Absorption, Distribution and Excretion
Slowly absorbed from the gastrointestinal tract. Duration of action is proportional to the drug's half-life (T1/2) in plasma. A higher initial dose (loading dose) results in a shorter time to achieve the desired therapeutic effect… /Oral Anticoagulants/ Their onset and duration of action are shorter than dicumarol and warfarin. Therapeutic prothrombin time is achieved within 24 to 48 hours. After maintenance therapy is discontinued, prothrombin time returns to normal within 1 to 4 days. Good absorption via the gastrointestinal tract… Prothrombin time prolongation peaks at 18-48 hours and lasts for 1-4 days… Circulating drugs are almost completely bound to plasma proteins. Red blood cell uptake varies… Distributed to the liver, lungs, spleen… Kidneys (human, oral)

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Metabolism/Metabolites Hepatic metabolism. Hepatic metabolism.
Half-life: 5-10 hours

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Biological half-life
5-10 hours

Toxicity Summary
Phenindendrone inhibits vitamin K reductase, leading to depletion of reduced vitamin K (vitamin KH2). Since vitamin K is a cofactor for the carboxylation of N-terminal glutamate residues in vitamin K-dependent proteins, it restricts the γ-carboxylation and subsequent activation of vitamin K-dependent clotting proteins. The synthesis of vitamin K-dependent clotting factors II, VII, IX, and X, as well as anticoagulants C and S, is inhibited. Inhibition of three of the four vitamin K-dependent clotting factors (factors II, VII, and X) results in decreased prothrombin levels and reduced binding of generated thrombin to fibrin. This reduces the thrombotic tendency of thrombi. (A308) Protein Binding 88% Toxicity Data
Oral administration, mice: LD50 = 175 mg/kg; Oral administration, rats: LD50 = 163 mg/kg.

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Interactions
Studies have found that haloperidol can shorten the prothrombin time normally produced by phenylindanedione.
The activity of phenylindanedione (an anticoagulant) can also be enhanced by C-17-alkylated androgens.
Serious bleeding has been reported when corticotropin and adrenocorticotropic hormones are used in combination with oral anticoagulants.
Interactions between antipyrine (in vivo) and sulfinpyrazone (in vitro) and warfarin have been reported and should be used with caution in patients. Currently receiving anticoagulant therapy. /Anticoagulants/
For more complete data on interactions of phenylindanedione (out of 12), please visit the HSDB records page.

Phenindione is a β-diketone and an aromatic ketone. It has anticoagulant properties. It is derived from the hydrogenated form of indan. Phenindione is an indanedione compound that was formerly used as an anticoagulant. Its effects are similar to warfarin, but it is rarely used now due to its higher incidence of serious adverse reactions. (Excerpt from Martindale Pharmacopoeia, 30th edition, p. 234) Phenindione is only present in individuals who have used or taken this drug. It is an indanedione compound that was formerly used as an anticoagulant. Its effects are similar to warfarin, but it is rarely used now due to its higher incidence of serious adverse reactions. (Excerpt from Martindale Pharmacopoeia, 30th edition, p. 234) Phenindione inhibits vitamin K reductase, leading to the depletion of reduced vitamin K (vitamin KH2). Because vitamin K is a cofactor for the carboxylation of the N-terminal glutamate residues of vitamin K-dependent proteins, it restricts the γ-carboxylation of vitamin K-dependent clotting proteins and their subsequent activation. The synthesis of vitamin K-dependent clotting factors II, VII, IX, and X, as well as anticoagulants C and S, is inhibited. Inhibition of three of the four vitamin K-dependent clotting factors (factors II, VII, and X) leads to decreased prothrombin levels and reduced thrombin production and fibrin binding. This reduces the thrombogenicity of thrombi. Indenedione is an indenedione compound formerly used as an anticoagulant. Its effects are similar to warfarin, but it is now rarely used due to its high incidence of serious adverse reactions. (Excerpt from Martindale Pharmacopoeia, 30th edition, p. 234)

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Indications
For the treatment of pulmonary embolism, cardiomyopathy, atrial fibrillation and flutter, cerebral embolism, wall thrombosis, and thrombotic tendency. Also used for anticoagulation prophylaxis.

