CN109718198A - A kind of injection and preparation method thereof for treating prostate cancer - Google Patents
A kind of injection and preparation method thereof for treating prostate cancer Download PDFInfo
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- CN109718198A CN109718198A CN201711052435.0A CN201711052435A CN109718198A CN 109718198 A CN109718198 A CN 109718198A CN 201711052435 A CN201711052435 A CN 201711052435A CN 109718198 A CN109718198 A CN 109718198A
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Abstract
A kind of injection and preparation method thereof for treating prostate cancer.The invention discloses the injections of a kind of compound or its pharmaceutically acceptable salt or prodrug shown in formula I, the injection includes active constituent and additives, the active constituent is such as the compound of Formulas I or its pharmaceutically acceptable salt or prodrug, the injection is single dose injection agent, active component content 1-100mg.Injection of the invention is with good stability, safety, bioavilability and drug effect, is a kind of to treat the ideal injection-type preparation of carcinoma of prostate.
Description
Technical field
The present invention relates to the CYP17 inhibitor class field of pharmaceutical preparations for the treatment of prostate cancer.Relate more specifically to 17- (3-
Pyridyl group) androstane -5,16- diene -3 β -ol or its pharmaceutically acceptable salt or the injection of prodrug and preparation method thereof.
Background technique
Abiraterone (Abiraterone；No. CAS: 154229-19-3；Molecular formula: C24H31NO；Molecular weight: 349.5g/
It mol is) CYP17 inhibitor, structural formula is shown in formula I, is clinically primarily adapted for use in and previously connects with prednisone combination for treatment
By containing more wash Paclitaxel Chemotherapy transfer go to release refractory prostate cancer patient.
Abiraterone acetate, the entitled Abiraterone acetate of English；Entitled (3 the β) -17- (3- pyridyl group)-of chemistry
Androstane -5,16- diene -3- acetic acid esters；No. CAS: 154229-18-2), chemical structure is as shown in Formula II.Abiraterone acetate
For lipophilic compound, octanol-water partition coefficient is 5.12 (log P), especially not soluble in water.Abiraterone acetate is Ah's bit
The prodrug of dragon, is quickly converted to abiraterone in vivo.The product of Abiraterone acetateTablet is by Johnson & Johnson, U.S. public affairs
Department holds, and lists ratify in acquisition U.S. FDA on April 28th, 2011 for the first time.Tablet (250mg) is in the U.S. batch
It is mutatis mutandis to receive to wash Paclitaxel Chemotherapy patients with prostate cancer containing in prednisone drug combination treatment the past more.Tablet pushes away
It recommends dosage and takes the absorption of increase drug together with food for 1000mg (4 × 250mg tablet) once a day, such as drug, from
And it is likely to result in increasing the exposure of drug and the exposure of Level Change drug；Therefore this drug should be administered at empty stomach, it at least should be in meal
Previous hour or at least after the meal two hours take the drug.So as to learn, at present Abiraterone acetate there are the problem of
For oral tablet taking dose it is big, bioavilability is low and is influenced that big, adverse reaction is more by food.
And how to solve Abiraterone acetate oral dose is big, oral administration bioavilability is low, it is individual between and it is a in vivo
The big problem of difference has become this field urgent problem to be solved.Therefore there is an urgent need in the art to be compound of formula I or its salt
Or precursor provides the injection that a kind of stability is good, bioavilability is high.
Summary of the invention
The present invention is intended to provide a kind of stability is good, highly-safe, bioavilability is high, the treatment prostate cancer of good drug efficacy
Injection.
The present invention provides a kind of injection for treating prostate cancer,
The injection includes active constituent and additives, the active constituent be as the compound of Formulas I or its pharmaceutically
Acceptable salt or prodrug, which is characterized in that the injection is single dose injection agent, active component content 1-100mg；
Preferably, active component content 10-50mg.
