Promethazine

Promethazine
Clinical data
Trade namesPhenergan, others
AHFS/Drugs.comMonograph
MedlinePlusa682284
License data
Pregnancy
category
  • AU: C
Routes of
administration
By mouth, rectal, intravenous, intramuscular, topical
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability88% absorbed but after first-pass metabolism reduced to 25% absolute bioavailability
Protein binding93%
MetabolismLiver glucuronidation and sulfoxidation
Elimination half-life10–19 hours
ExcretionKidney and Bile duct
Identifiers
  • (RS)-N,N-Dimethyl-1-(10H-phenothiazin-10-yl)propan-2-amine
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.000.445
Chemical and physical data
FormulaC17H20N2S
Molar mass284.42 g·mol−1
3D model (JSmol)
ChiralityRacemic mixture
  • S2c1ccccc1N(c3c2cccc3)CC(N(C)C)C
  • InChI=1S/C17H20N2S/c1-13(18(2)3)12-19-14-8-4-6-10-16(14)20-17-11-7-5-9-15(17)19/h4-11,13H,12H2,1-3H3 Y
  • Key:PWWVAXIEGOYWEE-UHFFFAOYSA-N Y
  (verify)

Promethazine, sold under the brand name Phenergan among others, is a first-generation antihistamine, sedative, and antiemetic used to treat allergies, insomnia, and nausea. It may also help with some symptoms associated with the common cold and may also be used for sedating people who are agitated or anxious, an effect that has led to some recreational use (especially with codeine). Promethazine is taken by mouth (oral), as a rectal suppository, or by injection into a muscle (IM).

Common side effects of promethazine include confusion and sleepiness; consumption of alcohol or other sedatives can make these symptoms worse. It is unclear if use of promethazine during pregnancy or breastfeeding is safe for the fetus. Use of promethazine is not recommended in those less than two years old, due to potentially negative effects on breathing. Use of promethazine by injection into a vein is not recommended, due to potential skin damage. Promethazine is in the phenothiazine family of medications. It is also a strong anticholinergic, which produces its sedative effects. This also means high or toxic doses can act as a deliriant.

Promethazine was made in the 1940s by a team of scientists from Rhône-Poulenc laboratories. It was approved for medical use in the United States in 1951. It is a generic medication and is available under many brand names globally. In 2022, it was the 198th most commonly prescribed medication in the United States, with more than 2 million prescriptions. In 2022, the combination with dextromethorphan was the 260th most commonly prescribed medication in the United States, with more than 1 million prescriptions.