DT-Web

DB01125 - Anisindione


Identification
Name Anisindione
Accession Number DB01125 (APRD00799)
Type small molecule
Description Anisindione is a synthetic anticoagulant and an indanedione derivative. It prevents the formation of active procoagulation factors II, VII, IX, and X, as well as the anticoagulant proteins C and S, in the liver by inhibiting the vitamin K-mediated gamma-carboxylation of precursor proteins.
Structure
MOL SDF PDB SMILES InChI
Categories (*)
Molecular Weight 252.2647
Groups approved
Monoisotopic Weight 252.07864425
Pharmacology
Indication For the prophylaxis and treatment of venous thrombosis and its extension, the treatment of atrial fibrillation with embolization, the prophylaxis and treatment of pulmonary embolism, and as an adjunct in the treatment of coronary occlusion.
Mechanism of action Like phenindione, to which it is related chemically, anisindione exercises its therapeutic action by reducing the prothrombin activity of the blood. Anisindione prevents the formation of active procoagulation factors II, VII, IX, and X, as well as the anticoagulant proteins C and S, in the liver by inhibiting the vitamin K–mediated gamma-carboxylation of precursor proteins. Anisindione has no direct thrombolytic effect and does not reverse ischemic tissue damage, although it may limit extension of existing thrombi and prevent secondary thromboembolic complications.
Absorption Accumulation does not occur with repeated dosing.
Protein binding Not Known
Biotransformation Not Available
Route of elimination Not Available
Toxicity An overdose is likely to cause abnormal bleeding, for which the symptoms include: bleeding from gums or nose, blood in urine or stools, excessive bleeding from minor cuts, patches of discoloration or bruises on the skin.
Affected organisms
  • Humans and other mammals
Interactions
Drug Interactions
Drug Mechanism of interaction
Acetaminophen Acetaminophen increases the anticoagulant effect of anisindione. Monitor for changes in the therapeutic and adverse effects of anisindione if acetaminophen is initiated, discontinued or dose changed.
Acetylsalicylic acid Acetylsalicylic acid increases effect of the anticoagulant, anisindione.
Allopurinol Allopurinol may increase the anticoagulant effect of anisindione.
Aminoglutethimide Aminoglutethimide may decrease the anticoagulant effect of anisindione.
Amiodarone Amiodarone may increase the anticoagulant effect of anisindione.
Amprenavir Amprenavir may increase the anticoagulant effect of anisindione by increasing its serum concentration.
Aprepitant Aprepitant may decrease the anticoagulant effect of anisindione by decreasing its serum concentration.
Atazanavir The protease inhibitor, atazanavir, may increase the anticoagulant effect of anisindione.
Azathioprine Azathioprine may decrease the anticoagulant effect of anisindione.
Azithromycin Azithromycin may increase the anticoagulant effect of anisindione by increasing its serum concentration.
Betamethasone The corticosteroid, betamethasone, alters the anticoagulant effect of anisindione.
Bosentan Bosentan may decrease the anticoagulant effect of anisindione by increasing its metabolism.
Capecitabine Capecitabine may increase the anticoagulant effect of anisindione by increasing its serum concentration.
Carbamazepine Carbamazepine may decrease the anticoagulant effect of anisindione by decreasing its serum concentration.
Cefotetan The cephalosporin, cefotetan, may increase the anticoagulant effect of anisindione.
Cefoxitin The cephalosporin, cefoxitin, may increase the anticoagulant effect of anisindione.
Ceftriaxone The cephalosporin, ceftriaxone, may increase the anticoagulant effect of anisindione.
Celecoxib Celecoxib may increase the anticoagulant effect of anisindione.
Cholestyramine The bile acid sequestrant, cholestyramine, may decrease the anticoagulant effect of anisindione by decreasing its absorption.
Cimetidine Cimetidine may increase the anticoagulant effect of anisindione.
Ciprofloxacin The quinolone antibiotic, ciprofloxacin, may increase the anticoagulant effect of anisindione.
Cisapride Cisapride may increase the anticoagulant effect of anisindione.
Citalopram The SSRI, citalopram, increases the effect of anticoagulant, anisindione.
Clarithromycin The macrolide, clarithromycin, may increase the anticoagulant effect of anisindione.
Clofibrate The fibrate increases the anticoagulant effect
Colestipol The bile acid sequestrant, colestipol, may decrease the anticoagulant effect of anisindione by decreasing its absorption.
