CN1507858A - Flrorinated chloromycetin containing liquid preparation for animal - Google Patents
Flrorinated chloromycetin containing liquid preparation for animal Download PDFInfo
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- CN1507858A CN1507858A CNA031210724A CN03121072A CN1507858A CN 1507858 A CN1507858 A CN 1507858A CN A031210724 A CNA031210724 A CN A031210724A CN 03121072 A CN03121072 A CN 03121072A CN 1507858 A CN1507858 A CN 1507858A
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Abstract
The present invention relates to an animal preparation containing fluorochloromycin. In its formula the nonsteroid inflammation-resisting medicine or other antimicrobial medicine can be added, and the physical and chemical properties of said invented preparation are stable. The storage time of said injection prepared by using glycerin triacetate as main medium can be up to above 3 years, and the storage time of the preparation containing hydrated nonionic surfactant can be up to above 2 years. Said invention is high in biological utilization rate, and has slow-release action.
Description
Technical field
The present invention is a kind of veterinary formulations, and the liquid preparation for animals of fluorinated chloromycetin specifically, said preparation can be oral, injectable, also can adopt the dabbling method administration in breast perfusion or uterus, are used for mastitis or metritic control.
Background technology
Fluorinated chloramphenicol claims Florfenicol or florfenicol (Florfenicol) again, is the chemical improvement product of chloromycetin.As extensive pedigree antibiotic, be widely used in veterinary clinic.The veterinary formulations of fluorinated chloromycetin has the injection of powder for oral administration and liquid preparation and parenterai administration.Existing commercially available injection is with N-methyl-ketopyrrolidine and PEG and 1, organic solvents such as 2-propylene glycol are the injection of disperse medium preparation, concrete preparation method is in the existing description of patent CN1041793C, percent by volume is calculated by weight, contain the PEG/1 about 40% in the preparation, the 2-propylene glycol, about 30% ketopyrrolidine kind solvent (as N-methyl-ketopyrrolidine).Experiment shows, under the situation that does not have a certain amount of water to exist, in the preparation 1, the 2-propylene glycol, the concentration of ketopyrrolidine kind solvent is higher than at 30% o'clock and can causes injection site inflammation or other tissue injury, the addition of PEG in preparation generally also can not surpass 40%, otherwise, can cause injection site inflammation or other tissue injury equally, thereby influence its effective bioavailability, therefore, the tissue injury to the injection site when the clinical practice is inevitably with the injection of above several organic solvent combined preparation, and it is inevitable [Jiang Hongxia etc. equally that bioavailability is subjected to certain restriction, China veterinary journal, 21 (1): 86-89].Experiment shows, forms 1 of injection when substituting with water or glycerol triacetate, and during 2-propylene glycol/PEG, its stimulation to the injection site can significantly reduce, and can improve bioavailability of medicament.
The present invention is exactly with water and/or nonionic surfactant or glycerol triacetate replacement 1,2-propylene glycol, PEG, preparation significantly reduces the zest of injection site, the bioavailability height, slow release effect is good, and in preparation, add NSAID (non-steroidal anti-inflammatory drug), be better than single agent of fluorinated chloromycetin for the improvement of clinical symptoms (as heating, pain, inflammation etc.).
The physicochemical character of preparation of the present invention is stable, is that its storage life of injection that main medium prepares can reach more than 3 years by glycerol triacetate or water.The injection of moisture and nonionic surfactant, its storage life can reach more than 2 years.
The fluorinated chloramphenicol that the present invention is used has more detailed description in United States Patent (USP) 4235892.The nonsteroidal antiinflammatory drug that adds in the compound preparation all has introduction (Zhang Wen Sheng, Li Anliang chief editor, pharmaceutical chemistry, Higher Education Publishing House, 1999 years, 348-375 page or leaf) in the most basic pharmaceutical chemistry is taught book and relevant monograph.The preferred nonsteroidal anti-inflammatory drug of the present invention comprises: indomethacin indomethacin, ketoprofen ketoprofen, meloxicam meloxican, naproxen naproxen, Carprofen caprofen, ketorolac ketorolac, flunixin flunixin, diclofenac diclofenac, piroxicam piroxican.The antimicrobial agents that can add in the compound preparation comprises: but macrolide antibiotics, woods amine antibiotic, polypeptide antibiotics, aminoglycoside antibiotics, tetracycline antibiotics, sulfonamides antibiotic, quinolone antibiotic, relevant these antibiotic are at Zhang Zhongqiu, the Zheng Ming chief editor " holds fowl drug use handbook (China Agricultyre University Press, 2000, the 31-75 page or leaf) and in " national essential drugs " (People's Health Publisher, 38-86 page or leaf in 1999) detailed introduction is arranged.
