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PubMed2005

Allergic contact dermatitis from cyanamide.

Cyanamide (carbimide or calcium carbimide) has been used to treat chronic alcoholism for more than 45 years. The skin reactions provoked by this medication are very rare and are generally associated with systemic reactions after ingestion of the product. However, allergic contact dermatitis has also been detected on persons who prepare cyanamide for administration to patients. We present a case of work-related allergic contact dermatitis from cyanamide that was confirmed by patch testing.

Adult↗
PubMedDate not supplied

[Free amino acids of the liver and the characteristics of the amino acid metabolism in the liver and brain after cyanamide administration to rats].

A single administration to rats of cyanamide (60 mg/kg, for 1 hour) was found to decrease the contents of cysteate, serine, glutamate, glycine, alanine, valine, methionine, isoleucine, tyrosine, ethanolamine, ornithine and histidine that may be considered as a manifestation on the drug hepatotoxicity. The activities of transaminases, glutamate dehydrogenase, pyruvate dehydrogenase remained unchanged. Cyanamide effects were considerably abolished by the supplementary ethanol administration (0.5 g/kg). Cyanamide failed to affect vitamin-dependent enzymes reflecting thiamine pyrophosphate, pyridoxal phosphate and flavine adenine dinucleotide status of the rat organism.

Amino Acids↗
PubMed1987

Cyanamide hepatotoxicity. Incidence and clinico-pathological features.

Ground-glass hepatocytes resembling those seen in HBsAg carriers on hematoxylin and eosin and on trichrome stained sections, but giving a negative reaction to orcein and a positive one to PAS, were found in liver biopsy specimens from nine asymptomatic former alcoholics who were on treatment with cyanamide, in one of four who had been treated with cyanamide several months before the liver biopsy procedure, in none of 15 treated with disulfiram, and in one of eight who had apparently not received aversive drugs. Portal and periportal inflammatory changes and fibrosis were more frequently observed in biopsy specimens containing PAS-positive ground-glass hepatocytes than in those without, but cirrhosis was found with a similar frequency. It is concluded that periportal PAS-positive ground-glass hepatocytes are a histological marker of cyanamide treatment.

Adult↗
PubMed1984

Cyanamide-induced liver cell injury. Experimental study in the rat.

Hepatocyte inclusion bodies similar to those described in alcoholics treated with cyanamide were reproduced in the rat. The characteristic inclusions were developed in animals receiving 8 or 16 mg/kg of body weight, whether they were prepared previously with ethanol intake or not. Inclusion bodies consist of round, well-demarcated cytoplasmic areas, which contain a large amount of glycogen disposed in beta-granules, lipid droplets, and secondary lysosomes. They appear at the 13th week of cyanamide treatment onward. Initially, hepatocytes bearing inclusion bodies are located predominantly at the periportal areas, but the lesion later progresses toward the center of the lobule. Prior to the inclusion body development, cyanamide induces another morphologic change in liver cells, consisting of cytoplasmic homogeneous areas, made up of glycogen disposed in alpha-granules and smooth endoplasmic reticulum tubules. This change is described for the first time in relation to this drug.

Alcohol Deterrents↗
PubMed1981

[Field study of workers with longterm exposure to calcium cyanamide (author's transl)].

"Kalkstickstoff" (calcium cyanamide) is extensively used as a fertilizer and a herbicide and also as a chemical intermediate. Its main compounds are calcium cyanamide (CaCN2) (60%) and calcium oxide (15%). In earlier times cauterized damages of the skin and the mucous membranes caused by the content of calcium oxide were common. A certain effect of CaCN2 is the reaction of intolerance after alcohol intake, which expresses as a so-called burning, a flush with redness and feeling of heat of the head, the neck and the upper part of the body often combined with tachycardia and dyspnea. Further health impairments, sometimes with fatal end, were reported repeatedly in the older literature. Convincing evidences for the causal connections between the exposure to CaCN2 and these damages are missed. They exclusively concerned farmers but not workers in the production of CaCN2. Except of the damages of the skin also diseases of the respiratory and gastrointestinal tract, the kidneys, the nervous and circulatory system as well as favoring of infectious complications and goitrogenic effects are in discussion. Furthermore it was suggested that CaCN2 causes a lack of reduced glutathione in the organism. On the occasion of establishing a preliminary MAC-value for CaCN2 in the F.R.G. an occupationally medical field study was performed on 65 workers of a calcium cyanamide factory with long-term exposure to CaCN2. The maximal CaCN2 concentration measured at the working places was 8.3 mg/m3. No signs of diseases or health impairments, which are possibly caused by CaCN2, were found with the medical examination in the above mentioned organs and organ systems. There also was no decrease of the glutathione content of the total blood detectable. With an alcohol load of 22 voluntary workers 1 till 7 hours after the working shift in 6 cases modest and in 7 cases weak flush reactions were observed. As result of the study an elevation of the MAC-value from 1 to at least 2.5 mg/m3 is proposed.

