Details of the Drug

General Information of Drug (ID: DM9U4FO)

Drug Name
Benzonatate
Synonyms
Benzonatato; Benzonatatum; Benzononantin; Benzononatine; Exangit; Tesalon; Tessalin; Tessalon; Ventussin; Tessalon Perles; KM65; Benzonatato [INN-Spanish]; Benzonatatum [INN-Latin]; Tessalon Capsules (TN); Tessalon Perles (TN); Tessalon perles (TN); Tessalon-ciba; Ventussin-loz; Benzonatate (USP/INN); Benzonatate [USAN:INN:BAN];Nonaethyleneglycol monomethyl ether p-n-butylaminobenzoate; P-butylaminobenzoic acid omega-O-methylnonaethyleneglycol ester; Polyethyleneglycol-p-n-butylaminobenzoate methyl ester; P-(n)-Butylaminobenzoesaeure-(nonaaethylenglykol-monomethylaether)-ester; P-(n)-Butylaminobenzoesaeure-(nonaaethylenglykol-monomethylaether)-ester [German]; Benzoic acid, 4-(butylamino)-, 2,5,8,11,14,17,20,23,26-nonaoxaoctacos-28-yl ester; Benzoic acid, 4-(butylamino)-, 3,6,9,12,15,18,21,24,27-nonaoxaoctacos-1-yl ester; Benzoic acid, 4-(butylamino)-, 3,6,9,12,15,18,21,24,27-nonaoxaoctacos-1-yl ester (9CI); Benzoic acid, p-(butylamino)-, 2-(2-(2-(2-(2-(2-(2-(2-(2-methoxyethoxy)ethoxy)ethoxy)ethoxy)ethoxy)ethoxy)ethoxy)ethoxy)ethyl ester; 2,5,8,11,14,17,20,23,26-Nonaoxaoctacosan-28-yl p-(butylamino)benzoate; 2,5,8,11,14,17,20,23,26-nonaoxaoctacosan-28-yl 4-(butylamino)benzoate; 2-[2-[2-[2-[2-[2-[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethyl 4-(butylamino)benzoate; 2-[2-[2-[2-[2-[2-[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethyl 4-butylaminobenzoate; 3,6,9,12,15,18,21,24,27-Nonaoxaoctacos-1-yl 4-(butylamino)benzoate; 3,6,9,12,15,18,21,24,27-nonaoxaoctacosyl 4-butylaminobenzoate; 4-(butylamino)benzoic acid 3,6,9,12,15,18,21,24,27-nonaoxaoctacos-1-yl ester
Indication
Disease Entry ICD 11 Status REF
Cough MD12 Approved [1], [2]
Therapeutic Class
Antitussives
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 3 Molecular Weight (mw) 603.7
Topological Polar Surface Area (xlogp) 2.4
Rotatable Bond Count (rotbonds) 33
Hydrogen Bond Donor Count (hbonddonor) 1
Hydrogen Bond Acceptor Count (hbondacc) 12
ADMET Property
Absorption Cmax
The maximum plasma concentration (Cmax) of drug is 1063 +/- 460 mcg/L [3]
BDDCS Class
Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 2: low solubility and high permeability [4]
Half-life
The concentration or amount of drug in body reduced by one-half in 100 mg in hours [5]
Metabolism
The drug is metabolized via plasma butyrylcholinesterase (BChE) [6]
MRTD
The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 14.19682 micromolar/kg/day [7]
Chemical Identifiers
Formula
C30H53NO11
IUPAC Name
2-[2-[2-[2-[2-[2-[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethyl 4-(butylamino)benzoate
Canonical SMILES
CCCCNC1=CC=C(C=C1)C(=O)OCCOCCOCCOCCOCCOCCOCCOCCOCCOC
InChI
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
InChIKey
MAFMQEKGGFWBAB-UHFFFAOYSA-N
Cross-matching ID
PubChem CID
7699
ChEBI ID
CHEBI:3032
CAS Number
104-31-4
DrugBank ID
DB00868
TTD ID
D0Q2ES
ACDINA ID
D00062

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Voltage-gated sodium channel alpha Nav1.5 (SCN5A) TTZOVE0 SCN5A_HUMAN Blocker [8]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Drug Inactive Ingredient(s) (DIG) and Formulation(s) of This Drug

