# US 9,433,589 B2 · Injectable pharmaceutical compositions comprising adrenaline and citric acid

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- Number: US 9,433,589 B2
- Document ID: US9433589B2
- Status: Granted
- Kind: B2
- Application number: 14/898,573
- Filed: 2014-06-17
- Published: 2016-04-28
- Granted: 2016-09-06
- Earliest claimed: 2013-06-17
- Assignees: Rigshospitalet
- Applicants: Rigshospitalet
- Inventors: Philip Hansen; Pär Johansson; Jens Kindtler
- Web page: https://patentgrep.com/patent/US9433589B2

## CPC

- A61K 31/137: Arylalkylamines, e.g. amphetamine, epinephrine, salbutamol, ephedrine {or methadone}
- A61K 9/0019: {Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner (non-active ingredients are additionally classified in A61K47/00)}
- A61K 31/194: having two or more carboxyl groups, e.g. succinic, maleic or phthalic acid
- A61K 47/02: Inorganic compounds
- A61K 47/12: Carboxylic acids; Salts or anhydrides thereof
- A61K 47/22: Heterocyclic compounds, e.g. ascorbic acid, tocopherol or pyrrolidones
- A61P 7/04: Antihaemorrhagics; Procoagulants; Haemostatic agents; Antifibrinolytic agents
- 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

The present invention relates to injectable pharmaceutical compositions showing improved storage stability said compositions comprising adrenaline and citric acid showing improved storage stability.

## Claims

### Claim 1

An injectable pharmaceutical composition comprising:
I: (a) 0.2-50 μg/ml adrenaline, and
(b) citric acid, and
(c) no lidocaine and no amino acid.

### Claim 2 (depends on 1)

The composition according to claim 1, wherein the concentration of adrenaline lies in the range of 0.5-10 μg/ml adrenaline.

### Claim 3 (depends on 1)

The composition according to claim 1, wherein the concentration of citric acid lies in the range of 0.1-100 mM.

### Claim 4 (depends on 1)

The composition according to claim 1, wherein the solution pH lies in the range of 2.5-3.5.

### Claim 5 (depends on 1)

The composition according to claim 1 comprising 2 μg/ml adrenaline, 2.4 mM citric acid and where the solution pH is 3.

### Claim 6 (depends on 1)

The composition according to claim 1, wherein the composition further comprises Na-metabisulfite and where the concentration of Na-metabisulfite is no more than 100 μg/ml.

### Claim 7 (depends on 1)

The composition according to claim 1, wherein the composition further comprises NaCl and where the concentration of NaCl is no more than 100 μg/ml.

### Claim 8 (depends on 1)

The composition according to claim 1 further comprising an antioxidant.

### Claim 9 (depends on 1)

The composition according to claim 1 further comprising a chelating agent.

### Claim 10 (depends on 1)

The composition according to claim 1, wherein the composition is formulated as an injectable solution.

### Claim 11 (depends on 1)

The composition according to claim 1 further comprising an excipient approved for use in formulation for use as intravenous solutions.

### Claim 12 (depends on 1)

The composition according to claim 1 which has storage stability of greater than 95% stable at 3 months at 25 degrees Celsius.

### Claim 13 (depends on 1)

A method of treating an adrenaline-requiring condition in a mammalian subject in need thereof, said method comprising administering an effective therapeutic amount of the composition according to claim 1 to the mammalian subject.

### Claim 14 (depends on 13)

The method according to claim 13, wherein the adrenaline-requiring condition is selected from the group consisting of coagulation disorder, bleeding, and bleeding caused by tissue damage or surgical procedure.

### Claim 15 (depends on 13)

The method according to claim 13, wherein the mammalian subject is a human.

### Claim 16 (depends on 13)

The method according to claim 13, wherein the composition is administered parenterally resulting in a systemic concentration of adrenaline.

### Claim 17 (depends on 13)

The method according to claim 13, wherein the composition comprises 0.2-50 μg/ml adrenaline and 0.1 to 100 mM citric acid, said composition having a pH in the range of 2.5-3.5.