
labetalol HCl
SCH 19927
SCH-19927

A salicylamide derivative that is a non-cardioselective blocker of BETA-ADRENERGIC RECEPTORS and ALPHA-1 ADRENERGIC RECEPTORS.

Molecular weight: 328.41
Formula: C19H24N2O3
CLOGP: 2.50
LIPINSKI: 0
HAC: 5
HDO: 4
TPSA: 95.58
ALOGS: -4.75
ROTB: 8

Status: OFP

Legend:
OFP - off patent
OFM - off market
ONP - on patent

Drug dosage:

Dose	Unit	Route
0.60	g	O
0.60	g	P

ADMET properties:

Property	Value	Reference
BDDCS (Biopharmaceutical Drug Disposition Classification System)	1	Benet LZ, Broccatelli F, Oprea TI
S (Water solubility)	16 mg/mL	Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine)	2.50 %	Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose)	104.53 µM/kg/day	Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability)	25 %	Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution)	4.80 L/kg	Lombardo F, Berellini G, Obach RS
CL (Clearance)	23 mL/min/kg	Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma)	0.50 %	Lombardo F, Berellini G, Obach RS
t_half (Half-life)	4.40 hours	Lombardo F, Berellini G, Obach RS

Approvals:

Date	Agency	Company	Orphan
Aug. 1, 1984	FDA	CNTY LINE PHARMS

FDA Adverse Event Reporting System (Female)

MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Exposure during pregnancy	155.30	15.32	123	5873	136219	56149852
Pre-eclampsia	120.27	15.32	42	5954	8444	56277627
Caesarean section	107.21	15.32	46	5950	16045	56270026
Premature delivery	95.74	15.32	50	5946	27010	56259061
Premature baby	93.21	15.32	44	5952	19161	56266910
Maternal exposure during pregnancy	69.68	15.32	93	5903	189460	56096611
Foetal growth restriction	63.27	15.32	25	5971	7074	56278997
Hypertension	61.11	15.32	100	5896	244178	56041893
Patent ductus arteriosus	50.05	15.32	18	5978	3933	56282138
Premature labour	45.00	15.32	23	5973	11859	56274212
Haemangioma congenital	43.55	15.32	10	5986	436	56285635
Pregnancy	42.23	15.32	32	5964	33001	56253070
Foetal exposure during pregnancy	35.14	15.32	29	5967	33794	56252277
Hypotension	29.39	15.32	75	5921	250433	56035638
Low birth weight baby	29.31	15.32	14	5982	6244	56279827
Maternal drugs affecting foetus	28.85	15.32	13	5983	5080	56280991
Rheumatoid arthritis	27.58	15.32	4	5992	382600	55903471
HELLP syndrome	27.19	15.32	8	5988	928	56285143
Foetal death	25.13	15.32	14	5982	8573	56277498
Post transplant lymphoproliferative disorder	23.56	15.32	11	5985	4661	56281410
Gestational diabetes	23.19	15.32	13	5983	8051	56278020
Phaeochromocytoma	22.41	15.32	6	5990	493	56285578
Exomphalos	21.80	15.32	6	5990	547	56285524
Ultrasound uterus abnormal	20.93	15.32	4	5992	70	56286001
Dilatation intrahepatic duct acquired	20.84	15.32	6	5990	644	56285427
Blood pressure increased	19.69	15.32	46	5950	145130	56140941
Hyperkalaemia	18.68	15.32	25	5971	50840	56235231
Drug intolerance	18.54	15.32	3	5993	264815	56021256
Cardiac arrest	17.15	15.32	32	5964	86282	56199789
Abortion spontaneous	16.83	15.32	22	5974	43731	56242340
Red blood cell schistocytes present	15.71	15.32	4	5992	270	56285801
Kidney transplant rejection	15.50	15.32	8	5988	4205	56281866
Neuromuscular blockade	15.34	15.32	4	5992	297	56285774

FDA Adverse Event Reporting System (Male)

MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Premature baby	116.35	18.67	51	3470	18015	31675808
Foetal exposure during pregnancy	74.78	18.67	50	3471	40826	31652997
Low birth weight baby	73.35	18.67	28	3493	6942	31686881
Foetal disorder	72.24	18.67	17	3504	793	31693030
Neutropenia neonatal	64.45	18.67	15	3506	666	31693157
Foetal growth restriction	46.22	18.67	17	3504	3798	31690025
Congenital oesophageal anomaly	44.58	18.67	8	3513	93	31693730
Polyhydramnios	31.91	18.67	7	3514	237	31693586
Patent ductus arteriosus	30.63	18.67	12	3509	3181	31690642
Hypertension	29.82	18.67	52	3469	128048	31565775
Maternal exposure during pregnancy	29.46	18.67	13	3508	4643	31689180
Anhedonia	29.33	18.67	15	3506	7427	31686396
Neonatal respiratory distress	26.40	18.67	7	3514	532	31693291
Newborn persistent pulmonary hypertension	24.91	18.67	5	3516	109	31693714
Nephrogenic systemic fibrosis	24.88	18.67	11	3510	3944	31689879
Emotional distress	24.86	18.67	17	3504	14339	31679484
Injury	24.29	18.67	19	3502	19690	31674133
Fear	22.64	18.67	14	3507	9960	31683863
Neonatal cholestasis	22.41	18.67	4	3517	45	31693778
Ventricular septal defect	22.40	18.67	10	3511	3667	31690156
Cardiac arrest	21.80	18.67	37	3484	89025	31604798
Pyelocaliectasis	21.40	18.67	7	3514	1104	31692719
Renal injury	19.35	18.67	13	3508	10652	31683171

FDA Adverse Event Reporting System (Geriatric)

MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Exposure during pregnancy	137.82	15.17	95	7231	87622	70833496
Pre-eclampsia	96.35	15.17	33	7293	6452	70914666
Caesarean section	87.76	15.17	36	7290	11571	70909547
Hypertension	77.97	15.17	122	7204	295911	70625207
Premature labour	47.80	15.17	21	7305	7979	70913139
Maternal exposure during pregnancy	42.72	15.17	56	7270	115289	70805829
Hypotension	36.67	15.17	108	7218	404273	70516845
Cardiac arrest	32.78	15.17	59	7267	159775	70761343
Pregnancy	30.93	15.17	23	7303	23758	70897360
Kidney transplant rejection	28.95	15.17	16	7310	9945	70911173
Premature delivery	26.36	15.17	20	7306	21284	70899834
Phaeochromocytoma	25.87	15.17	7	7319	618	70920500
Foetal death	23.75	15.17	12	7314	6227	70914891
Anhedonia	23.70	15.17	16	7310	14197	70906921
Renal injury	21.91	15.17	16	7310	16078	70905040
Bradycardia	21.80	15.17	43	7283	124572	70796546
Foetal growth restriction	21.79	15.17	8	7318	1911	70919207
Nephrogenic systemic fibrosis	21.18	15.17	11	7315	6041	70915077
Mental status changes	20.84	15.17	29	7297	63072	70858046
Myocardial infarction	20.69	15.17	51	7275	171594	70749524
Dilatation intrahepatic duct acquired	20.60	15.17	6	7320	693	70920425
HELLP syndrome	20.47	15.17	6	7320	708	70920410
Fear	20.32	15.17	17	7309	20794	70900324
Cerebrovascular accident	19.87	15.17	45	7281	143425	70777693
Renal failure	19.52	15.17	53	7273	189017	70732101
Abortion spontaneous	18.67	15.17	18	7308	26461	70894657
Blood pressure increased	18.62	15.17	52	7274	188465	70732653
Skin induration	18.54	15.17	9	7317	4286	70916832
Rheumatoid arthritis	18.11	15.17	4	7322	291801	70629317
Premature baby	17.28	15.17	8	7318	3431	70917687
Red blood cell schistocytes present	17.24	15.17	5	7321	569	70920549
Cardiac failure congestive	17.12	15.17	41	7285	135416	70785702
Emotional distress	16.86	15.17	20	7306	37168	70883950
Angioedema	16.82	15.17	27	7299	66583	70854535
Cerebral haemorrhage	16.67	15.17	24	7302	53840	70867278
Coronary artery disease	16.63	15.17	26	7300	62710	70858408
Malignant hypertension	15.94	15.17	6	7320	1535	70919583
Post transplant lymphoproliferative disorder	15.53	15.17	11	7315	10534	70910584

