CN1109748A - Rapamycin preparation used for intravenous injection - Google Patents

Rapamycin preparation used for intravenous injection Download PDF

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Publication number
CN1109748A
CN1109748A CN 94116781 CN94116781A CN1109748A CN 1109748 A CN1109748 A CN 1109748A CN 94116781 CN94116781 CN 94116781 CN 94116781 A CN94116781 A CN 94116781A CN 1109748 A CN1109748 A CN 1109748A
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Prior art keywords
rapamycin
injection
concentration
diluent
concentrated solution
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CN 94116781
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Chinese (zh)
Inventor
R·P·瓦兰尼斯
T·W·伦纳德
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Wyeth LLC
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American Home Products Corp
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Priority claimed from US08/302,190 external-priority patent/US5616588A/en
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Abstract

Disclosed herein is an aqueous, injectable rapamycin solution comprising 40 to 75 volume percent of a concentrate solution of rapamycin in propylene glycol, at concentrations of rapamycin ranging from 0.25 mg/ml to 8 mg/ml, in combination with a diluent solution comprising water, wherein the diluent comprises 60 to 25 volume percent of the combined solution and the concentration of rapamycin in the combined solution ranges from 0.1mg/ml to 4 mg/ml.

Description

Rapamycin preparation used for intravenous injection
The present invention relates to be used for intravenous rapamycin formulation and preparation method thereof.Invention disclosed herein provides a kind of intravenous injection use rapamycin formulation that does not need surfactant.One aspect of the present invention comprises the mixed liquor of the concentrated solution of rapamycin in propylene glycol and the diluent of being made up of water, and its ratio is as described below.
Rapamycin is a kind of macrolide antibiotics that is produced by streptomyces hygroscopicus, and it is found owing to have antifungal character at first.It is to fungi growth has adverse effect such as candida albicans and the little spore of Gypsum Fibrosum shape be mould etc.The United States Patent (USP) 3,929,992 that December in 1975 was authorized people such as Surendra on the 30th has been described rapamycin, its preparation method and antibiosis activity thereof.1977, Martel, R.R. wait people (Canadian Journal of Physiological Pharmacology 55:48-51,1977) to report the immunosuppressant character of rapamycin to EAE and adjuvant arthritis.1989, Calne, people such as R.Y. (Lancet 2:227,1989) and Morris, R.E. and Meiser, B.M(Medicinal Science Research, 17:609-10,1989) reported rapamycin effectiveness in the transplant rejection in suppressing the heteroplastic transplantation object respectively.There are many articles to describe the immunosuppressant and the repulsion inhibition activity of rapamycin subsequently, and begun to use the clinical research that rapamycin suppresses transplant rejection in the human body.
Rapamycin is water insoluble, and the solubilizer of using always when only being slightly soluble in the preparation parenteral administration is as propylene glycol, glycerol and PEG400.It only is slightly soluble in PEG300, insoluble or atomicly is dissolved in injection aqueous cosolvent system commonly used, as 20% ethanol/water, 10%DMA/ water, 20%Cremophor EL R/ water and 20% Spheron MD 30/70/water.Owing to these reasons, but be difficult to prepare clinical practice and can business-like rapamycin injection.December in 1981 disclosed European patent on the 16th discloses 0041795 and has described a kind of injection rapamycin compositions.In this injection, earlier rapamycin being dissolved in low boiling point organic solvent is in acetone, methanol or the ethanol, then this solution is mixed with non-ionic surface active agent, and described non-ionic surface active agent is selected from the fatty acid of polyoxyethyleneization; The aliphatic alcohol of polyoxyethyleneization; The glycerol hydroxy fatty acid of polyoxyethyleneization, for example the Oleum Ricini of polyoxyethyleneization is (as Cremophor
Figure 94116781X_IMG1
EL) and the castor oil hydrogenated of polyoxyethyleneization (as Cremophor
Figure 94116781X_IMG2
RH and Cremophor RH60).The non-ionic surface active agent that uses among the embodiment mainly is Cremophor EL.
The main immunosuppressant that is used to suppress allosome organ-graft refection in the human body at present is cyclosporin (Sandimmune
Figure 94116781X_IMG5
).Cyclosporin is a kind of annular polypeptide of being made up of 11 aminoacid.Sandimmune
Figure 94116781X_IMG6
Intravenous injection (IV) be a kind of aseptic ampoule, every milliliter contains 50mg cyclosporin, 650mg Cremophor
Figure 94116781X_IMG7
EL and pure Ph Helv.(volume content are 32.9%) (in nitrogen).Face with before, this mixture to further dilute with 0.9% sodium chloride injection or 5% dextrose injection (Physicians ' Desk Reference, 45 th ed., 1991, pp1962-64, Medical Economics Company, Inc.).At present also in the clinical research that the macrolide molecule that is called FK506 is suppressed allosome organ-graft refection in the human body.FK506 and rapamycin have certain structural similarity, separate from Streptomyces tsuskubaensis, and are described in nineteen ninety and authorize in people's such as Okuhara the United States Patent (USP) 4,894,366.People such as R.Venkataramanan (Transplantation Proceedings, 22, No.1, Suppl., lpp52-56, February nineteen ninety) report, made the intravenous injection of FK506, be the 10mg/ml solution of FK506 in polyoxyethylenated castor oil (HCO-60, a kind of surfactant) and alcohol.This intravenous formulations must dilute with saline or dextrose, and infusion 1-2 hour.
