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ジブカイン

Dibucaine

HCID 3025
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
85-79-0
標準SMILES
CCCCOc1cc(C(=O)NCCN(CC)CC)c2ccccc2n1
InChIKey
PUFQVTATUTYEAL-UHFFFAOYSA-N
分子式
C20H29N3O2
平均分子量
343.5 g/mol
単同位体質量
343.22597718

概要

Cinchocaine is a monocarboxylic acid amide that is the 2-(diethylamino)ethyl amide of 2-butoxyquinoline-4-carboxylic acid. One of the most potent and toxic of the long-acting local anesthetics, its parenteral use was restricted to spinal anesthesia. It is now generally only used (usually as the hydrochloride) in creams and ointments and in suppositories for temporary relief of pain and itching associated with skin and anorectal conditions. It has a role as a topical anaesthetic. It is a monocarboxylic acid amide, an aromatic ether and a tertiary amino compound.

名称と識別子

優先名称
Dibucaine
IUPAC
2-butoxy-N-[2-(diethylamino)ethyl]quinoline-4-carboxamide
現地名
ジブカイン
英語名
Cinchocaine
分子式
C20H29N3O2
分子量
343.46

名称と別名

dibucaineCinchocaine85-79-0NupercainalDermacaineDibucaine BaseDibucain2-butoxy-N-[2-(diethylamino)ethyl]quinoline-4-carboxamideCinchocainumCincocainaCincocainioDibucaine [USP]
名称をさらに表示
デルマカイン2-ブトキシ-N-[2-(ジエチルアミノ)エチル]-4-キノリンカルボアミドヌペルカイナールソブカインシンコカイン2-ブトキシ-N-(2-ジエチルアミノエチル)-4-キノリンカルボアミドジブカイン塩基ジブカイン2-ブトキシ-N-[2-(ジエチルアミノ)エチル]シンコニンアミド2-ブトキシ-N-[2-(ジエチルアミノ)エチル]-4-キノリンカルボキサミドN-[2-(ジエチルアミノ)エチル]-2-ブトキシ-4-キノリンカルボアミド2-ブチルオキシ-N-[2-(ジエチルアミノ)エチル]-4-キノリンカルボアミドヌペルカインペルカミンS2-ブトキシ-N-[2-(ジエチルアミノ)エチル]キノリン-4-カルボキサミドpercamineINN / BANNupercaineZinn cocaine
2-butoxy-N-(2-(diethylamino)ethyl)quinoline-4-carboxamide2-Butoxyquinoline-4-carboxylic acid diethylaminoethylamideDibucaine (USP)DTXSID30452712-Butoxy-N-(2-(diethylamino)ethyl)cinchoninamide2-Butoxy-N-(beta-diethylaminoethyl)cinchoninamide2-N-Butoxy-N-(2-diethylaminoethyl)cinchoninamideN-(2-(Diethylamino)ethyl)-2-butoxycinchoninamide

物性

構造計算による物性

XLogP
4.4
極性表面積
54.5 Ų
水素結合供与体数
1
水素結合受容体数
4
回転可能結合数
10
重原子数
25
形式電荷
0
複雑度
387

実験および物理化学的性質

Drugs · 2 件

Pharmaceuticals

Pharmaceuticals -> Listed in ZINC15

SpringerMaterials PropertiesNuclear quadrupole resonance spectroscopy
LogP · 3 件

log Kow= 4.40

4.2

4.19

OdorOdorless
Color/FormColorless or almost colorless powder
Solubility · 5 件

Hydroscopic crystals; decomp @ 90-98 °C; faintly alkaline to litmus (aq soln, 1 in 20); freely sol in alc, acetone, chloroform; sol in 0.5 part water; slightly sol in benzene, ethyl acetate, toluene (on warming); insol in ether, oils /Dibucaine hydrochloride/

INSOL IN WATER; SOL IN ETHANOL, CHLOROFORM, ETHER, PETROLEUM ETHER

Soluble in alcohol and acetone; slightly soluble in water.

3.89e-02 g/L

>51.5 [ug/mL] (The mean of the results at pH 7.4)

Human Drugs · 2 件

Breast Feeding; Lactation; Anesthetics, Local

Pharmaceuticals

DecompositionWhen heated to decomposition it emits toxic fumes of nitroxides.
Melting Point

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

H302 (92.7%): Harmful if swallowed [Warning Acute toxicity, oral]

P264, P264+P265, P270, P280, P301+P317, P305+P354+P338, P317, P330, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 41 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

危険有害性情報

Regulatory Information · 2 件

REACH registered substance: Cinchocaine (EC: 201-632-1)

Cinchocaine: Does not have an individual approval but may be used under an appropriate group standard

Other Safety InformationIMAP assessments - 4-Quinolinecarboxamide, 2-butoxy-N-[2-(diethylamino)ethyl]-: Environment tier I assessment
FDA Requirements · 1 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).

