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Moxidectin

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Also known as: 113507-06-5, Proheart 6, Ngu5h31yo9, Cl 301,423, Nsc-760424, (1r,4s,4'e,5's,6r,6's,8r,10e,13r,14e,16e,20r,21r,24s)-21,24-dihydroxy-4'-methoxyimino-5',11,13,22-tetramethyl-6'-[(e)-4-methylpent-2-en-2-yl]spiro[3,7,19-trioxatetracyclo[15.6.1.14,8.020,24]pentacosa-10,14,16,22-tetraene-6,2'-oxane]-2-one

Molecular Formula

C₃₇H₅₃NO₈

Molecular Weight

639.8 g/mol

InChI Key

YZBLFMPOMVTDJY-LSGXYNIPSA-N

FDA UNII

NGU5H31YO9

Moxidectin is a macrocyclic lactone derived from Streptomyces cyanogriseus with antiparasitic activity. Upon administration, moxidectin may bind to glutamate-gated chloride channels (GluCl), gamma-aminobutyric acid (GABA) receptors and/or ATP-binding cassette (ABC) transporters expressed on nematode neurons and pharyngeal muscle cells. As a result, neurons or muscle cells remain at either hyperpolarization or depolarization state, thereby resulting in muscle paralysis. Moxidectin reduces the motility and fertility of the parasite and its excretion of immunomodulatory proteins, and inhibits the release of microfilariae.

1 2D Structure

Moxidectin

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(1R,4S,4'E,5'S,6R,6'S,8R,10E,13R,14E,16E,20R,21R,24S)-21,24-dihydroxy-4'-methoxyimino-5',11,13,22-tetramethyl-6'-[(E)-4-methylpent-2-en-2-yl]spiro[3,7,19-trioxatetracyclo[15.6.1.14,8.020,24]pentacosa-10,14,16,22-tetraene-6,2'-oxane]-2-one

2.1.2 InChI

InChI=1S/C37H53NO8/c1-21(2)14-25(6)33-26(7)31(38-42-8)19-36(46-33)18-29-17-28(45-36)13-12-23(4)15-22(3)10-9-11-27-20-43-34-32(39)24(5)16-30(35(40)44-29)37(27,34)41/h9-12,14,16,21-22,26,28-30,32-34,39,41H,13,15,17-20H2,1-8H3/b10-9+,23-12+,25-14+,27-11+,38-31+/t22-,26-,28+,29-,30-,32+,33+,34+,36-,37+/m0/s1

2.1.3 InChI Key

YZBLFMPOMVTDJY-LSGXYNIPSA-N

2.1.4 Canonical SMILES

CC1CC(=CCC2CC(CC3(O2)CC(=NOC)C(C(O3)C(=CC(C)C)C)C)OC(=O)C4C=C(C(C5C4(C(=CC=C1)CO5)O)O)C)C

2.1.5 Isomeric SMILES

C[C@@H]\1C/C(=C/C[C@@H]2C[C@@H](C[C@@]3(O2)C/C(=N\OC)/[C@@H]([C@H](O3)/C(=C/C(C)C)/C)C)OC(=O)[C@@H]4C=C([C@H]([C@@H]5[C@]4(/C(=C/C=C1)/CO5)O)O)C)/C

2.2 Other Identifiers

2.2.1 UNII

NGU5H31YO9

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 5-hydroxymilbemycin Beta7

2. Cl 301,423

3. Cl 301423

4. Cydectin

5. Milbeknock

6. Milbemectin

7. Milbemycin A3

8. Milbemycin A4

9. Milbemycin Alpha1

10. Milbemycin Alpha10

11. Milbemycin Alpha11

12. Milbemycin Alpha13

13. Milbemycin Alpha14

14. Milbemycin Alpha15

15. Milbemycin Alpha2

16. Milbemycin Alpha3

17. Milbemycin Alpha4

18. Milbemycin Alpha5

19. Milbemycin Alpha6

20. Milbemycin Alpha7

21. Milbemycin Alpha8

22. Milbemycin Alpha9

23. Milbemycin B

24. Milbemycin Beta1

25. Milbemycin Beta12

26. Milbemycin Beta2

27. Milbemycin Beta3

28. Milbemycin D

29. Milbemycins

30. Mixture Of Milbemycins A3 And A4

2.3.2 Depositor-Supplied Synonyms

1. 113507-06-5

2. Proheart 6

3. Ngu5h31yo9

4. Cl 301,423

5. Nsc-760424

6. (1r,4s,4'e,5's,6r,6's,8r,10e,13r,14e,16e,20r,21r,24s)-21,24-dihydroxy-4'-methoxyimino-5',11,13,22-tetramethyl-6'-[(e)-4-methylpent-2-en-2-yl]spiro[3,7,19-trioxatetracyclo[15.6.1.14,8.020,24]pentacosa-10,14,16,22-tetraene-6,2'-oxane]-2-one

7. Cl-301,423

8. (6r,25s)-5-o-demethyl-28-deoxy-25-((e)-1,3-dimethyl-1-butenyl)-6,28-epoxy-23-oxomilbemycin B 23-(e)-(o-methyloxime)

9. Milbemycin B

10. Moxidectina

11. Moxidectine

12. Moxidectinum

13. Moxidectine [inn-french]

14. Moxidectinum [inn-latin]

15. Unii-ngu5h31yo9

16. Moxidectina [inn-spanish]

17. Moxidectin [usan:inn:ban]

18. Moxidectin (tn)

19. (2ae,2'r,4e,4'e,5's,6r,6's,8e,11r,15s,17ar,20r,20ar,20bs)-6'-[(1e)-1,3-dimethylbut-1-enyl]-20,20b-dihydroxy-4'-(methoxyimino)-5',6,8,19-tetramethyl-3',4',5',6,6',7,10,11,14,15,17a,20,20a,20b-tetradeca

20. Hydrospiro[2h,17h-11,15-methanofuro[4,3,2-pq][2,6]benzodioxacyclooctadecine-13,2'-pyran]-17-one

21. Moxidectin [mi]

22. Moxidectin (usp/inn)

23. Moxidectin [inn]

24. Moxidectin [usan]

25. Moxidectin [mart.]

26. Moxidectin [usp-rs]

27. Moxidectin [who-dd]

28. Moxidectin For Veterinary Use

29. Moxidectin [green Book]

30. Chembl2104415

31. Dtxsid5037577

32. Moxidectin [orange Book]

33. Schembl13112872

34. Chebi:183811

35. Moxidectin [usp Monograph]

36. Advocate Component Moxidectin

37. Hy-b0777

38. Mfcd00866560

39. S3713

40. Akos025401990

41. Zinc253476173

42. Ccg-270317

43. Db11431

44. Moxidectin Component Of Advocate

45. Nsc 760424

46. Moxidectin [ema Epar Veterinary]

47. (2ae,4e,5'r,6r,6's,8e,11r,13s,15s,17ar,20r,20ar,20bs)-6'-((e)-1,3-dimethyl-1-butenyl)-5',6,6',7,10,11,14,15,17a,20,20a,20b-dodecahydro-20,20b-dihydroxy-5',6,8,19-tetramethylspiro(11,15-methano-2h,13h,17h-furo(4,3,2-pq)(2,6)benzodioxacyclooctadecin-13,2'-(2h)pyran)-4',17(3'h)-dione 4'-(e)-(o-methyloxime)

