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1120 Bronchodilators and Anti-Asthma Drugs 1120 Bronchodilators and Anti-asthma Drugs Profile Preparations unchanged in the urine with an elimination half-life of about 2 Cilomilast is a phosphodiesterase type-4 inhibitor that has been Proprietary Preparations (details are given in Part 3) hours. Diprophylline is distributed into breast milk. investigated in the treatment of chronic obstructive pulmonary Arg.: Bronq-C; Clembumar; Oxibron; Austria: Spiropent; Chile: Airum; disease. Uses and Administration Asmeren; Broncotosil†; Cz.: Spiropent; Ger.: Contraspasmin†; Spiropent; Diprophylline is a theophylline derivative which is used similar- Gr.: Spiropent; Hong Kong: Clenasma†; Hung.: Spiropent; Indon.: Spiropent; Ital.: Clenasma†; Monores; Prontovent†; Spiropent; Jpn: ly to theophylline (p.1146) as a bronchodilator in reversible air- Spiropent; Mex.: Novegam; Oxyflux; Spiropent; Philipp.: Spiropent; ways obstruction. Clenbuterol Hydrochloride (BANM, rINNM) ⊗ Port.: Broncoterol; Cesbron; Spain: Spiropent†; Ventolase; Venez.: Brodi- The usual oral dose of diprophylline is up to 15 mg/kg every 6 lan; Brodilin; Buclen; Clenbunal; Risopent. Clenbutérol, chlorhydrate de; Clenbuteroli hydrochloridum; Hid- hours. It has also been given intramuscularly. Diprophylline is Multi-ingredient: Arg.: Mucosolvon Compositum; Oxibron NF; Aus- rocloruro de clenbuterol; Klenbuterol hydrochlorid; Klenbuterol- also an ingredient of preparations that have been promoted for tria: Mucospas; Ger.: Spasmo-Mucosolvan; Mex.: Ambodil-C; Balsibron- coughs. hidroklorid; Klenbuterolhydroklorid; Klenbuterolihydrokloridi; C; Brogal Compositum; Bronolban-M; Brosolan C; Broxofar Compuesto; Klenbuterolio hidrochloridas; NAB-365 (clenbuterol). 1-(4-Ami- Broxol Plus; Broxolim-C; Ebromin P; Fludexol-CL; Loxorol; Mucosolvan Action. Improvements in measurements of lung function after Compositum; Mucovibrol C; Sekretovit Ex; Septacin Ex; Seraxol; Serbol; no-3,5-dichlorophenyl)-2-tert-butylaminoethanol hydrochloride. diprophylline in oral doses of 15 and 20 mg/kg were only one- Port.: Clembroxol; Mucospas; Ventoliber; Venez.: Ambromuco Composi- 1 Кленбутерола Гидрохлорид tum; Arbixil; Clenbuxol; Litusix Compositum; Mucolin; Mucosolvan Com- third to one-half those obtained after oral theophylline 6 mg/kg. C H Cl N O,HCl = 313.7. positum. 1. Furukawa CT, et al. Diphylline versus theophylline: a double- 12 18 2 2 blind comparative evaluation. J Clin Pharmacol 1983; 23: CAS — 37148-27-9 (clenbuterol); 21898-19-1 (clen- 414–18. buterol hydrochloride). Preparations ATC — R03AC14; R03CC13. Diprophylline (BAN, rINN) ATC Vet — QR03AC14; QR03CC13. USP 31: Dyphylline and Guaifenesin Elixir; Dyphylline and Guaifenesin Tab- Dihydroxypropyltheophyllinum; Diprofilina; Diprofilinas; Diprofil- lets; Dyphylline Elixir; Dyphylline Injection; Dyphylline Tablets. lin; Diprofylin; Diprofylliini; Diprofyllin; Diprophyllinum; Dyphyl- Proprietary Preparations (details are given in Part 3) OH line; Glyphyllinum; Hyphylline. 7-(2,3-Dihydroxypropyl)-1,3- Austria: Austrophyllin†; Gr.: Silbephylline†; Hong Kong: Syneophylline; H dimethylxanthine; 7-(2,3-Dihydroxypropyl)theophylline. Ital.: Katasma; Port.: Neufil; Turk.: Difilin; USA: Dilor†; Dylix; Lufyllin. Cl N Дипрофиллин Multi-ingredient: Fr.: Ozothine a la Diprophylline; Israel: Philinal; Phili- C(CH3)3 net; Ital.: Cort-Inal; Spain: Alergical Expect; Bronsal; Novofilin†; UK: No- C10H14N4O4 = 254.2. radran; USA: Difil-G; Dilex-G; Dy-G; Dyflex-G; Dyline GG†; Dyphylline- GG; Jay-Phyl; Lufyllin-EPG†; Lufyllin-GG; Panfil G. H2N CAS — 479-18-5. ATC — R03DA01. Cl ATC Vet — QR03DA01. (clenbuterol) Doxofylline (USAN, rINN) ABC 12/3; Doxofilina; Doxofyllinum. 7-(1,3-Dioxolan-2-ylme- OH NOTE. The following terms have been used as ‘street names’ (see thyl)theophylline. p.vi) or slang names for various forms of clenbuterol: OH O Доксофиллин Angel Dust; C H N O = 266.3. Clen. H C 11 14 4 4 3 N CAS — 69975-86-6. Pharmacopoeias. In Chin. and Eur. (see p.vii). N ATC — R03DA11. Ph. Eur. 6.2 (Clenbuterol Hydrochloride). A white or almost ATC Vet — QR03DA11. white crystalline powder. Soluble in water and in alcohol; slight- O N N ly soluble in acetone. A 5% solution in water has a pH of 5.0 to 7.0. CH N CH3 Profile 3 O N Clenbuterol hydrochloride is a direct-acting sympathomimetic Pharmacopoeias. In Chin., Eur. (see p.vii), and US. N O with mainly beta-adrenergic activity and a selective action on Ph. Eur. 6.2 (Diprophylline). A white or almost white, crystal- beta2 receptors (a beta2 agonist). It has properties similar to those line powder. Freely soluble in water; slightly soluble in alcohol. O N of salbutamol (p.1131). It is used as a bronchodilator in the man- Protect from light. agement of reversible airways obstruction, as in asthma (p.1108) O CH3 USP 31 (Dyphylline). A