Synonym
Allegra; Fexofenadine HCl; MDL-16-455A; MDL16455A; MDL 16 455A; Telfast
IUPAC/Chemical Name
2-(4-(1-hydroxy-4-(4-(hydroxydiphenylmethyl)piperidin-1-yl)butyl)phenyl)-2-methylpropanoic acid hydrochloride
InChi Key
RRJFVPUCXDGFJB-UHFFFAOYSA-N
InChi Code
InChI=1S/C32H39NO4.ClH/c1-31(2,30(35)36)25-17-15-24(16-18-25)29(34)14-9-21-33-22-19-28(20-23-33)32(37,26-10-5-3-6-11-26)27-12-7-4-8-13-27;/h3-8,10-13,15-18,28-29,34,37H,9,14,19-23H2,1-2H3,(H,35,36);1H
SMILES Code
O=C(O)C(C)(C)C1=CC=C(C(O)CCCN2CCC(C(C3=CC=CC=C3)(O)C4=CC=CC=C4)CC2)C=C1.[H]Cl
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
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
Biological target:
Fexofenadine hydrochloride (MDL-16455 hydrochloride), a H1R antagonist, is an anti-allergic agent.
In vitro activity:
Fexofenadine significantly inhibited the upregulated expression of IL-8 in HCT116 and COLO205 cells stimulated with TNF-α. Fexofenadine suppressed nuclear factor-κB DNA-binding activity.
Reference: J Pharmacol Exp Ther. 2015 Mar;352(3):455-61. https://pubmed.ncbi.nlm.nih.gov/25538104/
In vivo activity:
This study investigated inhibition of the immune response in palladium allergic mice by administration of prednisolone as a glucocorticoid and fexofenadine hydrochloride as an antihistamine. Compared with glucocorticoids, fexofenadine hydrochloride significantly suppressed the number of T cells by interfering with the development of antigen-presenting cells from the sensitization phase.
Reference: Int J Mol Sci. 2017 Jun 25;18(7):1357. https://pubmed.ncbi.nlm.nih.gov/28672829/
|
Solvent |
mg/mL |
mM |
| Solubility |
| DMSO |
61.5 |
114.25 |
| DMF |
25.0 |
46.46 |
| Ethanol |
59.5 |
110.57 |
| PBS (pH 7.2) |
1.0 |
1.86 |
| Water |
2.0 |
3.72 |
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
538.12
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.
| 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. Liu R, Chen Y, Fu W, Wang S, Cui Y, Zhao X, Lei ZN, Hettinghouse A, Liu J, Wang C, Zhang C, Bi Y, Xiao G, Chen ZS, Liu CJ. Fexofenadine inhibits TNF signaling through targeting to cytosolic phospholipase A2 and is therapeutic against inflammatory arthritis. Ann Rheum Dis. 2019 Nov;78(11):1524-1535. doi: 10.1136/annrheumdis-2019-215543. Epub 2019 Jul 13. PMID: 31302596; PMCID: PMC8157820.
2. Koh SJ, Kim JW, Kim BG, Lee KL, Chun J, Kim JS. Fexofenadine regulates nuclear factor-κB signaling and endoplasmic reticulum stress in intestinal epithelial cells and ameliorates acute and chronic colitis in mice. J Pharmacol Exp Ther. 2015 Mar;352(3):455-61. doi: 10.1124/jpet.114.217844. Epub 2014 Dec 23. PMID: 25538104.
3. Matsubara R, Kumagai K, Shigematsu H, Kitaura K, Nakasone Y, Suzuki S, Hamada Y, Suzuki R. Fexofenadine Suppresses Delayed-Type Hypersensitivity in the Murine Model of Palladium Allergy. Int J Mol Sci. 2017 Jun 25;18(7):1357. doi: 10.3390/ijms18071357. PMID: 28672829; PMCID: PMC5535850.
In vitro protocol:
1. Liu R, Chen Y, Fu W, Wang S, Cui Y, Zhao X, Lei ZN, Hettinghouse A, Liu J, Wang C, Zhang C, Bi Y, Xiao G, Chen ZS, Liu CJ. Fexofenadine inhibits TNF signaling through targeting to cytosolic phospholipase A2 and is therapeutic against inflammatory arthritis. Ann Rheum Dis. 2019 Nov;78(11):1524-1535. doi: 10.1136/annrheumdis-2019-215543. Epub 2019 Jul 13. PMID: 31302596; PMCID: PMC8157820.
2. Koh SJ, Kim JW, Kim BG, Lee KL, Chun J, Kim JS. Fexofenadine regulates nuclear factor-κB signaling and endoplasmic reticulum stress in intestinal epithelial cells and ameliorates acute and chronic colitis in mice. J Pharmacol Exp Ther. 2015 Mar;352(3):455-61. doi: 10.1124/jpet.114.217844. Epub 2014 Dec 23. PMID: 25538104.
In vivo protocol:
1. Liu R, Chen Y, Fu W, Wang S, Cui Y, Zhao X, Lei ZN, Hettinghouse A, Liu J, Wang C, Zhang C, Bi Y, Xiao G, Chen ZS, Liu CJ. Fexofenadine inhibits TNF signaling through targeting to cytosolic phospholipase A2 and is therapeutic against inflammatory arthritis. Ann Rheum Dis. 2019 Nov;78(11):1524-1535. doi: 10.1136/annrheumdis-2019-215543. Epub 2019 Jul 13. PMID: 31302596; PMCID: PMC8157820.
2. Matsubara R, Kumagai K, Shigematsu H, Kitaura K, Nakasone Y, Suzuki S, Hamada Y, Suzuki R. Fexofenadine Suppresses Delayed-Type Hypersensitivity in the Murine Model of Palladium Allergy. Int J Mol Sci. 2017 Jun 25;18(7):1357. doi: 10.3390/ijms18071357. PMID: 28672829; PMCID: PMC5535850.
1: Veronese M, Barzaghi D, Bertoncini A. Antifungal activity of fenticonazole in experimental dermatomycosis and candidiasis. Arzneimittelforschung. 1981;31(12):2137-9. PubMed PMID: 7199314.
2: Balaïsch J. [Evaluation of the time response of a single dose administration of fenticonazole nitrate]. Contracept Fertil Sex. 1996 May;24(5):417-22. French. PubMed PMID: 8704823.
3: Graziani G, Cazzulani P. Irritation and toxicity studies with fenticonazole applied topically to the skin and mucous membranes. Arzneimittelforschung. 1981;31(12):2152-4. PubMed PMID: 7199317.
4: Graziani G, Cazzulani P, Barbadoro E. Toxicological and pharmacological properties of fenticonazole, a new topical antimycotic. Arzneimittelforschung. 1981;31(12):2145-51. PubMed PMID: 7199316.
5: Feng Z, Zou Q, Tan X, Che W, Zhang Z. Determination of fenticonazole enantiomers by LC-ESI-MS/MS and its application to pharmacokinetic studies in female rats. Arzneimittelforschung. 2011;61(10):587-93. doi: 10.1055/s-0031-1300557. PubMed PMID: 22164967.
6: Fernández-Alba J, Valle-Gay A, Dibildox M, Vargas JA, González J, García M, López LH; Fentimex Mexican Study Group. Fenticonazole nitrate for treatment of vulvovaginitis: efficacy, safety, and tolerability of 1-gram ovules, administered as ultra-short 2-day regimen. J Chemother. 2004 Apr;16(2):179-86. PubMed PMID: 15216954.
7: Novelli A, Periti E, Massi GB, Masi R, Mazzei T, Periti P. Systemic absorption of 3H-fenticonazole after vaginal administration of 1 gram in patients. J Chemother. 1991 Feb;3(1):23-7. PubMed PMID: 2019858.
8: Veronese M, Salvaterra M, Barzaghi D. Fenticonazole, a new imidazole derivative with antibacterial and antifungal activity. In vitro study. Arzneimittelforschung. 1981;31(12):2133-7. PubMed PMID: 7199313.
9: Veronese M, Barzaghi D, Bertoncini A, Zadro M. The Salmonella mutagenicity assay on fenticonazole, a new antifungal imidazole derivative. Arzneimittelforschung. 1981;31(12):2140-2. PubMed PMID: 7037010.
10: Cohen J. [Review of the latest treatments of vulvovaginal mycoses: role of fenticonazole nitrate (Lomexin) in their treatment]. Contracept Fertil Sex. 1997 May;25(5):396-403. Review. French. PubMed PMID: 9273113.
11: Veronese M, Barzaghi D, Bertoncini A, Zadro M. Mutagenicity studies on fenticonazole, a new antifungal imidazole derivative. Arzneimittelforschung. 1981;31(12):2142-4. PubMed PMID: 7199315.
12: Muñoz Reyes JR, Villanueva Reynoso C, Ramos CJ, Menéndez Vázquez J, Bailón Uriza R, Vargas AJ. [Efficacy and tolerance of 200 mg of fenticonazole versus 400 mg of miconazole in the intravaginal treatment of mycotic vulvovaginitis]. Ginecol Obstet Mex. 2002 Feb;70:59-65. Spanish. PubMed PMID: 12017948.
13: Cros C, Chevallier T. [In vitro determination of the texture of 3 gynecologic antifungal agents: TX 15338 (Monazole, sertaconazole nitrate) and 2 related products]. Presse Med. 1998 Dec 5;27(38):1955. French. PubMed PMID: 9879318.
