NZ575744A - Pharmaceutical compositions of clonazepam and methods of use thereof - Google Patents
Pharmaceutical compositions of clonazepam and methods of use thereofInfo
- Publication number
- NZ575744A NZ575744A NZ575744A NZ57574407A NZ575744A NZ 575744 A NZ575744 A NZ 575744A NZ 575744 A NZ575744 A NZ 575744A NZ 57574407 A NZ57574407 A NZ 57574407A NZ 575744 A NZ575744 A NZ 575744A
- Authority
- NZ
- New Zealand
- Prior art keywords
- clonazepam
- solvent
- composition
- drug
- mammal
- Prior art date
Links
- DGBIGWXXNGSACT-UHFFFAOYSA-N clonazepam Chemical group C12=CC([N+](=O)[O-])=CC=C2NC(=O)CN=C1C1=CC=CC=C1Cl DGBIGWXXNGSACT-UHFFFAOYSA-N 0.000 title claims abstract description 235
- 229960003120 clonazepam Drugs 0.000 title claims abstract description 232
- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 27
- 238000000034 method Methods 0.000 title claims description 34
- 239000002904 solvent Substances 0.000 claims abstract description 155
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims abstract description 87
- URAYPUMNDPQOKB-UHFFFAOYSA-N triacetin Chemical compound CC(=O)OCC(OC(C)=O)COC(C)=O URAYPUMNDPQOKB-UHFFFAOYSA-N 0.000 claims abstract description 59
- 241000124008 Mammalia Species 0.000 claims abstract description 42
- 239000000243 solution Substances 0.000 claims abstract description 40
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 36
- 239000002202 Polyethylene glycol Substances 0.000 claims abstract description 34
- 229920001223 polyethylene glycol Polymers 0.000 claims abstract description 34
- 235000013773 glyceryl triacetate Nutrition 0.000 claims abstract description 29
- 229960002622 triacetin Drugs 0.000 claims abstract description 29
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 claims abstract description 26
- 229920000642 polymer Polymers 0.000 claims abstract description 25
- 235000013772 propylene glycol Nutrition 0.000 claims abstract description 23
- 229940075557 diethylene glycol monoethyl ether Drugs 0.000 claims abstract description 19
- 239000012062 aqueous buffer Substances 0.000 claims abstract description 17
- 239000001089 [(2R)-oxolan-2-yl]methanol Substances 0.000 claims abstract description 14
- 210000004400 mucous membrane Anatomy 0.000 claims abstract description 14
- BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 claims abstract description 14
- 230000000149 penetrating effect Effects 0.000 claims abstract description 6
- 239000000203 mixture Substances 0.000 claims description 185
- 239000003814 drug Substances 0.000 claims description 101
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- 239000000872 buffer Substances 0.000 claims description 34
- 210000002850 nasal mucosa Anatomy 0.000 claims description 27
- 208000019901 Anxiety disease Diseases 0.000 claims description 18
- 239000003795 chemical substances by application Substances 0.000 claims description 18
- 239000003963 antioxidant agent Substances 0.000 claims description 17
- 235000006708 antioxidants Nutrition 0.000 claims description 17
- 210000004877 mucosa Anatomy 0.000 claims description 15
- 239000004094 surface-active agent Substances 0.000 claims description 14
- 206010071350 Seizure cluster Diseases 0.000 claims description 13
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- 239000003086 colorant Substances 0.000 claims description 7
- 239000006184 cosolvent Substances 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical group CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 claims description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 6
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 claims description 6
- 238000002156 mixing Methods 0.000 claims description 6
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- 239000000796 flavoring agent Substances 0.000 claims description 4
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims description 4
- 239000008363 phosphate buffer Substances 0.000 claims description 4
- 238000011287 therapeutic dose Methods 0.000 claims description 4
- 235000013355 food flavoring agent Nutrition 0.000 claims description 3