Hazard Classes and CategoriesAcute Tox. 4 (92.7%)

安全と保護具

Disposal Methods · 1 件

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

毒性情報

化学と産業

薬理情報

ATC Code · 6 件

N - Nervous system

D - Dermatologicals

S - Sensory organs

S - Sensory organs

C - Cardiovascular system

QD - Dermatologicals

PharmacodynamicsDibucaine is an amide-type local anesthetic, similar to lidocaine.
Mechanism of Action · 6 件

Local anesthetics block both the initiation and conduction of nerve impulses by decreasing the neuronal membrane's permeability to sodium ions through sodium channel inhibition. This reversibly stabilizes the membrane and inhibits depolarization, resulting in the failure of a propagated action potential and subsequent conduction blockade.

... PREVENT THE GENERATION & THE CONDUCTION OF THE NERVE IMPULSE. THEIR PRIMARY SITE OF ACTION IS THE CELL MEMBRANE. ... BLOCK CONDUCTION BY DECREASING OR PREVENTING THE TRANSIENT INCREASE IN THE PERMEABILITY OF EXCITABLE MEMBRANES TO NA IONS THAT IS NORMALLY PRODUCED BY A SLIGHT DEPOLARIZATION ... /LOCAL ANESTHETICS/

AS ANESTHETIC ACTION PROGRESSIVELY DEVELOPS IN A NERVE, THE THRESHOLD FOR ELECTRICAL EXCITABILITY GRADUALLY INCREASES, THE RATE OF RISE OF THE ACTION POTENTIAL DECLINES, IMPULSE CONDUCTION SLOWS, & THE SAFETY FACTOR FOR CONDUCTION DECREASES; THESE FACTORS DECREASE PROBABILITY OF PROPAGATION OF THE ACTION POTENTIAL, AND NERVE CONDUCTION FAILS. /LOCAL ANESTHETICS/

... CAN BLOCK K ION CHANNELS. ... BLOCKADE OF CONDUCTION IS NOT ACCOMPANIED BY ANY LARGE OR CONSISTENT CHANGE IN RESTING MEMBRANE DUE TO BLOCK OF K ION CHANNELS. /LOCAL ANESTHETICS/

... SITE AT WHICH LOCAL ANESTHETICS ACT, AT LEAST IN THEIR CHARGED FORM, IS ACCESSIBLE ONLY FROM THE INNER SURFACE OF THE MEMBRANE. ... LOCAL ANESTHETICS APPLIED EXTERNALLY FIRST MUST CROSS THE MEMBRANE BEFORE THEY CAN EXERT A BLOCKING ACTION. /LOCAL ANESTHETICS/

... ACT ON ANY PART OF NERVOUS SYSTEM & ON EVERY TYPE OF NERVE FIBER. /LOCAL ANESTHETICS/

Metabolism/Metabolites · 2 件

Primarily hepatic.

METABOLISM OF AMIDE-LINKED LOCAL ANESTHETICS IS MORE COMPLEX /THAN ESTER TYPES/ ...

FDA Pharmacological Classification · 6 件

L6JW2TJG99

DIBUCAINE

関連反応

0 件
反応記録を作成

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
85-79-0
PubChem CID
3025
DTXSID
DTXSID3045271
ChEMBL
CHEMBL1086
ChEBI
CHEBI:247956
UNII
L6JW2TJG99
EC Number
201-632-1
Nikkaji
J3.887C
· 4 件

99-101 °C (HCl salt)

64 °C

Melting point: 62-65 °C

99 - 101 °C (hydrochloride salt)

Physical DescriptionSolid
Stability/Shelf LifeSENSITIVE TO LIGHT
Dissociation Constants8.85