white, odourless, amorphous or crystal- and in certain patients with chronic obstructive pulmonary dis- line solid. Freely soluble in water; sparingly soluble in alcohol ease (p.1112). A usual oral dose is 20 micrograms twice daily; and in chloroform; practically insoluble in ether. A 1% solution Profile doses of up to 40 micrograms twice daily have occasionally been in water has a pH of 5.0 to 7.5. Store in airtight containers. Doxofylline is a theophylline derivative (p.1140) which is used given. Clenbuterol hydrochloride has also been given by inhala- as a bronchodilator in reversible airways obstruction. It is given tion. In patients with asthma, as-required beta agonist therapy is Adverse Effects, Treatment, and Precautions in oral doses of up to 1200 mg daily. It may also be given by slow preferable to regular use. An increased need for, or decreased du- As for Theophylline, p.1140. Diprophylline is primarily excreted intravenous injection. ration of effect of, clenbuterol indicates deterioration of asthma unchanged in the urine and should therefore be used with caution control and the need for review of therapy. in patients with renal impairment; dose adjustments may be re- Preparations Abuse. Clenbuterol has been used illicitly in animal feeds in an quired. However, unlike theophylline, plasma concentrations of Proprietary Preparations (details are given in Part 3) attempt to promote weight gain and to increase muscle to lipid diprophylline are not greatly affected by changes in liver func- Ital.: Ansimar; Mex.: Axofin; Philipp.: Ansimar; Thai.: Puroxan. mass. Adverse effects typical of sympathomimetic activity have tion or hepatic enzyme activity such as those produced by smok- been attributed to such misuse both in farmers perpetrating such ing or age. acts1 and in innocent persons consuming meat products from af- Breast feeding. In a study of 20 women given diprophylline by Etamiphylline Camsilate (BANM, rINNM) fected animals.2-5 Clenbuterol has been abused by sportsmen for 1 intramuscular injection, diprophylline was found to concentrate Camsilato de etamifilina; Diétamiphylline Camphosulfonate; its anabolic effects,6 although it is doubtful as to whether it en- in breast milk, with a milk to serum concentration ratio of about hances performance.7 Myocardial infarction was described in an Étamiphylline, Camsilate d’; Etamiphylline Camsylate; Etamiphyl- 2. However, it was felt that the quantity of diprophylline a breast- lini Camsilas; Etamphyllin Camsylate. 7-(2-Diethylaminoethyl)- otherwise healthy 17-year-old bodybuilder after abuse of clen- fed infant would ingest was unlikely to produce any pharmaco- buterol.8 Coronary artery spasm and/or temporary thrombosis logical action unless the child was very sensitive. The American 1,3-dimethylxanthine camphor-10-sulphonate; 7-(2-Diethylami- were suggested as possible explanations for this adverse effect. Academy of Pediatrics2 also considers that the use of diprophyl- noethyl)theophylline camphor-10-sulphonate. Contamination of illicit heroin with clenbuterol has also been re- line is usually compatible with breast feeeding. Этамифиллина Камзилат ported.9 1. Jarboe CH, et al. Dyphylline elimination kinetics in lactating C23H37N5O6S = 511.6. 1. Dawson J. β Agonists put meat in the limelight again. BMJ 1990; women: blood to milk transfer. J Clin Pharmacol 1981; 21: CAS — 314-35-2 (etamiphylline); 19326-29-5 (etami- 301: 1238–9. 405–10. phylline camsilate). 2. Martínez-Navarro JF. Food poisoning related to consumption of 2. American Academy of Pediatrics. The transfer of drugs and oth- ATC — R03DA06. illicit β-agonist in liver. Lancet 1990; 336: 1311. er chemicals into human milk. Pediatrics 2001; 108: 776–89. 3. Maistro S, et al. Beta blockers to prevent clenbuterol poisoning. Correction. ibid.; 1029. Also available at: ATC Vet — QR03DA06. Lancet 1995; 346: 180. http://aappolicy.aappublications.org/cgi/content/full/ 4. Brambilla G, et al. Food poisoning following consumption of pediatrics%3b108/3/776 (accessed 19/03/08) clenbuterol-treated veal in Italy. JAMA 1997; 278: 635. O 5. Ramos F, et al. Proposed guidelines for clenbuterol food poison- Interactions N CH3 ing. Am J Med 2004; 117: 362. Since diprophylline does not undergo metabolism by hepatic mi- H C 6. Anonymous. Muscling in on clenbuterol. Lancet 1992; 340: 403. 3 N crosomal cytochrome P450 it does not exhibit the numerous in- N 7. Spann C, Winter ME. Effect of clenbuterol on athletic perform- CH3 ance. Ann Pharmacother 1995; 29: 75–7. teractions seen with theophylline (p.1142). However, the possi- 8. Kierzkowska B, et al. Myocardial infarction in a 17-year-old bility of synergistic effects should be borne in mind if it is N body builder using clenbuterol. Circ J 2005; 69: 1144–6. prescribed with other xanthines.
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