Special Problems with Biological Fluids
Joseph Chamberlain in The Analysis of Drugs in Biological Fluids, 2018
Aromatic compounds such as benzene are metabolized by direct hydroxylation, benzene itself being metabolized to phenol, and naphthalene being metabolized to β-naphthol. Further hydroxylation to catechols may also take place. Aliphatic compounds are metabolized by ω-hydroxylation to the primary alcohol. Above a certain chain length, however, ω-1 hydroxylation predominates as exemplified by the xanthine, pentifylline which is metabolized by oxidation of the hexyl side chain (Figure 2.1).162 Alcohols are further oxidized to aldehydes and ketones and aldehydes subsequently oxidized to acids. Thus, the metabolism of an aliphatic side chain such as that for pentifylline will proceed via this series of oxidations to yield a complex mixture of acids, ketones, and alcohols — all eliminated in the urine as shown in Figure 2.2.
Cosmetic Components Causing Contact Urticaria Syndrome: An Update
Ana M. Giménez-Arnau, Howard I. Maibach in Contact Urticaria Syndrome, 2014
Urticaria-angioneurotic edema after ingestion of alcohol may be due to different agents contained in the beverages, among others, yeast. Cases reported to be due to pure ethanol are rare. Case reports of contact urticaria syndrome from local application of alcohol seem even rarer: 1) Drevets et al. reported a patient who noted diffuse pruritic rash after drinking alcoholic beverages; ethyl applied to the skin provoked an erythematous reaction in about 20 minutes.[61] 2) Fischer et al. observed allergic CoU from ethyl and isopropyl alcohol.[62] 3) Gaul et al. described an urticarial-like dermatitis provoked by ethyl alcohol and stearyl alcohol associated with delayed dermatitis.[63] 4) Rilliet et al. presented a case of alcohol CoU after applying perfume or disinfecting the hands. The immediate reactions with most of the primary alcohols were positive. Passive transfer, using a method corresponding to that of Prausnitz-Küstner, was achieved.[64]
Central Nervous System Effects of Essential Oil Compounds
K. Hüsnü Can Başer, Gerhard Buchbauer in Handbook of Essential Oils, 2020
Geraniol 2 (C10, monoterpene), farnesol 3 (C15, sesquiterpene), and phytol 4 (C20, diterpene) form a good series for structure-activity-mechanism of action comparative studies. These are three primary alcohols with open chains that present an α,β-unsaturation to the carbon that bears the hydroxyl group. All three present an identical unit isopentenol that forms the polar extremity of the chain and identical isoprene units (in 2 and 3) or saturation (4) in the non-polar extremities. The MWs raise in the same sequence (2 < 3 < 4) of their XLogP3, with accompany increases in lipophilicity, whereas the other molecular descriptors remain in the same values.
Development of optimized self-nanoemulsifying lyophilized tablets (SNELTs) to improve finasteride clinical pharmacokinetic behavior
Published in Drug Development and Industrial Pharmacy, 2018
Tarek A. Ahmed, Khalid M. El-Say, Khaled M. Hosny, Bader M. Aljaeid
It was noticed from the data obtained for the globule size analysis that, as the number of carbon atom in the co-surfactant was increased the globule size of the prepared SNEDDS was decreased. As the number of carbon atoms in the alkyl group of the studied alcohols was increased, the cosurfactant hydrophobicity was increased. Accordingly, the adsorption tendency of the surfactant at the oil-water interface was enhanced. This effect is expected to decrease the interfacial tension and promote the emulsification process which leads to formation of smaller SNEDDS globule size. All of the butanol-based SNEDDS did not exhibit any sign of instability such as phase separation or precipitation while some of the methanol, ethanol and propanol based SNEDDS especially runs 2, 4, 5, 8 and to lesser extent run 7 showed this behavior. So, n-butanol was selected as a co-surfactant and this selection is also supported by the safety of this alcohol. This primary alcohol, with a four-carbon structure, occurs naturally as a minor product of the fermentation of some sugars and carbohydrates [16]. It is present in many foods and beverages and, has been permitted as an artificial flavor in butter, cream, fruit, rum, ice cream, candy, baked goods, and cordials in the United States [17].
ATP-competitive DNA gyrase and topoisomerase IV inhibitors as antibacterial agents
Published in Expert Opinion on Therapeutic Patents, 2019
Martina Durcik, Tihomir Tomašič, Nace Zidar, Anamarija Zega, Danijel Kikelj, Lucija Peterlin Mašič, Janez Ilaš
Compound 6 is a more recent benzothiazole urea derivative that has a secondary alcohol group (Figure 2). In the most recent patents, only the general activities of these benzothiazole urea derivatives are disclosed. The IC50 values for their gyrase ATPase activities are <1 µg/mL for the majority, with most being <0.1 µg/mL. Also for the majority, the MICs against S. aureus and Streptococcus pyogenes are <1 µg/mL (with compound 6 being one of these), and for the other representative compounds, these MICs range from 1–16 µg/mL. Seventy-four compounds were reported with MICs lower than 2 µg/mL against Haemophilus influenzae (including compound 6) [57]. The compounds in this patent show promising in vivo activities in a mouse thigh infection model, in which compound 6 provides a ≥ 3 log10 units drop in colony-forming units compared to the control when dosed intravenously at 30 mg/kg [33]. For selected compounds, analogues with primary alcohol groups were also prepared and compared to the corresponding examples with secondary and tertiary alcohols. These compounds with secondary and tertiary alcohol groups show improved clearance and increased AUCiv (AUCiv in the rat model: compound 6, 4 µg×h/mL; its primary alcohol analogue, 2 µg×h/mL), which demonstrates that they have advantageous pharmacokinetic profiles [57].
Crosslinking hyaluronic acid soft-tissue fillers: current status and perspectives from an industrial point of view
Published in Expert Review of Medical Devices, 2021
Jimmy Faivre, Amos I. Pigweh, Julien Iehl, Pauline Maffert, Peter Goekjian, François Bourdon
Bisepoxides are a class of chemical crosslinkers for HA in which the epoxide functionalities serve as electrophiles for the Williamson etherification via ring opening [12]. As mentioned earlier, the different bisepoxides used as crosslinkers for HA include BDDE, PEGDE, and DEO. Under strong alkaline conditions (usually at pH 13), bisepoxides react with the hydroxyl groups on the HA chains to form ether linkages as shown in Figure 1 [30]. Generally, temperatures higher than 40°C over a few hours of reaction are reported [31,32]. This leads to the modification of hydroxyl groups at different positions, not necessarily on the primary alcohol [33,34]. The resulting bridge between both HA chains creates an elastic crosslinked HA hydrogel network. Typically, degrees of modification (MoD), commonly measured by 1H NMR, are reported between 1 and 10% for BDDE-crosslinked HA fillers [35,36], the MoD being defined as the molar ratio of crosslinker to HA disaccharide units. This parameter represents the total HA modification, although the crosslinker may be either linked to a single HA strand, or may effectively crosslink two HA chains [36].
Related Knowledge Centers
- Alcohol
- Ethanol
- Methanol
- Hydroxy Group
- Primary Carbon
- 1-Butanol
- Oxidation of Alcohols to Carbonyl Compounds