# US 5,700,679 A · Lipid vesicles having a bilayer containing a surfactant with anti-viral and spermicidal activity

> Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt

- Number: US 5,700,679 A
- Document ID: US5700679A
- Status: Granted
- Kind: A
- Application number: 08/661,051
- Filed: 1996-06-07
- Granted: 1997-12-23
- Earliest claimed: 1996-06-07
- Assignees: Novavax, Inc.
- Inventors: D. Craig Wright
- Web page: https://patentgrep.com/patent/US5700679A

## CPC

- C12N 7/00: Viruses; Bacteriophages; Compositions thereof; Preparation or purification thereof (preparing medicinal viral antigen or antibody compositions, e.g. virus vaccines, A61K39/00)
- A61K 9/0034: {Urogenital system, e.g. vagina, uterus, cervix, penis, scrotum, urethra, bladder; Personal lubricants}
- A61K 9/1272: comprising non-phosphatidyl surfactants as bilayer-forming substances, e.g. cationic lipids or non-phosphatidyl liposomes coated or grafted with polymers (lipids as modifying agents {A61K47/543})
- C12N 2740/16063: by chemical treatment
- Y10S 424/14: Topical contraceptives and spermacides
- C12N: MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA (microbiological testing media C12Q1/00)
- 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)
- Y10S: TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS

## Abstract

A novel formulation having anti-viral and spermicidal properties has been developed. The formulation contains lipid vesicles having an outer bilayer formed of a non-ionic amphiphile, a surfactant such as having spermicidal and/or anti-viral activity, an oil and a sterol. The selection of the components making the vesicle is such that the formulation provides rapid spermicidal or anti-viral activity. The formulation and methods of the invention are particularly useful in the mucous membranes such as the vaginal tract and has been tested against viruses such as HIV and Vaccinia.

## Claims

### Claim 1

A method of inactivating spermatozoa comprising the step of exposing said spermatozoa to a latex-compatible lipid vesicle formulation having topical spermicidal activity; said lipid vesicle formulation containing lipid vesicles having an outer bilayer wherein, said lipid vesicles include a non-ionic amphiphile, an oil, a sterol, and a spermicidal surfactant, wherein said lipid vesicles are formed primarily of said non-ionic amphiphile, wherein said non-ionic amphiphile, said oil and said spermicidal surfactant are selected such that said spermicidal surfactant is not dissolvable in said oil and at least a portion of said spermicidal surfactant is in the outer bilayer of said lipid vesicle.

### Claim 2 (depends on 1)

The method of claim 1 wherein said spermicidal surfactant has an average number of nine ethylene oxide units per molecule.

### Claim 3 (depends on 1)

The method of claim 1 wherein said non-ionic amphiphile is selected from the group consisting of POE ethers of fatty alcohols, POE esters of fatty acids, glycerol monolaurate, glycerol dilaurate, glycerol monostearate and glycerol distearate, and POE sorbitan fatty acid ethers.

### Claim 4 (depends on 1)

The method of claim 1 wherein said non-ionic amphiphile comprises glycerol monostearate.

### Claim 5 (depends on 1)

The method of claim 1 wherein said sterol is selected from the group consisting of cholesterol and phytosterols.

### Claim 6 (depends on 5)

The method of claim 5 wherein said sterol comprises soy sterol.

### Claim 7 (depends on 1)

The method of claim 1 wherein said oil comprises a vegetable oil.

### Claim 8 (depends on 7)

The method of claim 7 wherein said vegetable oil comprises soybean oil.

### Claim 9 (depends on 1)

The method of claim 1 wherein said lipid vesicle further comprises a charge producing agent.

### Claim 10 (depends on 9)

The method of claim 9 wherein said charge producing agent comprises a negative charge producing agent.

### Claim 11 (depends on 10)

The method of claim 10 wherein said negative charge producing agent comprises oleic acid.

### Claim 12 (depends on 1)

The method of claim 1 wherein said formulation further comprises a pharmaceutically acceptable carrier.

