Labetalol
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MedKoo CAT#: 598182

CAS#: 36894-69-6 (free base)

Description: Labetalol is a mixed alpha/beta adrenergic antagonist that is used to treat high blood pressure. It can be given intravenously in severe hypertensive situations, or by mouth for long term hypertension management. Studies suggest that the pharmacokinetics of labetalol are significantly affected by the common CYP2C19 polymorphisms.


Chemical Structure

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Labetalol
CAS# 36894-69-6 (free base)

Theoretical Analysis

MedKoo Cat#: 598182
Name: Labetalol
CAS#: 36894-69-6 (free base)
Chemical Formula: C19H24N2O3
Exact Mass: 328.1787
Molecular Weight: 328.41
Elemental Analysis: C, 69.49; H, 7.37; N, 8.53; O, 14.61

Price and Availability

Size Price Availability Quantity
1.0g USD 250.0 2 Weeks
2.0g USD 450.0 2 Weeks
5.0g USD 850.0 2 Weeks
10.0g USD 1450.0 2 Weeks
25.0g USD 2450.0 2 Weeks
50.0g USD 3850.0 2 Weeks
Bulk inquiry

Related CAS #: 32780-64-6 (HCl)   36894-69-6 (free base)    

Synonym: Labetalol, Normodyne, Trandate, Albetol, Apo-Labetalol, Dilevalol

IUPAC/Chemical Name: 2-hydroxy-5-(1-hydroxy-2-((4-phenylbutan-2-yl)amino)ethyl)benzamide

InChi Key: SGUAFYQXFOLMHL-UHFFFAOYSA-N

InChi Code: 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)

SMILES Code: O=C(N)C1=CC(C(O)CNC(C)CCC2=CC=CC=C2)=CC=C1O

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >3 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Preparing Stock Solutions

The following data is based on the product molecular weight 328.41 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL

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1: Lang Y, Fu F, Sun D, Xi C, Chen F. Labetalol Prevents Intestinal Dysfunction Induced by Traumatic Brain Injury. PLoS One. 2015 Jul 17;10(7):e0133215. doi: 10.1371/journal.pone.0133215. eCollection 2015. PubMed PMID: 26186619; PubMed Central PMCID: PMC4505891.

2: Fischer JH, Sarto GE, Hardman J, Endres L, Jenkins TM, Kilpatrick SJ, Jeong H, Geller S, Deyo K, Fischer PA, Rodvold KA. Influence of gestational age and body weight on the pharmacokinetics of labetalol in pregnancy. Clin Pharmacokinet. 2014 Apr;53(4):373-83. doi: 10.1007/s40262-013-0123-0. PubMed PMID: 24297680; PubMed Central PMCID: PMC4310214.

3: Liu-DeRyke X, Levy PD, Parker D Jr, Coplin W, Rhoney DH. A prospective evaluation of labetalol versus nicardipine for blood pressure management in patients with acute stroke. Neurocrit Care. 2013 Aug;19(1):41-7. doi: 10.1007/s12028-013-9863-9. PubMed PMID: 23760911.

4: Chan SW, Hu M, Ko SS, Tam CW, Fok BS, Yin OQ, Chow MS, Tomlinson B. CYP2C19 genotype has a major influence on labetalol pharmacokinetics in healthy male Chinese subjects. Eur J Clin Pharmacol. 2013 Apr;69(4):799-806. doi: 10.1007/s00228-012-1428-x. Epub 2012 Oct 23. PubMed PMID: 23090703.

5: Peacock WF, Varon J, Baumann BM, Borczuk P, Cannon CM, Chandra A, Cline DM, Diercks D, Hiestand B, Hsu A, Jois-Bilowich P, Kaminski B, Levy P, Nowak RM, Schrock JW. CLUE: a randomized comparative effectiveness trial of IV nicardipine versus labetalol use in the emergency department. Crit Care. 2011;15(3):R157. doi: 10.1186/cc10289. Epub 2011 Jun 27. PubMed PMID: 21707983; PubMed Central PMCID: PMC3219031.

6: Castiella A, Iglesias U, Zapata E, Zubiaurre L, Iribarren A. [Toxic hepatocellular hepatitis due to labetalol]. Gastroenterol Hepatol. 2015 May;38(5):326-7. doi: 10.1016/j.gastrohep.2014.06.004. Epub 2014 Jul 26. Spanish. PubMed PMID: 25073680.

