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At least 433 records · Page 24Linked to original sources
PubMed1998

Racemate and enantiomers of ketoprofen: phase diagram, thermodynamic studies, skin permeability, and use of chiral permeation enhancers.

The role of intrinsic and extrinsic factors on transport of a chiral drug through the skin was studied. Ketoprofen (KP) was chosen as a model chiral drug. A possible relationship between the melting characteristics and the flux values of S- and RS-KP was investigated. The potential use of chiral enhancers, menthol and linalool, was also investigated. Thermal analyses were carried out for individual enantiomers and the racemate of KP. The melting temperature of each enantiomer was 22 degreesC lower than that of the racemic compound. Peak temperatures from the melting endotherms were plotted as a function of enantiomeric composition to give the binary phase diagram. The phase diagram suggested the presence of a racemic compound, and it was verified by calculations of the liquidus curve in the dystectic region using reported methods. Powder X-ray diffraction studies also confirmed that the racemate of KP is a racemic compound. The permeability of individual enantiomers and the racemate of KP through mice skin was determined in vitro using side-by-side diffusion cells. Transfer of R- and S-KP from aqueous solutions of both the racemate and pure enantiomer showed no significant differences in the rates of permeation, indicating that the rate of transfer of KP across the mice skin from these solutions was independent of the stereochemistry of the drug. No evidence of racemization during the transfer process was observed. The permeation-enhancing ratio of linalool was higher, but not significant, than that of l-menthol. The predicted ratio of enantiomer to racemate flux through the skin by the MTMT concept (1. 97) is in close agreement with the experimentally determined ratio (1.79) across mouse skin.

Acyclic Monoterpenes↗
PubMed2005

PI(4,5)P2 regulates the activation and desensitization of TRPM8 channels through the TRP domain.

The subjective feeling of cold is mediated by the activation of TRPM8 channels in thermoreceptive neurons by cold or by cooling agents such as menthol. Here, we demonstrate a central role for phosphatidylinositol 4,5-bisphosphate (PI(4,5)P(2)) in the activation of recombinant TRPM8 channels by both cold and menthol. Moreover, we show that Ca(2+) influx through these channels activates a Ca(2+)-sensitive phospholipase C and that the subsequent depletion of PI(4,5)P(2) limits channel activity, serving as a unique mechanism for desensitization of TRPM8 channels. Finally, we find that mutation of conserved positive residues in the highly conserved proximal C-terminal TRP domain of TRPM8 and two other family members, TRPM5 and TRPV5, reduces the sensitivity of the channels for PI(4,5)P(2) and increases inhibition by PI(4,5)P(2) depletion. These data suggest that the TRP domain of these channels may serve as a PI(4,5)P(2)-interacting site and that regulation by PI(4,5)P(2) is a common feature of members of the TRP channel family.

Animals↗
PubMed2002

Specificity of cold thermotransduction is determined by differential ionic channel expression.

Sensations of cold are mediated by specific thermoreceptor nerve endings excited by low temperature and menthol. Here we identify a population of cold-sensitive cultured mouse trigeminal ganglion neurons with a unique set of biophysical properties. Their impulse activity during cooling and menthol application was similar to that of cold thermoreceptor fibers in vivo. We show that cooling closes a background K+ channel, causing depolarization and firing that is limited by the slower reduction of a cationic inward current (Ih). In cold-insensitive neurons, firing is prevented by a slow, transient, 4-AP-sensitive K+ current (IKD) that acts as an excitability brake. In addition, pharmacological blockade of IKD induced thermosensitivity in cold-insensitive neurons, a finding that may explain cold allodynia in neuropathic pain. These results suggest that cold sensitivity is not associated to a specific transduction molecule but instead results from a favorable blend of ionic channels expressed in a small subset of sensory neurons.

4-Aminopyridine↗
PubMed1985

A survey of neonatal jaundice in association with household drugs and chemicals in Nigeria.

