Details
Stereochemistry | MIXED |
Molecular Formula | C19H24N2O3 |
Molecular Weight | 328.4055 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 0 / 2 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CC(CCC1=CC=CC=C1)NCC(O)C2=CC=C(O)C(=C2)C(N)=O
InChI
InChIKey=SGUAFYQXFOLMHL-UHFFFAOYSA-N
InChI=1S/C19H24N2O3/c1-13(7-8-14-5-3-2-4-6-14)21-12-18(23)15-9-10-17(22)16(11-15)19(20)24/h2-6,9-11,13,18,21-23H,7-8,12H2,1H3,(H2,20,24)
Molecular Formula | C19H24N2O3 |
Molecular Weight | 328.4055 |
Charge | 0 |
Count |
|
Stereochemistry | MIXED |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 2 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
DescriptionSources: http://www.accessdata.fda.gov/drugsatfda_docs/anda/98/74787_Labetalol%20Hydrochloride_Prntlbl.pdfCurator's Comment: description was created based on several sources, including
http://www.rxlist.com/trandate-drug.htm
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/anda/98/74787_Labetalol%20Hydrochloride_Prntlbl.pdf
Curator's Comment: description was created based on several sources, including
http://www.rxlist.com/trandate-drug.htm
Labetalol is a blocker of both alpha- and beta-adrenergic receptors that is used as an antihypertensive. It may be used alone or in combination with other antihypertensive agents, especially thiazide and loop diuretics. The capacity of labetalol HCl to block alpha receptors in man has been demonstrated by attenuation of the pressor effect of phenylephrine and by a significant reduction of the pressor response caused by immersing the hand in ice-cold water ("cold-pressor test"). Labetalol HCl's beta1-receptor blockade in man was demonstrated by a small decrease in the resting heart rate, attenuation of tachycardia produced by isoproterenol or exercise, and by attenuation of the reflex tachycardia to the hypotension produced by amyl nitrite. Beta2-receptor blockade was demonstrated by inhibition of the isoproterenol-induced fall in diastolic blood pressure. Both the alpha- and beta-blocking actions of orally administered labetalol HCl contribute to a decrease in blood pressure in hypertensive patients. Labetalol HCl consistently, in dose-related fashion, blunted increases in exercise-induced blood pressure and heart rate, and in their double product. The pulmonary circulation during exercise was not affected by labetalol HCl dosing. Single oral doses of labetalol HCl administered to patients with coronary artery disease had no significant effect on sinus rate, intraventricular conduction, or QRS duration. The atrioventricular (A-V) conduction time was modestly prolonged in two of seven patients. In another study, IV labetalol HCl slightly prolonged A-V nodal conduction time and atrial effective refractory period with only small changes in heart rate. The metabolism of labetalol is mainly through conjugation to glucuronide metabolites. These metabolites are present in plasma and are excreted in the urine and, via the bile, into the feces. Approximately 55% to 60% of a dose appears in the urine as conjugates or unchanged labetalol within the first 24 hours of dosing. Labetalol has been shown to cross the placental barrier in humans. Only negligible amounts of the drug crossed the blood-brain barrier in animal studies. Labetalol is approximately 50% protein bound. Neither hemodialysis nor peritoneal dialysis removes a significant amount of labetalol HCl from the general circulation.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2331074 Sources: https://www.ncbi.nlm.nih.gov/pubmed/6355664 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | LABETALOL HYDROCHLORIDE Approved UseLabetalol hydrochloride tablets, USP are indicated in the management of hypertension. Labetalol hydrochloride tablets, USP may be used alone or in combination with other antihypertensive agents, especially thiazide and loop diuretics. Launch Date1988 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
72.4 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/16225568/ |
100 mg 2 times / 2 days steady-state, oral dose: 100 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
LABETALOL plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
571 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/16225568/ |
100 mg 2 times / 2 days steady-state, oral dose: 100 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
LABETALOL plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
3000 mg single, oral (max) Highest studied dose |
unhealthy, 18-81 n = 32 Health Status: unhealthy Condition: Hypertension Age Group: 18-81 Sex: M+F Population Size: 32 Sources: |
Disc. AE: Orthostatic hypotension... AEs leading to discontinuation/dose reduction: Orthostatic hypotension Sources: |
14 g single, oral (max) Overdose Dose: 14 g Route: oral Route: single Dose: 14 g Co-administed with:: alcohol, p.o Sources: |
healthy, 38 n = 1 Health Status: healthy Age Group: 38 Sex: F Population Size: 1 Sources: |
Disc. AE: Acute renal failure... AEs leading to discontinuation/dose reduction: Acute renal failure Sources: |
1200 mg 2 times / day multiple, oral (total daily dose) Recommended Dose: 1200 mg, 2 times / day Route: oral Route: multiple Dose: 1200 mg, 2 times / day Sources: |
unhealthy Health Status: unhealthy Condition: Hypertension Sources: |
|
400 mg 2 times / day multiple, oral (max) Recommended Dose: 400 mg, 2 times / day Route: oral Route: multiple Dose: 400 mg, 2 times / day Sources: Page: p.5 |
unhealthy Health Status: unhealthy Condition: Hypertension Sources: Page: p.5 |
