Acenocoumarol

Title: Acenocoumarol
CAS Registry Number: 152-72-7
CAS Name: 4-Hydroxy-3-[1-(4-nitrophenyl)-3-oxobutyl]-2H-1-benzopyran-2-one
Additional Names: 3-(a-acetonyl-p-nitrobenzyl)-4-hydroxycoumarin; 3-(a-p-nitrophenyl-b-acetylethyl)-4-hydroxycoumarin; acenocoumarin; nicoumalone
Manufacturers' Codes: G-23350
Trademarks: Mini-Sintrom (Novartis); Sinthrome (Novartis); Sintrom (Novartis)
Molecular Formula: C19H15NO6
Molecular Weight: 353.33
Percent Composition: C 64.59%, H 4.28%, N 3.96%, O 27.17%
Literature References: Vitamin K antagonist; structurally similar to warfarin, q.v. Prepn: W. Stoll, F. Litvan, US 2648682 (1953 to Geigy); I. C. Ivanov et al., Arch. Pharm. 323, 521 (1990). Resolution and abs config of enantiomers: C. R. Wheeler, W. F. Trager, J. Med. Chem. 22, 1122 (1979). Pharmacology and toxicity: M. Leroux, B. Jamain, Therapie 11, 85 (1956). GC-MS determn in plasma: F. Pommier et al., J. Chromatogr. B 654, 35 (1994). Clinical trial: D. P. M. Brandjes et al., N. Engl. J. Med. 327, 1485 (1992).
Properties: Crystals, mp 196-199°. Sparingly sol in water and most organic solvents. Forms water-sol salt with alkalies. LD50 orally in mice, rats: 1470, 1000 mg/kg (Leroux, Jamain).
Melting point: mp 196-199°
Toxicity data: LD50 orally in mice, rats: 1470, 1000 mg/kg (Leroux, Jamain)
Therap-Cat: Anticoagulant.
Keywords: Anticoagulant.
Aceperone Acephate Acepromazine Acequinocyl Acerin

Acenocoumarol
Acenocoumarol.svg
Systematic (IUPAC) name
(RS)-4-hydroxy-3-[1-(4-nitrophenyl)-3-oxobutyl]-2H-chromen-2-one
Clinical data
AHFS/Drugs.com Micromedex Detailed Consumer Information
Pregnancy cat. X
Legal status POM (UK)
Routes Oral
Pharmacokinetic data
Metabolism Hepatic
Half-life 8 to 11 hours
Identifiers
CAS number 152-72-7 YesY
ATC code B01AA07
PubChem CID 9052
DrugBank DB01418
ChemSpider 10443441 YesY
UNII I6WP63U32H YesY
KEGG D07064 YesY
ChEBI CHEBI:53766 YesY
ChEMBL CHEMBL397420 YesY
Chemical data
Formula C19H15NO6 
Mol. mass 353.326 g⋅mol−1
 YesY (what is this?)  (verify)

Acenocoumarol is an anticoagulant that functions as a vitamin K antagonist (like warfarin). It is a derivative of coumarin and is marketed under the brand names Sintrom and Sinthrome.