Labetalol

Base Information

• Chemical Name: Labetalol
• CAS No.: 36894-69-6
• Molecular Formula: C₁₉H₂₄N₂O₃
• Molecular Weight: 328.411
• Hs Code.: 2924299090
• European Community (EC) Number: 253-258-3
• UNII: R5H8897N95
• DSSTox Substance ID: DTXSID2023191
• Nikkaji Number: J19.703C
• Wikipedia: Labetalol
• Wikidata: Q958087
• NCI Thesaurus Code: C29146
• RXCUI: 6185
• Pharos Ligand ID: 3ZGPVBF8GZQ6
• Metabolomics Workbench ID: 42928
• ChEMBL ID: CHEMBL429
• Mol file: 36894-69-6.mol

Synonyms:AH 5158;AH-5158;AH5158;Albetol;Apo Labetalol;Apo-Labetalol;ApoLabetalol;Dilevalol;Hydrochloride, Labetalol;Labetalol;Labetalol Hydrochloride;Labetalol, (R,R)-Isomer;Labetolol;Normodyne;Presolol;R,R Labetalol;R,R-Labetalol;SCH 19927;SCH-19927;SCH19927;Trandate

Chemical Property of Labetalol

Chemical Property:

• Melting Point: 188 °C
• Boiling Point: 552.686 °C at 760 mmHg
• PKA: pKa 7.41 ± 0.01；9.36± 0.01(H2O,t =25,I=0.15(KCl)，Ar)(Approximate)
• Flash Point: 288.054 °C
• PSA: 95.58000
• Density: 1.201 g/cm³
• LogP: 3.22660
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 8
• Exact Mass: 328.17869263
• Heavy Atom Count: 24
• Complexity: 385

Purity/Quality:

99.9% ^*data from raw suppliers

2-Hydroxy-5-(1-hydroxy-2-((4-phenylbutan-2-yl)amino)ethyl)benzamide 98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Beta-Adrenergic Receptor Antagonists
• Canonical SMILES: CC(CCC1=CC=CC=C1)NCC(C2=CC(=C(C=C2)O)C(=O)N)O
• Recent ClinicalTrials: Postpartum Hypertension Study
• Recent EU Clinical Trials: Pregnancy ANtihypertensive Drugs: which Agent is best?
• Description: Labetalol is an α-adrenergic and α-1 blocking agent which caused contact dermatitis and a contact anaphylactoid reaction during patch testing in a nurse.
• Uses: Labetalol is used to treat essential hypertension. Anti-adrenergic (α-receptor); anti-adrenergic (β-receptor).
• Biological Functions: Labetalol (Normodyne, Trandate) possesses both - blocking and β-blocking activity and is approximately one-third as potent as propranolol as a -blocker and one-tenth as potent as phentolamine as an -blocker. The ratio of β- to α-activity is about 3:1 when labetalol is administered orally and about 7: 1 when it is administered intravenously. Thus the drug can be most conveniently thought of as a β -blocker with some -blocking properties.
• Clinical Use: Labetalol is a clinically usefulantihypertensive agent. The rationale for its use in themanagement of hypertension is that its α-receptor–blockingeffects produce vasodilation and its β-receptor–blockingeffects prevent the reflex tachycardia usually associated withvasodilation. Although labetalol is very well absorbed, it undergoesextensive first-pass metabolism.

Technology Process of Labetalol

There total 7 articles about Labetalol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

→ labetaol (36894-69-6,61466-67-9,61466-91-9,72487-31-1,72487-32-2,75659-07-3,83167-24-2,83167-31-1,83167-32-2)

Guidance literature:

Gemisch A/B, 1) p-Toluolsulfonsaeure, 2) Hydrolyse;

Reference yield:

→ 5-[1-Hydroxy-2-(1-methyl-3-phenylpropyl)aminoethyl]salicyamide + labetaol (36894-69-6,61466-67-9,61466-91-9,72487-31-1,72487-32-2,75659-07-3,83167-24-2,83167-31-1,83167-32-2)

Guidance literature:

Reference yield:

1-phenyl-3-butanol (2344-70-9) → labetaol (36894-69-6,61466-67-9,61466-91-9,72487-31-1,72487-32-2,75659-07-3,83167-24-2,83167-31-1,83167-32-2)

Guidance literature:

Multi-step reaction with 3 steps

1: triethylamine / dichloromethane / -10 - 20 °C

2: potassium carbonate / acetonitrile / 81 °C

3: palladium 10% on activated carbon; hydrogen / methanol / 8 h / 50 °C / 3750.38 Torr

With palladium 10% on activated carbon; hydrogen; potassium carbonate; triethylamine; In methanol; dichloromethane; acetonitrile;

upstream raw materials:

1-phenyl-3-butanol

5-(2-bromoacetyl)-2-hydroxybenzamide

2-hydroxy-5-<acetyl>benzamide

labetaol

Downstream raw materials:

2-Hydroxy-5-[1-hydroxy-2-((R)-1-methyl-3-phenyl-propylamino)-ethyl]-benzamide

2-Hydroxy-5-[1-hydroxy-2-((S)-1-methyl-3-phenyl-propylamino)-ethyl]-benzamide

*)>-2-hydroxy-5-<1-hydroxy-2-<(1-methyl-3-phenylpropyl)amino>ethyl>benzamide

*)>-2-hydroxy-5-<1-hydroxy-2-<(1-methyl-3-phenylpropyl)amino>ethyl>benzamide

Refernces

• 1、 Shuang, Yazhou,Liao, Yuqin,Wang, Hui,Wang, Yuanxing,Li, Laisheng. "Preparation and evaluation of a triazole-bridged bis(β-cyclodextrin)–bonded chiral stationary phase for HPLC". . p. 168 - 184. Retrieved 2019/11/25.
• 2、 -. "THERAPY FOR COMPLICATIONS OF DIABETES". . . Retrieved 2009/07/02.