In the embodiment of injection of the invention, the pharmaceutically acceptable prodrug is as shown in Formula II
Injection of the invention may also include the additives of this field routine.Preferably, the additives include following molten
One or more of agent: dehydrated alcohol, glycerol, propylene glycol, soybean oil, castor oil, polyethylene glycol Ergol, oleic acid second
Ester, glyceryl triacetate, pungent/capric acid glyceryl ester, glyceryl triacetate, dimethyl acetamide；Preferably, the solvent includes
Dehydrated alcohol and/or polyethylene glycol.
In the embodiment of injection of the invention, polyethylene glycol is selected from Liquid Macrogol, polyethylene glycol 400 and poly- second
The one or more of glycol 600.
In the embodiment of injection of the invention, the additives further include the solubilizer of this field routine；Preferably, institute
Stating solubilizer is Emulsifier EL-60 or 15-hydroxy polyethylene glycol stearate.
In the embodiment of injection of the invention, the injection includes that the active component content is 0.2-20mg/ml,
Dehydrated alcohol content is 20-90% (V/V), and polyethyleneglycol content is 5-50% (V/V).
In the embodiment of injection of the invention, the injection includes the active component content 0.2-20mg/ml, nothing
Water-ethanol content is 20-90% (V/V), and polyethyleneglycol content is 5-50% (V/V), and Emulsifier EL-60 or 15- hydroxyl are hard
Resin acid macrogol ester is 5-45% (V/V).
In the embodiment of injection of the invention, the injection includes the active component content 4-10mg/ml, anhydrous
Ethanol content is 35-60% (V/V), and polyethyleneglycol content is 25-40% (V/V), Emulsifier EL-60 or 15- hydroxy stearate
Acid polyethylene glycol ester is 15-30% (V/V).
The present invention can be prepared with conventional method in that art.
The present invention also provides a kind of preparation methods of injection, which comprises the following steps:
(1) compound of formula I or its salt or its prodrug for taking appropriate solvent dissolution recipe quantity, obtain solution A；
(2) it takes the solubilizer of recipe quantity to be added in solution A, obtains solution B；
(3) solvent is added into solution B to full dose, stirs evenly, obtains solution C；
(4) take solution C, conventional method filtering, filling into cillin bottle, sterilizing, packaging to get.
In one embodiment of injection of the invention, it is a kind of include as the compound of Formula II or its can pharmaceutically connect
The injection for the salt received,
The injection includes following component:
Formula II compound 4-10g
Dehydrated alcohol 400-450ml
PEG400350-400ml
Solubilizer 200-250ml
Preferably, the solubilizer is polyethylene glycol ethylene castor oil or 15-hydroxy polyethylene glycol stearate；
(1) the Formula II compound for taking above-mentioned appropriate dehydrated alcohol dissolution recipe quantity, obtains solution A；
(2) it takes the solubilizer of recipe quantity to be added in solution A, obtains solution B；
(3) dehydrated alcohol is added into solution B to the full dose for configuring liquid, stirs evenly, obtains solution C；
(4) solution C is taken, conventional method filtering, filling into cillin bottle, every bottle of filling 5ml, every bottle contains acetic acid Ah bit
Imperial 20-50mg, sterilizing, packaging to get.
Raw material, auxiliary material and reagent of the invention can be commercially available.
Beneficial effects of the present invention: abiraterone injection of the invention is with good stability, safety, biology benefit
Expenditure and drug effect, 6 months assay test exhibit stabilizations are good, and rabbit irritation test proves its good security,
Its mouse pharmacodynamic test also gives good therapeutic effect.Therefore, the present invention provides a kind of ideal treatment prostate cancers
Injection-type preparation.
Detailed description of the invention
Fig. 1 is the dissolution curve comparison diagram of the embodiment of the present invention and commercially available capsule.
Fig. 2 is that the safety testing of embodiment 1 visually observes photo.
Fig. 3 is the pathological section result of the safety testing of embodiment 1.
Specific embodiment
Below with reference to embodiment, the present invention will be further elaborated, following description merely to explain the present invention,
Any restriction is not carried out to its content.
