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
- Molecular Weight:
- 328.41
- MOL File:
- 36894-69-6.mol
- MSDS File:
- SDS
- Modify Date:
- 2023/5/21 10:59:17
| 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) |
SAFETY
Risk and Safety Statements
| Symbol(GHS) |    GHS07,GHS08,GHS09 |
|---|---|
| Signal word | Warning |
| Hazard statements | H335-H411-H315-H361-H319 |
| Precautionary statements | P264-P280-P302+P352-P321-P332+P313-P362-P201-P202-P281-P308+P313-P405-P501-P264-P280-P305+P351+P338-P337+P313P |
Labetalol Chemical Properties,Uses,Production
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.
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.
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.
Labetalol Preparation Products And Raw materials
Raw materials
Preparation Products
| Supplier | Tel | Country | ProdList | Advantage | Inquiry |
|---|---|---|---|---|---|
| Cadila Pharmaceuticals Ltd | +91-7069076657 +91-7069076657 | Ahmedabad, India | 54 | 58 | Inquiry |
| J S LABS | +91-7330612784 +91-7330612784 | Tamil Nadu, India | 160 | 58 | Inquiry |
| Dayaram Pharma Chem | +91-9601766800 +91-9601766800 | Gujarat, India | 61 | 58 | Inquiry |
| VIVAN Life Sciences Pvt Ltd | +91-2225870080 +91-9987465183 | Maharashtra, India | 49 | 58 | Inquiry |
| PROTECH TELELINKS | +91-8571891912 +91-9855060837 | Himachal Pradesh, India | 62 | 58 | Inquiry |
| Niksan Pharmaceutical | +91-9537871777 +91-9537871777 | Gujarat, India | 39 | 58 | Inquiry |
| SynZeal Research Pvt Ltd | +1 226-802-2078 | Gujarat, India | 6522 | 58 | Inquiry |
| Pharmaffiliates Analytics and Synthetics P. Ltd | +91-172-5066494 | Haryana, India | 6773 | 58 | Inquiry |
| New Brothers Medical & Gen Store | 08068442223Ext 298 | Hyderabad, India | 5 | 58 | Inquiry |
| Dev Pharma | 08047644349 | Pune, India | 1 | 58 | Inquiry |
| Supplier | Advantage |
|---|---|
| Cadila Pharmaceuticals Ltd | 58 |
| J S LABS | 58 |
| Dayaram Pharma Chem | 58 |
| VIVAN Life Sciences Pvt Ltd | 58 |
| PROTECH TELELINKS | 58 |
| Niksan Pharmaceutical | 58 |
| SynZeal Research Pvt Ltd | 58 |
| Pharmaffiliates Analytics and Synthetics P. Ltd | 58 |
| New Brothers Medical & Gen Store | 58 |
| Dev Pharma | 58 |