18507-89-6 Usage
Uses
Used in Veterinary Medicine:
Decoquinate is used as a monoxycarbolic acid antibiotic for treating quinoline coccidia in animals.
Used in Poultry Industry:
Decoquinate is used as a feed additive for poultry, specifically at a dosage of 27.2g in 1 ton of feed, to prevent broiler coccidiosis. Its wide dosage range of safety and rapid metabolism allow for a withdrawal period of 3 days, with residual drug concentration in each tissue being less than 1ppm.
Used in Antiviral Applications:
Decoquinate is also utilized as an antiviral agent, although the specific application details are not provided in the materials.
Highly Effective Anti-coccidiosis for Livestock and Poultry
Decoquinate is a new type highly-efficienct quinolones anti-coccidiosis for livestock and poultry, commonly known as quinoxetine, decanoquinolate, paclitaxel, to quinolate, benzoquinone. The active compound is white or slightly yellow crystalline powder, rarely soluble in chloroform or ether, insoluble in water or ethanol. It has a unique anti-coccidial activity stronger than Maduramicin, nicarbazine + Ethanamidobenzylate, methyl salicin. Studies have shown that decanoquinolines are effective in combating the resistance from coccidium and are clinically used to control the most harmful poultry coccidiosis caused by E.tenella, E.maxima, E.acerVulina, E.necatrix, E.brunetti, E.mivati). it can also effect in the precaution of neosporosis in livestocks of cattle and sheep. It can improve the weight growth rate and milk yield of young goat.
Decoquinate plays a role in the asexual reproduction of coccidia, and after entering the sporozoite cell, it prevents its development by interfering with DNA synthesis. It begins to function in the early stages of life history of coccidia, effectively prevents the coccidia caused by intestinal damage. Addition of decoquinate in the fodder does not affect the digestion of the fodder and the absorption of nutrients.
This product has no incompatibility except that it can not be used in the feed containing bentonite.
Quinoline anticoccidial drugs are easy to be resisted. It is recommended continuous use of up to no more than 4 weeks be applied only in the peak period of coccidia,.
Since the 1970s, decanoquinolines have been widely used in the control of coccidiosis in poultry in many countries, but have not been used in China.
In 2006, the Alpharma (U.S.) first introduced quinoline into China market, which had aroused wide attention. Its first use in China had presented no drug resistance, its use as ideal alternative, killing effect on coccidia, promoting effect on growth, improvement effect on the color, excellent anticoccidial effect and growth performance in the early life; it starts to play a role in the early stages of life history of coccidia with the longest effect duration and a wide anticoccidial spectrum. It has extermination effect on the most harmful 6 avian coccidia with an excellent stability. It can keep stable quality for 4 years at proper temperature and humidity.
At present, Healthy (Hangzhou) Husbandry Sci-tech Co., Ltd, Shandong Sinder Technology Co., Ltd produce and market decoquinate APIs.
Chemical and Physical Properties
Light yellow crystalline powder;
Melting point at 86-87 DEG C;
Slightly soluble in chloroform, ether, almost insoluble in water;
Odorless.
Toxicological Information
Decoquinate is well tolerated with low toxicity and dosage 80 times of the recommended is still safe.
Poultry: addition of 800ppm in fodder (26 times the normal dosage) with continuous feeding for 127 days caused no poisoning;
Pigs: 800ppm continuous feeding for 10 days caused no poisoning.
Pharmacokinetics
Decoquinate is fast absorpted. It reaches the effective concentration within 1 hour and its peak level 3 days after.
On the 5th days and 7th days after the administration of unlabeled qecoquinate on the cattle and sheep, a single dose of this product labeled with 14C was intravenously injected into the cattle, sheep and the plasma radiation reaches the peak 1.5 hours after.
Decoquinate is partially metabolized in the rat body, resulting in three kinds of metabolites, but the structure cannot be determined.
Only two of its metabolites are identified in ruminants, and the proportion is lower than that of rats. Its main excretion in ruminants is manure, followed by urine. In sheep, urine excreted 36% of the total dose and 35% is discharged within 24 hours; qecoquinate and its metabolites in urinary is completely discharged in 3 days.
Drug Combination
In order to improve the anti-coccidia effect and reduce drug resistance, you can take a combination of drugs. In the early stages of coccidiosis (coccidiosis asexual breeding period) using decanoquinate + diclazuril, calcitonizumole or deccox + maduramicin, deccox + chloropyridine and other combination therapy to perform a synergistic effect of drugs to enhance the killing effect, while the use of each drug can reduce 1/2. In the fully outbreak period of coccidiosis, the use of deccox +sodium sulfaquinoxaline, deccox + SPZ and other combination therapy can inhibit and kill coccidium in asexual breeding and sexual reproduction.
