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MedKoo Cat#: 317516 | Name: Chlorpheniramine Maleate
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Chlorpheniramine maleate is a histamine H1 antagonist used in allergic reactions, hay fever, rhinitis, urticaria, and asthma. One of the most widely used of the classical antihistaminics, it generally causes less drowsiness and sedation than Promethazine. Although not generally approved as an antidepressant or anti-anxiety medication, chlorphenamine appears to have these properties as well. In addition to being an histamine H1 receptor antagonist, chlorphenamine has been shown to work as a serotonin-norepinephrine reuptake inhibitor or SNRI.

Chemical Structure

Chlorpheniramine Maleate
Chlorpheniramine Maleate
CAS#113-92-8 (maleate)

Theoretical Analysis

MedKoo Cat#: 317516

Name: Chlorpheniramine Maleate

CAS#: 113-92-8 (maleate)

Chemical Formula: C20H23ClN2O4

Exact Mass: 0.0000

Molecular Weight: 390.86

Elemental Analysis: C, 61.46; H, 5.93; Cl, 9.07; N, 7.17; O, 16.37

Price and Availability

Size Price Availability Quantity
5g USD 250.00 2 Weeks
10g USD 400.00 2 Weeks
25g USD 650.00 2 Weeks
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Related CAS #
113-92-8 (maleate) 132-22-9 (free)
Synonym
Chlorphenamine maleate; (±)-Chlorpheniramine maleate salt; Chlorpheniramine Maleate; Piriton; Chlortrimeton; Deconamine; Neorestamin; Bayer Brand of Chlorpheniramine Maleate; Chlo-Amine; Chlor-100; Chlor-Trimeton; NCI-C55265; NCIC55265; NCI C55265;
IUPAC/Chemical Name
3-(4-chlorophenyl)-N,N-dimethyl-3-(pyridin-2-yl)propan-1-amine maleate
InChi Key
DBAKFASWICGISY-BTJKTKAUSA-N
InChi Code
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-
SMILES Code
CN(CCC(C1=CC=CC=N1)C2=CC=C(Cl)C=C2)C.O=C(O)/C=C\C(O)=O
Appearance
White crystalline solid.
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO, not in water
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Chlorpheniramine maleate is an histamine H1 receptor antagonist with IC50 of 12 nM.
In vitro activity:
The current study demonstrated that histamine inhibits CREB phosphorylation in HNEpC, which results in decreased AQP5 expression via activation of NF-κB pathway. Chlorpheniramine attenuates the inhibitory effect of histamine in p-CREB/AQP5 expression via suppression of NF-κB signal cascades. Reference: Int J Med Sci. 2017; 14(12): 1268–1275. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5666561/
In vivo activity:
After chlorpheniramine and bupivacaine were subcutaneously injected under the dorsal skin of the rats, the cutaneous analgesia effect was quantitatively evaluated by scoring the number to which the animal failed to react (cutaneous trunci muscle reflex). This study revealed that subcutaneous chlorpheniramine, as well as the local anesthetic bupivacaine elicited cutaneous analgesia in a dosage-dependent manner. Based on their ED50s (50% effective doses), the relative potency was found to be chlorpheniramine [1.13 (1.05-1.22) μmol] < bupivacaine [0.52 (0.46-0.58) μmol] (p < 0.01). When comparing the ED25s, ED50s and ED75s, full recovery time induced by chlorpheniramine was longer (p < 0.01) than that induced by bupivacaine. Reference: Pharmacol Rep. 2020 Aug;72(4):827-832. https://pubmed.ncbi.nlm.nih.gov/32048250/
Solvent mg/mL mM comments
Solubility
DMF 15.0 38.38
Ethanol 41.0 104.90
PBS (pH 7.2) 5.0 12.79
Water 55.7 142.43
