Naphazoline nitrate | CAS#5144-52-5 | α1-Adrenergic receptor agonist

MedKoo Cat#: 540309 | Name: Naphazoline nitrate

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Description:

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

Naphazoline nitrate is α1-Adrenergic receptor agonist used to treat congestion and ocular pathologies. It also induces autophagy and necrotic cell death in erythroleukemia cells and inhibits erythroid differentiation.

Chemical Structure

Naphazoline nitrate

CAS#5144-52-5

Theoretical Analysis

MedKoo Cat#: 540309

Name: Naphazoline nitrate

CAS#: 5144-52-5

Chemical Formula: C14H15N3O3

Exact Mass: 273.1113

Molecular Weight: 273.29

Elemental Analysis: C, 61.53; H, 5.53; N, 15.38; O, 17.56

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25g	USD 195.00

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Synonym

Benil; Clera; Naphazoline nitrate; Rhinon; Rinazina; Sanorin Spofa

IUPAC/Chemical Name

2-(naphthalen-1-ylmethyl)-4,5-dihydro-1H-imidazole nitrate

InChi Key

ZAHXYMFVNNUHCP-UHFFFAOYSA-N

InChi Code

InChI=1S/C14H14N2.HNO3/c1-2-7-13-11(4-1)5-3-6-12(13)10-14-15-8-9-16-14;2-1(3)4/h1-7H,8-10H2,(H,15,16);(H,2,3,4)

SMILES Code

O[N+]([O-])=O.C1(CC2=C3C=CC=CC3=CC=C2)=NCCN1

Appearance

Solid powder

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

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Product Data

Product Data

Instruction

View handling instruction

Biological target:

Naphazoline (Naphthazoline) nitrate is an α-adrenergic receptor agonist.

In vitro activity:

This study discovered that the α1-adrenergic agonists naphazoline, oxymetazoline and also the α1-adrenergic antagonist benoxathian are able to raise the intracellular Ca2+-content in K562 cells. Furthermore, this study demonstrates that naphazoline treatment induces ROS-formation as well as an increase in Δψm in K562 cells. Reference: Exp Cell Res. 2011 Dec 10;317(20):2969-80. https://pubmed.ncbi.nlm.nih.gov/21851819/

In vivo activity:

An allergic conjunctivitis mouse model was established using histamine or an antigen (ovalbumin), following which mice were treated with 1% olopatadine solution and/or 0.2 mg/ml of naphazoline hydrochloride. The results indicated that olopatadine and naphazoline hydrochloride significantly suppressed conjunctival dye leakage in mice with histamine or antigen‑induced conjunctival vascular hyperpermeability. In addition, treatment with olopatadine and naphazoline hydrochloride was able to reduce the levels of inflammatory factors (TNF‑α, IL‑1β and IL‑6), cytokines (IFN‑γ and IL‑4), IgE, GMCSF, and NGF in antigen‑induced conjunctival vascular hyperpermeability mice. Reference: Mol Med Rep. 2016 Apr;13(4):3319-25. https://pubmed.ncbi.nlm.nih.gov/26936233/

Preparing Stock Solutions

The following data is based on the product molecular weight 273.29 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. Fuchs R, Schraml E, Leitinger G, Letofsky-Papst I, Stelzer I, Haas HS, Schauenstein K, Sadjak A. α1-adrenergic drugs exhibit affinity to a thapsigargin-sensitive binding site and interfere with the intracellular Ca2+ homeostasis in human erythroleukemia cells. Exp Cell Res. 2011 Dec 10;317(20):2969-80. doi: 10.1016/j.yexcr.2011.08.003. Epub 2011 Aug 9. PMID: 21851819. 2. Quan L, He H. Treatment with olopatadine and naphazoline hydrochloride reduces allergic conjunctivitis in mice through alterations in inflammation, NGF and VEGF. Mol Med Rep. 2016 Apr;13(4):3319-25. doi: 10.3892/mmr.2016.4937. Epub 2016 Feb 23. PMID: 26936233. 3. Tanaka Y, Mizutani N, Fujii M, Nabe T, Kohno S. Different mechanisms between thromboxane A2- and leukotriene D4-induced nasal blockage in guinea pigs. Prostaglandins Other Lipid Mediat. 2006 Sep;80(3-4):144-54. doi: 10.1016/j.prostaglandins.2006.06.003. Epub 2006 Jul 25. PMID: 16939879.

