Abstract Antiallergic Drug Interactions Application Side effects Preparation References
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Loratadine

Abstract Antiallergic Drug Interactions Application Side effects Preparation References
Product Name
Loratadine
CAS No.
79794-75-5
Chemical Name
Loratadine
Synonyms
LORATIDINE;CLARITIN;Ethyl 4-(8-chloro-5,6-dihydro-11H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-ylidene)piperidine-1-carboxylate;CLARATYNE;1-Piperidinecarboxylic acid;ethyl 4-(8-chloro-5,6-dihydro-11h-benzo[5,6]cyclohepta[1,2-b]pyridin-11-ylidene)-1-piperidinecarboxylate;Tadine;Lisino;Loranox;Civeran
CBNumber
CB5283770
Molecular Formula
C22H23ClN2O2
Formula Weight
382.88
MOL File
79794-75-5.mol
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Loratadine Property

Melting point:
134-136°C
Boiling point:
531.3±50.0 °C(Predicted)
Density 
1.261±0.06 g/cm3(Predicted)
RTECS 
TM6129200
storage temp. 
2-8°C
solubility 
DMSO: 26 mg/mL, soluble
form 
powder
pka
4.27±0.20(Predicted)
color 
white
Water Solubility 
It is soluble in DMSO (50 mg/ml), ethanol (77 mg/ml at 25°C), water (<1 mg/ml at 25°C), chloroform, and methanol.
Merck 
14,5578
BCS Class
2
Stability:
Stable, but may be heat sensitive - refrigerate. Incompatible with strong oxidizing agents.
InChIKey
JCCNYMKQOSZNPW-UHFFFAOYSA-N
CAS DataBase Reference
79794-75-5(CAS DataBase Reference)
EPA Substance Registry System
1-Piperidinecarboxylic acid, 4-(8-chloro-5,6-dihydro-11H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-ylidene)-, ethyl ester (79794-75-5)
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Safety

Hazard Codes 
Xi
Risk Statements 
36/37/38
Safety Statements 
22-24/25-36-26
RIDADR 
3077
WGK Germany 
2
HS Code 
29333990
Hazardous Substances Data
79794-75-5(Hazardous Substances Data)
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P321Specific treatment (see … on this label).

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P362Take off contaminated clothing and wash before reuse.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
L9664
Product name
Loratadine
Purity
≥98% (HPLC), powder
Packaging
10mg
Price
$115.2
Updated
2024/03/01
Sigma-Aldrich
Product number
BP875
Product name
Loratadine impurity standard
Purity
British Pharmacopoeia (BP) Reference Standard
Packaging
25MG
Price
$229
Updated
2024/03/01
Sigma-Aldrich
Product number
BP874
Product name
Loratadine
Purity
British Pharmacopoeia (BP) Reference Standard
Packaging
100MG
Price
$262
Updated
2024/03/01
Sigma-Aldrich
Product number
1370270
Product name
Loratadine
Purity
United States Pharmacopeia (USP) Reference Standard
Packaging
200mg
Price
$732
Updated
2024/03/01
TCI Chemical
Product number
L0223
Product name
Loratadine
Purity
>98.0%(HPLC)(T)
Packaging
1g
Price
$104
Updated
2024/03/01
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Loratadine Chemical Properties,Usage,Production

Abstract

Loratadine, sold under the brand name Claritin among others.Loratadine(Claritin) is a long-acting, non-sedating antihistamine that is used for the treatment of allergies. Histamine is a chemical that causes many of the signs and symptoms of an allergy. Histamine is released from histamine-storing cells (mast cells) and attaches to other cells that have receptors for histamine on their surfaces. Histamine stimulates the cells to release chemicals that produce effects that we associate with allergy, including welts, itching, and tissue swelling. Loratadine(Claritin) blocks one type of histamine receptor (the H1 receptor) and thus prevents activation of cells with H1 receptors by histamine.

Antiallergic

Loratadine is a common antiallergic medication, which is a second generation long-acting tricyclic antihistamine, rapid onset of action is strong, does not contain hormones, absorbed by the body metabolism with more active desloratadine, inhibiting histamine H1 receptor by competitively inhibit histamine-induced allergic symptoms, with  no obvious anticholinergic and central inhibition. It is used for the relief of clinical symptoms of allergic rhinitis related, such as sneezing, runny nose and nasal itching, eye itching and burning. It is also used to relieve symptoms of chronic urticaria and other allergic skin diseases.

