Degradation reference materials 2017 S-oxides
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1 Degradation reference materials oxides LGC Quality I 9001
2 Welcome to LGCs degradation reference standards with focus on -oxides. Active pharmaceutical ingredients (APIs) containing sulfur as a thioether are prone to degrade to -xides readily and quickly under oxidative stress. LGC s impurity reference standards are designed to be used at all relevant stages of the testing chain. The use of our -xide impurities facilitate an assessment of the oxidative stress a particular product has been subjected to, the purity of the originating API, and help determine the shelf life of the product. Each impurity is accompanied by a detailed certificate of analysis, providing all the information you need to best use the reference material. ur products can be used with confidence during analytical research and development and validation studies as well as for stability monitoring and routine quality control purposes. Visit our webshop lgcstandards.com To find out more contact your local LGC office. LGC provides a range of -oxide impurity reference standards for more than 40 major APIs.
3 Certificate of Analysis Example Certificate of Analysis Reference tandard Methyl [5-Propylsulphonyl)-1benzimidazol-2-yl]carbamate Catalogue umber: MM Molecular ormula: C Molecular Weight: CA umber: Lot umber: Long-term torage: 2 to 8 C, dark Appearance: off-white solid Melting Point: 272 C Assay as is : 98.7 % Date of shipment: 2017-July-19 This certificate is valid for two years from the date of shipment provided the substance is stored under the recommended conditions unopened in the original container. LGC Gmb, Im Biotechnologiepark, TGZ II, D Luckenwalde, Germany 6 Pages
4 Certificate of Analysis Example I. Identity The identity of the reference substance was established by following analyses. Ia. 1 -MR pectrum Conditions: 400 Mz, DM-d 6 The structure is confirmed by the signals of the spectrum and their interpretation. MM lot number LGC Gmb, Im Biotechnologiepark, TGZ II, D Luckenwalde, Germany Page 2/6
5 Certificate of Analysis Example Ib. Mass pectrum Method: 4.5 kv EI+; vaporization temperature: 200 C The signals of the mass spectrum and their interpretation are consistent with the structural formula. Ic. IR pectrum Method: Attenuated Total Reflection ourier Transform Infrared (ATR-TIR) pectroscopy The signals of the IR spectrum and their interpretation are consistent with the structural formula. MM lot number LGC Gmb, Im Biotechnologiepark, TGZ II, D Luckenwalde, Germany Page 3/6
6 Certificate of Analysis Example II. Purity IIa. igh Performance Liquid Chromatography (PLC) The purity of the reference substance was analysed by high performance liquid chromatography (PLC). PLC Conditions: Column: Conditions: Detector: Injector: ypersil Gold C ml/min, 40 C DAD Auto 5 µm, 150 x 4.6 mm 0-6 min Water/Acetonitrile 82/ min Water/Acetonitrile to 30/ min Water/Acetonitrile to 82/ min Water/Acetonitrile 82/18 (v/v); 0.1 % 3P nm 1 µl; mg/ml in Water/Acetonitrile 50/50 (v/v) MM lot number LGC Gmb, Im Biotechnologiepark, TGZ II, D Luckenwalde, Germany Page 4/6
7 Certificate of Analysis Example Area Percent Report - orted by ignal Pk # Retention Time Area Area % Totals or the calculation the system peaks were ignored. The content of the analyte was determined as ratio of the peak area of the analyte and the cumulative areas of the purities, added up to 100 %. Results: Average % umber of results n=3 tandard deviation < 0.01 % IIb. Water Content Method: Karl ischer titration Results: Average 0.24 % umber of results n=3 tandard deviation 0.02 % IIc. Residual olvents Method: 1 -MR o significant amounts of residual solvents were detected (< 0.05 %). MM lot number LGC Gmb, Im Biotechnologiepark, TGZ II, D Luckenwalde, Germany Page 5/6
