NZ613313B2 - Pharmaceutical formulation for topical administration comprising b220 - Google Patents
Pharmaceutical formulation for topical administration comprising b220 Download PDFInfo
- Publication number
- NZ613313B2 NZ613313B2 NZ613313A NZ61331312A NZ613313B2 NZ 613313 B2 NZ613313 B2 NZ 613313B2 NZ 613313 A NZ613313 A NZ 613313A NZ 61331312 A NZ61331312 A NZ 61331312A NZ 613313 B2 NZ613313 B2 NZ 613313B2
- Authority
- NZ
- New Zealand
- Prior art keywords
- use according
- medicament
- therapeutically active
- skin
- active ingredient
- Prior art date
Links
- 230000000699 topical Effects 0.000 title claims abstract description 13
- 239000008194 pharmaceutical composition Substances 0.000 title description 3
- 239000003814 drug Substances 0.000 claims abstract description 15
- 210000004400 Mucous Membrane Anatomy 0.000 claims abstract description 10
- 210000003491 Skin Anatomy 0.000 claims abstract description 10
- 150000003839 salts Chemical class 0.000 claims abstract description 9
- 239000011780 sodium chloride Substances 0.000 claims abstract description 9
- 208000006213 Herpesviridae Infection Diseases 0.000 claims abstract description 7
- 238000004519 manufacturing process Methods 0.000 claims abstract description 3
- ZUNBGWZFZVZJHX-UHFFFAOYSA-N 2-(2,3-dimethyl-6H-indolo[2,3-b]quinoxalin-1-yl)-N,N-dimethylethanamine Chemical compound N1C2=NC3=CC=CC=C3C2=NC2=C1C=C(C)C(C)=C2CCN(C)C ZUNBGWZFZVZJHX-UHFFFAOYSA-N 0.000 claims description 6
- 239000004480 active ingredient Substances 0.000 claims description 6
- 239000002260 anti-inflammatory agent Substances 0.000 claims description 6
- 229940116904 ANTIINFLAMMATORY THERAPEUTIC RADIOPHARMACEUTICALS Drugs 0.000 claims description 2
- 229940064005 Antibiotic throat preparations Drugs 0.000 claims description 2
- 229940083879 Antibiotics FOR TREATMENT OF HEMORRHOIDS AND ANAL FISSURES FOR TOPICAL USE Drugs 0.000 claims description 2
- 229940042052 Antibiotics for systemic use Drugs 0.000 claims description 2
- 229940042786 Antitubercular Antibiotics Drugs 0.000 claims description 2
- 229940093922 Gynecological Antibiotics Drugs 0.000 claims description 2
- 229940074726 OPHTHALMOLOGIC ANTIINFLAMMATORY AGENTS Drugs 0.000 claims description 2
- 229940024982 Topical Antifungal Antibiotics Drugs 0.000 claims description 2
- 239000000730 antalgic agent Substances 0.000 claims description 2
- 239000003242 anti bacterial agent Substances 0.000 claims description 2
- 239000003443 antiviral agent Substances 0.000 claims description 2
- 230000003115 biocidal Effects 0.000 claims description 2
- 239000003193 general anesthetic agent Substances 0.000 claims description 2
- 229940079866 intestinal antibiotics Drugs 0.000 claims description 2
- 229940005935 ophthalmologic Antibiotics Drugs 0.000 claims description 2
- 239000007921 spray Substances 0.000 claims 2
- 229940035676 ANALGESICS Drugs 0.000 claims 1
- 230000000202 analgesic Effects 0.000 claims 1
- 229940121363 anti-inflammatory agents Drugs 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 239000006071 cream Substances 0.000 claims 1
- 230000002500 effect on skin Effects 0.000 claims 1
- 239000006260 foam Substances 0.000 claims 1
- 239000000499 gel Substances 0.000 claims 1
- 239000007788 liquid Substances 0.000 claims 1
- 239000006210 lotion Substances 0.000 claims 1
- 239000002674 ointment Substances 0.000 claims 1
- FPLSGFJELWCFTH-UHFFFAOYSA-N 2-(2,3-dimethylindolo[3,2-b]quinoxalin-6-yl)-N,N-dimethylethanamine Chemical compound CC1=C(C)C=C2N=C3N(CCN(C)C)C4=CC=CC=C4C3=NC2=C1 FPLSGFJELWCFTH-UHFFFAOYSA-N 0.000 abstract 1
- 241000124008 Mammalia Species 0.000 description 5
- 239000002253 acid Substances 0.000 description 3
- 230000000840 anti-viral Effects 0.000 description 3
- 230000000306 recurrent Effects 0.000 description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-K [O-]P([O-])([O-])=O Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- KRKNYBCHXYNGOX-UHFFFAOYSA-K 2qpq Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- GHOKWGTUZJEAQD-ZETCQYMHSA-M 3-[[(2R)-2,4-dihydroxy-3,3-dimethylbutanoyl]amino]propanoate Chemical compound OCC(C)(C)[C@@H](O)C(=O)NCCC([O-])=O GHOKWGTUZJEAQD-ZETCQYMHSA-M 0.000 description 1
- 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
- NXOVZLREWXNIDP-UHFFFAOYSA-N 7H-pyrazino[2,3-c]carbazole Chemical class N1=CC=NC2=C3C4=CC=CC=C4NC3=CC=C21 NXOVZLREWXNIDP-UHFFFAOYSA-N 0.000 description 1
- 229940022663 Acetate Drugs 0.000 description 1
- 229940072107 Ascorbate Drugs 0.000 description 1
- 229940001468 Citrate Drugs 0.000 description 1
- DSLZVSRJTYRBFB-LLEIAEIESA-L D-glucarate(2-) Chemical compound [O-]C(=O)[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O DSLZVSRJTYRBFB-LLEIAEIESA-L 0.000 description 1
- RGHNJXZEOKUKBD-SQOUGZDYSA-M D-gluconate Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O RGHNJXZEOKUKBD-SQOUGZDYSA-M 0.000 description 1