### Claim 13 (depends on 12)

The method of claim 12 wherein said formulation is in the form of a cream.

### Claim 14 (depends on 13)

The method of claim 13 wherein said formulation is used for vaginal insertion.

### Claim 15 (depends on 1)

The method of claim 1 wherein said formulation is coated on a condom.

### Claim 16

A method of inactivating an enveloped virus comprising the step of exposing said enveloped virus to a latex-compatible lipid vesicle formulation, said lipid vesicle formulation containing lipid vesicles having an outer bilayer wherein, said lipid vesicles include a non-ionic amphiphile, an oil, a sterol, and a nonoxyphenol surfactant, wherein said lipid vesicles are formed primarily of said non-ionic amphiphile, wherein said non-ionic amphiphile, said oil and said nonoxyphenol surfactant are selected such that said nonoxyphenol surfactant is not dissolvable in said oil and at least a portion of said nonoxyphenol surfactant is in the outer bilayer of said lipid vesicle.

### Claim 17 (depends on 16)

The method of claim 16 wherein said nonoxyphenol surfactant has an average number of nine ethylene oxide units per molecule.

### Claim 18 (depends on 16)

The method of claim 16 wherein said non-ionic amphiphile is selected from the group consisting of POE ethers of fatty alcohols, POE esters of fatty acids, glycerol monolaurate, glycerol dilaurate, glycerol monostearate and glycerol distearate, and POE sorbitan fatty acid ethers.

### Claim 19 (depends on 18)

The method of claim 18 wherein said non-ionic amphiphile comprises glycerol monostearate.

### Claim 20 (depends on 16)

The method of claim 16 wherein said sterol is selected from the group consisting of cholesterol and phytosterols.

### Claim 21 (depends on 20)

The method of claim 20 wherein said sterol comprises soy sterol.

### Claim 22 (depends on 16)

The method of claim 16 wherein said oil comprises a vegetable oil.

### Claim 23 (depends on 22)

The method of claim 22 wherein said vegetable oil comprises soybean oil.

### Claim 24 (depends on 16)

The method of claim 16 wherein said lipid vesicle further comprises a charge producing agent.

### Claim 25 (depends on 24)

The method of claim 24 wherein said charge producing agent comprises a negative charge producing agent.

### Claim 26 (depends on 25)

The method of claim 25 wherein said negative charge producing agent comprises oleic acid.

### Claim 27 (depends on 16)

The method of claim 16 wherein said formulation further comprises a pharmaceutically acceptable carrier.

### Claim 28 (depends on 27)

The method of claim 27 wherein said formulation is in the form of a cream.

### Claim 29 (depends on 28)

The method of claim 28 wherein said formulation is used for vaginal insertion.

### Claim 30 (depends on 16)

The method of claim 16 wherein said formulation is coated on a condom.

### Claim 31

A method of inactivating spermatozoa comprising the step of exposing said spermatozoa to a latex-compatible lipid vesicle formulation, said lipid vesicle formulation containing lipid vesicles having an outer bilayer, wherein said lipid vesicles include a non-ionic amphiphile, an oil, a sterol, and a nonoxyphenol surfactant, wherein said lipid vesicles are formed primarily of said non-ionic amphiphile, wherein said non-ionic amphiphile, said oil and said nonoxyphenol surfactant are selected such that said nonoxyphenol surfactant is not dissolvable in said oil and at least a portion of said nonoxyphenol surfactant is in the outer bilayer of said lipid vesicle.

### Claim 32 (depends on 31)

The method of claim 31 wherein said nonoxyphenol surfactant has an average number of nine ethylene oxide units per molecule.

### Claim 33 (depends on 31)

The method of claim 31 wherein said non-ionic amphiphile is selected from the group consisting of POE ethers of fatty alcohols, POE esters of fatty acids, glycerol monolaurate, glycerol dilaurate, glycerol monostearate and glycerol distearate, and POE sorbitan fatty acid ethers.

