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]
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Therapeutic Class

Antitussives

Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 3

Molecular Weight (mw)

603.7

Logarithm of the Partition Coefficient (xlogp)

2.4

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

ADMET Property

Absorption Cmax: The maximum plasma concentration (Cmax) of drug is 1063 +/- 460 mcg/L [2]
BDDCS Class: Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 2: low solubility and high permeability [3]
Half-life: The concentration or amount of drug in body reduced by one-half in 100 mg in hours [4]
Metabolism: The drug is metabolized via plasma butyrylcholinesterase (BChE) [5]
MRTD: The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 14.19682 micromolar/kg/day [6]

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	[7]

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Molecular Interaction Atlas (MIA)

MIA Detail

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
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⏷ 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	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.
3	BDDCS predictions, self-correcting aspects of BDDCS assignments, BDDCS assignment corrections, and classification for more than 175 additional drugs
4	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.
5	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.
6	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
7	How many drug targets are there Nat Rev Drug Discov. 2006 Dec;5(12):993-6.