Avermectin A1a, 25-cyclohexyl-5-O-demethyl-25-de(1-methylpropyl)-
Doramectin
CAS: 117704-25-3
Molecular Formula: C50H74O14
Avermectin A1a, 25-cyclohexyl-5-O-demethyl-25-de(1-methylpropyl)- - Names and Identifiers
| Name | Doramectin |
| Synonyms | Dectoma UK-67994 Doramectin doramectine DONGGUAI.P.E 25-Cclohexyl-avermectin B1 25-CYCLOHEXYL-5-O-DEMETHYL-25-DE(1-METHYLPROPYL)AVERMECTIN 25-Cyclohexyl-5-O-demethyl-25-de(1-methylpropyl)avermectin A1A Avermectin A1a, 25-cyclohexyl-5-O-demethyl-25-de(1-methylpropyl)- Avermectin A1a, 25-cyclohexyl-5-O-demethyl-25-de(1- methylpropyl)- (5'S,6S,6'R,11R,13S,15S,17aR,20R,20aR,20bS)-6'-cyclohexyl-20,20b-dihydroxy-5',6,8,19-tetramethyl-17-oxo-5',6,6',10,11,14,15,17,17a,20,20a,20b-dodecahydro-2H,7H-spiro[11,15-methanofuro[4,3,2-pq][2,6]benzodioxacyclooctadecine-13,2'-pyran]-7-yl (4xi)-2,6-dideoxy-4-O-(2,6-dideoxy-3-O-methyl-α-L-arabino-hexopyranosyl)-3-O-methyl-α-L-threo-hexopyranoside |
| CAS | 117704-25-3 |
| EINECS | 601-490-4 |
| InChI | InChI=1/C50H74O14/c1-27-13-12-16-34-26-57-47-42(51)30(4)21-37(50(34,47)54)48(53)60-36-22-35(63-49(25-36)20-19-29(3)45(64-49)33-14-10-9-11-15-33)18-17-28(2)44(27)61-41-24-39(56-8)46(32(6)59-41)62-40-23-38(55-7)43(52)31(5)58-40/h12-13,16-17,19-21,27,29,31-33,35-47,51-52,54H,9-11,14-15,18,22-26H2,1-8H3/b13-12+,28-17+,34-16-/t27-,29-,31-,32-,35+,36-,37-,38-,39-,40-,41-,42+,43-,44?,45-,46?,47+,49+,50+/m0/s1 |
| InChIKey | QLFZZSKTJWDQOS-YDBLARSUSA-N |
Avermectin A1a, 25-cyclohexyl-5-O-demethyl-25-de(1-methylpropyl)- - Physico-chemical Properties
| Molecular Formula | C50H74O14 |
| Molar Mass | 899.11 |
| Density | 1.25±0.1 g/cm3(Predicted) |
| Melting Point | 116-1190C |
| Boling Point | 967.4±65.0 °C(Predicted) |
| Flash Point | 274.4°C |
| Solubility | Soluble in water (partly), chloroform, and methanol., Soluble in water (partly), chlorofo |
| Vapor Presure | 0Pa at 20℃ |
| Appearance | White to white-like powder |
| Color | white |
| pKa | 12.42±0.70(Predicted) |
| Storage Condition | Sealed in dry,Store in freezer, under -20°C |
| Refractive Index | 1.579 |
| MDL | MFCD00894747 |
| Physical and Chemical Properties | It is a yellowish brown powder produced by the fermentation of a new strain of Streptomyces averinces (Streptomyces arermi-tilis) with very low solubility in water. |
| Use | For the new, broad-spectrum anti-parasitic drugs, gastrointestinal nematodes, pulmonary nematodes, mites, ticks and wounds such as maggots have high efficiency, for the treatment of livestock nematode disease and acariasis and other external parasitic diseases, mainly applicable to cattle and pigs. |
| In vivo study | Doramectin (10 mg/kg) is active in vivo with worm burden reductions of 60.1% in worm burden reductions of S.mansoni-infected mice. |
Avermectin A1a, 25-cyclohexyl-5-O-demethyl-25-de(1-methylpropyl)- - Risk and Safety
| Risk Codes | R25 - Toxic if swallowed R50/53 - Very toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment. R36/37/38 - Irritating to eyes, respiratory system and skin. |
| Safety Description | S33 - Take precautionary measures against static discharges. S45 - In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) S60 - This material and its container must be disposed of as hazardous waste. S61 - Avoid release to the environment. Refer to special instructions / safety data sheets. S36/37 - Wear suitable protective clothing and gloves. S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. |
| UN IDs | UN 2811 6.1/PG 3 |
| WGK Germany | 3 |
| HS Code | 29419090 |
Avermectin A1a, 25-cyclohexyl-5-O-demethyl-25-de(1-methylpropyl)- - Reference
| Reference Show more | 1. [IF=7.658] Xuan Zhang et al."Inhibition of TMEM16A Ca2+-activated Cl− channels by avermectins is essential for their anticancer effects."Pharmacol Res. 2020 Jun;156:104763 |
