CA2723470C

CA2723470C - Nasal administration of benzodiazepines

Nasal administration of benzodiazepines Download PDF

Info

Publication number: CA2723470C
Authority: CA; Canada
Prior art keywords: ammonium chloride; benzodiazepine; bromide; chloride; seizure
Prior art date: 2007-05-07
Legal status : Expired - Fee Related

Application number

CA2723470A

Other languages

English (en)

French (fr)

Other versions

CA2723470A1 (en

Inventor

Steve Cartt

David Medeiros

Current Assignee

Hale BioPharma Ventures LLC

Original Assignee

Hale BioPharma Ventures LLC

Priority date

2007-05-07

Filing date

2008-05-07

Publication date

2013-12-03

2008-05-07 Application filed by Hale BioPharma Ventures LLC filed Critical Hale BioPharma Ventures LLC

2008-11-13 Publication of CA2723470A1 publication Critical patent/CA2723470A1/en

2013-12-03 Application granted granted Critical

2013-12-03 Publication of CA2723470C publication Critical patent/CA2723470C/en

Status Expired - Fee Related legal-status Critical Current

2028-05-07 Anticipated expiration legal-status Critical

Links

229940049706 benzodiazepine Drugs 0.000 title claims abstract description 405
150000001557 benzodiazepines Chemical class 0.000 title abstract description 36
239000000203 mixture Substances 0.000 claims abstract description 376
239000003814 drug Substances 0.000 claims abstract description 231
229960003529 diazepam Drugs 0.000 claims abstract description 131
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 claims abstract description 131
SVUOLADPCWQTTE-UHFFFAOYSA-N 1h-1,2-benzodiazepine Chemical compound N1N=CC=CC2=CC=CC=C12 SVUOLADPCWQTTE-UHFFFAOYSA-N 0.000 claims description 372
239000002245 particle Substances 0.000 claims description 333
-1 clorazepam Chemical compound 0.000 claims description 198
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 claims description 93
229960004391 lorazepam Drugs 0.000 claims description 93
XBWAZCLHZCFCGK-UHFFFAOYSA-N 7-chloro-1-methyl-5-phenyl-3,4-dihydro-2h-1,4-benzodiazepin-1-ium;chloride Chemical compound [Cl-].C12=CC(Cl)=CC=C2[NH+](C)CCN=C1C1=CC=CC=C1 XBWAZCLHZCFCGK-UHFFFAOYSA-N 0.000 claims description 92
229960002225 medazepam Drugs 0.000 claims description 92
DDLIGBOFAVUZHB-UHFFFAOYSA-N midazolam Chemical compound C12=CC(Cl)=CC=C2N2C(C)=NC=C2CN=C1C1=CC=CC=C1F DDLIGBOFAVUZHB-UHFFFAOYSA-N 0.000 claims description 68
229960003793 midazolam Drugs 0.000 claims description 68
150000003839 salts Chemical class 0.000 claims description 68
239000006185 dispersion Substances 0.000 claims description 63
239000000443 aerosol Substances 0.000 claims description 53
229960004538 alprazolam Drugs 0.000 claims description 50
VREFGVBLTWBCJP-UHFFFAOYSA-N alprazolam Chemical compound C12=CC(Cl)=CC=C2N2C(C)=NN=C2CN=C1C1=CC=CC=C1 VREFGVBLTWBCJP-UHFFFAOYSA-N 0.000 claims description 50
SEQDDYPDSLOBDC-UHFFFAOYSA-N Temazepam Chemical compound N=1C(O)C(=O)N(C)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 SEQDDYPDSLOBDC-UHFFFAOYSA-N 0.000 claims description 49
229960003188 temazepam Drugs 0.000 claims description 49
229960003528 flurazepam Drugs 0.000 claims description 47
SAADBVWGJQAEFS-UHFFFAOYSA-N flurazepam Chemical compound N=1CC(=O)N(CCN(CC)CC)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1F SAADBVWGJQAEFS-UHFFFAOYSA-N 0.000 claims description 47
230000001225 therapeutic effect Effects 0.000 claims description 41