Summary of the invention
Preparation of the present invention consists of:
Prescription (1):
A. fluorinated chloramphenicol 1-40% (W/V)
B. NSAID (non-steroidal anti-inflammatory drug) and antimicrobial agents 0-20% (W/V)
C. cosolvent 0-60% (V/V)
D. suspending agent 0-10% (W/V)
E. glycerol triacetate adds to 100% (V/V)
Prescription (2):
A. fluorinated chloramphenicol 1-20% (W/V)
B. non-ionic surface active agent 1-40% (W/V)
C. water adds to 100% (V/V)
D. in case of necessity, can add other auxiliary agent (as cosolvent, suspending agent and oil phase substance).
E. in case of necessity, can add NSAID (non-steroidal anti-inflammatory drug).
Prescription (3):
A. fluorinated chloramphenicol 5-30% (W/V)
B. nonsteroidal anti-inflammatory drug and antimicrobial agents 0-15% (W/V)
C. dimethyl acetylamide or N-methyl-ketopyrrolidine 5-55% (V/V)
D. water adds to 100% (V/V)
Described cosolvent comprises dimethyl acetylamide, formal glycerine, pyrrolidones, and preferred dimethyl acetylamide or N-methyl-ketopyrrolidine and glycerol triacetate are formed cosolvent.Described ionic surfactant comprises polyoxyethylene sorbitan fatty acid ester, sorbitan fatty acid ester class, alkylphenol polyoxyethylene class, Oleum Ricini glymes, preferred Tween-80, Span-80.Described suspending agent and oil phase substance are vegetable oil, hydrogenated vegetable oil and glycerine fatty acid ester type compound, preferred castor oil hydrogenated (hydrogenated castor oil is hereinafter to be referred as HCO).
The preferred preparation of the present invention consists of:
Prescription (1):
A. fluorinated chloramphenicol 20-40% (W/V)
B. diclofenac 0-5% (W/V)
C. dimethyl acetylamide or N-methyl-ketopyrrolidine 0-40% (V/V)
D. glycerol triacetate adds to 100% (V/V)
Prescription (2):
A. fluorinated chloramphenicol 10-40% (W/V)
B. ketoprofen 0-4% (W/V)
C. dimethyl acetylamide or N-methyl-ketopyrrolidine 0-40% (V/V)
D. glycerol triacetate adds to 100% (V/V)
Prescription (3):
A. fluorinated chloramphenicol 5-15% (W/V)
b.Span-80 5-25％(V/V)
c.Tween-80 5-25％(V/V)
d.HCO 0.2-8％(W/V)
E. dimethyl acetylamide 5-20% (V/V)
F. water adds to 100% (V/V)
Prescription (4):
A. fluorinated chloramphenicol 5-25% (W/V)
B. nonsteroidal anti-inflammatory drug 0-15% (W/V)
C.OP-10 or EL-20 or Tween-80 8-40% (V/V)
D. dimethyl acetylamide or N-methyl-ketopyrrolidine 20-50% (V/V)
E. water adds to 100% (V/V)
Prescription (5):
A. fluorinated chloramphenicol 15-25% (W/V)
B. ketoprofen 2-5% (V/V)
C. dimethyl acetylamide or N-methyl-ketopyrrolidine 35-55% (V/V)
D. water adds to 100% (V/V)
The further preparation of optimizing of preparation that the present invention contains surfactant consists of:
Prescription (1):
A. fluorinated chloramphenicol 10% (W/V)
b.Span-80 13％(V/V)
c.Tween-80 13％(V/V)
d.HCO 1-4％(W/V)
E. dimethyl acetylamide 6% (V/V)
F. water adds to 100% (V/V)
Prescription (2):
A. fluorinated chloramphenicol 20% (W/V)
B.OP-10 or EL-20 or Tween-80 20% (V/V)
C. dimethyl acetylamide 41% (V/V)
D. water adds to 100% (V/V)
Prescription (3):
A. fluorinated chloramphenicol 20% (W/V)
B. ketoprofen 2-3% (W/V)
C. dimethyl acetylamide 50% (V/V)
D. water adds to 100% (V/V)
The present invention is special, and preparation and the preparation method of selecting is:
Preparation (1): a. fluorinated chloramphenicol 10-15% (W/V)
B. ketoprofen 2-5% (W/V)
c.TPM 5％(W/V)
D. dimethyl acetylamide or N-Methyl pyrrolidone 35-65% (V/V)
E. water adds to 100% (V/V)
Preparation (2): a. fluorinated chloramphenicol 10% (W/V)
B. ketoprofen 0-3% (W/V)
C. dimethyl acetylamide or N-Methyl pyrrolidone 10-20% (V/V)
D.1,2-propylene glycol, glycerol or formal glycerine 35-65% (V/V)
E. water adds to 100% (V/V)
F. add other auxiliary agent (as suspending agent, surfactant) in case of necessity
G. also can add other antibacterials in the prescription, form compound preparation
The preparation method of preparation (2): active ingredient is dissolved with dimethyl acetylamide or N-Methyl pyrrolidone, be prepared into supersaturated solution, add polyethylene again than pyrrolidone (suspending agent), after the dissolving, under stirring condition, mix with water, after treating that crystallize is finished, homogenize, add remaining media and auxiliary agent again to final volume.
