CA1040534A - Stabilized steroid formulations - Google Patents

Stabilized steroid formulations

Info

Publication number: CA1040534A
Authority: CA; Canada
Prior art keywords: polyethylene glycol; weight; composition; steroid; accordance
Prior art date: 1974-06-13
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired

Application number

CA227,942A

Other languages

English (en)

French (fr)

Other versions

CA227942S (en

Inventor

James W. Mcginity

John A. Hill

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

ER Squibb and Sons LLC

Original Assignee

ER Squibb and Sons LLC

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1974-06-13

Filing date

1975-05-28

Publication date

1978-10-17

1975-05-28 Application filed by ER Squibb and Sons LLC filed Critical ER Squibb and Sons LLC

1978-10-17 Application granted granted Critical

1978-10-17 Publication of CA1040534A publication Critical patent/CA1040534A/en

Status Expired legal-status Critical Current

Links

239000000203 mixture Substances 0.000 title claims abstract description 43
150000003431 steroids Chemical class 0.000 title claims abstract description 36
238000009472 formulation Methods 0.000 title description 10
229920001223 polyethylene glycol Polymers 0.000 claims abstract description 70
239000002202 Polyethylene glycol Substances 0.000 claims abstract description 69
239000003963 antioxidant agent Substances 0.000 claims abstract description 23
235000006708 antioxidants Nutrition 0.000 claims abstract description 22
ZTHYODDOHIVTJV-UHFFFAOYSA-N Propyl gallate Chemical compound CCCOC(=O)C1=CC(O)=C(O)C(O)=C1 ZTHYODDOHIVTJV-UHFFFAOYSA-N 0.000 claims abstract description 20
230000003078 antioxidant effect Effects 0.000 claims abstract description 20
150000002148 esters Chemical class 0.000 claims abstract description 20
239000000463 material Substances 0.000 claims abstract description 20
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 claims abstract description 12
239000004322 Butylated hydroxytoluene Substances 0.000 claims abstract description 11
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 claims abstract description 11
235000010354 butylated hydroxytoluene Nutrition 0.000 claims abstract description 11
229940095259 butylated hydroxytoluene Drugs 0.000 claims abstract description 11
239000000473 propyl gallate Substances 0.000 claims abstract description 10
235000010388 propyl gallate Nutrition 0.000 claims abstract description 10
229940075579 propyl gallate Drugs 0.000 claims abstract description 10
239000004255 Butylated hydroxyanisole Substances 0.000 claims abstract description 7
235000019282 butylated hydroxyanisole Nutrition 0.000 claims abstract description 7
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 claims abstract description 7
229940043253 butylated hydroxyanisole Drugs 0.000 claims abstract description 7
HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 claims abstract description 7
229940001584 sodium metabisulfite Drugs 0.000 claims abstract description 7
235000010262 sodium metabisulphite Nutrition 0.000 claims abstract description 7
235000010323 ascorbic acid Nutrition 0.000 claims abstract description 6
229960005070 ascorbic acid Drugs 0.000 claims abstract description 6
239000011668 ascorbic acid Substances 0.000 claims abstract description 6
DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 claims abstract description 5
229940001607 sodium bisulfite Drugs 0.000 claims abstract description 5
235000010267 sodium hydrogen sulphite Nutrition 0.000 claims abstract description 5
-1 glycol ester Chemical class 0.000 claims description 28
239000004698 Polyethylene Substances 0.000 claims description 27
229920000573 polyethylene Polymers 0.000 claims description 23
LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 19
239000002738 chelating agent Substances 0.000 claims description 14
238000000034 method Methods 0.000 claims description 13
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 13
235000019271 petrolatum Nutrition 0.000 claims description 12
239000003871 white petrolatum Substances 0.000 claims description 11
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 10
239000002480 mineral oil Substances 0.000 claims description 8
235000010446 mineral oil Nutrition 0.000 claims description 8
238000004519 manufacturing process Methods 0.000 claims description 3
BDOYKFSQFYNPKF-UHFFFAOYSA-N 2-[2-[bis(carboxymethyl)amino]ethyl-(carboxymethyl)amino]acetic acid;sodium Chemical group [Na].[Na].OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O BDOYKFSQFYNPKF-UHFFFAOYSA-N 0.000 claims 2
MBJJLHWSFGHIAA-UDCWSGSHSA-N (8s,9s,10r,13s,14s,17s)-10,13-dimethyl-17-(2,2,2-trihydroxyacetyl)-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)C(=O)C(O)(O)O)[C@@H]4[C@@H]3CCC2=C1 MBJJLHWSFGHIAA-UDCWSGSHSA-N 0.000 claims 1
QWOJMRHUQHTCJG-UHFFFAOYSA-N CC([CH2-])=O Chemical compound CC([CH2-])=O QWOJMRHUQHTCJG-UHFFFAOYSA-N 0.000 claims 1
208000017520 skin disease Diseases 0.000 abstract description 2
