# US 2011/0003015 A1 · Stabilized composition comprising at least one adrenergic compound

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- Number: US 2011/0003015 A1
- Document ID: US20110003015A1
- Status: Published application
- Kind: A1
- Application number: 12/794,163
- Filed: 2010-06-04
- Published: 2011-01-06
- Earliest claimed: 2009-06-04
- Assignees: Alk AG
- Inventors: Alan J. Baillie; Kenneth MacDonald; Pamela Porteous; Simon Hendry
- Web page: https://patentgrep.com/patent/US20110003015A1

## CPC

- A61K 45/06: Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
- A61K 31/137: Arylalkylamines, e.g. amphetamine, epinephrine, salbutamol, ephedrine {or methadone}
- A61K 33/04: Sulfur, selenium or tellurium; Compounds thereof
- A61P 37/08: Antiallergic agents (antiasthmatic agents A61P11/06; ophthalmic antiallergics A61P27/14)
- A61P 39/06: Free radical scavengers or antioxidants
- A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

A stabilised composition comprising at least one adrenergic compound and at least one antioxidant selected from the group consisting of a bisulfate, a metabisulfite and a sulfite compound.

## Claims

### Claim 1

A liquid pharmaceutical composition comprising an adrenergic compound and at least one antioxidant selected from the group consisting of a bisulfite, a metabisulfite and a sulfite compound, wherein the molar ratio of the adrenergic compound to the at least one antioxidant, measured as sulfite-equivalents, is in the range 1.31-2.20, and wherein the pH of said liquid composition is in the range of about 2.0-5.0.

### Claim 2 (depends on 1)

The pharmaceutical composition according to claim 1, wherein the adrenergic compound is selected from the group consisting of epinephrine, norepinephrine, phenylephrine, α-methylnorepinephrine, dopamine, methoxamine, clonidine, dobutamine, prenalterol, isoproterenol, fenoterol, albuterol, terbutaline, metaproterenol, and physiologically acceptable salts thereof.

### Claim 3 (depends on 1)

The pharmaceutical composition according to claim 1, wherein the adrenergic compound is selected from the group consisting of epinephrine, norepinephrine, isoproterenol and dopamine, and physiologically acceptable salts thereof.

### Claim 4 (depends on 1)

The pharmaceutical composition according to claim 1, wherein the adrenergic compound is epinephrine or a physiologically acceptable salt thereof.

### Claim 5 (depends on 1)

The pharmaceutical composition according to claim 1, wherein the antioxidant is selected from the group consisting of sodium bisulfite and sodium metabisulfite.

### Claim 6 (depends on 5)

The pharmaceutical composition according to claim 5, wherein the antioxidant is sodium metabisulfite.

### Claim 7 (depends on 1)

The pharmaceutical composition according to claim 1, wherein the molar ratio of the at least one adrenergic compound to the at least one antioxidant is in the range of 1.31 to 2.00.

### Claim 8 (depends on 1)

The pharmaceutical composition according to claim 1, having a pH in the range of 2.5-4.5.

### Claim 9 (depends on 8)

The pharmaceutical composition according to claim 8, wherein the pH is in the range of 3.3-3.5.

### Claim 10 (depends on 1)

The pharmaceutical composition according to claim 1, further comprising one or more excipients or additives.

### Claim 11 (depends on 2)

The pharmaceutical composition according to claim 2, comprising:
Epinephrine acid tartrate
2.0
mg/ml
Sodium chloride
6.0
mg/ml
Sodium metabisulfite
0.57
mg/ml
HCl/NaoH
q.s. pH 3.4
Water for injection
q.s. 1.0
ml

### Claim 12

A method for stabilizing a liquid pharmaceutical composition comprising an adrenergic compound, comprising the steps of i) providing a solution of an adrenergic compound, ii) adding at least one antioxidant selected from the group consisting of a bisulfite, a metabisulfite, and a sulfite compound, iii) adjusting the pH of the composition to a value in the range 2.0-5.0 optionally by addition of an acid or a base, wherein the molar ratio of the adrenergic compound to the at least one antioxidant, measured as sulfite-equivalents, is in the range 1.31-2.20.

### Claim 13

(canceled)

### Claim 14

A kit comprising:
v) a liquid pharmaceutical composition comprising an adrenergic compound and at least one antioxidant selected from the group consisting of a bisulfite, a metabisulfite and a sulfite compound, wherein the molar ratio of the adrenergic compound to the at least one antioxidant, measured as sulfite-equivalents, is in the range 1.31-2.20, and wherein the pH of said liquid composition is in the range of about 2.0-5.0, and
vi) an administration device.

### Claim 15 (depends on 14)

The kit according to claim 14 wherein the administration device is an ampoule or an auto-injector.

### Claim 16

A method of improving at least one symptom of a medical condition requiring an adrenergic compound in an individual in need thereof, comprising administering to the individual a liquid pharmaceutical composition comprising an adrenergic compound and at least one antioxidant selected from the group consisting of a bisulfite, a metabisulfite and a sulfite compound, wherein the molar ratio of the adrenergic compound to the at least one antioxidant, measured as sulfite-equivalents, is in the range 1.31-2.20, and wherein the pH of said liquid composition is in the range of about 2.0-5.0.

### Claim 17

A method of treating anaphylaxis in an individual comprising administering to the individual a liquid pharmaceutical composition comprising an adrenergic compound and at least one antioxidant selected from the group consisting of a bisulfite, a metabisulfite and a sulfite compound, wherein the molar ratio of the adrenergic compound to the at least one antioxidant, measured as sulfite-equivalents, is in the range 1.31-2.20, and wherein the pH of said liquid composition is in the range of about 2.0-5.0.

### Claim 18

A liquid pharmaceutical composition for use in improving at least one symptom of a medical condition requiring an adrenergic compound in an individual in need thereof, comprising an adrenergic compound and at least one antioxidant selected from the group consisting of a bisulfite, a metabisulfite and a sulfite compound, wherein the molar ratio of the adrenergic compound to the at least one antioxidant, measured as sulfite-equivalents, is in the range 1.31-2.20, and wherein the pH of said liquid composition is in the range of about 2.0-5.0.

### Claim 19

(canceled)