Cyclophosphamide The antineoplastic agent, cyclophosphamide may alter the anticoagulant effect of anisindione.
Danazol The androgen, danazol, may increase the anticoagulant effect of anisindione.
Demeclocycline The tetracycline, demeclocycline, may increase the anticoagulant effect of anisindione.
Dexamethasone The corticosteroid, dexamethasone, alters the anticoagulant effect of anisindione.
Dextrothyroxine The thyroid hormone, dextrothyroxine, increase the anticoagulant effect of anisindione.
Diclofenac The NSAID, diclofenac, may increase the anticoagulant effect of anisindione.
Dicloxacillin Dicloxacillin may decrease the anticoagulant effect of anisindione.
Diflunisal The NSAID, diflunisal, may increase the anticoagulant effect of anisindione.
Disulfiram Disulfiram may increase the anticoagulant effect of anisindione.
Doxycycline The tetracycline, doxycycline, may increase the anticoagulant effect of anisindione.
Erythromycin The macrolide, erythromycin, may increase the anticoagulant effect of anisindione.
Ethchlorvynol Ethchlorvynol may decrease the anticoagulant effect of anisindione.
Ethinyl Estradiol Increased thrombotic risk due to estrogen
Etodolac The NSAID, etodolac, may increase the anticoagulant effect of anisindione.
Etoricoxib Etoricoxib may increase the anticoagulant effect of anisindione.
Fenofibrate Fenofibrate may increase the anticoagulant effect of anisindione.
Fenoprofen The NSAID, fenoprofen, may increase the anticoagulant effect of anisindione.
Fluconazole Fluconazole may increase the serum concentration of anisindione by decreasing its metabolism.
Fludrocortisone The corticosteroid, fludrocortisone, alters the anticoagulant effect of anisindione.
Fluorouracil The antineoplasic agent, fluorouracil, may increase the anticoagulant effect of anisindione.
Fluoxetine The SSRI, fluoxetine, increases the effect of anticoagulant, anisindione.
Fluoxymesterone The androgen, fluoxymesterone, may increase the anticoagulant effect of anisindione.
Flurbiprofen The NSAID, flurbiprofen, may increase the anticoagulant effect anisindione.
Fluvastatin Fluvastatin may increase the anticoagulant effect of anisindione. Monitor for changes in the therapeutic and adverse effects of anisindione if fluvastatin if initiated, discontinued or dose changed.
Fluvoxamine Fluvoxamine may increase the anticoagulant effect of anisindione by increasing its serum concentration.
Fosamprenavir The protease inhibitor, fosamprenavir, may increase the anticoagulant effect of anisindione.
Fosphenytoin Increased hydantoin levels and risk of bleeding
Gefitinib Gefitinib may increase the anticoagulant effect of anisindione.
Gemcitabine Gemcitabine may increase the anticoagulant effect of anisindione.
Gemfibrozil Gemfibrozil may increase the anticoagulant effect of anisindione.
Glutethimide Glutethimide may decrease the anticoagulant effect of anisindione.
Griseofulvin Griseofulvin may decrease the anticoagulant effect of anisindione.
Hydrocortisone The corticosteroid, hydrocortisone, alters the anticoagulant effect of anisindione.
Ibuprofen The NSAID, ibuprofen, may increase the anticoagulant effect of anisindione.
Imatinib Imatinib may increase the anticoagulant effect of anisindione.
Indinavir The protease inhibitor, indinavir, may increase the anticoagulant effect of anisindione.
Indomethacin The NSAID, indomethacin, may increase the anticoagulant effect of anisindione.
Isoniazid Isoniazid may increase the anticoagulant effect of anisindione.
Itraconazole Itraconazole may increase the anticoagulant effect of anisindione.
Ketoconazole Ketoconazole may increase the anticoagulant effect of anisindione.
Ketoprofen The NSAID, ketoprofen, may increase the anticoagulant effect of anisindione.
Ketorolac The NSAID, ketorolac, may increase the anticoagulant effect of anisindione.
Leflunomide Leflunomide may increase the anticoagulant effect of anisindione.
Levamisole Levamisole may increase the anticoagulant effect of anisindione.
Levofloxacin The quinolone antibiotic, levofloxacin, may increase the anticoagulant effect of anisindione.