239000003981 vehicle Substances 0.000 description 22
239000000243 solution Substances 0.000 description 18
239000006210 lotion Substances 0.000 description 13
KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 11
238000013019 agitation Methods 0.000 description 9
239000002674 ointment Substances 0.000 description 9
150000002334 glycols Chemical class 0.000 description 7
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
239000012153 distilled water Substances 0.000 description 6
150000002978 peroxides Chemical class 0.000 description 6
238000010438 heat treatment Methods 0.000 description 5
229920002642 Polysorbate 65 Polymers 0.000 description 4
229940093429 polyethylene glycol 6000 Drugs 0.000 description 4
239000001816 polyoxyethylene sorbitan tristearate Substances 0.000 description 4
235000010988 polyoxyethylene sorbitan tristearate Nutrition 0.000 description 4
229940099511 polysorbate 65 Drugs 0.000 description 4
238000003756 stirring Methods 0.000 description 4
239000012141 concentrate Substances 0.000 description 3
230000000694 effects Effects 0.000 description 3
229940068886 polyethylene glycol 300 Drugs 0.000 description 3
150000003839 salts Chemical class 0.000 description 3
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
QPCDCPDFJACHGM-UHFFFAOYSA-N N,N-bis{2-[bis(carboxymethyl)amino]ethyl}glycine Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(=O)O)CCN(CC(O)=O)CC(O)=O QPCDCPDFJACHGM-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
229910052783 alkali metal Inorganic materials 0.000 description 2
229910052784 alkaline earth metal Inorganic materials 0.000 description 2
150000003863 ammonium salts Chemical class 0.000 description 2
230000007423 decrease Effects 0.000 description 2
239000006185 dispersion Substances 0.000 description 2
239000012535 impurity Substances 0.000 description 2
239000003607 modifier Substances 0.000 description 2
229960003330 pentetic acid Drugs 0.000 description 2
229940057838 polyethylene glycol 4000 Drugs 0.000 description 2
239000012047 saturated solution Substances 0.000 description 2
239000011734 sodium Substances 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
229940083542 sodium Drugs 0.000 description 2
235000015424 sodium Nutrition 0.000 description 2
ZESRJSPZRDMNHY-YFWFAHHUSA-N 11-deoxycorticosterone Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 ZESRJSPZRDMNHY-YFWFAHHUSA-N 0.000 description 1
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
239000005977 Ethylene Substances 0.000 description 1
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
239000004264 Petrolatum Substances 0.000 description 1
201000004681 Psoriasis Diseases 0.000 description 1
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
230000002411 adverse Effects 0.000 description 1
230000032683 aging Effects 0.000 description 1
150000001342 alkaline earth metals Chemical class 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000003246 corticosteroid Substances 0.000 description 1
235000014113 dietary fatty acids Nutrition 0.000 description 1
238000002845 discoloration Methods 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
230000009977 dual effect Effects 0.000 description 1
229960001484 edetic acid Drugs 0.000 description 1
239000000194 fatty acid Substances 0.000 description 1
229930195729 fatty acid Natural products 0.000 description 1
150000004665 fatty acids Chemical group 0.000 description 1
229940023564 hydroxylated lanolin Drugs 0.000 description 1
208000027866 inflammatory disease Diseases 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
238000010907 mechanical stirring Methods 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
150000002739 metals Chemical class 0.000 description 1
239000003921 oil Substances 0.000 description 1
238000010525 oxidative degradation reaction Methods 0.000 description 1
229940066842 petrolatum Drugs 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
230000000979 retarding effect Effects 0.000 description 1
229940037001 sodium edetate Drugs 0.000 description 1
230000000087 stabilizing effect Effects 0.000 description 1
230000003068 static effect Effects 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
230000008719 thickening Effects 0.000 description 1
230000000699 topical effect Effects 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
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0014—Skin, i.e. galenical aspects of topical compositions
- 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
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
- A61K31/58—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids containing heterocyclic rings, e.g. danazol, stanozolol, pancuronium or digitogenin
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J71/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
- C07J71/0005—Oxygen-containing hetero ring
- C07J71/0026—Oxygen-containing hetero ring cyclic ketals
- C07J71/0031—Oxygen-containing hetero ring cyclic ketals at positions 16, 17

