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Apraclonidine

Synopsis, Chemistry

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Also known as: 66711-21-5, 4-aminoclonidine, Aplonidine, Apraclonidina, Apraclonidinum, P-aminoclonidine

Molecular Formula

C₉H₁₀Cl₂N₄

Molecular Weight

245.11 g/mol

InChI Key

IEJXVRYNEISIKR-UHFFFAOYSA-N

FDA UNII

843CEN85DI

Apraclonidine is a clonidine derivative with selective alpha-2-adrenergic agonistic activity. Upon ocular administration, apraclonidine enhances aqueous humor uveoscleral outflow and decreases aqueous production by vasoconstriction. This may decrease intraocular pressure (IOP).

Apraclonidine is an alpha-Adrenergic Agonist. The mechanism of action of apraclonidine is as an Adrenergic alpha-Agonist.

1 2D Structure

Apraclonidine

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

2,6-dichloro-1-N-(4,5-dihydro-1H-imidazol-2-yl)benzene-1,4-diamine

2.1.2 InChI

InChI=1S/C9H10Cl2N4/c10-6-3-5(12)4-7(11)8(6)15-9-13-1-2-14-9/h3-4H,1-2,12H2,(H2,13,14,15)

2.1.3 InChI Key

IEJXVRYNEISIKR-UHFFFAOYSA-N

2.1.4 Canonical SMILES

C1CN=C(N1)NC2=C(C=C(C=C2Cl)N)Cl

2.2 Other Identifiers

2.2.1 UNII

843CEN85DI

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 2-(4-amino-2,6-dichloro)phenyliminoimidazolidine

2. 4-aminoclonidine

3. Alo 2145

4. Alo-2145

5. Apraclonidine Hydrochloride

6. Iopidine

7. Iopimax

8. P-aminoclonidine

9. Para-aminoclonidine

2.3.2 Depositor-Supplied Synonyms

1. 66711-21-5

2. 4-aminoclonidine

3. Aplonidine

4. Apraclonidina

5. Apraclonidinum

6. P-aminoclonidine

7. Apraclonidinum [inn-latin]

8. Apraclonidina [inn-spanish]

9. 2,6-dichloro-n1-(4,5-dihydro-1h-imidazol-2-yl)benzene-1,4-diamine

10. 2,6-dichloro-1-n-(4,5-dihydro-1h-imidazol-2-yl)benzene-1,4-diamine

11. Apraclonidine (inn)

12. Iopidine (tn)

13. Chembl647

14. 843cen85di

15. Chebi:2788

16. Apraclonidine [inn]

17. Apraclonidine [inn:ban]

18. Apraclonidine; Lopidine; Nc 14; P-aminoclonidine

19. Unii-843cen85di

20. P-amino Clonidine

21. Aminoclonidine, P

22. Starbld0003083

23. Lopac-a-0779

24. Apraclonidine [mi]

25. Lopac0_000033

26. Schembl34127

27. Apraclonidine [vandf]

28. Apraclonidine [who-dd]

29. Gtpl7117

30. Dtxsid1048415

31. Bdbm81926

32. Zinc20231

33. Bdbm50021812

34. Nsc_51763

35. Pdsp1_000790

36. Pdsp2_000778

37. 1,4-benzenediamine, 2,6-dichloro-n'-(4,5-dihydro-1h-imidazol-2-yl)-

38. 2,6-dichloro-n(1)-(4,5-dihydro-1h-imidazol-2-yl)benzene-1,4-diamine

39. Akos025401361

40. Ccg-204129

41. Db00964

42. Sdccgsbi-0050022.p002

43. Smp1_000016

44. Ncgc00015033-01

45. Ncgc00015033-02

46. Ncgc00015033-03

47. Ncgc00015033-04

48. Ncgc00162050-01

49. Ac-12697

50. Hy-12720

51. Cas_66711-21-5

52. Db-054956

53. Cs-0012296

54. Ft-0602879

55. C07668

56. D07461

57. 2-(4-amino-2,6-dichlorophenylimino)imidazolidine

58. 711a215

59. A918277

60. L000686

61. L013394

62. 2-(4-amino-2,6-dichlorophenylamino)-2-imidazoline

63. 2-(4-amino-2,6-dichlorophenylimino) Imidazolidine

64. Q4781812

65. 2,6-dichloro-n-imidazolidin-2-ylidene-benzene-1,4-diamine

66. 1,4-benzenediamine, 2,6-dichloro-n1-(4,5-dihydro-1h-imidazol-2-yl)-

67. 2,6-dichloro-n1-(imidazolidin-2-ylidene)benzene-1,4-diamine

68. P-aminoclonidine2,6-dichloro-n-imidazolidin-2-ylidene-benzene-1,4-diamine

69. 2,6-dichloro-n-imidazolidin-2-ylidene-benzene-1,4-diamine (p-aminoclonidine)