230000001773 anti-convulsant effect Effects 0.000 claims description 40
125000002091 cationic group Chemical group 0.000 claims description 35
150000001875 compounds Chemical class 0.000 claims description 35
ANUCDXCTICZJRH-UHFFFAOYSA-N mexazolam Chemical compound C=1C=C(Cl)C=C2C=1NC(=O)CN1C(C)COC21C1=CC=CC=C1Cl ANUCDXCTICZJRH-UHFFFAOYSA-N 0.000 claims description 35
229950000412 mexazolam Drugs 0.000 claims description 35
230000001624 sedative effect Effects 0.000 claims description 34
229960002640 nordazepam Drugs 0.000 claims description 33
AKPLHCDWDRPJGD-UHFFFAOYSA-N nordazepam Chemical compound C12=CC(Cl)=CC=C2NC(=O)CN=C1C1=CC=CC=C1 AKPLHCDWDRPJGD-UHFFFAOYSA-N 0.000 claims description 33
244000060011 Cocos nucifera Species 0.000 claims description 31
235000013162 Cocos nucifera Nutrition 0.000 claims description 31
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims description 30
CADWTSSKOVRVJC-UHFFFAOYSA-N benzyl(dimethyl)azanium;chloride Chemical compound [Cl-].C[NH+](C)CC1=CC=CC=C1 CADWTSSKOVRVJC-UHFFFAOYSA-N 0.000 claims description 30
230000002040 relaxant effect Effects 0.000 claims description 30
230000003109 amnesic effect Effects 0.000 claims description 28
230000000949 anxiolytic effect Effects 0.000 claims description 28
HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 claims description 28
229920000642 polymer Polymers 0.000 claims description 28
235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 claims description 26
229920003088 hydroxypropyl methyl cellulose Polymers 0.000 claims description 26
239000001866 hydroxypropyl methyl cellulose Substances 0.000 claims description 26
239000003158 myorelaxant agent Substances 0.000 claims description 26
210000002027 skeletal muscle Anatomy 0.000 claims description 26
229920001282 polysaccharide Polymers 0.000 claims description 22
239000005017 polysaccharide Substances 0.000 claims description 22
230000002902 bimodal effect Effects 0.000 claims description 21
238000009826 distribution Methods 0.000 claims description 21
229920001661 Chitosan Polymers 0.000 claims description 20
DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 claims description 20
229960000686 benzalkonium chloride Drugs 0.000 claims description 20
229940107161 cholesterol Drugs 0.000 claims description 19
239000008194 pharmaceutical composition Substances 0.000 claims description 19
229960003120 clonazepam Drugs 0.000 claims description 18
DGBIGWXXNGSACT-UHFFFAOYSA-N clonazepam Chemical compound C12=CC([N+](=O)[O-])=CC=C2NC(=O)CN=C1C1=CC=CC=C1Cl DGBIGWXXNGSACT-UHFFFAOYSA-N 0.000 claims description 18
238000002360 preparation method Methods 0.000 claims description 18
UMSGKTJDUHERQW-UHFFFAOYSA-N Brotizolam Chemical compound C1=2C=C(Br)SC=2N2C(C)=NN=C2CN=C1C1=CC=CC=C1Cl UMSGKTJDUHERQW-UHFFFAOYSA-N 0.000 claims description 17
WYCLKVQLVUQKNZ-UHFFFAOYSA-N Halazepam Chemical compound N=1CC(=O)N(CC(F)(F)F)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 WYCLKVQLVUQKNZ-UHFFFAOYSA-N 0.000 claims description 17
MWQCHHACWWAQLJ-UHFFFAOYSA-N Prazepam Chemical compound O=C1CN=C(C=2C=CC=CC=2)C2=CC(Cl)=CC=C2N1CC1CC1 MWQCHHACWWAQLJ-UHFFFAOYSA-N 0.000 claims description 17
IKMPWMZBZSAONZ-UHFFFAOYSA-N Quazepam Chemical compound FC1=CC=CC=C1C1=NCC(=S)N(CC(F)(F)F)C2=CC=C(Cl)C=C12 IKMPWMZBZSAONZ-UHFFFAOYSA-N 0.000 claims description 17