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

Source	Code	Description
ATC	C07AG01	CARDIOVASCULAR SYSTEM BETA BLOCKING AGENTS BETA BLOCKING AGENTS Alpha and beta blocking agents
ATC	C07BG01	CARDIOVASCULAR SYSTEM BETA BLOCKING AGENTS BETA BLOCKING AGENTS AND THIAZIDES Alpha and beta blocking agents and thiazides
ATC	C07CG01	CARDIOVASCULAR SYSTEM BETA BLOCKING AGENTS BETA BLOCKING AGENTS AND OTHER DIURETICS Alpha and beta blocking agents and other diuretics
FDA MoA	N0000000161	Adrenergic beta-Antagonists
FDA EPC	N0000175556	beta-Adrenergic Blocker
MeSH PA	D018663	Adrenergic Agents
MeSH PA	D058668	Adrenergic alpha-1 Receptor Antagonists
MeSH PA	D000317	Adrenergic alpha-Antagonists
MeSH PA	D018674	Adrenergic Antagonists
MeSH PA	D000319	Adrenergic beta-Antagonists
MeSH PA	D000959	Antihypertensive Agents
MeSH PA	D002317	Cardiovascular Agents
MeSH PA	D018377	Neurotransmitter Agents
MeSH PA	D018373	Peripheral Nervous System Agents
MeSH PA	D013566	Sympathomimetics
CHEBI has role	CHEBI:35530	beta-adrenergic blockers
CHEBI has role	CHEBI:35674	antihypertensive drugs
CHEBI has role	CHEBI:37890	alpha-adrenergic receptor blockaders
CHEBI has role	CHEBI:66991	sympatholytic drug

Drug Use | Suggest Off label Use Form| |View source of the data|

Disease	Relation	SNOMED_ID	DOID
Hypertensive disorder	indication	38341003	DOID:10763
Angina pectoris	off-label use	194828000
Pheochromocytoma Adjunct Therapy	off-label use
Anuria	contraindication	2472002	DOID:2983
Bronchospasm	contraindication	4386001
Hypercholesterolemia	contraindication	13644009
Secondary angle-closure glaucoma	contraindication	21571006
Complete atrioventricular block	contraindication	27885002
Hypovolemia	contraindication	28560003
Dehydration	contraindication	34095006
Depressive disorder	contraindication	35489007
Hyperuricemia	contraindication	35885006	DOID:1920
Hypokalemia	contraindication	43339004
Low blood pressure	contraindication	45007003
Sinus bradycardia	contraindication	49710005
Systemic lupus erythematosus	contraindication	55464009	DOID:9074
Sympathectomy	contraindication	57071006
Hepatic failure	contraindication	59927004
Hypercalcemia	contraindication	66931009	DOID:12678
Hyperparathyroidism	contraindication	66999008	DOID:13543
Hypochloremic alkalosis	contraindication	70134007
Hepatic coma	contraindication	72836002	DOID:12550
Diabetes mellitus	contraindication	73211009	DOID:9351
Pulmonary emphysema	contraindication	87433001
Cardiogenic shock	contraindication	89138009
Hyponatremia	contraindication	89627008
Gout	contraindication	90560007	DOID:13189
Kidney disease	contraindication	90708001	DOID:557
Hypomagnesemia	contraindication	190855004
Partial atrioventricular block	contraindication	195039008
Decompensated cardiac failure	contraindication	195111005
Acute pancreatitis	contraindication	197456007	DOID:2913
Disease of liver	contraindication	235856003	DOID:409
Neonatal hyperbilirubinemia	contraindication	281610001
Intraoperative floppy iris syndrome	contraindication	418801006
Azotemia	contraindication	445009001