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 390.86 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Chang YL, Lin CS, Wang HW, Jian KR, Liu SC. Chlorpheniramine attenuates histamine-mediated aquaporin 5 downregulation in human nasal epithelial cells via suppression of NF-κB activation. Int J Med Sci. 2017 Sep 30;14(12):1268-1275. doi: 10.7150/ijms.21573. PMID: 29104484; PMCID: PMC5666561. 2. Chiu CC, Liu KS, Chen YW, Hung CH, Wang JJ. Chlorpheniramine produces cutaneous analgesia in rats. Pharmacol Rep. 2020 Aug;72(4):827-832. doi: 10.1007/s43440-019-00028-7. Epub 2019 Dec 20. PMID: 32048250. 3. Márquez-Valadez B, Aquino-Miranda G, Quintero-Romero MO, Papacostas-Quintanilla H, Bueno-Nava A, López-Rubalcava C, Díaz NF, Arias-Montaño JA, Molina-Hernández A. The Systemic Administration of the Histamine H1 Receptor Antagonist/Inverse Agonist Chlorpheniramine to Pregnant Rats Impairs the Development of Nigro-Striatal Dopaminergic Neurons. Front Neurosci. 2019 Apr 16;13:360. doi: 10.3389/fnins.2019.00360. PMID: 31040765; PMCID: PMC6476962.
In vitro protocol:
1. Chang YL, Lin CS, Wang HW, Jian KR, Liu SC. Chlorpheniramine attenuates histamine-mediated aquaporin 5 downregulation in human nasal epithelial cells via suppression of NF-κB activation. Int J Med Sci. 2017 Sep 30;14(12):1268-1275. doi: 10.7150/ijms.21573. PMID: 29104484; PMCID: PMC5666561.
In vivo protocol:
1. Chiu CC, Liu KS, Chen YW, Hung CH, Wang JJ. Chlorpheniramine produces cutaneous analgesia in rats. Pharmacol Rep. 2020 Aug;72(4):827-832. doi: 10.1007/s43440-019-00028-7. Epub 2019 Dec 20. PMID: 32048250. 2. Márquez-Valadez B, Aquino-Miranda G, Quintero-Romero MO, Papacostas-Quintanilla H, Bueno-Nava A, López-Rubalcava C, Díaz NF, Arias-Montaño JA, Molina-Hernández A. The Systemic Administration of the Histamine H1 Receptor Antagonist/Inverse Agonist Chlorpheniramine to Pregnant Rats Impairs the Development of Nigro-Striatal Dopaminergic Neurons. Front Neurosci. 2019 Apr 16;13:360. doi: 10.3389/fnins.2019.00360. PMID: 31040765; PMCID: PMC6476962.
1: Demirel F, Gulec M, Kartal O, Yesıllik S, Baysan A, Musabak U, Sener O. Allergic reaction to chlorpheniramine maleate. Ann Allergy Asthma Immunol. 2015 Aug;115(2):150-2. doi: 10.1016/j.anai.2015.05.009. PubMed PMID: 26250772. 2: Ranganathan AT, Chandran CR, Prabhakar P, Lakshmiganthan M, Parthasaradhi T. Plasma cell gingivitis: treatment with chlorpheniramine maleate. Int J Periodontics Restorative Dent. 2015 May-Jun;35(3):411-3. doi: 10.11607/prd.2111. PubMed PMID: 25909529. 3: Zhang F. Physicochemical properties and mechanisms of drug release from melt-extruded granules consisting of chlorpheniramine maleate and Eudragit FS. Drug Dev Ind Pharm. 2015 Jun 24:1-9. [Epub ahead of print] PubMed PMID: 26065535. 4: Zhou LW, Wu ZS, Shi XY, Xu MF, Zhang Q, Qiao YJ. [Research on NIR-CI parameters optimization of chlorpheniramine maleate tablets based on binary image and statistical measurement]. Guang Pu Xue Yu Guang Pu Fen Xi. 2014 Oct;34(10):2821-6. Chinese. PubMed PMID: 25739232. 5: Lou H, Liu M, Qu W, Hu Z, Brunson E, Johnson J, Almoazen H. Evaluation of Chlorpheniramine Maleate microparticles in orally disintegrating film and orally disintegrating tablet for pediatrics. Drug Dev Ind Pharm. 2014 Jul;40(7):910-8. doi: 10.3109/03639045.2013.789907. Epub 2013 Apr 26. PubMed PMID: 23621768. 6: Jelvehgari M, Barghi L, Barghi F. Preparation of Chlorpheniramine Maleate-loaded Alginate/Chitosan Particulate Systems by the Ionic Gelation Method for Taste Masking. Jundishapur J Nat Pharm Prod. 2014 Feb;9(1):39-48. Epub 2014 Feb 20. PubMed PMID: 24644438; PubMed Central PMCID: PMC3957142. 7: Peng C, Lv M, Tian J, Huang Y, Tian Y, Zhang Z. Herb-drug pharmacokinetic interaction of artificial calculus bovis with diclofenac sodium and chlorpheniramine maleate in rats. J Pharm Pharmacol. 2013 Jul;65(7):1064-72. doi: 10.1111/jphp.12069. Epub 2013 Apr 24. PubMed PMID: 23738734. 8: Ali NW, Hegazy MA, Abdelkawy M, Abdelfatah RM. Report: Simultaneous determination of naphazoline hydrochloride, chlorpheniramine maleate and methylene blue in their ternary mixture. Pak J Pharm Sci. 2013 May;26(3):641-8. PubMed PMID: 23625443. 