CA1280695C - Compose de nalbuphine anesthesique local et analgesique et methode d'utilisation - Google Patents

Compose de nalbuphine anesthesique local et analgesique et methode d'utilisation

Info

Publication number: CA1280695C
Authority: CA; Canada
Prior art keywords: nalbuphine; composition; local anesthetic; tetracaine; bupivacaine
Prior art date: 1985-04-29
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 - Lifetime

Application number

CA000507505A

Other languages

English (en)

Inventor

Benigno M. Sulit, Jr.

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.)

Individual

Original Assignee

Individual

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.)

1985-04-29

Filing date

1986-04-24

Publication date

1991-02-26

1986-04-24 Application filed by Individual filed Critical Individual

1991-02-26 Application granted granted Critical

1991-02-26 Publication of CA1280695C publication Critical patent/CA1280695C/fr

2008-02-26 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

239000000203 mixture Substances 0.000 title claims abstract description 20
230000000202 analgesic effect Effects 0.000 title claims abstract description 16
239000003589 local anesthetic agent Substances 0.000 title claims abstract description 15
230000036592 analgesia Effects 0.000 title abstract description 4
NETZHAKZCGBWSS-CEDHKZHLSA-N nalbuphine Chemical compound C([C@]12[C@H]3OC=4C(O)=CC=C(C2=4)C[C@@H]2[C@]1(O)CC[C@@H]3O)CN2CC1CCC1 NETZHAKZCGBWSS-CEDHKZHLSA-N 0.000 claims abstract description 27
229960000805 nalbuphine Drugs 0.000 claims abstract description 27
LEBVLXFERQHONN-UHFFFAOYSA-N 1-butyl-N-(2,6-dimethylphenyl)piperidine-2-carboxamide Chemical compound CCCCN1CCCCC1C(=O)NC1=C(C)C=CC=C1C LEBVLXFERQHONN-UHFFFAOYSA-N 0.000 claims abstract description 12
229960003150 bupivacaine Drugs 0.000 claims abstract description 12
229960002372 tetracaine Drugs 0.000 claims abstract description 12
GKCBAIGFKIBETG-UHFFFAOYSA-N tetracaine Chemical compound CCCCNC1=CC=C(C(=O)OCCN(C)C)C=C1 GKCBAIGFKIBETG-UHFFFAOYSA-N 0.000 claims abstract description 12
150000003839 salts Chemical class 0.000 claims abstract 8
229960002409 mepivacaine Drugs 0.000 claims abstract 7
INWLQCZOYSRPNW-UHFFFAOYSA-N mepivacaine Chemical compound CN1CCCCC1C(=O)NC1=C(C)C=CC=C1C INWLQCZOYSRPNW-UHFFFAOYSA-N 0.000 claims abstract 7
239000002552 dosage form Substances 0.000 claims abstract 3
ZPUCINDJVBIVPJ-LJISPDSOSA-N cocaine Chemical compound O([C@H]1C[C@@H]2CC[C@@H](N2C)[C@H]1C(=O)OC)C(=O)C1=CC=CC=C1 ZPUCINDJVBIVPJ-LJISPDSOSA-N 0.000 claims description 8
-1 cyclomethylcaine Chemical compound 0.000 claims description 5
DKLKMKYDWHYZTD-UHFFFAOYSA-N Hexylcaine Chemical compound C=1C=CC=CC=1C(=O)OC(C)CNC1CCCCC1 DKLKMKYDWHYZTD-UHFFFAOYSA-N 0.000 claims description 4
YQKAVWCGQQXBGW-UHFFFAOYSA-N Piperocaine Chemical compound CC1CCCCN1CCCOC(=O)C1=CC=CC=C1 YQKAVWCGQQXBGW-UHFFFAOYSA-N 0.000 claims description 4
KCLANYCVBBTKTO-UHFFFAOYSA-N Proparacaine Chemical compound CCCOC1=CC=C(C(=O)OCCN(CC)CC)C=C1N KCLANYCVBBTKTO-UHFFFAOYSA-N 0.000 claims description 4
229960002023 chloroprocaine Drugs 0.000 claims description 4
VDANGULDQQJODZ-UHFFFAOYSA-N chloroprocaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1Cl VDANGULDQQJODZ-UHFFFAOYSA-N 0.000 claims description 4
229960003920 cocaine Drugs 0.000 claims description 4
229960000385 dyclonine Drugs 0.000 claims description 4
BZEWSEKUUPWQDQ-UHFFFAOYSA-N dyclonine Chemical compound C1=CC(OCCCC)=CC=C1C(=O)CCN1CCCCC1 BZEWSEKUUPWQDQ-UHFFFAOYSA-N 0.000 claims description 4
229960005388 hexylcaine Drugs 0.000 claims description 4
229960004194 lidocaine Drugs 0.000 claims description 4
229950007049 phenacaine Drugs 0.000 claims description 4
QXDAEKSDNVPFJG-UHFFFAOYSA-N phenacaine Chemical compound C1=CC(OCC)=CC=C1N\C(C)=N\C1=CC=C(OCC)C=C1 QXDAEKSDNVPFJG-UHFFFAOYSA-N 0.000 claims description 4
229960001045 piperocaine Drugs 0.000 claims description 4
229960001896 pramocaine Drugs 0.000 claims description 4
DQKXQSGTHWVTAD-UHFFFAOYSA-N pramocaine Chemical compound C1=CC(OCCCC)=CC=C1OCCCN1CCOCC1 DQKXQSGTHWVTAD-UHFFFAOYSA-N 0.000 claims description 4
229960004919 procaine Drugs 0.000 claims description 4
MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 claims description 4
229960003981 proparacaine Drugs 0.000 claims description 4
230000003444 anaesthetic effect Effects 0.000 claims description 2
XNMYNYSCEJBRPZ-UHFFFAOYSA-N 2-[(3-butyl-1-isoquinolinyl)oxy]-N,N-dimethylethanamine Chemical compound C1=CC=C2C(OCCN(C)C)=NC(CCCC)=CC2=C1 XNMYNYSCEJBRPZ-UHFFFAOYSA-N 0.000 claims 3
NNJVILVZKWQKPM-UHFFFAOYSA-N Lidocaine Chemical compound CCN(CC)CC(=O)NC1=C(C)C=CC=C1C NNJVILVZKWQKPM-UHFFFAOYSA-N 0.000 claims 3
229960001747 cinchocaine Drugs 0.000 claims 3
PUFQVTATUTYEAL-UHFFFAOYSA-N cinchocaine Chemical compound C1=CC=CC2=NC(OCCCC)=CC(C(=O)NCCN(CC)CC)=C21 PUFQVTATUTYEAL-UHFFFAOYSA-N 0.000 claims 3
229960001807 prilocaine Drugs 0.000 claims 3
MVFGUOIZUNYYSO-UHFFFAOYSA-N prilocaine Chemical compound CCCNC(C)C(=O)NC1=CC=CC=C1C MVFGUOIZUNYYSO-UHFFFAOYSA-N 0.000 claims 3
229960005038 quinisocaine Drugs 0.000 claims 3
239000006195 ophthalmic dosage form Substances 0.000 claims 2
241000124008 Mammalia Species 0.000 abstract description 6
239000004480 active ingredient Substances 0.000 abstract 1
