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Substance Name: Propranolol [INN:BAN]
RN: 525-66-6
UNII: 9Y8NXQ24VQ
InChIKey: AQHHHDLHHXJYJD-UHFFFAOYSA-N

Note

  • A widely used non-cardioselective beta-adrenergic antagonist. Propranolol has been used for MYOCARDIAL INFARCTION; ARRHYTHMIA; ANGINA PECTORIS; HYPERTENSION; HYPERTHYROIDISM; MIGRAINE; PHEOCHROMOCYTOMA; and ANXIETY but adverse effects instigate replacement by newer drugs.

Molecular Formula

  • C16-H21-N-O2

Molecular Weight

  • 259.347
 

Classification Codes

  • Adrenergic Agents
  • Adrenergic Antagonists
  • Adrenergic beta-Antagonists
  • Anti-Arrhythmia Agents
  • Antihypertensive Agents
  • Cardiovascular Agents
  • Drug / Therapeutic Agent
  • Human Data
  • Mutation Data
  • Neurotransmitter Agents
  • Reproductive Effect
  • Vasodilator Agents

Names and Synonyms

Name of Substance

  • Propranolol
  • Propranolol [INN:BAN]

MeSH Heading

  • Propranolol

Synonyms

  • 1-((1-Methylethyl)amino)-3-(1-naphthalenyloxy)-2-propanol
  • 1-Isopropylamino-3-(1-naphthyloxy)-2-propanol
  • 2-Propanol, 1-((1-methylethyl)amino)-3-(1-naphthalenyloxy)-
  • 2-Propanol, 1-(isopropylamino)-3-(1-naphthyloxy)-
  • Anapriline
  • Avlocardyl
  • AY 20694
  • AY-20694
  • beta-Propranolol
  • Betadren
  • Betalong
  • CCRIS 3082
  • Corpendol
  • Dociton
  • EINECS 208-378-0
  • Euprovasin
  • Propanix
  • Propanolol
  • Propanolol [INN-Spanish]
  • Propranolol
  • Propranololo
  • Propranololo [DCIT]
  • Propranololum
  • Propranololum [INN-Latin]
  • Proprasylyt
  • Reducor
  • Sawatal
  • Sumial
  • UNII-9Y8NXQ24VQ

Systematic Names

  • 2-Propanol, 1-((1-methylethyl)amino)-3-(1-naphthalenyloxy)- (9CI)
  • 2-Propanol, 1-(isopropylamino)-3-(1-naphthyloxy)-
  • Propranolol

Registry Numbers

CAS Registry Number

  • 525-66-6

FDA UNII

  • 9Y8NXQ24VQ

System Generated Number

  • 0000525666

Structure Descriptors

InChI

1S/C16H21NO2/c1-12(2)17-10-14(18)11-19-16-9-5-7-13-6-3-4-8-15(13)16/h3-9,12,14,17-18H,10-11H2,1-2H3

InChIKey

AQHHHDLHHXJYJD-UHFFFAOYSA-N

Smiles

c12c(OC[C@@H](CNC(C)C)O)cccc1cccc2

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
child LDLo oral 800ug/kg/12H (0.8mg/kg) LUNGS, THORAX, OR RESPIRATION: ACUTE PULMONARY EDEMA

VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION

CARDIAC: PULSE RATE INCREASE WITHOUT FALL IN BP
British Medical Journal. Vol. 2, Pg. 254, 1978.
child TDLo oral 400mg/kg (400mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

CARDIAC: ARRHYTHMIAS (INCLUDING CHANGES IN CONDUCTION)
Medical Journal of Australia. Vol. 1, Pg. 82, 1981.
dog LDLo intraperitoneal 40mg/kg (40mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD Pharmazie. Vol. 31, Pg. 635, 1976.
dog LDLo oral 120mg/kg (120mg/kg) BEHAVIORAL: ATAXIA

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

SENSE ORGANS AND SPECIAL SENSES: MYDRIASIS (PUPILLARY DILATION): EYE
Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. Vol. 69(4), Pg. 262P, 1973.
guinea pig LD50 intravenous 26mg/kg (26mg/kg)   Dissertationes Pharmaceuticae et Pharmacologicae. Vol. 24, Pg. 103, 1972.
human LDLo intravenous 71ug/kg (0.071mg/kg)   Lancet. Vol. 1, Pg. 165, 1967.
human TDLo oral 2300ug/kg/D (2.3mg/kg) BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS" British Medical Journal. Vol. 1, Pg. 1182, 1978.
man TDLo oral 8343mg/kg/4Y- (8343mg/kg) ENDOCRINE: EVIDENCE OF THYROID HYPERFUNCTION Archives of Internal Medicine. Vol. 143, Pg. 2193, 1983.
man TDLo unreported 22857ug/kg/40 (22.857mg/kg) SENSE ORGANS AND SPECIAL SENSES: CHANGE IN ACUITY: EAR British Medical Journal. Vol. 289, Pg. 1490, 1984.
mouse LD50 intraperitoneal 42mg/kg (42mg/kg) AUTONOMIC NERVOUS SYSTEM: BETA ADRENERGIC BLOCKAGE Ain Shams Medical Journal. Vol. 30, Pg. 23, 1979.
mouse LD50 intravenous 24400ug/kg (24.4mg/kg)   United States Patent Document. Vol. #4013663,
mouse LD50 oral 289mg/kg (289mg/kg) AUTONOMIC NERVOUS SYSTEM: BETA ADRENERGIC BLOCKAGE Arzneimittel-Forschung. Drug Research. Vol. 30, Pg. 1831, 1980.
mouse LD50 subcutaneous 150mg/kg (150mg/kg)   Farmakologiya i Toksikologiya Vol. 44, Pg. 342, 1981.
rat LD50 intravenous 23mg/kg (23mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: ATAXIA
Pharmazie. Vol. 31, Pg. 635, 1976.
rat LD50 oral 660mg/kg (660mg/kg) BEHAVIORAL: ATAXIA

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Pharmazie. Vol. 31, Pg. 635, 1976.
women LDLo oral 120mg/kg (120mg/kg)   Acta Pharmacologica et Toxicologica. Vol. 41, Pg. 190, 1977.
women TDLo oral 3200ug/kg/2D- (3.2mg/kg) ENDOCRINE: HYPOGLYCEMIA Israel Journal of Medical Sciences. Vol. 18, Pg. 725, 1982.
women TDLo oral 708mg/kg/39W- (708mg/kg)   Annals of Pharmacotherpy. Vol. 27, Pg. 512, 1993.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 96 deg C   EXP
pKa Dissociation Constant 9.42 (none)   EXP
log P (octanol-water) 3.48 (none)   EXP
Water Solubility 61.7 mg/L 25 EXP
Vapor Pressure 3.82E-08 mm Hg 25 EST
Henry's Law Constant 7.98E-13 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 3.09E-10 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.