JBIROUFYLSSYDX-UHFFFAOYSA-M benzododecinium chloride Chemical compound [Cl-].CCCCCCCCCCCC[N+](C)(C)CC1=CC=CC=C1 JBIROUFYLSSYDX-UHFFFAOYSA-M 0.000 claims description 17
229960003051 brotizolam Drugs 0.000 claims description 17
229960001403 clobazam Drugs 0.000 claims description 17
CXOXHMZGEKVPMT-UHFFFAOYSA-N clobazam Chemical compound O=C1CC(=O)N(C)C2=CC=C(Cl)C=C2N1C1=CC=CC=C1 CXOXHMZGEKVPMT-UHFFFAOYSA-N 0.000 claims description 17
229960004381 flumazenil Drugs 0.000 claims description 17
OFBIFZUFASYYRE-UHFFFAOYSA-N flumazenil Chemical compound C1N(C)C(=O)C2=CC(F)=CC=C2N2C=NC(C(=O)OCC)=C21 OFBIFZUFASYYRE-UHFFFAOYSA-N 0.000 claims description 17
229960002158 halazepam Drugs 0.000 claims description 17
UTEFBSAVJNEPTR-RGEXLXHISA-N loprazolam Chemical compound C1CN(C)CCN1\C=C/1C(=O)N2C3=CC=C([N+]([O-])=O)C=C3C(C=3C(=CC=CC=3)Cl)=NCC2=N\1 UTEFBSAVJNEPTR-RGEXLXHISA-N 0.000 claims description 17
229960003019 loprazolam Drugs 0.000 claims description 17
KJONHKAYOJNZEC-UHFFFAOYSA-N nitrazepam Chemical compound C12=CC([N+](=O)[O-])=CC=C2NC(=O)CN=C1C1=CC=CC=C1 KJONHKAYOJNZEC-UHFFFAOYSA-N 0.000 claims description 17
229960001454 nitrazepam Drugs 0.000 claims description 17
229960004856 prazepam Drugs 0.000 claims description 17
229960001964 quazepam Drugs 0.000 claims description 17
JOFWLTCLBGQGBO-UHFFFAOYSA-N triazolam Chemical compound C12=CC(Cl)=CC=C2N2C(C)=NN=C2CN=C1C1=CC=CC=C1Cl JOFWLTCLBGQGBO-UHFFFAOYSA-N 0.000 claims description 17
229960003386 triazolam Drugs 0.000 claims description 17
229960004782 chlordiazepoxide Drugs 0.000 claims description 16
ANTSCNMPPGJYLG-UHFFFAOYSA-N chlordiazepoxide Chemical compound O=N=1CC(NC)=NC2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 ANTSCNMPPGJYLG-UHFFFAOYSA-N 0.000 claims description 16
229960004535 oxazepam Drugs 0.000 claims description 16
ADIMAYPTOBDMTL-UHFFFAOYSA-N oxazepam Chemical compound C12=CC(Cl)=CC=C2NC(=O)C(O)N=C1C1=CC=CC=C1 ADIMAYPTOBDMTL-UHFFFAOYSA-N 0.000 claims description 16
235000019270 ammonium chloride Nutrition 0.000 claims description 15
LNAZSHAWQACDHT-XIYTZBAFSA-N (2r,3r,4s,5r,6s)-4,5-dimethoxy-2-(methoxymethyl)-3-[(2s,3r,4s,5r,6r)-3,4,5-trimethoxy-6-(methoxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6r)-4,5,6-trimethoxy-2-(methoxymethyl)oxan-3-yl]oxyoxane Chemical compound CO[C@@H]1[C@@H](OC)[C@H](OC)[C@@H](COC)O[C@H]1O[C@H]1[C@H](OC)[C@@H](OC)[C@H](O[C@H]2[C@@H]([C@@H](OC)[C@H](OC)O[C@@H]2COC)OC)O[C@@H]1COC LNAZSHAWQACDHT-XIYTZBAFSA-N 0.000 claims description 14
VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 claims description 14
229920003171 Poly (ethylene oxide) Polymers 0.000 claims description 14
235000012000 cholesterol Nutrition 0.000 claims description 14
229920000609 methyl cellulose Polymers 0.000 claims description 14
239000001923 methylcellulose Substances 0.000 claims description 14
229960002900 methylcellulose Drugs 0.000 claims description 14
235000010981 methylcellulose Nutrition 0.000 claims description 14
150000001412 amines Chemical class 0.000 claims description 13
229920000036 polyvinylpyrrolidone Polymers 0.000 claims description 13
235000013855 polyvinylpyrrolidone Nutrition 0.000 claims description 13
150000003973 alkyl amines Chemical class 0.000 claims description 12
239000007900 aqueous suspension Substances 0.000 claims description 12
DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 claims description 11