- WXTMDXOMEHJXQO-UHFFFAOYSA-N Gentisic acid Chemical compound OC(=O)C1=CC(O)=CC=C1O WXTMDXOMEHJXQO-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 208000009889 Herpes Simplex Diseases 0.000 description 1
- 206010019973 Herpes virus infection Diseases 0.000 description 1
- 241000701024 Human betaherpesvirus 5 Species 0.000 description 1
- TYQCGQRIZGCHNB-JLAZNSOCSA-N L-ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(O)=C(O)C1=O TYQCGQRIZGCHNB-JLAZNSOCSA-N 0.000 description 1
- 229940001447 Lactate Drugs 0.000 description 1
- FEWJPZIEWOKRBE-XIXRPRMCSA-N Mesotartaric acid Chemical compound OC(=O)[C@@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-XIXRPRMCSA-N 0.000 description 1
- 241000700584 Simplexvirus Species 0.000 description 1
- 241000700605 Viruses Species 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 238000004166 bioassay Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 229940079593 drugs Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N fumaric acid Chemical compound OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- -1 glucaronate Chemical compound 0.000 description 1
- 229940050410 gluconate Drugs 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-L maleate(2-) Chemical compound [O-]C(=O)\C=C/C([O-])=O VZCYOOQTPOCHFL-UPHRSURJSA-L 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- 229940014662 pantothenate Drugs 0.000 description 1
- 235000019161 pantothenic acid Nutrition 0.000 description 1
- 239000011713 pantothenic acid Substances 0.000 description 1
- TWBYWOBDOCUKOW-UHFFFAOYSA-M pyridine-4-carboxylate Chemical compound [O-]C(=O)C1=CC=NC=C1 TWBYWOBDOCUKOW-UHFFFAOYSA-M 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
- 229960001860 salicylate Drugs 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229940086735 succinate Drugs 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2300/00—Mixtures or combinations of active ingredients, wherein at least one active ingredient is fully defined in groups A61K31/00 - A61K41/00
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/4985—Pyrazines or piperazines ortho- or peri-condensed with heterocyclic ring systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
-
- 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
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0053—Mouth and digestive tract, i.e. intraoral and peroral administration
- A61K9/006—Oral mucosa, e.g. mucoadhesive forms, sublingual droplets; Buccal patches or films; Buccal sprays
-
- 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
- A61K9/06—Ointments; Bases therefor; Other semi-solid forms, e.g. creams, sticks, gels
-
- 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
- A61K9/08—Solutions
-
- 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
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/20—Antivirals for DNA viruses
- A61P31/22—Antivirals for DNA viruses for herpes viruses
Abstract
Disclosed herein is the use of 2,3-dimethyl-6-(N,N-dimethylaminoethyl)-6H-indolo-(2,3-b)quinoxaline (B-220) or a pharmaceutically acceptable salt for the manufacturing of a medicament for use in the treatment of herpes virus infections of the skin or mucous membranes in a mammalian subject by topical administration of a therapeutically effective dose of said medicament to the skin or mucous membrane of the mammalian subject. al administration of a therapeutically effective dose of said medicament to the skin or mucous membrane of the mammalian subject.
Description
There however still remains a need for effective drugs and methods of treatment for primary
as well as recurrent herpes infections.
B-220 was disclosed for the first time in the PCT application published as WO87/04436,
which showed the antiviral effect of a number of indoloquinoxalines against herpes simplex
virus of both type 1 and 2. The antiviral effect was shown by injecting the test substance in
mice receiving also an intracerebral injection of the virus.
The antiviral activity of B-220 against human cytomegalovirus has also been mentioned in
the PCT application published as WO07/084073, where B-220 is used as a reference
compound in a modified plaque assay.
Summary of the invention
It has now been found that primary and recurrent herpes virus infections can be surprisingly
effectively treated by topical administration of B-220.
The invention therefore relates to the use of 2,3-dimethyl(N,N-dimethylaminoethyl)-6H-
indolo-(2,3-b)quinoxaline or a pharmaceutically acceptable salt for the manufacturing of a
medicament for use in the treatment of herpes virus infections of the skin or mucous
membranes in a mammalian subject by topical administration of a therapeutically effective
dose of said medicament to the skin or mucous membrane of the mammalian subject.
