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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
- All
- Classifications
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- Names & Synonyms
- Registry Numbers
- Structure Descriptors
- Toxicity
- Physical Properties
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
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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
Other Registry Number
- 13013-17-7
System Generated Number
- 0000525666
Structure Descriptors
InChI
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,10-11H2,1-2H3InChIKey
AQHHHDLHHXJYJD-UHFFFAOYSA-NSmiles
CC(C)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.