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Loratadine(CAS No. 79794-75-5)

Loratadine C22H23ClN2O2 (cas 79794-75-5) Molecular Structure

79794-75-5 Structure

Identification and Related Records

【Name】
Loratadine
【Iupac name】
ethyl
4-(8-chloro-5,6-dihydrobenzo[1,2]cyclohepta[2,
4-b]pyridin-11-ylidene)piperidine-1-carboxylate
【CAS Registry number】
79794-75-5
【Synonyms】
Sch 29851
Bedix Loratadina
Ethyl 4-(8-chloro-5,6-dihydro-11H-benzo(5,6)cyclohepta(1,2-b)pyridin-11-ylidene)-1-piperidinecarboxylate
Claratyne
Biloina
Histaloran
Lorastine
Alarin
Loratadine (JAN/USAN)
Loratadina [Spanish]
Loradif
Claritin D
Sensibit
Loranox
1-Piperidinecarboxylic acid, 4-(8-chloro-5,6-dihydro-11H-benzo(5,6)cyclohepta(1,2-b)pyridin-11-ylidene)-, ethyl ester
Sohotin
Clarityne
Fristamin
Bonalerg
Aerotina
Claritin
Rhinase
Alerpriv
Lertamine
Allertidin
Loratadine (79794-75-5)
Loratadina
Clarityne-D
Lorantis
Pylor
Lowadina
Lesidas
Loratyne
Tadine
【Molecular Formula】
C22H23ClN2O2 (Products with the same molecular formula)
【Molecular Weight】
382.88322
【Inchi】
InChI=1S/C22H23ClN2O2/c1-2-27-22(26)25-12-9-15(10-13-25)20-19-8-7-18(23)14-17(19)6-5-16-4-3-11-24-21(16)20/h3-4,7-8,11,14H,2,5-6,9-10,12-13H2,1H3
【InChIKey】
JCCNYMKQOSZNPW-UHFFFAOYSA-N
【Canonical SMILES】
CCOC(=O)N1CCC(=C2C3=C(CCC4=C2N=CC=C4)C=C(C=C3)Cl)CC1
【MOL File】
79794-75-5.mol

Chemical and Physical Properties

【Appearance】
White powder
【Density】
1.261 g/cm3
【Melting Point】
134-136 oC
【Boiling Point】
531.3 oCat 760 mmHg
【Flash Point】
275.1oC
【Water】
Insoluble
【Solubilities】
Insoluble
【Color/Form】
white
【Stability】
Stable, but may be heat sensitive - refrigerate. Incompatible with strong oxidizing agents.
【Storage temp】
2-8°C
【Computed Properties】
Molecular Weight:382.88322 [g/mol]
Molecular Formula:C22H23ClN2O2
XLogP3:5.2
H-Bond Donor:0
H-Bond Acceptor:3
Rotatable Bond Count:2
Exact Mass:382.144806
MonoIsotopic Mass:382.144806
Topological Polar Surface Area:42.4
Heavy Atom Count:27
Formal Charge:0
Complexity:569
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
Feature 3D Acceptor Count:2
Feature 3D Ring Count:4
Effective Rotor Count:4.4
Conformer Sampling RMSD:0.8
CID Conformer Count:13

Safety and Handling

【Hazard Codes】
Xi
【Risk Statements】
R36/37/38
【Safety Statements 】
S22;S24/25
【Safety】

Hazard Codes: IrritantXi
Risk Statements?of Loratadine (CAS NO.79794-75-5): 36/37/38?
R36/37/38: Irritating to eyes, respiratory system and skin.
Safety Statements: 22-24/25-36-26?
S22: Do not breathe dust.?
S24/25: Avoid contact with skin and eyes.?
S36: Wear suitable protective clothing.?
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.

【Transport】
25kgs
【Formulations/Preparations】
Claritin 10 mg tablets; Claritin-D 5 mg loratadine in the tablet coating for immediate release and 120 mg pseudoephedrine sulfate, USP equally distributed between the tablet for immediate release and the barrier coated extended release core.
【Exposure Standards and Regulations】
Manufacturers, packers, and distributors of drug and drug products for human use are responsible for complying with the labeling, certification, and usage requirements as prescribed by the Federal Food, Drug, and Cosmetic Act, as amended (secs 201-902, 52 Stat. 1040 et seq., as amended; 21 U.S.C. 321-392).
【Specification】

?Loratadine (CAS NO.79794-75-5) is combined with pseudoephedrine, a decongestant; this makes it somewhat useful for colds as well as allergies, but adds potential side-effects of insomnia, nervousness and anxiety.
In the U.S. and UK, loratadine is the only drug of its class available over the counter (though it is no longer the only second generation antihistamine available in this manner).

【Octanol/Water Partition Coefficient】
Log P= 5.20 at pH 7.4
【Disposal Methods】
SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Use and Manufacturing

【Use and Manufacturing】
Methods of Manufacturing

Prepn: F.J. Villani, US pat. 4,282,233 (1981 to Schering); F.J. Villani et al., Arzneimittel-Forsch. 36, 1311 (1986).
【Usage】

A nonsedating-type histamine H1-receptor

Biomedical Effects and Toxicity

【Biological Activity】
Peripheral histamine H 1 receptor antagonist (K i = 35 nM); devoid of central effects. Orally active antiallergic agent.
【Pharmacological Action】
- Agents that are used to treat allergic reactions. Most of these drugs act by preventing the release of inflammatory mediators or inhibiting the actions of released mediators on their target cells. (From AMA Drug Evaluations Annual, 1994, p475)
- Agents, usually topical, that relieve itching (pruritus).
- A class of non-sedating drugs that bind to but do not activate histamine receptors (DRUG INVERSE AGONISM), thereby blocking the actions of histamine or histamine agonists. These antihistamines represent a heterogenous group of compounds with differing chemical structures, adverse effects, distribution, and metabolism. Compared to the early (first generation) antihistamines, these non-sedating antihistamines have greater receptor specificity, lower penetration of BLOOD-BRAIN BARRIER, and are less likely to cause drowsiness or psychomotor impairment.
【Therapeutic Uses】
Anti-Allergic Agents; Antipruritics; Histamine H1 Antagonists
Antihistamines are indicated in the prophylactic and symptomatic treatment of perennial and seasonal allergic rhinitis, vasomotor rhinitis, and allergic conjunctivitis due to inhalant allergens and foods. /Antihistamines; Included in US product labeling/
Antihistamines are indicated for the symptomatic treatment of pruritus associated with allergic reactions and of mild, uncomplicated allergic skin manifestations of urticaria and angioedema, in dermatographism, and in urticaria associated with transfusions. /Antihistamines; Included in US product labeling/
Antihistamines are also use in the treatment of pruritus associated with pityriasis rosea. /Antihistamines; NOT included in US or Canadian product labeling/
Antihistamines are indicated for the relief of sneezing and rhinorrhea associated with the common cold. However, controlled clinical studies have not demonstrated that antihistamines are significantly more effective than placebo in relieving cold symptoms. Non-sedating (i.e., second generation) antihistamines are unlikely to be useful in the treatment of the common cold symptoms since they do not have clinically significant anticholinergic effects (e.g., drying effects on nasal mucosa). /Antihistamines; Included in US product labeling/
Antihistamines are indicated as adjunctive therapy to epinephrine and other standard measures for anaphylactic reactions after the acute manifestations have been controlled, and to ameliorate the allergic reactions to blood or plasma. /Antihistamines; Included in US product labeling/
... Loratadine /is/ used as adjunctive treatment to asthma medications to reduce symptoms and improve bronchodilation in patients with mild atopic asthma. /NOT included in US or Canadian product labeling/
Claritin tablets are indicated for the relief of nasal and non-nasal symptoms of seasonal allergic rhinitis. /Claritin/
A multicenter, double blind study to compare the efficacy and safety of astemizole and loratadine in the treatment of seasonal allergic rhinitis was conducted in 469 patients /greater than 12 yr/ who received 10 mg of astemizole or loratadine once daily for 3 wk. Response to astemizole treatment was 88% and 80% for loratadine. Overall symptom relief was rated significantly higher for astemizole vs loratadine. Adverse experience reports were comparable in the 2 treatment groups. Both drugs were effective and well tolerated; astemizole demonstrated a consistently greater degree of efficacy compared with loratadine.
For many years, Hl antihistamines have been the primary management option for urticaria. However, undesirable side effects, particularly daytime sedation, have limited the usefulness of these classic antihistamines. A new class of peripherally acting, nonsedating antihistamines (terfenadine, astemizole, loratadine, and cetirizine) has proved to have clinical efficacy comparable with the classic antihistamines. In comparative trials between the various nonsedating agents, no significant difference in efficacy has been noted. All these agents have good safety profiles, although astemizole use has been correlated with incr appetite and weight gain in some patients, and cetirizine has caused slightly incr effects compared with placebo. Although Hl/H2 antihistamine combinations have been proposed as possible treatments for urticaria, studies have produced mixed results. [Monroe EW; J Allergy Clin Immunol 86 (4 Pt 2): 662-5 (1990)]
【Biomedical Effects and Toxicity】
H1 antagonists are eliminated more rapidly by children than by adults and more slowly in those with severe liver disease. /H1 Receptor Antagonists/
The H1 antagonists are well absorbed from the gastrointestinal tract. Following oral administration, peak plasma concentrations are achieved in 2 to 3 hours ... . /H1 Receptor Antagonists/
Approximately 80% of the total dose administered can be found equally distributed between urine and feces in the form of metabolic products after 10 days.
Whole body autoradiographic studies in rats and monkeys, radiolabeled tissue distribution studies in mice and rats, and in vivo radioligand studies in mice have shown that neither loratadine nor its metabolites readily cross the blood-brain barrier. Radioligand binding studies with guinea pig pulmonary and brain H1-receptors indicate that there was preferential binding to peripheral versus central nervous system H1-receptors.
Unlike other currently available antihistamines, second generation antihistamines such as ... loratadine appear to distribute poorly or not appreciably into the CNS at usual dosages.

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