48. Ac-27773

49. As-17881

50. Moxidectin 100 Microg/ml In Acetonitrile

51. Cl-301423

52. M3136

53. D05084

54. Moxidectin, Vetranal(tm), Analytical Standard

55. 507m065

56. Moxidectin For Veterinary Use [ep Monograph]

57. Moxidectin, European Pharmacopoeia (ep) Reference Standard

58. Moxidectin, United States Pharmacopeia (usp) Reference Standard

59. Moxidectin, Pharmaceutical Secondary Standard; Certified Reference Material

60. Moxidectin For System Suitability, European Pharmacopoeia (ep) Reference Standard

61. Milbemycin B, 5-o-demethyl-28-deoxy-25-((1e)-1,3-dimethyl-1-butenyl)-6,28-epoxy-23-(methoxyimino)-, (6r,23e,25s)-

62. Milbemycin B, 5-o-demethyl-28-deoxy-25-(1,3-dimethyl-1-butenyl)-6,28-epoxy-23-(methoxyimino)-, (6r,23e,25s(e))-

63. Milbemycin B, 5-o-demethyl-28-deoxy-25-(1,3-dimethyl-1-butenyl)-6,28-epoxy-23-(methoxyimino)-,(6r,23e,25s(e))-

2.4 Create Date

2006-10-25

3 Chemical and Physical Properties

Molecular Formula	C₃₇H₅₃NO₈
Molecular Weight	639.8 g/mol
XLogP3	4.3
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	9
Rotatable Bond Count	3
Exact Mass	639.37711765 g/mol
Monoisotopic Mass	639.37711765 g/mol
Topological Polar Surface Area	116 Å²
Heavy Atom Count	46
Formal Charge	0
Complexity	1340
Isotope Atom Count	0
Defined Atom Stereocenter Count	10
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	5
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Indication

Moxidectin is indicated for the treatment of river blindness, also called onchocerciasis, in patients aged 12 years and older. River blindness is caused by a parasitic worm _Onchocerca volvulus_ and it is manifested as severe itching, disfiguring skin conditions and visual impairment caused by the worm's larvae. The transmission of _Onchocerca volvulus_ is performed person to person by black flies that breed in fast-flowing rivers in sub-Saharan Africa, Yemen and South and Central America. The larvae released by the adult parasite invade skin and eyes where they can produce the severe disease manifestations.

FDA Label

5 Pharmacology and Biochemistry

5.1 Pharmacology

Moxidectin has been reported to be highly effective against _Onchocerca volvulus_ when compared to ivermectin. When moxidectin was administered in infected individuals, the microfilarial load in the skin was lower even when compared to the current therapy, ivermectin. The levels of microfilarial got reduced to an undetectable level while being safe to be used in mass drug administration.

5.2 MeSH Pharmacological Classification

Anthelmintics

Agents that kill parasitic worms. They are used therapeutically in the treatment of HELMINTHIASIS in man and animal. (See all compounds classified as Anthelmintics.)

Antinematodal Agents

Substances used in the treatment or control of nematode infestations. They are used also in veterinary practice. (See all compounds classified as Antinematodal Agents.)

Insecticides

Pesticides designed to control insects that are harmful to man. The insects may be directly harmful, as those acting as disease vectors, or indirectly harmful, as destroyers of crops, food products, or textile fabrics. (See all compounds classified as Insecticides.)

5.3 ATC Code

P - Antiparasitic products, insecticides and repellents

P02 - Anthelmintics

P02C - Antinematodal agents

P02CX - Other antinematodals

P02CX03 - Moxidectin

5.4 Absorption, Distribution and Excretion

Absorption

The penetration of moxidectin in the parasite is not restricted as this compound is a very poor substrate of p-glycoprotein, which is vital for the reduction of the uptake of lipophilic compounds from the GI tract and for the increase in biliary, intestinal and renal secretion. After oral administration of moxidectin, the plasma maximal concentration of 70.4 mg/kg was reached after 0.37 day with a reported AUC of 363.6 mcg/day/ml. It is also important to mention that oral bioavailability is enhanced with the co-administration with lipids.

Route of Elimination

When moxidectin is orally administered, 2% of the dose is eliminated unchanged in the feces within 72 hours. Renal elimination is negligible.

Volume of Distribution

Moxidectin presents a larger volume of distribution and mean residence time when compared to ivermectin. The reported volume of distribution is of 1.2 l/kg.

Clearance

The apparent clearance of moxidectin is 3.5 L/hour.

5.5 Metabolism/Metabolites

Reports have registered enzymatic modification in humans and in nematodes. In the case of moxidectin, there has been registered C29-30- and C14-mono-hydroxymethyl derivatives mainly by the cytochrome CYP3A and CYP2B. The metabolism of moxidectin is considered to contribute to a small extent to the elimination. Some other metabolites formed are O-demethyl-dihydroxy metabolites. The metabolism of the of moxidectin is not major as the major residue in fat, liver, kidney and muscle is the unchanged moxidectin.

5.6 Biological Half-Life

Moxidectin reporter terminal half-life is 20.2 days.

5.7 Mechanism of Action

Moxidectin selectively binds to the parasite's GABA-A and glutamate-gated chloride ion channels which are vital for the function of invertebrate nerve and muscle cells. It presents activity against the parasite but it does not kill him. Once moxidectin is bound, there is an increased permeability leading to an influx of chloride ions and flaccid paralysis of the parasite.

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