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アプロバルビタール

Aprobarbital

HCID 6464
ノート反応
基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
部分構造検索類似構造を探す

基本情報

CAS
77-02-1
標準SMILES
C=CCC1(C(C)C)C(=O)NC(=O)NC1=O
InChIKey
UORJNBVJVRLXMQ-UHFFFAOYSA-N
分子式
C10H14N2O3
平均分子量
210.23 g/mol
単同位体質量
210.10044231

概要

Aprobarbital is a member of the class of barbiturates that is pyrimidine-2,4,6(1H,3H,5H)-trione substituted by an isopropyl and a prop-1-en-3-yl group at position 5.

名称と識別子

優先名称
Aprobarbital
IUPAC
5-propan-2-yl-5-prop-2-enyl-1,3-diazinane-2,4,6-trione
現地名
アプロバルビタール
英語名
APROBARBITAL METHANOL SOLUTION
分子式
C10H14N2O3
分子量
210.23

名称と別名

APROBARBITALAllypropymalAlurateAllylpropymalAprobarbitoneAllonalAllionalAprozalNumal77-02-1Alurate elixir verdum5-Allyl-5-isopropylbarbituric acid
名称をさらに表示
5-アリル-5-イソプロピルバルビツル酸アロナールアプロバルビタール5-イソプロピル-5-アリルバルビツル酸アリオナールヌマール5-(1-メチルエチル)-5-(2-プロペニル)ピリミジン-2,4,6(1H,3H,5H)-トリオン5-アリル-5-イソプロピルピリミジン-2,4,6(1H,3H,5H)-トリオンアプロザールアリルプロピマールアプロバルビトンアルラート5-イソプロピル-5-(2-プロペニル)ピリミジン-2,4,6(1H,3H,5H)-トリオンアリプロピマールアルラートエリクシールベルダム5-(プロパ-2-エン-1-イル)-5-(プロパン-2-イル)-1,3-ジアジナン-2,4,6-トリオンIsonalNSC120769Aprobarbita
AllylisopropylmalonylureaIsopropylallylbarbituric acid5-Isopropyl-5-allylbarbituric acidAllylisopropylbarbituric acidAprobarbitalumBarbituric acid, 5-allyl-5-isopropyl-Q0YKG9L6RF5-(1-Methylethyl)-5-(2-propenyl)-2,4,6(1H,3H,5H)-pyrimidinetrione

物性

構造計算による物性

XLogP
1.1
極性表面積
75.3 Ų
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
3
重原子数
15
形式電荷
0
複雑度
314

実験および物理化学的性質

Drugs · 3 件

DEA NFLIS-Drug Category -> Depressants and Tranquilizers

Pharmaceuticals -> Barbiturates

Pharmaceuticals -> Listed in ZINC15

pHA SATURATED AQUEOUS SOLN IS ACID TO LITMUS
SpringerMaterials PropertiesDensity
LogP · 2 件

1.15

1.22

TasteSLIGHTLY BITTER
Color/Form · 2 件

CRYSTALS

Fine, white, crystalline powder

Solubility · 4 件

POWDER; HYGROSCOPIC; SLIGHTLY BITTER TASTE; VERY SOL IN WATER; SLIGHTLY SOL IN ALC; PRACTICALLY INSOL IN ETHER; AQ SOLN ARE ALKALINE TO LITMUS /APROBARBITAL SODIUM SALT/

ALMOST INSOL IN WATER, PETROLEUM ETHER, ALIPHATIC HYDROCARBONS; SOL IN ALC, CHLOROFORM, ETHER, ACETONE, BENZENE, GLACIAL ACETIC ACID, FIXED ALKALI HYDROXIDE SOLN.

Lipid solubility is low.

5.17e+00 g/L

DecompositionWhen heated to decomp it emits toxic fumes of oxides of nitrogen. /Aprobarbital sodium/
Melting Point · 2 件

140-141.5 °C

安全と法規制

安全情報は参考情報です。供給元の安全データシート（SDS）、適用法令、専門家による評価に代わるものではありません。

GHS分類

GHS Classification · 4 件

Danger

H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]

P264, P270, P301+P316, P321, P330, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 40 reports by companies from 1 notifications to the ECHA C&L Inventory.