- 150000005846 sugar alcohols Polymers 0.000 claims description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims description 2
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 claims description 2
- ZGTMUACCHSMWAC-UHFFFAOYSA-L EDTA disodium salt (anhydrous) Chemical compound [Na+].[Na+].OC(=O)CN(CC([O-])=O)CCN(CC(O)=O)CC([O-])=O ZGTMUACCHSMWAC-UHFFFAOYSA-L 0.000 claims description 2
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims description 2
- 239000008351 acetate buffer Substances 0.000 claims description 2
- 239000007979 citrate buffer Substances 0.000 claims description 2
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 claims description 2
- 229940043279 diisopropylamine Drugs 0.000 claims description 2
- 229960001484 edetic acid Drugs 0.000 claims description 2
- 235000011167 hydrochloric acid Nutrition 0.000 claims description 2
- 239000004310 lactic acid Substances 0.000 claims description 2
- 235000014655 lactic acid Nutrition 0.000 claims description 2
- RTWNYYOXLSILQN-UHFFFAOYSA-N methanediamine Chemical compound NCN RTWNYYOXLSILQN-UHFFFAOYSA-N 0.000 claims description 2
- 229940037001 sodium edetate Drugs 0.000 claims description 2
- 235000011121 sodium hydroxide Nutrition 0.000 claims description 2
- 239000011975 tartaric acid Substances 0.000 claims description 2
- 235000002906 tartaric acid Nutrition 0.000 claims description 2
- 229940079593 drug Drugs 0.000 description 98
- 229940049706 benzodiazepine Drugs 0.000 description 64
- 238000009472 formulation Methods 0.000 description 64
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 55
- 150000001557 benzodiazepines Chemical class 0.000 description 31
- 238000011282 treatment Methods 0.000 description 31
- SVUOLADPCWQTTE-UHFFFAOYSA-N 1h-1,2-benzodiazepine Chemical compound N1N=CC=CC2=CC=CC=C12 SVUOLADPCWQTTE-UHFFFAOYSA-N 0.000 description 30
- 230000000694 effects Effects 0.000 description 24
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 22
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- 239000007921 spray Substances 0.000 description 21
- CTPDSKVQLSDPLC-UHFFFAOYSA-N 2-(oxolan-2-ylmethoxy)ethanol Chemical compound OCCOCC1CCCO1 CTPDSKVQLSDPLC-UHFFFAOYSA-N 0.000 description 20
- 239000001087 glyceryl triacetate Substances 0.000 description 19
- 241001494479 Pecora Species 0.000 description 17
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 16
- 239000012071 phase Substances 0.000 description 16
- -1 hypnotic Substances 0.000 description 15
- 238000010521 absorption reaction Methods 0.000 description 13
- AAOVKJBEBIDNHE-UHFFFAOYSA-N diazepam Chemical compound N=1CC(=O)N(C)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 AAOVKJBEBIDNHE-UHFFFAOYSA-N 0.000 description 13
- 239000000843 powder Substances 0.000 description 13
- 239000013543 active substance Substances 0.000 description 12
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 12
- 239000012530 fluid Substances 0.000 description 12
- 241000282414 Homo sapiens Species 0.000 description 11
- 230000015556 catabolic process Effects 0.000 description 10
- 238000006731 degradation reaction Methods 0.000 description 10
- 229960003529 diazepam Drugs 0.000 description 10
- 239000002552 dosage form Substances 0.000 description 10
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- 230000036470 plasma concentration Effects 0.000 description 10
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- 238000004128 high performance liquid chromatography Methods 0.000 description 9
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- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 9
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
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- DIWRORZWFLOCLC-HNNXBMFYSA-N (3s)-7-chloro-5-(2-chlorophenyl)-3-hydroxy-1,3-dihydro-1,4-benzodiazepin-2-one Chemical compound N([C@H](C(NC1=CC=C(Cl)C=C11)=O)O)=C1C1=CC=CC=C1Cl DIWRORZWFLOCLC-HNNXBMFYSA-N 0.000 description 5
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- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
