Substance

ID:280

Phenylpropanolamine

Names and Identifiers
IUPAC name
(1S,2R)-2-amino-1-phenylpropan-1-ol
IUPAC Traditional name
phenylpropanolamine
Brand Name
Ami-TexDexatrimMyminicSnapletsRhymedULRVanexDespecEntexPhenylfenesinPropagestRhindeconCodimalContussGentabNolexPhenyldrineTriaminicGuaipaxNaldeconPartussPhenoxineAcutrimConexDura-Vent
Synonyms
(+/-)-Norephedrin(+-)-PhenylpropanolaminePPAPhenylpropanolamine
Registration numbers
PubChem CID
CAS Number
PubChem SID
Properties
Physical Property
Solubility
Freely soluble
Hydrophobicity(logP)
1
Molecule Details
Drug Groups
approved; withdrawn
Description
Phenylpropanolamine has been withdrawn in Canada. In November 2000, the Food and Drug Administration (FDA) issued a public health advisory against the use of the drug.
Indication
For the treatment of nasal congestion, control of urinary incontinence, priapism and obesity.
Pharmacology
Phenylpropanolamine (PPA), a sympathomimetic agent structurally similar to pseudoephedrine, is used to treat nasal congestion. Phenylpropanolamine is found in appetite suppressant formulations and with guaifenesinin in cough-cold formulations. In 2000, the FDA requested that all drug companies discontinue marketing products containing phenylpropanolamine, due to an increased risk of hemorrhagic stroke in women who used phenylpropanolamine.
Toxicity
May induce ventricular extrasystoles and short paroxysms of ventricular tachycardia, a sensation of fullness in the head and tingling of the extremities; LD50=1490mg/kg (orally in rat)
Affected Organisms
Humans and other mammals
Biotransformation
Hepatic
Absorption
Reduced bioavailability (about 38%) from gastrointestinal tract because of first pass metabolism by monoamine oxidase in the stomach and liver.
Half Life
2.1 to 3.4 hours.
External Links
Molecular Spectra
No Data Available
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References
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