8 Certificate of Analysis Example III. inal Result Chromatographic purity (PLC) % Water content 0.24 % Residual solvents o significant amounts of residual solvents were detected (< 0.05 %). Assay (100 % method) % The assay is assessed to be 98.7 % as is The assay 'as is' is equivalent to the assay based on the not anhydrous and not dried substance respectively. Release Date: Luckenwalde, Dr. abine chröder Product Release 1 The calculation of the 100 % method follows the formula: Assay (%) = (100 % - volatile contents) * Purity (%) 100 % Volatile contents are considered as absolute contributions, purity is considered as relative contribution. MM lot number LGC Gmb, Im Biotechnologiepark, TGZ II, D Luckenwalde, Germany Page 6/6
9 Products -oxides Table of products -oxides A. Albendazole B. Butoconazole itrate C. Carbocisteine indamycin Phosphate D. Diethazine ydrochloride Dosulepin ydrochloride E. Emtricitabine Esomeprazole Magnesium Trihydrate. amotidine luphenazine Dihydrochloride L. Lansoprazole Levomepromazine Maleate M. Mequitazine Methionine. meprazole xfendazole P. Pantoprazole odium esquihydrate Protionamide R. Ranitidine ydrochloride. ulforidazine T. Thioridazine ydrochloride Trimeprazine Tartrate
10 Products -oxides MM Imp. B (EP): Methyl [5-Propylsulphinyl)- 1-benzimidazol-2-yl]carbamate mg MM Imp. C (EP): Methyl [5-Propylsulphonyl)- 1-benzimidazol-2-yl]carbamate mg MM Butoconazole ulfoxide ydrochloride n/a 100mg MM Butoconazole ulfone n/a 100mg MM ()-Carboxymethyl-L-cysteine (R/)-ulphoxide mg 2 MM Imp. A (EP): 3-(2-Chloro-10-phenothiazin- 10-yl)-,-dimethylpropan-1-amine -xide (Chlorpromazine ulfoxide) mg MM Chlorpromazine ulphoxide -xide Maleate mg + MM Chlorpromazine ulfone ydrochloride mg MM Chlorpromazine ulfone -xide ydrochloride (Chlorpromazine,,-Trioxide ydrochloride) mg + MM Imp. E (EP): 2-Cyano-1-methyl-3-[2-[[(5- methyl-1-imidazol-4-yl)methyl]sulphinyl]- ethyl]guanidine (Cimetidine ulphoxide) mg MM indamycin Palmitate ulfoxide mg MM indamycin Phosphate ulfoxide mg P MM indamycin Phosphate ulfone n/a 100mg P Edition 2017 Visit us at B-1
11 Products -oxides MM indamycin Phosphate ulfoxide trans--xide n/a 100mg + P MM indamycin Phosphate ulfone trans--xide n/a 100mg + P MM Diethazine ulfoxide mg MM Diethazine ulfone mg MM Diethazine ulfoxide -xide ydrochloride (Diethazine,- Dioxide ydrochloride) n/a 100mg + MM Diethazine ulfone -xide ydrochloride (Diethazine,,- Trioxide ydrochloride) n/a 100mg + MM Diltiazem ulphoxide mg MM Imp. A (EP): (E)-3-(5-xo-5 4 -dibenzo[b,e]thiepin-11(6)- ylidene)-,-dimethylpropan-1-amine (Dosulepin ulfoxide) mg MM Imp. D (EP) as ydrochloride: (E)-3-(5,5-Dioxo-5 6-dibenzo [b,e]thiepin-11(6)-ylidene)-,-dimethylpropan-1-amine ydrochloride (Dosulepin ulfone ydrochloride) mg MM Dosulepin ulfoxide -xide ydrochloride (Dosulepin,- Dioxide ydrochloride) n/a 100mg + MM Dosulepin ulfone -xide ydrochloride (Dosulepin,,- Trioxide ydrochloride) n/a 100mg + Edition 2017 Visit us at B-2
12 Products -oxides 2 MM Emtricitabine ulfoxide mg 2 MM Emtricitabine ulfone mg MM Erdosteine ulfoxide n/a 100mg MM Imp. D (EP): 5-Methoxy-2-[[(4-methoxy-3,5- dimethylpyridin-2-yl)methyl]sulphonyl]-1benzimidazole (meprazole ulphone) mg MM Imp. I (EP): 3-[[[2-[(Diaminomethylene)amino]thiazol-4-yl] methyl]sulfinyl]--sulfamoylpropanamide mg MM amotidine ulfoxide mg MM enbendazole ulphoxide (xfendazole) mg MM enbendazole ulphone mg MM Imp. B (EP): 1-[(2R)-2-(2,4-Dichlorophenyl)-2-[[4- (benzenesulfinyl)benzyl]oxy]ethyl]-1-imidazole (enticonazole ulfoxide) mg MM Imp. C (EP): 1-[(2R)-2-(2,4-Dichlorophenyl)-2-[[4- (benzenesulfonyl)benzyl]oxy]ethyl]-1-imidazole (enticonazole ulfone) mg Edition 2017 Visit us at B-3