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- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 4
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- MQTOSJVFKKJCRP-BICOPXKESA-N azithromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)N(C)C[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 MQTOSJVFKKJCRP-BICOPXKESA-N 0.000 description 4
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- LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 4
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- DDLIGBOFAVUZHB-UHFFFAOYSA-N midazolam Chemical compound C12=CC(Cl)=CC=C2N2C(C)=NC=C2CN=C1C1=CC=CC=C1F DDLIGBOFAVUZHB-UHFFFAOYSA-N 0.000 description 4
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- CZBZUDVBLSSABA-UHFFFAOYSA-N butylated hydroxyanisole Chemical compound COC1=CC=C(O)C(C(C)(C)C)=C1.COC1=CC=C(O)C=C1C(C)(C)C CZBZUDVBLSSABA-UHFFFAOYSA-N 0.000 description 3
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- ADIMAYPTOBDMTL-UHFFFAOYSA-N oxazepam Chemical compound C12=CC(Cl)=CC=C2NC(=O)C(O)N=C1C1=CC=CC=C1 ADIMAYPTOBDMTL-UHFFFAOYSA-N 0.000 description 2
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2007
- 2007-08-14 TW TW096130010A patent/TW200824693A/zh unknown
- 2007-08-23 PE PE2007001144A patent/PE20081361A1/es not_active Application Discontinuation
- 2007-08-27 CA CA002662197A patent/CA2662197A1/en not_active Abandoned
- 2007-08-27 UY UY30561A patent/UY30561A1/es unknown
- 2007-08-27 BR BRPI0714907-7A patent/BRPI0714907A2/pt not_active IP Right Cessation
- 2007-08-27 US US11/897,028 patent/US8609651B2/en not_active Expired - Fee Related
- 2007-08-27 CN CN2007800399467A patent/CN101528261B/zh not_active Expired - Fee Related
- 2007-08-27 EP EP07837400A patent/EP2068933A2/en not_active Withdrawn
- 2007-08-27 JP JP2009526683A patent/JP2010502614A/ja not_active Ceased
- 2007-08-27 MX MX2009002310A patent/MX2009002310A/es not_active Application Discontinuation
- 2007-08-27 US US11/897,002 patent/US8716279B2/en not_active Expired - Fee Related
- 2007-08-27 NZ NZ575744A patent/NZ575744A/en not_active IP Right Cessation
- 2007-08-27 WO PCT/US2007/018877 patent/WO2008027357A2/en not_active Ceased
- 2007-08-27 WO PCT/US2007/018942 patent/WO2008027395A2/en not_active Ceased
- 2007-08-27 NZ NZ595388A patent/NZ595388A/en not_active IP Right Cessation
- 2007-08-27 EP EP07811570A patent/EP2056877A2/en not_active Withdrawn
- 2007-08-27 JP JP2009526675A patent/JP2010502612A/ja not_active Ceased
- 2007-08-27 KR KR1020097006303A patent/KR20090043603A/ko not_active Ceased
- 2007-08-27 AU AU2007290589A patent/AU2007290589B2/en not_active Ceased
- 2007-08-28 AR ARP070103802A patent/AR062556A1/es not_active Application Discontinuation
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2009
- 2009-02-26 IL IL197275A patent/IL197275A0/en unknown
- 2009-03-23 NO NO20091211A patent/NO20091211L/no not_active Application Discontinuation
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Also Published As
| Publication number | Publication date |
|---|---|
| JP2010502612A (ja) | 2010-01-28 |
| JP2010502614A (ja) | 2010-01-28 |
| EP2056877A2 (en) | 2009-05-13 |
| BRPI0714907A2 (pt) | 2014-08-19 |
| US20080070904A1 (en) | 2008-03-20 |
| WO2008027357A2 (en) | 2008-03-06 |
| IL197275A0 (en) | 2009-12-24 |
| US20080076761A1 (en) | 2008-03-27 |
| EP2068933A2 (en) | 2009-06-17 |
| WO2008027357A9 (en) | 2009-04-30 |
| CN101528261A (zh) | 2009-09-09 |
| CN101528261B (zh) | 2012-07-18 |
| KR20090043603A (ko) | 2009-05-06 |
| AU2007290589B2 (en) | 2012-04-05 |
| NO20091211L (no) | 2009-05-27 |
| WO2008027395A2 (en) | 2008-03-06 |
| AR062556A1 (es) | 2008-11-19 |
| TW200824693A (en) | 2008-06-16 |
| PE20081361A1 (es) | 2008-11-06 |
| CA2662197A1 (en) | 2008-03-06 |
| US8716279B2 (en) | 2014-05-06 |
| NZ595388A (en) | 2011-12-22 |
| US8609651B2 (en) | 2013-12-17 |
| MX2009002310A (es) | 2009-09-21 |
| WO2008027395A3 (en) | 2008-04-17 |
| UY30561A1 (es) | 2008-03-31 |
| AU2007290589A1 (en) | 2008-03-06 |
| WO2008027357A3 (en) | 2008-04-17 |
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