The applicant now unexpectedly finds, in two parts system of rapamycin concentrated solution and diluent water, utilizes propylene glycol to make the rapamycin solubilising, just can make pharmaceutically useful rapamycin water type injection under the situation of not using surfactant.Its special benefits is to use water as the one pack system diluent, and water because of its tissue tolerance good but preferred injection diluent.In addition, also avoided sneaking into of other diluent components.Rapamycin injection of the present invention both had been suitable for bolus injection very much, was very suitable for infusion again.
One aspect of the present invention is a kind of water base rapamycin injection, and this injection comprises the concentrated solution of rapamycin in propylene glycol and the mixed liquor that contains water diluent.Specifically, the present invention is a kind of aqueous rapamycin injection, this injection comprises the 40-75%(volume) concentration be 0.25-8mg/ml the concentrated solution of rapamycin in propylene glycol with contain the water diluent mixed liquor, wherein diluent accounts for the 60-25% of mixeding liquid volume, and the concentration of rapamycin is 0.1-4mg/ml in the mixed liquor.Preferred aqueous rapamycin injection is the injection that diluent accounts for mixeding liquid volume 40-60%.Diluent preferred water, but also can contain other solvents is as the propylene glycol of a small amount of (as 10% volume or still less).
This on the one hand preferred aqueous rapamycin injection of the present invention, the concentration that is rapamycin in the propylene glycol concentrated solution is the injection of 0.5-4mg/ml.More preferably the concentration of rapamycin is the injection of 0.6-3.3mg/ml in the propylene glycol concentrated solution.The preferred aqueous rapamycin of the present invention injection also has: rapamycin concentration is the injection of 0.25-2mg/ml in the mixed liquor; And propylene glycol accounts for the injection of mixeding liquid volume 60-40%.
The particularly preferred aqueous rapamycin injection of this one side of the present invention, comprise that 40-60% rapamycin concentration is concentrated solution and the 60-40%(volume of rapamycin in propylene glycol of 0.5-4mg/ml) mixed liquor of aqueous diluent, wherein the concentration of rapamycin is 0.25-2mg/ml in the mixed liquor.
The present invention also provides the aqueous rapamycin that supplies bolus injection as mentioned above injection, and wherein the concentration of rapamycin is preferably 0.25-2mg/ml in the injection.
A second aspect of the present invention is a kind of aqueous rapamycin injection, and described injection comprises the rapamycin in the solution that is dissolved in propylene glycol and water, and wherein water accounts for the 40-75% of liquor capacity, and the concentration of rapamycin is 0.1-4mg/ml in the solution.
This on the one hand preferred aqueous rapamycin injection of the present invention is that rapamycin concentration is the injection of 0.25-1mg/ml in the solution.Independent mutually with it and also account for the injection of liquor capacity 60-40% for water preferably.
The present invention also provides a kind of product that contains rapamycin concentrated solution and diluent, this product is a kind of combination preparation, be used for before intravenous injection, mixing and obtain the solution that rapamycin concentration is 0.1-4mg/ml, described concentrated solution comprises the solution of rapamycin in propylene glycol that concentration is 0.25-8mg/ml, described diluent comprises water, the ratio of concentrated solution and diluent be 40: 60 to 75: the 25(percent by volume).
The preparation method of rapamycin vein concentrated solution comprises: be added to rapamycin in the propylene glycol and be mixed to formation solution, this process can at room temperature be carried out.Then in a known way with the solution filtration sterilization.With the concentrated solution of the proper volume ampoule of packing into, sealing in a known way then.According to the standard fabrication operating procedure of injection, in the whole process of filtration, fill and seal operation, all keep aseptic condition.The best cold preservation of rapamycin concentrated solution product.
The preparation method of each rapamycin intravenous diluents system comprises: the sterilized water of dress proper volume in phial, and then phial built, sealed and autoclaving.The rapamycin diluent of making can at room temperature be preserved or cold preservation.
Being made into the final operating procedure of medicine composition of giving comprises: a rapamycin vein concentrated solution is injected the phial that the rapamycin intravenous diluents is housed, vibrated about one minute or until forming clear solutions.The solution for preparing should administration in the specified operating period.The operating period of the rapamycin injection for preparing is that the solution for preparing keeps clarification and colourless that time.Operating period can reach 4 hours at most, but preferred 1 hour operating period at the most.
Medicinal propylene glycol obtains from various commercial undertakings easily.
Therefore, the present invention also provides a kind of method for preparing aqueous rapamycin injection, this method comprises: make the 40-75%(volume) concentration be 0.25-8mg/ml the concentrated solution of rapamycin in propylene glycol with contain water diluent and mix, wherein diluent accounts for the 60-25% of mixeding liquid volume, is 0.1-4mg/ml thereby make the concentration of rapamycin in the injection.