Embodiment 1
Preparation method: (4mg/ml)
(1) Abiraterone acetate for taking appropriate dehydrated alcohol dissolution recipe quantity, obtains solution A；
(2) it takes the polyethylene glycol ethylene castor oil of recipe quantity to be added in solution A, obtains solution B；
(3) dehydrated alcohol is added into solution B to the full dose for configuring liquid, stirs evenly, obtains solution C；
(4) solution C is taken, conventional method filtering, filling into cillin bottle, every bottle of filling 5ml, filling 200 bottles altogether, every bottle contains
There is Abiraterone acetate 20mg, sterilize, packs to get Abiraterone acetate injection of the invention.
Embodiment 2
Preparation method: (4mg/ml)
(1) Abiraterone acetate for taking appropriate dehydrated alcohol dissolution recipe quantity, obtains solution A；
(2) it takes the polyethylene glycol ethylene castor oil of recipe quantity to be added in solution A, obtains solution B；
(3) dehydrated alcohol is added into solution B to the full dose for configuring liquid, stirs evenly, obtains solution C；
(4) solution C is taken, conventional method filtering, filling into cillin bottle, every bottle of filling 5ml, filling 200 bottles altogether, every bottle contains
There is Abiraterone acetate 20mg, sterilize, packs to get Abiraterone acetate injection of the invention.
Embodiment 3
Preparation method: (4mg/ml)
(1) Abiraterone acetate for taking appropriate dehydrated alcohol dissolution recipe quantity, obtains solution A；
(2) it takes the 15-hydroxy polyethylene glycol stearate of recipe quantity to be added in solution A, obtains solution B；
(3) dehydrated alcohol is added into solution B to the full dose for configuring liquid, stirs evenly, obtains solution C；
(4) solution C is taken, conventional method filtering, filling into cillin bottle, every bottle of filling 5ml, filling 200 bottles altogether, every bottle contains
There is Abiraterone acetate 20mg, sterilize, packs to get Abiraterone acetate injection of the invention.
Embodiment 4
Preparation method: (4mg/ml)
(1) Abiraterone acetate for taking appropriate dehydrated alcohol dissolution recipe quantity, obtains solution A；
(2) it takes the 15-hydroxy polyethylene glycol stearate of recipe quantity to be added in solution A, obtains solution B；
(3) dehydrated alcohol is added into solution B to the full dose for configuring liquid, stirs evenly, obtains solution C；
(4) solution C is taken, conventional method filtering, filling into cillin bottle, every bottle of filling 5ml, filling 200 bottles altogether, every bottle contains
There is Abiraterone acetate 20mg, sterilize, packs to get Abiraterone acetate injection of the invention.
Embodiment 5
Preparation method: (0.2mg/ml)
(1) Abiraterone acetate for taking appropriate dehydrated alcohol dissolution recipe quantity, obtains solution A；
(2) it takes the polyethylene glycol ethylene castor oil of recipe quantity to be added in solution A, obtains solution B；
(3) dehydrated alcohol is added into solution B to the full dose for configuring liquid, stirs evenly, obtains solution C；
(4) solution C is taken, conventional method filtering, filling into cillin bottle, every bottle of filling 5ml, filling 200 bottles altogether, every bottle contains
There is Abiraterone acetate 1mg, sterilize, packs to get Abiraterone acetate injection of the invention.
Embodiment 6
Preparation method: (10mg/ml)
(1) Abiraterone acetate for taking appropriate dehydrated alcohol dissolution recipe quantity, obtains solution A；
(2) it takes the polyethylene glycol ethylene castor oil of recipe quantity to be added in solution A, obtains solution B；
(3) dehydrated alcohol is added into solution B to the full dose for configuring liquid, stirs evenly, obtains solution C；
(4) solution C is taken, conventional method filtering, filling into cillin bottle, every bottle of filling 5ml, filling 200 bottles altogether, every bottle contains
There is Abiraterone acetate 50mg, sterilize, packs to get Abiraterone acetate injection of the invention.
