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MedKoo Cat#: 463973 | Name: Ambroxol-d5

Description:

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

Ambroxol-d5 is intended for use as an internal standard for the quantification of ambroxol by GC- or LC-MS. Ambroxol is an expectorant and active metabolite of bromhexine. It decreases short-circuit currents in electrically stimulated isolated canine tracheal epithelial cells when applied submucosally. 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-d5
Ambroxol-d5
CAS#1246818-80-3

Theoretical Analysis

MedKoo Cat#: 463973

Name: Ambroxol-d5

CAS#: 1246818-80-3

Chemical Formula: C13H13D5Br2N2O

Exact Mass: 381.0100

Molecular Weight: 383.14

Elemental Analysis: C, 40.75; H, 6.05; Br, 41.71; N, 7.31; O, 4.18

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Synonym
Ambroxol-d5; Ambroxol d5;
IUPAC/Chemical Name
(1r,4r)-4-((2-amino-3,5-dibromobenzyl)amino)cyclohexan-1,2,2,6,6-d5-1-ol
InChi Key
JBDGDEWWOUBZPM-URUCQLEXSA-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-/i3D2,4D2,11D
SMILES Code
O[C@]1([2H])C([2H])(C[C@@H](NCC2=C(N)C(Br)=CC(Br)=C2)CC1([2H])[2H])[2H]
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

