Doramectin
[CAS# 117704-25-3]

Identification

• Classification: API >> Antiparasitic drug >> Anthelmintic medications
• Name: Doramectin
• Synonyms: (1'R,2R,3S,4'S,6S,8'R,10'E,12'S,13'S,14'E,16'E,20'R,21'R,24'S)-2-cyclohexyl-21',24'-dihydroxy-12'-[(2R,4S,5S,6S)-5-[(2S,4S,5S,6S)-5-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy-4-methoxy-6-methyloxan-2-yl]oxy-3,11',13',22'-tetramethylspiro[2,3-dihydropyran-6,6'-3,7,19-trioxatetracyclo[15.6.1.14,8.020,24]pentacosa-10,14,16,22-tetraene]-2'-one
• Molecular Formula: C₅₀H₇₄O₁₄
• Molecular Weight: 899.11
• CAS Registry Number: 117704-25-3
• EC Number: 601-490-4
• SMILES: C[C@H]1/C=C/C=C/2CO[C@H]3[C@@]2([C@@H](C=C([C@H]3O)C)C(=O)O[C@H]4C[C@@H](C/C=C(/[C@H]1O[C@H]5C[C@@H]([C@H]([C@@H](O5)C)O[C@H]6C[C@@H]([C@H]([C@@H](O6)C)O)OC)OC)C)O[C@]7(C4)C=C[C@@H]([C@H](O7)C8CCCCC8)C)O

Properties

• Density: 1.3±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.580, Calc.^*
• Boiling Point: 967.4±65.0 °C (760 mmHg), Calc.^*
• Flash Point: 274.4±27.8 °C, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS06;GHS07;GHS08;GHS09 Danger
• Risk Statements: H300-H301-H302-H360-H361-H362-H370-H372-H400-H410
• Safety Statements: P203-P260-P263-P264-P270-P273-P280-P301+P316-P301+P317-P308+P316-P318-P319-P321-P330-P391-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Chronic hazardous to the aquatic environment	Aquatic Chronic	1	H410
Acute hazardous to the aquatic environment	Aquatic Acute	1	H400
Acute toxicity	Acute Tox.	3	H301
Specific target organ toxicity - single exposure	STOT SE	1	H370
Reproductive toxicity	Repr.	1B	H360
Reproductive toxicity	Lact.	-	H362
Acute toxicity	Acute Tox.	4	H302
Specific target organ toxicity - repeated exposure	STOT RE	1	H372
Acute toxicity	Acute Tox.	2	H300
Reproductive toxicity	Repr.	2	H361
Acute toxicity	Acute Tox.	3	H331
Acute toxicity	Acute Tox.	1	H300

Discovery and Applications

Doramectin, a member of the avermectin class of compounds, was discovered through research efforts aimed at developing novel antiparasitic agents. It was first synthesized and characterized by scientists at Merck & Co. in the late 1980s. The discovery of doramectin stemmed from the screening of fermentation products derived from Streptomyces avermitilis, a soil bacterium known for producing potent anthelmintic compounds. Doramectin emerged as a promising candidate due to its potent antiparasitic activity and favorable pharmacokinetic properties.

Doramectin is widely used in veterinary medicine for the treatment and control of parasitic infections in livestock, including cattle, sheep, and swine. It is effective against a broad spectrum of internal and external parasites, including gastrointestinal nematodes, lungworms, mites, and ticks. Doramectin's efficacy in controlling parasitic infections contributes to improved animal health and productivity in livestock farming operations. In addition to livestock, doramectin is also used in companion animals, particularly in dogs and horses, for the prevention and treatment of parasitic infestations. It is effective against common parasites such as heartworms, intestinal worms, mites, and ticks. Doramectin formulations for companion animals are available in various formulations, including oral and topical preparations. Doramectin's broad spectrum of activity extends to wildlife species susceptible to parasitic infections. Wildlife conservationists and veterinarians utilize doramectin to control parasites in captive and free-ranging wildlife populations, contributing to the preservation of biodiversity and ecosystem health. The control of parasites in livestock and companion animals with doramectin also has indirect benefits for public health. By reducing the prevalence of zoonotic parasites and limiting the spread of parasitic diseases from animals to humans, doramectin plays a role in safeguarding public health and minimizing the risk of transmission of parasitic infections.

References

2016. Finafloxacin. Pharmaceutical Substances.
URL: https://pharmaceutical-substances.thieme.com/ps/search-results?docUri=KD-06-0134

2020. Synthetic Approaches to Contemporary Drugs that Contain the Cyclopropyl Moiety. Synthesis, 52(11).
DOI: 10.1055/s-0039-1690058