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4-Hydroxycoumarins

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Definition: Substances found in many plants, containing the 4-hydroxycoumarin radical. They interfere with vitamin K and the blood clotting mechanism, are tightly protein-bound, inhibit mitochondrial and microsomal enzymes, and are used as oral anticoagulants.  /biosyn permitted if by plant   
Pharmacological Action Anticoagulants; Enzyme Inhibitors
Examples Acenocoumarol; Dicumarol; Ethyl Biscoumacetate; Phenprocoumon; Warfarin 		Other names 4 Hydroxycoumarins
 
SubstanceCAS Registry & nameCategoriesSourceDrugs*
3-benzoyl-7-dimethylamino-4-hydroxycoumarin  0   *4-Hydroxycoumarins. Mol Divers. 2009 May;13(2):253-60
4-(bis(4-hydroxy-2-oxo-2H-benzopyran-3-yl)methyl)benzophenone  0   *Benzophenones *4-Hydroxycoumarins. Proc Natl Acad Sci U S A 2006 Jun 27;103(26):10080-5
derrusnine  0   *4-Hydroxycoumarins. Ann Pharm Fr 2002 Sep;60(5):314-7
NSC 158393  0   *4-Hydroxycoumarins. J Med Chem 1996 Jun 21;39(13):2472-81
cyclocumarol  518-20-7   *4-Hydroxycoumarins.
3-phenoxy-4-hydroxycoumarin  0   *4-Hydroxycoumarins. Bioorg Khim 1995 Oct;21(10):809-15
PD 099560  155758-74-0   *4-Hydroxycoumarins. J Med Chem 1994 Aug 19;37(17):2664-77
4-hydroxycoumarin  1076-38-6   *4-Hydroxycoumarins. Clin Exp Immunol 1991;84(2):317
3-(4-azidobenzyl)-4-hydroxycoumarin  133950-79-5   *Azides *4-Hydroxycoumarins. J Biol Chem 1991;266(8):4789
3-(4-azido-5-iodosalicylamido)-4-hydroxycoumarin  132031-99-3   *Azides *4-Hydroxycoumarins. Biochem Biophys Res Commun 1990;172(2):415
3,8-dihydroxy-4-methoxycoumarin  125124-65-4   *4-Hydroxycoumarins Drugs, Chinese Herbal. Yao Hsueh Hsueh Pao 1989;24(10):744
3,8-dihydroxy-4-methoxy-2-oxo-2-H-1-benzopyran-5-carboxylic acid  125124-66-5   *4-Hydroxycoumarins Drugs, Chinese Herbal. Yao Hsueh Hsueh Pao 1989;24(10):744
5,8-dihydroxy-7-(4-hydroxy-5-methylcoumarin-3-yl)coumarin  125124-67-6   *4-Hydroxycoumarins Drugs, Chinese Herbal. Yao Hsueh Hsueh Pao 1989;24(10):744
difethialone  104653-34-1 2H-1-Benzothiopyran-2-one, 3-(3-(4'-bromo(1,1'-biphenyl)-4-yl)-1,2,3,4-tetrahydro-1-naphthalenyl)-4-hydroxy  *4-Hydroxycoumarins. Ann Rech Vet 1989;20(2):159
flocoumafen  90035-08-8 2H-1-Benzopyran-2-one, 4-hydroxy-3-(1,2,3,4-tetrahydro-3-(4-((4-(trifluoromethyl)phenyl)methoxy)phenyl)-1-naphthalenyl)  *4-Hydroxycoumarins. J Hyg (Lond) 1985;95(3):623
fumarin  117-52-2   *4-Hydroxycoumarins. J Hyg Epidemiol Microbiol Immunol 1982;26(2):125
bromadiolone  28772-56-7 3-(3-(4'-bromo(1,1'-biphenyl)-4-yl)-3-hydroxy-1- phenylpropyl)-4-hydroxy-2H-1-benzopyran-2-one  *4-Hydroxycoumarins.
Pharma Action Anticoagulants ; Rodenticides 		J Hyg (Lond) 1980;84(2):263; J Hyg (Lond) 83(2):348;1979
thiol reductone  69538-20-1   *4-Hydroxycoumarins. J Nutr Sci Vitaminol 24(3):263;1978
bromfenacoum  56073-10-0 2H-1-Benzopyran-2-one, 3-(3-(4'-bromo(1,1'-biphenyl)-4-yl)-1,2,3,4-tetrahydro-1-naphthalenyl)-4-hydroxy  *4-Hydroxycoumarins.
Pharma Action Anticoagulants ; Rodenticides 		J Assoc Off Anal Chem 1979;62(6):1297; J Hyg (Lond) 1979;83(2):345; J Hyg (Lond) 1980;84(1):127; J Hyg (Lond) 1980;84(2):263; J Hyg (Lond) 77(3):419;1976; J Hyg (Lond) 77(3):427;1976; J Hyg (Lond) 81(2):197;1978
difenacoum  56073-07-5 3-(3-p-diphenyl-1,2,3,4-tetrahydronaphth-1-yl) -4-hydroxycoumarin  *4-Hydroxycoumarins.
Pharma Action Anticoagulants ; Pesticides ; Rodenticides 		J Hyg (Lond) 1979;83(2):345; J Hyg (Lond) 1980;84(1):127; J Hyg (Lond) 1980;84(2):263; J Hyg 74(3):441;1975; J Hyg 74(3):449;1975
antivitamins K  0   *Indenes *4-Hydroxycoumarins Vitamin K/*antagonists & inhibitors.
Pharma Action Anticoagulants 		Bull Soc Sci MedGrande Duche Luxemb 112(2):163;1975
clocoumarol  35838-63-2 3-(1-(4-(2-chloroethyl)phenyl)butyl)-4-hydroxy-2H-1-benzopyran-2-one  *4-Hydroxycoumarins. Arch Int Pharmacodyn Ther 208(2):369;1974; Drug Metab Dispos 1979;7(6):449; J Med Chem 20(4):604;1977; Pharm Acta Helv 53(8):221;1978
phepromaron  15620-34-5   *4-Hydroxycoumarins. Farm Zh 27(5):48;1972; Farm Zh 4:89;1978; Farmatsiia 23(5):90;1974; Kardiologiia 17(5):79;1977
coumatetralyl  5836-29-3 4-hydroxy-3-(1,2,3,4-tetrahydro-1-naphthalenyl)-2H-1-benzopyran-2-one  *4-Hydroxycoumarins. J Hyg (London) 1980;84(1):127; J Hyg(Lond) 1979;83(2):345; Vet Rec 100(17):371;1977

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Sources: NLM Medical Subject Headings, NIH UMLS, Drugs@FDA, FDA AERS original data copyright United States Government. No endorsement implied. Last modified 6/6/2012
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