(R)-Chlorpheniramine Maleate Salt

  • CAT Number: R049141
  • CAS Number: 23095-76-3
  • Molecular Formula: C20H23ClN2O4
  • Molecular Weight: 390.864
  • Purity: ≥95%
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Chlorpheniramine(CAS: 23095-76-3) is an antihistamine used to relieve symptoms of allergy, hay fever, and the common cold. These symptoms include rash, watery eyes, itchy eyes/nose/throat/skin, cough, runny nose, and sneezing.This medication works by blocking a certain natural substance (histamine) that your body makes during an allergic reaction. By blocking another natural substance made by your body (acetylcholine), it helps dry up some body fluids to relieve symptoms such as watery eyes and runny nose.Cough-and-cold products have not been shown to be safe or effective in children younger than 6 years. Do not use this product to treat cold symptoms in children younger than 6 years unless specifically directed by the doctor. Some products (such as long-acting tablets/capsules) are not recommended for use in children younger than 12 years. Ask your doctor or pharmacist for more details about using your product safely.These products do not cure or shorten the length of the common cold and may cause serious side effects. To decrease the risk for serious side effects, carefully follow all dosage directions. Do not use this product to make a child sleepy. Do not give other cough-and-cold medication that might contain the same or similar ingredients (see also Drug Interactions section). Ask the doctor or pharmacist about other ways to relieve cough and cold symptoms (such as drinking enough fluids, using a humidifier or saline nose drops/spray).

Catalog Number R049141
CAS Number 23095-76-3

(γR)-γ-(4-Chlorophenyl)-N,N-dimethyl-2-pyridinepropanamine (2Z)-2-Butenedioate; ?2-[p-Chloro-α-[2-(dimethylamino)ethyl]benzyl]pyridine Maleate; (-)-Chlorpheniramine Maleate; L-Chlorpheniramine Maleate;

Molecular Formula


Purity 95%
Storage Store at -20°C
IUPAC Name (Z)-but-2-enedioic acid;(3R)-3-(4-chlorophenyl)-N,N-dimethyl-3-pyridin-2-ylpropan-1-amine
InChI InChI=1S/C16H19ClN2.C4H4O4/c1-19(2)12-10-15(16-5-3-4-11-18-16)13-6-8-14(17)9-7-13;5-3(6)1-2-4(7)8/h3-9,11,15H,10,12H2,1-2H3;1-2H,(H,5,6)(H,7,8)/b;2-1-/t15-;/m1./s1