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
General Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
Medicinal Chemistry (AREA)
Animal Behavior & Ethology (AREA)
Organic Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
General Chemical & Material Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Dermatology (AREA)
Epidemiology (AREA)
Rheumatology (AREA)
Pain & Pain Management (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Medicinal Preparation (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CA227,942A 1974-06-13 1975-05-28 Stabilized steroid formulations Expired CA1040534A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US47898574A	1974-06-13	1974-06-13

Publications (1)

Publication Number	Publication Date
CA1040534A true CA1040534A (en)	1978-10-17

Family

ID=23902198

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA227,942A Expired CA1040534A (en)	1974-06-13	1975-05-28	Stabilized steroid formulations

Country Status (11)

Country	Link
JP (1)	JPS5126216A (2)
BE (1)	BE830239A (2)
CA (1)	CA1040534A (2)
DE (1)	DE2526251A1 (2)
FR (1)	FR2274310A1 (2)
GB (1)	GB1497836A (2)
IE (1)	IE41417B1 (2)
NL (1)	NL7506872A (2)
PH (1)	PH14507A (2)
YU (1)	YU152175A (2)
ZA (1)	ZA753429B (2)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS5612306A (en) *	1979-07-12	1981-02-06	Nippon Zoki Pharmaceut Co Ltd	Novel base for external preparation
JPS56135416A (en) *	1980-03-27	1981-10-22	Mitsubishi Chem Ind Ltd	Pharmaceutical preparation for skin
US6156341A (en) *	1994-07-04	2000-12-05	Schering Aktiensgesellschaft	Low-dosed steroid tablets that contain gallic acid ester as an antioxidant, process for production, and use
US7189759B2 (en) *	2001-05-23	2007-03-13	Medicis Pharmaceutical Corporation	Compositions for the treatment of pigmentation disorders and methods for their manufacture
DE102004059880A1 (de) *	2004-12-10	2006-06-14	Grünenthal GmbH	Stabiles, hormonhaltiges (Zwischen-)Produkt
EP3253370A4 (en) *	2015-02-05	2018-08-01	Marc Selner	Ionic nanovesicle suspension and biocide prepared therefrom

1975
- 1975-05-26 IE IE1175/75A patent/IE41417B1/en unknown
- 1975-05-27 ZA ZA00753429A patent/ZA753429B/xx unknown
- 1975-05-28 CA CA227,942A patent/CA1040534A/en not_active Expired
- 1975-05-29 GB GB23485/75A patent/GB1497836A/en not_active Expired
- 1975-05-30 PH PH17207A patent/PH14507A/en unknown
- 1975-06-10 NL NL7506872A patent/NL7506872A/xx not_active Application Discontinuation
- 1975-06-12 DE DE19752526251 patent/DE2526251A1/de not_active Ceased
- 1975-06-12 YU YU01521/75A patent/YU152175A/xx unknown
- 1975-06-13 JP JP50072615A patent/JPS5126216A/ja active Granted
- 1975-06-13 FR FR7518635A patent/FR2274310A1/fr active Granted
- 1975-06-13 BE BE157333A patent/BE830239A/xx not_active IP Right Cessation

Also Published As

Publication number	Publication date
FR2274310B1 (2)	1980-05-16
FR2274310A1 (fr)	1976-01-09
IE41417L (en)	1975-12-13
JPS5747971B2 (2)	1982-10-13
ZA753429B (en)	1976-04-28
PH14507A (en)	1981-08-21
NL7506872A (nl)	1975-12-16
AU8168175A (en)	1976-12-02
YU152175A (en)	1983-10-31
GB1497836A (en)	1978-01-12
BE830239A (fr)	1975-10-01
JPS5126216A (en)	1976-03-04
DE2526251A1 (de)	1976-01-02
IE41417B1 (en)	1980-01-02

Publication	Publication Date	Title
CA1207668A (en)	1986-07-15	Oil-in-water cream containing hydrocortisone butyrate propionate
EP0037161A2 (en)	1981-10-07	Creamy cleansing compositions
HU185159B (en)	1984-12-28	Process for the preparation of stable injectable beta-carotine solubilisate
JP3447935B2 (ja)	2003-09-16	巨大液晶により安定化されたレチノイドを含有する親水型化粧料組成物
EP0316834B1 (en)	1992-06-24	Steroid cream formulation
CA1085725A (en)	1980-09-16	Topical steroid formulations
CA1040534A (en)	1978-10-17	Stabilized steroid formulations
LU81902A1 (de)	1980-04-22	Transdermales medikationssystem fuer isosorbiddinitrat
EP0231621A2 (en)	1987-08-12	Topical pharmaceutical composition comprising pseudomonic acid or a salt or ester thereof and a corticosteroid
EP0689830B1 (en)	2001-09-26	Skin cosmetic composition
CA1040099A (en)	1978-10-10	Topical steroid formulation
EP0804150A2 (de)	1997-11-05	Fettsäurederivate enthaltende lotionen
US4794107A (en)	1988-12-27	Ointment
US6979454B1 (en)	2005-12-27	Biologically active composition
IE43270B1 (en)	1981-01-28	Steroid compositions
US4279901A (en)	1981-07-21	Topical ointment
DE2241667B2 (de)	1974-09-19	Stabiles pharmazeutisches Mittel in Form einer wässrigen oralen anwendbaren Suspension
US2771395A (en)	1956-11-20	Aqueous alcoholic hair grooming preparation employing sodium carboxymethyl cellulose
JP3803595B2 (ja)	2006-08-02	尿素含有皮膚外用組成物
US20070077261A1 (en)	2007-04-05	Compositions and method for enhancing the solubility of ascorbic acid using solubilization enhancers
JPS58164508A (ja)	1983-09-29	イソプレニルカルボン酸含有外用組成物
KR102923029B1 (ko)	2026-02-06	미리스틸알코올 및 세테아릴알코올을 포함하는 액정크림 화장료 조성물 및 이의 제조 방법
DE68902697T2 (de)	1993-04-08	Fluessiges praeparat mit niedriger temperatur-stabilitaet.
US2758931A (en)	1956-08-14	Antioxidant composition
WO2022219017A1 (en)	2022-10-20	Retinol formulation (ii)