Compound: phenobarbital
SMILES: O=C1NC(=O)C(c2ccccc2)(CC)C(N1)=O
InChIKey: DDBREPKUVSBGFI-UHFFFAOYSA-N
Synonyms: phenobarbital, Phenobarbitone, Luminal, Phenobarbitol, 50-06-6, Fenobarbital, Nunol, Phenylethylbarbiturate, Dormiral, Gardenal, Gardepanyl, Neurobarb, Phenobarbituric acid, Adonal, Agrypnal, Barbenyl, Barbiphenyl, Barbipil, Barbivis, Cratecil, Eskabarb, Liquital, Lubergal, Phenaemal, Phenonyl, Phenyral, Solfoton, Etilfen, Euneryl, Noptil, Somonal, Phenylethylmalonylurea, Phenylethylbarbituric acid, Amylofene, Aphenylbarbit, Aphenyletten, Barbophen, Bialminal, Calmetten, Codibarbita, Coronaletta, Dezibarbitur, Fenylettae, Glysoletten, Hennoletten, Hypnaletten, Hypnolone, Hypnoltol, Lepinaletten, Lumesettes, Lumofridetten, Pharmetten, Phenemalum, Phenobarbyl, Phenoluric, Phenolurio, Phenoturic, Phenyletten, Polcominal, Promptonal, Sedizorin, Sedonettes, Somnolens, Somnoletten, Spasepilin, Starilettae, Versomnal, Aephenal, Barbita, Barbonal, Bardorm, Cabronal, Calminal, Cardenal, Doscalun, Duneryl, Ensobarb, Ensodorm, Epidorm, Episedal, Epsylone, Fenbital, Fenemal, Fenosed, Haplopan, Hypnogen, Lepinal, Linasen, Lixophen, Lubrokal, Lumesyn, Luphenil, Luramin, Molinal, Nirvonal, Parkotal, Phenemal, Phenomet, Sedabar, Sedicat, Sedofen, Sedonal, Sedophen, Sevenal, Sombutol, Starifen, Talpheno, Teolaxin, Bartol, Epanal, Epilol, Haplos, Leonal, Lumen, Sedlyn, Seda-Tablinen, Blu-phen, Nova-Pheno, Hypno-Tablinetten, Phen-Bar, Stental Extentabs, 5-Ethyl-5-phenylbarbituric acid, Phenobarb, PHOB, Triabarb, Triphenatol, SK-Phenobarbital, Phenobarbitalum, Tridezibarbitur, Lephebar, Lefebar, Zadonal, 5-Phenyl-5-ethylbarbituric acid, Austrominal, Thenobarbital, 5-ethyl-5-phenylpyrimidine-2,4,6(1H,3H,5H)-trione, Tedral, 5-ethyl-5-phenyl-1,3-diazinane-2,4,6-trione, 2,4,6(1H,3H,5H)-Pyrimidinetrione, 5-ethyl-5-phenyl-, Phenylethylbarbitursaeure, Phenylaethylbarbitursaeure, Barbituric acid, 5-ethyl-5-phenyl-, 5-Ethyl-5-phenyl-2,4,6(1H,3H,5H)-pyrimidinetrione, 5-Ethyl-5-phenyl-pyrimidine-2,4,6-trione, PHENOBARBITAL CIV, NSC-9848, 5-Ethyl-5-phenyl-2,4,6-(1H,3H,5H)pyrimidinetrione, YQE403BP4D, NSC-128143, CHEBI:8069, DTXSID5021122, DTXCID701122, NSC9848, NSC128143, theominal, Phenobarbital, Monosodium Salt, pheno, Phenobarbital Oral, Sodium, Phenobarbital, RefChem:6120, Acid, Phenylethylbarbituric, Phenobarbital Oral Solution, Monosodium Salt Phenobarbital, 200-007-0, Phenylbarbital, Phenobal, Hypnette, Somnosan, Chinoin, Henotal, Hysteps, Solu-Barb, Stental, Zadoletten, Barbinal, Barbiphen, Damoral, Dormina, Teoloxin, Theoloxin, Dormital, Barbilehae (barbilettae), component of Tedral, Sedonal (sedative), component of Slowten, component of Antrocol, component of Hecadrol, component of Bronkotabs, component of Primatene P, CHEMBL40, component of Valpin 50-PB, Phenobarbitonum, NCGC00159493-02, Fenobarbitale, Fenobarbitale [DCIT], Elixir of phenobarbital, Phenobarbitalum [INN], Chardonna-2, Phenylethyl barbituric acid, Fenobarbital [INN-Spanish], Phenyl-ethyl-barbituric acid, Phenobarbitalum [INN-Latin], WLN: T6VMVMV FHJ F2 FR, Barbinol, Fenemal recip, Phenobarbital (5.0mg/ml in DMSO), Phenobarbital (1.0mg/mL in Methanol), Phenobarbital (5.0mg/ml in Methanol), CAS-50-06-6, Levsin PB Drops and Tablets, CCRIS 502, Luminal (TN), phenobarbital (PB), Acido 5-fenil-5-etilbarbiturico, HSDB 3157, Acido 5-fenil-5-etilbarbiturico [Italian], 5-Ethyl-5-phenyl-2,6(1H,3H,5H)-pyrimidinetrione, EINECS 200-007-0, UNII-YQE403BP4D, 2,6(1H,3H,5H)-Pyrimidinetrione, 5-ethyl-5-phenyl-, NSC 128143, Phenobar, AI3-02726, Phenobarbital [USP:INN:BAN:JAN], Tedral (Salt/Mix), TEDRIGEN, THEOPHED, Kinesed (Salt/Mix), Antrocol (Salt/Mix), Donnatal (Salt/Mix), Donnazyme (Salt/Mix), Quadrinal (Salt/Mix), Mephobarbital M (nor), Barbidonna (Salt/Mix), Bronkotabs (Salt/Mix), TEDRAL SUSPENSION, 5-Ethyl-5-phenyl-2,4,6-pyrimidinetrione, Chardonna-2 (Salt/Mix), PHENOBARBITAL [MI], Epitope ID:116048, PHENOBARBITAL [INN], PHENOBARBITAL [JAN], Phenobarbital RS - * psy, PHENOBARBITAL [HSDB], PHENOBARBITAL [IARC], Phenobarbital CRS - * psy, BIDD:PXR0061, Oprea1_384816, SCHEMBL16583, 5-ethyl-5-phenyl-hexahydropyrimidine-2,4,6-trione, Methylphenobarbital, M(nor-), MLS001240232, DivK1c_000987, PHENOBARBITAL [MART.], PHENOBARBITALUM [HPUS], PHENOBARBITAL [WHO-DD], PHENOBARBITAL [WHO-IP], GTPL2804, SCHEMBL11114624, SCHEMBL25330743, HMS503E15, KBio1_000987, Phenobarbital (JP18/USP/INN), NINDS_000987, HMS2272G06, Phenobarbital, 1mg/ml in Methanol, Phenobarbital (5 mg/ml in DMSO), PHENOBARBITAL [EP IMPURITY], PHENOBARBITAL CIV [USP-RS], YCA73805, PHENOBARBITAL [EP MONOGRAPH], Tox21_111713, Tox21_200510, BDBM50021437, PHENOBARBITAL [USP MONOGRAPH], STL367898, component of Primatene P (Salt/Mix), Phenobarbital (1 mg/mL in Methanol), Phenobarbital (5 mg/ml in Methanol), Phenobarbital 0.1 mg/ml in Methanol, Phenobarbital 1.0 mg/ml in Methanol, AKOS000605404, AKOS015964976, Barbituric acid, 5-ethyl-5-phenyl-,, PHENOBARBITALUM [WHO-IP LATIN], AB02704, DB01174, FP32142, component of Valpin 50-PB (Salt/Mix), IDI1_000987, NSC-128143-, Levsin PB Drops and Tablets (Salt/Mix), NCGC00159493-03, NCGC00159493-04, NCGC00258064-01, SMR000058986, PRIMIDONE IMPURITY B [EP IMPURITY], DB-051722, NS00010275, C07434, D00506, Q407241, SR-01000313151, METHYLPHENOBARBITAL IMPURITY A [EP IMPURITY], SR-01000313151-1, pyrimidine-2,4,6(1H,3H,5H)-trione, 5-ethyl-5-phenyl-, Phenobarbital, United States Pharmacopeia (USP) Reference Standard, InChI=1/C12H12N2O3/c1-2-12(8-6-4-3-5-7-8)9(15)13-11(17)14-10(12)16/h3-7H,2H2,1H3,(H2,13,14,15,16,17, UQA
Theoretical properties:
molecular_formula: C12H12N2O3
molecular_weight: 232.23 g/mol
exact_mass: 232.08479225 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 2
hydrogen_bond_acceptor_count: 3
rotatable_bond_count: 2
heavy_atom_count: 17
topological_polar_surface_area: 75.3 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
physical_state: Crystals (3 different phases)
color: Crystals (3 different phases)
odor: Odorless
melting_point: 345 to 352 °F (NTP, 1992)
solubility: less than 0.1 mg/mL at 57 °F (NTP, 1992)
flash_point: 345 °F (NTP, 1992)
Descriptions:
{"pubchem": "Phenobarbital can cause cancer according to The World Health Organization's International Agency for Research on Cancer (IARC).", "chebi": "A member of the class of barbiturates, the structure of which is that of barbituric acid substituted at C-5 by ethyl and phenyl groups.", "chembl": "PHENOBARBITAL is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.", "wikipedia": "Phenobarbital, also known as phenobarbitone, sold under the brand name Luminal among others, is a medication of the barbiturate type. It is recommended by the World Health Organization (WHO) for the treatment of certain types of epilepsy in developing countries. In the developed world, it is commonly used to treat seizures in young children, while other medications are generally used in older children and adults. It is also used for veterinary purposes.\nIt may be administered by slow intravenous infusion (IV infusion), intramuscularly (IM), or orally (swallowed by mouth). Subcutaneous administration is not recommended. The IV or IM (injectable forms) may be used to treat status epilepticus if other drugs fail to achieve satisfactory results. Phenobarbital is occasionally used to treat insomnia, anxiety, and benzodiazepine withdrawal (as well as withdrawal from certain other drugs in specific circumstances), and prior to surgery as an anxiolytic and to induce sedation. It usually begins working within five minutes when used intravenously and half an hour when administered orally. Its effects last for between four hours and two days.\nPotentially serious side effects include a decreased level of consciousness and respiratory depression. There is potential for both abuse and withdrawal following long-term use. It may also increase the risk of suicide.\nIt is pregnancy category D in Australia, meaning that it may cause harm when taken during pregnancy. If used during breastfeeding it may result in drowsiness in the baby. Phenobarbital works by increasing the activity of the inhibitory neurotransmitter GABA.\nPhenobarbital was discovered in 1912 and is the oldest still commonly used anti-seizure medication. It is on the World Health Organization's List of Essential Medicines."}