Drug Interactions

Inhibition of hepatic drug-metabolizing enzyme function drugs can slow the metabolism of the product, such as itraconazole, ketoconazole, Daily with 400 mg ketoconazole suit, can make the product and its active metabolite to carboxyethyl loratadine increased plasma concentrations, but it was not observed in the changes of electrocardiogram (ECG). It can also inhibit the metabolism of loratadine when used with macrolides, cimetidine, theophylline and other drugs together.

Application

  • Antihistamines, peripheral nerves are highly selective H1-receptor, the role of strong, long time. For allergic arthritis, allergic rhinitis.
  • National second-class anti-allergy drugs, for the relief of seasonal allergic rhinitis nasal and non-nasal symptoms and relieve chronic urticaria.

Side effects

Common side effects include sleepiness, dry mouth, and headache. Serious side effects are rare and include allergic reactions, seizures, and liver problems. Use during pregnancy appears to be safe but has not been well studied. It is not recommended in children less than two years old. It is in the second-generation antihistamine family of medication.

Preparation

Compound (I) (0.05mo1) was dissolved in toluene (450m1), dropwise addition of ethyl chloroformate (0.15mo1). Canada finished in the sauna heating 2h, and then stirred at room temperature overnight. Added 800ml water. The benzene layer was separated, washed with water, and dried. Decompression concentrated oil, with petroleum ether after impregnation with acetonitrile, recrystallization, the yield of loratadine, 64%.

References

https://en.wikipedia.org/wiki/Loratadine
http://www.medicinenet.com/loratadine/article.htm

Description

Loratadine is a non-sedating antihistamine indicated for use in allergic rhinitis and chronic urticaria. Its major advantage over other non-sedating antihistamines such as astemizole and terfenadine is its very fast onset of action. Loratadine is claimed not to cross the blood-brain barrier.

Chemical Properties

White Crystalline Solid

Originator

Schering Plough (USA)

Uses

antinflammatory, analgesic, antipyretic

Uses

Histamine H1 receptor antagonist; antihistamine.

Uses

A nonsedating-type histamine H1-receptor

Uses

Loratadine, is used as a peripheral histamine H1 receptor agonist. It is also used as an orally active antiallergic agent. It is an important raw material and intermediate used in Organic Synthesis, Pharmaceuticals, Agrochemicals and Dyestuff.

Indications

Loratadine (Claritin) is a long-acting, potent peripheral H1 blocker with minimal sedative effects. It does not appear to have the same adverse cardiac effects as the other nonsedating H1 antihistamines. It is indicated for allergic rhinitis and chronic urticaria.

Definition

ChEBI: Loratadine is a benzocycloheptapyridine that is 6,11-dihydro-5H-benzo[5,6]cyclohepta[1,2-b]pyridine substituted by a chloro group at position 8 and a 1-(ethoxycarbonyl)piperidin-4-ylidene group at position 11. It is a H1-receptor antagonist commonly employed in the treatment of allergic disorders. It has a role as a geroprotector, a H1-receptor antagonist, an anti-allergic agent and a cholinergic antagonist. It is an ethyl ester, a N-acylpiperidine, a tertiary carboxamide, an organochlorine compound and a benzocycloheptapyridine. It is functionally related to a desloratadine.

Manufacturing Process

Preparation of Loratadine
In a two-liter vessel provided with a thermometer, a reflux condenser and nitrogen atmosphere, dry tetrahydrofuran (343 ml) was placed, and cooled between 0 and -5°C. Titanium tetrachloride (28.5 ml, 49.5 g, 0.255 mol) was slowly added with stirring (17 min.), keeping the temperature in the above indicated range, a yellow suspension being formed. After the addition was finished, stirring was continued for 10 min. Then, zinc dust (34.5 g, 0.524 mol) was added with stirring in approximately 15 min. keeping the temperature in the above cited range, and after addition was finished, stirring was continued at this temperature for 20 min., a blue suspension being formed. Then, pyridine (17 ml, 0.21 mol) was added with stirring, keeping the temperature in the above range, and then, a solution of 8-chloro-5,6- dihydrobenzo[5,6]cyclohepta[1,2-b]pyridin-11-one (30.0 g, 0.123 mol) and ethyl 4-oxopiperidine-1-carboxylate (25.2 g, 0.147 mol) in anhydrous tetrahydrofuran (96 ml) was added in about 20 min., with stirring and keeping the temperature in the above cited range. The, thus obtained, dark brown mixture was stirred for 3 h keeping the temperature in the above cited range, then was allowed to heat to room temperature and kept at this temperature for 2 h and then heated to 40°C for 17 h. The tetrahydrofuran was distilled off from the reaction mixture to give a black resin that was dissolved in dichloromethane (300 ml) and acidified by addition of isopropanol/HCl 7.2 N (97 ml). The mixture was stirred for 10 min, and the phases were separated, being the aqueous one extracted with dichloromethane (150 ml). The combined organic phases were washed 6 times with a mixture of water (125 ml) and 35% aqueous HCl (7.5 ml). Then, the organic phase was basified to pH 7.5-8.0 by addition of 30% aqueous NH3. The mixture was stirred for 10 min and the phases were separated, and then washed 3 times with water (250 ml). The organic phase was dried with anhydrous sodium sulfate, filtered and the solvent eliminated in vacuo to give a residue (47.47 g) that was treated with acetonitrile (97 ml). The solid was filtered and crystallized from the same solvent to give pure Loratadine, m.p. 132-133°C (18.8 g, 40% yield).

brand name

Alavert (Wyeth); Claritin (Schering-Plough).

Therapeutic Function

Antihistaminic, Antiallergic

General Description

Loratadine, 4-(8-chloro-5,6-dihydro-11Hbenzo[5,6]-cyclohepta[1,2-b]pyridin-l 1-ylidene-1-carboxylic acid ethyl ester, is a white to off-white powder insoluble in water but very soluble in acetone, alcohols, and chloroform. Loratadine is structurally related to the antihistamines azatadine and cyproheptadine, and to some tricyclic antidepressants. It differs from azatadine, in that a neutral carbamate group has replaced the basic tertiary amino moiety, and a phenyl ring has been substituted with a chlorine atom. Loratadine is a selective peripheral H1-antihistamine with a receptor-binding profile like that of the other members of this series, except that it has more antiserotonergic activity. Thus, it produces no substantial CNS or autonomic side effects or cardiac toxicity.
Loratadine displays potency comparable with that of astemizole and greater than that of terfenadine. Loratadine is indicated for the relief of nasal and nonnasal symptoms of seasonal allergic rhinitis. In the presence of a CYP3A4 inhibitor ketoconazole, loratadine is metabolized to descarboethoxyloratadine predominantly by CYP2D6.

Biological Activity

Peripheral histamine H 1 receptor antagonist (K i = 35 nM); devoid of central effects. Orally active antiallergic agent.

Biochem/physiol Actions

Non-sedating histamine H1-receptor antagonist.

Pharmacokinetics

Good oral absorption, rapid and extensive metabolism in the liver, and excreted by urine and feces. After taking the medicine, the effect is fast, and some patients show the effect within 30 minutes. Tmax is 1.5 ~ 2 h, and the elimination half-life is 8 ~ 14 h. The half-life of the active metabolite decarboxymethylethoxyloratadine (DCL) is 17 ~ 24h. The half-life of the elderly and patients with liver disease may be longer. The binding rate of loratadine to plasma protein was 97% ~ 99%, and DCL was 73% ~ 76%. After 24 hours, about 27% of loratadine was excreted from urine, about 40% was eliminated from urine and 42% was excreted from stool after 10 days. With less milk secretion, it is safe to use drugs during lactation.

Clinical Use

Loratadine is related to the first-generation tricyclic antihistamines and to antidepressants. It is nonsedating, and neither it nor its major metabolite, desloratadine (descarboethoxyloratadine), is associated with the potentially cardiotoxic effects reported for terfenadine and astemizole. On chronic dosing, the AUC (plasma concentration–time curve) for the metabolite is greater than that for the parent drug, and its half-life is longer.

Drug interactions

Potentially hazardous interactions with other drugs
Antibacterials: concentration possibly increased by erythromycin.
Antifungals: concentration of loratadine possibly increased by ketoconazole – avoid concomitant use.
Antivirals: concentration possibly increased by ritonavir.