7: Laha B, Hazra A. Medication error report: Intrathecal administration of labetalol during obstetric anesthesia. Indian J Pharmacol. 2015 Jul-Aug;47(4):456-8. doi: 10.4103/0253-7613.161278. PubMed PMID: 26288484; PubMed Central PMCID: PMC4527074.

8: Malesker MA, Hilleman DE. Intravenous labetalol compared with intravenous nicardipine in the management of hypertension in critically ill patients. J Crit Care. 2012 Oct;27(5):528.e7-14. doi: 10.1016/j.jcrc.2011.12.005. Epub 2012 Feb 1. PubMed PMID: 22300487.

9: Gómez Torrijos E, García Rodríguez C, Sánchez Caminero MP, Castro Jiménez A, García Rodríguez R, Feo-Brito F. First case report of acute generalized exanthematous pustulosis due to labetalol. J Investig Allergol Clin Immunol. 2015;25(2):148-9. PubMed PMID: 25997315.

10: MacCarthy EP, Bloomfield SS. Labetalol: a review of its pharmacology, pharmacokinetics, clinical uses and adverse effects. Pharmacotherapy. 1983 Jul-Aug;3(4):193-219. Review. PubMed PMID: 6310529.

11: McGuinness N, Cording V. Raynaud's phenomenon of the nipple associated with labetalol use. J Hum Lact. 2013 Feb;29(1):17-9. doi: 10.1177/0890334412467509. Epub 2012 Dec 4. PubMed PMID: 23212937.

12: Thomas CA, Moffett BS, Wagner JL, Mott AR, Feig DI. Safety and efficacy of intravenous labetalol for hypertensive crisis in infants and small children. Pediatr Crit Care Med. 2011 Jan;12(1):28-32. doi: 10.1097/PCC.0b013e3181e328d8. PubMed PMID: 20495503.

13: Carvalho TM, Cavalli Rde C, Cunha SP, de Baraldi CO, Marques MP, Antunes NJ, Godoy AL, Lanchote VL. Influence of gestational diabetes mellitus on the stereoselective kinetic disposition and metabolism of labetalol in hypertensive patients. Eur J Clin Pharmacol. 2011 Jan;67(1):55-61. doi: 10.1007/s00228-010-0896-0. Epub 2010 Sep 17. PubMed PMID: 20848091.

14: Nooij LS, Visser S, Meuleman T, Vos P, Roelofs R, de Groot CJ. The optimal treatment of severe hypertension in pregnancy: update of the role of nicardipine. Curr Pharm Biotechnol. 2014;15(1):64-9. PubMed PMID: 24720593.

15: Labetalol and hydrochlorothiazide in hypertension. Labetalol/Hydrochlorothiazide Multicenter Study Group. Clin Pharmacol Ther. 1985 Jul;38(1):24-7. PubMed PMID: 2860990.

16: Immanni S, Khan EI, Staunton M. Hypoglycaemia secondary to labetalol infusion. J Coll Physicians Surg Pak. 2011 May;21(5):297-8. doi: 05.2011/JCPSP.297298. PubMed PMID: 21575539.

17: Pugsley DJ, Nassim M, Armstrong BK, Beilin L. A controlled trial of labetalol (Trandate), propranolol and placebo in the management of mild to moderate hypertension. Br J Clin Pharmacol. 1979 Jan;7(1):63-8. PubMed PMID: 367410; PubMed Central PMCID: PMC1429617.

18: Carter BL. Labetalol. Drug Intell Clin Pharm. 1983 Oct;17(10):704-12. Review. PubMed PMID: 6354658.

19: Vlachakis ND, Maronde RF, Maloy JW, Medakovic M, Kassem N. Pharmacodynamics of intravenous labetalol and follow-up therapy with oral labetalol. Clin Pharmacol Ther. 1985 Nov;38(5):503-8. PubMed PMID: 4053487.

20: Richards DA. Pharmacological effects of labetalol in man. Br J Clin Pharmacol. 1976 Aug;3(4 Suppl 3):721-3. Review. PubMed PMID: 10949.