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Chemistry

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Also known as: 40596-69-8, Juvemon, Dianex, Kabat, Apex, Diacon
Molecular Formula
C19H34O3
Molecular Weight
310.5  g/mol
InChI Key
NFGXHKASABOEEW-LDRANXPESA-N
FDA UNII
8B830OJ2UX

Methoprene
Juvenile hormone analog and insect growth regulator used to control insects by disrupting metamorphosis. Has been effective in controlling mosquito larvae.
1 2D Structure

Methoprene

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
propan-2-yl (2E,4E)-11-methoxy-3,7,11-trimethyldodeca-2,4-dienoate
2.1.2 InChI
InChI=1S/C19H34O3/c1-15(2)22-18(20)14-17(4)11-8-10-16(3)12-9-13-19(5,6)21-7/h8,11,14-16H,9-10,12-13H2,1-7H3/b11-8+,17-14+
2.1.3 InChI Key
NFGXHKASABOEEW-LDRANXPESA-N
2.1.4 Canonical SMILES
CC(C)OC(=O)C=C(C)C=CCC(C)CCCC(C)(C)OC
2.1.5 Isomeric SMILES
CC(C)OC(=O)/C=C(\C)/C=C/CC(C)CCCC(C)(C)OC
2.2 Other Identifiers
2.2.1 UNII
8B830OJ2UX
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Altosid

2. Altosid Ps 10

3. Altosid Ps-10

4. Altosid Ps10

5. Zr 515

6. Zr-515

7. Zr515

2.3.2 Depositor-Supplied Synonyms

1. 40596-69-8

2. Juvemon

3. Dianex

4. Kabat

5. Apex

6. Diacon

7. Pharoid

8. Precor

9. Manta

10. Minex

11. Methoprene S

12. Starbar Inhibitor

13. Manta (hormone)

14. Altosid Igr

15. Apex (pesticide)

16. Methoprene [inn]

17. Zr 515

18. Altosid

19. Altosid Sr 10

20. Altosid Liquid Larvicide

21. 36557-27-4

22. Propan-2-yl (2e,4e)-11-methoxy-3,7,11-trimethyldodeca-2,4-dienoate

23. Isopropyl 11-methoxy-3,7,11-trimethyldodeca-2,4-dienoate

24. Bioprene Bm Fire Ant Killer Bait

25. Oms 1697

26. Zpa 1019

27. Ent 70460

28. Isopropyl (2e,4e)-11-methoxy-3,7,11-trimethyldodeca-2,4-dienoate

29. (e,e)-1-methylethyl 11-methoxy-3,7,11-trimethyl-2,4-dodecadienoate

30. 2,4-dodecadienoic Acid, 11-methoxy-3,7,11-trimethyl-, 1-methylethyl Ester, (2e,4e)-

31. (e,e)-isopropyl 11-methoxy-3,7,11-trimethyl-2,4-dodecadienoate

32. Isopropyl (2e,4e)-11-methoxy-3,7,11-trimethyl-2,4-dodecadienoate

33. Isopropyl (ee)-(rs)-11-methoxy-3,7,11-trimethyldodeca-2,4-dienoate

34. 2,4-dodecadienoic Acid, 11-methoxy-3,7,11-trimethyl-, 1-methylethyl Ester, (e,e)-

