NZ198533A - Soft gelatin capsules containing prostaglandins - Google Patents
Soft gelatin capsules containing prostaglandinsInfo
- Publication number
- NZ198533A NZ198533A NZ198533A NZ19853381A NZ198533A NZ 198533 A NZ198533 A NZ 198533A NZ 198533 A NZ198533 A NZ 198533A NZ 19853381 A NZ19853381 A NZ 19853381A NZ 198533 A NZ198533 A NZ 198533A
- Authority
- NZ
- New Zealand
- Prior art keywords
- composition according
- prostaglandin
- hydrogen
- oxoprosta
- polyethylene glycol
- Prior art date
Links
- 150000003180 prostaglandins Chemical class 0.000 title claims abstract description 32
- 239000007903 gelatin capsule Substances 0.000 title claims abstract description 14
- 229940094443 oxytocics prostaglandins Drugs 0.000 title description 14
- 239000000203 mixture Substances 0.000 claims abstract description 56
- 239000011786 L-ascorbyl-6-palmitate Substances 0.000 claims abstract description 24
- QAQJMLQRFWZOBN-LAUBAEHRSA-N L-ascorbyl-6-palmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](O)[C@H]1OC(=O)C(O)=C1O QAQJMLQRFWZOBN-LAUBAEHRSA-N 0.000 claims abstract description 23
- 235000010385 ascorbyl palmitate Nutrition 0.000 claims abstract description 23
- 229920001223 polyethylene glycol Polymers 0.000 claims abstract description 16
- 235000014113 dietary fatty acids Nutrition 0.000 claims abstract description 5
- 239000000194 fatty acid Substances 0.000 claims abstract description 5
- 229930195729 fatty acid Natural products 0.000 claims abstract description 5
- 239000002202 Polyethylene glycol Substances 0.000 claims abstract description 4
- 150000004665 fatty acids Chemical class 0.000 claims abstract description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 3
- 229920000136 polysorbate Polymers 0.000 claims abstract description 3
- 239000002253 acid Substances 0.000 claims description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 239000002904 solvent Substances 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 229920002565 Polyethylene Glycol 400 Polymers 0.000 claims description 6
- 229920001214 Polysorbate 60 Polymers 0.000 claims description 6
- 229940068918 polyethylene glycol 400 Drugs 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 4
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 229920001030 Polyethylene Glycol 4000 Polymers 0.000 claims description 2
- HVUMOYIDDBPOLL-XWVZOOPGSA-N Sorbitan monostearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O HVUMOYIDDBPOLL-XWVZOOPGSA-N 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- HVFSJXUIRWUHRG-UHFFFAOYSA-N oic acid Natural products C1CC2C3CC=C4CC(OC5C(C(O)C(O)C(CO)O5)O)CC(O)C4(C)C3CCC2(C)C1C(C)C(O)CC(C)=C(C)C(=O)OC1OC(COC(C)=O)C(O)C(O)C1OC(C(C1O)O)OC(COC(C)=O)C1OC1OC(CO)C(O)C(O)C1O HVFSJXUIRWUHRG-UHFFFAOYSA-N 0.000 claims description 2
- NWGKJDSIEKMTRX-AAZCQSIUSA-N Sorbitan monooleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O NWGKJDSIEKMTRX-AAZCQSIUSA-N 0.000 claims 1
- IYFATESGLOUGBX-YVNJGZBMSA-N Sorbitan monopalmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O IYFATESGLOUGBX-YVNJGZBMSA-N 0.000 claims 1
- 229940057838 polyethylene glycol 4000 Drugs 0.000 claims 1
- 229950004959 sorbitan oleate Drugs 0.000 claims 1
- 229950003429 sorbitan palmitate Drugs 0.000 claims 1
- 229950011392 sorbitan stearate Drugs 0.000 claims 1
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 abstract description 6
- 239000002552 dosage form Substances 0.000 abstract description 3
- 229960005070 ascorbic acid Drugs 0.000 abstract description 2
- 235000000072 L-ascorbyl-6-palmitate Nutrition 0.000 abstract 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 26
- 235000019282 butylated hydroxyanisole Nutrition 0.000 description 25
- 239000004255 Butylated hydroxyanisole Substances 0.000 description 23