229960003943 hypromellose Drugs 0.000 claims description 11
AISMNBXOJRHCIA-UHFFFAOYSA-N trimethylazanium;bromide Chemical compound Br.CN(C)C AISMNBXOJRHCIA-UHFFFAOYSA-N 0.000 claims description 11
235000014113 dietary fatty acids Nutrition 0.000 claims description 10
DDXLVDQZPFLQMZ-UHFFFAOYSA-M dodecyl(trimethyl)azanium;chloride Chemical compound [Cl-].CCCCCCCCCCCC[N+](C)(C)C DDXLVDQZPFLQMZ-UHFFFAOYSA-M 0.000 claims description 10
239000000194 fatty acid Substances 0.000 claims description 10
229930195729 fatty acid Natural products 0.000 claims description 10
235000019333 sodium laurylsulphate Nutrition 0.000 claims description 10
239000001267 polyvinylpyrrolidone Substances 0.000 claims description 9
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 8
229920002153 Hydroxypropyl cellulose Polymers 0.000 claims description 8
WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims description 8
239000004372 Polyvinyl alcohol Substances 0.000 claims description 8
235000021355 Stearic acid Nutrition 0.000 claims description 8
239000005018 casein Substances 0.000 claims description 8
BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 claims description 8
235000021240 caseins Nutrition 0.000 claims description 8
235000010977 hydroxypropyl cellulose Nutrition 0.000 claims description 8
239000001863 hydroxypropyl cellulose Substances 0.000 claims description 8
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims description 8
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 claims description 8
229920001987 poloxamine Polymers 0.000 claims description 8
229920001223 polyethylene glycol Polymers 0.000 claims description 8
229920002451 polyvinyl alcohol Polymers 0.000 claims description 8
APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 claims description 8
238000005507 spraying Methods 0.000 claims description 8
239000008117 stearic acid Substances 0.000 claims description 8
229960004274 stearic acid Drugs 0.000 claims description 8
JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical class OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 claims description 7
108010010803 Gelatin Proteins 0.000 claims description 7
229910019142 PO4 Inorganic materials 0.000 claims description 7
239000004721 Polyphenylene oxide Substances 0.000 claims description 7
229920001214 Polysorbate 60 Polymers 0.000 claims description 7
229920002678 cellulose Polymers 0.000 claims description 7
239000001913 cellulose Substances 0.000 claims description 7
229940082500 cetostearyl alcohol Drugs 0.000 claims description 7
229940014259 gelatin Drugs 0.000 claims description 7
239000008273 gelatin Substances 0.000 claims description 7
229920000159 gelatin Polymers 0.000 claims description 7
235000019322 gelatine Nutrition 0.000 claims description 7
235000011852 gelatine desserts Nutrition 0.000 claims description 7
YQEMORVAKMFKLG-UHFFFAOYSA-N glycerine monostearate Natural products CCCCCCCCCCCCCCCCCC(=O)OC(CO)CO YQEMORVAKMFKLG-UHFFFAOYSA-N 0.000 claims description 7
SVUQHVRAGMNPLW-UHFFFAOYSA-N glycerol monostearate Natural products CCCCCCCCCCCCCCCCC(=O)OCC(O)CO SVUQHVRAGMNPLW-UHFFFAOYSA-N 0.000 claims description 7
GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 claims description 7
235000021317 phosphate Nutrition 0.000 claims description 7
229920001983 poloxamer Polymers 0.000 claims description 7
