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Labetalol

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Product Name
Labetalol
CAS No.
36894-69-6
Chemical Name
Labetalol
Synonyms
Laβlol;ah5158;albetol;LABEIM-B;LABETOLOL;LABETALOL;ibidomide;SeH-15719W;Labeint-A8;Labetalol (AH-5158
CBNumber
CB7735086
Molecular Formula
C19H24N2O3
Formula Weight
328.41
MOL File
36894-69-6.mol
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Labetalol Property

Melting point:
188 °C
Boiling point:
552.7±50.0 °C(Predicted)
Density 
1.200±0.06 g/cm3(Predicted)
storage temp. 
Store at -20°C
solubility 
DMSO : 125 mg/mL (380.62 mM; Need ultrasonic)
pka
pKa 7.41 ± 0.01;9.36± 0.01(H2O,t =25,I=0.15(KCl),Ar)(Approximate)
form 
Solid
color 
White to Pale Orange
Stability:
Hygroscopic
CAS DataBase Reference
36894-69-6(CAS DataBase Reference)
NIST Chemistry Reference
Benzamide, 2-hydroxy-5-[1-hydroxy-2-[(1-methyl-3-phenylpropyl)amino]ethyl]-(36894-69-6)
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Safety

Hazardous Substances Data
36894-69-6(Hazardous Substances Data)
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

H361Suspected of damaging fertility or the unborn child

H411Toxic to aquatic life with long lasting effects

Precautionary statements

P201Obtain special instructions before use.

P202Do not handle until all safety precautions have been read and understood.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P281Use personal protective equipment as required.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P308+P313IF exposed or concerned: Get medical advice/attention.

P321Specific treatment (see … on this label).

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P362Take off contaminated clothing and wash before reuse.

P405Store locked up.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

AK Scientific
Product number
U685
Product name
Labetalol
Packaging
250mg
Price
$224
Updated
2021/12/16
American Custom Chemicals Corporation
Product number
API0026318
Product name
5-[1-HYDROXY-2-[(1-METHYL-3-PHENYLPROPYLAMINO)ETHYL]SALICYLAMIDE
Purity
95.00%
Packaging
1G
Price
$780.15
Updated
2021/12/16
American Custom Chemicals Corporation
Product number
API0026318
Product name
5-[1-HYDROXY-2-[(1-METHYL-3-PHENYLPROPYLAMINO)ETHYL]SALICYLAMIDE
Purity
95.00%
Packaging
100G
Price
$2971.24
Updated
2021/12/16
Crysdot
Product number
CD12078046
Product name
2-Hydroxy-5-(1-hydroxy-2-((4-phenylbutan-2-yl)amino)ethyl)benzamide
Purity
98%
Packaging
1g
Price
$325
Updated
2021/12/16
AHH
Product number
API-1558
Product name
Labetalol
Purity
98%
Packaging
1g
Price
$700
Updated
2021/12/16
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Labetalol Chemical Properties,Usage,Production

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Labetalol is a competitive α1- and β-antagonist which is more active at β- than at α-receptors (1 : 3–1 : 7, depending on route). It may be administered orally or i.v. Intravenous bolus doses range from 50–200mg, with infusion rates between 5–150mgh –1, titrated to effect.

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.

Originator

Trandate,Allen and Hanburys,UK,1977

Uses

Labetalol is used to treat essential hypertension.

Uses

Anti-adrenergic (α-receptor); anti-adrenergic (β-receptor).

Definition

ChEBI: A secondary amino compound formally derived from ammonia by replacing two of the hydrogens by 2-(3-carbamoyl-4-hydroxyphenyl)-2-hydroxyethyl and 4-phenylbutan-2-yl groups. It is an adrenergic antagonist used to treat high blood pressure.