A survey was conducted to determine the extent of exposure of women of child-bearing age and their families to household chemicals and medicaments, and the prevalence of neonatal jaundice in the exposed and unexposed families compared. Significant exposures to naphthalene, insecticides, mentholated balms, mentholated powders, and traditional herbs occurred in 45-87% of the families studied. The overall incidence of jaundice did not differ significantly in neonates from households with or without positive history of drugs/chemical exposures. Severe neonatal jaundice, as judged by the need for exchange blood transfusion or death of the infant, was however, significantly more frequent among neonates from families with positive history of naphthalene exposure than in those with negative history. Some household chemicals and medicaments may be important in the pathogenesis of neonatal jaundice in our environment, and health education aimed at eliminating exposure neonates and pregnant women to such agents is urgently necessary.

Female↗
PubMed2004

Cooling of the urinary bladder activates neurons in the dorsal horn of the spinal cord.

Although visceral innocuous cold receptors have been documented, the central termination of their afferents is unknown. We used menthol solution (0.6 mM) to obtain selective activation of cold receptors in the urinary bladder of rats. Innocuous cold stimulation induced Fos expression in a population of neurons in the superficial dorsal horn of L6-S1 segments of the spinal cord. Neurons in other regions of the spinal cord, e.g. the lumbar parasympathetic nucleus or the dorsal commissure region, were activated to a similar degree by menthol and control infusions, indicating a response to bladder filling. Our results are consistent with the proposal that subsets of modality-specific dorsal horn neurons convey specific information regarding the exteroceptive and interoceptive state of the animal.

Animals↗
PubMed2006

Antimicrobial activity of carvacrol related to its chemical structure.

AIMS: To investigate the relation between the chemical structure and the antimicrobial activity of carvacrol, eugenol, menthol and two synthesized carvacrol derivative compounds: carvacrol methyl ether and carvacryl acetate against bacteria, Escherichia coli, Pseudomonas fluorescens, Staphylococcus aureus, Lactobacillus plantarum, Bacillus subtilis, a yeast Saccharomyces cerevisiae and one fungi Botrytis cinerea. METHODS AND RESULTS: The antimicrobial activity was tested in liquid and vapour phases, by both broth liquid and microatmosphere methods, respectively. The same classification of the compound's antimicrobial efficiency was found with both methods. Eugenol and menthol exhibited a weaker antimicrobial activity than carvacrol, the most hydrophobic compound. Carvacryl acetate and carvacrol methyl ether were not efficient, indicating that the presence of a free hydroxyl group is essential for antimicrobial activity. CONCLUSIONS: The different extents of antimicrobial aroma compounds' efficiency showed that hydrophobicity is an important factor and the presence of a free hydroxyl group and a delocalized system allows proton exchange. SIGNIFICANCE AND IMPACT OF THE STUDY: This study has identified the importance of the hydrophobicity and the chemical structure of phenolic aroma compounds for antimicrobial activity and may contribute to a most rational use of these compounds as antimicrobial agent.

Anti-Infective Agents↗
PubMed2005

Mechanisms of antibacterial action of three monoterpenes.

In the present paper, we report the antimicrobial efficacy of three monoterpenes [linalyl acetate, (+)menthol, and thymol] against the gram-positive bacterium Staphylococcus aureus and the gram-negative bacterium Escherichia coli. For a better understanding of their mechanisms of action, the capability of these three monoterpenes to damage biomembranes was evaluated by monitoring the release, following exposure to the compounds under study, of the water-soluble fluorescent marker carboxyfluorescein from unilamellar vesicles with different lipidic compositions (phosphatidylcholine, phosphatidylcholine/phosphatidylserine [9:1], phosphatidylcholine/stearylamine [9:1], and phosphatidylglycerol/cardiolipin [9:1]). Furthermore, the interaction of the terpenes tested with dimyristoylphosphatidylcholine multilamellar vesicles as model membranes was monitored by means of differential scanning calorimetry. Finally, the results were related to the relative lipophilicity and water solubility of the compounds examined. Taken together, our findings lead us to speculate that the antimicrobial effect of (+)menthol, thymol, and linalyl acetate may result, at least partially, from a perturbation of the lipid fraction of microorganism plasma membrane, resulting in alterations of membrane permeability and in leakage of intracellular materials. Besides being related to physicochemical characteristics of the drugs (such as lipophilicity and water solubility), this effect seems to be dependent on lipid composition and net surface charge of microbial membranes. Furthermore, the drugs might cross the cell membranes, penetrating into the interior of the cell and interacting with intracellular sites critical for antibacterial activity.