229940035564 duration Drugs 0.000 abstract 1
208000002193 Pain Diseases 0.000 description 17
230000036407 pain Effects 0.000 description 16
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 9
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
239000000243 solution Substances 0.000 description 7
239000003795 chemical substances by application Substances 0.000 description 4
238000002347 injection Methods 0.000 description 4
239000007924 injection Substances 0.000 description 4
LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 4
QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 4
HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 4
229940001584 sodium metabisulfite Drugs 0.000 description 4
235000010262 sodium metabisulphite Nutrition 0.000 description 4
241001535291 Analges Species 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
239000002674 ointment Substances 0.000 description 3
235000006810 Caesalpinia ciliata Nutrition 0.000 description 2
241000059739 Caesalpinia ciliata Species 0.000 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 description 2
208000004550 Postoperative Pain Diseases 0.000 description 2
229960000686 benzalkonium chloride Drugs 0.000 description 2
CADWTSSKOVRVJC-UHFFFAOYSA-N benzyl(dimethyl)azanium;chloride Chemical compound [Cl-].C[NH+](C)CC1=CC=CC=C1 CADWTSSKOVRVJC-UHFFFAOYSA-N 0.000 description 2
210000000988 bone and bone Anatomy 0.000 description 2
239000003153 chemical reaction reagent Substances 0.000 description 2
OSASVXMJTNOKOY-UHFFFAOYSA-N chlorobutanol Chemical compound CC(C)(O)C(Cl)(Cl)Cl OSASVXMJTNOKOY-UHFFFAOYSA-N 0.000 description 2
150000004683 dihydrates Chemical class 0.000 description 2
229940079593 drug Drugs 0.000 description 2
239000003814 drug Substances 0.000 description 2
239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 2
229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 2
UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 description 2
235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 2
239000004615 ingredient Substances 0.000 description 2
239000007972 injectable composition Substances 0.000 description 2
YECIFGHRMFEPJK-UHFFFAOYSA-N lidocaine hydrochloride monohydrate Chemical compound O.[Cl-].CC[NH+](CC)CC(=O)NC1=C(C)C=CC=C1C YECIFGHRMFEPJK-UHFFFAOYSA-N 0.000 description 2
235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 2
239000004292 methyl p-hydroxybenzoate Substances 0.000 description 2
229960002216 methylparaben Drugs 0.000 description 2
235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 2
239000004405 propyl p-hydroxybenzoate Substances 0.000 description 2
229960003415 propylparaben Drugs 0.000 description 2
239000011734 sodium Substances 0.000 description 2
239000001509 sodium citrate Substances 0.000 description 2
NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 2
FEWJPZIEWOKRBE-UHFFFAOYSA-M 3-carboxy-2,3-dihydroxypropanoate Chemical compound OC(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-M 0.000 description 1
BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
HEFNNWSXXWATRW-UHFFFAOYSA-N Ibuprofen Chemical compound CC(C)CC1=CC=C(C(C)C(O)=O)C=C1 HEFNNWSXXWATRW-UHFFFAOYSA-N 0.000 description 1
206010028980 Neoplasm Diseases 0.000 description 1
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
229960001138 acetylsalicylic acid Drugs 0.000 description 1
239000000730 antalgic agent Substances 0.000 description 1
230000003064 anti-oxidating effect Effects 0.000 description 1
201000011510 cancer Diseases 0.000 description 1
239000000969 carrier Substances 0.000 description 1
229960004926 chlorobutanol Drugs 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
239000008121 dextrose Substances 0.000 description 1
LZPBLUATTGKZBH-UHFFFAOYSA-L fenoprofen calcium Chemical compound O.O.[Ca+2].[O-]C(=O)C(C)C1=CC=CC(OC=2C=CC=CC=2)=C1.[O-]C(=O)C(C)C1=CC=CC(OC=2C=CC=CC=2)=C1 LZPBLUATTGKZBH-UHFFFAOYSA-L 0.000 description 1
229960002390 flurbiprofen Drugs 0.000 description 1
SYTBZMRGLBWNTM-UHFFFAOYSA-N flurbiprofen Chemical compound FC1=CC(C(C(O)=O)C)=CC=C1C1=CC=CC=C1 SYTBZMRGLBWNTM-UHFFFAOYSA-N 0.000 description 1
ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
229960001680 ibuprofen Drugs 0.000 description 1
238000007918 intramuscular administration Methods 0.000 description 1
238000010255 intramuscular injection Methods 0.000 description 1
239000007927 intramuscular injection Substances 0.000 description 1
235000015250 liver sausages Nutrition 0.000 description 1
210000003205 muscle Anatomy 0.000 description 1
239000004084 narcotic analgesic agent Substances 0.000 description 1
230000003533 narcotic effect Effects 0.000 description 1
210000005036 nerve Anatomy 0.000 description 1
RJMUSRYZPJIFPJ-UHFFFAOYSA-N niclosamide Chemical compound OC1=CC=C(Cl)C=C1C(=O)NC1=CC=C([N+]([O-])=O)C=C1Cl RJMUSRYZPJIFPJ-UHFFFAOYSA-N 0.000 description 1
239000003883 ointment base Substances 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
229940093430 polyethylene glycol 1500 Drugs 0.000 description 1
229940068886 polyethylene glycol 300 Drugs 0.000 description 1
229940068917 polyethylene glycols Drugs 0.000 description 1
229940120090 pontocaine Drugs 0.000 description 1
150000003892 tartrate salts Chemical class 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1