- 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 23
- 229940043253 butylated hydroxyanisole Drugs 0.000 description 23
- 239000002775 capsule Substances 0.000 description 17
- 238000009472 formulation Methods 0.000 description 17
- 239000007788 liquid Substances 0.000 description 15
- 229910052757 nitrogen Inorganic materials 0.000 description 13
- 239000003381 stabilizer Substances 0.000 description 9
- 239000004480 active ingredient Substances 0.000 description 8
- 239000004322 Butylated hydroxytoluene Substances 0.000 description 7
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 7
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 7
- 229940095259 butylated hydroxytoluene Drugs 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 6
- 238000000240 pulsed field-gradient spin echo nuclear magnetic resonance spectroscopy Methods 0.000 description 6
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 6
- 241000700159 Rattus Species 0.000 description 5
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 5
- 229940068968 polysorbate 80 Drugs 0.000 description 5
- ZTHYODDOHIVTJV-UHFFFAOYSA-N Propyl gallate Chemical compound CCCOC(=O)C1=CC(O)=C(O)C(O)=C1 ZTHYODDOHIVTJV-UHFFFAOYSA-N 0.000 description 4
- XEYBRNLFEZDVAW-ARSRFYASSA-N dinoprostone Chemical compound CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1C\C=C/CCCC(O)=O XEYBRNLFEZDVAW-ARSRFYASSA-N 0.000 description 4
- 229960002986 dinoprostone Drugs 0.000 description 4
- 239000004615 ingredient Substances 0.000 description 4
- 230000005764 inhibitory process Effects 0.000 description 4
- 229940068196 placebo Drugs 0.000 description 4
- 239000000902 placebo Substances 0.000 description 4
- XEYBRNLFEZDVAW-UHFFFAOYSA-N prostaglandin E2 Natural products CCCCCC(O)C=CC1C(O)CC(=O)C1CC=CCCCC(O)=O XEYBRNLFEZDVAW-UHFFFAOYSA-N 0.000 description 4
- 230000001262 anti-secretory effect Effects 0.000 description 3
- 210000004051 gastric juice Anatomy 0.000 description 3
- 238000001802 infusion Methods 0.000 description 3
- 229920000053 polysorbate 80 Polymers 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- 241000238367 Mya arenaria Species 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- BGNXCDMCOKJUMV-UHFFFAOYSA-N Tert-Butylhydroquinone Chemical compound CC(C)(C)C1=CC(O)=CC=C1O BGNXCDMCOKJUMV-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 235000010323 ascorbic acid Nutrition 0.000 description 2
- 239000011668 ascorbic acid Substances 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- PPZMYIBUHIPZOS-UHFFFAOYSA-N histamine dihydrochloride Chemical compound Cl.Cl.NCCC1=CN=CN1 PPZMYIBUHIPZOS-UHFFFAOYSA-N 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 239000008363 phosphate buffer Substances 0.000 description 2
- -1 polyoxyethylene Polymers 0.000 description 2
- 239000001818 polyoxyethylene sorbitan monostearate Substances 0.000 description 2
- 235000010989 polyoxyethylene sorbitan monostearate Nutrition 0.000 description 2
- 229940113124 polysorbate 60 Drugs 0.000 description 2
- 210000003240 portal vein Anatomy 0.000 description 2
- 230000035935 pregnancy Effects 0.000 description 2
- 239000000473 propyl gallate Substances 0.000 description 2
- 235000010388 propyl gallate Nutrition 0.000 description 2
- 229940075579 propyl gallate Drugs 0.000 description 2
- 230000000087 stabilizing effect Effects 0.000 description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- 150000005208 1,4-dihydroxybenzenes Chemical class 0.000 description 1
- 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 description 1
- OLQJQHSAWMFDJE-UHFFFAOYSA-N 2-(hydroxymethyl)-2-nitropropane-1,3-diol Chemical compound OCC(CO)(CO)[N+]([O-])=O OLQJQHSAWMFDJE-UHFFFAOYSA-N 0.000 description 1