The specific embodiment
With example preparation of the present invention is described below, but example do not limit the scope of the invention, scope of the present invention and core content are determined according to claims.
Example 1
This example is the injection of preparation fluorinated chloramphenicol 30%.
Fluorinated chloramphenicol 30% (W/V)
Dimethyl acetylamide 30% (V/V)
Glycerol triacetate adds to 100% (V/V)
Example 2
This example is the injection of preparation fluorinated chloramphenicol 30%, ketoprofen 4%.
Fluorinated chloramphenicol 30% (W/V)
Ketoprofen 4% (W/V)
N-methyl-ketopyrrolidine 30% (V/V)
Glycerol triacetate adds to 100% (V/V)
Example 3
This example is the injection of preparation fluorinated chloramphenicol 5%, ketoprofen 0.6%.
Fluorinated chloramphenicol 5% (W/V)
Ketoprofen 0.6% (W/V)
Dimethyl acetylamide 5% (V/V)
Glycerol triacetate adds to 100% (V/V)
Example 4
This example is the injection of preparation fluorinated chloramphenicol 10%.
A. fluorinated chloramphenicol 10% (W/V)
b.Span-80 13％(V/V)
c.Tween-80 13％(V/V)
d?HCO 1-4％(W/V)
E dimethyl acetylamide 6% (V/V)
F water adds to 100% (V/V)
Example 5
This example is the injection of preparation fluorinated chloramphenicol 25%.
Fluorinated chloramphenicol 25% (W/V)
Dimethyl acetylamide 53% (V/V)
Water adds to 100% (V/V)
Example 6
This example is the injection of preparation fluorinated chloramphenicol 20%.
Fluorinated chloramphenicol 20% (W/V)
EL-20 20％(W/V)
Dimethyl acetylamide 40% (V/V)
Water adds to 100% (V/V)
Example 7
This example is the injection of preparation fluorinated chloramphenicol 40%.
Fluorinated chloramphenicol 40% (W/V)
Ketoprofen 4% (W/V)
HCO 0.2-3％(W/V)
Formal glycerine 20% (V/V)
Glycerol triacetate adds to 100% (V/V)
Example 8,
This example is the suspension of preparation fluorinated chloramphenicol 10%.
Get the 2g fluorinated chloramphenicol, add the 1ml dimethyl acetylamide, heating for dissolving adds 1g PVP-K30, and dissolving adds 8ml water and stirs, and is mixed, and adds 6ml water and 2ml glycerol again, promptly gets the suspension that contains 10% fluorinated chloramphenicol.
This preparation can be oral, can subcutaneous or intramuscular injection, also can carry out uterus or breast perfusion, and be used to prevent and treat in the animal uterus and infect or mastitis.When the salient point that this preparation is better than existing preparation is under the percutaneous drug administration by injection, have slow release effect and very little, be better than existing preparation the injection site tissue damage.Can add other antibiotic in this preparation, effective, the preferred polymyxin of the antimicrobial agents that can add, Roxithromycin, TMP, tylosin and derivant and quinolones.
Example 9,
This example is the suspension of preparation fluorinated chloramphenicol 15%.