The following example further specifies enforcement of the present invention.
Embodiment 1
The preparation of rapamycin injection (1mg/ml)
A.2mg/ml the preparation of the vein concentrated solution of rapamycin in propylene glycol:
Prescription (density: 1.036g/ml):
Become component
Rapamycin 100% 0.2g
Propylene glycol (American Pharmacopeia level) adds to 100ml or 103.6g
Operating procedure:
1. in container, take by weighing rapamycin through suitably calibration.
2. with propylene glycol volume is transferred to 100ml.
3. be mixed to the formation homogeneous solution.
4. with solution aseptic filtration.
5. pack in ampoule or the phial and sealing.
B.1.0mg/ml rapamycin vein diluent
Prescription (density: 1.00g/ml):
Become component
Water for injection (American Pharmacopeia level) adds to 100ml or 100g
Operating procedure:
1. 1.0ml ± the 0.01ml that in the colourless phial of each 5ml, packs into, sealing and crimping.
2. autoclaving.
C.1mg/ml rapamycin intravenous fluid (preparing)
Prescription (density: 1.035g/ml)
Become component
Rapamycin vein concentrated solution 2mg/ml 1ml
Rapamycin vein diluent 1ml
Operating procedure:
1. utilize strict aseptic technique, in the phial that 1ml rapamycin vein diluent is housed, injecting 1ml concentration is 2mg/ml rapamycin vein concentrated solution.
2. vibration is to forming settled solution.
3. administration in the operating period.
Embodiment 2
The preparation of rapamycin injection (2mg/ml)
A.4mg/ml the preparation of the vein concentrated solution of rapamycin in propylene glycol:
Prescription (density: 1.036g/ml):
Become component
Rapamycin 100% 0.4g
Propylene glycol (American Pharmacopeia level) adds to 100ml or 103.6g
Operating procedure:
1. in container, take by weighing rapamycin through suitably calibration.
2. with propylene glycol volume is transferred to 100ml.
3. be mixed to the formation homogeneous solution.
4. with solution aseptic filtration.
5. pack in ampoule or the phial and sealing.
B.2mg/ml rapamycin vein diluent
Become component
Propylene glycol (American Pharmacopeia level) 10ml
Water for injection (American Pharmacopeia level) adds to 100ml or 100g
Operating procedure:
1. propylene glycol is placed suitable containers.
2. with water for injection volume is transferred to 100ml.
3. be mixed to the formation homogeneous solution.
4. with solution aseptic filtration.
5. pack.
6. autoclaving.
C.4mg/ml rapamycin intravenous fluid (preparing)
Prescription (density: 1.035g/ml)
Become component
Rapamycin vein concentrated solution 4mg/ml 1ml
Rapamycin vein diluent 1ml
Operating procedure:
1. utilize strict aseptic technique, in the phial that 1ml rapamycin vein diluent is housed, injecting 1ml concentration is 2mg/ml. rapamycin vein concentrated solution.
2. vibration is to forming settled solution.
3. administration in the operating period.
Embodiment 3
The preparation of rapamycin injection (3mg/ml)
A.6mg/ml the preparation of the vein concentrated solution of rapamycin in propylene glycol:
Prescription (density: 1.036g/ml):
Become component
Rapamycin 100% 0.6g
Propylene glycol (American Pharmacopeia level) adds to 100ml or 103.6g
Operating procedure:
1. in container, take by weighing rapamycin through suitably calibration.
2. with propylene glycol volume is transferred to 100ml.
3. be mixed to the formation homogeneous solution.
4. with solution aseptic filtration.
5. pack in ampoule or the phial and sealing.
B.3mg/ml rapamycin vein diluent.
Prescription (density: 1.00g/ml):
Become component
Propylene glycol (American Pharmacopeia level) 10ml
Water for injection (American Pharmacopeia level) adds to 100ml or 100g
Operating procedure:
1. propylene glycol is placed suitable containers.
2. with water for injection volume is transferred to 100ml.
3. be mixed to the formation homogeneous solution.
4. with solution aseptic filtration.
5. pack.
6. autoclaving.
C.3mg/ml rapamycin intravenous fluid (preparing).
Prescription (density: 1.035g/ml):
Become component
Rapamycin vein concentrated solution 6mg/ml 1ml
Rapamycin vein diluent 1ml
Operating procedure:
1. utilize strict aseptic technique, in the phial that 1ml rapamycin vein diluent is housed, injecting 1ml concentration is 6mg/ml rapamycin vein concentrated solution.
2. vibration is to forming settled solution.
3. administration in the operating period.
Embodiment 4
The preparation of rapamycin injection (4mg/ml)
A.8mg/ml the preparation of the vein concentrated solution of rapamycin in propylene glycol:
Prescription (density: 1.036g/ml):
Become component
Rapamycin 100% 0.8g
Propylene glycol (American Pharmacopeia level) adds to 100ml or 103.6g
Operating procedure:
1. in container, take by weighing rapamycin through suitably calibration.
2. with propylene glycol volume is transferred to 100ml.
3. be mixed to the formation homogeneous solution.
4. with solution aseptic filtration.
5. pack in ampoule or the phial and sealing.
B.4mg/ml rapamycin vein diluent
Become component
Propylene glycol (American Pharmacopeia level) 10ml
Water for injection (American Pharmacopeia level) adds to 100ml or 100g
Operating procedure:
1. propylene glycol is placed suitable containers.
2. with water for injection volume is transferred to 100ml.
3. be mixed to the formation homogeneous solution.
4. with solution aseptic filtration.
5. pack.
6. autoclaving.
C.4mg/ml rapamycin intravenous fluid (preparing)
Prescription (density: 1.035g/ml):
Become component
Rapamycin vein concentrated solution 8mg/ml 1ml
Rapamycin vein diluent 1ml
Operating procedure:
1. utilize strict aseptic technique, in the phial that 1ml rapamycin vein diluent is housed, injecting 1ml concentration is 8mg/ml rapamycin vein concentrated solution.
2. vibration is to forming settled solution.
3. administration in the operating period.

