フェノバルビタール

リキタール · バルビピル · 5-フェニル-5-エチルバルビツル酸 · SK-フェノバルビタール · ルピアール · ソルホトン · 5-エチル-5-フェニル-2,4,6(1H,3H,5H)-ピリミジントリオン · ガルデナール

識別子と物理属性

CAS No.	50-06-6
分子式	C12H12N2O3
平均分子量	232.23 g/mol
単同位体質量	232.08479224 g/mol
SMILES	CCC1(c2ccccc2)C(=O)NC(=O)NC1=O
InChIKey	DDBREPKUVSBGFI-UHFFFAOYSA-N
PubChem CID	4763
ChEMBL	CHEMBL40
ChEBI	CHEBI:8069
EC No.	200-007-0
DTXSID	DTXSID5021122
現地名	フェノバルビタール

化学・物理的性質

XLogP	1.5
極性表面積	75.3
水素結合供与体数	2
水素結合受容体数	3
回転可能結合数	2
重原子数	17
形式電荷	0
複雑度	339
医薬品	DEA NFLIS-Drug Category -> Depressants and TranquilizersDEA Schedule IV Controlled Substance -> DepressantsPharmaceuticals -> Diuretics (Barbiturates)Pharmaceuticals -> Metabolite of PrimidonePharmaceuticals -> Synthetic Cannabinoids or Psychoactive CompoundsPharmaceuticals -> Listed in ZINC15
pH	Saturated soln in water has a pH of about 5
SpringerMaterials Properties	15N nuclear magnetic resonance spectrum
LogP（分配係数）	log Kow = 1.471.32
臭い	Odorless
味	Slightly bitter taste
Color/Form	Crystals (3 different phases)Platelets from waterWhite, shining, crystalline powderWhite, glistening, small crystals or a white, crystalline powder which may show polymorphism
溶解度	less than 0.1 mg/mL at 57 °F (NTP, 1992)1 g soluble in: about 1 L water8 mL alcohol40 mL chloroform12 mL etherabout 700 mL benzene. Solluble in alkali hydroxides and carbonates.LOW LIPID SOLUBILITYInsoluble in benzenesoluble in ethanol, ethyl etherslightly soluble in dimehtyl sulfoxideSoluble in alcohol, ether, chloroform, alkali hydroxides, alkali carbonate solutions水に非常に溶けにくく、エタノール（96%）に溶けやすい。アルカリ金属水酸化物、炭酸塩、アンモニアと水溶性化合物を形成します。<0.01 g/100 mL で 14 ºC
引火点	345 °F (NTP, 1992)11 °C
Human Drugs	Breast FeedingLactationMilk, HumanAnticonvulsantsBarbituratesHypnotics and SedativesGABA ModulatorsAntiseizure medicines
Animal Drugs	Active Ingredients (Phenobarbital) -> FDA GreenbookPharmaceuticals -> UK Veterinary Medicines Directorate ListPharmaceuticals -> Animal Drugs -> Approved in Taiwan
Endocrine Disruptors	Potential endocrine disrupting compound
融点	174°C
沸点	374.4°C (rough estimate)
密度	1.2243 (rough estimate)
屈折率	1.6660 (estimate)
貯蔵条件	2-8°C
外観・状態	Solid
pKa（酸解離定数）	7.3, 11.8(at 25℃)
色	White to Off-White
Merck	13,7319
ヘンリー定数	5.8×108 mol/(m3Pa) at 25℃, HSDB (2015)
BCS Class	1
安定性	安定。可燃性。強力な酸化剤とは相容れない。
CAS データベース	50-06-6(CAS DataBase Reference)
NISTの化学物質情報	Barbituric acid, 5-ethyl-5-phenyl-,(50-06-6)
EPAの化学物質情報	Phenobarbital (50-06-6)