Anti-Bacterial Agents↗
PubMed1998

Emotional responses evoked by dental odors: an evaluation from autonomic parameters.

Among the factors which could explain avoidance behavior toward dental care, the typical clinging odor of the dental office, due to eugenol, is investigated in this study. The hypothesis is supported by the well-known effects of odorants which may influence cognition, emotion, and behavior. The association between the odor of eugenol and dental fear and anxiety could be explained by the fact that eugenates (eugenol-containing cements) are often used in potentially painful restorative dentistry on vital teeth. The emotional impact of the odors of eugenol and two other dental products (menthol and methyl methacrylate) was evaluated on volunteer subjects through autonomic nervous system (ANS) analysis by recording the variations of six ANS parameters (two electrodermal, two thermovascular, and two cardiorespiratory) induced by the inhalation of the odorants. After the experiment, subjects were asked to fill out an 11-point hedonic scale to rate the pleasantness vs. unpleasantness for each odorant. Results were compared between two groups of subjects divided according to their own dental experience (fearful and non-fearful dental-care subjects). These showed that, in both groups, menthol was rated as pleasant and methyl methacrylate as very unpleasant, whereas eugenol was judged pleasant by non-fearful subjects but unpleasant by fearful subjects. Concerning autonomic analysis, only eugenol induced significantly different patterns of ANS responses between the two groups, with stronger variations for dentally fearful subjects, mainly observed through the electrodermal channel. These results suggest that eugenol can be responsible for different emotional states, depending on the unpleasantness of the subjects' dental experience. This seems to confirm the role of odors as elicitors of emotional memories and to support the possible influence of eugenol odor on the avoidance behavior of some subjects toward dental care.

Adult↗
PubMed1993

Effect of pretreatment of skin with cyclic monoterpenes on permeation of diclofenac in hairless rat.

The promoting effect of d-limonene and l-menthol on the percutaneous absorption of nonionized and ionized diclofenac (DF) was investigated employing a pretreatment method. After the pretreatment of hairless rat skin with an ethanol buffer solution containing terpenes, the permeation study was performed in vitro. The permeability coefficients of nonionized (Pn) and ionized diclofenac (Pi) were calculated under the assumption that the total flux was composed of individual fluxes of nonionized and ionized DF. In the case of pretreatment with d-limonene, both Pn and Pi values were increased dramatically. However, the promoting magnitude was not affected by an extension of the pretreatment period. In contrast, when the skin was pretreated with l-menthol, the Pn and Pi values increased gradually as the pretreatment period increased. Based on the measurement of the solubility of terpenes in the pretreatment solution, the difference in promoting efficiency could arise from the difference in thermodynamic activity of the terpenes.

Animals↗
PubMed2003

Effect of mixed micelle formulations including terpenes on the transdermal delivery of diclofenac.

The significant inhibitory action of diclofenac formulated in mixed micelles of lecithin with cholate or deoxycholate was observed on the rat hind paw edema induced by carrageenan. In the primary stage, mixed micelle formulation of deoxycholate was more effective compared with that of cholate. However, in the final term, the inhibitory action was similar in both formulations. In a previous study, the flux of diclofenac was greater in the mixed micelle formulation of deoxycholate compared with that of cholate. It was suggested that the permeation rate of diclofenac through skin was proportional to the pharmacological activity. The hind paw edema was quickly inhibited when cyclic monoterpene such as d-limonene or l-menthol was included in the formulations. All the micelle formulations significantly decreased the value of AUC estimated the hind paw thickness-time profile. This suggests that the micelle formulation of cholate in addition to deoxycholate showed significant anti-inflammatory activity to hind paw edema of rats. Incorporation of d-limonene or l-menthol was more effective on the decrease of AUC. A pharmacological study revealed that micelle formulations were able to reduce the skin irritation of chemicals.