Claims (18)

1, a kind of aqueous rapamycin injection, this injection can make with the method that may further comprise the steps: make 40-75% (volume) concentration be 0.25-8mg/ml the concentrated solution of rapamycin in propylene glycol with contain water diluent and mix, wherein diluent accounts for the 60-25% of mixeding liquid volume, is 0.1-4mg/ml thereby make the concentration of rapamycin in the injection.
2, the aqueous rapamycin injection of claim 1, wherein the concentrated solution of rapamycin in propylene glycol accounts for the 40-60% of injection volume.
3, claim 1 or 2 aqueous rapamycin injection, wherein the concentration of rapamycin is 0.5-4mg/ml in the propylene glycol concentrated solution.
4, a kind of aqueous rapamycin injection, this injection can make with the method that may further comprise the steps: make the 40-60%(volume) concentration is the concentrated solution of 0.5-4mg/ml rapamycin in propylene glycol and contain water diluent and mix, wherein diluent accounts for the 60-40% of mixeding liquid volume, is 0.25-2mg/ml thereby make the concentration of rapamycin in the injection.
5, each aqueous rapamycin injection among the claim 1-4, wherein the concentrated solution of rapamycin in propylene glycol accounts for the 40-50% of injection volume.
6, each aqueous rapamycin injection among the claim 1-5, wherein the concentration of rapamycin is 0.6-3.3mg/ml in the propylene glycol concentrated solution.
7, each aqueous rapamycin injection among the claim 1-6, wherein the concentration of rapamycin is 0.5-1.5mg/ml in the injection.
8, the aqueous rapamycin injection for bolus injection of claim 1, wherein the concentration of rapamycin is 0.25-2mg/ml in the injection.
9, a kind of aqueous rapamycin injection, described injection comprises the rapamycin in the solution that is dissolved in propylene glycol and water, and wherein water accounts for the 40-75% of liquor capacity, and the concentration of rapamycin is 0.1-4mg/ml in the solution.
10, a kind of product that contains rapamycin concentrated solution and diluent, this product is a kind of combination preparation, be used for before intravenous injection, mixing and obtain the solution that rapamycin concentration is 0.1-4mg/ml, described concentrated solution comprises the solution of rapamycin in propylene glycol that concentration is 0.25-8mg/ml, described diluent comprises water, the ratio of concentrated solution and diluent be 40: 60 to 75: the 25(percent by volume).
11, the product of claim 10, wherein the ratio of concentrated solution and diluent be 60: 40 to 40: the 60(percent by volume).
12, claim 10 or 11 product, wherein the concentration of rapamycin is 0.5-4mg/ml in the propylene glycol concentrated solution.
13, the product for bolus injection of claim 10, wherein the mixed concentration of rapamycin concentrated solution and diluent is 0.25-2mg/ml.
14, a kind of product that contains rapamycin concentrated solution and diluent, this product is a kind of combination preparation, be used for before intravenous injection, mixing and obtain the solution that rapamycin concentration is 0.1-4mg/ml, described concentrated solution comprises the solution of rapamycin in propylene glycol that concentration is 0.5-4mg/ml, described diluent comprises water, the ratio of concentrated solution and diluent be 40: 60 to 75: the 25(percent by volume).
15, a kind of method for preparing aqueous rapamycin injection, this method comprises: make the 40-75%(volume) concentration be 0.25-8mg/ml the concentrated solution of rapamycin in propylene glycol with contain water diluent and mix, wherein diluent accounts for the 60-25% of mixeding liquid volume, is 0.1-4mg/ml thereby make the concentration of rapamycin in the injection.
16, the method for claim 15, wherein the concentrated solution of rapamycin in propylene glycol accounts for the 40-60% of injection volume.
17, claim 15 or 16 method, wherein the concentration of rapamycin is 0.5-4mg/ml in the propylene glycol concentrated solution.
18, a kind of method for preparing aqueous rapamycin injection, this method comprises: make the 40-60%(volume) concentration be 0.5-4mg/ml the concentrated solution of rapamycin in propylene glycol with contain water diluent and mix, wherein diluent accounts for the 60-40% of mixeding liquid volume, is 0.25-2mg/ml thereby make the concentration of rapamycin in the injection.
CN 94116781 1993-09-30 1994-09-29 Rapamycin preparation used for intravenous injection Pending CN1109748A (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US12952693A 1993-09-30 1993-09-30
US129,526 1993-09-30
US08/302,190 US5616588A (en) 1993-09-30 1994-09-12 Rapamycin formulation for IV injection
US302,190 1994-09-12

