Ambroxol | CAS#18683-91-5 | expectorant

Ambroxol
featured

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

MedKoo CAT#: 584276

CAS#: 18683-91-5

Description: Ambroxol is a metabolite of Bromhexine that stimulates mucociliary action and clears the air passages in the respiratory tract. It is usually administered as the hydrochloride. Ambroxol decreases IL-13-induced production of mucin 5AC (MUC5AC) in primary human airway epithelial cells and inhibits IL-13-induced decreases in the mucociliary transport rate of endogenous particles in the same cells. Ambroxol increases phenol red secretion, a marker of expectorant activity, in mice when administered at doses of 30, 60, or 120 mg/kg. Formulations containing ambroxol have been used in the treatment of acute or chronic respiratory conditions.

Chemical Structure

Ambroxol

CAS# 18683-91-5

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 584276
Name: Ambroxol
CAS#: 18683-91-5
Chemical Formula: C13H18Br2N2O
Exact Mass: 375.98
Molecular Weight: 378.108
Elemental Analysis: C, 41.30; H, 4.80; Br, 42.27; N, 7.41; O, 4.23

Price and Availability

Size	Price	Availability	Quantity
25mg	USD 180
50mg	USD 300
100mg	USD 550
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Synonym: Ambroxol

IUPAC/Chemical Name: Cyclohexanol, 4-(((2-amino-3,5-dibromophenyl)methyl)amino)-, trans- (9CI)

InChi Key: JBDGDEWWOUBZPM-XYPYZODXSA-N

InChi Code: InChI=1S/C13H18Br2N2O/c14-9-5-8(13(16)12(15)6-9)7-17-10-1-3-11(18)4-2-10/h5-6,10-11,17-18H,1-4,7,16H2/t10-,11-

SMILES Code: O[C@H]1CC[C@H](NCC2=CC(Br)=CC(Br)=C2N)CC1

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

More Info:

Product Data:

Product Data

Instruction:

View handling instruction

Biological target:	Ambroxol is a glucocerebrosidase (GCase) chaperone and increases glucocerebrosidase activity.
In vitro activity:	Ambroxol induced a dose-dependent reduction of the activity of the acid sphingomyelinase in Vero-E6 cells (Fig. 1A). Ambroxol did not show toxicity until 50 μM concentration, whereas higher concentrations such as 75 μM started to show some toxicity as evidenced by flow cytometry studies of untreated and ambroxol-treated cells stained with FITC–annexin V (Roche; Fig. 1B). Reference: J Biol Chem. 2021 Jan-Jun; 296: 100701. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8062550/
In vivo activity:	A significant difference was found between the number of recoverable C. pneumoniae between the Ax-treated and untreated groups. The mean numbers of viable C. pneumoniae IFUs in the Ax (Ambroxol)-treated and untreated groups were 3.1 × 104 and 7.3 × 104 IFU/lung, respectively (Figure 1). The mice in the Ax-treated group exhibited less severe symptoms than those in the control group. Reference: Microorganisms. 2021 Apr; 9(4): 880. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8074272/

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. mM
Solubility
	DMSO	138.0	356.49