DIG
DIG Name DIG ID PubChem CID Functional Classification
Allura red AC dye E00338 33258 Colorant
D&C red no. 28 E00491 6097185 Colorant
FD&C blue no. 1 E00263 19700 Colorant
methylparaben E00149 7456 Antimicrobial preservative
Propyl 4-hydroxybenzoate E00141 7175 Antimicrobial preservative
Propylparaben sodium E00567 23679044 Antimicrobial preservative
Quinoline yellow WS E00309 24671 Colorant
Sodium methylparaben E00543 23663626 Antimicrobial preservative
Sunset yellow FCF E00255 17730 Colorant
Ammonia E00007 222 Alkalizing agent
Carmellose sodium E00625 Not Available Disintegrant
Glycerin E00026 753 Antimicrobial preservative; Emollient; Flavoring agent; Humectant; Lubricant; Plasticizing agent; Solvent; Suppository base; Tonicity agent; Viscosity-controlling agent
Hexahydric alcohol E00083 5780 Diluent; Flavoring agent; Humectant; Plasticizing agent
Medium-chain triglyceride E00640 Not Available Emollient; Lubricant; Surfactant
Propylene glycol E00040 1030 Antimicrobial preservative; Humectant; Plasticizing agent; Solvent
Silicon dioxide E00670 Not Available Anticaking agent; Opacifying agent; Viscosity-controlling agent
Titanium dioxide E00322 26042 Coating agent; Colorant; Opacifying agent
Water E00035 962 Solvent
⏷ Show the Full List of 18 Pharmaceutical Excipients of This Drug
Pharmaceutical Formulation
Formulation Name Drug Dosage Dosage Form Route
Benzonatate 150 mg capsule 150 mg Oral Capsule Oral
Benzonatate 100 mg capsule 100 mg Oral Capsule Oral
Benzonatate 200 mg capsule 200 mg Oral Capsule Oral
Jump to Detail Pharmaceutical Formulation Page of This Drug

References

1 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 7611).
2 FDA Approved Drug Products from FDA Official Website. 2009. Application Number: (ANDA) 040587.
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.
4 BDDCS predictions, self-correcting aspects of BDDCS assignments, BDDCS assignment corrections, and classification for more than 175 additional drugs
5 Determination of benzonatate and its metabolite in human plasma by HPLC-MS/MS: A preliminary pharmacokinetic study in healthy Chinese volunteers after oral administration of benzonatate soft capsule. J Pharm Biomed Anal. 2019 Sep 5;173:134-143. doi: 10.1016/j.jpba.2019.05.030. Epub 2019 May 16.
6 Bicalho B, Giolo JM, Lilla S, De Nucci G: Identification and human pharmacokinetics of dihydroergotoxine metabolites in man: preliminary results. Biopharm Drug Dispos. 2008 Jan;29(1):17-28. doi: 10.1002/bdd.585.
7 Estimating the safe starting dose in phase I clinical trials and no observed effect level based on QSAR modeling of the human maximum recommended daily dose
8 How many drug targets are there Nat Rev Drug Discov. 2006 Dec;5(12):993-6.
9 Lacosamide: a new approach to target voltage-gated sodium currents in epileptic disorders. CNS Drugs. 2009;23(7):555-68.
10 Effect of sodium channel blockers on ST segment, QRS duration, and corrected QT interval in patients with Brugada syndrome. J Cardiovasc Electrophysiol. 2000 Dec;11(12):1320-9.
11 Medicinal chemistry of neuronal voltage-gated sodium channel blockers. J Med Chem. 2001 Jan 18;44(2):115-37.
12 Halothane attenuates the cerebroprotective action of several Na+ and Ca2+ channel blockers via reversal of their ion channel blockade. Eur J Pharmacol. 2002 Oct 4;452(2):175-81.
13 Monoamine transporter and sodium channel mechanisms in the rapid pressor response to cocaine. Pharmacol Biochem Behav. 1998 Feb;59(2):305-12.
14 From first class to third class: recent upheaval in antiarrhythmic therapy--lessons from clinical trials. Am J Cardiol. 1996 Aug 29;78(4A):28-33.