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PubMed1982

Reverse phase high performance liquid chromatographic determination of phenprocoumon in tablets.

A high performance liquid chromatographic procedure has been developed for the assay of phenprocoumon in tablets. In comparison to the present official USP assay procedure, it is equivalent in precision and accuracy and is faster and more specific. A mobile phase consisting of a 1% solution of acetic acid in acetonitrile-water (4 + 3) separates phenprocoumon from warfarin internal standard on a 6 micrometer octadecylsilane (ODS) column with UV detection at 311 nm. The method enables the concurrent determination of phenprocoumon and possible contaminants such as salicylic acid.

4-Hydroxycoumarins↗
PubMed1995

[Factitious disease caused by secret administration of the oral anticoagulant phenprocoumon: study of 16 personal cases].

BACKGROUND: It is frequently difficult to disclose covert ingestion of cumarins being the underlying cause of a bleeding disorder. PATIENTS AND METHODS: We report on 16 cases (15 patients) of phenprocoumon (Marcumar) abuse. All patients (9 females, 6 males) were admitted to the hospital because of bleeding and/or prolonged thromboplastin times. Analysis of phenprocoumon in the blood was performed by HPLC. RESULTS AND CONCLUSIONS: The clinical presentation of the bleeding was highly variable. Thromboplastin times ranged from < 5 to 58%. With the exception of two patients with hepatic dysfunctions factor V activity was normal. All but one patient denied the ingestion of Marcumar. One patient died from hemorrhage. Two types of patients emerge from our series: Type I is the young nurse (8 cases), type II the usually male patient formerly treated with phenprocoumon (5 cases). Type I patients had long medical histories and showed autoaggressive behavior including the artificial manipulation of disorders other than hemorrhage. Thromboplastin times however were within or close to the therapeutic range (10 to 25%). Type II patients did not simulate other diseases in addition to hemorrhage. Thromboplastin times were longer than in type I patients. In all instances discrimination between non suicidal and suicidal behaviour was difficult. Psychiatric consultance is indicated.

Administration, Oral↗
PubMedDate not supplied

Phenprocoumon therapy during pregnancy: case report and comparison of the teratogenic risk of different coumarin derivatives.

The case report is about an infant suffering from coumarin embryopathy and coumarin syndrome after its mother underwent phenprocoumon treatment (Marcumar, Falithrom) during pregnancy (until 26th week of gestation). Interestingly, a hearing disorder was diagnosed, which had never been described in context with this substance. The coumarin derivatives warfarin, acenocoumarol and phenoprocoumon were compared with regards to spontaneous abortion rate, perinatal mortality and teratogenic risk. Eye anomalies or malformations seem to appear only under warfarin treatment, whereas CNS-malformations are more frequent under phenprocoumon. As a consequence, phenprocoumon treatment of fertile women seems rather doubtful. Upon discovery of a pregnancy under coumarin treatment, vitamin K should immediately be substituted in order to minimize the risk of anomalies and malformation.

Abnormalities, Drug-Induced↗
PubMed1977

[Studies on the interactions of phenprocoumon with chlordiazepoxide in rats (author's transl)].

The influence of Chlordiazepoxide (Librium) on the anticoagulating activity of Phenprocoumon (Marcumar) was investigated in rats. It was found that this psychotropic drug influences neither the anticoagulating activity nor the normal prothrombin-time when it is applied alone or together with Phenprocoumon. However, the prothrombin-time is shortened when Chlordiazepoxide is withdrawn and the feeding of Phenprocoumon is continued.

4-Hydroxycoumarins↗
PubMed1976

Determination of phenprocoumon, an anticoagulant, in human plasma.

