Phenol/Phenylmercuric Salts 1657 Ingrowing toenails. Liquefied phenol (88%) ablation has been water; miscible with alcohol, with acetone, and with glycerol; Incompatibility. The incompatibilities of phenylmercuric salts performed as an alternative to surgical avulsion in the treatment slightly soluble in arachis oil and in olive oil. Store in a dry place, are described under Phenylmercuric Nitrate, below. of ingrowing toenails.1,2 A systematic review3 concluded that in airtight containers at a temperature of 8° to 15°. Protect from simple nail avulsion combined with treating the nail-bed with light. Phenylmercuric Borate (rINN) phenol was more effective at preventing symptomatic recurrence Borato de fenilmercurio; Fenilgyvsidabrio boratas; Fenil-higany- of ingrowing toenails than cutting out the nail-bed. However, Incompatibility. The activity of phenoxyethanol may be re- there was a significant increase in postoperative infections when duced by interaction with nonionic surfactants and possibly by borát; Fenylhydrargyriumborát; Fenylkvicksilverborat; Fenylortę- phenol was used. adsorption onto PVC. ciowy boran; Fenyylimerkuriboraatti; Hydrargyrum Phenylobori- 1. Bostanci S, et al. Chemical matricectomy with phenol for the Profile cum; Phenomerborum; Phenylhydrargyri boras; Phénylmercure, treatment of ingrowing toenail: a review of the literature and fol- Phenoxyethanol is effective against strains of Pseudomonas aer- borate de. low-up of 172 treated patients. Acta Derm Venereol 2001; 81: Фенилмеркурборат 181–3. uginosa but less so against other Gram-negative and Gram-pos- 2. Andreassi A, et al. Segmental phenolization for the treatment of itive bacteria. It has been used as a preservative in cosmetics and C6H5HgOH,C6H5HgOB(OH)2 =633.2 or C6H5HgOH, ingrowing toenails: a review of 6 years experience. J Dermatol topical pharmaceuticals at a concentration of 0.5 to 1%. It is often C6H5HgBO2 = 615.2. Treat 2004; 15: 179–81. used with other preservatives, commonly hydroxybenzoates, to CAS — 8017-88-7 (C12H13BHg2O4); 6273-99-0 3. Rounding C, Bloomfield S. Surgical treatments for ingrowing obtain a wider spectrum of antimicrobial activity. (C12H11BHg2O3); 102-98-7 (C6H7BHgO3). toenails. Available in The Cochrane Database of Systematic Re- ATC — D08AK02. views; Issue 1. Chichester: John Wiley; 2003 (accessed Phenoxyethanol is used in concentrations of about 2% as an an- ATC Vet — QD08AK02. 15/03/06). tiseptic for minor infections of skin, wounds, and mucous mem- Pain. The neurolytic use of phenol to produce destructive nerve branes. Aqueous solutions may be prepared by shaking the phe- block (see under Pain, p.1852) has produced variable results, and noxyethanol with hot water until dissolved, then adjusting to OH some consider the risk of complications outweighs the benefits. final volume when cool. Preparation of the solution can be aided However, it may have the advantage over alcohol that it is pain- by propylene glycol. Hg Hg B OH O OH less on injection, and smaller volumes can be used, potentially Phenoxypropanol and chlorophenoxyethanol are related com- allowing greater precision (see p.1627). pounds used in topical preparations. Urinary incontinence. Although injection of phenol into the Preparations pelvic plexus to produce partial denervation has been used in the Pharmacopoeias. In Eur. (see p.vii). management of severe intractable urge incontinence, its use has Proprietary Preparations (details are given in Part 3) Ph. Eur. 6.2 (Phenylmercuric Borate). A compound consisting been largely abandoned. Some patients, especially those with de- Singapore: Acnederm Wash; UK: Biactol Liquid. of equimolecular proportions of phenylmercuric orthoborate and trusor hyperreflexia, have derived benefit1,2 but overall efficacy Multi-ingredient: Arg.: Cicatul; Polviderm NF; Austral.: Acnederm phenylmercuric hydroxide (C H BHg O ) or of the dehydrated can be poor and benefits short-lived.3 Foaming Wash; Acnederm Medicated; Austria: Octenisept; Chile: Eucerin 12 13 2 4 Piel Grasa; Fr.: Alco-Aloe; Manugel; Ger.: Gigasept Med†; Lysetol Med†; form (metaborate, C12H11BHg2O3) or a mixture