Preparing Stock Solutions

The following data is based on the product molecular weight 378.11 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. Carpinteiro A, Gripp B, Hoffmann M, Pöhlmann S, Hoertel N, Edwards MJ, Kamler M, Kornhuber J, Becker KA, Gulbins E. Inhibition of acid sphingomyelinase by ambroxol prevents SARS-CoV-2 entry into epithelial cells. J Biol Chem. 2021 Jan-Jun;296:100701. doi: 10.1016/j.jbc.2021.100701. Epub 2021 Apr 23. PMID: 33895135; PMCID: PMC8062550. 2. Kopytova AE, Rychkov GN, Nikolaev MA, Baydakova GV, Cheblokov AA, Senkevich KA, Bogdanova DA, Bolshakova OI, Miliukhina IV, Bezrukikh VA, Salogub GN, Sarantseva SV, Usenko TC, Zakharova EY, Emelyanov AK, Pchelina SN. Ambroxol increases glucocerebrosidase (GCase) activity and restores GCase translocation in primary patient-derived macrophages in Gaucher disease and Parkinsonism. Parkinsonism Relat Disord. 2021 Mar;84:112-121. doi: 10.1016/j.parkreldis.2021.02.003. Epub 2021 Feb 10. PMID: 33609962. 3. Kókai D, Paróczai D, Virok DP, Endrész V, Gáspár R, Csont T, Bozó R, Burián K. Ambroxol Treatment Suppresses the Proliferation of Chlamydia pneumoniae in Murine Lungs. Microorganisms. 2021 Apr 20;9(4):880. doi: 10.3390/microorganisms9040880. PMID: 33924075; PMCID: PMC8074272. 4. Ge H, Zhang C, Yang Y, Chen W, Zhong J, Fang X, Jiang X, Tan L, Zou Y, Hu R, Chen Y, Feng H. Ambroxol Upregulates Glucocerebrosidase Expression to Promote Neural Stem Cells Differentiation Into Neurons Through Wnt/β-Catenin Pathway After Ischemic Stroke. Front Mol Neurosci. 2021 Jan 20;13:596039. doi: 10.3389/fnmol.2020.596039. PMID: 33551744; PMCID: PMC7855720.
In vitro protocol:	1. Carpinteiro A, Gripp B, Hoffmann M, Pöhlmann S, Hoertel N, Edwards MJ, Kamler M, Kornhuber J, Becker KA, Gulbins E. Inhibition of acid sphingomyelinase by ambroxol prevents SARS-CoV-2 entry into epithelial cells. J Biol Chem. 2021 Jan-Jun;296:100701. doi: 10.1016/j.jbc.2021.100701. Epub 2021 Apr 23. PMID: 33895135; PMCID: PMC8062550. 2. Kopytova AE, Rychkov GN, Nikolaev MA, Baydakova GV, Cheblokov AA, Senkevich KA, Bogdanova DA, Bolshakova OI, Miliukhina IV, Bezrukikh VA, Salogub GN, Sarantseva SV, Usenko TC, Zakharova EY, Emelyanov AK, Pchelina SN. Ambroxol increases glucocerebrosidase (GCase) activity and restores GCase translocation in primary patient-derived macrophages in Gaucher disease and Parkinsonism. Parkinsonism Relat Disord. 2021 Mar;84:112-121. doi: 10.1016/j.parkreldis.2021.02.003. Epub 2021 Feb 10. PMID: 33609962.
In vivo protocol:	1. Kókai D, Paróczai D, Virok DP, Endrész V, Gáspár R, Csont T, Bozó R, Burián K. Ambroxol Treatment Suppresses the Proliferation of Chlamydia pneumoniae in Murine Lungs. Microorganisms. 2021 Apr 20;9(4):880. doi: 10.3390/microorganisms9040880. PMID: 33924075; PMCID: PMC8074272. 2. Ge H, Zhang C, Yang Y, Chen W, Zhong J, Fang X, Jiang X, Tan L, Zou Y, Hu R, Chen Y, Feng H. Ambroxol Upregulates Glucocerebrosidase Expression to Promote Neural Stem Cells Differentiation Into Neurons Through Wnt/β-Catenin Pathway After Ischemic Stroke. Front Mol Neurosci. 2021 Jan 20;13:596039. doi: 10.3389/fnmol.2020.596039. PMID: 33551744; PMCID: PMC7855720.

Molarity Calculator

Calculate the mass, volume, or concentration required for a solution.

Mass

Concentration

Volume

M. Wt* g/mol

*When preparing stock solutions always use the batch-specific molecular weight of the product found on the vial label and SDS / CoA (available online).

Reconstitution Calculator

The reconstitution calculator allows you to quickly calculate the volume of a reagent to reconstitute your vial. Simply enter the mass of reagent and the target concentration and the calculator will determine the rest.

Volume (to add to vial)

Mass (in vial)

Desired Reconstitution Concentration

Dilution Calculator

Calculate the dilution required to prepare a stock solution.

Concentration 1

Volume 1

Concentration 2

Volume 2

1: Chenot JF, Weber P, Friede T. Efficacy of Ambroxol lozenges for pharyngitis: a meta-analysis. BMC Fam Pract. 2014 Mar 13;15:45. doi: 10.1186/1471-2296-15-45. PubMed PMID: 24621446; PubMed Central PMCID: PMC3975147.

2: Wu X, Li S, Zhang J, Zhang Y, Han L, Deng Q, Wan X. Meta-analysis of high doses of ambroxol treatment for acute lung injury/acute respiratory distress syndrome based on randomized controlled trials. J Clin Pharmacol. 2014 Nov;54(11):1199-206. doi: 10.1002/jcph.389. Epub 2014 Sep 7. PubMed PMID: 25174313.

3: Cataldi M, Sblendorio V, Leo A, Piazza O. Biofilm-dependent airway infections: a role for ambroxol? Pulm Pharmacol Ther. 2014 Aug;28(2):98-108. doi: 10.1016/j.pupt.2013.11.002. Epub 2013 Nov 16. Review. PubMed PMID: 24252805.

4: Lapenta L, Morano A, Fattouch J, Casciato S, Fanella M, Giallonardo AT, Di Bonaventura C. Ambroxol-induced focal epileptic seizure. Clin Neuropharmacol. 2014 May-Jun;37(3):84-7. doi: 10.1097/WNF.0000000000000031. PubMed PMID: 24824664.

5: Wang S, Huang D, Ma Q, Chen X. Does ambroxol confer a protective effect on the lungs in patients undergoing cardiac surgery or having lung resection? Interact Cardiovasc Thorac Surg. 2014 Jun;18(6):830-4. doi: 10.1093/icvts/ivu061. Epub 2014 Mar 12. Review. PubMed PMID: 24623642.

6: Zimran A, Altarescu G, Elstein D. Pilot study using ambroxol as a pharmacological chaperone in type 1 Gaucher disease. Blood Cells Mol Dis. 2013 Feb;50(2):134-7. doi: 10.1016/j.bcmd.2012.09.006. Epub 2012 Oct 22. PubMed PMID: 23085429.