70. 2,6-dichloro-n-imidazolidin-2-ylidene-benzene-1,4-diamine(p-aminoclonidine)

2.4 Create Date

2005-03-25

3 Chemical and Physical Properties

Molecular Formula	C₉H₁₀Cl₂N₄
Molecular Weight	245.11 g/mol
XLogP3	1.3
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	2
Rotatable Bond Count	2
Exact Mass	244.0282517 g/mol
Monoisotopic Mass	244.0282517 g/mol
Topological Polar Surface Area	62.4 Å²
Heavy Atom Count	15
Formal Charge	0
Complexity	247
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 Information

1 of 2
Drug Name	Iopidine
PubMed Health	Apraclonidine (Into the eye)
Drug Classes	Antiglaucoma
Drug Label	IOPIDINE Ophthalmic Solution contains apraclonidine hydrochloride, an alpha adrenergic agonist, in a sterile isotonic solution for topical application to the eye. Apraclonidine hydrochloride is a white to off-white powder and is highly soluble in w...
Active Ingredient	Apraclonidine hydrochloride
Dosage Form	Solution/drops
Route	Ophthalmic
Strength	eq 1% base; eq 0.5% base
Market Status	Prescription
Company	Alcon

2 of 2
Drug Name	Iopidine
PubMed Health	Apraclonidine (Into the eye)
Drug Classes	Antiglaucoma
Drug Label	IOPIDINE Ophthalmic Solution contains apraclonidine hydrochloride, an alpha adrenergic agonist, in a sterile isotonic solution for topical application to the eye. Apraclonidine hydrochloride is a white to off-white powder and is highly soluble in w...
Active Ingredient	Apraclonidine hydrochloride
Dosage Form	Solution/drops
Route	Ophthalmic
Strength	eq 1% base; eq 0.5% base
Market Status	Prescription
Company	Alcon

4.2 Drug Indication

For prevention or reduction of intraoperative and postoperative increases in intraocular pressure (IOP) before and after ocular laser surgery when used prophylactically. Also used as a short-term adjunctive therapy in patients with open-angle glaucoma who are on maximally tolerated medical therapy requiring additional IOP reduction.

FDA Label

5 Pharmacology and Biochemistry

5.1 Pharmacology

Apraclonidine significantly lowers intraocular pressure with minimal effects on cardiovascular and pulmonary parameters. It lowers intraocular pressure by reducing aqueous humor production and increasing uveoscleral outflow.

5.2 MeSH Pharmacological Classification

Adrenergic alpha-2 Receptor Agonists

Compounds that bind to and activate ADRENERGIC ALPHA-2 RECEPTORS. (See all compounds classified as Adrenergic alpha-2 Receptor Agonists.)

5.3 FDA Pharmacological Classification

5.3.1 Active Moiety

APRACLONIDINE

5.3.2 FDA UNII

843CEN85DI

5.3.3 Pharmacological Classes

alpha-Adrenergic Agonist [EPC]; Adrenergic alpha-Agonists [MoA]

5.4 ATC Code

S01EA03

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

S - Sensory organs

S01 - Ophthalmologicals

S01E - Antiglaucoma preparations and miotics

S01EA - Sympathomimetics in glaucoma therapy

S01EA03 - Apraclonidine

5.5 Absorption, Distribution and Excretion

Absorption

Topical use of apraclonidine ophthalmic solution leads to systemic absorption. Studies of apraclonidine (0.5% ophthalmic solution) dosed one drop three times a day in both eyes for 10 days in normal volunteers yielded mean peak and trough concentrations of 0.9 ng/mL and 0.5 ng/mL, respectively.

5.6 Biological Half-Life

8 hours

5.7 Mechanism of Action

Apraclonidine is a relatively selective alpha2 adrenergic receptor agonist that stimulates alpha1 receptors to a lesser extent. It has a peak ocular hypotensive effect occurring at two hours post-dosing. The exact mechanism of action is unknown, but fluorophotometric studies in animals and humans suggest that Apraclonidine has a dual mechanism of action by reducing aqueous humor production through the constriction of afferent ciliary process vessels, and increasing uveoscleral outflow.