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CN1109748A true CN1109748A (en) 1995-10-11

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BR (1) BR9403945A (en)
CA (1) CA2133180A1 (en)
IL (1) IL111008A (en)
TW (1) TW438586B (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2008022557A1 (en) * 2006-08-17 2008-02-28 Jianmin Zhang Liquid composition of sirolimus
CN100402031C (en) * 2002-07-30 2008-07-16 惠氏公司 Parenteral formulations containing rapamycin hydroxyester
CN109431997A (en) * 2018-12-20 2019-03-08 武汉科福新药有限责任公司 A kind of rapamycin locally injecting preparation and preparation method thereof

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2001253824A (en) * 2000-03-14 2001-09-18 Mitsukazu Matsumoto Formulated agent for local injection
US20080096972A1 (en) * 2004-07-30 2008-04-24 Thitiwan Buranachokpaisan Compound formulations of 2-amino-1, 3-propanediol compounds

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN100402031C (en) * 2002-07-30 2008-07-16 惠氏公司 Parenteral formulations containing rapamycin hydroxyester
WO2008022557A1 (en) * 2006-08-17 2008-02-28 Jianmin Zhang Liquid composition of sirolimus
CN109431997A (en) * 2018-12-20 2019-03-08 武汉科福新药有限责任公司 A kind of rapamycin locally injecting preparation and preparation method thereof

Also Published As

Publication number Publication date
IL111008A (en) 1999-10-28
JP3584064B2 (en) 2004-11-04
JPH07196507A (en) 1995-08-01
BR9403945A (en) 1995-06-13
CA2133180A1 (en) 1995-03-31
IL111008A0 (en) 1994-11-28
TW438586B (en) 2001-06-07

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