Related CAS #
119568-55-7 (HCl)
104-31-4 (free base);
Synonym
Benzonatate; Tessalon; KM65; KM 65; KM-65; Exangit; Ventussin
IUPAC/Chemical Name
2,5,8,11,14,17,20,23,26-nonaoxaoctacosan-28-yl 4-(butylamino)benzoate
InChi Key
MAFMQEKGGFWBAB-UHFFFAOYSA-N
InChi Code
InChI=1S/C30H53NO11/c1-3-4-9-31-29-7-5-28(6-8-29)30(32)42-27-26-41-25-24-40-23-22-39-21-20-38-19-18-37-17-16-36-15-14-35-13-12-34-11-10-33-2/h5-8,31H,3-4,9-27H2,1-2H3
SMILES Code
O=C(OCCOCCOCCOCCOCCOCCOCCOCCOCCOC)C1=CC=C(NCCCC)C=C1
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:
Benzonatate, also known as Tessalon and KM-65, is a sodium channel protein antagonist.
In vitro activity:
This study used whole cell voltage clamp recording to test the effects of benzonatate on voltage-gated sodium (Na(+)) currents in two murine cell lines, catecholamine A differentiated (CAD) cells, which express primarily Nav1.7, and N1E-115, which express primarily Nav1.3. This study found that, like local anesthetics, benzonatate strongly and reversibly inhibits voltage-gated Na(+) channels.
Reference: Neuropharmacology. 2016 Feb;101:179-87. https://pubmed.ncbi.nlm.nih.gov/26386152/
|
Solvent |
mg/mL |
mM |
| Solubility |
| DMF |
50.0 |
82.82 |
| DMSO |
75.0 |
124.22 |
| Ethanol |
50.0 |
82.82 |
| Ethanol:PBS (pH 7.2) (1:1) |
0.5 |
0.83 |
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
603.75
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:
Evans MS, Maglinger GB, Fletcher AM, Johnson SR. Benzonatate inhibition of voltage-gated sodium currents. Neuropharmacology. 2016 Feb;101:179-87. doi: 10.1016/j.neuropharm.2015.09.020. Epub 2015 Sep 16. PMID: 26386152.
In vitro protocol:
Evans MS, Maglinger GB, Fletcher AM, Johnson SR. Benzonatate inhibition of voltage-gated sodium currents. Neuropharmacology. 2016 Feb;101:179-87. doi: 10.1016/j.neuropharm.2015.09.020. Epub 2015 Sep 16. PMID: 26386152.
1: Evans MS, Maglinger GB, Fletcher AM, Johnson SR. Benzonatate inhibition of voltage-gated sodium currents. Neuropharmacology. 2016 Feb;101:179-87. doi: 10.1016/j.neuropharm.2015.09.020. PubMed PMID: 26386152.
2: McLawhorn MW, Goulding MR, Gill RK, Michele TM. Analysis of benzonatate overdoses among adults and children from 1969-2010 by the United States Food and Drug Administration. Pharmacotherapy. 2013 Jan;33(1):38-43. doi: 10.1002/phar.1153. PubMed PMID: 23307543.
3: Thimann DA, Huang CJ, Goto CS, Feng SY. Benzonatate toxicity in a teenager resulting in coma, seizures, and severe metabolic acidosis. J Pediatr Pharmacol Ther. 2012 Jul;17(3):270-3. doi: 10.5863/1551-6776-17.3.270. PubMed PMID: 23258970; PubMed Central PMCID: PMC3526931.
4: Winter ML, Spiller HA, Griffith JR. Benzonatate Ingestion Reported to the National Poison Center Database System (NPDS). J Med Toxicol. 2010 Dec;6(4):398-402. doi: 10.1007/s13181-010-0086-6. PubMed PMID: 20490746; PubMed Central PMCID: PMC3550467.
5: Cohen V, Jellinek SP, Stansfield L, Truong H, Baseluos C, Marshall JP. Cardiac arrest with residual blindness after overdose of Tessalon® (benzonatate) perles. J Emerg Med. 2011 Aug;41(2):166-71. doi: 10.1016/j.jemermed.2009.08.027. PubMed PMID: 19892505.
6: Hendershot AJ, Colling L, Mauger TF. Corneal anesthetic abuse from the use of topical benzonatate (Tessalon Perle). Cornea. 2011 Dec;30(12):1518-9. doi: 10.1097/ICO.0b013e318207f229. PubMed PMID: 21673569.
7: Yoshioka I, Surmaitis R, Katz KD. A 17-Year-Old Girl With Cough--Pulseless After Drug Overdose. Sodium benzonatate overdose. Pediatr Emerg Care. 2016 Mar;32(3):197-9. doi: 10.1097/PEC.0000000000000733. PubMed PMID: 26928103.
8: Dicpinigaitis PV, Gayle YE, Solomon G, Gilbert RD. Inhibition of cough-reflex sensitivity by benzonatate and guaifenesin in acute viral cough. Respir Med. 2009 Jun;103(6):902-6. doi: 10.1016/j.rmed.2008.12.008. PubMed PMID: 19121573.
9: In brief: benzonatate warning. Med Lett Drugs Ther. 2011 Feb 7;53(1357):9. Review. PubMed PMID: 21304443.
10: Crouch BI, Knick KA, Crouch DJ, Matsumura KS, Rollins DE. Benzonatate overdose associated with seizures and arrhythmias. J Toxicol Clin Toxicol. 1998;36(7):713-8. PubMed PMID: 9865240.
11: Doona M, Walsh D. Benzonatate for opioid-resistant cough in advanced cancer. Palliat Med. 1998 Jan;12(1):55-8. PubMed PMID: 9616460.
12: Danesh M, Murase JE. Use of a nonnarcotic antitussive for severe, treatment-resistant oral ulcers. J Am Acad Dermatol. 2015 Jun;72(6):e159. doi: 10.1016/j.jaad.2015.02.1102. PubMed PMID: 25981022.
13: Cohan JA, Manning TJ, Lukash L, Long C, Ziminski KR, Conradi SE. Two fatalities resulting from Tessalon (benzonatate). Vet Hum Toxicol. 1986 Dec;28(6):543-4. PubMed PMID: 3788039.
14: Thorén P, Oberg B. Studies on the endoanesthetic effects of lidocaine and benzonatate on non-medullated nerve endings in the left ventricle. Acta Physiol Scand. 1981 Jan;111(1):51-8. PubMed PMID: 7223452.
15: NEW AND non-official drugs: benzonatate. J Am Med Assoc. 1959 Aug 15;170(16):1927-8. English, Italian. PubMed PMID: 13672794.