Mechanism of Action
Phenindendrone inhibits vitamin K reductase, leading to the depletion of reduced vitamin K (vitamin KH2). Since vitamin K is a cofactor for the carboxylation of N-terminal glutamate residues in vitamin K-dependent proteins, it restricts the γ-carboxylation and subsequent activation of vitamin K-dependent clotting proteins. The synthesis of vitamin K-dependent clotting factors II, VII, IX, and X, as well as anticoagulants C and S, is inhibited. Reduced activity of three of the four vitamin K-dependent clotting factors (factors II, VII, and X) leads to decreased prothrombin levels, thereby reducing thrombin production and fibrin binding. This reduces the thrombogenicity of thrombi.
…Anticoagulants inhibit the action of vitamin K by blocking the production of factors II, VII, IX, and X in the liver. …Coumarin anticoagulants may also affect the transport of vitamin K to its site of action. /Anticoagulants/
Oral anticoagulants have only one major pharmacological action—inhibiting blood clotting mechanisms by interfering with the liver's synthesis of vitamin K-dependent clotting factors. ...In the body, its initial effects only appear after the latency period... /Oral Anticoagulants/

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Therapeutic Uses
Anticoagulants
...Oral anticoagulants can be used to prevent and treat a variety of thromboembolic diseases. /Oral Anticoagulants/
...Indications for anticoagulants...1) Myocardial infarction, 2) Rheumatic heart disease, 3) Cerebrovascular disease, 4) Venous thrombosis and pulmonary embolism, and 5) Disseminated intravascular coagulation. /Anticoagulants/

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Drug Warnings
Long-term treatment is not recommended for patients with chronic alcoholism, patients who may require intensive salicylates, or patients with malignant hypertension and active pulmonary tuberculosis.Oral anticoagulant treatment during pregnancy carries a significant risk of bleeding to the fetus. /Oral Anticoagulants/
...Contraindicated in patients with bleeding tendencies, blood disorders, gastrointestinal ulcerative lesions, diverticulitis, colitis, subacute bacterial endocarditis, threatened abortion, recent brain or spinal surgery, regional anesthesia or lumbar block anesthesia, vitamin K deficiency, or liver or kidney disease. Changes in vitamin K availability can affect the therapeutic response to oral anticoagulants. ...Neonatals are particularly sensitive to oral anticoagulants. ...Renal insufficiency, fever, and scurvy can enhance or prolong the efficacy of oral anticoagulants. Oral Anticoagulants
It must be emphasized that treatment regimens must be highly individualized for each patient. Patients receiving anticoagulation therapy must have their prothrombin time monitored regularly and be closely monitored for bleeding tendencies. /Anticoagulants/
For more complete data on drug warnings for phenylindanedione (15 in total), please visit the HSDB record page.

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Pharmacodynamics
Phenindanone thins the blood by antagonizing vitamin K, which is essential for the liver to produce clotting factors. Anticoagulants like phenylindanone have no direct effect on existing thrombi and cannot reverse ischemic tissue damage (damage caused by insufficient blood supply to an organ or part of the body). However, once a thrombus has formed, the goal of anticoagulation therapy is to prevent the thrombus from expanding further and to prevent secondary thromboembolic complications that can have serious or even fatal consequences. Phenindanone's effects are similar to warfarin, but it is rarely used now due to its higher incidence of serious adverse reactions.

C15H10O2

222.24

222.068

83-12-5

Phenindione-d5;70711-53-4

4760

LEAFLETS FROM ALCOHOL
CREAMY WHITE TO PALE YELLOW CRYSTALS OR CRYSTALLINE POWDER

1.343g/cm3

243.3 °C (0.3 mmHg)

144-148 °C(lit.)

208 °C

1.703

2.849

0

2

1

17

304

0

O=C1C(C2C=CC=CC=2)C(=O)C2C1=CC=CC=2

NFBAXHOPROOJAW-UHFFFAOYSA-N

InChI=1S/C15H10O2/c16-14-11-8-4-5-9-12(11)15(17)13(14)10-6-2-1-3-7-10/h1-9,13H

2-phenylindene-1,3-dione

Phenylindanedione; 2-Phenyl-1,3-indandione; Phenindione

2934.99.9001

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

DMSO : ≥ 100 mg/mL (~449.96 mM)
H2O : < 0.1 mg/mL

Solubility in Formulation 1: ≥ 2.5 mg/mL (11.25 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

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Solubility in Formulation 2: ≥ 2.5 mg/mL (11.25 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.

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 (Please use freshly prepared in vivo formulations for optimal results.)