Levothyroxine The thyroid hormone, levothyroxine, increase the anticoagulant effect of anisindione.
Lovastatin Lovastatin may increase the anticoagulant effect of anisindione. Monitor for changes in the therapeutic and adverse effects of anisindione if lovastatin if initiated, discontinued or dose changed.
Lumiracoxib Lumiracoxib may increase the anticoagulant effect of anisindione.
Medroxyprogesterone Medroxyprogesterone may increase the anticoagulant effect of anisindione.
Mefenamic acid The NSAID, mefanamic acid, may increase the anticoagulant effect of anisindione.
Mefloquine Mefloquine may increase the anticoagulant effect of anisindione.
Meloxicam Meloxicam may increase the anticoagulant effect of anisindione.
Mercaptopurine Mercaptopurine may decrease the anticoagulant effect of anisindione.
Methimazole The antithyroid agent, methimazole, may decrease the anticoagulant effect of anisindione.
Metronidazole Metronidazole may increase the anticoagulant effect of anisindione.
Miconazole Miconazole may increase the serum concentration of anisindione by decreasing its metabolism.
Minocycline The tetracycline, minocycline, may increase the anticoagulant effect of anisindione.
Mitotane Mitotane may decrease the anticoagulant effect of anisindione.
Moxifloxacin The quinolone antibiotic, moxifloxacin, may increase the anticoagulant effect of anisindione.
Nabumetone The NSAID, nabumetone, may increase the anticoagulant effect anisindione.
Nalidixic Acid The quinolone antibiotic, nalidixic acid, may increase the anticoagulant effect of anisindione.
Naproxen The NSAID, naproxen, may increase the anticoagulant effect of anisindione.
Nelfinavir The protease inhibitor, nelfinavir, may increase the anticoagulant effect of anisindione.
Nevirapine Nevirapine may decrease the anticoagulant effect of anisindione.
Norfloxacin The quinolone antibiotic, norfloxacin, may increase the anticoagulant effect of anisindione.
Ofloxacin The quinolone antibiotic, ofloxacin, may increase the anticoagulant effect of anisindione.
Orlistat Orlistat may increase the anticoagulant effect of anisindione.
Oxaprozin The NSAID, oxaprozin, may increase the anticoagulant effect of anisinodione.
Oxyphenbutazone The NSAID, oxyphenbutazone, may increase the anticoagulant effect of anisindione.
Paroxetine The SSRI, paroxetine, increases the effect of the anticoagulant, anisindione.
Pentoxifylline Pentoxifylline may increase the anticoagulant effect of anisindione.
Phenobarbital The barbiturate, phenobarbital, decreases the anticoagulant effect of anisindione.
Phenylbutazone The NSAID, phenylbutazone, may increase the anticoagulant effect of anisindione.
Phenytoin Increased hydantoin levels and risk of bleeding
Piroxicam The NSAID, piroxicam, may increase the anticoagulant effect of anisindione.
Prednisolone The corticosteroid, prednisolone, alters the anticoagulant effect of anisindione.
Prednisone The corticosteroid, prednisone, alters the anticoagulant effect of anisindione.
Primidone The barbiturate, primidone, decreases the anticoagulant effect of anisindione.
Propafenone Propafenone may increase the anticoagulant effect of anisindione.
Propoxyphene Propoxyphene may increase the anticoagulant effect of anisindione.
Propylthiouracil The anti-thyroid agent, propylthiouracil, may decrease the anticoagulant effect of anisindione.
Quinidine Quinidine may increase the anticoagulant effect of anisindione.
Quinine Quinine may increase the anticoagulant effect of anisindione.
Ranitidine Ranitidine may increase the anticoagulant effect of anisindione. (Conflicting evidence)
Rifabutin Rifabutin, may decrease the anticoagulant effect of anisindione.
Rifampin Rifampin may decrease the anticoagulant effect of anisindione.
Telithromycin Telithromycin may increase the anticoagulant effect of anisindione.
Tenoxicam The NSAID, tenoxicam, may increase the anticoagulant effect of anisindione.
Testosterone The androgen may increase the anticoagulant effect of anisindione.
Tetracycline Tetracycline may increase the anticoagulant effect of anisindione.
Tigecycline Tigecycline may increase the anticoagulant effect of anisindione.