Metabolism

Loratadine undergoes an extensive first pass metabolism, mainly by CYP3A4 and CYP2D6. The major metabolite-desloratadine is pharmacologically active and responsible for a large part of the clinical effect. Approximately 40% of the dose is excreted in the urine and 42% in the faeces over a 10 day period and mainly in the form of conjugated metabolites. Approximately 27% of the dose is eliminated in the urine during the first 24 hours. Less than 1% of the active substance is excreted unchanged in the active form, as loratadine or desloratadine.

storage

Store at RT

Dosage forms

10 mg daily. Patients with liver or renal impairment should be started on a lower dose.

Loratadine Preparation Products And Raw materials

Raw materials

Preparation Products

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Loratadine Suppliers

Kunming jida pharmaceutical co. LTD
Tel
0871-68356968 13000000000
Fax
86-0871-6835699
Email
jidamd@jida.com.cn
Country
China
ProdList
12
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58
Hubei huizepu Pharmaceutical Technology Co., Ltd
Tel
0185-0185-07139096 18507139096
Fax
QQ:1925957016
Email
18507139096@163.com
Country
China
ProdList
3855
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Guangzhou Dreampharm Biotechnology Co., Ltd.
Tel
17825480238
Fax
QQ 3008233717
Email
3008233717@qq.com
Country
China
ProdList
9844
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12
Hubei Chenxin Pharmaceutical Co., Ltd.
Tel
17362916295 17362916295
Fax
QQ:840947394
Email
w17362916295@163.com
Country
China
ProdList
3029
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58
Chengdu Aupone Pharmaceutical Co.,Ltd.
Tel
18980796919
Email
236656639@qq.com
Country
China
ProdList
30
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58
Watson Biotechnology Co.,Ltd
Tel
027-027-59207879 18140587686
Fax
QQ:1972026995
Email
kf@3600chem.com
Country
China
ProdList
4699
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Anhui Dexinjia Biopharm Co., Ltd
Tel
0531-82375886 13001715031
Email
3517280075@qq.com
Country
China
ProdList
295
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58
Wuhan EnTai Technology Development Co,.Ltd
Tel
86-27-82330560
Fax
86-27-82330547
Email
2536851935@qq.com
Country
China
ProdList
348
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69
J & K SCIENTIFIC LTD.
Tel
010-82848833 400-666-7788
Fax
86-10-82849933
Email
jkinfo@jkchemical.com
Country
China
ProdList
96815
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76
Meryer (Shanghai) Chemical Technology Co., Ltd.
Tel
4006608290; 18621169109
Fax
86-21-61259102
Email
market03@meryer.com
Country
China
ProdList
40241
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View Lastest Price from Loratadine manufacturers

hebei hongtan Biotechnology Co., Ltd
Product
Loratadine 79794-75-5
Price
US $30.00/kg
Min. Order
1kg
Purity
98%
Supply Ability
2000kg
Release date
2024-03-22
Sinoway Industrial co., ltd.
Product
Loratadine 79794-75-5
Price
US $0.00-0.00/Kg/Bag
Min. Order
1Kg/Bag
Purity
0.99
Supply Ability
20 tons
Release date
2023-06-01
Sinoway Industrial co., ltd.
Product
Loratadine 79794-75-5
Price
US $0.00-0.00/Kg/Bag
Min. Order
1Kg/Bag
Purity
0.99
Supply Ability
20 tons
Release date
2023-06-01

79794-75-5, LoratadineRelated Search:


  • LORATADINE
  • LORATADINE-D5
  • LORATIDINE
  • CLARATYNE
  • CLARITIN
  • ethyl 4-(8-chloro-5,6-dihydro-11h-benzo[5,6]cyclohepta[1,2-b]pyridin-11-ylidene)-1-piperidinecarboxylate
  • 4-(8-Chloro-10,11-dihydro-4-aza-5H-dibenzo[a,d]cycloheptene-5-ylidene)piperidine-1-carboxylic acid ethyl ester
  • 4-(8-Chloro-5,6-dihydro-11H-benzo[5,6]cyclohepta[1,2-b]pyridine-11-ylidene)piperidine-1-carboxylic acid ethyl ester
  • Loratadine,4-(8-Chloro-5,6-dihydro-11H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-ylidene-1-piperidinecarboxylic acid ethyl ester, Loratidine
  • anium wilfordii Maxim
  • 4(8-CHLORO-5,6-DIHYDRO-11H-BENZO[5,6]CYCLOHEPTA[1,2-B]PYRIDIN-11-YLIDENE)-1-PIPERIDINECARBOXYLATE
  • 4-(8-CHLORO-5,6-DIHYDRO-11H-BENZO[5,6]CYCLOHEPTA[1,2-B]PYRIDIN-11-YLIDENE)-1-PIPERIDINECARBOXYLIC ACID ETHYL ESTER
  • 4-(8-chloro-5,6-dihydro-11h-benzo[5,6]cyclohepta[1,2-b]pyridin-11-ylidene-1-piperidinecarboxylic acid ethyl ester
  • Claritine
  • Loranox
  • Polaratyne
  • Tadine
  • Loratadine, USP
  • Loratadine (200 mg)
  • ethyl 4-{13-chloro-4-azatricyclo[9.4.0.0^{3,8}]pentadeca-1(15),3,5,7,11,13-hexaen-2-ylidene}piperidine-1-carboxylate
  • Claritin, Sch-29851
  • Loratadine API
  • ethyl 4-(8-chloro-5H-benzo[5,6]cyclohepta[1,2-b]pyridin-11(6H)-ylidene)piperidine-1-carboxylate
  • Loratadine (Desloratadine IMpurity E)
  • Desloratadine EP Impurity C
  • INTERMEDIATE OF LORATADINE
  • Loratadine (Desloratadine EP Impurity E)
  • Loratadine Impurity 1
  • Loratadine, 98%, a highly potent selective H1 receptor antagonist
  • ethyl 4-(8-chloro-5H-benzo
  • 4-(8-CHLORO-5,6-DIHYDRO-11H-BENZO[5,6]CYCLOHEPTAL[1,2-B]PYRIDIN-11-YLIDENE-1-PIPERIDINECARBOXYLIC ACID ETHYL ESTER
  • SCH-29851
  • 4-(8-chloro-5,6-dihydro-11H-benzo-[5,6]cyclohepta[1,2-b]pyridin-11-ylidene)-1-piperidinecarboxylic acid ethyl ester
  • DECARBOETHOXY LORATADINE MM(CRM STANDARD)
  • LORATADINE MM(CRM STANDARD)
  • LORATADINE USP(CRM STANDARD)
  • Loratadine(WithEdmf)
  • Loratadine99%Min
  • Loratadine&Int
  • 1-Piperidinecarboxylic acid
  • Claritin, Sch-29851, 4-(8-Chloro-5,6-dihydro-11H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-ylidene)-1-piperidinecarboxylic Acid, Ethyl Ester
  • 1-Piperidinecarboxylic acid, 4-(8-chloro-5,6-dihydro-11H-benzo5,6cyclohepta1,2-bpyridin-11-ylidene)-, ethyl ester
  • 4-(8-Chloro-5,6-dihydro-benzo[5,6]cyclohepta[1,2-b]pyridin-11-ylidene)-piperidine-1-carboxylic acid ethyl ester
  • Claritin, Sch-29851, 4-(8-Chloro-5,6-dihydro-11H-benzo[5,6]cyclohepta[1,2-β]pyridin-11-ylidene)-1-piperidinecarboxylic Acid, Ethyl Ester
  • [1,2-b]pyridin-11-ylidene)-, ethyl ester
  • 4-(8-chloro-5,6-dihydro-11H-benzo[5,6]cyclohepta
  • Loratidine, 4-(8-Chloro-5,6-dihydro-11H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-ylidene-1-piperidinecarboxylic acid ethyl ester
  • 4-(8-Chloro-5,6-dihydro-11H-benzo[5,6]cyclohepta[l,2-b]pyridin-11-ylidene)-1-piperidinecarboxylic acid ethyl ester
  • Clarityn
  • Lisino
  • Civeran
  • Loratadine&gt
  • Loratadine CRS
  • Loratadine for system suitability CRS
  • Loratadine Powder
  • Ethyl 4-(8-chloro-5,6-dihydro-11H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-ylidene)piperidine-1-carboxylate
  • Loratadine USP/EP/BP
  • Loratadiner