Spinosad

Spinosyns

Spinosyn A

Spinosyn D
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.103.254 Edit this at Wikidata
KEGG
UNII
  • A: InChI=1S/C41H65NO10/c1-10-26-12-11-13-34(52-36-17-16-33(42(5)6)23(3)48-36)22(2)37(44)32-20-30-28(31(32)21-35(43)50-26)15-14-25-18-27(19-29(25)30)51-41-40(47-9)39(46-8)38(45-7)24(4)49-41/h14-15,20,22-31,33-34,36,38-41H,10-13,16-19,21H2,1-9H3/t22-,23-,24+,25-,26+,27-,28-,29-,30-,31+,33+,34+,36+,38+,39-,40-,41+/m1/s1
    Key: SRJQTHAZUNRMPR-UYQKXTDMSA-N
  • D: InChI=1S/C42H67NO10/c1-11-26-13-12-14-35(53-37-16-15-34(43(6)7)24(4)49-37)23(3)38(45)33-20-31-29(32(33)21-36(44)51-26)17-22(2)28-18-27(19-30(28)31)52-42-41(48-10)40(47-9)39(46-8)25(5)50-42/h17,20,23-32,34-35,37,39-42H,11-16,18-19,21H2,1-10H3/t23-,24-,25+,26+,27-,28+,29-,30-,31-,32+,34+,35+,37+,39+,40-,41-,42+/m1/s1
    Key: RDECBWLKMPEKPM-PSCJHHPTSA-N
  • A: O([C@H]1C[C@]2([C@]3([C@]([C@]4(C(=C3)C(=O)[C@H](C)[C@@H](O[C@@H]5O[C@H](C)[C@@H](N(C)C)CC5)CCC[C@H](CC)OC(=O)C4)[H])(C=C[C@@]2(C1)[H])[H])[H])[H])[C@H]6[C@H](OC)[C@H](OC)[C@@H](OC)[C@H](C)O6
  • D: CC1=C[C@@]2([C@]([C@]3([C@]1(C[C@@H](O[C@H]4[C@H](OC)[C@H](OC)[C@@H](OC)[C@H](C)O4)C3)[H])[H])(C=C5[C@]2(CC(=O)O[C@@H](CC)CCC[C@H](O[C@@H]6O[C@H](C)[C@@H](N(C)C)CC6)[C@@H](C)C5=O)[H])[H])[H]
Properties
C41H65NO10 (A)
C42H67NO10 (D)
Molar mass 731.968 g·mol−1 (A)
745.995 g·mol−1 (D)
Pharmacology
QP53BX03 (WHO)
Topical, by mouth
Legal status
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Spinosad
Clinical data
AHFS/Drugs.comMonograph
Identifiers
CompTox Dashboard (EPA)
ECHA InfoCard100.103.254 Edit this at Wikidata

Spinosad is an insecticide based on chemical compounds found in the bacterial species Saccharopolyspora spinosa. The genus Saccharopolyspora was discovered in 1985 in isolates from crushed sugarcane. The bacteria produce yellowish-pink aerial hyphae, with bead-like chains of spores enclosed in a characteristic hairy sheath.[4] This genus is defined as aerobic, Gram-positive, nonacid-fast actinomycetes with fragmenting substrate mycelium. S. spinosa was isolated from soil collected inside a nonoperational sugar mill rum still in the Virgin Islands. Spinosad is a mixture of chemical compounds in the spinosyn family that has a generalized structure consisting of a unique tetracyclic ring system attached to an amino sugar (D-forosamine) and a neutral sugar (tri-Ο-methyl-L-rhamnose).[5] Spinosad is relatively nonpolar and not easily dissolved in water.[6]

Spinosad is a novel mode-of-action insecticide derived from a family of natural products obtained by fermentation of S. spinosa. Spinosyns occur in over 20 natural forms, and over 200 synthetic forms (spinosoids) have been produced in the lab.[7] Spinosad contains a mix of two spinosoids, spinosyn A, the major component, and spinosyn D (the minor component), in a roughly 17:3 ratio.[4]

  1. ^ "Natroba- spinosad suspension". DailyMed. U.S. National Library of Medicine. 28 April 2021. Retrieved 1 July 2023.
  2. ^ "Spinosad suspension". DailyMed. U.S. National Library of Medicine. 31 May 2023. Retrieved 1 July 2023.
  3. ^ "Comfortis- spinosad tablet, chewable". DailyMed. U.S. National Library of Medicine. 1 July 2021. Retrieved 1 July 2023.
  4. ^ a b Mertz F, Yao RC (January 1990). "Saccharopolyspora spinosa sp. nov. Isolated from soil Collected in a Sugar Mill Rum Still". International Journal of Systematic Bacteriology. 40 (1): 34–39. doi:10.1099/00207713-40-1-34.
  5. ^ Snyder DE, Meyer J, Zimmermann AG, Qiao M, Gissendanner SJ, Cruthers LR, et al. (December 2007). "Preliminary studies on the effectiveness of the novel pulicide, spinosad, for the treatment and control of fleas on dogs". Veterinary Parasitology. 150 (4): 345–351. doi:10.1016/j.vetpar.2007.09.011. PMID 17980490.
  6. ^ Crouse GD, Sparks TC, Schoonover J, Gifford J, Dripps J, Bruce T, et al. (February 2001). "Recent advances in the chemistry of spinosyns". Pest Management Science. 57 (2): 177–185. doi:10.1002/1526-4998(200102)57:2<177::AID-PS281>3.0.CO;2-Z. PMID 11455648.
  7. ^ Watson G (31 May 2001). "Actions of Insecticidal Spinosyns on γ-Aminobutyric Acid Responses for Small-Diameter Cockroach Neurons". Pesticide Biochemistry and Physiology. 71 (1): 20–28. Bibcode:2001PBioP..71...20W. doi:10.1006/pest.2001.2559.