Phenprocoumon is extracted from acidified plasma, the organic phase evaporated, and part of the residue, in ethanol, is quantitatively applied to a thin-layer plate. After separation, the quantity of phenprocoumon is assayed by fluorescence densitometry in situ. Results are reproducible to about 2.5%. The lower limit of detection is 0.1 mg/liter, which makes the method fully applicable to human plasma, because therapeutic concentrations range from 1 to 3 mg/liter. Seven determinations can be made within 3 h. For toxicological purposes, a qualitative analysis can be done in a shorter time, because the phenprocoumon spots are visible under ultraviolet light at 254 nm.

4-Hydroxycoumarins↗
PubMed2002

Fatal drug interaction between cholestyramine and phenprocoumon.

We describe a patient with a prosthetic aortic valve who developed fatal valve thrombosis due to an interaction between phenprocoumon and cholestyramine. The general practitioner who had prescribed cholestyramine was aware of a potential interaction between these two drugs and the patient ingested cholestyramine exactly according to the rules of the manufacturer (>1 h before phenprocoumon). However, due to enterohepatic cycling and the long half-life of phenprocoumon, an interaction between these two drugs could not be avoided. We therefore recommend that cholestyramine not be administered to patients treated with drugs undergoing enterohepatic cycling, such as oral anticoagulants.

Journal Article↗
PubMed1985

A stable isotope assay for phenprocoumon and its metabolites.

A gas chromatographic/mass spectrometric assay for quantifying phenprocoumon and its 4'-, 6-, 7- and 8-hydroxy metabolites in microsomal preparations is described. This assay which uses deuterium-labeled analogs of the phenprocoumon metabolites as internal standards has a lower limit of quantitation of 20 ng ml-1. Diazomethane is used to derivatize both metabolites and parent compound yielding along with the expected 4-methoxy derivative a minor amount of the 2-methoxychromone. Resolution of the methylated metabolites is accomplished by capillary gas chromatography.

4-Hydroxycoumarins↗
PubMed1992

Stereoselective effect of phenprocoumon enantiomers on the binding of benzodiazepines to human serum albumin.

The effect of phenprocoumon enantiomers on the stereoselective binding of 3-substituted 1,4-benzodiazepines to human serum albumin (HSA) was studied by chromatography on HSA-Sepharose column. (S)-Phenprocoumon exerts stereoselective allosteric interaction on the binding of benzodiazepines. The structural requirements of enhanced stereoselectivities are similar to those found previously with (S)-warfarin.

Benzodiazepines↗
PubMed1978

[The influence of diazepam (valium) on the effect of phenprocoumon (marcumar) (author's transl)].

In 10 patients who were treated with phenprocoumon (Marcumar) for thrombembolic diseases, we examined the influence of the combined therapy with diacepam (Valium) on the effect of the anticoagulant. After stopping the therapy with diacepam we saw a significant increase of the prothrombinetime (Quick) beyond the therapeutic level of 25%. By increasing the dosis of phenprocoumon the therapeutic level was achieved again not until after 8 days. The dosis needed for maintaining this level was on the average 32% higher than during the time of the therapy in which diacepam was used. Because of the increased thrombembolic risk, when going beyond the therapeutic level of the prothrombinetime, this interaction is of clinical importance.

4-Hydroxycoumarins↗
PubMed1998

[Successful therapy of phenprocoumon poisoning with plasmapheresis].

UNLABELLED: A case report demonstrates a possibility of successful treatment in a patient with high-dosage phenprocoumon intoxication. CONCLUSION: The use of plasmapheresis is an appropriate method to treat phenprocoumon-intoxicated patients by exchange of endogenous with supplied fresh frozen plasma.

Anticoagulants↗
PubMed1977

A gas chromatographic method for the estimation of phenprocoumon, 3-(1-phenyl-propyl)-4-hydroxycoumarin (Marcoumar, Liquamar), in human serum or plasma.

A rapid and reliable gas-chromatographic method is described for the estimation of phenprocoumon from human serum or plasma. No interference was found from other usual oral anticoagulant drugs. The method can be used for therapeutic and toxic levels. The appearance of two volatile derivatives of phenprocoumon (in constant ratio) is discussed.