Triamcinolone The corticosteroid, triamcinolone, alters the anticoagulant effect of anisindione.
Food Interactions Not Available

Targets


Vitamin K-dependent gamma-carboxylase
Name Vitamin K-dependent gamma-carboxylase
Gene Name GGCX
Pharmacological action yes
Actions inhibitor
References
  • Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. - Pubmed
  • Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. - Pubmed
  • Anisindione - Basic Profile / Key Facts. - Source
  • Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. - Pubmed
DTHybrid score 0.5198

Predictions


Id Partner name Gene Name Score
798 Osteocalcin BGLAP 0.124
19 Coagulation factor VIII F8 0.0706
369 Coagulation factor VII F7 0.0652
1334 Tissue factor pathway inhibitor TFPI 0.0521
239 Coagulation factor X F10 0.0497
3831 Low-density lipoprotein receptor-related protein 1 LRP1 0.0411
2139 Tissue factor F3 0.0381
3851 Serine protease hepsin HPN 0.0363
1245 Vitamin K-dependent protein S PROS1 0.0339
54 Prothrombin F2 0.0315
1959 Platelet factor 4 PF4 0.0299
3865 Serpin B6 SERPINB6 0.0299
1986 Ceruloplasmin CP 0.0299
1547 Coagulation factor XI F11 0.0269
3833 Plasma serine protease inhibitor SERPINA5 0.026
46 Coagulation factor V F5 0.0236
2021 Thrombomodulin THBD 0.0235
2072 Endothelial protein C receptor PROCR 0.023
267 Plasminogen activator inhibitor 1 SERPINE1 0.0196
604 Vitamin K-dependent protein Z PROZ 0.0156
4081 Vitamin K epoxide reductase complex subunit 1-like protein 1 VKORC1L1 0.0156
400 Coagulation factor IX F9 0.0146
5461 Coagulation factor IX F9 0.0146
422 Vitamin K-dependent protein C PROC 0.0127
787 Vitamin K epoxide reductase complex subunit 1 VKORC1 0.0102
3917 Methylenetetrahydrofolate reductase MTHFR 0.0093
243 Ribosyldihydronicotinamide dehydrogenase [quinone] NQO2 0.0086
6020 Aldehyde oxidase AOX1 0.0085
2157 NAD(P)H dehydrogenase [quinone] 1 NQO1 0.0082
3947 Xanthine dehydrogenase/oxidase XDH 0.0076
5718 Cytochrome P450 2A6 CYP2A6 0.006
6024 Cytochrome P450 1A1 CYP1A1 0.0058
6013 Cytochrome P450 2E1 CYP2E1 0.0054
4200 Cytochrome P450 1A2 CYP1A2 0.0048
4024 Mitochondrial glutamate carrier 2 SLC25A18 0.0042
4025 Mitochondrial glutamate carrier 1 SLC25A22 0.0042
4022 Glutamate--ammonia ligase domain-containing protein 1 LGSN 0.0042
4019 Excitatory amino acid transporter 4 SLC1A6 0.0042
919 Glutamate receptor, ionotropic kainate 4 GRIK4 0.0042
920 Glutamate receptor, ionotropic kainate 5 GRIK5 0.0042
4026 Aspartyl aminopeptidase DNPEP 0.0042
4021 Probable glutamyl-tRNA synthetase, mitochondrial EARS2 0.0042
4023 N-acetylglutamate synthase, mitochondrial NAGS 0.0042
1912 Excitatory amino acid transporter 1 SLC1A3 0.0042
4016 Excitatory amino acid transporter 5 SLC1A7 0.0042
1047 Excitatory amino acid transporter 2 SLC1A2 0.0042
922 Glutamate receptor 4 GRIA4 0.0042
664 Glutamate decarboxylase 2 GAD2 0.0042
3890 Glutamate decarboxylase 2 GAD2 0.0042
926 Metabotropic glutamate receptor 7 GRM7 0.0042
924 Glutamate receptor, ionotropic kainate 3 GRIK3 0.0042
915 Delta 1-pyrroline-5-carboxylate synthetase ALDH18A1 0.0042
927 Metabotropic glutamate receptor 8 GRM8 0.0042
925 Metabotropic glutamate receptor 4 GRM4 0.0042