229920000570 polyether Polymers 0.000 claims description 7
OULAJFUGPPVRBK-UHFFFAOYSA-N tetratriacontyl alcohol Natural products CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCO OULAJFUGPPVRBK-UHFFFAOYSA-N 0.000 claims description 7
229920001664 tyloxapol Polymers 0.000 claims description 7
MDYZKJNTKZIUSK-UHFFFAOYSA-N tyloxapol Chemical compound O=C.C1CO1.CC(C)(C)CC(C)(C)C1=CC=C(O)C=C1 MDYZKJNTKZIUSK-UHFFFAOYSA-N 0.000 claims description 7
229960004224 tyloxapol Drugs 0.000 claims description 7
QAQSNXHKHKONNS-UHFFFAOYSA-N 1-ethyl-2-hydroxy-4-methyl-6-oxopyridine-3-carboxamide Chemical compound CCN1C(O)=C(C(N)=O)C(C)=CC1=O QAQSNXHKHKONNS-UHFFFAOYSA-N 0.000 claims description 6
IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 claims description 6
KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical compound C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 claims description 6
244000215068 Acacia senegal Species 0.000 claims description 6
235000006491 Acacia senegal Nutrition 0.000 claims description 6
241000416162 Astragalus gummifer Species 0.000 claims description 6
CXRFDZFCGOPDTD-UHFFFAOYSA-M Cetrimide Chemical compound [Br-].CCCCCCCCCCCCCC[N+](C)(C)C CXRFDZFCGOPDTD-UHFFFAOYSA-M 0.000 claims description 6
244000303965 Cyamopsis psoralioides Species 0.000 claims description 6
229920002307 Dextran Polymers 0.000 claims description 6
229920000084 Gum arabic Polymers 0.000 claims description 6
239000004354 Hydroxyethyl cellulose Substances 0.000 claims description 6
229920000663 Hydroxyethyl cellulose Polymers 0.000 claims description 6
108010014251 Muramidase Proteins 0.000 claims description 6
102000016943 Muramidase Human genes 0.000 claims description 6
108010062010 N-Acetylmuramoyl-L-alanine Amidase Proteins 0.000 claims description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 6
VBIIFPGSPJYLRR-UHFFFAOYSA-M Stearyltrimethylammonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCC[N+](C)(C)C VBIIFPGSPJYLRR-UHFFFAOYSA-M 0.000 claims description 6
229920001615 Tragacanth Polymers 0.000 claims description 6
GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 claims description 6
FOLJTMYCYXSPFQ-CJKAUBRRSA-N [(2r,3s,4s,5r,6r)-6-[(2s,3s,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)-2-(octadecanoyloxymethyl)oxolan-2-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methyl octadecanoate Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](COC(=O)CCCCCCCCCCCCCCCCC)O[C@@H]1O[C@@]1(COC(=O)CCCCCCCCCCCCCCCCC)[C@@H](O)[C@H](O)[C@@H](CO)O1 FOLJTMYCYXSPFQ-CJKAUBRRSA-N 0.000 claims description 6
235000010489 acacia gum Nutrition 0.000 claims description 6
150000003926 acrylamides Chemical group 0.000 claims description 6
235000010443 alginic acid Nutrition 0.000 claims description 6
229920000615 alginic acid Polymers 0.000 claims description 6
125000002877 alkyl aryl group Chemical group 0.000 claims description 6
125000006177 alkyl benzyl group Chemical group 0.000 claims description 6
150000005215 alkyl ethers Chemical class 0.000 claims description 6
SNAAJJQQZSMGQD-UHFFFAOYSA-N aluminum magnesium Chemical compound [Mg].[Al] SNAAJJQQZSMGQD-UHFFFAOYSA-N 0.000 claims description 6
150000003868 ammonium compounds Chemical class 0.000 claims description 6
UUZYBYIOAZTMGC-UHFFFAOYSA-M benzyl(trimethyl)azanium;bromide Chemical compound [Br-].C[N+](C)(C)CC1=CC=CC=C1 UUZYBYIOAZTMGC-UHFFFAOYSA-M 0.000 claims description 6