- SXAMGRAIZSSWIH-UHFFFAOYSA-N 2-[3-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-1,2,4-oxadiazol-5-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1=NOC(=N1)CC(=O)N1CC2=C(CC1)NN=N2 SXAMGRAIZSSWIH-UHFFFAOYSA-N 0.000 description 1
- 229940044119 2-tert-butylhydroquinone Drugs 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- ODJQKYXPKWQWNK-UHFFFAOYSA-N 3,3'-Thiobispropanoic acid Chemical compound OC(=O)CCSCCC(O)=O ODJQKYXPKWQWNK-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- GHKOFFNLGXMVNJ-UHFFFAOYSA-N Didodecyl thiobispropanoate Chemical compound CCCCCCCCCCCCOC(=O)CCSCCC(=O)OCCCCCCCCCCCC GHKOFFNLGXMVNJ-UHFFFAOYSA-N 0.000 description 1
- 239000003508 Dilauryl thiodipropionate Substances 0.000 description 1
- 239000004258 Ethoxyquin Substances 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 229920000881 Modified starch Polymers 0.000 description 1
- 239000004368 Modified starch Substances 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 235000021314 Palmitic acid Nutrition 0.000 description 1
- 208000008469 Peptic Ulcer Diseases 0.000 description 1
- RVGRUAULSDPKGF-UHFFFAOYSA-N Poloxamer Chemical compound C1CO1.CC1CO1 RVGRUAULSDPKGF-UHFFFAOYSA-N 0.000 description 1
- 229920003110 Primojel Polymers 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 239000003490 Thiodipropionic acid Substances 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 230000000397 acetylating effect Effects 0.000 description 1
- 150000007824 aliphatic compounds Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000003276 anti-hypertensive effect Effects 0.000 description 1
- 229940072107 ascorbate Drugs 0.000 description 1
- 125000003289 ascorbyl group Chemical group [H]O[C@@]([H])(C([H])([H])O*)[C@@]1([H])OC(=O)C(O*)=C1O* 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 229940125692 cardiovascular agent Drugs 0.000 description 1
- 239000002327 cardiovascular agent Substances 0.000 description 1
- 230000002925 chemical effect Effects 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 229940000425 combination drug Drugs 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 229940099112 cornstarch Drugs 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 235000019304 dilauryl thiodipropionate Nutrition 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- 235000019285 ethoxyquin Nutrition 0.000 description 1
- DECIPOUIJURFOJ-UHFFFAOYSA-N ethoxyquin Chemical compound N1C(C)(C)C=C(C)C2=CC(OCC)=CC=C21 DECIPOUIJURFOJ-UHFFFAOYSA-N 0.000 description 1
- 229940093500 ethoxyquin Drugs 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000005429 filling process Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 210000004211 gastric acid Anatomy 0.000 description 1
- 150000002440 hydroxy compounds Chemical class 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000000787 lecithin Substances 0.000 description 1
- 235000010445 lecithin Nutrition 0.000 description 1
- 229940067606 lecithin Drugs 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 235000019426 modified starch Nutrition 0.000 description 1
- PJUIMOJAAPLTRJ-UHFFFAOYSA-N monothioglycerol Chemical compound OCC(O)CS PJUIMOJAAPLTRJ-UHFFFAOYSA-N 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 235000021313 oleic acid Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000008506 pathogenesis Effects 0.000 description 1
- 208000011906 peptic ulcer disease Diseases 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229920001993 poloxamer 188 Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000001587 sorbitan monostearate Substances 0.000 description 1
- 235000011076 sorbitan monostearate Nutrition 0.000 description 1