Get the 1.5g fluorinated chloramphenicol, 1.5g PEG 8000 adds 2.5-3ml acetone, heating for dissolving, steam except that behind the part acetone, liquid is chilled to about 30 ℃, under agitation, add 5ml water, after treating that crystallize is finished, acetone is removed in decompression, adds 0.2ml Tween-80, add water to 10ml, promptly get the suspension that contains 15% fluorinated chloramphenicol.This agent injectable also can be through the uterus or the breast perfusion administration, is used for the treatment of animal uterus inflammation or mastitis.
Example 10,
This example is the suspension of preparation fluorinated chloramphenicol 20%.
Get 2g fluorinated chloramphenicol micropowder (fineness is less than 100 μ m), add 0.4ml Tween-80, the aqueous solution that contains 1g PEG 8000 in adding promptly gets the suspension that contains 20% fluorinated chloramphenicol to 10ml.This agent injectable also can be through the uterus or the breast perfusion administration, is used for the treatment of animal uterus inflammation or mastitis.
Claims (10)
1, the compound injection of a kind of fluorinated chloromycetin and nonsteroidal anti-inflammatory drug is characterized in that preparation consists of:
A. fluorinated chloramphenicol 1-35% (W/V)
B. NSAID (non-steroidal anti-inflammatory drug) 1-20% (W/V)
C. disperse medium and auxiliary agent add to 100% (V/V)
2, a kind of veterinary formulations of fluorinated chloromycetin is characterized in that preparation consists of:
A. fluorinated chloramphenicol 1-40% (W/V)
B. NSAID (non-steroidal anti-inflammatory drug) 0-20% (W/V)
C. cosolvent 0-60% (V/V)
D. suspending agent 0-10% (W/V)
E. glycerol triacetate adds to 100% (V/V)
3, by claim 1 and 2 described preparations, it is characterized in that described cosolvent comprises dimethyl acetylamide, formal glycerine, pyrrolidones.Preferred dimethyl acetylamide or N-methyl-ketopyrrolidine and glycerol triacetate are formed cosolvent, are used to prepare claim 1 and 2 described preparations.Preferred hydrogenated vegetable oil, molecular weight are suspending agent greater than 1000 Polyethylene Glycol (PEG), polyvinylpyrrolidone (PVP), are used to prepare claim 1 and 2 described preparations.
4, by claim 1 and 2 described preparations, it is characterized in that preferred preparation consists of:
Prescription (1):
A. fluorinated chloramphenicol 20-40% (W/V)
B. diclofenac 0-5% (W/V)
C. dimethyl acetylamide or N-methyl-ketopyrrolidine 5-40% (V/V)
D. glycerol triacetate adds to 100% (V/V)
Prescription (2):
A. fluorinated chloramphenicol 10-40% (W/V)
B. ketoprofen 0-4% (W/V)
C. dimethyl acetylamide or N-methyl-ketopyrrolidine 5-40% (V/V)
D. glycerol triacetate adds to 100% (V/V)
5, based on the veterinary formulations of the fluorinated chloromycetin of surfactant and water, it is characterized in that preparation consists of:
A. fluorinated chloramphenicol 1-20% (W/V)
B. non-ionic surface active agent 1-40% (V/V)
C. water adds to 100% (V/V)
D. in case of necessity, can add other auxiliary agent (as cosolvent, suspending agent and oil phase substance).
E. in case of necessity, can add NSAID (non-steroidal anti-inflammatory drug).
6, by the described preparation of claim 5, it is characterized in that described nonionic surfactant comprises polyoxyethylene sorbitan fatty acid ester, sorbitan fatty acid ester class, alkylphenol polyoxyethylene class, Oleum Ricini glymes, preferred Tween-80, Span-80.Described cosolvent is dimethyl acetylamide, N-N-methyl-2-2-pyrrolidone N-, described suspending agent and oil phase substance are vegetable oil, hydrogenated vegetable oil and glycerine fatty acid ester type compound, preferred castor oil hydrogenated (hydrogenated castor oil is hereinafter to be referred as HCO).