危険有害性情報

Other Safety InformationIMAP assessments - 2,4,6(1H,3H,5H)-Pyrimidinetrione, 5-(1-methylethyl)-5-(2-propenyl)-: Human health tier I assessment
FDA Requirements · 5 件

Manufacturers, packers, and distributors of drug and drug products for human use are responsible for complying with the labeling, certification, and usage requirements as prescribed by the Federal Food, Drug, and Cosmetic Act, as amended (secs 201-902, 52 Stat. 1040 et seq., as amended; 21 U.S.C. 321-392).

5-Allyl-5-isopropylbarbituric acid is a chemical derivative of barbituric acid, named in section 502(d) of the Federal Food, Drug, and Cosmetic Act, and is hereby designated as habit forming.

Warning and caution statements for 5-allyl-5-isopropylbarbituric acid specifically required by law. PREPARATIONS CONTAINING HABIT-FORMING DERIVATIVES OF SUBSTANCES NAMED IN SECTION 502(d) OF THE FEDERAL FOOD, DRUG, AND COSMETIC ACT ... The statement "Warning-May be habit forming" is required to appear on the labels of all drugs containing derivatives designated in 21 CFR 329.1 ... as habit forming.

Schedules of controlled substances are established by section 202 of the Controlled Substances Act (21 U.S.C. 812). Schedule III includes any substance which contains any quantity of a derivative of barbituric acid or any salt thereof. DEA Code #2100; Drug class: Depressant. /Derivatives of barbituric acid or any salt thereof/

For more FDA Requirements (Complete) data for APROBARBITAL (6 total), please visit the HSDB record page.

Hazard Classes and CategoriesAcute Tox. 3 (100%)

安全と保護具

化学と産業

薬理情報

ATC Code · 2 件

N - Nervous system

QN - Nervous system

Mechanism of Action · 6 件

Aprobarbital (like all barbiturates) works by binding to the GABAA receptor at either the alpha or the beta sub unit. These are binding sites that are distinct from GABA itself and also distinct from the benzodiazepine binding site. Like benzodiazepines, barbiturates potentiate the effect of GABA at this receptor. This GABAA receptor binding decreases input resistance, depresses burst and tonic firing, especially in ventrobasal and intralaminar neurons, while at the same time increasing burst duration and mean conductance at individual chloride channels; this increases both the amplitude and decay time of inhibitory postsynaptic currents. In addition to this GABA-ergic effect, barbiturates also block the AMPA receptor, a subtype of glutamate receptor. Glutamate is the principal excitatory neurotransmitter in the mammalian CNS. Aprobarbital also appears to bind neuronal nicotinic acetylcholine receptors.

... REVERSIBLY DEPRESS ACTIVITY OF ALL EXCITABLE TISSUES. ... CNS IS ... SENSITIVE, SO ... IN SEDATIVE OR HYPNOTIC DOSES, VERY LITTLE EFFECT ON SKELETAL, CARDIAC, OR SMOOTH MUSCLE OCCURS. ... PROBABLE THAT EXCITABILITY IN EACH TISSUE IS DEPRESSED BY AN ACTION ON OR IN A MEMBRANE & THAT ... MECHANISMS ... ARE ... SIMILAR. /BARBITURATES/

AS DOSE ... INCR, HYPOXIC & CHEM DRIVES TO RESP ARE DIMINISHED ... HOWEVER, HYPOXIC DRIVE PERSISTS @ LEVELS OF INTOXICATION CAUSING ... INSENSITIVITY OF RESP CENTERS TO CO2. ... AS INTOXICATION /INCR/ ... THERE IS SHIFT IN CONTROL OF RESP FROM CO2-SENSITIVE AREAS OF MEDULLA TO MORE PRIMITIVE ... CAROTID & AORTIC ... /BARBITURATES/

WHATEVER ... THE EFFECTS OF BARBITURATES ELSEWHERE IN CNS, IT IS EFFECT ON RETICULAR SYSTEM ... RESPONSIBLE FOR INABILITY TO MAINTAIN WAKEFULNESS UNDER INFLUENCE OF A BARBITURATE. /BARBITURATES/

BARBITURATES DECR TURNOVER OF 5-HYDROXYTRYPTAMINE & CATECHOLAMINES IN BRAIN OF EXPTL ANIMALS, BUT WHETHER THIS IS CAUSE OR EFFECT OF ANESTHESIA IS CONJECTURAL. /BARBITURATES/

For more Mechanism of Action (Complete) data for APROBARBITAL (10 total), please visit the HSDB record page.