Avermectin A1a, 25-cyclohexyl-5-O-demethyl-25-de(1-methylpropyl)- - Introduction
Doramectin is a mutational biosynthetic antiparasitic antibiotic structurally related to the avermectins.
Last Update：2022-10-16 17:12:26
Avermectin A1a, 25-cyclohexyl-5-O-demethyl-25-de(1-methylpropyl)- - Reference Information
| LogP | 4.39-4.43 at 25℃ |
| introduction | doramectin (Doramectin) is a new generation of macrolide antiparasitic drug developed by American Shuoteng (formerly Pfizer) at the end of last century. It is an avermectin antibiotic fermented by a new strain of genetically recombined Streptomyces avermectin, it is considered to be one of the best antiparasitic drugs in the avermectin family. Compared with other ivermectin products, doramectin has high blood concentration in the body, slow elimination, long efficacy maintenance time, a wider spectrum of insect resistance, no allergic reactions and other characteristics, and can be used as a good alternative to ivermectin. Parasitic drugs. Doramectin is a new type of avermectin antiparasitic drug. Its deworming effect is similar to that of ivermectin. It can inhibit the transmission of nerve impulses between neuromuscles and cause the worm to paralyze and leave the host and die. However, due to the high blood concentration of doramectin in the body, the elimination is slower (the half-life of doramectin is 5.7d, and the half-life of ivermectin is 4.2d). The maintenance time of the drug effect is prolonged, so the deworming effect is better, and no allergic reaction occurs, it is safer to use. Clinical practice has proved that for mild patients, a dose of 300 μg/kg(300 μg/kg body weight) is recommended, while for severe patients, a dose of 400 μg/kg(400 μg/kg body weight) is recommended. |
| Chemical structure | Doramectin is a macrolide drug of the avermectin family, which is very similar in structure to ivermectin. As shown in the figure, doramectin C25 is cyclohexane, ivermectin is a mixture of several homologs, and its highly active component B1a (content ratio 80%) C25 is CH(CH3)C2H5, and the other component B1b (proportion 20%) C25 is CH(CH3)-CH3. Doramectin C22 and C23 are double bonds, while ivermectin is single bond. The highest blood concentration of doramectin is twice that of ivermectin. Its effective blood concentration is 18 days, while ivermectin is 12 days. The reason is that the 25th carbon of doramectin has a non-polar six-carbon ring, which improves its pharmacokinetics. In addition, the unique oil adjuvant formula of doramectin also makes the drug more long-lasting. Ivermectin injection can only be injected subcutaneously, which is quite difficult for large pigs (due to subcutaneous injection needs to be Baoding), and the change of doramectin administration method greatly improves work efficiency. |
| pharmacological effects | [chemical properties] slightly yellowish brown powder with extremely low solubility in water. Doramectin is used to treat in vitro parasitic diseases such as livestock nematodes and mites. It is obtained by the fermentation of a new strain of genetically recombined Streptomyces averiformis (Streptomyces avermitilis). The main difference from ivermectin is that the C25 position is cyclohexyl substitution. It is a new, broad-spectrum antiparasitic drug. It is effective against gastrointestinal nematodes, pulmonary nematodes, eye worms, lice, ticks, mites and maggot wounds, it also has a good repellent effect on parasites in vivo and in vitro, especially certain nematodes (roundworms) and arthropods, but it is not effective on tapeworms, trematodes and protozoa. Its mechanism of action is mainly to increase the release of the inhibitory transmitter gamma