Preparing Stock Solutions

The following data is based on the product molecular weight 383.14 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
1: Bocci G, Bradfute SB, Ye C, Garcia MJ, Parvathareddy J, Reichard W, Surendranathan S, Bansal S, Bologa CG, Perkins DJ, Jonsson CB, Sklar LA, Oprea TI. Virtual and In Vitro Antiviral Screening Revive Therapeutic Drugs for COVID-19. ACS Pharmacol Transl Sci. 2020 Oct 14;3(6):1278-1292. doi: 10.1021/acsptsci.0c00131. PMID: 33330842; PMCID: PMC7571299. 2: Ijitsu S, Hoashi Y, Hori K, Okimoto K, Kai T, Yoshida M, Uchida T. Preparation of novel functional drug particles embedded in a gelling-swelling layer (PEGS) for taste masking and subsequent rapid drug release. Chem Pharm Bull (Tokyo). 2021 Jan 29. doi: 10.1248/cpb.c20-00941. Epub ahead of print. PMID: 33518551. 3: Yu L, Bhattacharya D, Wang Z, Wang M. Topical administration of ambroxol eye drops augments tear secretion in rabbits. Graefes Arch Clin Exp Ophthalmol. 2021 Jan 29. doi: 10.1007/s00417-020-05043-6. Epub ahead of print. PMID: 33512613. 4: Yang CN, Peng WY, Lin LC, Tsai TH. Protein unbound pharmacokinetics of ambroxol in the blood and brains of rats and the interaction of ambroxol with Polygala tenuifolia by multiple microdialysis. J Ethnopharmacol. 2021 Apr 6;269:113764. doi: 10.1016/j.jep.2020.113764. Epub 2020 Dec 28. PMID: 33383115. 5: Walther C, Döring K, Schmidtke M. Comparative in vitro analysis of inhibition of rhinovirus and influenza virus replication by mucoactive secretolytic agents and plant extracts. BMC Complement Med Ther. 2020 Dec 23;20(1):380. doi: 10.1186/s12906-020-03173-2. PMID: 33357221; PMCID: PMC7757078. 6: Jiang X, Zhang J, Kou B, Zhang C, Zhong J, Fang X, Huang X, Zhang X, Xie F, Hu Q, Ge H, Yu A. Corrigendum to "Ambroxol Improves Neuronal Survival and Reduces White Matter Damage through Suppressing Endoplasmic Reticulum Stress in Microglia after Intracerebral Hemorrhage". Biomed Res Int. 2020 Nov 30;2020:7941716. doi: 10.1155/2020/7941716. Erratum for: Biomed Res Int. 2020 Mar 26;2020:8131286. PMID: 33344647; PMCID: PMC7732389. 7: Schneider R, Leven P, Glowka T, Kuzmanov I, Lysson M, Schneiker B, Miesen A, Baqi Y, Spanier C, Grants I, Mazzotta E, Villalobos-Hernandez E, Kalff JC, Müller CE, Christofi FL, Wehner S. A novel P2X2-dependent purinergic mechanism of enteric gliosis in intestinal inflammation. EMBO Mol Med. 2020 Dec 17;13(1):e12724. doi: 10.15252/emmm.202012724. Epub ahead of print. PMID: 33332729; PMCID: PMC7799361. 8: Ciana G, Dardis A, Pavan E, Da Riol RM, Biasizzo J, Ferino D, Zanatta M, Boni A, Antonini L, Crichiutti G, Bembi B. In vitro and in vivo effects of Ambroxol chaperone therapy in two Italian patients affected by neuronopathic Gaucher disease and epilepsy. Mol Genet Metab Rep. 2020 Nov 21;25:100678. doi: 10.1016/j.ymgmr.2020.100678. PMID: 33294373; PMCID: PMC7691604. 9: Mitini-Nkhoma SC, Fernando N, Ishaka GKD, Handunnetti SM, Pathirana SL. Ion Transport Modulators as Antimycobacterial Agents. Tuberc Res Treat. 2020 Nov 20;2020:3767915. doi: 10.1155/2020/3767915. PMID: 33294223; PMCID: PMC7700046. 10: Vaira LA, Hopkins C, Petrocelli M, Lechien JR, Cutrupi S, Salzano G, Chiesa- Estomba CM, Saussez S, De Riu G. Efficacy of corticosteroid therapy in the treatment of long- lasting olfactory disorders in COVID-19 patients. Rhinology. 2020 Dec 8. doi: 10.4193/Rhin20.515. Epub ahead of print. PMID: 33290446. 11: Zimran A, Ruchlemer R, Revel-Vilk S. A patient with Gaucher disease and plasma cell dyscrasia: bidirectional impact. Hematology Am Soc Hematol Educ Program. 2020 Dec 4;2020(1):389-394. doi: 10.1182/hematology.2020000123. PMID: 33275748; PMCID: PMC7727517. 12: Li HY, Zhang CM, Lv YY, Dai WQ, Xu B, Qi XM. Value of chest imaging in the newborn with suspected COVID-19. Eur Rev Med Pharmacol Sci. 2020 Nov;24(22):11971-11976. doi: 10.26355/eurrev_202011_23859. PMID: 33275274. 13: At Thobari J, Satria CD, Ridora Y, Watts E, Handley A, Standish J, Bachtiar NS, Buttery JP, Soenarto Y, Bines JE. Non-antibiotic medication use in an Indonesian community cohort 0-18 months of age. PLoS One. 2020 Nov 18;15(11):e0242410. doi: 10.1371/journal.pone.0242410. PMID: 33206684; PMCID: PMC7673523. 14: Wang Y, Zhang M, Yu Y, Han T, Zhou J, Bi L. Sputum characteristics and airway clearance methods in patients with severe COVID-19. Medicine (Baltimore). 2020 Nov 13;99(46):e23257. doi: 10.1097/MD.0000000000023257. PMID: 33181718; PMCID: PMC7668462. 15: Bouscary A, Quessada C, René F, Spedding M, Turner BJ, Henriques A, Ngo ST, Loeffler JP. Sphingolipids metabolism alteration in the central nervous system: Amyotrophic lateral sclerosis (ALS) and other neurodegenerative diseases. Semin Cell Dev Biol. 2020 Nov 4:S1084-9521(20)30103-8. doi: 10.1016/j.semcdb.2020.10.008. Epub ahead of print. PMID: 33160824. 16: Meng F, Cheng J, Sang P, Wang J. Effects of Bronchoalveolar Lavage with Ambroxol Hydrochloride on Treating Pulmonary Infection in Patients with Cerebral Infarction and on Serum Proinflammatory Cytokines, MDA and SOD. Comput Math Methods Med. 2020 Oct 9;2020:7984565. doi: 10.1155/2020/7984565. PMID: 33133226; PMCID: PMC7568773. 17: Kumar P. Co-aerosolized Pulmonary Surfactant and Ambroxol for COVID-19 ARDS Intervention: What Are We Waiting for? Front Bioeng Biotechnol. 2020 Sep 25;8:577172. doi: 10.3389/fbioe.2020.577172. PMID: 33102461; PMCID: PMC7546362. 18: Okubo Y, Horimukai K, Michihata N, Morita K, Matsui H, Fushimi K, Yasunaga H. Recent Practice Patterns and Variations in Children Hospitalized for Asthma Exacerbation in Japan. Int Arch Allergy Immunol. 2020;181(12):926-933. doi: 10.1159/000507857. Epub 2020 Oct 22. PMID: 33091910. 19: Wang J, Yu W, Wu N, Gitonga EN, Shen H. Efficacy of high-dose ambroxol for paraquat poisoning: A meta-analysis of randomized controlled trials. J Res Med Sci. 2020 Jul 27;25:67. doi: 10.4103/jrms.JRMS_484_19. PMID: 33088304; PMCID: PMC7554424. 20: Liu H, Wang W, Gao X. Comparison of the efficacy of ambroxol hydrochloride and N -acetylcysteine in the treatment of children with bronchopneumonia and their influence on prognosis. Exp Ther Med. 2020 Dec;20(6):130. doi: 10.3892/etm.2020.9260. Epub 2020 Oct 1. PMID: 33082862; PMCID: PMC7557708.