2-hydroxy-3-(1-phenylpropyl)-4H-chromen-4-one

• ChemBase编号: 822
• 分子式: C18H16O3
• 平均质量: 280.31784
• 单一同位素质量: 280.10994437
• SMILES: o1c(O)c(C(CC)c2ccccc2)c(=O)c2c1cccc2
• Canonical SMILES: CCC(c1c(O)oc2c(c1=O)cccc2)c1ccccc1
• InChI: InChI=1S/C18H16O3/c1-2-13(12-8-4-3-5-9-12)16-17(19)14-10-6-7-11-15(14)21-18(16)20/h3-11,13,20H,2H2,1H3
• InChIKey: QNDUUBVQYBBRBW-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 2-hydroxy-3-(1-phenylpropyl)-4H-chromen-4-one
• IUPAC传统名: phenprocumonum
• 商标名: Falithiom; Falithrom; Fencumar; Liquamar; Marcoumar; Marcumar; Marcuphen
• 别名: Fenprocumone [DCIT]; Phenprocoumarol; Phenprocoumarole; Phenprocoumone; Phenprocumone; Phenprocoumon

登记号

• CAS号: 435-97-2
• PubChem SID: 160964285
• PubChem CID: 54680692

理论计算性质

JChem

• Acid pKa: 7.65095
• 质子受体: 3
• 质子供体: 1
• LogD (pH = 5.5): 4.507917
• LogD (pH = 7.4): 4.3176107
• Log P: 4.510973
• 摩尔折射率: 90.7693 cm^3
• 极化性: 31.34614 Å^3
• 极化表面积: 46.53 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: 3.7
• LOG S: -3.77
• 溶解度: 4.72e-02 g/l

分子性质

理化性质

• 溶解度: 12.9 mg/L
• 疏水性(logP): 4.4

详细说明

DrugBank - DB00946

• Drug Groups: approved
• Description: Coumarin derivative that acts as a long acting oral anticoagulant. [PubChem]
• Indication: Used for the prevention and treatment of thromboembolic disease including venous thrombosis, thromboembolism, and pulmonary embolism as well as for the prevention of ischemic stroke in patients with atrial fibrillation (AF).
• Pharmacology: Phenprocoumon, a coumarin anticoagulant, thins the blood by antagonizing vitamin K which is required for the production of clotting factors in the liver. Anticoagulants such as phenprocoumon have no direct effect on an established thrombus, nor do they reverse ischemic tissue damage (damage caused by an inadequate blood supply to an organ or part of the body). However, once a thrombus has occurred, the goal of anticoagulant treatment is to prevent further extension of the formed clot and prevent secondary thromboembolic complications which may result in serious and possibly fatal sequelae.
• Toxicity: 50=500 mg/kg. Symptoms of overdose includes suspected or overt abnormal bleeding (e.g., appearance of blood in stools or urine, hematuria, excessive menstrual bleeding, melena, petechiae, excessive bruising or persistent oozing from superficial injuries).
• Affected Organisms: Humans and other mammals
• Biotransformation: Phenprocoumon is stereoselectively metabolized by hepatic microsomal enzymes (cytochrome P-450) to inactive hydroxylated metabolites (predominant route) and by reductases to reduced metabolites. Cytochrome P450 2C9 is the principal form of human liver P-450 responsible for metabolism.
• Absorption: Bioavailability is close to 100%
• Half Life: 5-6 days
• Protein Binding: 99%
• External Links: Wikipedia