Labetalol

Labetalol
Clinical data
Pronunciation/ləˈbɛtəlɔːl/
Trade namesNormodyne, Trandate, others
Other namesIbidomide; AH-5158; SCH-19927
AHFS/Drugs.comMonograph
MedlinePlusa685034
License data
Pregnancy
category
  • AU: C
Routes of
administration		By mouth, intravenous
ATC code
Legal status
Legal status
  • AU: S4 (Prescription only)
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability25% (11–86%)[1][2][3]
Protein binding50%[1][3]
MetabolismMainly conjugation via glucuronidation[1][2][3]
Metabolites• Glucuronide conjugates[2]
Elimination half-lifeOral: 6–8 hours[1][2][3]
IVTooltip Intravenous infusion: 5.52 hours[2]
Duration of action8–12 hours[1]
ExcretionUrine (55–60% as conjugates or unchanged within 24 hours)[1]
Identifiers
IUPAC name
  • (RS)-2-Hydroxy-5-[1-hydroxy-2-[(4-phenylbutan-2-yl)amino]ethyl]benzamide
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.048.401
Chemical and physical data
FormulaC19H24N2O3
Molar mass328.412 g·mol−1
3D model (JSmol)
ChiralityRacemic mixture
SMILES
  • c1ccccc1CCC(C)NCC(O)c2ccc(O)c(C(=O)N)c2
InChI
  • 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) Y
  • Key:SGUAFYQXFOLMHL-UHFFFAOYSA-N Y
  (verify)

Labetalol is a medication used to treat high blood pressure and in long term management of angina.[4][5] This includes essential hypertension, hypertensive emergencies, and hypertension of pregnancy.[5] In essential hypertension it is generally less preferred than a number of other blood pressure medications.[4] It can be given by mouth or by injection into a vein.[4]

Common side effects include low blood pressure with standing, dizziness, feeling tired, and nausea.[4] Serious side effects may include low blood pressure, liver problems, heart failure, and bronchospasm.[4] Use appears safe in the latter part of pregnancy and it is not expected to cause problems during breastfeeding.[5][6] It works by blocking the activation of β- and α-adrenergic receptors.[4]

Labetalol was patented in 1966 and came into medical use in 1977.[7] It is available as a generic medication.[5] In 2022, it was the 215th most commonly prescribed medication in the United States, with more than 1 million prescriptions.[8][9]

  1. ^ a b c d e f Cite error: The named reference :0 was invoked but never defined (see the help page).
  2. ^ a b c d e MacCarthy EP, Bloomfield SS (1983). "Labetalol: a review of its pharmacology, pharmacokinetics, clinical uses and adverse effects". Pharmacotherapy. 3 (4): 193–219. doi:10.1002/j.1875-9114.1983.tb03252.x. PMID 6310529.
  3. ^ a b c d Cite error: The named reference DrugBank was invoked but never defined (see the help page).
  4. ^ a b c d e f "Labetalol Hydrochloride Monograph for Professionals". Drugs.com. American Society of Health-System Pharmacists. Retrieved 3 March 2019.
  5. ^ a b c d British national formulary : BNF 76 (76 ed.). Pharmaceutical Press. 2018. pp. 147–148. ISBN 9780857113382.
  6. ^ "Labetalol Use During Pregnancy". Drugs.com. Retrieved 11 March 2019.
  7. ^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 463. ISBN 9783527607495.
  8. ^ "The Top 300 of 2022". ClinCalc. Archived from the original on 30 August 2024. Retrieved 30 August 2024.
  9. ^ "Labetalol Drug Usage Statistics, United States, 2013 - 2022". ClinCalc. Retrieved 30 August 2024.
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