13 Products -oxides MM (EZ)-3-[2-(Trifluoromethyl)-9-thioxanthen-9-ylidene]propene ulfoxide (9-Allylidene-2-(trifluoromethyl)thioxanthene 10- xide) n/a 100mg MM Imp. A (EP): 2-[4-[3-[5-xo-2-(trifluoromethyl) phenothiazin-10-yl]propyl]piperazin-1- yl]ethanol (luphenazine -xide) mg MM luphenazine ulfone 1,4-Dioxide (luphenazine 1,4,,-Tetraoxide) mg + + MM (Trifluoromethyl)-10-phenothiazine 5,5-Dioxide mg MM Lansoprazole ulphone -xide mg + MM Imp. B (EP): 10-[(2R)-3-(Dimethylamino)-2- methylpropyl]-2-methoxy-10-phenothiazine 5-xide (Levomepromazine -xide) mg MM Levomepromazine ulphone ydrochloride mg MM Levomepromazine ulfone -xide (Levomepromazine,,- Trioxide) n/a 50mg + AD Enantiomer MM Mequitazine ulfoxide mg MM Imp A (EP): (2)-2-Amino-4-[(R)-methylsulfinyl]butanoic Acid (L-Methionine ulfoxide) mg 2 MM Imp B (EP): (2)-2-Amino-4-(methylsulfonyl)butanoic Acid (L- Methionine ulfone) mg 2 Edition 2017 Visit us at B-4
14 Products -oxides MM Imp. D (EP): 5-Methoxy-2-[[(4-methoxy-3,5- dimethylpyridin-2-yl)methyl]sulphonyl]-1benzimidazole (meprazole ulphone) mg MM Imp. I (EP): 4-Methoxy-2-[[(5-methoxy-1- benzimidazol-2-yl)sulphonyl]methyl]-3,5- dimethylpyridine 1-xide (meprazole ulphone -xide) mg + MM Imp. B (EP): Methyl [5-(Phenylsulphonyl)- 1-benzimidazol-2-yl]carbamate (enbendazole ulphone) mg MM Pantoprazole ulphone -xide mg + MM Perazine ulphoxide mg MM Imp. A (EP): 2-[4-[3-(2-Chloro-5-oxido-10- phenothiazin-10-yl)propyl]piperazin-1-yl]- ethanol (Perphenazine ulphoxide) mg MM Perphenazine ulfone n/a 50mg MM Perphenazine ulfoxide 1-xide (Perphenazine 1,- Dioxide) n/a 100mg + MM Perphenazine ulfoxide 1,4-Dioxide (Perphenazine 1,4,-Trioxide) n/a 100mg + + MM MM Perphenazine ulfoxide 1,4-Dioxide Dihydrochloride (Perphenazine 1,4,-Trioxide Dihydrochloride) Perphenazine ulfone 1,4-Dioxide Dihydrochloride (Perphenazine 1,4,,-Tetraoxide Dihydrochloride) 2 n/a 100mg n/a 100mg + + MM Prochlorperazine ulfoxide mg MM Prochlorperazine ulfone Dimaleate n/a 100mg 2 MM Prochlorperazine ulfone 1,4-Dioxide Dihydrochloride (Prochlorperazine 1,4,,-Tetraoxide Dihydrochloride) 2 n/a 50mg + + Edition 2017 Visit us at B-5
15 Products -oxides MM Imp. A (EP): 3-(10-Phenothiazin-10-yl)-,-dimethylpropan-1-amine -xide (Promazine ulphoxide) mg MM Imp. D (EP): (2R)-,-Dimethyl-1-(10phenothiazin-10-yl)propan-2-amine -xide (Promethazine ulphoxide) mg MM Promethazine ulphoxide -xide ydrochloride mg + MM Protionamide ulfoxide mg 2 MM Imp. C (EP): -[2-[[[5-[(Dimethylamino)- methyl]furan-2-yl]methyl]sulphinyl]ethyl]- '-methyl-2-nitroethene-1,1-diamine (Ranitidine ulphoxide) mg + MM ulforidazine 5-ulfone -xide (ulforidazine,5,5- Trioxide) mg + MM Imp. B (EP) as Besilate: 10-[2-[(2R)-1-Methylpiperidin-2-yl] ethyl]-2-(methylsulfinyl)-10-phenothiazine Besilate (Mesoridazine Besilate) mg MM Imp. C (EP): 10-[2-[(2R)-1-Methylpiperidin-2-yl]ethyl]-2- (methylsulfanyl)-10-phenothiazine 5-xide (Thioridazine 5- ulfoxide) mg MM Tiamulin ulfoxide n/a 100mg MM Triclabendazole ulfone mg Edition 2017 Visit us at B-6
16 Products -oxides MM Trifluoperazine ulfoxide mg MM Trifluoperazine ulfone n/a 100mg MM Trifluoperazine ulfoxide 1,4-Dioxide (Trifluoperazine 1,4,-Trioxide) mg + + MM Trifluoperazine ulfone 1,4-Dioxide (Trifluoperazine 1,4,,-Tetraoxide) n/a 100mg + + MM (Trifluoromethyl)-10-phenothiazine 5,5-Dioxide mg MM Triflupromazine ulfoxide mg MM Triflupromazine ulfone mg MM Triflupromazine ulfoxide -xide (Triflupromazine,- Dioxide) mg + MM Triflupromazine ulfone -xide ydrochloride (Triflupromazine,,-Trioxide ydrochloride) + n/a 100mg MM (Trifluoromethyl)-10-phenothiazine 5,5-Dioxide mg MM Trimeprazine ulphone (xomemazine) mg MM Trimeprazine ulphoxide ydrochloride n/a 100mg Edition 2017 Visit us at B-7
17 Products -oxides MM Trimeprazine ulfoxide -xide (Trimeprazine,-Dioxide) n/a 100mg + Edition 2017 Visit us at B-8
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