化学的特性

Crystalline Solid

安全性と法規制

GHS 分類	DangerH301 (99.5%): Toxic if swallowed [Danger Acute toxicity, oral]P203, P261, P264, P270, P272, P280, P301+P316, P302+P352, P318, P321, P330, P333+P317, P362+P364, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 195 reports by companies from 13 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.H350: May cause cancer [Danger Carcinogenicity]
規制情報	Hazard Traits - CarcinogenicityDEA schedule IV controlled substanceStatus: Active Update: 23-03-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/23297Phenobarbital: Does not have an individual approval but may be used under an appropriate group standard
その他の安全情報	IMAP assessments - 2,4,6(1H,3H,5H)-Pyrimidinetrione, 5-ethyl-5-phenyl-: Human health tier I assessment
輸送ラベル（DOT）	Poison
火災危険	This chemical is combustible. (NTP, 1992)
健康有害性	SYMPTOMS: Symptoms of exposure to this class of compounds via ingestion include sedation, nystagmus, ataxia, irritability and hyperexcitability in children, exfoliative dermatitis and hypoprothrombinemia in the neonate. Other symptoms via ingestion include confusion and restlessness in the elderly or in the presence of painrespiratory depression, occasional allergic reactions, particularly affecting the skinmaculopapular skin rash, fixed-drug eruptions purpura, photosensitivity, erythema multiforme (the Stevens-Johnson syndrome), toxic epidermal necrolysis, hypothermia with associated pyrexia during recoveryhepatitis, cholestasis, nephritis, hepatic dysfunction and shoulder-hand syndrome. Ingestion may cause agitation in the elderly, hemorrhage in the neonate, morbilliform or scarlatiniform rash, megaloblastic anemia and osteomalacia. Ingestion can also cause sleepiness, unsteadiness, mental confusion, slow and shallow respiration, flaccid muscles, hypotension, cyanosis, hyperthermia, absent reflexes and coma. The duration of coma is dependent on the dose. Cerebral edema contributes to the persistence of coma. If coma persists, moist rales are heard in the lower lung fields, indicating pulmonary edema. Atelectasis or aspiration pneumonia with signs of lung consolidation and fever can also occur. Carbon dioxide retention under these conditions can cause acidosis. Death may occur from pneumonia, pulmonary edema or refractory hypotension. Other symptoms of exposure may include drowsiness, headache, irregular respiration and central nervous system effects Inhalation of the dust may cause irritation of the upper respiratory tract. Hypnosis and excitement have been reported. Other reported symptoms include delirium and deep unconsciousness. It can cause poor judgment and hangover. Chronic symptoms include effects on neurological and pyschic functions, disorientation, skin rash, ataxia, dizziness, depression an foliate deficiency. Chronic exposure may also result in drowsiness, emotional lability, irritability, neglect of personal appearance and other behavior disturbances. Other symptoms of chronic exposure are nystagmus, tremor, mild changes in mental condition such as loss of memory, inability to concentrate, giddiness, depression and dullness of mental perception, and precipitation of acute porphyria. Overdosage may cause hemorrhagic and erythematous bullae, respiratory depression, cardiovascular depression, hypotension and shock leading to renal failure

用途

解説

フェノバルビタール,白色の結晶．融点174～178 ℃．エタノール，エーテル，アセトンに易溶，クロロホルムに可溶，水に難溶．pK1 7.3，pK2 11.8．λmax 240 nm(ε 6600)．バルビツル酸系の長時間型催眠薬で，抗けいれん作用も強く，抗てんかん薬としても用いられる．LD50 660 mg/kg(ラット，経口)．

用途

中枢神経系を抑制し、催眠作用や鎮静作用を有する。抗てんかん薬にも用いる。

説明

Phenobarbital (Item No. 9001494) is an analytical reference material categorized as a barbiturate. Phenobarbital is regulated as a Schedule IV compound in the United States. This product is intended for research and forensic applications.

使用

Phenobarbital exhibits relaxant, soporific, and anticonvulsant activities. It is widely used in treating epilepsy, chorea, and spastic paralysis, and is used as a component of a large number of combined drugs, valocordin and corvalol in particular.

一般的な説明

Phenobarbital, 5-ethyl-5-phenylbarbituricacid (Luminal), is a long-acting sedative and hypnotic.It is also a valuable anticonvulsant, especially in generalizedtonic–clonic and partial seizures (see the discussionon anticonvulsants). Metabolism to the p-hydroxylphenylcompound followed by glucuronidation accounts for about90% of a dose.