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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HCID 39147Generated: October 27, 2026

Nadolol

Nadolol (Mixture of Diastereomers) · 2,3-Naphthalenediol, 5-[3-[(1,1-dimethylethyl)amino]-2-hydroxypropoxy]-1,2,3,4-tetrahydro-, (2R,3S)-rel-

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Nadolol molecular structure

Identifiers & Physical Properties

CAS No.220045-89-6
Molecular formulaC17H27NO4
Average molar mass309.4 g/mol
SMILESCC(C)(C)NCC(O)COc1cccc2c1C[C@H](O)[C@H](O)C2
InChIKeyVWPOSFSPZNDTMJ-UCWKZMIHSA-N
PubChem CID39147
ChEMBLCHEMBL521606
EC No.255-706-3

Chemical & Physical Properties

XLogP0.7
Topological polar surface area82
Hydrogen bond donors4
Hydrogen bond acceptors5
Rotatable bonds6
Heavy atoms22
Formal charge0
Complexity344
Chemical classesPharmaceutical
LogP (partition coefficient)log Kow= 0.711.21.27
OdorOdorless
Color/FormWhite to off-white, crystalline powder
SolubilityFreely sol in propylene glycolslightly sol in chloroforminsol in acetone, benzene, ether, hexane.Practically insoluble in lipids.It is freely soluble in ethanol, soluble in hydrochloric acid, slightly soluble in water, and very slightly soluble in sodium hydroxide.2.25e+00 g/L>46.4 [ug/mL] (The mean of the results at pH 7.4)
Human DrugsBreast FeedingLactationMilk, HumanAntihypertensive AgentsAdrenergic Beta-AntagonistsAntiarrhythmicsFDA approved drugs -> Active ingredientPharmaceuticals
Melting point124-130124-136 °C124 - 136 °C
Physical DescriptionSolid
Dissociation Constants9.699.67pKa= 9.67
Collision Cross Section175.72 Ų [M+Na]+ [CCS Type: TWMethod: calibrated with polyalanine and drug standards]171.8 Ų [M+H]+ [CCS Type: TW172 Ų [M+H]+ [CCS Type: TWMethod: Major Mix IMS/Tof Calibration Kit (Waters)]
Boiling point526.4±50.0 °C(Predicted)
Density1.189±0.06 g/cm3(Predicted)
pKa (acidity coefficient)13.91±0.20(Predicted)
FDA UNIIFEN504330V