Biological Half-Life · 2 件

APROBARBITAL DOSE 0.75 G ORAL REACHED CONCN 2.3 MG% IN 3-9 HR; T/2 WAS 24-36 HR. /FROM TABLE/

Plasma half-life is about 14 fto 40 hours.

関連反応

0 件
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現在のフィルター条件では反応記録がありません。

化合物ノート

読み込み中…

このページの内容基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート

データベース識別子

CAS
77-02-1
PubChem CID
6464
DTXSID
DTXSID8022616
ChEMBL
CHEMBL7863
ChEBI
CHEBI:2791
UNII
Q0YKG9L6RF
EC Number
200-997-4
Nikkaji
J38.379A

141 °C

Refractive IndexINDEX OF REFRACTION ALPHA: 1.520; BETA: 1.581; GAMMA: 1.600
Physical DescriptionSolid
Stability/Shelf LifeSTABLE IN AIR

物理化学的性質

融点
140 · 140-141.5°
沸点
349.75 °C · 349.75°C (rough estimate)
比重(密度)
1.2056 · 1.2056 (rough estimate)
屈折率
1.5 · 1.5000 (estimate)
貯蔵温度
2 · 2-8°C
溶解性
DMSO (Slightly), Methanol (Slightly)
酸解離定数(Pka)
7.81 · 7.81±0.10(Predicted)
外見
Solid
色
White to Off-White
水溶解度
4.121 g/L · 4.121g/L(25℃)
主な用途
法医学と毒物学
InChI
1S/C10H14N2O3/c1-4-5-10(6(2)3)7(13)11-9(15)12-8(10)14/h4,6H,1,5H2,2-3H3,(H2,11,12,13,14,15)
InChIKey
UORJNBVJVRLXMQ-UHFFFAOYSA-N
SMILES
O=C1C(C(C)C)(CC=C)C(NC(N1)=O)=O
Storage ConditionsOral solution should be stored in tight, light-resistant containers at a temperature less than 40 °C, preferably between 15 to 30 °C; freezing should be avoided. ... Expiration date /is/ 4 years following the date of manufacture.

毒性情報

Interactions · 5 件

IN CAT CEREBRAL CORTEX, BARBITURATES IN ANESTHETIC DOSES SELECTIVELY ABOLISH EXCITATION BUT NOT INHIBITION ELICITED BY NOREPINEPHRINE APPLIED DIRECTLY TO VARIOUS SYNAPSES... /BARBITURATES/

AT SKELETAL NEUROMUSCULAR JUNCTIONS BLOCKING EFFECTS OF BOTH D-TUBOCURARINE & DECAMETHONIUM ARE ENHANCED BY BARBITURATES. /BARBITURATES/

BOTH CARDIAC GLYCOSIDES & BETA-ADRENERGIC AGONISTS ANTAGONIZE MYOCARDIAL DEPRESSANT ACTION /OF BARBITURATES/. /BARBITURATES/

INTENSITY OF CNS DEPRESSION CAN BE INCR BY ACIDIC DRUGS SUCH AS ASPIRIN ... WHICH DISPLACE BARBITURATES FROM PLASMA PROTEINS. /BARBITURATES/

For more Interactions (Complete) data for APROBARBITAL (14 total), please visit the HSDB record page.

Human Toxicity Excerpts · 5 件

... BARBITURATES REDUCE AMT OF TIME SPENT IN REM PHASE SLEEP, &, IN THIS ... BARBITURATE-INDUCED SLEEP DIFFERS FROM PHYSIOLOGICAL SLEEP. ... CLAIMED ... THAT DEPRIVATION OF THIS PHASE ... MAY HAVE DELETERIOUS EFFECTS. SUBJECTS DEPRIVED OF REM ... EXHIBIT REBOUND INCR IN ... TIME SPENT IN REM SLEEP FOLLOWING ... DEPRIVATION. /BARBITURATE/

