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2-hydroxy-5-{1-hydroxy-2-[(4-phenylbutan-2-yl)amino]ethyl}benzamide
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ChemBase ID:
480
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Molecular Formular:
C19H24N2O3
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Molecular Mass:
328.40546
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Monoisotopic Mass:
328.17869264
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SMILES and InChIs
SMILES:
OC(CNC(CCc1ccccc1)C)c1cc(c(O)cc1)C(=O)N
Canonical SMILES:
CC(CCc1ccccc1)NCC(c1ccc(c(c1)C(=O)N)O)O
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)
InChIKey:
SGUAFYQXFOLMHL-UHFFFAOYSA-N
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Cite this record
CBID:480 http://www.chembase.cn/molecule-480.html
NAMES AND DATABASE IDS
NAMES AND DATABASE IDS
Names Database IDs
IUPAC name
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2-hydroxy-5-{1-hydroxy-2-[(4-phenylbutan-2-yl)amino]ethyl}benzamide
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IUPAC Traditional name
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Brand Name
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Albetol
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Ibidomide
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Normodyne
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Presdate
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Trandate
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Synonyms
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Labetolol
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Labetalolum [INN-Latin]
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Labetalol hydrochloride
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Labetalol HCL
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Labetalol
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CAS Number
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PubChem SID
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PubChem CID
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DATA SOURCES
DATA SOURCES
All Sources Commercial Sources Non-commercial Sources
Data Source
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Data ID
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Price
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CALCULATED PROPERTIES
CALCULATED PROPERTIES
JChem
ALOGPS 2.1
Acid pKa
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8.049597
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H Acceptors
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4
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H Donor
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4
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LogD (pH = 5.5)
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-0.09246248
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LogD (pH = 7.4)
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1.2584062
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Log P
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1.8865051
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Molar Refractivity
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94.7152 cm3
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Polarizability
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36.471325 Å3
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Polar Surface Area
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95.58 Å2
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Rotatable Bonds
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8
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Lipinski's Rule of Five
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true
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Log P
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1.73
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LOG S
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-4.75
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Solubility (Water)
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5.78e-03 g/l
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PROPERTIES
PROPERTIES
Physical Property
Bioassay(PubChem)
Solubility
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20 mg/ml (HCl salt)
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Show
data source
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Hydrophobicity(logP)
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2.7
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Show
data source
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DETAILS
DETAILS
DrugBank
DrugBank -
DB00598
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Item |
Information |
Drug Groups
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approved |
Description
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Blocker of both alpha- and beta-adrenergic receptors that is used as an antihypertensive. [PubChem] |
Indication |
For the management of hypertension (alone or in combination with other classes of antihypertensive agents), as well as chronic stable angina pectoris and sympathetic overactivity syndrome associated with severe tetanus. Labetalol is used parenterally for immediate reduction in blood pressure in severe hypertension or in hypertensive crises when considered an emergency, for the control of blood pressure in patients with pheochromocytoma and pregnant women with preeclampsia, and to produce controlled hypotension during anesthesia to reduce bleeding resulting from surgical procedures. |
Pharmacology |
Labetalol is an selective alpha-1 and non-selective beta adrenergic blocker used to treat high blood pressure. It works by blocking these adrenergic receptors, which slows sinus heart rate, decreases peripheral vascular resistance, and decreases cardiac output. Labetalol has two asymmetric centers and therefore, exists as a molecular complex of two diastereoisomeric pairs. Dilevalol, the R,R' stereoisomer, makes up 25% of racemic labetalol. |
Toxicity |
LD50 = 66 mg/kg (Rat, IV). Side effects or adverse reactions include dizziness when standing up, very low blood pressure, severely slow heartbeat, weakness, diminished sexual function, fatigue |
Affected Organisms |
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Humans and other mammals |
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Biotransformation |
Primarily hepatic, undergoes significant first pass metabolism |
Absorption |
Completely absorbed (100%) from the gastrointestinal tract with peak plasma levels occurring 1 to 2 hours after oral administration. The absolute bioavailability of labetalol is increased when administered with food. |
Half Life |
6-8 hours |
Protein Binding |
50% |
Elimination |
These metabolites are present in plasma and are excreted in the urine, and via the bile, into the feces. |
External Links |
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PATENTS
PATENTS
PubChem Patent
Google Patent