Embodiment 7
Preparation method: (20mg/ml)
(1) Abiraterone acetate for taking appropriate dehydrated alcohol dissolution recipe quantity, obtains solution A；
(2) it takes the polyethylene glycol ethylene castor oil of recipe quantity to be added in solution A, obtains solution B；
(3) dehydrated alcohol is added into solution B to the full dose for configuring liquid, stirs evenly, obtains solution C；
(4) solution C is taken, conventional method filtering, filling into cillin bottle, every bottle of filling 5ml, filling 200 bottles altogether, every bottle contains
There is Abiraterone acetate 100mg, sterilize, packs to get Abiraterone acetate injection of the invention.
Embodiment 8
Preparation method: (6mg/ml)
(1) Abiraterone acetate for taking appropriate dehydrated alcohol dissolution recipe quantity, obtains solution A；
(2) it takes the 15-hydroxy polyethylene glycol stearate of recipe quantity to be added in solution A, obtains solution B；
(3) dehydrated alcohol is added into solution B to the full dose for configuring liquid, stirs evenly, obtains solution C；
(4) solution C is taken, conventional method filtering, filling into cillin bottle, every bottle of filling 5ml, filling 200 bottles altogether, every bottle contains
There is Abiraterone acetate 30mg, sterilize, packs to get Abiraterone acetate injection of the invention.
Effect example
(1) stability test
Sample in above-described embodiment and comparative example is placed 6 under the conditions of 40 ± 2 DEG C, relative humidity (75 ± 5) %
Moon sampling carries out study on the stability to the Abiraterone acetate in injection, is to investigate to refer to projects such as appearance character, contents
Mark, Dichlorodiphenyl Acetate abiraterone injection carry out acceleration in 6 months and investigate.
Percentage composition measurement is carried out using Abiraterone acetate of the following high performance liquid chromatography to embodiment 1-8.Institute
Stating high performance liquid chromatography uses C18 column (chromatographic column for kromasil 100C18 column, 4.6 × 150mm, 5um), with 75% first
Alcohol is mobile phase, and wherein Detection wavelength is 210nm, and column temperature is 30 DEG C, flow velocity 1ml/min.Embodiment changes of contents result ginseng
It is shown in Table 1.
Table 1
| Embodiment | Time (moon) | Appearance character | Content (%) | Total miscellaneous/mono- miscellaneous (%) |
| Embodiment 1 | 0 | Meet regulation | 100.2% | 0 |
| Embodiment 1 | 6 | Meet regulation | 100.3% | 0 |
| Embodiment 2 | 0 | Meet regulation | 99.6% | 0.4 |
| Embodiment 2 | 6 | Meet regulation | 98.6% | 1.4 |
| Embodiment 3 | 0 | Meet regulation | 99.9% | 0.1 |
| Embodiment 3 | 6 | Meet regulation | 99.3% | 0.7 |
| Embodiment 4 | 0 | Meet regulation | 100.1% | 0 |
| Embodiment 4 | 6 | Meet regulation | 99.8% | 0.2 |
| Embodiment 5 | 0 | Meet regulation | 100.1% | 0 |
| Embodiment 5 | 6 | Meet regulation | 100.3% | 0 |
| Embodiment 6 | 0 | Meet regulation | 99.2% | 0.8 |
| Embodiment 6 | 6 | Meet regulation | 97.8% | 2.2 |
| Embodiment 7 | 0 | Meet regulation | 98.4% | 1.6 |
| Embodiment 7 | 6 | Meet regulation | 96.7% | 3.3 |
| Embodiment 8 | 0 | Meet regulation | 99.6% | 0.4 |
| Embodiment 8 | 6 | Meet regulation | 99.0% | 1.0 |
Interpretation of result: can be seen that injection of the invention by the result of table 1 and have good stability, and embodiment 1 is implemented
Example 4, embodiment 5, embodiment 8 are more excellent.