PROLONGED USE OF BARBITURATES INCR RESTLESSNESS DURING LATE STAGES OF SLEEP, CAUSES ANXIETY, & INCR PLASMA CONCN OF GROWTH HORMONE BUT DECR THOSE OF ADRENOCORTICOIDS. ... IN SMALL DOSES, BARBITURATES MAY INCR REACTION TO PAINFUL STIMULI. /BARBITURATES/

OXYBARBITURATES TEND TO DECR TONUS OF GI MUSCULATURE & AMPLITUDE OF RHYTHMIC CONTRACTIONS. /OXYBARBITURATES/

SEVERE OLIGURIA OR ANURIA MAY OCCUR IN ACUTE ... POISONING, LARGELY AS RESULT OF MARKED HYPOTENSION. /BARBITURATES/

For more Human Toxicity Excerpts (Complete) data for APROBARBITAL (17 total), please visit the HSDB record page.

Antidote and Emergency Treatment · 4 件

TREATMENT: Stabilization: Respiratory arrest is the major cause of early death. Assess the patency of the airway and the adequacy of ventilation first. Appropriate corrective measures include supplemental oxygen, head tilt-chin lift, intubation, and assisted ventilation. Establish an iv line with Ringer's lactate and give a fluid challenge up to 2 l for patients who are hypotensive. Cardiac dysrhythmias are rare but were reported. ... Be sure to give glucose, naloxone, and thiamine to all patients with depressed mental status. /Barbiturates/

Gut Decontamination: Because of decr gastrointestinal mobility and delayed gastric emptying, gut decontamination is indicated 6-8 hr postingestion in obtunded patients. Barbiturates are well absorbed by charcoal; 10 times the ingested dose (or 1 g/kg body weight) should be given together with a cathartic (sorbitol, magnesium citrate) to all patients. /Barbiturates/

Elimination Enhancement: Most overdose patients respond to supportive care and require no special measures. ... Alkaline diuresis is ineffective for short and intermediate acting barbiturates. ... Hemoperfusion: This measure is more effective than dialysis for short and intermediate acting barbiturates. ...

Antidotes: No effective antidotes are available. Respiratory and central nervous stimulants incr complications and should be avoided. /Barbiturates/

法規制情報

FDA Requirements · 5 件

Manufacturers, packers, and distributors of drug and drug products for human use are responsible for complying with the labeling, certification, and usage requirements as prescribed by the Federal Food, Drug, and Cosmetic Act, as amended (secs 201-902, 52 Stat. 1040 et seq., as amended; 21 U.S.C. 321-392).

5-Allyl-5-isopropylbarbituric acid is a chemical derivative of barbituric acid, named in section 502(d) of the Federal Food, Drug, and Cosmetic Act, and is hereby designated as habit forming.

Warning and caution statements for 5-allyl-5-isopropylbarbituric acid specifically required by law. PREPARATIONS CONTAINING HABIT-FORMING DERIVATIVES OF SUBSTANCES NAMED IN SECTION 502(d) OF THE FEDERAL FOOD, DRUG, AND COSMETIC ACT ... The statement "Warning-May be habit forming" is required to appear on the labels of all drugs containing derivatives designated in 21 CFR 329.1 ... as habit forming.

Schedules of controlled substances are established by section 202 of the Controlled Substances Act (21 U.S.C. 812). Schedule III includes any substance which contains any quantity of a derivative of barbituric acid or any salt thereof. DEA Code #2100; Drug class: Depressant. /Derivatives of barbituric acid or any salt thereof/

For more FDA Requirements (Complete) data for APROBARBITAL (6 total), please visit the HSDB record page.

安全データ

wgk
WGK 2
毒性
LD50 i.p. in mice: 200 mg/kg (Frey)
risk_code
11-23/25-36/38
hazard_code
F,T
safety_code
16-24-45
Hazard Classifications
Acute Tox. 3 DermalAcute Tox. 3 InhalationAcute Tox. 3 OralFlam. Liq. 2STOT SE 1
ストレージクラス
3 - Flammable liquids
有毒物質データの
77-02-1(Hazardous Substances Data)
DEA Controlled Substances
CSCN: 2100CSA SCH: Schedule IIINARC: No
Metabolism/Metabolites · 4 件

PARTLY METABOLIZED IN LIVER BY OXIDN OF C-5 SUBSTITUENT(S) (ALLYL &/OR ISOPROPYL GROUPS) ... ALLYL GROUP ... MAY ALSO /BE REMOVED/. RESULTING /IN/ INACTIVE METABOLITES /HUMAN, ORAL/.