Manufacturing Process

(a) 5-Bromoacetylsalicylamide (2.6 g), N-benzyl-N-(1-methyl-3-phenylpropyl) amine (4.8 g) and methyl ethyl ketone (50 ml) were heated at reflux for 40 minutes. The solvent was removed and the residue was treated with benzene. The secondary amine hydrobromide was filtered off and discarded, and the filtrate was evaporated to dryness. The residue was treated with an excess of ethanolic hydrogen chloride when 5-[N-benzyl-N-(1-methyl-3-phenylpropyl)- glycyl]-salicylamide hydrochloride (1.15 g) crystallized out, MP 139°C to 141°C.
(b) 5-[N-benzyl-N-(1-methyl-3-phenylpropyl)glycyl]-salicylamide hydrochloride (0.75 g), 10% mixture of PdO and PtO on carbon catalyst (0.1 g) and ethanol (20 ml) were shaken at room temperature and pressure with hydrogen until uptake ceased. The catalyst was filtered off and the filtrate evaporated to dryness. The residue was crystallized from ethanol to give 5-[1- hydroxy-2-(1-methyl-3-phenylpropyl)aminoethyl]salicylamide hydrochloride as a white solid (0.40 g), MP 188°C.

brand name

Normodyne (Schering); Trandate (Promethus).

Therapeutic Function

Alpha-adrenergic blocker, Beta-adrenergic blocker

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.

General Description

Labetalol is a phenylethanolamine derivative, is representative of a classof drugs that act as competitive blockers at α1-, β1-, andβ2-receptors. It is a more potent β-blocker than α-blocker.Because it has two asymmetric carbon atoms (1 and 1' ), it existsas a mixture of four isomers. It is this mixture that is usedclinically in treating hypertension. The different isomers,however, possess different α- and β-blocking activities. The -blocking activity resides solely in the (1R,1 'R) isomer,whereas the 1-blocking activity is seen in the (1S,1 R) and(1S,1'S) isomers, with the (1S,1'R) isomer possessing thegreater therapeutic activity.

Contact allergens

This beta-adrenergic and alpha-1 blocking agent caused contact dermatitis and a contact anaphylactoid reaction during patch testing in a nurse.

Mechanism of action

Labetalol produces equilibrium-competitive antagonism at β-receptors but does not exhibit selectivity for β1- or β2-receptors. Like certain other β-blockers (e.g., pindolol and timolol), labetalol possesses some degree of intrinsic activity. This intrinsic activity, or partial agonism, especially at β2-receptors in the vasculature, has been suggested to contribute to the vasodilator effect of the drug. The membrane-stabilizing effect, or local anesthetic action, of propranolol and several other β-blockers, is also possessed by labetalol, and in fact the drug is a reasonably potent local anesthetic.
Labetalol appears to produce relaxation of vascular smooth muscle not only by α-blockade but also by a partial agonist effect at β2-receptors. In addition, labetalol may produce vascular relaxation by a direct non–receptor-mediated effect. Labetalol can block the neuronal uptake of norepinephrine and other catecholamines. This action, plus its slight intrinsic activity at α-receptors, may account for the seemingly paradoxical, although infrequent, increase in blood pressure seen on its initial administration.

Pharmacokinetics

Labetalol is almost completely absorbed from the gastrointestinal tract. However, it is subject to considerable first-pass metabolism, which occurs in both the gastrointestinal tract and the liver, so that only about 25% of an administered dose reaches the systemic circulation. While traces of unchanged labetalol are recovered in the urine, most of the drug is metabolized to inactive glucuronide conjugates.The plasma half-life of labetalol is 6 to 8 hours, and the elimination kinetics are essentially unchanged in patients with impaired renal failure.

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.

Side effects

There have been reports of excessive hypotension and paradoxical pressor effects following intravenous administration of labetalol. These latter effects may be due to a labetalol-induced blockade of neuronal amine uptake, which increases the concentrations of norepinephrine in the vicinity of its receptors.
Approximately 5% of the patients who receive labetalol complain of side effects typical of noradrenergic nervous system suppression. These include postural hypotension, gastrointestinal distress, tiredness, sexual dysfunction, and tingling of the scalp. Most of these effects are related to α-blockade, although the tingling of the scalp may be due to the drug’s intrinsic activity at α-receptors. Side effects associated with β-blockade, such as induction of bronchospasm and congestive heart failure, may also occur, but generally at a lower frequency than -receptor–associated effects.
Skin rashes have been reported, as has an increase in the titer of antinuclear antibodies. Despite the latter observation, the appearance of a systemic lupus syndrome is rare. Labetalol also has been reported to interfere with chemical measurements of catecholamines and metabolites.