aminobutyric acid (GABA), thereby blocking the transmission of nerve signals, causing muscle cells to lose their ability to contract, and leading to the death of the worm. The peripheral neurotransmitter of mammals is acetylcholine, which will not be affected by doramectin. Doramectin is not easy to penetrate the blood-brain barrier, has minimal damage to the central nervous system, and is safer for livestock. The main feature is that the blood concentration and half-life are higher or twice longer than ivermectin. The United States has approved injection for cattle and pigs and pouring agents for cattle. |
| Use effect | Doramectin is an internal and external parasite and a killer, which is effective against nematodes and arthropods. At present, the anthelmintic drugs commonly used in the pig industry in my country are: internal parasite drugs: prothiamidazole, levamisole, trichlorfon, hygromycin, ivermectin, and avermectin. External parasite drugs: trichlorfon, amitraz, diazinon, pyrethroids, avermectin, ivermectin. Doramectin has a good effect on pig digestive tract nematodes. It is reported that pigs are injected intramuscularly at a dose of 0.3 mg/kg body weight. Artificial infection and natural infection cases are 7 days, 14 days and 2l days after administration. The weight gain was significantly higher than that of the control group (pigs P<0.0001); compared with the control group, the worms were 100% expelled, and no side effects occurred. In the treatment of pig scabies mite, there are good effects from suckling piglets to sows. After artificial infection of scabies mite, it is administered by intramuscular injection according to 0.3 mg/kg body weight. After 4 weeks of testing, the results have obvious effects on skin inflammation, injury and elimination of inter-pig worm infection (P<0.05). In the treatment of kidney worms in pregnant sows, the neck was injected at a dose of 0.3 mg/kg. When tested on the 56th and 57th days, the detection rate of urine eggs was 0, and the removal rate was 100%. The control group has 3762 eggs per milliliter of urine. It has the same effect on pig lung worms, pig lice, etc. According to the antiparasitic activity of the tissue drug concentration greater than l ng/g, the validity period of the drug can be evaluated. The duration of doramectin concentration greater than 1 ng/g is 26 days for skin, 38 days for lung, 38 days for gastrointestinal mucosa, and 38 days for anachastric mucosa. It can be seen that doramectin is larger than l ng/g in digestive tract mucosa and lung tissue for 38 days, 20 days more than ivermectin. Therefore, doramectin has a significantly stronger effect on parasites than ivermectin, and the effective time to prevent parasites from reinfection is longer. |
| precautions | 1. dorapectin is not stable in nature and decomposes and inactivates rapidly under sunlight. its remaining drugs are toxic to fish and aquatic organisms, so attention should be paid to water source protection. 2, pouring agent: after the application of cattle, do not rain within 6 hours. 3, be careful with dogs. 4. Place this product out of reach of children. Operators should not eat or smoke when using this product. Wash hands after operation. 5. the remaining drugs are toxic to fish and aquatic organisms, so attention should be paid to the protection of water resources. 6, drug withdrawal period, 35 days for cattle and 24 days for pigs. |
| biological activity | Doramectin are derivatives of Ivermectin (HY-15310). Doramectin is an effective antiparasitic antibiotic. Doramectin has anti-streptococcal effect in NMRI mouse infection model. |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-09 02:00:06
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