35. 8b830oj2ux

36. Chebi:34839

37. 11-methoxy-3,7,11-trimethyl-2,4-dodecadienoic Acid Isopropyl Ester

38. Zr-515

39. Methoprene (inn)

40. Ncgc00090777-05

41. Yuvemon

42. 1-methylethyl 11-methoxy-3,7,11-trimethyl-2,4-dodecadienoate

43. 2,4-dodecadienoic Acid, 11-methoxy-3,7,11-trimethyl-, 1-methylethyl Ester

44. Isopropyl (2e,4e)-(7s)-11-methoxy-3,7,11-trimethyl-2,4-dodecadienoate

45. Dsstox_cid_12627

46. Dsstox_rid_79012

47. Dsstox_gsid_32627

48. Manina

49. Zodiac

50. Metoprag 20ce

51. Methoprenum

52. Metopreno

53. Caswell No. 028aaa

54. Methoprenum [inn-latin]

55. Metopreno [inn-spanish]

56. Dl-isopropyl 11-methoxy-3,7,11-trimethyl-trans-trans-2,4-dodecadienoate

57. (e,e)-11-methoxy-3,7,11-trimethyl-2,4-dodecadienoic Acid 1-methylethyl Ester

58. Methoprene [iso]

59. Cas-40596-69-8

60. Hsdb 6926

61. Methoprene (unspecified)

62. Einecs 254-993-2

63. Isopropylmethoxytrimethyldodecadienoate

64. Epa Pesticide Chemical Code 105401

65. Unii-8b830oj2ux

66. Methoprene [ansi:bsi:iso]

67. Zpa-1019

68. Ent-70460

69. Sb-515

70. 52020-07-2

71. Ro 10-6425

72. Isopropyl-11-methoxy-3,7,11-trimethyldodeca-2,4-dienoate

73. Methoprene [mi]

74. Methoprene [jan]

75. Dl-isopropyl 11-methoxy-3,7,11-trimethyl-trans-2,4-dodecadienoate

76. Isopropyl(2e,4e)-11-methoxy-3,7,11-trimethyl-2,4-dodecadienoate

77. Methoprene [hsdb]

78. 2,4-dodecadienoic Acid, 11-methoxy-3,7,11-trimethyl-, Isopropyl Ester

79. Methoprene [mart.]

80. Zodiac [veterinary] (tn)

81. Methoprene [who-dd]

82. Schembl19795

83. Mls001055477

84. Chembl291057

85. Dtxsid8032627

86. Chebi:39257

87. 2,4-dodecadienoic Acid, 11-methoxy-3,7,11-trimethyl-, 1-methylethyl Ester, (2z,4e,7s)-

88. Hms3039c11

89. Hy-b1161

90. Tox21_111019

91. Tox21_200654

92. Stk677200

93. Akos005594513

94. Isopropyl (2e,4e,7rs)-11-methoxy-3,7,11-trimethyl-2,4-dodecadienoate

95. Tox21_111019_1

96. Cs-4762

97. Methoprene 1000 Microg/ml In Acetone

98. Nsc 758655

99. (2e,4e)-11-methoxy-3,7,11-trimethyl-2,4-dodecadienoic Acid 1-methylethyl Ester

100. Ncgc00090777-01

101. Ncgc00090777-02

102. Ncgc00090777-03

103. Ncgc00090777-04

104. Ncgc00090777-06

105. Ncgc00258208-01

106. Ncgc00263657-01

107. 41205-06-5

108. Smr001227198

109. Methoprene, Pestanal(r), Analytical Standard

110. D08200

111. Sr-01000854669

112. Q2329841

113. Sr-01000854669-2

114. Q27119793

115. Propan-2-yl 11-methoxy-3,7,11-trimethyldodeca-2,4-dienoate

116. (2e,4e)-isopropyl 11-methoxy-3,7,11-trimethyldodeca-2,4-dienoate

117. 11-methoxy-3,7,11-trimethyl-2,4-dodecadienoic Acid, 1-methylethyl Ester

118. (2e,4e)-3,7,11-trimethyl-11-methoxydodeca-2,4-dienoic Acid 1-methylethyl Ester

119. 1-methylethyl (2e,4e)-11-methoxy-3,7,11-trimethyl-2,4-dodecadienoate

120. Isopropyl (e,e)-(rs)-11-methoxy-3,7,11-trimethyldodeca-2,4-dienoate

2.4 Create Date
2005-03-27
3 Chemical and Physical Properties
Molecular Weight 310.5 g/mol
Molecular Formula C19H34O3
XLogP35.5
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count3
Rotatable Bond Count11
Exact Mass310.25079494 g/mol
Monoisotopic Mass310.25079494 g/mol
Topological Polar Surface Area35.5 Ų
Heavy Atom Count22
Formal Charge0
Complexity378
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count1
Defined Bond Stereocenter Count2
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Therapeutic Uses

/EXPL THER/ The effects of methoprene, a juvenile hormone analogue (JHA), on Trypanosoma cruzi bloodstream trypomastigotes (Tulahuen strain, Tul 2 stock) were studied. It was observed that 150 uM of methoprene in in vitro experiments cause cellular death of T. cruzi. In contrast, methoprene was not able to clear bloodstream trypomastigotes in in vivo experiments, but it was observed a decrease of parasitemia levels of infected mice treated with 200 ug of methoprene/mouse/day during 5 days. According to these results and the low toxicity of methoprene, we suggest that this compound will serve as an effective agent to sterilize blood for transfusions.