of the two com- 1. Ewing R, et al. Subtrigonal phenol injection therapy for inconti- Octenisept; Gr.: Octenisept; Ital.: Decon Ovuli; Fitostimoline; Malaysia: pounds. Colourless shiny crystals or a white or slightly yellowish nence in female patients with multiple sclerosis. Lancet 1983; i: Acnederm Foaming Wash; Acnederm Lotion; Mex.: Fitoestimulina; Italder- 1304–5. mol; NZ: Acnederm; Acnederm Foaming Wash; Singapore: Acnederm; crystalline powder. Slightly soluble in water and in alcohol. Pro- 2. Blackford HN, et al. Results of transvesical infiltration of the Switz.: Ederphyt†; Octenisept; USA: Bodi Kleen; Venez.: Glizigen; Photo- tect from light. pelvic plexuses with phenol in 116 patients. Br J Urol 1984; 56: derm AKN. 647–9. Incompatibility. The incompatibilities of phenylmercuric salts 3. Rosenbaum TP, et al. Trans-trigonal phenol failed the test of are described under Phenylmercuric Nitrate, below. time. Br J Urol 1990; 66: 164–9. Preparations Phenoxyisopropanol Phenylmercuric Nitrate BP 2008: Aqueous Phenol Injection; Liquefied Phenol; Oily Phenol Injec- Fenoxiisopropanol; Phenoxyisopropyl Alcohol. 1-phenoxypro- Basic Phenylmercury Nitrate; Fenilgyvsidabrio nitratas; Fenil-higa- tion; Phenol and Glycerol Injection; pan-2-ol. ny-nitrát; Fenilmercurio, nitrato de; Fenylhydrargyriumnitrát; Fe- BPC 1973: Magenta Paint; nylkvicksilvernitrat; Fenylortęci(II) azotan; Fenyylimerkurinitraatti; USP 31: Camphorated Phenol Topical Gel; Carbol-Fuchsin Topical Solu- C9H12O2 = 152.2. Phenylhydrargyri nitras; Phénylmercure, nitrate de; PMN. Nitrat- tion; Liquefied Phenol; Phenolated Calamine Topical Suspension. CAS — 770-35-4. Proprietary Preparations (details are given in Part 3) ophenylmercury. Austral.: Summers Eve Disposable†; Canad.: Chloraseptic Spray; P & S; C6H5HgOH,C6H5HgNO3 = 634.4. Chile: Metapio; S.Afr.: Medi-Keel A; SB Aurico Ear Drops; Septosol; Thai.: CAS — 8003-05-2 (C6H5HgOH,C6H5HgNO3); 55-68-5 Pose-Cresol; UK: Ultra Chloraseptic; USA: Cheracol Sore Throat; Chlo- HO (C6H5HgNO3). raseptic Kids Sore Throat Spray; Chloraseptic Sore Throat; Green Throat ATC — D09AA04. Spray; P & S; Phenaseptic; Red Throat Spray; Triaminic Sore Throat Spray; Ulcerease. ATC Vet — QD09AA04. H C O Multi-ingredient: Arg.: Aceite Esmeralda Moone; Callicida; Dermithan; 3 Manzan; Piracalamina; Prurisedan; Prurisedan Rosa; Austral.: Ayrton’s Chil- blain; Calamine Lotion; Egopsoryl TA; Nyal Toothache Drops; Sarna; Aus- O tria: Herposicc; Belg.: Eucalyptine Pholcodine; Sedemol; Sulfa-Sedemol; + Braz.: Algidente†; Cloraseptic; Dentisan; Otoloide; Pradente†; Timpanol†; Profile Hg Hg N Um Instante†; Usedent†; Canad.: Anbesol Maximum Strength; Blistex Phenoxyisopropanol is used as a preservative and as an antiseptic OH O O- DCT Lip Balm; Blistex Lip Medex; Blistex Medicated Lip Conditioner Jar†; in preparations for the treatment of acne, insect bites, and minor Blistex Medicated Lip Ointment; Boil Ease†; Cepastat; Chapstick Medicated abrasions to the skin. Lip Balm†; Lip Medex†; Mecca; Ozonol; Phenoris; Chile: Blistex; Chapstick Medicated; Fr.: Brulex; Hong Kong: Blistex Lip Ointment†; Cepastat; Preparations Doans†; Egopsoryl TA; Hung.: Reparon; Ital.: Creosoto Composto; Dia- (C6H5HgOH,C6H5HgNO3) ril†; Eso Din; Fucsina Fenica; Lavanda Sofar; Ondroly-A†; Pinselina Knapp; Proprietary Preparations (details are given in Part 3) Malaysia: Egopsoryl TA; Sarna; Mex.: Forcremol; Neth.: Agre-Gola; NZ: Austral.: Clearasil Daily Face Wash. Egopsoryl TA; Toothache Drops†; Philipp.: Calmoseptine; Sarna; Pol.: Pig- Pharmacopoeias. In Eur. (see p.vii) and Int. Also in USNF. mentum Castellani; Port.: Calicida Indiano; S.Afr.: Alpha Toothache Es- Ph. Eur. 6.2 (Phenylmercuric Nitrate). A mixture of phenylmer- sence; Biohist; Blistex; Calasthetic; Cuticura†; Germolene; Lacto Calamine†; curic nitrate and phenylmercuric hydroxide. A white or pale yel- Prep; SB Universal Ointment; TCP; Singapore: Cepastat; Egopsoryl TA; Sarna; Spain: Argentofenol†; Carbocaina†; Dermomycose Liquido; low powder. Very slightly soluble in water and in alcohol; slight- Odontocromil c Sulfamida†; Otocerum; Otogen Calmante; Sabanotropico; Phenylmercuric