Promethazine

Promethazine
Clinical data
Trade names	Phenergan, many others
AHFS/Drugs.com	Monograph
MedlinePlus	a682284
License data	US DailyMed: Promethazine;
Pregnancy; category	AU: C;
Routes of; administration	By mouth, rectal, intravenous, intramuscular, topical
ATC code	D04AA10 (WHO) R06AD02 (WHO);
Legal status
Legal status	AU: S3 (Pharmacist only); CA: OTC; UK: P (Pharmacy medicines) (POM when injection); US: ℞-only; South Africa: S5 IV, S2 oral;
Pharmacokinetic data
Bioavailability	88% absorbed but after first-pass metabolism reduced to 25% absolute bioavailability
Protein binding	93%
Metabolism	Liver glucuronidation and sulfoxidation
Elimination half-life	10–19 hours
Excretion	Kidney and biliary
Identifiers
	IUPAC name (RS)-N,N-Dimethyl-1-(10H-phenothiazin-10-yl)propan-2-amine;
CAS Number	60-87-7 ; 58-33-3 (HCl);
PubChem CID	4927;
IUPHAR/BPS	7282;
DrugBank	DB01069 ;
ChemSpider	4758 ;
UNII	FF28EJQ494;
KEGG	D00494 ;
ChEBI	CHEBI:8461 ;
ChEMBL	ChEMBL643 ;
CompTox Dashboard (EPA)	DTXSID7023518 ;
ECHA InfoCard	100.000.445
Chemical and physical data
Formula	C17H20N2S
Molar mass	284.42 g·mol−1
3D model (JSmol)	Interactive image;
Chirality	Racemic mixture
	SMILES S2c1ccccc1N(c3c2cccc3)CC(N(C)C)C;
	InChI 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 ; Key:PWWVAXIEGOYWEE-UHFFFAOYSA-N ;
	(verify)

Promethazine, sold under the brand name Phenergan among others, is a first-generation antihistamine, antipsychotic, 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 moderate anticholinergic, which produces its sedative effects. This also means high doses 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 2020, it was the 208th most commonly prescribed medication in the United States, with more than 2 million prescriptions.

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