7, described by claim 5-6, it is characterized in that preferred preparation consists of:
Prescription (1):
A. fluorinated chloramphenicol 5-15% (W/V)
b.Span-80 5-25％(V/V)
c.Tween-80 5-25％(V/V)
d.HCO 0.2-8％(W/V)
E. dimethyl acetylamide 5-20% (V/V)
F. water adds to 100% (V/V)
Prescription (2):
A. fluorinated chloramphenicol 5-25% (W/V)
B. NSAID (non-steroidal anti-inflammatory drug) or antimicrobial agents 5-15% (W/V)
C.OP-10 or EL-20 or Tween-80 8-40% (V/V)
D. dimethyl acetylamide or N-methyl-ketopyrrolidine 10-30% (V/V)
E. water adds to 100% (V/V)
8, a kind of veterinary formulations of fluorinated chloromycetin is characterized in that the disperse medium of preparation is made up of water and organic liquid medium, and it is as follows specifically to fill a prescription:
A, fluorinated chloramphenicol 5-30% (W/V)
B, nonsteroidal anti-inflammatory drug or other antimicrobial agents 0-15% (W/V)
C, dimethyl acetylamide or N-methyl-ketopyrrolidine 0-55% (V/V)
D, water add to 100% (V/V)
E, in case of necessity adds glycerol or 1, and 2-propylene glycol and molecular weight are greater than 1000 PEG or PVP.
9, by the described preparation of claim 8, it is characterized in that preferred preparation consists of:
A, fluorinated chloramphenicol 10-25% (W/V)
B, ketoprofen 2-5% (W/V)
c、TMP 5％(W/V)
D, dimethyl acetylamide or N-methyl-ketopyrrolidine 35-55% (V/V)
E, water add to 100% (V/V)
10, by the described preparation of claim 8, it is characterized in that preferred preparation consists of and preparation method is as follows:
(1) preparation is formed:
A, fluorinated chloramphenicol 10-20% (W/V)
B, ketoprofen 0-3% (W/V)
C, dimethyl acetylamide 0-20% (V/V)
D, 1,2-propylene glycol, glycerol or formal glycerine 0-30% (V/V)
E, water add to 100% (V/V)
F, in case of necessity adds other auxiliary agent, as suspending agent, surfactant;
Also can add other antibacterials in g, the prescription, form compound preparation.
(2) preparation method: method a, with active ingredient with the dissolving of dimethyl acetylamide or N-Methyl pyrrolidone, be prepared into supersaturated solution, add or do not add polyvinylpyrrolidone (suspending agent), under stirring condition, mix with water, homogenize, add remaining media and auxiliary agent to final volume.Method b, fluorinated chloramphenicol is dissolved under heating condition with acetone, adds PEG 4000-20000, after the fusing, add water, treat that the fluorinated chloramphenicol crystallite is separated out after, acetone is removed in decompression, homogenizes, and adds remaining media and auxiliary agent to final volume.Method c, get fluorinated chloramphenicol micropowder (fineness is less than 100 μ m), add or do not add non-ionic surface active agent, add contain suspending agent aqueous solution to final volume, promptly get the suspension of fluorinated chloromycetin.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNA031210724A CN1507858A (en) | 2002-12-19 | 2003-03-24 | Flrorinated chloromycetin containing liquid preparation for animal |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN02156694.1 | 2002-12-19 | ||
| CN02156694 | 2002-12-19 | ||
| CNA031210724A CN1507858A (en) | 2002-12-19 | 2003-03-24 | Flrorinated chloromycetin containing liquid preparation for animal |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN1507858A true CN1507858A (en) | 2004-06-30 |
Family
ID=34276111
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNA031210724A Pending CN1507858A (en) | 2002-12-19 | 2003-03-24 | Flrorinated chloromycetin containing liquid preparation for animal |
Country Status (1)
| Country | Link |
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Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101843586A (en) * | 2010-04-29 | 2010-09-29 | 山东迅达康兽药有限公司 | Water-soluble micro powder containing florfenicol and preparation method thereof |
| US8034845B2 (en) | 2003-05-29 | 2011-10-11 | Intervet Inc. | Compositions and method for treating infection in cattle and swine |
| US8044230B2 (en) | 2006-12-13 | 2011-10-25 | Intervet Inc. | Water-soluble prodrugs of chloramphenicol, thiamphenicol, and analogs thereof |
| US8314252B2 (en) | 2008-07-30 | 2012-11-20 | Intervet Inc. | Process for preparing oxazoline-protected aminodiol compounds useful as intermediates to florfenicol |