Disc. AE: Cardiac failure... Other AEs: Hepatocellular injury, Congestive heart failure... AEs leading to discontinuation/dose reduction: Cardiac failure Other AEs:Hepatocellular injury (severe, rare) Sources: Page: p.5Congestive heart failure |
300 mg single, intravenous (total) Studied dose Dose: 300 mg Route: intravenous Route: single Dose: 300 mg Sources: Page: p.14 |
unhealthy Health Status: unhealthy Condition: Hypertension Sources: Page: p.14 |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Orthostatic hypotension | Disc. AE | 3000 mg single, oral (max) Highest studied dose |
unhealthy, 18-81 n = 32 Health Status: unhealthy Condition: Hypertension Age Group: 18-81 Sex: M+F Population Size: 32 Sources: |
Acute renal failure | Disc. AE | 14 g single, oral (max) Overdose Dose: 14 g Route: oral Route: single Dose: 14 g Co-administed with:: alcohol, p.o Sources: |
healthy, 38 n = 1 Health Status: healthy Age Group: 38 Sex: F Population Size: 1 Sources: |
Congestive heart failure | 400 mg 2 times / day multiple, oral (max) Recommended Dose: 400 mg, 2 times / day Route: oral Route: multiple Dose: 400 mg, 2 times / day Sources: Page: p.5 |
unhealthy Health Status: unhealthy Condition: Hypertension Sources: Page: p.5 |
|
Cardiac failure | Disc. AE | 400 mg 2 times / day multiple, oral (max) Recommended Dose: 400 mg, 2 times / day Route: oral Route: multiple Dose: 400 mg, 2 times / day Sources: Page: p.5 |
unhealthy Health Status: unhealthy Condition: Hypertension Sources: Page: p.5 |
Hepatocellular injury | severe, rare | 400 mg 2 times / day multiple, oral (max) Recommended Dose: 400 mg, 2 times / day Route: oral Route: multiple Dose: 400 mg, 2 times / day Sources: Page: p.5 |
unhealthy Health Status: unhealthy Condition: Hypertension Sources: Page: p.5 |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/anda/98/75133_Labetalol%20Hydrochloride.pdf Page: 5.0 |
likely |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
likely | ||||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/anda/98/75133_Labetalol%20Hydrochloride.pdf Page: 5.0 |
likely | |||
minor | ||||
no | ||||
no | ||||
no | ||||
yes | ||||
yes |
PubMed
Title | Date | PubMed |
---|---|---|
Labetalol (AH5158), a competitive alpha- and beta-receptor blocking drug, in the management of hypertension. | 1976 Aug |
|
Drugs in pregnancy. Antihypertensives. | 2001 Dec |
|
Comparative hemodynamic effects of urapidil and labetalol after electroconvulsive therapy. | 2001 Dec |
|
Drug wastage contributes significantly to the cost of routine anesthesia care. | 2001 Nov |
|
[Hypertension emergency during surgery of renal carcinoma associated with non-diagnosed pheochromocytoma]. | 2001 Sep |
|
Labetalol decreases cerebral perfusion pressure without negatively affecting cerebral blood flow in hypertensive gravidas. | 2002 |
|
Liddle syndrome in a newborn infant. | 2002 Aug |
|
Postpartum eclampsia. | 2002 Aug 1 |
|
Factors influencing acute ischaemia-induced renal hypertension in rats. | 2002 Dec |
|
Cardiac arrest after labetalol and metoclopramide administration in a patient with scleroderma. | 2002 Dec |
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Electrocardiographic changes associated with beta-blocker toxicity. | 2002 Dec |
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Partial agonistic activity of labetalol, the arylethanolamine, on beta 3-adrenoceptors in the guinea-pig gastric fundus. | 2002 Feb |
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Elevated vascular resistance after labetalol during resection of a pheochromocytoma (brief report). | 2002 Feb |
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Remifentanil provides hemodynamic stability and faster awakening time in transsphenoidal surgery. | 2002 Jan |
|
Pheochromocytoma. | 2002 Jan-Feb |
|
[Nuclear medicine diagnosis of pheochromocytoma with metaiodobenzylguanidine]. | 2002 Jul |
|
Labetalol for prophylactic treatment of intractable migraine during pregnancy. | 2002 Jul-Aug |
|
Hepatic sinusoidal vasodilators improve transplanted cell engraftment and ameliorate microcirculatory perturbations in the liver. | 2002 Jun |
|
Vanillylamide-based propanolamine derivative displays alpha/beta-adrenoceptor blocking and vasodilating properties. | 2002 Jun |
|
Pemoline ingestion in children: a report of five cases and review of the literature. | 2002 Mar |
|
Labetalol-induced hepatitis in a patient with chronic hepatitis B infection. | 2002 Mar-Apr |
|
Acute and chronic hypertensive headache and hypertensive encephalopathy. | 2002 May |
|
The effect of antihypertensive drugs on the fetus. | 2002 May |
|
[beta-Adrenergic receptor blockers--a group of chiral drugs: different effects of each enantiomer]. | 2002 May |
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Early anti-remodeling effect of labetalol in the congestive heart failure model induced by aortic constriction in the guinea pig. | 2002 May |
|
Spectrofluorometric determination of labetolol in pharmaceutical preparations and spiked human urine through the formation of coumarin derivative. | 2002 Nov 7 |
|
Comprehensive management of hypertensive emergencies and urgencies. | 2002 Nov-Dec |
|
[Influence of labetalol on the resistance of human fetoplacental vessels in perfusion in vitro]. | 2002 Sep |
|
Short-term treatment of severe hypertension of pregnancy: prospective comparison of nicardipine and labetalol. | 2002 Sep |
|
Scleroderma renal crisis sine scleroderma during pregnancy. | 2003 |
|
Refractory hypotension during caesarean section following pre-operative administration of anti-hypertensive agents. | 2003 Apr |
|
Spectrophotometric determination of labetalol in pharmaceutical preparations and spiked human urine. | 2003 Apr |