Administration, Cutaneous↗
PubMed2006

Formulation and evaluation of ethylene-vinyl acetate copolymer matrix patches containing formoterol fumarate.

The skin permeability and stability of formoterol fumarate (FF) in matrix patches containing l-menthol as an enhancer and N-methyl-2-pyrrolidone (NMP) as the solvent were investigated. Using a total of 28 matrix patches having a similar composition, containing ethylene-vinyl acetate (EVA) as the forming polymer and hydrogenated rosin glycerol ester (Ester Gum H) as the adhesive, the skin permeation of FF was found to increase with increasing l-menthol and NMP contents. FF in the matrix patches containing NMP in the range of 4.8-7.2% was stable, but stability decreased at higher values. With a standard matrix patch containing FF, the Cmax and AUC(0-24) values were found to be 1.93 ng/ml after 4 h percutaneous application to rats and 25.6 ng x h/ml. The bioavailability after percutaneous exposure was equivalent to 15.2% of the AUC(0-24) after intravenous administration. Percutaneous application proved efficacious with regard to control of simulated asthma at dose levels lower than those with which side effects occurred. Thus an optimized matrix patch containing FF was prepared with potential advantages for control of asthma.

Administration, Cutaneous↗
PubMed1997

Skin permeation of parabens in excised guinea pig dorsal skin, its modification by penetration enhancers and their relationship with n-octanol/water partition coefficients.

Skin penetration of methyl, ethyl, propyl and butyl parabens through excised guinea pig dorsal skin was examined, and effects of the penetration enhancers, l-menthol plus ethanol itself and N-dodecyl-2-pyrrolidone, were observed. Permeability of coefficients of the parabens correlated with n-octanol/water partition coefficients. Addition of 1% l-menthol in 15% ethanol about sixteen times increased the permeability coefficient of methyl paraben, whereas this enhancer decreased that of butyl paraben to about one fifth of the control value. A similar, though weaker, tendency was observed for the effects of 15% ethanol itself. 0.025% suspension of N-dodecyl-2-pyrrolidone increased the permeability coefficient of methyl paraben about seven times, whereas it did not change that of butyl paraben significantly. Therefore, dependency of the permeability coefficients of the parabens on n-octanol/water partition coefficients almost disappeared in the presence of this compound. A spin label study with stratum corneum lipid liposomes revealed that increase of fluidity of the lipid bilayer by these penetration enhancers corresponded with their enhancement effects on skin penetration of methyl paraben. Perturbation of stratum corneum lipid lamella thus seems to be related with their enhancement of the absorption of hydrophilic paraben.

Animals↗
PubMedDate not supplied

The effects of nasal anaesthesia upon nasal sensation of airflow.

The effect of nasal anaesthesia upon the sensation of nasal airflow and activity of menthol was investigated in 25 subjects using a visual analogue scale. Nasal anaesthesia was shown to decrease the sensation of nasal airflow, and also decrease the action of menthol in enhancing the sensation of nasal airflow. These differences were shown to be highly significant p less than 0.001. Physiological mechanisms responsible for conveying the subjective appreciation of a nasal airflow stimulus are discussed, and also the site and nature of the sensory nerve endings involved.

Administration, Intranasal↗
PubMed2000

Cold, cough, allergy, bronchodilator, and antiasthmatic drug products for over-the-counter human use; amendment of final monograph for OTC antitussive drug products. Food and Drug Administration, HHS. Final rule.

The Food and Drug Administration (FDA) is issuing a final rule amending the final monograph for over-the-counter (OTC) antitussive drug products (products that relieve cough). Use of topical/inhalant products containing camphor or menthol near a flame, in hot water, or in a microwave oven may cause the products to splatter and cause serious burns to the user. As part of its ongoing review of OTC drug products, FDA is adding warnings and directions to inform consumers about these improper uses and is amending its final regulations for OTC drug labeling requirements to add this new flammability warning for antitussive drug products containing camphor or menthol.

Anti-Asthmatic Agents↗
PubMed2004

[Synthetical evaluation of promoting effect of some kinds of transdermal enhancers with grey relational cluster method].