Salts ly soluble in hot water; dissolves in glycerol and in fatty oils. Switz.: Caustinerf forte†; Thai.: Con Con; Lanol; Sarna; Zema; Turk.: Disi- Protect from light. nol; UK: Blistex Relief Cream; Chymol; Colsor; Dermacreme; Germolene; Fenilmercurio, sales. USNF 26 (Phenylmercuric Nitrate). A mixture of phenylmercu- Lacto Calamine; TCP; USA: Anbesol; Blistex; Blistex Lip Balm; Boil Ease; Campho-Phenique; Castaderm; Cepastat; Cepastat Cherry; Chapstick ric nitrate and phenylmercuric hydroxide. A white crystalline Medicated Lip Balm; Columbia Antiseptic Powder; Debacterol; Heal Aid Phenylmercuric Acetate powder. Soluble 1 in 600 of water; slightly soluble in alcohol and Plus; Lip Medex; Lipmagik; Massengill; Mycinette; Nasal Jelly; Orabase Lip; in glycerol; more soluble in the presence of nitric acid or alkali Orasol; Phylorinol; Skeeter Stik; Sting-Eze; Unguentine; Unguentine Plus. Fenilgyvsidabrio acetatas; Fenil-higany-acetát; Fenilmercurio, ace- hydroxides. A saturated solution in water is acid to litmus. Store tato de; Fenylhydrargyriumacetát; Fenylkvicksilveracetat; Feny- in airtight containers. Protect from light. lortęciowy octan; Fenyylimerkuriasetaatti; Phenylhydrargyni ace- tas; Phenylhydrargyri Acetas; Phénylmercure, acétate de; PMA. Incompatibility. The activity of phenylmercuric salts may be Phenoxyethanol reduced by interaction with compounds such as kaolin, magnesi- (Acetato)phenylmercury. Ethylene Glycol 2-Monophenyl Ether; Ethyleneglycol Monophe- um trisilicate, starch, and talc.1,2 Disodium edetate and sodium 3 nylether; Fenoksietanoli; Fenoksietanolis; Fenoksyetanol; Fenoxi- C8H8HgO2 = 336.7. thiosulfate can also produce inactivation. Sodium metabisulfite CAS — 62-38-4. can lead to precipitation,3 or chemical destruction,4 but it can also etanol; Fenoxyethanol; Phenoxyaethanol; Phénoxyéthanol; Phe- 3 noxyethanolum; β-Phenoxyethyl Alcohol; 2-Phenoxyethyl Alco- produce increased activity. Other incompatibilities include bro- mides, iodides (chlorides to a lesser extent), metals, and ammo- hol. 2-Phenoxyethanol. O nia and its salts.5 There can be adsorption onto rubber and some C8H10O2 = 138.2. plastics5,6 although sorption by low density polyethylene can be CAS — 122-99-6. Hg inhibited by phosphate ions.7 Some filters, though not membrane OCH3 filters, used for sterilisation removed considerable amounts of phenylmercuric nitrate from solution.8 The pH may also affect OH activity.9 1. Yousef RT, et al. Effect of some pharmaceutical materials on the Pharmacopoeias. In Eur. (see p.vii). Also in USNF. bactericidal activities of preservatives. Can J Pharm Sci 1973; 8: O 54–6. Ph. Eur. 6.2 (Phenylmercuric Acetate). A white or yellowish 2. Horn NR, et al. Interactions between powder suspensions and crystalline powder or small, colourless crystals. Slightly soluble selected quaternary ammonium and organomercurial preserva- Pharmacopoeias. In Eur. (see p.vii). Also in USNF. in water; soluble in alcohol and in acetone. Protect from light. tives. Cosmet Toilet 1980; 95: 69–73. Ph. Eur. 6.2 (Phenoxyethanol). A colourless slightly viscous USNF 26 (Phenylmercuric Acetate). A white to creamy-white, 3. Richards RME, Reary JME. Changes in antibacterial activity of liquid. Slightly soluble in water, in arachis oil and in olive oil; odourless, crystalline powder or small white prisms or leaflets. thiomersal and PMN on autoclaving with certain adjuvants. J Pharm Pharmacol 1972; 24 (suppl): 84P–89P. miscible with alcohol, with acetone, and with glycerol. Soluble 1 in 180 of water, 1 in 225 of alcohol, 1 in 6.8 of chloro- 4. Collins AJ, et al. Incompatibility of phenylmercuric acetate with USNF 26 (Phenoxyethanol). A colourless, slightly viscous liq- form, and 1 in 200 of ether; soluble in acetone. Store in airtight sodium metabisulphite in eye drop formulations. J Pharm Phar- uid. Specific gravity 1.105 to 1.110 at 20°. Slightly soluble in containers. Protect from light. macol 1985; 37 (suppl): 123P. The symbol † denotes a preparation no longer actively marketed The symbol ⊗ denotes a substance whose use may be restricted in certain sports (see p.vii)