Cyproheptadine

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

Cyproheptadine
Clinical data
Pronunciation/ˌsaɪproʊˈhɛptədiːn/
Trade namesPeriactin, others
AHFS/Drugs.comMonograph
MedlinePlusa682541
License data
Pregnancy
category
  • AU: A
Routes of
administration		Oral
ATC code
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 binding96 to 99%
MetabolismLiver, mostly CYP3A4 mediated.
Elimination half-life8.6 hours
ExcretionFaecal (2–20%; of which, 34% as unchanged drug) and renal (40%; none as unchanged drug)
Identifiers
  • 4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-methylpiperidine
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.004.482
Chemical and physical data
FormulaC21H21N
Molar mass287.406 g·mol−1
3D model (JSmol)
SMILES
  • c43\C(=C1/CCN(C)CC1)c2ccccc2\C=C/c3cccc4
  • 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
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It was patented in 1959 and came into medical use in 1961. In 2021, it was the 280th most commonly prescribed medication in the United States, with more than 800,000 prescriptions.

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