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Apraclonidine

Apraclonidine structure

CAS No:
66711-21-5
Formula:
C9H10Cl2N4
Chemical Name:
Apraclonidine
Synonyms:
1,4-Benzenediamine,2,6-dichloro-N1-(4,5-dihydro-1H-imidazol-2-yl)-;2,6-Dichloro-N1-(4,5-dihydro-1H-imidazol-2-yl)-1,4-benzenediamine;p-Aminoclonidine;NC 14;Apraclonidine;Aplonidine;2-(4-Amino-2,6-dichlorophenylamino)-2-imidazoline;Lopidine;2,6-Dichloro-N1-(4,5-dihydro-1H-imidazol-2-yl)benzene-1,4-diamine;2,6-Dichloro-N1-(2-imidazolidinylidene)-1,4-benzenediamine;78693-46-6
Categories:
Active Pharmaceutical Ingredients > Specialty Drugs

Description

ChEBI: An imidazoline compound having a 4-amino-2,6-dichloroanilino group at the 2-position.

Solid

Apraclonidine is an imidazoline that is 2-amino 4,5-dihydro-1H-imidazoline in which one of the exocyclic amino hydrogens has been replaced by a 4-amino-2,6-dichlorophenyl group. It has a role as an alpha-adrenergic agonist, an antiglaucoma drug, an ophthalmology drug, a beta-adrenergic agonist and a diagnostic agent. It is a member of imidazolines, a dichlorobenzene and a member of guanidines. It is a conjugate base of an apraclonidine(1+).|Apraclonidine, also known as iopidine, is a sympathomimetic used in glaucoma therapy. It is an alpha2-adrenergic agonist.|Apraclonidine is an alpha-Adrenergic Agonist. The mechanism of action of apraclonidine is as an Adrenergic alpha-Agonist.|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 Basic Attributes

Molecular Weight：

245.11

Exact Mass：

245.11

UNII：

843CEN85DI

DSSTox ID：

DTXSID1048415

NCI Thesaurus Code：

C61640

ATC Code：

S01EA03|S - Sensory organs

HScode：

2933290090

Characteristics

PSA：

62.4

XLogP3：

1.4

Appearance：

white solid

Density：

1.63g/cm3

Melting Point：

>230 °C

Boiling Point：

395.5ºC at 760mmHg

Flash Point：

193ºC

Water Solubility：

45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: 1.4 mg/mL Solutions may be stored for several days at 4?#x00b0;C

Storage Conditions：

2-8°C

Safety Information

Transport codes：

UN 2811 6.1/PG 1

wgk germany：

hazard class code：

23/24/25

safety instructions：

22-36/37/39-45

Marks：

Precautionary statement(s)：

P261, P264, P270, P271, P280, P301+P310, P302+P352, P304+P340, P311, P312, P321, P322, P330, P361, P363, P403+P233, P405, P501

Hazard Statements：

H301

GHS Classification：

|Danger|H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]|P261, P264, P270, P271, P280, P301+P310, P302+P352, P304+P340, P311, P312, P321, P322, P330, P361, P363, P403+P233, P405, and P501|Aggregated GHS information provided by 38 companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Toxicity

Toxicity Summary：

Accidental or intentional ingestion of oral apraclonidine has been reported to cause apnea, arrhythmias, asthenia, bradycardia, conduction defects, diminished or absent reflexes, dryness of the mouth, hypotension, hypothermia, hypoventilation, irritability, lethargy, miosis, pallor, respiratory depression, sedation or coma, seizure, somnolence, transient hypertension, and vomiting.

Protein Binding：

98.7%

Drug Information

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

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.

MeSH：

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

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.

Biological Half-Life：

8 hours

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.

MeSH Entry Terms：

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

Apraclonidine Use and Manufacturing

Use Classification：

Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients

Computed Properties

Molecular Weight:245.11
XLogP3:1.3
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:2
Exact Mass:244.0282517
Monoisotopic Mass:244.0282517
Topological Polar Surface Area:62.4
Heavy Atom Count:15
Complexity:247
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes