Compound: Benzonatate
SMILES: O=C(OCCOCCOCCOCCOCCOCCOCCOCCOCCOC)c1ccc(NCCCC)cc1
InChIKey: MAFMQEKGGFWBAB-UHFFFAOYSA-N
Synonyms: Benzonatate, 104-31-4, Benzononatine, Tessalon, Benzonatatum, Benzonatato, Tessalon Perles, Zonatuss, 2,5,8,11,14,17,20,23,26-nonaoxaoctacosan-28-yl 4-(butylamino)benzoate, DTXSID9022655, 2,5,8,11,14,17,20,23,26-Nonaoxaoctacosan-28-yl p-(butylamino)benzoate, nonaethyleneglycol monomethyl ether p-n-butylaminobenzoate, NSC-760128, 4-(butylamino)benzoic acid 3,6,9,12,15,18,21,24,27-nonaoxaoctacos-1-yl ester, Benzoic acid, 4-(butylamino)-, 2,5,8,11,14,17,20,23,26-nonaoxaoctacos-28-yl ester, CHEBI:3032, DTXCID902655, p-butylaminobenzoic acid omega-O-methylnonaethyleneglycol ester, 3,6,9,12,15,18,21,24,27-nonaoxaoctacosyl 4-butylaminobenzoate, 2-[2-[2-[2-[2-[2-[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethyl 4-butylaminobenzoate, KM-65, 2-(2-(2-(2-(2-(2-(2-(2-(2-methoxyethoxy)ethoxy)ethoxy)ethoxy)ethoxy)ethoxy)ethoxy)ethoxy)ethyl 4-butylaminobenzoate, RefChem:6896, R05DB01, 203-194-7, 5P4DHS6ENR, Benzonatate (USP-RS), Benzononantin, Exangit, Ventussin, Tessalon-ciba, Ventussin-loz, Tessalin, Benzonatatum [INN-Latin], Benzonatato [INN-Spanish], KM65, Benzoic acid, 4-(butylamino)-, 3,6,9,12,15,18,21,24,27-nonaoxaoctacos-1-yl ester, MFCD00072060, Tesalon, p-(n)-Butylaminobenzoesaeure-(nonaaethylenglykol-monomethylaether)-ester, 2-[2-[2-[2-[2-[2-[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethyl 4-(butylamino)benzoate, Benzoic acid, p-(butylamino)-, 2-(2-(2-(2-(2-(2-(2-(2-(2-methoxyethoxy)ethoxy)ethoxy)ethoxy)ethoxy)ethoxy)ethoxy)ethoxy)ethyl ester, NCGC00016362-01, CAS-104-31-4, C30H53NO11, 3,6,9,12,15,18,21,24,27-Nonaoxaoctacosyl-4-butylaminobenzoate;3,6,9,12,15,18,21,24,27-Nonaoxaoctacosyl-4-butylaminobenzoate, Tessalon perles (TN), Benzonatate (USP/INN), EINECS 203-194-7, Benzonatate [USP:INN:BAN], HSDB 7933, p-(n)-Butylaminobenzoesaeure-(nonaaethylenglykol-monomethylaether)-ester [German], Prestwick0_000012, Prestwick1_000012, Prestwick2_000012, Prestwick3_000012, SCHEMBL28366, BSPBio_000043, MLS002154171, SPBio_001964, BPBio1_000049, GTPL7611, orb1306954, CHEMBL1374379, HMS1568C05, HMS2095C05, HMS2230M19, HMS3373I11, HMS3712C05, Pharmakon1600-01503864, HY-B1551, Tox21_110398, EBC-27376, NSC760128, 3,6,9,12,15,18,21,24,27-Nonaoxaoctacos-1-yl 4-(butylamino)benzoate, AKOS015891366, Tox21_110398_1, CCG-213706, DB00868, NSC 760128, NCGC00016362-02, NCGC00016362-03, NCGC00016362-05, DA-71391, MS-30648, SMR001233469, AB00513795, CS-0013413, NS00014318, D00242, H51210, AB00513795_06, EN300-19736044, SR-01000841197, Q2070778, SR-01000841197-2, BRD-K91699951-001-10-2, Nonaethyleneglycol-p-n-butylaminobenzoate methyl ester, 3,6,9,12,15,18,21,24,27-Nonaoxaoctacos-1-yl 4-(butylamino)benzoate #, Benzononantin; 2,5,8,11,14,17,20,23,26-nonaoxaoctacosan-28-yl 4-(butylamino)benzoate
Theoretical properties:
molecular_formula: C30H53NO11
molecular_weight: 603.7 g/mol
exact_mass: 603.36186151 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 1
hydrogen_bond_acceptor_count: 12
rotatable_bond_count: 33
heavy_atom_count: 42
topological_polar_surface_area: 121 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
physical_state: Colorless to faintly yellow oil
color: Colorless to faintly yellow oil
solubility: Soluble in most organic solvents except aliphatic hydrocarbons
Descriptions:
{"pubchem": "Benzonatate is the ester obtained by formal condensation of 4-butylaminobenzoic acid with nonaethylene glycol monomethyl ether. Structurally related to procaine and benzocaine, it has an anaesthetic effect on the stretch sensors in the lungs, and is used as a non-narcotic cough suppressant. It has a role as an anaesthetic and an antitussive. It is a benzoate ester, a substituted aniline and a secondary amino compound. It is functionally related to a 4-(butylamino)benzoic acid and a nonaethylene glycol monomethyl ether.", "chebi": "The ester obtained by formal condensation of 4-butylaminobenzoic acid with nonaethylene glycol monomethyl ether. Structurally related to procaine and benzocaine, it has an anaesthetic effect on the stretch sensors in the lungs, and is used as a non-narcotic cough suppressant.", "chembl": "BENZONATATE is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.", "wikipedia": "Benzonatate (), sold under the brand name Tessalon among others, is a medication that is used for the symptomatic relief of cough. Benzonatate is taken by mouth. Effects generally begin within 20 minutes and last between 3 and 8 hours.\nSide effects include sleepiness, dizziness, headache, upset stomach, skin rash, hallucinations, and allergic reactions. Overdosage can result in serious adverse effects including seizures, irregular heartbeat, cardiac arrest, and death. Overdose of only a small number of capsules can be fatal. Chewing or sucking on the capsule, releasing the drug into the mouth, can also lead to laryngospasm, bronchospasm, and circulatory collapse. It is unclear if use in pregnancy or breastfeeding while on the medication is safe. Benzonatate is a local anesthetic and voltage-gated sodium channel blocker. It is theorized to work by inhibiting stretch receptors in the lungs, in turn suppressing the cough reflex in the brain. Benzonatate is structurally related to other local anesthetics like procaine and tetracaine.\nBenzonatate was discovered in 1956 and was approved for medical use in the United States in 1958. It is available as a generic medication. Availability worldwide is limited, with the drug remaining marketed only in the United States and Mexico. In 2023, it was the 122nd most commonly prescribed medication in the United States, with more than 5 million prescriptions. A 2023 systematic review found that there is inadequate evidence to support the effectiveness and safety of benzonatate for cough and highlighted rising safety concerns.\n\n"}