Finished Dosage Form (FDF) import of Prestwick3_001016 obtained from Indian Custom Trade Statistics

Prestwick3_001016

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Farmak Moxonidine

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Also known as: 75438-57-2, Norcynt, Nucynt, 4-chloro-n-(4,5-dihydro-1h-imidazol-2-yl)-6-methoxy-2-methylpyrimidin-5-amine, Cynt, Be 5895

Molecular Formula

C₉H₁₂ClN₅O

Molecular Weight

241.68 g/mol

InChI Key

WPNJAUFVNXKLIM-UHFFFAOYSA-N

FDA UNII

CC6X0L40GW

Moxonidine is a new-generation centrally acting antihypertensive drug approved for the treatment of mild to moderate essential hypertension. It is suggested to be effective in cases where other agents such as thiazides, beta-blockers, ACE inhibitors, and calcium channel blockers are not appropriate or irresponsive. As well, moxonidine has been shown to present blood pressure-independent beneficial effects on insulin resistance syndrome.

1 2D Structure

Moxonidine

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

4-chloro-N-(4,5-dihydro-1H-imidazol-2-yl)-6-methoxy-2-methylpyrimidin-5-amine

2.1.2 InChI

InChI=1S/C9H12ClN5O/c1-5-13-7(10)6(8(14-5)16-2)15-9-11-3-4-12-9/h3-4H2,1-2H3,(H2,11,12,15)

2.1.3 InChI Key

WPNJAUFVNXKLIM-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CC1=NC(=C(C(=N1)Cl)NC2=NCCN2)OC

2.2 Other Identifiers

2.2.1 UNII

CC6X0L40GW

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 4-chloro-n-(4,5-dihydro-1h-imidazol-2-yl)-6-methoxy-2-methyl-5-pyrimidinamine

2. Be 5895

3. Be-5895

4. Cynt

5. Moxon

6. Moxonidin

7. Normatens

8. Physiotens

2.3.2 Depositor-Supplied Synonyms

1. 75438-57-2

2. Norcynt

3. Nucynt

4. 4-chloro-n-(4,5-dihydro-1h-imidazol-2-yl)-6-methoxy-2-methylpyrimidin-5-amine

5. Cynt

6. Be 5895

7. 4-chloro-n-imidazolidin-2-ylidene-6-methoxy-2-methylpyrimidin-5-amine

8. Bdf5895

9. Bdf 5895

10. Lomox

11. Be-5895

12. 4-chloro-n-(4,5-dihydro-1h-imidazol-2-yl)-6-methoxy-2-methyl-5-pyrimidinamine

13. Ly 326869

14. Bdf5896

15. Be5895

16. Cc6x0l40gw

17. Ly326869

18. 5-pyrimidinamine, 4-chloro-n-(4,5-dihydro-1h-imidazol-2-yl)-6-methoxy-2-methyl-

19. Chembl19236

20. Chebi:7009

21. 4-chloro-5-(2-imidazolin-2-ylamino)-6-methoxy-2-methylpyrimidine

22. 75438-57-2 (free Base)