Synthesis Method
3,4-dihydroxy nitrobenzene reacts with bromodecane in DMF medium to produce 3-hydroxy-4-decyloxy nitrobenzene. And the product is then ethoxylated and reduced to produce 3-ethoxy-4-decyloxyaniline. Then, 3-ethoxy-4-decyloxyaniline is condensed with diethyl ethoxymethylenemalonate to produce 3-ethoxy-4-decyloxyanilide methylidene malonate ester, which is finally transformed into finished product through heat condensation with dowtherm A.
Veterinary Drugs and Treatments
Decoquinate is labeled for use in cattle for the prevention of coccidiosis
in either ruminating or non-ruminating calves, cattle or young
goats caused by the species E. christenseni or E. ninakohlyakimoviae.
It is used for prevention of coccidiosis in broilers caused by E. tenella,
E. necatrix, E. acervulina, E. mivati, E. maxima or E. burnetti.
It may be useful in dogs as prophylactic treatment for coccidiosis
and hepatozoonosis relapse.
Check Digit Verification of cas no
The CAS Registry Mumber 18507-89-6 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,8,5,0 and 7 respectively; the second part has 2 digits, 8 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 18507-89:
(7*1)+(6*8)+(5*5)+(4*0)+(3*7)+(2*8)+(1*9)=126
126 % 10 = 6
So 18507-89-6 is a valid CAS Registry Number.
InChI:InChI=1/C24H35NO5/c1-4-7-8-9-10-11-12-13-14-30-21-15-18-20(16-22(21)28-5-2)25-17-19(23(18)26)24(27)29-6-3/h15-17H,4-14H2,1-3H3,(H,25,26)
18507-89-6Relevant articles and documents
Synthetic method of decoquinate
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Paragraph 0018; 0026; 0032, (2018/03/01)
The invention discloses a synthetic method of decoquinate, and belongs to the technical field of pharmaceutical engineering. The synthetic method takes o-hydroxyphenyl ethyl ether as a raw material to prepare decoquinate via the processes of coupling, reduction, condensation, etherification, cyclization and the like. The process of reduction in the method adopts environment-friendly hydrazine hydrate as a reducer to reduce an azo-compound and introduce an amino group, so that the synthetic method is good in selectivity, and environmentally friendly, and beneficial for reducing environmental pollution problems; BTC is adopted as a cyclization reagent in the process of cyclization, so that the condition is mild, the requirement on equipment is lowered, and the cost is reduced.
Preparation method of decoquinate
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Paragraph 0032, (2017/01/19)
The invention discloses a preparation method of decoquinate. Industrialized 2-hydroxyphenylacetic acid phenetole serves as starting materials, and a product with better quality is obtained through diazo coupling, sodium dithionite reduction, condensation, etherificationa and superstrong solid acid SO4/Fe2O3 and sodium bisulfate cyclization. Part intermediate of a synthetic route of the decoquinate does not need to be purified, used solvent is single, aftertreatment of the intermediate and use of organic solvent are reduced, the cost is reduced, the whole process route is short, extremely high temperature or highly corrosive liquid acid is not needed, requirement to equipment is low, operation is easy and convenient, the production cycle is short, produced three wastes are fewer, the production yield is high, the quality is good, and the preparation method of the decoquinate is suitable for industrial production.
Convenient and efficient preparation of ethyl 6-n-decyloxy-7-ethoxy-4- hydroxyquinoline-3-carboxylate
Xu, Maoyou,Zhang, Jin,Wu, Xue,Sun, Juanjuan,Shi, Zhiqiang
experimental part, p. 992 - 997 (2010/05/18)
Ethyl 6-N-decyloxy-7-ethoxy-4-hydroxyquinoline-3-carboxylate has been synthesized from pyrocatechol in six steps and in 39.3% overall yield.
Efficient and practical synthesis of dissymmetrical ethers of 4-nitrocatechol
Subashini, Murugan,Balasubramanian, Kalpattu K.,Bhagavathy, Shanmugasundaram
, p. 3088 - 3106 (2008/12/22)
An efficient and practical synthesis of dissymmetrical ethers of 4-nitrocatechol from 5-nitrosalicyladehyde and 2-hydroxy-5-nitroacetophenone via Baeyer-Villiger oxidation is described. These dissymmetrical ethers are useful in the synthesis of various coccidiostats and other important pharmaceutical intermediates. Copyright Taylor & Francis Group, LLC.
Process for formulating a synthetic drug for use in animal feed, and resulting formulation
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, (2008/06/13)
A method of formulating a synthetic drug for use in animal feed, for the purpose of reducing carry-over of the synthetic drug to subsequent lots of animal feed in the feed mill.
