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Abametapir

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Synopsis

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Chemistry

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Also known as: 1762-34-1, 5,5'-dimethyl-2,2'-bipyridine, 5,5'-dimethyl-2,2'-dipyridyl, 6,6'-bi-3-picoline, 5,5'-dimethyl-2,2'-bipyridyl, Xeglyze

Molecular Formula

C₁₂H₁₂N₂

Molecular Weight

184.24 g/mol

InChI Key

PTRATZCAGVBFIQ-UHFFFAOYSA-N

FDA UNII

6UO390AMFB

Abametapir is a novel pediculicidal metalloproteinase inhibitor used to treat infestations of head lice. The life cycle of head lice (Pediculus capitis) is approximately 30 days, seven to twelve of which are spent as eggs laid on hair shafts near the scalp. Topical pediculicides generally lack adequate ovicidal activity, including standard-of-care treatments such as [permethrin], and many require a second administration 7-10 days following the first to kill newly hatched lice that resisted the initial treatment. The necessity for follow-up treatment may lead to challenges with patient adherence, and resistance to agents like permethrin and [pyrethrins]/[piperonyl butoxide] may be significant in some areas. Investigations into novel ovicidal treatments revealed that several metalloproteinase enzymes were critical to the egg hatching and survival of head lice, and these enzymes were therefore identified as a potential therapeutic target. Abemetapir is an inhibitor of these metalloproteinase enzymes, and the first topical pediculicide to take advantage of this novel target. The improved ovicidal activity (90-100% in vitro) of abemetapir allows for a single administration, in contrast to many other topical treatments, and its novel and relatively non-specific mechanism may help to curb the development of resistance to this agent. Abametapir was first approved for use in the United States under the brand name Xeglyze on July 27, 2020.

1 2D Structure

Abametapir

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

5-methyl-2-(5-methylpyridin-2-yl)pyridine

2.1.2 InChI

InChI=1S/C12H12N2/c1-9-3-5-11(13-7-9)12-6-4-10(2)8-14-12/h3-8H,1-2H3

2.1.3 InChI Key

PTRATZCAGVBFIQ-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CC1=CN=C(C=C1)C2=NC=C(C=C2)C

2.2 Other Identifiers

2.2.1 UNII

6UO390AMFB

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 5,5'-dimethyl-2,2'-bipyridyl

2. Dmbp Cpd

2.3.2 Depositor-Supplied Synonyms

1. 1762-34-1

2. 5,5'-dimethyl-2,2'-bipyridine

3. 5,5'-dimethyl-2,2'-dipyridyl

4. 6,6'-bi-3-picoline

5. 5,5'-dimethyl-2,2'-bipyridyl

6. Xeglyze

7. Ha-44

8. 2,2'-bipyridine, 5,5'-dimethyl-

9. 5-methyl-2-(5-methylpyridin-2-yl)pyridine

10. Brn 0123183

11. 6,6'-di-3-picolyl

12. 6,6'-di-3-picoline

13. Ha44

14. 6uo390amfb

15. Chembl2205807

16. 5,5'-dimethyl-2,2'-bipyridinyl

17. Mfcd01740554

18. Abametapir [usan:inn]

19. Unii-6uo390amfb

20. Xeglyze(abametapir)

21. Xeglyze (tn)

22. Abametapir [mi]

23. Abametapir [inn]

24. Abametapir (usan/inn)

25. Abametapir [usan]

26. Abametapir [who-dd]

27. Schembl351152

28. Yssj3184

29. 2,2 -bis-(5-methylpyridyl)

30. Abametapir [orange Book]

31. Dtxsid00170095

32. Chebi:192617

33. Zinc403335

34. Bdbm50401351

35. Lt0042

36. S5752

37. 5,5''-dimethyl-2,2''-bipyridine

38. Akos005257775

39. Cs-w004546

40. Db11932

41. Hy-w004546

42. Sb17220

43. 5,5'-dimethyl-2,2'-dipyridyl, 98%

44. Ds-15219

45. Sy052805

46. Ft-0689891

47. D10687

48. D70523

49. W-108621

50. Q27265547

51. 5,5 Inverted Exclamation Mark -dimethyl-2,2 Inverted Exclamation Mark -bipyridyl