4-Hydroxycoumarins↗
PubMed1996

General pharmacology of meloxicam--Part II: Effects on blood pressure, blood flow, heart rate, ECG, respiratory minute volume and interactions with paracetamol, pirenzepine, chlorthalidone, phenprocoumon and tolbutamide.

The pharmacodynamic properties of meloxicam, a new nonsteroidal antiinflammatory drug (NSAID), that go beyond those typical of an NSAID were examined. The extent to which meloxican shows NSAID-like interactions with paracetamol, pirenzepine, chlorthalidone, phenprocoumon and tolbutamide was also investigated. In the dose range studied, meloxicam had no influence on the blood pressure of the unanaesthetized rat, blood flow, heart rate, ECG and respiratory minute volume of the anaesthetized cat or on the blood pressure, heart rate and respiratory minute volume of the anaesthetized dog. The acute toxicity level of meloxicam after oral and parenteral administration to the rat and mouse proved considerably lower than that of indomethacin. Meloxicam showed excellent tissue tolerability following parenteral administration. The effects against inflammatory pain and acute antiexudative effects of meloxicam were enhanced by simultaneous low doses of paracetamol. Pirenzepine showed an antagonistic effect on the ulcerogenicity of meloxicam in the rat stomach. The diuretic effect of chlorthalidone in the rat was not influenced by high doses of meloxicam. The effect of phenprocoumon in the rat was enhanced by high doses of meloxicam. However, the hypoglycaemic effect of tolbutamide in the rabbit was not influenced by meloxicam.

Acetaminophen↗
PubMed1985

Identification of phenprocoumon metabolites in human urine by high-performance liquid chromatography and gas chromatography-mass spectrometry.

The oral anticoagulant phenprocoumon is eliminated in urine mainly as the glucuronide conjugate to an extent of 20% of the dose. The urine from patients undergoing phenprocoumon therapy was investigated and the following metabolites were isolated and identified: 7-hydroxyphenprocoumon as the main component, and 4'-hydroxyphenprocoumon and 6-hydroxyphenprocoumon as conjugates. They were characterized by high-performance liquid chromatography and, after methylation, by gas chromatography-mass spectrometry.

4-Hydroxycoumarins↗
PubMed1998

Determination of phenprocoumon in plasma and urine using at-line solid-phase extraction-capillary electrophoresis.

The use of capillary electrophoresis (CE) for the analysis of biological samples is rather problematic because of the large number of interferences present in the matrix. One of the possibilities to solve such problems is to couple solid-phase extraction (SPE) at-line with CE, a technique developed in our laboratory. In this study at-line SPE-CE is performed for the determination of the anticoagulant phenprocoumon in biological fluids. Plasma samples are injected after the addition of 1 vol.% of formic acid to release the drug from binding proteins, while urine samples can be directly injected. The procedure is linear between 0.2 and 30 microg ml(-1) with a correlation coefficient, r2, of 0.9996. The detection limit in plasma is 0.1 microg ml(-1), which is fully adequate in view of the concentrations, that have to be dealt with in practice. The phenprocoumon concentration in a plasma sample of a patient treated with the anticoagulant was 3.8 microg ml(-1).

Electrophoresis, Capillary↗
PubMed2003

Use of subcutaneous enoxaparin compared to intravenous heparin and oral phenprocoumon in the setting of cardioversion--the ACE study (Anticoagulation in Cardioversion using Enoxaparin).