OBJECTIVE: Synthetical evaluation of promoting effect of some kinds of transdermal enhancers was carried through. METHOD: Diclofenac sodium was used as model, and azone and l-menthol and synthetic borneol and olieic acid and essential oil from Cnidium monnieri were used as transdermal enhancers. Transdermal absorption experimentation of diclofenac sodium on the device of penetrating skins in vitro was done. Cumulation of permeation amount and penetrating rates and steady fluxes and lag times were observed, and grey relational cluster method was used to evaluate the promoting effect of some kinds of transdermal enhancers. RESULT: As for promoting effect on diclofenac sodium, azone and l-menthol were the best, and synthetic borneol and olieic acid ranked behind. CONCLUSION: Grey relational cluster method can evaluate promoting effect objectively and fairly.

Administration, Cutaneous↗
PubMed1991

Further studies on nasal sensation of airflow.

The effect of applying a eutectic mixture of local anaesthetics cream (EMLA) to the nasal vestibule, upon both nasal sensation of airflow and action of menthol was studied in 25 normal subjects. Anaesthesia of the vestibule was shown to decrease nasal sensation of airflow, p less than 0.001. The action of menthol in enhancing the sensation of nasal airflow was unchanged, p greater than 0.05. This shows that sensory nerve endings located within the nasal vestibule and mucosa, are likely to be important in conveying nasal sensation. This study expands basic scientific knowledge in this important clinical area. The site and nature of sensory nerve endings responsible and possible neurophysiological mechanisms involved are discussed.

Adult↗
PubMed1986

Effect of nicotine chewing gum on salivary secretion.

The effect of nicotine, placebo for nicotine or menthol-tasting chewing gums on salivation was studied in 25 healthy volunteers. The chewing of a commercial nicotine containing (2 mg) chewing gum (Nicorette) did not give a larger rate of salivation than did the chewing of a placebo chewing gum. For both types of chewing gums the rate of salivation was highest during the initial 5 min and it decreased thereafter. Menthol-tasting chewing gum gave a significantly higher amount of stimulated saliva. It is concluded that the addition of nicotine to a chewing gum does not provide an additional stimulus for salivation.

Adult↗
PubMed1997

Differences in the urinary metabolites of the tobacco-specific lung carcinogen 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone in black and white smokers.

Incidence and mortality rates for lung cancer in the United States are significantly greater in blacks than in whites. This disparity cannot be explained by differences in smoking behavior. We hypothesize that the observed racial differences in risk may be due to differences in the metabolic activation or detoxification of the tobacco-specific lung carcinogen 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK). To test this, different biomarkers of NNK exposure and metabolism, including the urinary metabolite 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol (NNAL) and the presumed detoxification product [4-(methylnitrosamino)-1-(3-pyridyl)but-1-yl]-beta-O-D-glucosiduronic acid (NNAL-Gluc), were examined along with questionnaire data on lifestyle habits and diet in a metabolic epidemiological study of 34 black and 27 white healthy smokers. Results demonstrated that urinary NNAL-Gluc:NNAL ratios, a likely indicator of NNAL glucuronidation and detoxification, were significantly greater in whites than in blacks (P < 0.02). In addition, two phenotypes were apparent by probit analysis representing poor (ratio < 6) and extensive (ratio > or = 6) glucuronidation groups. The proportion of blacks falling into the former, potentially high-risk group was significantly greater than that of whites (P < 0.05). The absolute levels of urinary NNAL, NNAL-Gluc, and cotinine were also greater in blacks than in whites when adjusted for the number of cigarettes smoked. None of the observed racial differences could be explained by dissimilarities in exposure or other sociodemographic or dietary factors. Also, it is unlikely that the dissimilarities are due to racial differences in preference for mentholated cigarettes, because chronic administration of menthol to NNK-treated rats did not result in either increases in urinary total NNAL or decreases in NNAL-Gluc:NNAL ratios. Altogether, these results suggest that racial differences in NNAL glucuronidation, a putative detoxification pathway for NNK, may explain in part the observed differences in cancer risk.

Adult↗