|
Improvement of peak shape and separation performance of beta-blockers in conventional reversed-phase columns using solvent modifiers. | 2003 Aug |
|
Managing hypertension in patients with stroke. Are you prepared for labetalol infusion? | 2003 Jun |
|
Community-based thrombolytic therapy of acute ischemic stroke in Helsinki. | 2003 Jun |
|
Remifentanil for intraoperative analgesia during the endoscopic surgical treatment of pituitary lesions. | 2003 Mar |
|
Acute myocardial infarction as a complication of clonidine withdrawal. | 2003 Nov |
|
[Posterior reversible encephalopathy syndrome]. | 2003 Nov-Dec |
|
Enantioselective determination of arotinolol in human plasma by HPLC using teicoplanin chiral stationary phase. | 2003 Oct |
|
A survey of Canadian practitioners regarding the management of the hypertensive disorders of pregnancy. | 2004 |
|
Very low-dose spinal anesthesia for cesarean section in a morbidly obese preeclamptic patient and its potential implications. | 2004 Apr |
|
Dexmedetomidine for awake carotid endarterectomy: efficacy, hemodynamic profile, and side effects. | 2004 Apr |
|
Simultaneous determination of thirteen beta-blockers and one metabolite by gradient high-performance liquid chromatography with photodiode-array UV detection. | 2004 Apr 20 |
|
In vitro effects of antihypertensive drugs on thromboxane agonist (U46619)-induced vasoconstriction in human internal mammary artery. | 2004 Aug |
|
Periprocedural hypertension: current concepts in management for the vascular surgeon. | 2004 Jul-Aug |
|
[Protective effect of alpha beta-blockers on hypertensive target-organ damage]. | 2004 Mar |
|
Polymeric alkenoxy amino acid surfactants: II. Chiral separations of beta-blockers with multiple stereogenic centers. | 2004 Mar |
|
Effect of beta-adrenergic antagonists on bioluminescence control in three species of brittlestars (Echinodermata: Ophiuroidea). | 2004 May |
|
[Surgery to save body-packers]. | 2004 May |
|
Severe hypertension and massive proteinuria in a newborn with renal artery stenosis. | 2004 May |
Patents
Sample Use Guides
The recommended initial dosage is 100 mg twice daily whether used alone or added to a diuretic regimen. After 2 or 3 days, using standing blood pressure as an indicator, dosage may be titrated in increments of 100 mg b.i.d. every 2 or 3 days. The usual maintenance dosage of labetalol HCl is between 200 and 400 mg twice daily.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/2856060
Curator's Comment: The effects of the alpha-beta-adrenergic antagonist labetalol on the activation of human platelets by adrenaline and other aggregating stimuli have been investigated. Labetalol inhibited platelet aggregation and secretion induced by collagen and the second phase of aggregation caused by ADP, platelet activating factor, adrenaline and ionophore A23187.
Unknown
Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 17:53:12 GMT 2023
by
admin
on
Sat Dec 16 17:53:12 GMT 2023
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Record UNII |
R5H8897N95
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Record Status |
Validated (UNII)
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Record Version |
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LIVERTOX |
NBK547846
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NDF-RT |
N0000175556
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WHO-ATC |
C07BG01
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WHO-VATC |
QC07CG01
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WHO-VATC |
QC07BG01
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WHO-ATC |
C07CG01
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WHO-ATC |
C07AG01
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WHO-VATC |
QC07AG01
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NDF-RT |
N0000000161
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NCI_THESAURUS |
C72900
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CHEMBL429
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253-258-3
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LABETALOL
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3869
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m6647
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Labetalol
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R5H8897N95
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D007741
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167638
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7207
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100000083080
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6185
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3941
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36894-69-6
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SUB08382MIG
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R5H8897N95
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1531
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DTXSID2023191
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6537
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6343
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C29146
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DB00598
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ACTIVE MOIETY |
Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Biological Half-life | PHARMACOKINETIC |
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Volume of Distribution | PHARMACOKINETIC |
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