The mode and duration of anticoagulation in the setting of cardioversion of atrial fibrillation-either with or without guidance by transesophageal echocardiography (TEE)-is still an unresolved issue. Oral anticoagulation with warfarin or phenprocoumon is frequently used but may be associated with an increased risk of bleeding complications or, conversely, episodes of undercoagulation. Moreover, it takes several days to reach full anticoagulation with oral compounds. This phase may be covered with intravenous heparin but this requires prolonged hospitalization. Low-molecular weight heparin is an attractive alternative as it not only provides a safe and predictable level of anticoagulation with few side effects but can also be administered safely on an outpatient basis. In addition, anticoagulation monitoring is usually unnecessary. The ACE study (Anticoagulation in Cardioversion using Enoxaparin) compared the safety and efficacy of subcutaneous enoxaparin with intravenous heparin/oral phenprocoumon before and after cardioversion (stratified to TEE guidance or no TEE guidance). This article summarizes the study rationale and design. The results will be published shortly.

Administration, Oral↗
PubMed1999

Course of the international Normalized Ratio in response to oral vitamin K1 in patients overanticoagulated with phenprocoumon.

Oral vitamin K1 is used for the treatment of excessive anticoagulation. Detailed information on changes in the International Normalized Ratio (INR) in response to vitamin K1 is not available. We therefore measured the INR for the first 7 d following the oral intake of 1-5 mg of vitamin K1 in 24 patients routinely treated with phenprocoumon who had an INR > or =6.0 at presentation. On the first 2 d after administration of vitamin K1, the mean INR decreased by 40% and 23% respectively. After day 2, the day-to-day proportional change in the mean INR depended on the dose of vitamin K1 and varied from a decrease of 12% to an increase of 21%. On day 7 the mean INR was higher than on day 2 in three out of five treatment groups. Between day 2 and day 7, in general, 32% of the patients had an INR value within the target zone, 25% had an INR value > or =6.0 and 8% had an INR value <2.0. These findings suggest that our routine treatment of overanticoagulation in patients on phenprocoumon should be intensified to improve its efficacy.

Administration, Oral↗
PubMed2004

Analysis of pooled plasma samples as a predictor for proving bioequivalence of drugs with a long elimination half-life. The example of phenprocoumon.

The results of pooled plasma analysis in a bioequivalence trial provide information comparable with that of the mean concentration vs. time curves for each formulation. Although it seems feasible that pool plasma analysis will have similar or even greater advantages in cases of bioequivalence trials with a parallel-group design, no such data has been published in the literature probably due to the limited number of such trials. The present study was designed with the aim to investigate the prediction value of pool plasma analysis in a bioequivalence trial with phenprocoumon (CAS 435-972). The study was performed as a monocentric, randomized, open clinical trial in two parallel groups of healthy male volunteers (31 per group), all of which received a single oral dose of 3 mg phenprocoumon. Serial blood samples were drawn for the pharmacokinetic analysis pre-dose, and 0.33, 0.67, 1, 1.5, 2, 2.5, 3, 3.5, 4, 6, 12, 24, 48, 96, 144, 192, and 240 h after drug administration. Pool plasma was prepared for each sampling point and each formulation. Drug concentrations were measured by means of an HPLC method. A comparison between the pool plasma results and the results of individual analysis revealed a very good correspondence regarding the parameters AUC, Cmax and t(max). The present trial demonstrates that the method of time-wise pooling provides reliable information not only in cross-over trials but also in trials with parallel groups of volunteers.

Adult↗
PubMed2004

[Acute liver failure caused by phenprocoumon -- three case reports].

We report on three women with phenprocoumon-induced liver failure. In all three, jaundice was the main symptom. Liver failure was manifest 6 months after initial exposure to phenprocoumon in two women and 18 months in the third. None received corticosteroids. The course was prolonged in each patient, but all three finally recovered. Liver failure associated with oral anticoagulation is rare. Most published reports describe only individual cases. Instances of fatal outcome and instances requiring liver transplantation for survival have been seen. Coumarin treatment should be considered as a possible etiology of acute liver failure, even if the drug has been administered for a longer period without any previous problems. While cross-reactions with other coumarin substances have been reported, if coumarin anticoagulation is absolutely required, use of a congener under close monitoring seems justifiable.

Aged↗