7: de Mey C, Patel J, Lakha DR, Richter E, Koelsch S. Efficacy and Safety of an Oral Ambroxol Spray in the Treatment of Acute Uncomplicated Sore Throat. Drug Res (Stuttg). 2015 Dec;65(12):658-67. doi: 10.1055/s-0035-1547229. Epub 2015 Mar 17. PubMed PMID: 25782170.

8: Yamaya M, Nishimura H, Nadine LK, Ota C, Kubo H, Nagatomi R. Ambroxol inhibits rhinovirus infection in primary cultures of human tracheal epithelial cells. Arch Pharm Res. 2014 Apr;37(4):520-9. doi: 10.1007/s12272-013-0210-7. Epub 2013 Jul 16. PubMed PMID: 23856970.

9: Varelogianni G, Hussain R, Strid H, Oliynyk I, Roomans GM, Johannesson M. The effect of ambroxol on chloride transport, CFTR and ENaC in cystic fibrosis airway epithelial cells. Cell Biol Int. 2013 Nov;37(11):1149-56. doi: 10.1002/cbin.10146. Epub 2013 Jul 23. PubMed PMID: 23765701.

10: Fischer J, Pschorn U, Vix JM, Peil H, Aicher B, Müller A, de Mey C. Efficacy and tolerability of ambroxol hydrochloride lozenges in sore throat. Randomised, double-blind, placebo-controlled trials regarding the local anaesthetic properties. Arzneimittelforschung. 2002;52(4):256-63. PubMed PMID: 12040968.

11: Kern KU, Weiser T. Topical ambroxol for the treatment of neuropathic pain. An initial clinical observation. Schmerz. 2015 Dec;29 Suppl 3:S89-96. doi: 10.1007/s00482-015-0060-y. PubMed PMID: 26589711; PubMed Central PMCID: PMC4701773.

12: Rene HD, José MS, Isela SN, Claudio CR. Effects of ambroxol on Candida albicans growth and biofilm formation. Mycoses. 2014 Apr;57(4):228-32. doi: 10.1111/myc.12147. Epub 2013 Nov 14. PubMed PMID: 24224742.

13: Gao X, Zhang Y, Lin Y, Li H, Xin Y, Zhang X, Xu Y, Shang X. [Effect of ambroxol on biofilm of Haemophilus influenzae and bactericidal action]. Lin Chung Er Bi Yan Hou Tou Jing Wai Ke Za Zhi. 2014 May;28(10):721-3. Chinese. PubMed PMID: 25129975.

14: Li Q, Yao G, Zhu X. High-dose ambroxol reduces pulmonary complications in patients with acute cervical spinal cord injury after surgery. Neurocrit Care. 2012 Apr;16(2):267-72. doi: 10.1007/s12028-011-9642-4. PubMed PMID: 22006379.

15: Bendikov-Bar I, Maor G, Filocamo M, Horowitz M. Ambroxol as a pharmacological chaperone for mutant glucocerebrosidase. Blood Cells Mol Dis. 2013 Feb;50(2):141-5. doi: 10.1016/j.bcmd.2012.10.007. Epub 2012 Nov 14. PubMed PMID: 23158495; PubMed Central PMCID: PMC3547170.

16: Zhang Y, Fu Y, Yu J, Ai Q, Li J, Peng N, Song S, He Y, Wang Z. Synergy of ambroxol with vancomycin in elimination of catheter-related Staphylococcus epidermidis biofilm in vitro and in vivo. J Infect Chemother. 2015 Nov;21(11):808-15. doi: 10.1016/j.jiac.2015.08.017. Epub 2015 Sep 28. PubMed PMID: 26423688.

17: Zhi QM, Yang LT, Sun HC. Protective effect of ambroxol against paraquat-induced pulmonary fibrosis in rats. Intern Med. 2011;50(18):1879-87. Epub 2011 Sep 15. PubMed PMID: 21921364.

18: Pulcrano G, Panellis D, De Domenico G, Rossano F, Catania MR. Ambroxol influences voriconazole resistance of Candida parapsilosis biofilm. FEMS Yeast Res. 2012 Jun;12(4):430-8. doi: 10.1111/j.1567-1364.2012.00792.x. Epub 2012 Mar 7. PubMed PMID: 22315984.

19: Zhang ZQ, Wu QQ, Huang XM, Lu H. Prevention of respiratory distress syndrome in preterm infants by antenatal ambroxol: a meta-analysis of randomized controlled trials. Am J Perinatol. 2013 Aug;30(7):529-36. doi: 10.1055/s-0032-1329684. Epub 2012 Dec 10. PubMed PMID: 23229957.

20: Marinov B, Jekova N, Andreeva A, Hitrova S. [Antenatal ambroxol administration for prevention of respiratopry distress syndrome in preterm infants: preliminary report]. Akush Ginekol (Sofiia). 2011;50(4):17-22. Bulgarian. PubMed PMID: 22479892.

Your view history

Ambroxol featured