dimethyl[1-(10H-phenothiazin-10-yl)propan-2-yl]amine

• ChemBase编号: 940
• 分子式: C17H20N2S
• 平均质量: 284.4191
• 单一同位素质量: 284.13471965
• SMILES: S1c2c(N(CC(N(C)C)C)c3c1cccc3)cccc2
• Canonical SMILES: CN(C(CN1c2ccccc2Sc2c1cccc2)C)C
• InChI: InChI=1S/C17H20N2S/c1-13(18(2)3)12-19-14-8-4-6-10-16(14)20-17-11-7-5-9-15(17)19/h4-11,13H,12H2,1-3H3
• InChIKey: PWWVAXIEGOYWEE-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: dimethyl[1-(10H-phenothiazin-10-yl)propan-2-yl]amine
• IUPAC传统名: promethazine
• 商标名: Allergan; Aprobit; Avomine; Dimapp; Diphergan; Diprazine; Diprozin; Dorme; Duplamin; Fargan; Fellozine; Fenazil; Fenergan; Fenetazina; Genphen; Hiberna; Histargan; Iergigan; Isophenergan; Lercigan; Lergigan; Mymethazine Fortis; Phargan; Phenargan; Phencen; Phenergan; Phenergan Fortis; Phensedyl; Pilpophen; Pipolphen; Procit; Prometasin; Prometazin; Prometh Fortis; Prometh Plain; Promethacon; Promethaine; Promethegan; Prorex; Protazine; Provigan; Pyrethia; Pyrethiazine; Remsed; Romergan; Synalgos; Tanidil; Thiergan; Valergine; Vallergine; Zipan-25
• 别名: Lilly 1516; Isopromethazine; Proazaimine; Proazamine; Promazinamide; Promethazin; Promethazine Hcl; Promethiazine; Promezathine; Prothazin; Prothazine; Prometazine; Promethazine; PROMETHAZINE HYDROCHLORIDE

登记号

• CAS号: 60-87-7; 58-33-3
• EC号: 200-375-2
• PubChem SID: 46507798; 160964403
• PubChem CID: 4927
• CHEBI ID: 8461
• ATC码: R06AD05; R06AD02; D04AA10
• CHEMBL: 643
• Chemspider ID: 4759
• DrugBank ID: DB01069
• KEGG ID: D00494
• 美国药典/FDA物质标识码: FF28EJQ494
• 维基百科标题: Promethazine
• Medline Plus: a682284

理论计算性质

JChem

• 质子受体: 2
• 质子供体: 0
• LogD (pH = 5.5): 1.0650802
• LogD (pH = 7.4): 2.6373293
• Log P: 4.287571
• 摩尔折射率: 88.5049 cm^3
• 极化性: 34.154385 Å^3
• 极化表面积: 6.48 Å^2
• 可自由旋转的化学键: 3
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 4.52
• LOG S: -4.07
• 溶解度: 2.45e-02 g/l

分子性质

理化性质

• 溶解度: Freely soluble
• 熔点: 230-232
• 疏水性(logP): 4.4

安全信息

• 保存条件: Room Temperature (15-30°C)
• RTECS编号: SO8225000

药理学性质

• 给药途径: Oral, rectal, IV, IM, topical
• 生物利用度: 88% absorbed but after first-pass metabolism reduced to 25% absolute bioavailability
• 排泄: Renal and biliary
• 半衰期: 16-19 hours
• 代谢: Hepatic glucuronidation and sulfoxidation
• 蛋白结合率: 93%
• 法定药品分级: ; (injection POM(UK)); Rx-only (US)
• 妊娠期药物分类: C (Australia); C (US)

详细说明

MP Biomedicals - 02156385

Hydrochloride

DrugBank - DB01069

• Drug Groups: approved
• Description: A phenothiazine derivative with histamine H1-blocking, antimuscarinic, and sedative properties. It is used as an antiallergic, in pruritus, for motion sickness and sedation, and also in animals. [PubChem]
• Indication: For the treatment of allergic disorders, and nausea/vomiting.
• Pharmacology: Promethazine, a phenothiazine, is an H1-antagonist with anticholinergic, sedative, and antiemetic effects and some local anesthetic properties. Promethazine is used as an antiemetic or to prevent motion sickness.
• Toxicity: Symptoms of overdose include mild depression of the central nervous system and cardiovascular system to profound hypotension, respiratory depression, unconsciousness, and sudden death. Other reported reactions include hyperreflexia, hypertonia, ataxia, athetosis, and extensor-plantar reflexes (Babinski reflex). LD₅₀=55mg/kg (I.V. in mice)
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic
• Absorption: On average, 88% of a promethazine dose is absorbed after oral administration; however, the absolute bioavailability is only 25% because of first-pass clearance.
• Half Life: 16-19 hours
• Protein Binding: 93%
• Elimination: Promethazine hydrochloride is metabolized in the liver, with the sulfoxides of promethazine and N-desmethylpromethazine being the predominant metabolites appearing in the urine.
• References: Peters RJ Jr, Kelder SH, Markham CM, Yacoubian GS Jr, Peters LA, Ellis A: Beliefs and social norms about codeine and promethazine hydrochloride cough syrup (CPHCS) onset and perceived addiction among urban Houstonian adolescents: an addiction trend in the city of lean. J Drug Educ. 2003;33(4):415-25. [Pubmed]
• External Links: Wikipedia; RxList; Drugs.com

参考文献

• Peters RJ Jr, Kelder SH, Markham CM, Yacoubian GS Jr, Peters LA, Ellis A: Beliefs and social norms about codeine and promethazine hydrochloride cough syrup (CPHCS) onset and perceived addiction among urban Houstonian adolescents: an addiction trend in the city of lean. J Drug Educ. 2003;33(4):415-25. Pubmed