In vitro protocol:

In vivo protocol:

1. Quan L, He H. Treatment with olopatadine and naphazoline hydrochloride reduces allergic conjunctivitis in mice through alterations in inflammation, NGF and VEGF. Mol Med Rep. 2016 Apr;13(4):3319-25. doi: 10.3892/mmr.2016.4937. Epub 2016 Feb 23. PMID: 26936233. 2. Tanaka Y, Mizutani N, Fujii M, Nabe T, Kohno S. Different mechanisms between thromboxane A2- and leukotriene D4-induced nasal blockage in guinea pigs. Prostaglandins Other Lipid Mediat. 2006 Sep;80(3-4):144-54. doi: 10.1016/j.prostaglandins.2006.06.003. Epub 2006 Jul 25. PMID: 16939879.

1: Marszałł MP, Sroka WD, Balinowska A, Mieszkowski D, Koba M, Kaliszan R. Ionic liquids as mobile phase additives for feasible assay of naphazoline in pharmaceutical formulation by HPTLC-UV-densitometric method. J Chromatogr Sci. 2013 Jul;51(6):560-5. doi: 10.1093/chromsci/bms168. Epub 2012 Oct 16. PubMed PMID: 23076785. 2: Nagane Y, Utsugisawa K, Suzuki S, Masuda M, Shimizu Y, Utsumi H, Uchiyama S, Suzuki N. Topical naphazoline in the treatment of myasthenic blepharoptosis. Muscle Nerve. 2011 Jul;44(1):41-4. doi: 10.1002/mus.22002. Epub 2011 Apr 12. PubMed PMID: 21491460. 3: Di Lorenzo C, Coppola G, La Salvia V, Pierelli F. Nasal decongestant and chronic headache: a case of naphazoline overuse headache? F1000Res. 2013 Nov 11;2:237. doi: 10.12688/f1000research.2-237.v1. eCollection 2013. PubMed PMID: 25110575; PubMed Central PMCID: PMC4111119. 4: Imani-Nabiyyi A, Sorouraddin MH. Determination of naphazoline hydrochloride in biological and pharmaceutical samples by a quantum dot-assisted chemiluminescence system using response-surface methodology. Luminescence. 2014 Dec;29(8):994-1002. doi: 10.1002/bio.2649. Epub 2014 Apr 14. PubMed PMID: 24733642. 5: 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. 6: Chocholous P, Satínský D, Solich P. Fast simultaneous spectrophotometric determination of naphazoline nitrate and methylparaben by sequential injection chromatography. Talanta. 2006 Sep 15;70(2):408-13. doi: 10.1016/j.talanta.2006.02.065. Epub 2006 Apr 11. PubMed PMID: 18970784. 7: Pemberton JD, MacIntosh PW, Zeglam A, Fay A. Naphazoline as a confounder in the diagnosis of carotid artery dissection. Ophthal Plast Reconstr Surg. 2015 Mar-Apr;31(2):e33-5. doi: 10.1097/IOP.0000000000000059. PubMed PMID: 24807801. 8: Granier M, Dadure C, Bringuier S, Bonnet-Boyer MC, Ryckwaert Y, Loriaux E, Capdevila X. Intranasal lidocaine plus naphazoline nitrate improves surgical conditions and perioperative analgesia in septorhinoplasty surgery. Can J Anaesth. 2009 Feb;56(2):102-8. doi: 10.1007/s12630-008-9020-7. Epub 2009 Jan 7. PubMed PMID: 19247757. 9: Quan L, He H. Treatment with olopatadine and naphazoline hydrochloride reduces allergic conjunctivitis in mice through alterations in inflammation, NGF and VEGF. Mol Med Rep. 2016 Apr;13(4):3319-25. doi: 10.3892/mmr.2016.4937. Epub 2016 Feb 23. PubMed PMID: 26936233. 