Landscapes

Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

CA000507505A 1985-04-29 1986-04-24 Compose de nalbuphine anesthesique local et analgesique et methode d'utilisation Expired - Lifetime CA1280695C (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
PH3220485		1985-04-29
PH32,204		1985-04-29

Publications (1)

Publication Number	Publication Date
CA1280695C true CA1280695C (fr)	1991-02-26

Family

ID=19935335

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000507505A Expired - Lifetime CA1280695C (fr)	1985-04-29	1986-04-24	Compose de nalbuphine anesthesique local et analgesique et methode d'utilisation

Country Status (3)

Country	Link
AU (1)	AU586247B2 (fr)
CA (1)	CA1280695C (fr)
NZ (1)	NZ215971A (fr)

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
IL26896A (en) *	1966-01-19	1970-11-30	Endo Lab	14 - Hydroxynormorphinins and 14 - Hydroxynormorphinones

1986
- 1986-04-24 CA CA000507505A patent/CA1280695C/fr not_active Expired - Lifetime
- 1986-04-28 NZ NZ21597186A patent/NZ215971A/xx unknown
- 1986-04-29 AU AU56879/86A patent/AU586247B2/en not_active Ceased

Also Published As

Publication number	Publication date
NZ215971A (en)	1989-02-24
AU5687986A (en)	1986-11-06
AU586247B2 (en)	1989-07-06

Legal Events

Date	Code	Title	Description
2003-02-26	MKLA	Lapsed

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