Milbemycin A3 oxime
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| Category | Bioactive by-products |
| Catalog number | BBF-04155 |
| CAS | 114177-14-9 |
| Molecular Weight | 541.67 |
| Molecular Formula | C31H43NO7 |
| Purity | >95% |
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Description
Milbemycin A3 oxime is a semi-synthetic macrocyclic lactone prepared by the oxidation and oximation of a mixture of milbemycin A3. Milbemycin A3 oxime is the minor component of the anti-parasitic product milbemycin oxime.
Specification
| Synonyms | 5-Oxomilbemycin A3 oxime; (6R,25R)-5-Demethoxy-28-deoxy-6,28-epoxy-5-(hydroxyimino)-25-methylmilbemycin B |
| Storage | Store at -20°C |
| IUPAC Name | (1R,4S,5'S,6R,6'R,8R,10E,13R,14E,16E,20R,24S)-24-hydroxy-21-hydroxyimino-5',6',11,13,22-pentamethylspiro[3,7,19-trioxatetracyclo[15.6.1.14,8.020,24]pentacosa-10,14,16,22-tetraene-6,2'-oxane]-2-one |
| Canonical SMILES | CC1CCC2(CC3CC(O2)CC=C(CC(C=CC=C4COC5C4(C(C=C(C5=NO)C)C(=O)O3)O)C)C)OC1C |
| InChI | InChI=1S/C31H43NO7/c1-18-7-6-8-23-17-36-28-27(32-35)21(4)14-26(31(23,28)34)29(33)37-25-15-24(10-9-19(2)13-18)39-30(16-25)12-11-20(3)22(5)38-30/h6-9,14,18,20,22,24-26,28,34-35H,10-13,15-17H2,1-5H3/b7-6+,19-9+,23-8+,32-27?/t18-,20-,22+,24+,25-,26-,28+,30-,31+/m0/s1 |
| InChI Key | VDBGCWFGLMXRIK-FJZHFHHPSA-N |
| Source | Semi-synthetic |
Properties
| Appearance | Solid |
| Antibiotic Activity Spectrum | parasites |
| Boiling Point | 751.3±60.0°C at 760 mmHg |
| Density | 1.3±0.1 g/cm3 |
| Solubility | Soluble in ethanol, methanol, DMF, DMSO |
Reference Reading
1. Canine angiostrongylosis: an emerging disease in Europe
Jenny R Helm,Paul Wotton,Rory Bell,Eric R Morgan,Mark W Jackson J Vet Emerg Crit Care (San Antonio) . 2010 Feb;20(1):98-109. doi: 10.1111/j.1476-4431.2009.00494.x.
Objective:The aim of this article is to review Angiostrongylus vasorum infection in dogs, including the life cycle, signalment, clinical signs, diagnosis, and treatment. Apparent changes in the epidemiology of this unique parasite are considered, alongside information available regarding its recent geographic spread.Etiology:A. vasorum is a metastrongyloid parasite capable of causing an array of clinical problems in dogs, including cardiorespiratory, coagulopathic, and neurologic signs. Currently, the parasite has a worldwide distribution; however, it usually arises in small pockets of enzootic foci. Recent reports suggest a changing distribution of this parasite, which has renewed interest in its epidemiology and in the risk of expansion to new areas including mainland North America.Diagnosis:A definitive diagnosis of angiostrongylosis is usually made using the modified Baermann technique either using feces or tracheobronchial secretions; however, this review also discusses novel methods such as serologic and molecular techniques.Therapy:Once a diagnosis of angiostrongylosis is made, prompt treatment should follow with anthelmintic drugs (such as moxidectin/imidacloprid, milbemycin oxime, or fenbendazole) and supportive care dependent upon the patient's clinical signs. Currently, there is no proven prophylactic regime.Prognosis:The prognosis appears to be very dependent upon the severity of clinical signs at presentation. A. vasorum can be fatal and death may be sudden. However, if a prompt diagnosis is made and appropriate treatment is administered complete clinical resolution is possible.
2. New approaches to the treatment of canine demodicosis
M Paradis Vet Clin North Am Small Anim Pract . 1999 Nov;29(6):1425-36. doi: 10.1016/s0195-5616(99)50136-8.