(2) safety testing
Administration route: intramuscular injection.
Medication: medical fluid is extracted with disposable syringe, is injected in rabbit quadriceps muscle of thigh.On the right side of same rabbit
Vehicle controls are injected, tested material is injected in left side.
Dosage: negative control: Vehicle controls 1ml/ times；Given the test agent: embodiment 1-8 sample, 1ml/ times；Administration frequency
Rate and time limit: disposable injection
Indexs measure
Take within 48 hours rabbit two sides quadriceps muscle of thigh administration injection local after the last administration, visual observations intramuscular injection site thorn
Passion condition (if visually observing the irritating reaction of muscle, should leave a rabbit, observe 14~21 days depending on recovery extent), according to
Table 1 scores.Muscle send pathology to make cut sections for microscopic examination.
Pathology microscopy: being fixed with 10% formaldehyde, be dehydrated, embedded, is sliced after administration part is longitudinal sectional, H.E dyeing, last mirror
Inspection.
Grade scale is reacted in 2 muscular irritation of table
Experimental result:
Embodiment 1 visually observes photo as shown in Fig. 2, visually observing scoring as shown in table 3.Note: side is administered in 1-L；1-
R: solvent side.The visual results scoring of embodiment 1-8 is shown in Table 3.
3 visual results grade form of table
The pathological section result of embodiment 1 is as shown in Figure 3.Side is administered in 1-L；1-R: solvent side.
Each muscle is visually observed without apparent congested, red and swollen, necrosis phenomena, pathological section microscopy muscle fibre is complete, arrangement
Neatly, no congested, dissolution and inflammatory cell aggregation.
Conclusion: rabbit quadriceps muscle of thigh injects tested material solution 0.2-20mg/mL, has no apparent muscular irritation reaction.
(3) pharmacodynamic test
Experimental method: 10^ is injected intraperitoneally in 6-8 weeks NSG male mice7Prostate gland cancer cell.100 cubes are grown to tumour
Millimeter (long x wide x high x0.52), Example 1, embodiment 5, embodiment 6 and embodiment 7 sample mouse peritoneal is injected
Administration；The dosage of the Abiraterone acetate of embodiment 1, embodiment 5, embodiment 6 and embodiment 7 be 1mg, 20mg, 50mg,
100mg, the Abiraterone acetate dosage that mouse is equivalent to after conversion is respectively 0.13mg/kg, 2.6mg/kg, 6.5mg/
Kg, 13mg/kg, take orally (stomach-filling) administration group be 130mg/kg (Tablet, once a day 1000mg (4 × 250mg piece
Agent)), successive administration 20 days.Mouse is put to death after treatment 20 days.The survival rate of each group mouse is counted such as Fig. 1 and table 4.
Table 4
Interpretation of result: it can be seen that according to the result of Fig. 1 and table 4 when injection agent dose is 1-100mg, drug effect is close
Even better than oral administration group as a result, especially when injection dosage be 10-100mg when, drug effect is substantially better than oral administration group.
Unless this specification is defined otherwise, the meaning of science and technology vocabulary used herein and those skilled in the art institute
Understand identical as usual meaning.In addition, singular noun used in this specification covers in the case of getting along well context conflict
The complex number type of the noun；And also cover the singular type of the noun when used plural noun.
The foregoing is merely illustrative of the preferred embodiments of the present invention, the substantial technological content model being not intended to limit the invention
It encloses, substantial technological content of the invention is broadly defined in the scope of the claims of application, any technology that other people complete
Entity or method also or a kind of equivalent change, will if identical with defined in the scope of the claims of application
It is considered as being covered by among the scope of the claims.
Claims (10)
1. a kind of injection for treating prostate cancer,
The injection includes active constituent and additives, the active constituent be as the compound of Formulas I or its can pharmaceutically connect
Salt, the prodrug received, which is characterized in that the injection is single dose injection agent, active component content 1-100mg；It is preferred that
Ground, active component content 10-50mg.