- 229940035048 sorbitan monostearate Drugs 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- IMCGHZIGRANKHV-AJNGGQMLSA-N tert-butyl (3s,5s)-2-oxo-5-[(2s,4s)-5-oxo-4-propan-2-yloxolan-2-yl]-3-propan-2-ylpyrrolidine-1-carboxylate Chemical compound O1C(=O)[C@H](C(C)C)C[C@H]1[C@H]1N(C(=O)OC(C)(C)C)C(=O)[C@H](C(C)C)C1 IMCGHZIGRANKHV-AJNGGQMLSA-N 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
- 235000019303 thiodipropionic acid Nutrition 0.000 description 1
- 229940035024 thioglycerol Drugs 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- XREXPQGDOPQPAH-QKUPJAQQSA-K trisodium;[(z)-18-[1,3-bis[[(z)-12-sulfonatooxyoctadec-9-enoyl]oxy]propan-2-yloxy]-18-oxooctadec-9-en-7-yl] sulfate Chemical compound [Na+].[Na+].[Na+].CCCCCCC(OS([O-])(=O)=O)C\C=C/CCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C/CC(CCCCCC)OS([O-])(=O)=O)COC(=O)CCCCCCC\C=C/CC(CCCCCC)OS([O-])(=O)=O XREXPQGDOPQPAH-QKUPJAQQSA-K 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
- A61K9/4841—Filling excipients; Inactive ingredients
- A61K9/4858—Organic compounds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/557—Eicosanoids, e.g. leukotrienes or prostaglandins
Landscapes
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/195,575 US4310543A (en) | 1980-10-09 | 1980-10-09 | Prostaglandin compositions |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NZ198533A true NZ198533A (en) | 1984-12-14 |
Family
ID=22721933
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NZ198533A NZ198533A (en) | 1980-10-09 | 1981-10-02 | Soft gelatin capsules containing prostaglandins |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US4310543A (https=) |
| EP (1) | EP0049852B1 (https=) |
| JP (1) | JPS5793911A (https=) |
| AT (1) | ATE14981T1 (https=) |
| AU (1) | AU547175B2 (https=) |
| CA (1) | CA1176567A (https=) |
| DE (1) | DE3171928D1 (https=) |
| DK (1) | DK442881A (https=) |
| IE (1) | IE51637B1 (https=) |
| IL (1) | IL63960A (https=) |
| NZ (1) | NZ198533A (https=) |
| PH (1) | PH17073A (https=) |
| ZA (1) | ZA816852B (https=) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5169634A (en) * | 1988-06-15 | 1992-12-08 | Apothe Kernes Laboratorium A.S. | Pharmaceutical dosage form for the medication of fish |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU1695783A (en) * | 1982-07-19 | 1984-01-26 | Syntex (U.S.A.) Inc. | Encapsulated pge type compositions |
| US4431833A (en) * | 1982-12-27 | 1984-02-14 | American Cyanamid Company | Prostaglandin and hydroxylated fatty acid ester formulations |
| FR2549371B1 (fr) * | 1983-07-20 | 1985-09-13 | Sanofi Sa | Nouvelle composition pharmaceutique contenant de l'acide valproique ou un de ses sels |
| KR850700213A (ko) * | 1984-02-08 | 1985-12-26 | 제이.데스몬드 다비스 | 아세트 아미노펜 젤라틴 캡슐 |
| DE3438830A1 (de) * | 1984-10-23 | 1986-04-30 | Rentschler Arzneimittel | Nifedipin enthaltende darreichungsform und verfahren zu ihrer herstellung |
| US5208256A (en) * | 1990-05-22 | 1993-05-04 | R-Tech Ueno, Ltd. | Treatment of ocular hypertension with a synergistic combination for ocular administration |
| GB2281697A (en) * | 1993-09-14 | 1995-03-15 | Euro Celtique Sa | Laxative compositions in capsules |
| US6180666B1 (en) | 1997-09-05 | 2001-01-30 | Anmax, Inc. | Use of gallic acid esters to increase bioavailability of orally administered pharmaceutical compounds |
| US5962522A (en) * | 1997-09-05 | 1999-10-05 | Avmax, Inc. | Propyl gallate to increase bioavailability of orally administered pharmaceutical compounds |
| WO2001003695A1 (en) * | 1999-07-13 | 2001-01-18 | Avmax, Inc. | Improvement of bioavailability with vitamin c fatty acid esters |
| KR100649860B1 (ko) * | 2000-09-01 | 2006-11-24 | 주식회사종근당 | 알프로스타딜 경점막 및 경피흡수제제 |
| CA2422031C (en) * | 2000-09-13 | 2011-11-15 | Santen Pharmaceutical Co., Ltd. | Ophthalmic solutions comprising difluoroprostaglandin f2 alpha |
