Details
| Stereochemistry | MIXED |
| Molecular Formula | C19H24N2O3.ClH |
| Molecular Weight | 364.866 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 0 / 2 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.CC(CCC1=CC=CC=C1)NCC(O)C2=CC=C(O)C(=C2)C(N)=O
InChI
InChIKey=WQVZLXWQESQGIF-UHFFFAOYSA-N
InChI=1S/C19H24N2O3.ClH/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);1H
| 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 |
| Molecular Formula | ClH |
| Molecular Weight | 36.461 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
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 |
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 |
|---|---|---|---|---|
| likely |
Drug as victim
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
| likely | ||||
| 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 |
|
| Letter: Emergency treatment of hypertensive crisis following clonidine withdrawal. | 1976 May 29 |
|
| Pharmacological basis for antihypertensive effects of intravenous labetalol. | 1977 Jan |
|
| Hemodynamic collapse following labetalol administration in preeclampsia. | 1992 Feb |
|
| Hypersensitivity immune reaction as a mechanism for dilevalol-associated hepatitis. | 1992 Jul-Aug |
|
| Labetalol decreases cerebral perfusion pressure without negatively affecting cerebral blood flow in hypertensive gravidas. | 2002 |
|
| 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 |
|
| Electrocardiographic changes associated with beta-blocker toxicity. | 2002 Dec |
|
| Partial agonistic activity of labetalol, the arylethanolamine, on beta 3-adrenoceptors in the guinea-pig gastric fundus. | 2002 Feb |
|
| [Nuclear medicine diagnosis of pheochromocytoma with metaiodobenzylguanidine]. | 2002 Jul |
|
| Labetalol for prophylactic treatment of intractable migraine during pregnancy. | 2002 Jul-Aug |
|
| 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 |
|
| [Influence of different pharmacological agents in the ex vivo proliferation of mesothelial cells obtained from the peritoneal effluent of patients treated with peritoneal dialysis]. | 2003 |
|
| Scleroderma renal crisis sine scleroderma during pregnancy. | 2003 |
|
| Refractory hypotension during caesarean section following pre-operative administration of anti-hypertensive agents. | 2003 Apr |
|
| Left ventricular diastolic function in pregnancy-induced hypertension. | 2003 Apr |
|
| Spectrophotometric determination of labetalol in pharmaceutical preparations and spiked human urine. | 2003 Apr |
|
| Multiple Bier blocks with labetalol for complex regional pain syndrome refractory to other treatments. | 2003 Apr |
|
| The effect of remifentanil on seizure duration and acute hemodynamic responses to electroconvulsive therapy. | 2003 Apr |
|
| Clonidine facilitates controlled hypotension in adolescent children. | 2003 Apr |
|
| Improvement of peak shape and separation performance of beta-blockers in conventional reversed-phase columns using solvent modifiers. | 2003 Aug |
|
| Labetalol treatment enhances the attenuation of tobacco withdrawal symptoms by nicotine in abstinent smokers. | 2003 Dec |
|
| Managing hypertension in patients with stroke. Are you prepared for labetalol infusion? | 2003 Jun |
|
| Agonist actions of "beta-blockers" provide evidence for two agonist activation sites or conformations of the human beta1-adrenoceptor. | 2003 Jun |
|
| Was case report a case of unrecognized local anesthetic toxicity? | 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 |
|
| Fatality from administration of labetalol and crushed extended-release nifedipine. | 2003 Oct |
|
| Clinical review: the management of hypertensive crises. | 2003 Oct |
|
| Hydralazine for treatment of severe hypertension in pregnancy: meta-analysis. | 2003 Oct 25 |