Adult↗
PubMed1997

A fatal case of drinking and cyanamide intake.

A 34-year-old housewife with alcohol dependence vomited severely, lost consciousness, and died after she took more than 20 ml of 1% calcium cyanamide, and alcoholic beverage containing about 129 g of ethyl alcohol. An autopsy was performed around 16 h after death. The body weighed 55.5 kg, and moderate lung edema was found. Ethanol concentrations were 4.24 mg/g in the left heart blood, 4.39 mg/g in the right heart blood, and 21.55 mg/g in the stomach contents. Cyanamide concentrations were 0.63 microgram/g in the left heart blood, 0.20 microgram/g in the right heart blood, and 0.22 microgram/g in the stomach contents. The cause of death was determined to be acute ethanol intoxication with alcohol-cyanamide reaction.

Adult↗
PubMed1980

Antimicrobial activity of N-substituted N-(triphenylstannyl)cyanamides and triethylammonium (organocyanoamino)chlorotriphenylstannates.

N-Substituted N-(triphenylstannyl)cyanamides were studied and found to be better antifungal agents than the previously tested N-substituted N'-cyano-S-(triphenylstannyl)isothioureas and N-substituted N'-cyano-O-(triphenylstannyl)isoureas. They were similar in activity to the previously tested ethyl N-aryl-S-(triphenylstannyl)-isothiocarbamates. The antifungal activity of triethylammonium (organocyanoamino)chlorotriphenylstannates, which are the triethylammonium chloride complexes of N-substituted N-(triphenylstannyl)-cyanamides, was similar to or better than that of the N-substituted N-(triphenylstannyl)cyanamides. Triethylammonium (acetylcyanoamino)chlorotriphenylstannate and triethylammonium dichlorotriphenylstannate were highly inhibitory toward Gram-positive bacteria.

Anti-Bacterial Agents↗
PubMed1979

Prebiotic nucleotide oligomerization in a fluctuating environment: effects of kaolinite and cyanamide.

The day kaolinite was tested for its ability to promote nucleotide oligomerization in model prebiotic systems. Heterogeneous mixtures of clay, water and nucleotide were repeatedly evaporated to dryness at 60 degrees C and redissolved in water in cyclic fashion in the presence or absence of cyanamide and/or ammonium chloride. With or without cycling, kaolinite alone did not promote the oligomerization of nucleotides at detectable levels. Cycling of clay in combination with cyanamide, however, promoted high levels of condensation to a mixture of oligonucleotides and dinucleotide pyrophosphate without requiring ammonium chloride. Although cycling with clay favored synthesis of dinucleotide pyrophosphate, cycling without clay enhanced formation of oligonucleotides. These results support the hypothesis that the presence of clays in fluctuating environments would have influenced the -ourse of prebiotic condensation reactions.

Alkaline Phosphatase↗
PubMed1990

Central action of an inhibitor of brain dopa-decarboxylase, NSD-1015, on cyanamide-induced alcohol drinking in rats.