9: Yewale CP, Rathi MN, Kore GG, Jadhav GV, Wagh MP. Formulation and development of taste masked fast-disintegrating tablets (FDTs) of Chlorpheniramine maleate using ion-exchange resins. Pharm Dev Technol. 2013 Mar-Apr;18(2):367-76. doi: 10.3109/10837450.2011.627870. Epub 2011 Oct 24. PubMed PMID: 22023351. 10: Kumar A, Sharma R, Nair A, Saini G. Development and validation of RP-HPLC method for simultaneous estimation of nimesulide, phenylephrine hydrochloride, chlorpheniramine maleate and caffeine anhydrous in pharmaceutical dosage form. Acta Pol Pharm. 2012 Nov-Dec;69(6):1017-22. PubMed PMID: 23285660. 11: Krishnaprasad K, Manshani P, Karankumar J. Health outcome and safety assessment of a fixed dose combination of Amantadine, Paracetamol, Chlorpheniramine maleate, and Phenylephrine introduction in India: A prescription event monitoring study. Perspect Clin Res. 2012 Apr;3(2):62-5. doi: 10.4103/2229-3485.96447. PubMed PMID: 22701822; PubMed Central PMCID: PMC3371550. 12: Misumi N, Hiraike M, Nawata F, Hashimoto M, Tanigawa K, Takase I, Nabeshima A, Honda S. [Protective effects of d-chlorpheniramine maleate pre-treatment against acute side effects of Irinotecan(CPT- 11)]. Gan To Kagaku Ryoho. 2011 Jul;38(7):1149-53. Japanese. PubMed PMID: 21772100. 13: Kim MH, Lee SM, Lee SH, Kwon HS, Kim SH, Cho SH, Min KU, Kim YY, Chang YS. A case of chlorpheniramine maleate-induced hypersensitivity with aspirin intolerance. Allergy Asthma Immunol Res. 2011 Jan;3(1):62-4. doi: 10.4168/aair.2011.3.1.62. Epub 2010 Jul 29. PubMed PMID: 21217928; PubMed Central PMCID: PMC3005322. 14: Al Lawati HA, Suliman FE, Al Kindy SM, Al-Lawati AM, Varma GB, Nour IE. Enhancement of on chip chemiluminescence signal intensity of tris(1,10-phenanthroline)-ruthenium(II) peroxydisulphate system for analysis of chlorpheniramine maleate in pharmaceutical formulations. Talanta. 2010 Oct 15;82(5):1999-2002. doi: 10.1016/j.talanta.2010.08.018. Epub 2010 Aug 24. PubMed PMID: 20875608. 15: Soliman II, Soliman NA, Abdou EM. Formulation and stability study of chlorpheniramine maleate nasal gel. Pharm Dev Technol. 2010 Sep-Oct;15(5):484-91. doi: 10.3109/10837450903286545. PubMed PMID: 20735301. 16: Yin SF, Qiu ZY. [Simultaneous determination of ibuprofen and pseudoephedrin hydrochloride and chlorpheniramine maleate in the compound buluoweimanamin tablets by HPLC]. Nan Fang Yi Ke Da Xue Xue Bao. 2010 Jul;30(7):1703-4. Chinese. PubMed PMID: 20650805. 17: Valderrama P, Romero AL, Imamura PM, Magalhães IR, Bonato PS, Poppi RJ. Quantification of chlorpheniramine maleate enantiomers by ultraviolet spectroscopy and chemometric methods. Anal Bioanal Chem. 2010 May;397(1):181-8. doi: 10.1007/s00216-010-3472-7. Epub 2010 Feb 11. PubMed PMID: 20148242. 18: Al-Rimawi F. Normal-phase LC method for simultaneous analysis of pseudophedrine hydrochloride, dextromethorphan hydrobromide, chlorpheniramine maleate, and paracetamol in tablet formulations. Saudi Pharm J. 2010 Apr;18(2):103-6. doi: 10.1016/j.jsps.2010.02.006. Epub 2010 Feb 13. PubMed PMID: 23960726; PubMed Central PMCID: PMC3730987. 19: Samadi-Maybodi A, Hassani Nejad-Darzi SK. Simultaneous determination of paracetamol, phenylephrine hydrochloride and chlorpheniramine maleate in pharmaceutical preparations using multivariate calibration 1. Spectrochim Acta A Mol Biomol Spectrosc. 2010 Apr;75(4):1270-4. doi: 10.1016/j.saa.2009.12.048. Epub 2009 Dec 22. PubMed PMID: 20097597. 20: Palabiyik IM, Onur F. Multivariate optimization and validation of a capillary electrophoresis method for the simultaneous determination of dextromethorphan hydrobromur, phenylephrine hydrochloride, paracetamol and chlorpheniramine maleate in a pharmaceutical preparation using response surface methodology. Anal Sci. 2010;26(8):853-9. PubMed PMID: 20702938.