🐶 Veterinary Drug Use

None

🐶 Veterinary products

None

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation level	Dissociation constant	Type (acidic/basic)
pKa1	8.81	acidic
pKa2	12.65	acidic
pKa3	8.23	Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

Target	Class	Pharos	UniProt	Action	Type	Activity value (-log[M])	Bioact source	MoA source
Beta-1 adrenergic receptor	GPCR	P08588	ADRB1_HUMAN	ANTAGONIST	Ki	8.23	DRUG MATRIX	CHEMBL
Beta-2 adrenergic receptor	GPCR	P07550	ADRB2_HUMAN	ANTAGONIST	Ki	7.96	DRUG MATRIX	CHEMBL
Sigma non-opioid intracellular receptor 1	Membrane receptor	Q99720	SGMR1_HUMAN		Ki	6.12	DRUG MATRIX
Sodium-dependent noradrenaline transporter	Transporter	P23975	SC6A2_HUMAN		Ki	5.48	DRUG MATRIX
5-hydroxytryptamine receptor 1A	GPCR	P08908	5HT1A_HUMAN		Ki	6.65	DRUG MATRIX
5-hydroxytryptamine receptor 2B	GPCR	P41595	5HT2B_HUMAN		Ki	5.71	DRUG MATRIX
Sodium-dependent dopamine transporter	Transporter	Q01959	SC6A3_HUMAN		Ki	5.89	DRUG MATRIX
Cytochrome P450 2D6	Enzyme	P10635	CP2D6_HUMAN		IC50	6.10	DRUG MATRIX
Alpha-1D adrenergic receptor	GPCR	P25100	ADA1D_HUMAN	ANTAGONIST	Ki	7.64	DRUG MATRIX
Alpha-1B adrenergic receptor	GPCR		ADA1B_RAT		Ki	6.49	DRUG MATRIX
Alpha-1A adrenergic receptor	GPCR		ADA1A_RAT		IC50	7.24	CHEMBL
5-hydroxytryptamine receptor 1A	GPCR		5HT1A_RAT		IC50	6.41	CHEMBL
CAAX prenyl protease 1	Enzyme		STE24_YEAST		AC50	5.11	CHEMBL
CAAX prenyl protease 2	Enzyme		RCE1_YEAST		AC50	4.82	CHEMBL

External reference:

ID	Source
4019797	VUID
N0000147886	NUI
D00600	KEGG_DRUG
32780-64-6	SECONDARY_CAS_RN
4018799	VANDF
4019797	VANDF
C0022860	UMLSCUI
CHEBI:6343	CHEBI
CHEMBL429	ChEMBL_ID
DB00598	DRUGBANK_ID
CHEMBL1200323	ChEMBL_ID
D007741	MESH_DESCRIPTOR_UI
3869	PUBCHEM_CID
7207	IUPHAR_LIGAND_ID
3941	INN_ID
R5H8897N95	UNII
202693	RXNORM
11828	MMSL
201477	MMSL
4950	MMSL
d00016	MMSL
001839	NDDF
004368	NDDF
372750000	SNOMEDCT_US
46547007	SNOMEDCT_US
50627005	SNOMEDCT_US
CHEMBL1204165	ChEMBL_ID

Pharmaceutical products:

Product	Category	Ingredients	NDC	Form	Quantity	Route	Marketing	Label
Labetalol Hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	0143-9320	INJECTION	5 mg	INTRAVENOUS	ANDA	24 sections
Labetalol HCl in Sodium Chloride	HUMAN PRESCRIPTION DRUG LABEL	1	0143-9363	INJECTION	1 mg	INTRAVENOUS	NDA	24 sections
Labetalol HCl in Sodium Chloride	HUMAN PRESCRIPTION DRUG LABEL	1	0143-9363	INJECTION	1 mg	INTRAVENOUS	NDA	24 sections
Labetalol HCl in Sodium Chloride	HUMAN PRESCRIPTION DRUG LABEL	1	0143-9364	INJECTION	1 mg	INTRAVENOUS	NDA	24 sections
Labetalol HCl in Sodium Chloride	HUMAN PRESCRIPTION DRUG LABEL	1	0143-9364	INJECTION	1 mg	INTRAVENOUS	NDA	24 sections
Labetalol HCl in Sodium Chloride	HUMAN PRESCRIPTION DRUG LABEL	1	0143-9365	INJECTION	1 mg	INTRAVENOUS	NDA	24 sections
Labetalol HCl in Sodium Chloride	HUMAN PRESCRIPTION DRUG LABEL	1	0143-9365	INJECTION	1 mg	INTRAVENOUS	NDA	24 sections
Labetalol HCl in Dextrose	HUMAN PRESCRIPTION DRUG LABEL	1	0143-9366	INJECTION	1 mg	INTRAVENOUS	NDA	24 sections
Labetalol HCl in Dextrose	HUMAN PRESCRIPTION DRUG LABEL	1	0143-9366	INJECTION	1 mg	INTRAVENOUS	NDA	24 sections
Labetalol Hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	0143-9622	INJECTION	5 mg	INTRAVENOUS	ANDA	23 sections
Labetalol Hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	0143-9623	INJECTION	5 mg	INTRAVENOUS	ANDA	23 sections
Labetalol HCl	HUMAN PRESCRIPTION DRUG LABEL	1	0185-0010	TABLET, FILM COATED	100 mg	ORAL	ANDA	23 sections
Labetalol HCl	HUMAN PRESCRIPTION DRUG LABEL	1	0185-0117	TABLET, FILM COATED	200 mg	ORAL	ANDA	23 sections
Labetalol HCl	HUMAN PRESCRIPTION DRUG LABEL	1	0185-0118	TABLET, FILM COATED	300 mg	ORAL	ANDA	23 sections
Labetalol Hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	0409-2267	INJECTION, SOLUTION	5 mg	INTRAVENOUS	ANDA	12 sections
Labetalol Hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	0409-2339	INJECTION, SOLUTION	5 mg	INTRAVENOUS	ANDA	12 sections
Labetalol hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	0591-0605	TABLET, FILM COATED	100 mg	ORAL	ANDA	22 sections
Labetalol hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	0591-0606	TABLET, FILM COATED	200 mg	ORAL	ANDA	22 sections
Labetalol hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	0591-0607	TABLET, FILM COATED	300 mg	ORAL	ANDA	22 sections
Labetalol HCL	HUMAN PRESCRIPTION DRUG LABEL	1	0615-8130	TABLET, FILM COATED	100 mg	ORAL	ANDA	22 sections
Labetalol HCL	HUMAN PRESCRIPTION DRUG LABEL	1	0615-8131	TABLET, FILM COATED	200 mg	ORAL	ANDA	22 sections
Labetalol Hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	0641-6252	INJECTION	5 mg	INTRAVENOUS	NDA	26 sections
Labetalol hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	0904-5928	TABLET, FILM COATED	100 mg	ORAL	ANDA	22 sections
Labetalol hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	0904-5929	TABLET, FILM COATED	200 mg	ORAL	ANDA	22 sections
Labetalol hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	0904-5930	TABLET, FILM COATED	300 mg	ORAL	ANDA	22 sections
Labetalol Hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	0904-7109	TABLET, FILM COATED	100 mg	ORAL	ANDA	19 sections
Labetalol Hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	0904-7110	TABLET, FILM COATED	200 mg	ORAL	ANDA	19 sections
Labetalol Hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	0904-7111	TABLET, FILM COATED	300 mg	ORAL	ANDA	19 sections
Labetalol	HUMAN PRESCRIPTION DRUG LABEL	1	10135-641	TABLET, FILM COATED	100 mg	ORAL	ANDA	23 sections
Labetalol	HUMAN PRESCRIPTION DRUG LABEL	1	10135-642	TABLET, FILM COATED	200 mg	ORAL	ANDA	23 sections