Chlorpromazine

	Chlorpromazine
	Systematic (IUPAC) name
	3-(2-chloro-10H-phenothiazin-10-yl)-N,N-dimethyl-propan-1-amine
	Identifiers
CAS number	50-53-3 (free base); 69-09-0 (hydrochloride)
ATC code	N05AA01
PubChem	2726
DrugBank	DB00477
ChemSpider	2625
	Chemical data
Formula	C17H19Template:OrganicBoxTemplate:OrganicBoxTemplate:OrganicBoxTemplate:OrganicBoxTemplate:OrganicBoxTemplate:OrganicBoxClTemplate:OrganicBoxTemplate:OrganicBoxTemplate:OrganicBoxTemplate:OrganicBoxTemplate:OrganicBoxTemplate:OrganicBoxN2Template:OrganicBoxTemplate:OrganicBoxTemplate:OrganicBoxTemplate:OrganicBoxSTemplate:OrganicBoxTemplate:OrganicBoxTemplate:OrganicBoxTemplate:OrganicBoxTemplate:OrganicBox
Mol. mass	318.86 g/mol (free base); 355.33 g/mol (hydrochloride)
SMILES	eMolecules & PubChem
	Pharmacokinetic data
Bioavailability	10–80% (Oral; large interindividual variation)
Protein binding	90–99%
Metabolism	Liver, mostly CYP2D6-mediated
Half life	30 hours
Excretion	Urine (43–65% in 24 hrs)
	Therapeutic considerations
Licence data	US FDA:link
Pregnancy cat.	C(AU) C(US)
Legal status	℞ Prescription only
Routes	Oral (tablets and syrup available), rectal, IM, IV infusion

Chlorpromazine, also known by its trade name Thorazine, is an antipsychotic drug. It is typically made to treat Schizophrenia, and treat bipolar disorder in the past^[when?]. It has been shown to help uncontrollable hiccups disappear. It is also used to help with nausea and vomiting.^[2] Chlorpromazine was developed in 1950, making it the oldest antipsychotic drug.^[3]

An advert for Thorazine (which contains Chlorpromazine) from the 1960s.

Chlorpromazine Media

Three common metabolites of chlorpromazine

References

↑ ^1.0 ^1.1 ^1.2 ^1.3 PRODUCT INFORMATION LARGACTIL. TGA eBusiness Services (28 August 2012)Sanofi Aventis Pty Ltd. Retrieved 8 December 2013.
↑ ChlorproMAZINE Monograph for Professionals (in en). Drugs.com. Retrieved 2022-09-22.
↑ López-Muñoz, Francisco. History of the Discovery and Clinical Introduction of Chlorpromazine. Annals of Clinical Psychiatry 17 (3) (2005-07-01). p. 113–135. doi:10.1080/10401230591002002.

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[TGA-1] 1.0 ^1.1 ^1.2 ^1.3 PRODUCT INFORMATION LARGACTIL. TGA eBusiness Services (28 August 2012)Sanofi Aventis Pty Ltd. Retrieved 8 December 2013.

[2] ChlorproMAZINE Monograph for Professionals (in en). Drugs.com. Retrieved 2022-09-22.

[3] López-Muñoz, Francisco. History of the Discovery and Clinical Introduction of Chlorpromazine. Annals of Clinical Psychiatry 17 (3) (2005-07-01). p. 113–135. doi:10.1080/10401230591002002.

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Chlorpromazine
Systematic (IUPAC) name
3-(2-chloro-10H-phenothiazin-10-yl)-N,N-dimethyl-propan-1-amine
Identifiers
CAS number	50-53-3 (free base) 69-09-0 (hydrochloride)
ATC code	N05AA01
PubChem	2726
DrugBank	DB00477
ChemSpider	2625
Chemical data
Formula	C₁₇H₁₉Template:OrganicBox Template:OrganicBox Template:OrganicBox Template:OrganicBox Template:OrganicBox Template:OrganicBox Cl Template:OrganicBox Template:OrganicBox Template:OrganicBox Template:OrganicBox Template:OrganicBox Template:OrganicBox N₂Template:OrganicBox Template:OrganicBox Template:OrganicBox Template:OrganicBox S Template:OrganicBox Template:OrganicBox Template:OrganicBox Template:OrganicBox Template:OrganicBox
Mol. mass	318.86 g/mol (free base) 355.33 g/mol (hydrochloride)
SMILES	eMolecules & PubChem
Pharmacokinetic data
Bioavailability	10–80% (Oral; large interindividual variation)^[1]
Protein binding	90–99%^[1]
Metabolism	Liver, mostly CYP2D6-mediated^[1]
Half life	30 hours
Excretion	Urine (43–65% in 24 hrs)^[1]
Therapeutic considerations
Licence data	US FDA:link
Pregnancy cat.	C(AU) C(US)
Legal status	℞ Prescription only
Routes	Oral (tablets and syrup available), rectal, IM, IV infusion