An internal standard for the quantification of ambroxol
Related Products
Unlabeled Version(s)
19377Ambroxol (hydrochloride)
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Ambroxol-d5 (hydrochloride)

Item No. 38335

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
trans-4-[[(2-amino-3,5-dibromophenyl)methyl]amino]-cyclohexanol-d5, monohydrochloride
CAS Number
2741380-71-0
Molecular Formula
C13H13Br2D5N2O • HCl
Formula Weight
419.6
Purity
≥99% deuterated forms (d1-d5)
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMSO: SolubleMethanol: Soluble
SMILES
NC(C(Br)=C1)=C(C=C1Br)CN[C@H](CC2([2H])[2H])CC([2H])([2H])[C@]2([2H])O.Cl
InChi Code
InChI=1S/C13H18Br2N2O.ClH/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;1H/t10-,11-;/i3D2,4D2,11D;
InChi Key
QNVKOSLOVOTXKF-KAHSTHOTSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    500 µg

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    1 mg

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    5 mg

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    Product Description

    Ambroxol-d5 is intended for use as an internal standard for the quantification of ambroxol (Item No. 19377) by GC- or LC-MS. Ambroxol is an expectorant and active metabolite of bromhexine.1 It inhibits the voltage-gated sodium channel Nav1.2 in isolated dorsal root neurons (IC50 = 110 µM for the rat channel).2 Ambroxol decreases short-circuit currents in electrically stimulated isolated canine tracheal epithelial cells when applied submucosally (IC50 = 60 nM).3 It decreases IL-13-induced production of mucin 5AC (MUC5AC) in primary human airway epithelial cells when used at a concentration of 100 µM and inhibits IL-13-induced decreases in the mucociliary transport rate of endogenous particles in the same cells.4 Ambroxol (30, 60, or 120 mg/kg) increases phenol red secretion, a marker of expectorant activity, in mice.5 Formulations containing ambroxol have been used in the treatment of acute or chronic respiratory conditions.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Malerba, M., and Ragnoli, B. Ambroxol in the 21st century: Pharmacological and clinical update. Expert Opin. Drug Metab. Toxicol. 4(8), 1119-1129 (2008).

    2. Weiser, T. Comparison of the effects of four Na+ channel analgesics on TTX-resistant Na+ currents in rat sensory neurons and recombinant Nav1.2 channels. Neurosci. Lett. 395(3), 179-184 (2006).

    3. Tamaoki, J., Chiyotani, A., Yamauchi, F., et al. Ambroxol inhibits Na+ absorption by canine airway epithelial cells in culture. J. Pharm. Pharmacol. 43(12), 841-843 (1991).

    4. Seagrave, J., Albrecht, H.H., Hill, D.B., et al. Effects of guaifenesin, N-acetylcysteine, and ambroxol on MUC5AC and mucociliary transport in primary differentiated human tracheal-bronchial cells. Respir. Res. 13(1), 98 (2012).

    5. Menezes, P.M.N., Brito, M.C., Sousa de Sá, P.G., et al. Analytical and pharmacological validation of the quantification of phenol red in a mouse model: An optimized method to evaluate expectorant drugs. J. Pharmacol. Toxicol. Methods 98, 106586 (2019).