|
| [Toxicologic analysis of some adrenergic-beta blockers in the diagnosis of intoxications]. | 2003 Oct-Dec |
|
| 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 |
|
| Hyponatremic hypertensive syndrome (HHS) in an 18-month old-child presenting as malignant hypertension: a case report. | 2004 Apr 27 |
|
| In vitro effects of antihypertensive drugs on thromboxane agonist (U46619)-induced vasoconstriction in human internal mammary artery. | 2004 Aug |
|
| Chiral separation of labetalol stereoisomers in human plasma by capillary electrophoresis. | 2004 Feb 20 |
|
| 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
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
Fri Dec 15 16:13:10 GMT 2023
by
admin
on
Fri Dec 15 16:13:10 GMT 2023
|
| Record UNII |
1GEV3BAW9J
|
| Record Status |
Validated (UNII)
|
| Record Version |
|
-
Download
| Name | Type | Language | ||
|---|---|---|---|---|
|
Official Name | English | ||
|
Common Name | English | ||
|
Brand Name | English | ||
|
Common Name | English | ||
|
Brand Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Code | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Systematic Name | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English |
| Classification Tree | Code System | Code | ||
|---|---|---|---|---|
|
NCI_THESAURUS |
C29713
Created by
admin on Fri Dec 15 16:13:10 GMT 2023 , Edited by admin on Fri Dec 15 16:13:10 GMT 2023
|
| Code System | Code | Type | Description | ||
|---|---|---|---|---|---|
|
m6647
Created by
admin on Fri Dec 15 16:13:10 GMT 2023 , Edited by admin on Fri Dec 15 16:13:10 GMT 2023
|
PRIMARY | Merck Index | ||
|
202693
Created by
admin on Fri Dec 15 16:13:10 GMT 2023 , Edited by admin on Fri Dec 15 16:13:10 GMT 2023
|
PRIMARY | RxNorm | ||
|
1GEV3BAW9J
Created by
admin on Fri Dec 15 16:13:10 GMT 2023 , Edited by admin on Fri Dec 15 16:13:10 GMT 2023
|
PRIMARY | |||
|
C63578
Created by
admin on Fri Dec 15 16:13:10 GMT 2023 , Edited by admin on Fri Dec 15 16:13:10 GMT 2023
|
PRIMARY | |||
|
251-211-1
Created by
admin on Fri Dec 15 16:13:10 GMT 2023 , Edited by admin on Fri Dec 15 16:13:10 GMT 2023
|
PRIMARY | |||
|
32780-64-6
Created by
admin on Fri Dec 15 16:13:10 GMT 2023 , Edited by admin on Fri Dec 15 16:13:10 GMT 2023
|
PRIMARY | |||
|
DBSALT000320
Created by
admin on Fri Dec 15 16:13:10 GMT 2023 , Edited by admin on Fri Dec 15 16:13:10 GMT 2023
|
PRIMARY | |||
|
DTXSID0044654
Created by
admin on Fri Dec 15 16:13:10 GMT 2023 , Edited by admin on Fri Dec 15 16:13:10 GMT 2023
|
PRIMARY | |||
|
290312
Created by
admin on Fri Dec 15 16:13:10 GMT 2023 , Edited by admin on Fri Dec 15 16:13:10 GMT 2023
|
PRIMARY | |||
|
CHEMBL429
Created by
admin on Fri Dec 15 16:13:10 GMT 2023 , Edited by admin on Fri Dec 15 16:13:10 GMT 2023
|
PRIMARY | |||
|
71412
Created by
admin on Fri Dec 15 16:13:10 GMT 2023 , Edited by admin on Fri Dec 15 16:13:10 GMT 2023
|
PRIMARY | |||
|
1GEV3BAW9J
Created by
admin on Fri Dec 15 16:13:10 GMT 2023 , Edited by admin on Fri Dec 15 16:13:10 GMT 2023
|
PRIMARY | |||
|
1356654
Created by
admin on Fri Dec 15 16:13:10 GMT 2023 , Edited by admin on Fri Dec 15 16:13:10 GMT 2023
|
PRIMARY | |||
|
SUB02844MIG
Created by
admin on Fri Dec 15 16:13:10 GMT 2023 , Edited by admin on Fri Dec 15 16:13:10 GMT 2023
|
PRIMARY | |||
|
100000089827
Created by
admin on Fri Dec 15 16:13:10 GMT 2023 , Edited by admin on Fri Dec 15 16:13:10 GMT 2023
|
PRIMARY |
| Related Record | Type | Details | ||
|---|---|---|---|---|
|
|
PARENT -> SALT/SOLVATE |
| Related Record | Type | Details | ||
|---|---|---|---|---|
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
||
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
| Related Record | Type | Details | ||
|---|---|---|---|---|
|
|
ACTIVE MOIETY |