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Promethazine

Catalog No. DB01069 Name DrugBank
CAS Number 60-87-7 Website http://www.ualberta.ca/
M. F. C17H20N2S Telephone (780) 492-3111
M. W. 284.4191 Fax (780) 492-1071
Purity Email david.wishart@ualberta.ca
Storage Chembase ID: 940

SYNONYMS

IUPAC name
dimethyl[1-(10H-phenothiazin-10-yl)propan-2-yl]amine
IUPAC Traditional name
promethazine
Brand Name
Phenergan Fortis
Remsed
Avomine
Phargan
Promethaine
Promethegan
Duplamin
Fenergan
Histargan
Isophenergan
Phencen
Prometazin
Promethacon
Provigan
Tanidil
Allergan
Diphergan
Dorme
Fellozine
Fenetazina
Genphen
Lergigan
Phenargan
Phensedyl
Pipolphen
Prometasin
Prometh Plain
Prorex
Pyrethia
Pyrethiazine
Thiergan
Valergine
Zipan-25
Aprobit
Dimapp
Diprazine
Diprozin
Fargan
Fenazil
Hiberna
Iergigan
Lercigan
Mymethazine Fortis
Phenergan
Pilpophen
Procit
Prometh Fortis
Protazine
Romergan
Synalgos
Vallergine
Synonyms
Promethazine Hcl
Promethiazine
Prothazin
Lilly 1516
Isopromethazine
Proazaimine
Promezathine
Prothazine
Proazamine
Promazinamide
Promethazin
Prometazine

DATABASE IDS

PubChem CID 4927
PubChem SID 46507798
CAS Number 60-87-7

PROPERTIES

Hydrophobicity(logP) 4.4
Solubility Freely soluble

DETAILS

Description (English)
Item Information
Drug Groups approved
Description A phenothiazine derivative with histamine H1-blocking, antimuscarinic, and sedative properties. It is used as an antiallergic, in pruritus, for motion sickness and sedation, and also in animals. [PubChem]
Indication For the treatment of allergic disorders, and nausea/vomiting.
Pharmacology Promethazine, a phenothiazine, is an H1-antagonist with anticholinergic, sedative, and antiemetic effects and some local anesthetic properties. Promethazine is used as an antiemetic or to prevent motion sickness.
Toxicity Symptoms of overdose include mild depression of the central nervous system and cardiovascular system to profound hypotension, respiratory depression, unconsciousness, and sudden death. Other reported reactions include hyperreflexia, hypertonia, ataxia, athetosis, and extensor-plantar reflexes (Babinski reflex). LD50=55mg/kg (I.V. in mice)
Affected Organisms
Humans and other mammals
Biotransformation Hepatic
Absorption On average, 88% of a promethazine dose is absorbed after oral administration; however, the absolute bioavailability is only 25% because of first-pass clearance.
Half Life 16-19 hours
Protein Binding 93%
Elimination Promethazine hydrochloride is metabolized in the liver, with the sulfoxides of promethazine and N-desmethylpromethazine being the predominant metabolites appearing in the urine.
References
Peters RJ Jr, Kelder SH, Markham CM, Yacoubian GS Jr, Peters LA, Ellis A: Beliefs and social norms about codeine and promethazine hydrochloride cough syrup (CPHCS) onset and perceived addiction among urban Houstonian adolescents: an addiction trend in the city of lean. J Drug Educ. 2003;33(4):415-25. [Pubmed]
External Links
Wikipedia
RxList
Drugs.com

REFERENCES

  • Peters RJ Jr, Kelder SH, Markham CM, Yacoubian GS Jr, Peters LA, Ellis A: Beliefs and social norms about codeine and promethazine hydrochloride cough syrup (CPHCS) onset and perceived addiction among urban Houstonian adolescents: an addiction trend in the city of lean. J Drug Educ. 2003;33(4):415-25. Pubmed