10: Hoang VD, Hue NT, Tho NH, Nguyen HM. Simultaneous determination of chloramphenicol, dexamethasone and naphazoline in ternary and quaternary mixtures by RP-HPLC, derivative and wavelet transforms of UV ratio spectra. Spectrochim Acta A Mol Biomol Spectrosc. 2015 Mar 15;139:20-7. doi: 10.1016/j.saa.2014.11.101. Epub 2014 Dec 12. PubMed PMID: 25546493. 11: Iranifam M, Sorouraddin MH. Flow injection chemiluminescence determination of naphazoline hydrochloride in pharmaceuticals. Luminescence. 2014 Feb;29(1):48-51. doi: 10.1002/bio.2500. Epub 2013 Mar 6. PubMed PMID: 23463582. 12: Agha-Mir-Salim P, Stange T, Knipping S, Jahnke V, Berghaus A. [Electron microscopic studies of the rabbit nasal mucosa after short-term application of naphzoline nitrate]. Laryngorhinootologie. 2001 Jul;80(7):389-93. German. PubMed PMID: 11488150. 13: Peralta CM, Silva RA, Fernández LP, Masi AN. Online naphazoline quality control by micellar-enhanced spectrofluorimetry. Luminescence. 2011 Nov-Dec;26(6):689-95. doi: 10.1002/bio.1297. Epub 2011 May 2. PubMed PMID: 21538792. 14: Zhu S, Liu Y. Spectroscopic analyses on interaction of Naphazoline hydrochloride with bovine serum albumin. Spectrochim Acta A Mol Biomol Spectrosc. 2012 Dec;98:142-7. doi: 10.1016/j.saa.2012.08.040. Epub 2012 Aug 23. PubMed PMID: 22995546. 15: Perrin S, Montani D, O'Connell C, Günther S, Girerd B, Savale L, Guignabert C, Sitbon O, Simonneau G, Humbert M, Chaumais MC. Nasal decongestant exposure in patients with pulmonary arterial hypertension: a pilot study. Eur Respir J. 2015 Oct;46(4):1211-4. doi: 10.1183/13993003.00051-2015. Epub 2015 Jul 23. PubMed PMID: 26206880. 16: Vitezić D, Rozmanić V, Franulović J, Ahel V, Matesić D. Naphazoline nasal drops intoxication in children. Arh Hig Rada Toksikol. 1994 Mar;45(1):25-9. PubMed PMID: 8067910. 17: Asadpour-Zeynali K, Ghavami R, Esfandiari R, Soheili-Azad P. Simultaneous determination of antazoline and naphazoline by the net analyte signal standard addition method and spectrophotometric technique. J AOAC Int. 2010 Nov-Dec;93(6):1995-2001. PubMed PMID: 21313830. 18: Liguori C, Garaci F, Romigi A, Mercuri NB, Marciani MG, Placidi F. Bilateral thalamic stroke due to nasal ephedrine and naphazoline use. Neurol Sci. 2015 Jul;36(7):1285-6. doi: 10.1007/s10072-014-2030-z. Epub 2014 Dec 20. PubMed PMID: 25527367. 19: Santoni G, Medica A, Gratteri P, Furlanetto S, Pinzauti S. High-performance liquid chromatographic determination of benzalkonium and naphazoline or tetrahydrozoline in nasal and ophthalmic solutions. Farmaco. 1994 Nov;40(11):751-4. PubMed PMID: 7530451. 20: Oliveira Tda C, Freitas JM, Munoz RA, Richter EM. A batch injection analysis system with square-wave voltammetric detection for fast and simultaneous determination of naphazoline and zinc. Talanta. 2016 May 15;152:308-13. doi: 10.1016/j.talanta.2016.02.031. Epub 2016 Feb 15. PubMed PMID: 26992525.