PMID:12128051 Esteva M et al; Exp Parasitol 100 (4): 248-51 (2002)


/EXPL THER/ Drug therapy for the treatment of African sleeping sickness is limited by toxicity and resistance and in the last 50 years only one new drug has been introduced for the treatment of the human disease. We report that the juvenile hormone analog, methoprene, and several structurally related isoprenoid compounds kill Trypanosoma brucei in culture. Of the other isoprenoids tested, juvenile hormone III and mammalian retinoid X receptor ligands were the most potent trypanocides. Both the procyclic forms and the bloodstream trypomastigotes are killed by these compounds with LD50 values of 5-30 uM. Of the two methoprene stereoisomers, the EE form was the most active, suggesting that a protein target may be involved in mediating effects of these analogues against the parasite. Methoprene was not, however, able to clear trypanosomes from the blood of infected mice. Methoprene acid, the immediate downstream metabolite of methoprene, is not an effective anti-trypanosomal agent, suggesting that in the mice methoprene is converted to an inactive compound. Since methoprene and its analogues have low and well characterized toxicity in mammals these studies stress the importance of further exploring these isoprenoids as lead compounds for the treatment of African sleeping sickness.

PMID:9371088 Harmon MA et al; Exp Parasitol 87 (3): 229-236 (1997)


5 Pharmacology and Biochemistry
5.1 Absorption, Distribution and Excretion

When (14)C methoprene was administered orally to rats, slightly less than 20% was excreted within 5 days in the urine and a similar amount in feces and almost 40% was excreted as (14)C02. About 17% was retained in the body. Highest concentrations were in liver (84.5 ppm), kidneys (29 ppm), lungs (26 ppm), fat (36.5 ppm), and the adrenal cortex (12-13 ppm). About 12 labeled compounds were detected in the urine but no unchanged methoprene was observed.

Menzie, C.M. Metabolism of Pesticides-Update III. Special Scientific Report- Wildlife No. 232. Washington, DC: U.S.Department of the Interior, Fish and Wildlife Service, 1980., p. 333


Distribution and elimination of (14)C given to chickens as methoprene (14)C (isopropyl (2E,4E)-11-methoxy-3,7,11-trimethyl-2,4-dodecadienate 5 (14)C were investigated. When about 4 mg of methoprene was given in a single oral dose to colostomized chickens, elimination of (14)C was greatest in exhaled air; however, when 105 or 107 mg of methoprene was given, elimination of (14)C was greatest in urine. Up to 19% of the (14)C from a single dose of methoprene was eliminated over a 14 day period in the eggs of laying hens, and (14)C was detected in all tissues and organs examined.

Davison KL; J Agric Food Chem 24 (3): 641-3 (1976)


When the metabolic fate of methoprene (isopropyl (2E,4E)-11-methoxy-3,7,11-trimethyl- 2,4-dodecadienoate) was studied in a guinea pig, a steer, and a cow, a rather large percentage of the radiolabel was incorporated in the tissues and respired by the animals. In the urine and feces, a small amount of radiolabel was metabolized into free primary metabolites, somewhat more was incorporated into simple glucuronides, and a considerable quantity of radiolabel was found in polar compounds, possibly complex conjugates or polar biochemicals. No methoprene was found in the urine, but approximately 40% of the radiolabel in feces was contributed by unmetabolized methoprene. The formation of conjugates and the metabolism of methoprene was more extensive in the steer than in the guinea pig.

Chamberlain WF et al; J Agric Food Chem 23 (4): 736-42 (1975)


Treatment of Leghorn chickens with a single oral dose of (5-14C)methoprene (isopropyl (2E,4E)-11-methoxy-3,7,11-trimethyl-2,4-dodecadienoate) resulted in residual radioactivity in tissues and eggs. The chemical nature of the residual radiolabel in tissue (muscle, fat, liver), eggs, and excrement was thoroughly examined at several doses (0.6 to 77 mg/kg). Although a high initial dose (59 mg/kg) resulted in methoprene residues in muscle (0.01 ppm), fat (2.13 ppm), and egg yolk (8.03 ppm), these residues of methoprene represented only 39 and 2% of the total (14)C label in fat and egg yolk, respectively. Radiolabeled natural products from extensive degradation of methoprene were by far the most important 14C residues in tissues and eggs, particularly at the lower dose of 0.6 mg/kg where (14)C cholesterol and normal (14)C fatty acids (as triglyceride) contributed 8 and 71% of the total radiolabel in egg yolk. Novel minor metabolites of methoprene were observed in lipid depots, resulting from saturation of the dienoate system. These minor metabolites were conjugated to glycerol and/or cholesterol. radioactivity were found in the bile, liver, skin, fetus, and udder. In all species, approximately 40 percent of the radioactivity in the feces was due to unchanged methoprene. No methoprene was found in the urine.