2. injection according to claim 1, wherein the pharmaceutically acceptable prodrug is as shown in Formula II
3. injection according to claim 1, wherein the additives include one or more of following solvent: nothing
Water-ethanol, glycerol, propylene glycol, soybean oil, castor oil, polyethylene glycol Ergol, ethyl oleate, glyceryl triacetate, it is pungent/
Capric acid glyceryl ester, glyceryl triacetate, dimethyl acetamide；Preferably, the solvent includes dehydrated alcohol and/or poly- second two
Alcohol.
4. injection according to claim 3, wherein polyethylene glycol be selected from Liquid Macrogol, polyethylene glycol 400 and
The one or more of Macrogol 600.
5. injection according to claim 3, wherein the additives further include solubilizer；Preferably, the solubilizer
For Emulsifier EL-60 or 15-hydroxy polyethylene glycol stearate.
6. injection according to claim 4, wherein the injection includes that the active component content is 0.2-
20mg/ml, dehydrated alcohol content are 20-90% (V/V), and polyethyleneglycol content is 5-50% (V/V).
7. injection according to claim 5, wherein the injection includes the active component content 0.2-20mg/
Ml, dehydrated alcohol content are 20-90% (V/V), and polyethyleneglycol content is 5-50% (V/V), Emulsifier EL-60 or 15- hydroxyl
Base stearic acid macrogol ester is 5-45% (V/V).
8. injection according to claim 5, which is characterized in that the injection includes the active component content 4-
10mg/ml, dehydrated alcohol content are 35-60% (V/V), and polyethyleneglycol content is 25-40% (V/V), Emulsifier EL-60
Or 15-hydroxy polyethylene glycol stearate is 15-30% (V/V).
9. according to the preparation method of the described in any item injections of claim 5-8, which comprises the following steps:
(1) compound of formula I or its prodrug or salt for taking appropriate solvent dissolution recipe quantity, obtain solution A；
(2) it takes the solubilizer of recipe quantity to be added in solution A, obtains solution B；
(3) solvent is added into solution B to full dose, stirs evenly, obtains solution C；
(4) take solution C, conventional method filtering, filling into cillin bottle, sterilizing, packaging to get.
10. a kind of includes the injection such as the compound of Formula II or its pharmaceutically acceptable salt,
The injection includes following component:
Formula II compound 4-10g
Dehydrated alcohol 400-450ml
PEG400350-400ml
Solubilizer 200-250ml
Preferably, the solubilizer is polyethylene glycol ethylene castor oil or 15-hydroxy polyethylene glycol stearate；
(1) Abiraterone acetate for taking above-mentioned appropriate dehydrated alcohol dissolution recipe quantity, obtains solution A；
(2) it takes the solubilizer of recipe quantity to be added in solution A, obtains solution B；
(3) dehydrated alcohol is added into solution B to the full dose for configuring liquid, stirs evenly, obtains solution C；
(4) solution C is taken, conventional method filtering, filling into cillin bottle, every bottle of filling 5ml, every bottle contains Abiraterone acetate
20-50mg, sterilizing, packaging to get.
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| CN201711052435.0A CN109718198A (en) | 2017-10-30 | 2017-10-30 | A kind of injection and preparation method thereof for treating prostate cancer |
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Cited By (1)
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| CN115581664A (en) * | 2022-10-19 | 2023-01-10 | 山东诺明康药物研究院有限公司 | Abiraterone acetate nanocrystalline injection and preparation method thereof |
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| CN115581664A (en) * | 2022-10-19 | 2023-01-10 | 山东诺明康药物研究院有限公司 | Abiraterone acetate nanocrystalline injection and preparation method thereof |
| CN115581664B (en) * | 2022-10-19 | 2024-07-30 | 山东诺明康药物研究院有限公司 | Abat Long Nami crystal acetate injection and preparation method thereof |
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Application publication date: 20190507 |