23. Bdf-5896

24. Ncgc00015649-02

25. Normoxocin

26. Ly-326869

27. Cas-75438-57-2

28. 4-chloro-5-(2-imidazolidinyldeneamino)-6-methoxy-2-methylpyrimidine

29. Dsstox_cid_25170

30. Dsstox_rid_80720

31. Dsstox_gsid_45170

32. Moxonidinum [latin]

33. Moxonidina [spanish]

34. Moxonidina

35. Moxonidinum

36. 4-chloro-n-(imidazolidin-2-ylidene)-6-methoxy-2-methylpyrimidin-5-amine

37. Moxonidine Hydrochloride Hydrate

38. Moxonidine [inn]

39. Bdf-5895

40. Unii-cc6x0l40gw

41. Moxonidine [usan:inn:ban]

42. N-(4-chloro-6-methoxy-2-methylpyrimidin-5-yl)imidazolidin-2-imine

43. Sr-01000075981

44. Cynt (tn)

45. Moxonidine [mi]

46. Moxonidine (usan/inn)

47. Prestwick0_001016

48. Prestwick1_001016

49. Prestwick2_001016

50. Prestwick3_001016

51. Lopac-m-1559

52. Moxonidine [usan]

53. Monoxidine [common Misspelling Of Moxonidine]

54. Moxonidine [mart.]

55. Moxonidine [who-dd]

56. Lopac0_000753

57. Schembl49143

58. Bspbio_001171

59. Mls002222183

60. Spbio_003042

61. Bpbio1_001289

62. Dtxsid5045170

63. Moxonidine [ep Monograph]

64. Hms1571k13

65. Hms2098k13

66. Hms2230b15

67. Hms3373o04

68. Hms3655b17

69. Hms3715k13

70. Hms3747a03

71. Moxonidine 1.0 Mg/ml In Methanol

72. Albb-022451

73. Bcp23003

74. Ex-a3409

75. Hy-b0374

76. Zinc1854466

77. Tox21_110190

78. 2-(6-chloro-4-methoxy-2-methylpyrimidin-5-ylamino)-2-imidazoline

79. 4-chloro-6-methoxy-2-methyl-5-(2-imidazolin-2-yl)aminopyrimidine

80. Ac-637

81. Bdbm50050093

82. Mfcd22689455

83. Pdsp1_000177

84. Pdsp2_000176

85. S2066

86. Stl419983

87. Stl450991

88. Akos015895873

89. Akos015997932

90. Tox21_110190_1

91. Af-0062

92. Ccg-204838

93. Db09242

94. Sdccgsbi-0050731.p002

95. Ncgc00015649-01

96. Ncgc00015649-04

97. Ncgc00015649-05

98. Ncgc00015649-08

99. Ncgc00015649-17

100. Ncgc00092355-02

101. Smr000857402

102. Ab00514003

103. Ft-0601601

104. Ft-0657360

105. M2660

106. Sw196502-4

107. C07451

108. D05087

109. Ab00514003-08

110. Ab00514003_10

111. 438m572

112. A838414

113. Q419944

114. Sr-01000075981-7

115. Brd-k77771411-001-04-4

116. (4-chloro-6-methoxy-2-methyl-pyrimidin-5-yl)-imidazolidin-2-ylidene-amine

117. 4-chloro-n-(imidazolin-2-ylidene)-6-methoxy-2-methyl-5-pyrimidinamine

118. 5-pyrimidinamine, 4-chloro-n-2-imidazolidinylidene-6-methoxy-2-methyl-

119. Bdf5895;bdf-5895;bdf 5895;be 5895; Be-5895; Be5895

120. 2-(4-chloro-6-methoxy-2-methyl-pyrimidin-5-ylamino)-4,5-dihydro-3h-imidazol-1-ium

121. 5-pyrimidinamine, 4-chloro-n-(4,5-dihydro-1h-imidazol-2-yl)-6-methoxy-2-methyl- (9ci)

122. (2r,4r)-1-[(2s)-5-[(aminoiminomethyl)amino]-1-oxo-2-[[(1,2,3,4-tetrahydro-3-methyl-8- Quinolinyl)sulfonyl]amino]pentyl]-4-methyl-2-piperidinecarboxylic Acid

123. 1008754-16-2

124. 4-chloro-n-(4,5-dihydro-1h-imidazol-2-yl)-6-methoxy-2-methyl-pyrimidin-5-amine Hydrochloride;moxonidine

2.4 Create Date

2005-03-25

3 Chemical and Physical Properties

Molecular Formula	C₉H₁₂ClN₅O
Molecular Weight	241.68 g/mol
XLogP3	0.6
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	3
Exact Mass	241.0730377 g/mol
Monoisotopic Mass	241.0730377 g/mol
Topological Polar Surface Area	71.4 Å²
Heavy Atom Count	16
Formal Charge	0
Complexity	275
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

For the treatment of mild to moderate essential or primary hypertension. Effective as most first-line antihypertensives when used as monotherapy.

FDA Label

Treatment of hypertension

5 Pharmacology and Biochemistry

5.1 Pharmacology

Antihypertensive agent whose site of action is the Central Nervous System (CNS), specifically involving interactions with I1- imidazoline and alpha-2-adrenergic rececptors within the rostral ventrolateral medulla (RSV).

