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编号: 317
• 分子式: C21H21N
• 平均质量: 287.39814
• 单一同位素质量: 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

名称和登记号

名称

• IUPAC标准名: 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传统名: cyproheptadine; periactin
• 商标名: Cypoheptadine; Cyproheptadiene; Cyproheptadine Hcl; Dibenzosuberonone/Cyproheptadine; Dronactin; Eiproheptadine; Periactin; Periactine; Periactinol; Peritol
• 别名: Cyproheptadine

登记号

• CAS号: 129-03-3
• PubChem SID: 46508613; 160963780
• PubChem CID: 2913
• CHEBI ID: 4046
• ATC码: R06AX02
• CHEMBL: 516
• Chemspider ID: 2810
• DrugBank ID: DB00434
• IUPHAR配体索引: 277
• KEGG ID: D07765
• 美国药典/FDA物质标识码: 2YHB6175DO
• 维基百科标题: Cyproheptadine
• Medline Plus: a682541

理论计算性质

JChem

• 质子受体: 1
• 质子供体: 0
• LogD (pH = 5.5): 1.8782412
• LogD (pH = 7.4): 3.6462429
• Log P: 4.3828416
• 摩尔折射率: 105.1742 cm^3
• 极化性: 36.445183 Å^3
• 极化表面积: 3.24 Å^2
• 可自由旋转的化学键: 0
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 5.02
• LOG S: -4.33
• 溶解度: 1.36e-02 g/l

分子性质

理化性质

• 溶解度: Soluble
• 疏水性(logP): 4.7

药理学性质

• 给药途径: Oral
• 排泄: Fecal and renal
• 半衰期: 8.6 hours
• 代谢: Hepatic and renal
• 蛋白结合率: 96 to 99%
• 法定药品分级: P (UK)
• 妊娠期药物分类: B (US)

详细说明

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

参考文献

• 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