Synthesis

Labetalol, 2-hydroxy-5-[1-hydroxy-2-[(1-methyl-3-phenylpropanol)amino)] ethyl] benzamide (12.1.12) is synthesized by the N-alkylation of N-benzyl-N(4-phenyl-2- butyl)amine 5-bromacetylsalicylamide and forming aminoketone (12.1.11), which is further debenzylated by hydrogen using a palladium¨Cplatinum on carbon catalyst into labetalol (12.1.12) [28¨C30].

Labetalol Preparation Products And Raw materials

Raw materials

Preparation Products

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Labetalol Suppliers

LGM Pharma
Tel
1-(800)-881-8210
Fax
615-250-9817
Email
inquiries@lgmpharma.com
Country
United States
ProdList
2127
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70
XiaoGan ShenYuan ChemPharm co,ltd
Tel
0712-0712-2580635 15527768850
Email
1791901229@qq.com
Country
China
ProdList
8850
Advantage
52
Beijing HuaMeiHuLiBiological Chemical
Tel
010-56205725
Fax
010-65763397
Email
waley188@sohu.com
Country
China
ProdList
12338
Advantage
58
Nanjing Sunlida Biological Technology Co., Ltd.
Tel
025-57798810
Fax
025-57019371
Email
sales@sunlidabio.com
Country
China
ProdList
3750
Advantage
55
TargetMol Chemicals Inc.
Tel
021-33632979 15002134094
Fax
021-33632979
Email
marketing@targetmol.com
Country
China
ProdList
7934
Advantage
58
HangZhou YuHao Chemical Technology Co., Ltd.
Tel
0571-82693216
Fax
0571-82880190
Email
info@yuhaochemical.com
Country
China
ProdList
3519
Advantage
58
Shanghai Xingui Biotechnology Co., Ltd.
Tel
17501653713 17501653715
Email
xingui2022@126.com
Country
China
ProdList
10043
Advantage
58
Shanghai HuanChuan Industry Co.,Ltd.
Tel
021-61478794
Fax
021-61478794
Email
sales@hcshhai.com
Country
China
ProdList
9798
Advantage
50
Credit Asia Chemical Co., Ltd.
Tel
+86 (21) 61124340
Fax
+86 (21) 6129-4103
Country
China
ProdList
9767
Advantage
58
Chizhou Kailong Import and Export Trade Co., Ltd.
Tel
Fax
-
Email
xg01_gj@163.com
Country
China
ProdList
9503
Advantage
50
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View Lastest Price from Labetalol manufacturers

Zhuozhou Wenxi import and Export Co., Ltd
Product
Labetalol 36894-69-6
Price
US $15.00-10.00/KG
Min. Order
1KG
Purity
99%+ HPLC
Supply Ability
Monthly supply of 1 ton
Release date
2021-07-11
Zhuozhou Wenxi import and Export Co., Ltd
Product
Labetalol 36894-69-6
Price
US $15.00-10.00/KG
Min. Order
1KG
Purity
99%+ HPLC
Supply Ability
Monthly supply of 1 ton
Release date
2021-07-09

36894-69-6, LabetalolRelated Search:


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  • LABETALOL
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  • Labetalol (base and/or unspecified salts)
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  • 2-Hydroxy-5-(1-hydroxy-2-((4-phenylbutan-2-yl)
  • 2-hydroxy-5-(1-hydroxy-2-((1-methyl-3-phenylpropyl)amino)ethyl)-benzamid
  • 2-hydroxy-5-(1-hydroxy-2-((1-methyl-3-phenylpropyl)amino)ethyl)benzamide
  • LABEIM-B
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  • ah5158
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  • 1H-Benzimidazole-1-carboxylicacid,2,3-dihydro-4-oxo-,ethylester
  • 36894-69-6
  • C19H24N2O3
  • API's