Hepatic biotransformation, primarily by the hepatic microsomal enzyme system. /barbiturates/

Partially metabolized in the liver by oxidation of the C5 substituent(s) (allyl and/or isopropyl groups). Removal of the allyl group at C5 may also occur. The resulting inactive metbolites, which have not been identified are excreted in the urine.

With the exception of the less lipid-soluble aprobarbital and phenobarbital, nearly complete metabolism and/or conjugation of barbiturates in the liver precedes their renal excretion. The oxidation of radicals at C5 is the most important biotransformation responsible for termination of biological activity. Oxidation results in the formation of alcohols, ketones, phenols, or carboxylic acids, which may appear in the urine as such or as glucuronic acid conjugates. In some instances (eg, phenobarbital), N-glucosylation is an important metabolic pathway. Other biotransformations include N-hydroxylation, desulfuration of thiobarbiturates to oxybarbiturates, opening of the barbituric acid ring, and N-dealkylation of N-alkylbarbiturates to active metabolites (eg, mephobarbital to phenobarbital).

Absorption, Distribution and Excretion · 5 件

RATE OF DECLINE OF BLOOD CONCN AFTER A LARGE DOSE FOR ... ALURATE ... IS 25-40% /PER 24 HR/ ... RATE OF DECLINE IS A FUNCTION OF ACCUMULATION IN LIVER, METAB OF DRUG & URINARY EXCRETION.

AS MUCH AS 50% OF HYPNOTIC DOSE OF ... APROBARBITAL MAY BE EXCRETED UNCHANGED BY KIDNEY. ... APROBARBITAL ... ELIMINATED SLOWLY, OVER A PERIOD OF SEVERAL DAYS.

A FRACTION OF BARBITURATE IN BLOOD IS REVERSIBLY BOUND TO PLASMA PROTEIN, CHIEFLY ALBUMIN. ... THE CEREBROSPINAL FLUID IS VIRTUALLY PROTEIN FREE. ACCORDINGLY, THE MAXIMAL CONCN OF BARBITURATES ATTAINED IN CEREBROSPINAL FLUID IS LESS THAN THE PLASMA CONCN, BEING IN MOST CASES SLIGHTLY LESS THAN THE CONCN IN AN ULTRAFILTRATE OF PLASMA. THE CONCN IN OCULAR FLUID IS SIMILAR TO THAT OF CEREBROSPINAL FLUID. IN TISSUES, THE BARBITURATE CONCN IS GENERALLY AS HIGH AS OR SLIGHTLY HIGHER THAN IN PLASMA. /BARBITURATES/

... SODIUM SALTS ARE MORE RAPIDLY ABSORBED THAN FREE ACIDS ... FOOD IN STOMACH DECR RATE OF ABSORPTION BUT NOT AMT ABSORBED. THERE EXISTS NO IMPENETRABLE BARRIER TO ... BARBITURATES IN BODY ... IF SOJOURN OF DRUG IN PLASMA IS SUFFICIENTLY LONG, IT WILL BE DISTRIBUTED TO ALL TISSUES & FLUIDS. /BARBITURATES/

For more Absorption, Distribution and Excretion (Complete) data for APROBARBITAL (10 total), please visit the HSDB record page.

Cellular LocationsMembrane

用途と製造

UsesMEDICATION
Formulations/Preparations · 2 件

Alurate Elixir, oral solution with aprobarbital 40 mg/5 ml and alcohol 20%.

Oral solution: 40 mg/5 ml, Alierate on Elixis (C-III with 20% alc)

応用分野

使用Controlled substance (depressant). Sedative, hypnotic.

上流・下流製品情報

上流原料

水酸化ナトリウムアリルブロミド5-イソプロピル-2,4,6(1H,3H,5H)-ピリミジントリオン

補足説明

定義ChEBI: A member of the class of barbiturates that is pyrimidine-2,4,6(1H,3H,5H)-trione substituted by an isopropyl and a prop-1-en-3-yl group at position 5.