Other embodiments of the invention are described herein for completeness.
In one such embodiment the invention relates to a pharmaceutical composition for topical
administration comprising 2,3-dimethyl(N,N-dimethylaminoethyl)-6H-indolo-(2,3-
b)quinoxaline (B-220) or a pharmaceutically acceptable salt thereof in a pharmaceutically
acceptable carrier.
The composition of the invention is useful for topical administration to a mammal subject
suffering from a primary or recurrent herpes virus infection, especially of oral-facial type.
In one embodiment, the pharmaceutical composition of the invention additionally comprises
at least one additional therapeutically active ingredient suitable for topical administration.
According to another aspect, the invention relates to B-220 or a pharmaceutically acceptable
salt thereof for use in the treatment of herpes virus infections of the skin or mucous
membranes in a mammal subject by topical administration of a therapeutically effective dose
thereof to the skin and/or mucous membrane of the mammal subject.
According to another aspect, the invention relates to a method of prophylactic and/or curative
treatment of herpes virus infections of the skin or mucous membranes in a mammal subject
comprising topical administration of a therapeutically effective dose of B-220 or a
pharmaceutically acceptable salt thereof.
In one embodiment, the method also comprises topical administration, in combination or in
sequence, of at least one additional pharmaceutically active ingredient suitable for topical
administration, e.g. selected from antiviral agents, antibiotics, anaesthetic agents, analgesic
agents, antiphlogistic agents, and anti-inflammatory agents.
Detailed description of the invention
B-220, i.e. 2,3-dimethyl(N,N-dimethylaminoethyl)-6H-indolo-(2,3-b)quinoxaline, has the
structural formula
and may be prepared e.g. as described in WO87/04436, the contents of which is incorporated
herein by reference.
Pharmaceutically acceptable salts of B-220 may be formed using any organic or inorganic,
pharmaceutically acceptable acid, such as are well-known to the person of ordinary skill in
the art. Pharmaceutically acceptable acid addition salts according to the invention are salts
that are safe and effective for topical use in mammals and that possess the desired biological
activity, e.g. hydrochloride, hydrobromide, hydroiodide, nitrate, sulfate, bisulfate, phosphate,
acid phosphate, isonicotinate, acetate, lactate, salicylate, citrate, tartrate, pantothenate,
bitartrate, ascorbate, succinate, maleate, gentisinate, fumarate, gluconate, glucaronate,
saccharate, for-
Claims (12)
1. The use of 2,3-dimethyl(N,N-dimethylaminoethyl)-6H-indolo-(2,3-b)quinoxaline or a pharmaceutically acceptable salt for the manufacturing of a medicament for use in the treatment of herpes virus infections of the skin or mucous membranes in a mammalian subject by topical administration of a therapeutically effective dose of said medicament to the skin or mucous membrane of the mammalian subject.
2. The use according to claim 1, wherein the medicament comprises 2,3-dimethyl(N,N- dimethylaminoethyl)-6H-indolo-(2,3-b)quinoxaline in an amount of 0.1-10% (w/w).
3. The use according to claim 1, wherein the medicament comprises 2,3-dimethyl(N,N- dimethylaminoethyl)-6H-indolo-(2,3-b)quinoxaline in an amount of 0.5-5% (w/w).
4. The use according to any one of the claims 1 to 3, wherein the medicament comprises at least one additional therapeutically active ingredient.
5. The use according to claim 4, wherein the additional therapeutically active ingredient is selected from antiviral agents, antibiotics, analgesics, anaesthetic agents, antiphlogistic agents and antiinflammatory agents.
6. The use according to claim 5, wherein the additional therapeutically active ingredient is an antiphlogistic agent.
7. The use according to claim 5, wherein the additional therapeutically active ingredient is an antiinflammatory agent.
8. The use according to any one of the claims 4 to 7, wherein the additional therapeutically active agent is present in an amount of 0.005-5% (w/w).
9. The use according to any one of the claims 1 to 8, wherein the medicament is for dermal or mucosal treatment.
10. The use according to any one of the claims 1 to 9, wherein the medicament is in the form of a cream, liquid, lotion, gel, spray, foam or ointment.
11. The use according to any one of the claims 1 to 9, wherein the medicament is for application using a patch, stick, spray dispenser, tube, or pen containing the medicament.
12. A use according to claim 1, substantially as herein described or exemplified.
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201161444275P | 2011-02-18 | 2011-02-18 | |
| EP20110154979 EP2489354A1 (en) | 2011-02-18 | 2011-02-18 | Pharmaceutical formulation of B220 for topical treatment of herpes |
| EP11154979.6 | 2011-02-18 | ||
| US61/444,275 | 2011-02-18 | ||
| PCT/EP2012/052763 WO2012110631A1 (en) | 2011-02-18 | 2012-02-17 | Pharmaceutical formulation for topical administration comprising b220 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NZ613313A NZ613313A (en) | 2015-06-26 |
| NZ613313B2 true NZ613313B2 (en) | 2015-09-29 |
Family
ID=
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