### Claim 34 (depends on 33)

The method of claim 33 wherein said non-ionic amphiphile comprises glycerol monostearate.

### Claim 35 (depends on 31)

The method of claim 31 wherein said sterol is selected from the group consisting of cholesterol and phytosterols.

### Claim 36 (depends on 35)

The method of claim 35 wherein said sterol comprises soy sterol.

### Claim 37 (depends on 31)

The method of claim 31 wherein said oil comprises a vegetable oil.

### Claim 38 (depends on 37)

The method of claim 37 wherein said vegetable oil comprises soybean oil.

### Claim 39 (depends on 31)

The method of claim 31 wherein said lipid vesicle further comprises a charge producing agent.

### Claim 40 (depends on 39)

The method of claim 39 wherein said charge producing agent comprises a negative charge producing agent.

### Claim 41 (depends on 40)

The method of claim 40 wherein said negative charge producing agent comprises oleic acid.

### Claim 42 (depends on 31)

The method of claim 31 wherein said formulation further comprises a pharmaceutically acceptable carrier.

### Claim 43 (depends on 42)

The method of claim 42 wherein said formulation is in the form of a cream.

### Claim 44 (depends on 43)

The method of claim 43 wherein said formulation is used for vaginal insertion.

### Claim 45 (depends on 31)

The method of claim 31 wherein said formulation is coated on a condom.

### Claim 46

A formulation for inactivating spermatozoa or enveloped viruses comprising a latex-compatible lipid vesicle formulation, wherein said lipid vesicle formulation includes lipid vesicles, wherein said vesicles include a non-ionic amphiphile, an oil, a sterol, and a nonoxyphenol surfactant, wherein said lipid vesicles are formed primarily of said non-ionic amphiphile, wherein said non-ionic amphiphile, said oil and said nonoxyphenol surfactant are selected such that said nonoxyphenol surfactant is not dissolvable in said oil and at least a portion of said nonoxyphenol surfactant is in the outer bilayer of said lipid vesicle.

### Claim 47 (depends on 46)

The formulation of claim 46 wherein said nonoxyphenol surfactant has an average number of nine ethylene oxide units per molecule.

### Claim 48 (depends on 46)

The formulation of claim 46 wherein said non-ionic amphiphile is selected from the group consisting of POE ethers of fatty alcohols, POE esters of fatty acids, glycerol monolaurate, glycerol dilaurate, glycerol monostearate and glycerol distearate, and POE sorbitan fatty acid ethers.

### Claim 49 (depends on 48)

The formulation of claim 48 wherein said non-ionic amphiphile comprises glycerol monostearate.

### Claim 50 (depends on 46)

The formulation of claim 46 wherein said sterol is selected from the group consisting of cholesterol and phytosterols.

### Claim 51 (depends on 50)

The formulation of claim 50 wherein said sterol comprises soy sterol.

### Claim 52 (depends on 46)

The formulation of claim 46 wherein said oil comprises a vegetable oil.

### Claim 53 (depends on 52)

The formulation of claim 52 wherein said vegetable oil comprises soybean oil.

### Claim 54 (depends on 46)

The formulation of claim 46 wherein said lipid vesicles further comprises a charge producing agent.

### Claim 55 (depends on 54)

The formulation of claim 54 whereto said charge producing agent comprises a negative charge producing agent.

### Claim 56 (depends on 55)

The formulation of claim 55 wherein said negative charge producing agent comprises oleic acid.

### Claim 57 (depends on 46)

The formulation of claim 46 wherein said formulation further comprises a pharmaceutically acceptable carrier.

### Claim 58 (depends on 57)

The formulation of claim 57 wherein said formulation is in the form of a cream.

### Claim 59 (depends on 58)

The formulation of claim 58 wherein said formulation is suitable for vaginal insertion.

### Claim 60 (depends on 46)

The formulation of claim 46 wherein said formulation is suitable for coating on a condom.

### Claim 61 (depends on 46)

A condom having a coating with spermicide or enveloped virus inactivating activity, said condom having the formulation of claim 46.