2.4 Create Date

2005-03-27

3 Chemical and Physical Properties

Molecular Formula	C₁₂H₁₂N₂
Molecular Weight	184.24 g/mol
XLogP3	2.2
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	2
Rotatable Bond Count	1
Exact Mass	184.100048391 g/mol
Monoisotopic Mass	184.100048391 g/mol
Topological Polar Surface Area	25.8 Å²
Heavy Atom Count	14
Formal Charge	0
Complexity	161
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Indication

Abametapir is indicated, in the context of an overall lice management program, for the topical treatment of head lice infestation in patients 6 months of age and older.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Abametavir has been shown to inhibit all stages of embryo development in both head and body lice by interfering with enzymes critical to this process. It is relatively unique amongst lice treatments in that it requires only a single application, whereas many current therapies require two applications, due to its exceptional potency and unique mechanism. Its predominant metabolite, abametapir carboxyl, has a prolonged residence time in the body, with an estimated half-life of 71 40 hours or longer in adults - as this metabolite has been shown to inhibit cytochrome P450 enzymes _in vitro_, the use of substrates of CYP3A4, CYP2B6, or CYP1A2 should be avoided for two weeks following the administration of abametapir. Abametapir lotion is formulated with [benzyl alcohol], which has been associated with significant toxicity following unintentional systemic exposure, particularly in neonates and low birth weight infants. Benzyl alcohol-containing formulations should not be administered to patients <6 months of age, and should be administered to pediatric patients cautiously and under direct supervision of an adult to mitigate the risk of unintentional oral ingestion.

5.2 ATC Code

P - Antiparasitic products, insecticides and repellents

P03 - Ectoparasiticides, incl. scabicides, insecticides and repellents

P03A - Ectoparasiticides, incl. scabicides

P03AX - Other ectoparasiticides, incl. scabicides

P03AX07 - Abametapir

5.3 Absorption, Distribution and Excretion

Absorption

In a pharmacokinetic trial with both adult and pediatric patients, the C_max and AUC_0-8h in the adult group were 41 ng/mL and 121 ng.h/mL and the C_max and AUC_0-8h in the pediatric group were 73 ng/mL and 264 ng.h/mL. In general, systemic exposure to abametapir appears to decrease with increasing age. The median T_max of abemetapir is 0.57 - 1.54 hours. Following topical administration, benzyl alcohol was found in detectable quantities in the serum of 7 out of 39 pediatric patients. The C_max of benzyl alcohol in these subjects ranged from 0.52 to 3.57 g/mL. The predominant circulating metabolite of abemetapir (abemtapir carboxylate) is eliminated slowly from the circulation and is therefore found at higher serum concentrations than its parent drug - based on data collected for 72 hours post-administration, the ratios of serum C_max and AUC_0-72h between abametapir and abametapir carboxylate were approximately 30 and 250, respectively.

Route of Elimination

The clearance and excretion of abametapir has not been examined in patients.

Volume of Distribution

Data regarding the volume of distribution of abametapir are not available.

Clearance

The clearance and excretion of abametapir has not been examined in patients.

5.4 Metabolism/Metabolites

The biotransformation of abametapir is extensive and primarily mediated by CYP1A2. It is metabolized first to abametapir hydroxyl and then further to abametapir carboxyl - the latter is cleared slowly from the plasma, resulting in higher systemic concentrations than that of the parent drug. _In vitro_ studies suggest that abametapir carboxyl may act as an inhibitor of CYP3A4, CYP2B6, and CYP1A2, particularly at the relatively high and prolonged concentrations observed following topical administration of abametapir.

5.5 Biological Half-Life

The elimination half-lives of abametapir and its metabolites have not been well-characterized, but the estimated half-life of abametapir carboxyl is 71 40 hours (or longer) in adults.

5.6 Mechanism of Action

There are several metalloproteinases (enzymes requiring metal co-factors to function) involved in the process of louse egg hatching and survival. _In vitro_ studies have demonstrated that metal-chelating agents can inhibit the activity of these proteins, and may therefore be valuable pediculicidal agents. Abametapir is a metalloproteinase inhibitor that targets louse metalloproteinases which are critical to their development and hatching.

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