Safety & Regulations

GHS classificationThis chemical does not meet GHS hazard criteria for 33.3% (1 of 3) of reports.DangerH302 (33.3%): Harmful if swallowed [Warning Acute toxicity, oral]P260, P264, P270, P301+P317, P319, P330, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 3 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
FDA requirementsNadolol, used as a beta adrenergic blocking agent, was approved by FDA for marketing in the United States 12/79.The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed drug products, incl nadolol, approved on the basis of safety and effectiveness by FDA under sections 505 and 507 of the Federal Food, Drug, and Cosmetic Act.Manufacturers, packers, and distributors of drug and drug products for human use are responsible for complying with the labeling, certification, and usage requirements as prescribed by the Federal Food, Drug, and Cosmetic Act, as amended (secs 201-902, 52 Stat. 1040 et seq., as amended21 U.S.C. 321-392).
Hazard Classes and CategoriesSTOT RE 1 (33.3%)
Storage conditionsNadolol tablets should be stored in tight, light-resistant containers at room temperature.
Disposal methodsSRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air qualitypotential migration in soil or watereffects on animal, aquatic, and plant lifeand conformance with environmental and public health regulations.
Body burdenNadolol is distributed into milk /in humans/.
InteractionsThe beta-adrenergic stimulating effects of sympathomimetic agents are antagonized by nadolol. The interaction is especially pronounced with isoproterenol, and very large doses of isoproterenol may be needed to overcome the beta-adrenergic blocking effects of nadolol.
Antimuscarinic agents, such as atropine, may counteract the bradycardia caused by nadolol by reestablishing the balance between sympathetic and parasympathetic actions on the heart.
When nadolol is administered with diuretics or other hypotensive drugs, the hypotensive effect of nadolol may be increased.
High doses of nadolol may potentiate and prolong the effects of neuromuscular blocking agents such as tubocurarine chloride.
HepatotoxicityMild-to-moderate elevations in serum aminotransferase levels occur in less than 1% of patients on nadolol and are usually transient and asymptomatic, resolving even with continuation of therapy. Despite its widespread use, nadolol has not been convincingly linked to instances of clinically apparent liver injurythe few cases reported have generally occurred in patients who were receiving other well known hepatotoxic agents or were associated with serum enzyme elevations only. Other beta-blockers have been implicated in causing rare instances of acute liver injury, with latency to onset ranging from 4 to 24 weeks, a hepatocellular pattern of serum enzyme elevations, and a mild, self-limiting course without evidence of hypersensitivity or autoimmune reactions.
Environmental fateTERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 60(SRC), determined from a log Kow of 0.71(2) and a regression-derived equation(3), indicates that nadolol is expected to have high mobility in soil(SRC). Volatilization of nadolol from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.4X10-14 atm-cu m/mole(SRC), using a fragment constant estimation method(4). Nadolol is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 9.9X10-11 mm Hg(SRC), determined from a fragment constant method(5).AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 60(SRC), determined from a log Kow of 0.71(2) and a regression-derived equation(3), indicates that nadolol is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 1.4X10-14 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), an estimated BCF of 3(SRC), from its log Kow(2) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is low(SRC).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), nadolol, which has an estimated vapor pressure of 9.9X10-11 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase nadolol may be removed from the air by wet and dry deposition(SRC).
Adverse effectsNadolol has been well-tolerated in most clinical studies with minimal adverse effects. The adverse effects of nadolol are mainly because of its impact on the β-2 receptors. No known reports of major organ injury are from using nadolol. However, there is evidence of a mild-to-moderate increase in liver enzymes in certain patient populations, particularly aspartate aminotransferase (AST) and alanine aminotransferase (ALT), due to the first-pass metabolism of nadolol in the liver. Typically, these patients are asymptomatic, and liver functions return to baseline with continued therapy. No evidence of nadolol causing clinically apparent liver injury exists, but this adverse effect can get aggravated when used in combination with other hepatotoxic drugs. Nadolol is safe for use in patients with cirrhosis for primary or secondary prophylaxis of varices without affecting liver function.
Milk ConcentrationsNadolol is distributed into milk /in humans/.
Toxicity summaryMost nadolol poisonings occur via the intentional consumption of the tablet. No reports of significant toxicity are apparent in the literature. Most cases of nadolol poisoning are mild. These patients can be observed in an emergency department for 4 hours and discharged if no signs of poisoning develop. If moderate-to-severe toxicity persists, early decontamination with activated charcoal can be used along with gastric lavage if significant ingestion is suspected. After stabilizing the patient for airway, breathing, and circulation, enhanced elimination with hemodialysis is possible, considering nadolol's low distribution volume and longer half-life.
Effluent ConcentrationsNadolol was detected at concentrations of <0.025 to 0.29 ug/l in German sewage effluents(1).
Soil Adsorption/MobilityThe Koc of nadolol is estimated as 60(SRC), using a log Kow of 0.71(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that nadolol is expected to have high mobility in soil.
Human Toxicity Excerpts/HUMAN EXPOSURE STUDIES/ The effects of short-term nadolol administration on the reactive oxygen species (ROS) generation by polymorphonuclear leukocytes and mononuclear cells /was studied/ in 8 normal subjects. At a oral dose of 40 mg/day for 5 days, nadolol produced a decrease in the ROS generation by leukocytes. ROS generation by polymorphonuclear leukocytes decreased by 38% from 134 +/- 44 mV at baseline to 83 +/- 34 mV after 5 days (p = 0.005), and ROS generation by mononuclear cells decreased by 33% from 174 +/- 69 mV at baseline to 117 +/- 55 mV after 5 days (p = 0.015). A significant reduction in linoleic acid oxidation was reflected by the lower levels of 9- and 13- hydroxy-octadecadienoic acid after 5 days. There was no change in the plasma thiobarbituric acid-reacting substances, a less sensitive index of oxidative damage to lipids. There was also no significant change in the levels of metatyrosine and orthotyrosine, which are known indexes of oxidative damage to amino acids and proteins. The absence of a significant change in metatyrosine, orthotyrosine, and thiobarbituric acid-reacting substances may reflect the short duration of nadolol administration and the decreased ROS load.
Artificial Pollution SourcesNadolol's production and use as a pharmaceutical drug(1) may result in its release to the environment through various waste streams(SRC).
Drug Induced Liver InjuryDrug Induced Liver Injury Rank (DILIrank 2.0)NadololAmbiguous-DILI-concern3Adverse reactionsDOI:10.1016/j.drudis.2016.02.015