| WO2005011704A1 (ja) * | 2003-07-31 | 2005-02-10 | Santen Pharmaceutical Co., Ltd. | プロスタグランジン含有製品 |
| KR101152470B1 (ko) | 2003-08-13 | 2012-06-01 | 바이오콘 리미티드 | 치료제용 마이크로-입자 지방산 염 고형 투약 제형 |
| EP1675548A4 (en) * | 2003-09-25 | 2008-08-13 | Activbiotics Inc | RIFALAZIL FORMULATIONS |
| US9993558B2 (en) | 2004-10-01 | 2018-06-12 | Ramscor, Inc. | Sustained release eye drop formulations |
| US8541413B2 (en) * | 2004-10-01 | 2013-09-24 | Ramscor, Inc. | Sustained release eye drop formulations |
| CN102526064A (zh) * | 2004-12-09 | 2012-07-04 | 参天制药株式会社 | 含有分子内具有氟原子的前列腺素的制品 |
| WO2006068266A1 (ja) * | 2004-12-24 | 2006-06-29 | Santen Pharmaceutical Co., Ltd. | プロスタグランジンＦ２ａ誘導体含有製品 |
| CA2651159A1 (en) * | 2006-04-06 | 2007-10-18 | Activbiotics Pharma Llc | Pharmaceutical compositions and uses thereof |
| EP2327398A3 (en) | 2007-07-19 | 2014-05-21 | R-Tech Ueno, Ltd. | Pharmaceutical composition comprising 11-deoxy-prostaglandin compound and method for stabilizing the compound |
| EP2214635A1 (en) * | 2007-10-19 | 2010-08-11 | Purdue Research Foundation | Solid formulations of crystalline compounds |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2889252A (en) * | 1956-05-14 | 1959-06-02 | American Cyanamid Co | Gelatin capsule containing hexylresorcinol and a lower polyalkylene glycol |
| ZA721937B (en) * | 1971-10-22 | 1972-12-27 | Upjohn Co | Pharmaceutical preparations and uses thereof |
| CA1043259A (en) * | 1972-12-08 | 1978-11-28 | Geoffrey F. Thompson | Medicament preparations and vehicles therefor |
| US3932634A (en) * | 1973-06-28 | 1976-01-13 | Pfizer Inc. | High potency vitamin water dispersible formulations |
| US4052446A (en) * | 1973-08-06 | 1977-10-04 | Hoffmann-La Roche Inc. | 11,16-substituted prostaglandins |
| JPS6019734B2 (ja) * | 1977-05-12 | 1985-05-17 | 三共株式会社 | 安定なプロスタグランジンｅ類製剤の製法 |
| JPS6046094B2 (ja) * | 1977-06-01 | 1985-10-14 | 科研製薬株式会社 | 安定化されたプロスタグランジンｅ類粉末製剤 |
| FI790043A7 (fi) * | 1978-01-17 | 1979-07-18 | Sandoz Ag | Prostaglandiner innehaollande terapeutisk sammansaettning |
-
1980
- 1980-10-09 US US06/195,575 patent/US4310543A/en not_active Expired - Lifetime
-
1981
- 1981-09-09 CA CA000385446A patent/CA1176567A/en not_active Expired
- 1981-09-11 PH PH26191A patent/PH17073A/en unknown
- 1981-09-28 IL IL63960A patent/IL63960A/xx unknown
- 1981-10-02 NZ NZ198533A patent/NZ198533A/en unknown
- 1981-10-02 ZA ZA816852A patent/ZA816852B/xx unknown
- 1981-10-06 EP EP81107988A patent/EP0049852B1/de not_active Expired
- 1981-10-06 AT AT81107988T patent/ATE14981T1/de active
- 1981-10-06 AU AU76068/81A patent/AU547175B2/en not_active Ceased
- 1981-10-06 DE DE8181107988T patent/DE3171928D1/de not_active Expired
- 1981-10-06 DK DK442881A patent/DK442881A/da not_active Application Discontinuation
- 1981-10-08 IE IE2354/81A patent/IE51637B1/en unknown
- 1981-10-08 JP JP56159562A patent/JPS5793911A/ja active Granted
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5169634A (en) * | 1988-06-15 | 1992-12-08 | Apothe Kernes Laboratorium A.S. | Pharmaceutical dosage form for the medication of fish |
Also Published As
| Publication number | Publication date |
|---|---|
| AU7606881A (en) | 1982-04-22 |
| EP0049852A3 (en) | 1983-01-26 |
| ATE14981T1 (de) | 1985-09-15 |
| JPH032848B2 (https=) | 1991-01-17 |
| JPS5793911A (en) | 1982-06-11 |
| EP0049852A2 (de) | 1982-04-21 |
| US4310543A (en) | 1982-01-12 |
| PH17073A (en) | 1984-05-24 |
| IL63960A (en) | 1985-05-31 |
| DK442881A (da) | 1982-04-10 |
| IE812354L (en) | 1982-04-09 |
| ZA816852B (en) | 1982-09-29 |
| EP0049852B1 (de) | 1985-08-21 |
| AU547175B2 (en) | 1985-10-10 |
| IE51637B1 (en) | 1987-01-21 |
| CA1176567A (en) | 1984-10-23 |
| IL63960A0 (en) | 1981-12-31 |
| DE3171928D1 (en) | 1985-09-26 |
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