Quistad GB et al; J Agric Food Chem 24 (3): 644-8 (1976)


For more Absorption, Distribution and Excretion (Complete) data for METHOPRENE (6 total), please visit the HSDB record page.


5.2 Metabolism/Metabolites

About 4 mg (14)C methoprene was administered orally to colostomized chickens. (14)C02 was the main (14)C product detected. When large doses were given, elimination was greatest in urine and (14)C was also found in the eggs and all tissues and organs examined ... . In addition to natural (14)C cholesterol and (14)C fatty acid triglycerides, there were metabolites conjugated to glycerol and/or cholesterol. Urine ... and ... feces contained compounds ... and each had undergone considerable isomerization. About 19% of the (14)C appeared in the eggs. Most of this was associated with egg proteins. The egg yolks also had radiolabeled fatty acid glycerides and cholesterol. Blood contained radiolabeled cholesterol and traces of cholesteryl esters. Tissue residues were similar to those found in eggs.

Menzie, C.M. Metabolism of Pesticides-Update III. Special Scientific Report- Wildlife No. 232. Washington, DC: U.S.Department of the Interior, Fish and Wildlife Service, 1980., p. 333


A Hereford steer received a single oral dose of 5-(14)C-methoprene and sacrificed 2 weeks later. No primary metabolites were observed in fat, muscle, liver, lung, blood and bile. However, the majority of the tissue radioactivity was present as (14)C cholesterol. About 72% of the activity in bile appeared in cholesterol, cholic acid, and deoxycholic acid. Protein and cholesteryl esters of fatty acids also contained some radioactivity.

Menzie, C.M. Metabolism of Pesticides-Update III. Special Scientific Report- Wildlife No. 232. Washington, DC: U.S.Department of the Interior, Fish and Wildlife Service, 1980., p. 333


When administered to a lactating cow, 5-(14)C-methoprene gave rise to randomly labeled acetate. This was incorporated into milk fat which was degraded to saturated and mono and di- enoic fatty acids. Labeled lactose, lactalbumin, casein, and free and esterified cholesterol was also observed ... . Similar qualitative results were observed in urine of a guinea pig orally dosed with methoprene. Quantitative differences were observed.

Menzie, C.M. Metabolism of Pesticides-Update III. Special Scientific Report- Wildlife No. 232. Washington, DC: U.S.Department of the Interior, Fish and Wildlife Service, 1980., p. 333


Studies with housefly microsomal enzymes showed that the Beta-esterases present did not appreciably hydrolyze methoprene whereas other analogs were metabolized. Microsomal oxidase activity against juvenile hormone analogs was greater in resistant fly strains. ... Branched chain esters of methoprene analogs did not show significant difference in hydrolysis by housefly microsomal esterases. Methoprene was effective at 0.1 ug/pupa while others were ineffective at 10 ug/pupa.

Menzie, C.M. Metabolism of Pesticides-Update III. Special Scientific Report- Wildlife No. 232. Washington, DC: U.S.Department of the Interior, Fish and Wildlife Service, 1980., p. 333


For more Metabolism/Metabolites (Complete) data for METHOPRENE (15 total), please visit the HSDB record page.


5.3 Biological Half-Life

The degradation of methoprene by unidentified pond organisms was studied. The half-life in the pond water was about 30 h at 0.001 ppm and 40 h at 0.01 ppm.

Menzie, C.M. Metabolism of Pesticides-Update III. Special Scientific Report- Wildlife No. 232. Washington, DC: U.S.Department of the Interior, Fish and Wildlife Service, 1980., p. 333


In wheat, the half-life of methoprene was estimated to be 3 to 7 weeks, depending on moisture content. The only metabolite observed was the free acid.