[1]. J Assoc Physicians India. 2020 Apr;68(4):21-25.<br />
The Effect of Aerosolized Chlorpheniramine Maleate on Exercise Induced Bronchospasm and Gas Exchange in Asthmatics.<br />
Chugh J(1), Yadav YR(2), Kulkarni HS(3), Maheshwari S(4).<br />
Author information: (1)Sr. Consultant, Fortis Hospital, Shalimar Bagh, Delhi. (2)Assistant Professor, Department of Medicine, J.L.N. Medical College, Ajmer, Rajasthan. (3)Resident, Department of Medicine, J.L.N. Medical College, Ajmer, Rajasthan. (4)Sr. Professor, Department of Medicine, J.L.N. Medical College, Ajmer, Rajasthan.<br />
INTRODUCTION: Exercise induced asthma (EIB) is an acute, reversible, usually selflimiting airways obstruction which sets in after exercise in patients with asthma. One popular mechanism of EIA is the increase in histamine and its metabolites in circulation after exercise, which leads to bronchoconstriction via histamine receptors in bronchi. Chlorpheniramine Maleate is potent, less sedative antihistaminic drug, which acts by inhibiting histamine release from mast cells. It is also said to have anticholinergic properties. The aerosol route of administration of a drug has the advantages of a faster onset of action, fewer side effects, and greater protection against EIB with respect to small airways function. This study was conducted to evaluate the effect of Chlorpheniramine Maleate aerosol inhalation on flow volumes and gas exchange. MATERIALS AND METHODS: 25 established patients of stabilized bronchial asthma (18 to 44 years) with history of EIA attending Allergy OPD, Medical OPD or Chest clinic were included in the present study. Patients were studied for 3 days in a week at the same time of day. Baseline spirometry was done to know test parameters, i.e. FEV1, PEFR and FEF50%. Gas exchange study during rest including minute ventilation (VE), oxygen consumption (VO2), Carbon dioxide produced per minute (VCO2), Respiratory quotient (R) was carried out. Patient was asked to perform exercise on bicycle ergometer. During exercise VE, VO2, VCO2 and R were recorded every 30 seconds. FEV1, PEFR and FEF50% were recorded immediately after and 5 min after completion of exercise. On day 2, same procedure was repeated with saline nebulisation before the exercise. On day 3, aerosolized Chlorpheniramine Maleate was used instead of saline for nebulisation. Values obtained were tabulated and analysed. OBSERVATIONS AND RESULTS: After exercise FEV1, PEFR, FEF50% decreased on all three days, but the fall in these parameters was less on Day III (prior nebulisation with Chlorpheniramine maleate) compared to previous days. There was significant increase in FEV1, PEFR and FEF50% (P&lt;0.01, 0.05 and 0.05 respectively) which was seen 30 mins after inhalation of Chlorpheniramine maleate aerosol compared to placebo. Resting and exercise values of Minute Ventilation (VE), oxygen uptake (VO2) carbon dioxide expired, on all the three days were comparable and statistically not significant by the end of exercise. On day 2 and 3, &#39;R&#39; as compared to that of day1 was slightly significant during rest and initial minutes of exercise but became insignificant after that till the end of exercise. CONCLUSION: This study shows that Chlorpheniramine causes bronchodilation during resting period by acting on the circulating or tissue histamine in asthmatics which contributes to an increase in resting bronchomotor tone. As there is incomplete inhibition of EIA by Chlorpheniramine, there may be some other associated mediator release for pathogenesis of EIA.<br />
PMID: 32610841 [Indexed for MEDLINE]<br />
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[2]. Drug Deliv Transl Res. 2019 Dec;9(6):1017-1026. doi: 10.1007/s13346-019-00639-w.<br />
Chlorpheniramine maleate containing chitosan-based nanoparticle-loaded thermosensitive in situ gel for management in allergic rhinitis.<br />
Kumar M(1), Upadhayay P(2), Shankar R(3), Joshi M(4), Bhatt S(5), Malik A(5).<br />
Author information: (1)M M College of Pharmacy, Maharishi Markandeshwar (Deemed to be University), Mullana, Ambala, India. [email protected]. (2)Department of Pharmaceutics, Rajiv Academy for Pharmacy, Mathura, India. (3)Department of Pharmaceutics, SHEAT College of Pharmacy, Varanasi, India. (4)Department of Pharmaceutics, Ashoka Institute of Pharmacy, Varanasi, India. (5)M M College of Pharmacy, Maharishi Markandeshwar (Deemed to be University), Mullana, Ambala, India.<br />
The aim of the present study was to fabricate a thermosensitive gel containing chlorpheniramine maleate (CPM)-loaded nanoparticles following intranasal administration for effective treatment of allergic rhinitis. Chitosan-based nanoparticles were prepared by a precipitation method followed by the addition of developed NPs within the poloxamer 407- and carbopol 934P-based mucoadhesive thermoreversible gel. Developed formulations were evaluated for particle size, PDI, % entrapment efficiency, and % cumulative drug permeation. NP3 formulation was found to be optimized on the basis of minimum particle size (143.9&nbsp;nm), maximum entrapment efficiency (80.10&thinsp;&plusmn;&thinsp;0.414%), and highest drug permeation (90.92&thinsp;&plusmn;&thinsp;0.531%). The optimized formulation NP3 was then formulated into thermoreversible in situ gel. This intensifies the contact between the nasal mucosa and the drug and increases and facilitates the drug absorption which results in increased bioavailability. G4 formulation was selected as the optimized formulation on the basis of gelation ability and mucoadhesive strength. Histology was carried out to examine the damage caused by the optimized G4 formulation. Results revealed no visual signs of tissue damage thus indicated safe nasal delivery of nanoparticulate in situ gel formulation G4. Thus, intranasal CPM NP-loaded in situ gel was found to be a promising formulation for the management of allergic rhinitis.<br />
