751. Apraclonidine

Nomenclature

CAS number: 66711-21-5
2,6-Dichloro-N1-(4,5-dihydro-1H-imidazol-2-yl)-1,4-benzenediamine; 2,6-dichloro-N′-2-imidazolidinylidene-1,4-benzenediamine; 2-[(4-amino-2,6-dichlorophenyl)imino]imidazolidine; p-aminoclonidine; aplonidine; NC-14.
C9H10Cl2N4; mol wt 245.11.
C 44.10%, H 4.11%, Cl 28.93%, N 22.86%.

Description and references

α2-Adrenergic agonist; structural analog of clonidine, q.v. Synthesis: B. Rouot, G. LeClerc, Bull. Soc. Chim. Fr. Pt. 2, 520 (1979). Prepn (not claimed) and use in treatment of intraocular pressure: B. M. York, Jr., US 4517199 (1985 to Alcon). Pharmacology: B. Rouot et al., C. R. Seances Acad. Sci. Ser. D 286, 909 (1978). Receptor binding studies: D. C. U'Prichard, Prog. Clin. Biol. Res. 71, 53 (1981); D. C. Stump, D. E. MacFarlane, J. Lab. Clin. Med. 102, 779 (1983). Clinical pharmacology: D. A. Abrams et al., Arch. Ophthalmol. 105, 1205 (1987). Clinical evaluation in treatment of intraocular pressure: A. L. Robin et al., ibid. 1208; as additive to maximally tolerated medical therapy in glaucoma: A. L. Robin et al., Am. J. Ophthalmol. 120, 423 (1995).

Chemical structure

Properties

Solid, mp >230°.

Derivative

Hydrochloride.

Nomenclature

CAS number: 73218-79-8
ALO-2145; Iopidine (Alcon).
C9H10Cl2N4.HCl; mol wt 281.57.
C 38.39%, H 3.94%, Cl 37.77%, N 19.90%.

Properties

White powder. Sol in methanol; sparingly sol in water, alcohol. Insol in chloroform, ethyl acetate, hexanes.

Derivative

Dihydrochloride.

Nomenclature

CAS number: 73217-88-6
C9H10Cl2N4.2HCl; mol wt 318.03.
C 33.99%, H 3.80%, Cl 44.59%, N 17.62%.

Properties

uv max (ethanol): 254, 304 nm (ε 1800, 2500).

Therapeutic Category

Treatment of post-surgical elevated intraocular pressure.

Keywords

α-Adrenergic Agonist; Antiglaucoma