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

• ChemBase ID: 822
• Molecular Formular: C18H16O3
• Molecular Mass: 280.31784
• Monoisotopic Mass: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-hydroxy-3-(1-phenylpropyl)-4H-chromen-4-one
• IUPAC Traditional name: phenprocumonum
• Brand Name: Falithiom; Falithrom; Fencumar; Liquamar; Marcoumar; Marcumar; Marcuphen
• Synonyms: Fenprocumone [DCIT]; Phenprocoumarol; Phenprocoumarole; Phenprocoumone; Phenprocumone; Phenprocoumon

Database IDs

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

CALCULATED PROPERTIES

JChem

• Acid pKa: 7.65095
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 4.507917
• LogD (pH = 7.4): 4.3176107
• Log P: 4.510973
• Molar Refractivity: 90.7693 cm^3
• Polarizability: 31.34614 Å^3
• Polar Surface Area: 46.53 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 3.7
• LOG S: -3.77
• Solubility (Water): 4.72e-02 g/l

PROPERTIES

Physical Property

• Solubility: 12.9 mg/L
• Hydrophobicity(logP): 4.4

DETAILS

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