| CN104188901A (en) * | 2014-08-12 | 2014-12-10 | 河南迪冉生物科技有限公司 | Florfenicol injection for livestock and preparation method thereof |
| CN104394848A (en) * | 2012-06-27 | 2015-03-04 | Xeris药物公司 | Stable formulations for parenteral injection of small molecule drugs |
| US9642894B2 (en) | 2013-02-06 | 2017-05-09 | Xeris Pharmaceuticals, Inc. | Compositions for rapidly treating severe hypoglycemia |
| US9649364B2 (en) | 2015-09-25 | 2017-05-16 | Xeris Pharmaceuticals, Inc. | Methods for producing stable therapeutic formulations in aprotic polar solvents |
| US10987399B2 (en) | 2011-03-10 | 2021-04-27 | Xeris Pharmaceuticals, Inc. | Stable formulations for parenteral injection of peptide drugs |
| US11020403B2 (en) | 2017-06-02 | 2021-06-01 | Xeris Pharmaceuticals, Inc. | Precipitation resistant small molecule drug formulations |
| US11129940B2 (en) | 2014-08-06 | 2021-09-28 | Xeris Pharmaceuticals, Inc. | Syringes, kits, and methods for intracutaneous and/or subcutaneous injection of pastes |
| US11590205B2 (en) | 2015-09-25 | 2023-02-28 | Xeris Pharmaceuticals, Inc. | Methods for producing stable therapeutic glucagon formulations in aprotic polar solvents |
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2003
- 2003-03-24 CN CNA031210724A patent/CN1507858A/en active Pending
Cited By (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9084719B2 (en) | 2003-05-29 | 2015-07-21 | Intervet Inc. | Compositions and method for treating infection in cattle and swine |
| US8034845B2 (en) | 2003-05-29 | 2011-10-11 | Intervet Inc. | Compositions and method for treating infection in cattle and swine |
| US8044230B2 (en) | 2006-12-13 | 2011-10-25 | Intervet Inc. | Water-soluble prodrugs of chloramphenicol, thiamphenicol, and analogs thereof |
| US8314252B2 (en) | 2008-07-30 | 2012-11-20 | Intervet Inc. | Process for preparing oxazoline-protected aminodiol compounds useful as intermediates to florfenicol |
| CN101843586B (en) * | 2010-04-29 | 2012-05-23 | 山东迅达康兽药有限公司 | Water-soluble micro powder containing florfenicol and preparation method thereof |
| CN101843586A (en) * | 2010-04-29 | 2010-09-29 | 山东迅达康兽药有限公司 | Water-soluble micro powder containing florfenicol and preparation method thereof |
| US10987399B2 (en) | 2011-03-10 | 2021-04-27 | Xeris Pharmaceuticals, Inc. | Stable formulations for parenteral injection of peptide drugs |
| US10765683B2 (en) | 2012-06-27 | 2020-09-08 | Xeris Pharmaceuticals, Inc. | Stable formulations for parenteral injection of small molecule drugs |
| CN104394848B (en) * | 2012-06-27 | 2017-12-01 | Xeris药物公司 | The stabilization formulations for parental injection of small-molecule drug |
| CN104394848A (en) * | 2012-06-27 | 2015-03-04 | Xeris药物公司 | Stable formulations for parenteral injection of small molecule drugs |
| US11446310B2 (en) | 2012-06-27 | 2022-09-20 | Xeris Pharmaceuticals, Inc. | Stable formulations for parenteral injection of small molecule drugs |
| US9642894B2 (en) | 2013-02-06 | 2017-05-09 | Xeris Pharmaceuticals, Inc. | Compositions for rapidly treating severe hypoglycemia |
| US11129940B2 (en) | 2014-08-06 | 2021-09-28 | Xeris Pharmaceuticals, Inc. | Syringes, kits, and methods for intracutaneous and/or subcutaneous injection of pastes |
| CN104188901A (en) * | 2014-08-12 | 2014-12-10 | 河南迪冉生物科技有限公司 | Florfenicol injection for livestock and preparation method thereof |
| US9649364B2 (en) | 2015-09-25 | 2017-05-16 | Xeris Pharmaceuticals, Inc. | Methods for producing stable therapeutic formulations in aprotic polar solvents |
| US10485850B2 (en) | 2015-09-25 | 2019-11-26 | Xeris Pharmaceuticals, Inc. | Methods for producing stable therapeutic formulations in aprotic polar solvents |
| US11590205B2 (en) | 2015-09-25 | 2023-02-28 | Xeris Pharmaceuticals, Inc. | Methods for producing stable therapeutic glucagon formulations in aprotic polar solvents |
| US11020403B2 (en) | 2017-06-02 | 2021-06-01 | Xeris Pharmaceuticals, Inc. | Precipitation resistant small molecule drug formulations |
| US11833157B2 (en) | 2017-06-02 | 2023-12-05 | Xeris Pharmaceuticals, Inc. | Precipitation resistant small molecule drug formulations |
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