A cannula for repeated intracerebroventricular (ICV) infusion was implanted stereotaxically in 16 male Sprague-Dawley rats. Subsequently, an alcohol preference test was given to each animal to establish its preferred concentration in the presence of water. After the alcohol solution was removed, 15 mg/kg cyanamide was injected subcutaneously for 4 days to maximize volitional intake of the single preferred solution of alcohol, which ranged from 7-15% in these animals. The L-aromatic amino acid decarboxylase inhibitor, NSD-1015 (3-hydroxybenzylhydrazine dihydrochloride) was then given ICV twice daily in a volume of 5.0 microliters in the following doses: 0.005, 0.01, 0.1 and 1.0 micrograms. NSD-1015 in all doses attenuated the g/kg alcohol intake of the rats; however, this decline was significant only at the lowest dose, which was pharmacologically specific, since neither food nor water intakes were altered by the treatment. Following the ICV infusions of NSD-1015, alcohol drinking returned essentially to postcyanamide levels. Further, during the interval of administration of NSD-1015, the cyanamide-induced decline in food consumption was reversed. These observations are in agreement with previous findings obtained under similar experimental conditions with the L-aromatic amino acid decarboxylase inhibitor, benserazide (Ro4-4602). They suggest that central decarboxylation or other effects of this drug on limbic system structures involved in the intake of alcohol could comprise a part of the mechanism underlying the induction of drinking. Further support is also provided for the involvement of brain dopamine and/or serotonin in the specific pattern of alcohol consumption in the rat.

Alcohol Drinking↗
PubMed2005

Novel and potent cyclic cyanamide-based cathepsin K inhibitors.

Starting from a PDE IV inhibitor hit derived from high throughput screening of the compound collection, a key pyrrolidine cyanamide pharmacophore was identified. Modifications of the pyrrolidine ring produced enhancements in cathepsin K inhibition. An X-ray co-crystal structure of a cyanamide with cathepsin K confirmed the mode of inhibition.

Animals↗
PubMed2004

Experimental study of water-ice catalyzed thermal isomerization of cyanamide into carbodiimide: implication for prebiotic chemistry.

Cyanamide (NH2CN) is a molecule of interstellar interest which can be implied in prebiotic chemistry. We showed, by FTIR spectroscopy, that cyanamide can be isomerized in carbodiimide (HNCNH), another interstellar relevant molecule, by a reaction involving the amorphous water-ice surface as catalyst. This isomerization occurs at low temperature (T < 100 K) which agrees quite well with that expected in the interstellar clouds composed of dust grains in which water is the most predominant constituent.

Carbodiimides↗
PubMed1987

A two-generation reproduction-fertility study of cyanamide in the rat.

A two-generation reproduction-fertility study of cyanamide in the rat has been carried out. After oral administration of 2, 7 and 25 mg/kg/day of the drug, relevant changes have been noted at the highest dose level. Decrease in dam weight gain, in number of corpora lutea, in number of implantations and in number of neonates have been observed in rats of the Fo generation after treatment with 25 mg/kg/day. This group showed a reduced fertility rate and decreases in the weight of several reproductive organs male rats. In contrast to the findings noted in the Fo generation, changes related to cyanamide treatment have not been observed in the F1 generation. Histopathology of these organs has disclosed a low incidence of bilateral testicular atrophy. Decreased fertility rate due to non-specific toxicity associated with a diminished food intake cannot be discarded.

Animals↗
PubMed1988

Effects of disulfiram, cyanamide and 1-aminocyclopropanol on the aldehyde dehydrogenase activity in human erythrocytes and leukocytes.

The effects of the aldehyde dehydrogenase (ALDH; EC 1.2.1.3) inhibitors disulfiram, cyanamide and 1-aminocyclopropanol (ACP) on the ALDH activities in human erythrocytes and leukocytes were studied. Assays were performed by incubating intact or sonicated blood cells in the presence of different concentrations of the inhibitors, using 3,4-dihydroxyphenylacetaldehyde, the aldehyde derived from dopamine oxidation, as the substrate. The amount of acid metabolite formed was measured using high-performance liquid chromatography with electrochemical detection. The erythrocyte ALDH was extremely sensitive to disulfiram, and only about 0.5 microM was needed to cause a 50% inhibition of the activity. The leukocyte activity was less sensitive, and showed a similar degree of inhibition at an 100-fold higher concentration of disulfiram. Cyanamide and ACP were both potent inactivators of the leukocyte ALDH activity, giving a 50% inhibition at concentrations of 10 and 50 microM, respectively, whereas the erythrocyte activity was much less affected. Diethyldithiocarbamate, the reduced metabolite of disulfiram, and coprine, from which ACP is derived, were much less effective inhibitors of the erythrocyte and leukocyte ALDH activities than were disulfiram and ACP.