DOI: 10.1007/s13346-019-00639-w PMID: 31049842 [Indexed for MEDLINE]<br />
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[3]. Spectrochim Acta A Mol Biomol Spectrosc. 2018 Nov 5;204:783-790. doi: 10.1016/j.saa.2018.06.081. Epub 2018 Jun 27.<br />
Investigation of the distributional homogeneity on chlorpheniramine maleate tablets using NIR-CI.<br />
Ma L(1), Zhou L(1), Xu M(1), Huang X(1), Zhang Q(1), Dai S(1), Qiao Y(1), Wu Z(2).<br />
Author information: (1)Beijing University of Chinese Medicine, 100102, China; Key Laboratory of TCM-information Engineering of State Administration of TCM, Beijing 100102, China; Beijing Key Laboratory for Basic and Development Research on Chinese Medicine, Beijing 100102, China. (2)Beijing University of Chinese Medicine, 100102, China; Key Laboratory of TCM-information Engineering of State Administration of TCM, Beijing 100102, China; Beijing Key Laboratory for Basic and Development Research on Chinese Medicine, Beijing 100102, China. Electronic address: [email protected]. Homogeneity is the basic element of pharmaceutical analysis. Distributional Homogeneity Index (DHI) was proposed to assess the distributional homogeneity of commercial chlorpheniramine maleate (CPM) tablets. Furthermore, the divergence value of DHI value from expectation DHI (value = 1) was calculated to obtain the CPM distributional homogeneity. The distribution of commercial CPM tablets from six brands was successfully visualized using near infrared chemical imaging (NIR-CI) coupled with characteristic wavenumber method and binary image. Besides, content homogeneity of CPM was obtained through calculating the proportion of white region in the binary image. The result demonstrated that the distributional homogeneity of brand 4 was to be the best among all the brands, following by brand 2, brand 3, brand 5, brand 6 and brand 1. Furthermore, the sequence of the content uniformity was different from the distributional homogeneity, which demonstrated that content uniformity could not represent the distributional homogeneity. This work was a significant method guideline to assess the distributional homogeneity in pharmaceutical field.<br />
DOI: 10.1016/j.saa.2018.06.081 PMID: 30096731 [Indexed for MEDLINE]<br />
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[4]. Chem Pharm Bull (Tokyo). 2000 Aug;48(8):1205-7. doi: 10.1248/cpb.48.1205.<br />
Evidence for the degradation of maleate moiety in chlorpheniramine maleate solution using a stability-indicating HPLC method.<br />
Yamato S(1), Nakajima M, Kawakami N, Shimada K, Tachikawa E, Ohta S, Zenda H.<br />
Author information: (1)Department of Pharmaceutical Analytical Chemistry, Niigata College of Pharmacy, Japan. [email protected]<br />
The degradation phenomenon of maleate moiety of chlorpheniramine maleate in solution has been demonstrated by means of a peculiar ion-pair HPLC method developed by the authors, which permits the simultaneous determination of chlorpheniramine and maleate. A commercial cough drug containing chlorpheniramine maleate was dissolved in water with m-hydroxybenzoic acid as an internal standard, and then kept for several days at room temperature. It was recognized that the maleate content in the drug solution had gradually decreased, whereas chlorpheniramine content had not decreased. A simple solution of maleic acid was also kept for several days at room temperature, and it was also recognized that the maleate content in the solution preserved at the same concentration as the solution of the commercial cough drug had gradually decreased, and the percent of remaining maleate reached zero. The degraded peaks on HPLC chromatogram were not detected at all by UV detector, and the disappearance of maleate was ascertained by GC-MS. No detectable example of maleate of chlorpheniramine maleate in a commercial cough syrup has suggested that maleate moiety of chlorpheniramine maleate decomposed to carbon dioxide.<br />
DOI: 10.1248/cpb.48.1205 PMID: 10959588 [Indexed for MEDLINE]<br />
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[5]. Ann Allergy Asthma Immunol. 2015 Aug;115(2):150-2. doi: 10.1016/j.anai.2015.05.009.<br />
Allergic reaction to chlorpheniramine maleate.<br />
Demirel F(1), Gulec M(2), Kartal O(2), Yesıllik S(2), Baysan A(2), Musabak U(2), Sener O(2).<br />
Author information: (1)Division of Immunology and Allergic Diseases, Department of Internal Medicine, Gulhane Military Medical Academy and Medical School, Ankara, Turkey. Electronic address: [email protected]. (2)Division of Immunology and Allergic Diseases, Department of Internal Medicine, Gulhane Military Medical Academy and Medical School, Ankara, Turkey.<br />
DOI: 10.1016/j.anai.2015.05.009 PMID: 26250772 [Indexed for MEDLINE]

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