Menzie, C.M. Metabolism of Pesticides-Update III. Special Scientific Report- Wildlife No. 232. Washington, DC: U.S.Department of the Interior, Fish and Wildlife Service, 1980., p. 333


5.4 Mechanism of Action

Methoprene (isopropyl (2E,4E)-11-methoxy-3,7,11-trimethyl-2,4-dodecadienoate) is an insect juvenile hormone agonist that blocks metamorphosis in some insects. Recent evidence suggests that a metabolite, methoprene acid, activates vertebrate retinoid X receptors (RXRs), and may interfere with retinoic acid-regulated developmental processes. Methoprene, methoxy-methoprene acid, and two major breakdown products were tested for their ability to interfere with retinoid-regulated pathways when using transfected cells. The CV-1 cells were transiently transfected with genes encoding RXRs and response elements attached to luciferase reporters, and retinoic acid-sensitive F9 cells were stably transfected with retinoic acid receptor (RAR)/RXR response elements attached a lacZ reporter (Sil-REM/beta-gal-NEO). Experiments confirmed that methoxy-methopreneacid acted as a ligand for RXRs and was capable of activating transcription through RAR/RXR response elements. However, neither methoprenenor the breakdown products, 7-methoxycitronellal and 7-methoxycitronellic acid, activated transcription in transfected CV-1 or F9 cells.Methoprene and methoxy-methoprene acid may interfere with the conversion of all-trans-retinol and all-trans-retinaldehyde to all-trans-retinoic acid in the F9-derived cell line. Methoprene was as effective as the retinol dehydrogenase inhibitor citral in blocking the retinol-induced transcription of RAR/RXR-regulated reporter genes, whereas methoxy-methoprene acid blocked transcription stimulated by retinaldehyde.

PMID:15180384 Schoff PK, Ankley GT; Environ Toxicol Chem 23 (5): 1305-10 (2004)


In holometabolous insects such as mosquito, Aedes aegypti, midgut undergoes remodeling during metamorphosis. Insect metamorphosis is regulated by several hormones including juvenile hormone (JH) and 20-hydroxyecdysone (20E). The cellular and molecular events that occur during midgut remodeling were investigated by studying nuclear stained whole mounts and cross-sections of midguts and by monitoring the mRNA levels of genes involved in 20E action in methoprene-treated and untreated Ae. aegypti. We used JH analog, methoprene, to mimic JH action. In Ae. aegypti larvae, the programmed cell death (PCD) of larval midgut cells and the proliferation and differentiation of imaginal cells were initiated at about 36 hr after ecdysis to the 4th instar larval stage (AEFL) and were completed by 12 hr after ecdysis to the pupal stage (AEPS). In methoprene-treated larvae, the proliferation and differentiation of imaginal cells was initiated at 36h AEFL, but the PCD was initiated only after ecdysis to the pupal stage. However, the terminal events that occur for completion of PCD during pupal stage were blocked. As a result, the pupae developed from methoprene-treated larvae contained two midgut epithelial layers until they died during the pupal stage. Quantitative PCR analyses showed that methoprene affected midgut remodeling by modulating the expression of ecdysone receptor B, ultraspiracle A, broad complex, E93, ftz-f1, dronc and drice, the genes that are shown to play key roles in 20E action and PCD. Thus, JH analog, methoprene acts on Ae. aegypti by interfering with the expression of genes involved in 20E action resulting in a block in midgut remodeling and death during pupal stage.

PMID:16829058 Wu Y et al; Mech Dev 123 (7): 530-47 (2006)


... Here, a major malaria vector, Anopheles gambiae Giles, was used as a model insect to study the action of methoprene on female reproduction. Ecdysteroid titers and expression profiles of ecdysone-regulated genes were determined before and after a blood meal. An ecdysteroid peak was detected at 12 hr post blood meal (PBM). The maximum expression of ecdysone-regulated genes, such as ecdysone receptor (EcR), hormone receptor 3 (HR3) and vitellogenin (Vg) gene, coincided with the ecdysteroid peak. Interestingly, topical application of methoprene at 6 hr PBM delayed ovarian development and egg maturation by suppressing the expression of ecdysone-regulated genes in female mosquitoes. The data suggest that ecdysteroid titers are correlated with Vg synthesis, and methoprene affects vitellogenesis by modulating ecdysteroid action in A. gambiae.

PMID:20730984 Full text: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2928151 Bai H et al; Pest Manag Sci 66 (9): 936-43 (2010)


Insect growth regulator (juvenile hormone mimic), preventing metamorphosis to viable adults when applied to larval stages.

Tomlin, C.D.S. (ed.). The Pesticide Manual - World Compendium. 10th ed. Surrey, UK: The British Crop Protection Council, 1994., p. 681


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04-Jan-2021
05-Aug-2024
KGS
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Average Price (USD/KGS)

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Total Quantity (KGS)

Total Value (USD)

Quantity (KGS) & Unit rate (USD/KGS) over time

API Imports and Exports

Importing Country Total Quantity
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(USD/KGS)
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