5.2 MeSH Pharmacological Classification

Antihypertensive Agents

Drugs used in the treatment of acute or chronic vascular HYPERTENSION regardless of pharmacological mechanism. Among the antihypertensive agents are DIURETICS; (especially DIURETICS, THIAZIDE); ADRENERGIC BETA-ANTAGONISTS; ADRENERGIC ALPHA-ANTAGONISTS; ANGIOTENSIN-CONVERTING ENZYME INHIBITORS; CALCIUM CHANNEL BLOCKERS; GANGLIONIC BLOCKERS; and VASODILATOR AGENTS. (See all compounds classified as Antihypertensive Agents.)

5.3 ATC Code

C02AC05

S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355

C - Cardiovascular system

C02 - Antihypertensives

C02A - Antiadrenergic agents, centrally acting

C02AC - Imidazoline receptor agonists

C02AC05 - Moxonidine

5.4 Absorption, Distribution and Excretion

Absorption

90% of an oral dose is absorbed with negligible interference from food intake or first pass metabolism, resulting in a high bioavailability of 88%.

Route of Elimination

Elimination is nearly entirely via the kidneys with a majority (50 -75%) of overall moxonidine being eliminated unchanged through renal excretion. Ultimately, more than 90% of a dose is eliminated by way of the kidneys within the first 24 hours after administration, with only approximately 1% being eliminiated via faeces.

Volume of Distribution

1.80.4L/kg.

Clearance

Administered twice daily due to short half life. However, lower dosage adjustments and close monitoring is necessary in elderly and renal impairment patients due to reduced clearance. In particular, the exposure AUC can increase by about 50% following a single dose and at steady state in elderly patients and moderately impaired renal function with GFR between 30-60 mL/min can cause AUC increases by 85% and decreases in clearence to 52 %.

5.5 Metabolism/Metabolites

Biotransformation is unimportant with 10-20% of moxonidine undergoing oxidation reactions to the primary 4,5-dehydromoxonidine metabolite and a guanidine derivative by opening of the imidazoline ring. The antihypertensive effects of these 4,5-dehydromoxonidine and guanidine metabolites are only 1/10 and 1/100 the effect of moxonidine. Oxidation on either the methyl group (pyrimidine ring) or on the imidazole ring of moxonidine results in the formation of the hydroxylmethyl moxonidine metabolite or the hydroxy moxonidine metabolite. The hydroxy moxonidine metabolite can be further oxidized to the dihydroxy metabolite or it can lose water to form the dehydrogenated moxonidine metabolite, which itself can be further oxidized to form an N-oxide. Aside from these Phase I metabolites, Phase II metabolism of moxonidine is also evident with the presence of a cysteine conjugate metabolite minus chlorine. Nevertheless, the identification of the hydroxy moxonidine metabolite with a high level of dehydrogenated moxonidine metabolite in human urine samples suggests that dehydrogenation from the hydroxy metabolite to the dehydrogenated moxonidine metabolite represents the primary metabolic pathway in humans. The cytochromes P450 responsible for the metabolism of moxonidine in humans have not yet been determined. Ultimately, the parent moxonidine compound was observed to be the most abundant component in different biological matrices of urinary excretion samples, verifying that metabolism only plays a modest role in the clearance of moxonidine in humans.

5.6 Biological Half-Life

Plasma elimination half life is 2.2 - 2.3 hours while renal elimination half life is 2.6-2.8 hours.

5.7 Mechanism of Action

Stimulation of central alpha 2-adrenergic receptors is associated with sympathoadrenal suppression and subsequent reduction of blood pressure. As this class was further explored it was discovered that sympathoadrenal activity can also be suppressed by a second pathway with a newly discovered drug target specific to imidazolines. Specifically, moxonidine binds the imidazoline receptor subtype 1 (I1) and to a lesser extent lpha-2-adrenoreceptors in the RSV causing a reduction of sympathetic activity, reducing systemic vascular resistance and thus arterial blood pressure. Moreover, since alpha-2-adrenergic receptors are considered the primary molecular target that facilitates the most common side effects of sedation and dry mouth that are elicited by most centrally acting antihypertensives, moxonidine differs from these other centrally acting antihypertensives by demonstrating only low affinity for central alpha-2-adrenoceptors compared to the aforementioned I1-imidazoline receptors.

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