Cyproheptadine

Cyproheptadine
Clinical data
Pronunciation	/ˌsaɪproʊˈhɛptədiːn/
Trade names	Periactin, others
AHFS/Drugs.com	Monograph
MedlinePlus	a682541
License data	US DailyMed: Cyproheptadine;
Pregnancy; category	AU: A; ;
Routes of; administration	Oral
ATC code	R06AX02 (WHO) ;
Legal status
Legal status	AU: S3 (Pharmacist only); CA: OTC; UK: General sales list (GSL, OTC); US: ℞-only; In general: Over-the-counter (OTC);
Pharmacokinetic data
Protein binding	96 to 99%
Metabolism	Liver, mostly CYP3A4 mediated.
Elimination half-life	8.6 hours
Excretion	Faecal (2–20%; of which, 34% as unchanged drug) and renal (40%; none as unchanged drug)
Identifiers
	IUPAC name 4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-methylpiperidine;
CAS Number	129-03-3 969-33-5 (hydrochloride);
PubChem CID	2913;
IUPHAR/BPS	277;
DrugBank	DB00434 ;
ChemSpider	2810 ;
UNII	2YHB6175DO;
KEGG	D07765 ;
ChEBI	CHEBI:4046 ;
ChEMBL	ChEMBL516 ;
CompTox Dashboard (EPA)	DTXSID8022872 ;
ECHA InfoCard	100.004.482
Chemical and physical data
Formula	C21H21N
Molar mass	287.406 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES c43\C(=C1/CCN(C)CC1)c2ccccc2\C=C/c3cccc4;
	InChI InChI=1S/C21H21N/c1-22-14-12-18(13-15-22)21-19-8-4-2-6-16(19)10-11-17-7-3-5-9-20(17)21/h2-11H,12-15H2,1H3 ; Key:JJCFRYNCJDLXIK-UHFFFAOYSA-N ;
	(verify)

Cyproheptadine, sold under the brand name Periactin among others, is a first-generation antihistamine with additional anticholinergic, antiserotonergic, and local anesthetic properties.

It was patented in 1959 and came into medical use in 1961.^[5] In 2022, it was the 293rd most commonly prescribed medication in the United States, with more than 400,000 prescriptions.^[6]^[7]

^ "Cyproheptadine". Dictionary.com Unabridged (Online). n.d.
^ Gunja N, Collins M, Graudins A (2004). "A comparison of the pharmacokinetics of oral and sublingual cyproheptadine". Journal of Toxicology. Clinical Toxicology. 42 (1): 79–83. doi:10.1081/clt-120028749. PMID 15083941. S2CID 20196551.
^ ^a ^b "Cyproheptadine Hydrochloride tablet [Boscogen, Inc.]" (PDF). DailyMed. U.S. National Library of Medicine. November 2010. Retrieved 26 October 2013.
^ ^a ^b "Product Information: Periactin (cyproheptadine hydrochloride)" (PDF). Aspen Pharmacare Australia. Aspen Pharmacare Australia Pty Ltd. 17 November 2011. Archived from the original (PDF) on 29 October 2013. Retrieved 26 October 2013.
^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 547. ISBN 9783527607495.
^ "The Top 300 of 2022". ClinCalc. Archived from the original on 30 August 2024. Retrieved 30 August 2024.
^ "Cyproheptadine Drug Usage Statistics, United States, 2013 - 2022". ClinCalc. Retrieved 30 August 2024.

[1] "Cyproheptadine". Dictionary.com Unabridged (Online). n.d.

[pmid15083941-2] Gunja N, Collins M, Graudins A (2004). "A comparison of the pharmacokinetics of oral and sublingual cyproheptadine". Journal of Toxicology. Clinical Toxicology. 42 (1): 79–83. doi:10.1081/clt-120028749. PMID 15083941. S2CID 20196551.

[DM-3] "Cyproheptadine Hydrochloride tablet [Boscogen, Inc.]" (PDF). DailyMed. U.S. National Library of Medicine. November 2010. Retrieved 26 October 2013.

[TGA-4] "Product Information: Periactin (cyproheptadine hydrochloride)" (PDF). Aspen Pharmacare Australia. Aspen Pharmacare Australia Pty Ltd. 17 November 2011. Archived from the original (PDF) on 29 October 2013. Retrieved 26 October 2013.

[Fis2006-5] Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 547. ISBN 9783527607495.

[Top_300_of_2022-6] "The Top 300 of 2022". ClinCalc. Archived from the original on 30 August 2024. Retrieved 30 August 2024.

[7] "Cyproheptadine Drug Usage Statistics, United States, 2013 - 2022". ClinCalc. Retrieved 30 August 2024.

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Clinical data


Pronunciation	/ˌsaɪproʊˈhɛptədiːn/^[1]
Trade names	Periactin, others
AHFS/Drugs.com	Monograph
MedlinePlus	a682541
License data	US DailyMed: Cyproheptadine
Pregnancy category	AU: A
Routes of administration	Oral
ATC code	R06AX02 (WHO)
Legal status
Legal status	AU: S3 (Pharmacist only) CA: OTC UK: General sales list (GSL, OTC) US: ℞-only In general: Over-the-counter (OTC)
Pharmacokinetic data
Protein binding	96 to 99%
Metabolism	Liver,^[3]^[4] mostly CYP3A4 mediated.
Elimination half-life	8.6 hours^[2]
Excretion	Faecal (2–20%; of which, 34% as unchanged drug) and renal (40%; none as unchanged drug)^[3]^[4]
Identifiers
IUPAC name 4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-methylpiperidine
CAS Number	129-03-3^Y 969-33-5 (hydrochloride)
PubChem CID	2913
IUPHAR/BPS	277
DrugBank	DB00434^Y
ChemSpider	2810^Y
UNII	2YHB6175DO
KEGG	D07765^Y
ChEBI	CHEBI:4046^Y
ChEMBL	ChEMBL516^Y
CompTox Dashboard (EPA)	DTXSID8022872
ECHA InfoCard	100.004.482
Chemical and physical data
Formula	C₂₁H₂₁N
Molar mass	287.406 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES c43\C(=C1/CCN(C)CC1)c2ccccc2\C=C/c3cccc4
InChI InChI=1S/C21H21N/c1-22-14-12-18(13-15-22)21-19-8-4-2-6-16(19)10-11-17-7-3-5-9-20(17)21/h2-11H,12-15H2,1H3^Y Key:JJCFRYNCJDLXIK-UHFFFAOYSA-N^Y
(verify)