Topical amitraz is the only approved treatment for CGD; however, it is not always effective or well tolerated. Extra-label use of amitraz, milbemycin oxime, ivermectin, and moxidectin may be effective therapeutical alternatives for dogs with resistant CGD or dogs that have an intolerance to the licensed amitraz protocol. It appears that oral administration of milbemycin oxime (1-2 mg/kg), ivermectin (400-600 micrograms/kg), and moxidectin (400 micrograms/kg) daily is a practical therapeutical alternative and would provide similar cure rates. Nevertheless, milbemycin oxime is expensive, ivermectin is potentially more toxic, and only limited information is available on moxidectin. The average treatment duration with these new regimens is 4 months, with an expected range of 3 to 10 months. Treatment should be administered daily for a minimum of 3 months and for at least 1 month after a series of negative skin scrapings. For chronic cases or cases that take a relatively long time to respond to therapy, 2 to 3 months of treatment beyond negative scrapings may be more appropriate. Dogs with CGD always approach clinical normalcy weeks to months before negative skin scrapings are obtained. All dogs respond at their own rate; as long as the skin scrapings at each visit show fewer mites, the current therapy should be continued for an additional month. If the mite count starts to increase, this may suggest that the treatment protocol is not being followed or it may be that the therapy chosen was suboptimally effective. Although CGD is still a disease that is not easily treated, the prognosis for dogs with this disorder has dramatically improved in the past few years. It must be remembered, however, that the treatment alternatives for CGD described above are not approved and should not be used unless the approved therapeutical regimen has failed.
3. In vitro effects of milbemycin oxime: mechanism of action against Angiostrongylus cantonensis and Dirofilaria immitis
M Terada,H H Lee Parasitol Res . 1992;78(4):349-53. doi: 10.1007/BF00937095.
The neuropharmacological mechanisms underlying the action of milbemycin oxime on the motility of Angiostrongylus cantonensis and Dirofilaria immitis were examined in vitro. In A. cantonensis, milbemycin oxime caused inhibitory effects at low concentrations of > or = 10(-9) g/ml, and paralysis was elicited at 10(-8) - 10(-6) g/ml. The paralysis was antagonized by picrotoxin and bicuculline but not by dibenamine. In addition, stimulatory effects were observed when the antibiotic was used at higher concentrations of 3-5 x 10(-6) g/ml, and the action was antagonized by strychnine. Both effects were also observed in the preparation contracted by eserine or pyrantel. When D. immitis was treated with milbemycin oxime at concentrations of 10(-7) and 3-5 x 10(-6) g/ml, only slight inhibitory and stimulatory effects, respectively, were observed. These effects were partially antagonized by picrotoxin and strychnine, respectively. These results suggest that the inhibitory and stimulatory actions of milbemycin oxime are caused through gabergic and cholinergic mechanisms in A. cantonensis and D. immitis.
4. Treatment of demodicosis in dogs: 2011 clinical practice guidelines
Ralf S Mueller,Manon Paradis,Michael A Shipstone,Stephen Lemarie,Lluís Ferrer,Birgit Holm,Emmanuel Bensignor Vet Dermatol . 2012 Apr;23(2):86-96, e20-1. doi: 10.1111/j.1365-3164.2011.01026.x.
Background and objectives:These guidelines were written by an international group of specialists with the aim to provide veterinarians with current recommendations for the diagnosis and treatment of canine demodicosis.Methods:Published studies of the various treatment options were reviewed and summarized. Where evidence in form of published studies was not available, expert consensus formed the base of the recommendations.Results:Demodicosis can usually be diagnosed by deep skin scrapings or trichograms; in rare cases a skin biopsy may be needed for diagnosis. Immune suppression due to endoparasitism or malnutrition in young dogs and endocrine diseases, neoplasia and chemotherapy in older dogs are considered predisposing factors and should be diagnosed and treated to optimize the therapeutic outcome. Dogs with disease severity requiring parasiticidal therapy should not be bred. Secondary bacterial skin infections frequently complicate the disease and require topical and/or systemic antimicrobial therapy. There is good evidence for the efficacy of weekly amitraz rinses and daily oral macrocyclic lactones such as milbemycin oxime, ivermectin and moxidectin for the treatment of canine demodicosis. Weekly application of topical moxidectin can be useful in dogs with milder forms of the disease. There is some evidence for the efficacy of weekly or twice weekly subcutaneous or oral doramectin. Systemic macrocyclic lactones may cause neurological adverse effects in sensitive dogs, thus a gradual increase to the final therapeutic dose may be prudent (particularly in herding breeds). Treatment should be monitored with monthly skin scrapings and extended beyond clinical and microscopic cure to minimize recurrences.
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Bio Calculators
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Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
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Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