WMLFGKCFDKMAKB-UHFFFAOYSA-M benzyl-diethyl-tetradecylazanium;chloride Chemical compound [Cl-].CCCCCCCCCCCCCC[N+](CC)(CC)CC1=CC=CC=C1 WMLFGKCFDKMAKB-UHFFFAOYSA-M 0.000 claims description 6
CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 claims description 6
235000013539 calcium stearate Nutrition 0.000 claims description 6
239000008116 calcium stearate Substances 0.000 claims description 6
229940078456 calcium stearate Drugs 0.000 claims description 6
229920003123 carboxymethyl cellulose sodium Polymers 0.000 claims description 6
229940084030 carboxymethylcellulose calcium Drugs 0.000 claims description 6
229940063834 carboxymethylcellulose sodium Drugs 0.000 claims description 6
239000004359 castor oil Substances 0.000 claims description 6
235000019438 castor oil Nutrition 0.000 claims description 6
YMKDRGPMQRFJGP-UHFFFAOYSA-M cetylpyridinium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCC[N+]1=CC=CC=C1 YMKDRGPMQRFJGP-UHFFFAOYSA-M 0.000 claims description 6
229960001927 cetylpyridinium chloride Drugs 0.000 claims description 6
229940075614 colloidal silicon dioxide Drugs 0.000 claims description 6
PLMFYJJFUUUCRZ-UHFFFAOYSA-M decyltrimethylammonium bromide Chemical compound [Br-].CCCCCCCCCC[N+](C)(C)C PLMFYJJFUUUCRZ-UHFFFAOYSA-M 0.000 claims description 6
125000005265 dialkylamine group Chemical group 0.000 claims description 6
IQDGSYLLQPDQDV-UHFFFAOYSA-N dimethylazanium;chloride Chemical class Cl.CNC IQDGSYLLQPDQDV-UHFFFAOYSA-N 0.000 claims description 6
229960000878 docusate sodium Drugs 0.000 claims description 6
VVNBOKHXEBSBQJ-UHFFFAOYSA-M dodecyl(triethyl)azanium;bromide Chemical compound [Br-].CCCCCCCCCCCC[N+](CC)(CC)CC VVNBOKHXEBSBQJ-UHFFFAOYSA-M 0.000 claims description 6
HBRNMIYLJIXXEE-UHFFFAOYSA-N dodecylazanium;acetate Chemical compound CC(O)=O.CCCCCCCCCCCCN HBRNMIYLJIXXEE-UHFFFAOYSA-N 0.000 claims description 6
239000008387 emulsifying waxe Substances 0.000 claims description 6
ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 claims description 6
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125000001424 substituent group Chemical group 0.000 description 1
125000000547 substituted alkyl group Chemical group 0.000 description 1
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YNDXUCZADRHECN-JNQJZLCISA-N triamcinolone acetonide Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H]3OC(C)(C)O[C@@]3(C(=O)CO)[C@@]1(C)C[C@@H]2O YNDXUCZADRHECN-JNQJZLCISA-N 0.000 description 1
150000003918 triazines Chemical class 0.000 description 1
CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
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IRYJRGCIQBGHIV-UHFFFAOYSA-N trimethadione Chemical compound CN1C(=O)OC(C)(C)C1=O IRYJRGCIQBGHIV-UHFFFAOYSA-N 0.000 description 1
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MSRILKIQRXUYCT-UHFFFAOYSA-M valproate semisodium Chemical compound [Na+].CCCC(C(O)=O)CCC.CCCC(C([O-])=O)CCC MSRILKIQRXUYCT-UHFFFAOYSA-M 0.000 description 1
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PJDFLNIOAUIZSL-UHFFFAOYSA-N vigabatrin Chemical compound C=CC(N)CCC(O)=O PJDFLNIOAUIZSL-UHFFFAOYSA-N 0.000 description 1
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UBQNRHZMVUUOMG-UHFFFAOYSA-N zonisamide Chemical compound C1=CC=C2C(CS(=O)(=O)N)=NOC2=C1 UBQNRHZMVUUOMG-UHFFFAOYSA-N 0.000 description 1