Aldehyde Dehydrogenase↗
PubMed1992

Regression mechanism of cyanamide-induced inclusion bodies in the rat: a useful experimental pattern to study the beta-glycogen metabolization of hepatocytes.

Cyanamide, a drug used in alcohol aversion therapy, induces a distinctive liver cell lesion, both in human beings and rats. The lesion consists of cytoplasmic inclusion bodies which give a ground-glass appearance to the hepatocytes. In human beings the inclusion bodies do not persist but disappear some time after withdrawal of the drug. In order to confirm their disappearance and determine how they regress rats were treated with cyanamide (32 mg/kg) for 6 months before partial lobectomy. At this time, inclusion bodies were observed. After a period without further treatment (5-19 weeks) the animals were killed and a marked decrease in the number of inclusion bodies was observed, paralleling the period of time without treatment. Inclusion bodies regress as a result of glycogen removal by enzymatic activity of the smooth endoplasmic reticulum which then undergoes hyperplasia, plus a process of autophagocytosis and necrosis of inclusion-body-bearing hepatocytes which are then phagocytosed by macrophages.

Animals↗
PubMed1989

[Hepatotoxicity induced by cyanamide. A review of the anatomicopathological changes apropos a case].

A case of toxic liver disease induced by cyanamide in a patient in treatment with this drug during 18 months, is presented. We reviewed the different liver cell alterations produced by a long-term treatment with cyanamide, which produces fibrosis and portal inflammation, as well as polished cells with different characteristic features. These alterations forced the establishing of close controls of patients in treatment with this type of anti-alcoholism drug, as well as the reduction of the duration of therapy, this questioning the efficacy of the treatment of chronic alcoholism with this aversive drug.

Adult↗
PubMed1980

Effects of cyanamide and clofibrate on the enzymes of ethanol oxydation and on ethanol consumption in the rat.

The action of cyanamide and of clofibrate was studied on the voluntary drinking behaviour of alcohol intoxicated animals and also on the enzymes of ethyl oxydation. Both substances reduce alcohol consumption by about 35% and cause metabolic modifications: inhibition of aldehyde dehydrogenase and of catalase by cyanamide; activation of alcohol- and aldehyde-dehydrogenases by clofibrate. These effects are constantly found in most of the tissues of the rat. The results are discussed bearing in mind the relationships between alcohol metabolism, acetaldehyde metabolism, the toxicity of alcohol and the drinking behaviour.

Alcohol Drinking↗
PubMed1982

Ethanol as a discriminative stimulus: effects of cyanamide, acetaldehyde and chlormethiazole.

Two groups of gerbils were trained to discriminate between either 2 g/kg of ethanol (ETOH) and saline or 2 g/kg of ETOH and 1 g/kg of ETOH. Acetaldehyde and a combination of cyanamide, an aldehyde dehydrogenase inhibitor, plus ETOH were tested to determine if augmented levels of acetaldehyde would enhance ETOH-like responses. The CNS depressant drug chlormethiazole (CMZ) was also tested, separately and in combination with ETOH. The effects of ETOH and acetaldehyde were also tested in an open-field (O--F). Some effect of acetaldehyde (ED50 = 160 mg/kg) was observed in the group trained to discriminate between saline and 2 g/kg of ETOH (ED50 = 800 mg/kg) but not in the group trained to discriminate between 1 and 2 g/kg ETOH. Cyanamide (50 mg/kg) given before 1 g/kg of ETOH did not markedly change the amount of ETOH (2 g/kg) appropriate responses as compared to the saline control. The percentage of ETOH (2 g/kg) appropriate choices increased after testing combinations of CMZ and ETOH as compared to testing either drug separately. ETOH stimulated ambulation (horizontal locomotor activity), whereas acetaldehyde resulted in a dose related decrease of all the behaviour patterns recorded in the O--F test. The major conclusions from these studies are that the behavioural pharmacology of acetaldehyde differs from that of ETOH, that acetaldehyde plays only a limited role in the discriminative stimulus effects of ethanol in gerbils, and that the stimulus effects of ETOH and CMZ are additive.

Acetaldehyde↗