4020 Glutamyl aminopeptidase ENPEP 0.0042
4018 Glutamate receptor delta-2 subunit GRID2 0.0042
4027 Glutamate receptor delta-1 subunit GRID1 0.0042
4017 5-oxoprolinase OPLAH 0.0042
917 Glutaminase kidney isoform, mitochondrial GLS 0.0036
355 GMP synthase [glutamine-hydrolyzing] GMPS 0.0036
4353 GMP synthase [glutamine-hydrolyzing] guaA 0.0036
3991 Glutamine-dependent NAD(+) synthetase NADSYN1 0.0036
3984 Probable glutamyl-tRNA(Gln) amidotransferase subunit B, mitochondrial PET112L 0.0036
5 Glutaminase liver isoform, mitochondrial GLS2 0.0036
665 Phosphoserine aminotransferase PSAT1 0.0036
4652 Phosphoserine aminotransferase serC 0.0036
668 Glutamate--cysteine ligase regulatory subunit GCLM 0.0036
801 Kynurenine/alpha-aminoadipate aminotransferase mitochondrial AADAT 0.0036
3982 Phosphoribosylformylglycinamidine synthase PFAS 0.0036
5261 Phosphoribosylformylglycinamidine synthase purL 0.0036
3895 Kynurenine--oxoglutarate transaminase 3 CCBL2 0.0036
420 Glutamate decarboxylase 1 GAD1 0.0036
3900 Glutamate decarboxylase 1 GAD1 0.0036
830 Glutamate dehydrogenase 2, mitochondrial GLUD2 0.0035
382 Glutamate receptor, ionotropic kainate 1 GRIK1 0.0035
625 Glutamate carboxypeptidase 2 FOLH1 0.0033
186 Glutamate--cysteine ligase catalytic subunit GCLC 0.0033
916 Metabotropic glutamate receptor 1 GRM1 0.0033
3877 Growth-inhibiting protein 18 GIG18 0.0033
1671 Excitatory amino acid transporter 3 SLC1A1 0.0033
923 Glutamate receptor 3 GRIA3 0.0032
763 Tyrosine aminotransferase TAT 0.0031
5493 Tyrosine aminotransferase Not Available 0.0031
773 Folylpolyglutamate synthase, mitochondrial FPGS 0.0031
914 Formimidoyltransferase-cyclodeaminase FTCD 0.0031
735 Alanine aminotransferase 1 GPT 0.0031
3904 Alanine aminotransferase 2 GPT2 0.0031
426 Aspartate aminotransferase, mitochondrial GOT2 0.0031
439 Glutamate [NMDA] receptor subunit epsilon-4 GRIN2D 0.0031
505 Glutamate [NMDA] receptor subunit epsilon-3 GRIN2C 0.003
201 Glutamate dehydrogenase 1, mitochondrial GLUD1 0.003
83 Alpha-aminoadipic semialdehyde synthase, mitochondrial AASS 0.003
586 Aspartate aminotransferase, cytoplasmic GOT1 0.0029
242 Asparagine synthetase [glutamine-hydrolyzing] ASNS 0.0029
591 Glutamate [NMDA] receptor subunit 3B GRIN3B 0.0029
210 Bifunctional aminoacyl-tRNA synthetase [Includes: Glutamyl-tRNA synthetase EPRS 0.0029
464 Glutamate [NMDA] receptor subunit epsilon-2 GRIN2B 0.0028
705 Glutamate receptor 1 GRIA1 0.0028
574 Branched-chain-amino-acid aminotransferase, cytosolic BCAT1 0.0027
795 Branched-chain-amino-acid aminotransferase, mitochondrial BCAT2 0.0027
33 Cystine/glutamate transporter SLC7A11 0.0027
837 Glutamate [NMDA] receptor subunit epsilon-1 GRIN2A 0.0027
401 Glutamate [NMDA] receptor subunit zeta-1 GRIN1 0.0027
3426 Glutamine synthetase glnA 0.0027
3987 Glutamine synthetase GLUL 0.0027
280 4-aminobutyrate aminotransferase, mitochondrial ABAT 0.0026
706 Glutamate [NMDA] receptor subunit 3A GRIN3A 0.0022
918 Glutamate receptor, ionotropic kainate 2 GRIK2 0.0022
738 Monocarboxylate transporter 1 SLC16A1 0.0021
6151 Monocarboxylate transporter 10 SLC16A10 0.002
921 Glutamate receptor 2 GRIA2 0.0019
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