1-methyl-4-{tricyclo[9.4.0.0^{3,8}]pentadeca-1(11),3(8),4,6,9,12,14-heptaen-2-ylidene}piperidine

• ChemBase ID: 317
• Molecular Formular: C21H21N
• Molecular Mass: 287.39814
• Monoisotopic Mass: 287.16739968
• SMILES: N1(CCC(=C2c3c(C=Cc4c2cccc4)cccc3)CC1)C
• Canonical SMILES: CN1CCC(=C2c3ccccc3C=Cc3c2cccc3)CC1
• 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
• InChIKey: JJCFRYNCJDLXIK-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-methyl-4-{tricyclo[9.4.0.0^{3,8}]pentadeca-1(11),3(8),4,6,9,12,14-heptaen-2-ylidene}piperidine; 1-methyl-4-{tricyclo[9.4.0.0^3,^8]pentadeca-1(11),3,5,7,9,12,14-heptaen-2-ylidene}piperidine
• IUPAC Traditional name: cyproheptadine; periactin
• Brand Name: Cypoheptadine; Cyproheptadiene; Cyproheptadine Hcl; Dibenzosuberonone/Cyproheptadine; Dronactin; Eiproheptadine; Periactin; Periactine; Periactinol; Peritol
• Synonyms: Cyproheptadine

Database IDs

• CAS Number: 129-03-3
• PubChem SID: 46508613; 160963780
• PubChem CID: 2913
• CHEBI ID: 4046
• ATC CODE: R06AX02
• CHEMBL: 516
• Chemspider ID: 2810
• DrugBank ID: DB00434
• IUPHAR ligand ID: 277
• KEGG ID: D07765
• Unique Ingredient Identifier: 2YHB6175DO
• Wikipedia Title: Cyproheptadine
• Medline Plus: a682541

CALCULATED PROPERTIES

JChem

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 1.8782412
• LogD (pH = 7.4): 3.6462429
• Log P: 4.3828416
• Molar Refractivity: 105.1742 cm^3
• Polarizability: 36.445183 Å^3
• Polar Surface Area: 3.24 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 5.02
• LOG S: -4.33
• Solubility (Water): 1.36e-02 g/l

PROPERTIES

Physical Property

• Solubility: Soluble
• Hydrophobicity(logP): 4.7

Pharmacology Properties

• Admin Routes: Oral
• Excretion: Fecal and renal
• Half Life: 8.6 hours
• Metabolism: Hepatic and renal
• Protein Bound: 96 to 99%
• Legal Status: P (UK)
• Pregnancy Category: B (US)

DETAILS

DrugBank - DB00434

• Drug Groups: approved
• Description: A serotonin antagonist and a histamine H1 blocker used as antipruritic, appetite stimulant, antiallergic, and for the post-gastrectomy dumping syndrome, etc. [PubChem]
• Indication: For treatment of perennial and seasonal allergic rhinitis, vasomotor rhinitis, allergic conjunctivitis due to inhalant allergens and foods, mild uncomplicated allergic skin manifestations of urticaria and angioedema, amelioration of allergic reactions to blood or plasma, cold urticaria, dermatographism, and as therapy for anaphylactic reactions adjunctive to epinephrine.
• Pharmacology: Cyproheptadine is a piperidine antihistamine. Unlike other antihistamines, this drug also antagonizes serotonin receptors. This action makes Cyproheptadine useful in conditions such as vascular headache and anorexia. Cyproheptadine does not prevent the release of histamine but rather competes with free histamine for binding at HA-receptor sites. Cyproheptadine competitively antagonizes the effects of histamine on HA-receptors in the GI tract, uterus, large blood vessels, and bronchial smooth muscle. Most antihistamines possess significant anticholinergic properties, but Cyproheptadine exerts only weak anticholinergic actions. Blockade of central muscarinic receptors appears to account for Cyproheptadine's antiemetic effects, although the exact mechanism is unknown. Cyproheptadine also competes with serotonin at receptor sites in smooth muscle in the intestines and other locations. Antagonism of serotonin on the appetite center of the hypothalamus may account for Cyproheptadine's ability to stimulate appetite. Cyproheptadine also has been used to counter vascular headaches, which many believe are caused by changes in serotonin activity, however it is unclear how Cyproheptadine exerts a beneficial effect on this condition.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic (cytochrome P-450 system) and some renal.
• Absorption: Well absorbed after oral administration.
• Protein Binding: 96 to 99%
• Elimination: After a single 4 mg oral dose of14C-labelled cyproheptadine HCl in normal subjects, given as tablets 2% to 20% of the radioactivity was excreted in the stools. At least 40% of the administered radioactivity was excreted in the urine.
• References: Tokunaga S, Takeda Y, Shinomiya K, Hirase M, Kamei C: Effects of some H1-antagonists on the sleep-wake cycle in sleep-disturbed rats. J Pharmacol Sci. 2007 Feb;103(2):201-6. Epub 2007 Feb 8. [Pubmed]
• External Links: Wikipedia; RxList; Drugs.com

REFERENCES

• Tokunaga S, Takeda Y, Shinomiya K, Hirase M, Kamei C: Effects of some H1-antagonists on the sleep-wake cycle in sleep-disturbed rats. J Pharmacol Sci. 2007 Feb;103(2):201-6. Epub 2007 Feb 8. Pubmed