物理化学的性質

融点
64 ° · 64°
沸点
478.73 °C · 478.73°C (rough estimate)
比重(密度)
1.1145 · 1.1145 (rough estimate)
屈折率
1.63 · 1.6300 (estimate)
貯蔵温度
-20 °C · Store at -20°C
溶解性
45 · DMSO:45.0(Max Conc. mg/mL);131.02(Max Conc. mM)
酸解離定数(Pka)
-5.3 · pKa -5.3(aq. H2SO4) (Uncertain)
外見
Solid:particulate/powder
色
White to yellow
水溶解度
68.01 mg/L · 68.01mg/L(温度表記なし)
InChI
InChI=1S/C20H29N3O2/c1-4-7-14-25-19-15-17(16-10-8-9-11-18(16)22-19)20(24)21-12-13-23(5-2)6-3/h8-11,15H,4-7,12-14H2,1-3H3,(H,21,24)
InChIKey
PUFQVTATUTYEAL-UHFFFAOYSA-N
SMILES
N1C2C(=CC=CC=2)C(C(NCCN(CC)CC)=O)=CC=1OCCCC
LogP
4.4 at · 4.4 at 25℃ and pH7
CAS データベース
85 · 85-79-0(CAS DataBase Reference)
NISTの化学物質情報
Dibucaine(85-79-0)
Interactions · 2 件

... DURATION OF ACTION /OF SPINAL ANESTHESIA/ ... MAY BE INCREASED ... BY ADDING EPINEPHRINE TO THE SOLUTION. /LOCAL ANESTHETICS/

BY DECREASING THE RATE OF ABSORPTION, /EPINEPHRINE/ NOT ONLY LOCALIZES THE ANESTHETIC AT THE DESIRED SITE BUT ALSO ALLOWS THE RATE AT WHICH IT IS DESTROYED IN THE BODY TO KEEP PACE WITH THE RATE AT WHICH IT IS ABSORBED INTO THE CIRCULATION. THIS REDUCES ITS SYSTEMIC TOXICITY. /LOCAL ANESTHETICS/

Human Toxicity Excerpts · 2 件

DIBUCAINE HCL CAUSED PHOTOALLERGIC DERMATITIS IN 13-YR-OLD GIRL WHEN USED AS LOCAL ANESTHETIC IN TREATMENT OF DENTAL CARIES.

A 2-year-old child apparently ingested dibucaine hydrochloride (0.5% Nupercainal Cream), acted strangely, staggered, then seized, became cyanotic, vomited, developed a cardiorespiratory arrest, and died. /Dibucaine hydrochloride/

Effects During Pregnancy and Lactation◉ Summary of Use during Lactation
Non-Human Toxicity Values · 4 件

LD50 Mouse ip 24,500 ug/kg

LD50 Mouse sc 28,500 ug/kg

LD50 Rabbit sc 8500 ug/kg

LD50 Rabbit iv 2500 ug/kg

法規制情報

FDA Requirements · 1 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).

安全データ

rtecs
GD3150000
risk_code
22-41
hazard_code
Xn
safety_code
26-39
有毒物質データの
85-79-0(Hazardous Substances Data)

Established Pharmacologic Class [EPC] - Standardized Chemical Allergen

Physiologic Effects [PE] - Increased Histamine Release

Physiologic Effects [PE] - Cell-mediated Immunity

Chemical Structure [CS] - Allergens

MeSH Pharmacological Classification · 1 件

Drugs that block nerve conduction when applied locally to nerve tissue in appropriate concentrations. They act on any part of the nervous system and on every type of nerve fiber. In contact with a nerve trunk, these anesthetics can cause both sensory and motor paralysis in the innervated area. Their action is completely reversible. (From Gilman AG, et. al., Goodman and Gilman's The Pharmacological Basis of Therapeutics, 8th ed) Nearly all local anesthetics act by reducing the tendency of voltage-dependent sodium channels to activate.

Absorption, Distribution and Excretion · 5 件

In general, ionized forms (salts) of local anesthetics are not readily absorbed through intact skin. However, both nonionized (bases) and ionized forms of local anesthetics are readily absorbed through traumatized or abraded skin into the systemic circulation.

THE DRUG IS PARTIALLY METABOLIZED & A PORTION IS ELIMINATED UNCHANGED.

... RADIOACTIVE /SPINAL/ LOCAL ANESTHETICS ARE CONCN WITHIN SPINAL NERVE ROOTS AS WELL AS POSTERIOR & LATERAL COLUMNS OF SPINAL CORD. ... RATE OF ENZYMATIC HYDROLYSIS OF LOCAL ANESTHETIC AGENTS BY SPINAL FLUID IS SLOW. /LOCAL ANESTHETICS/

DURATION ... DEPENDS UPON RATE @ WHICH DRUG IS REMOVED FROM CEREBROSPINAL FLUID & FROM NERVE ROOTS WHERE IT EXERTS ITS ACTION. /LOCAL ANESTHETICS/

AT AUTOPSY, DIBUCAINE WAS DEMONSTRATED FROM UPPER SPINAL CORD (3.11 MUG/0.1 G), LOWER SPINAL CORD (7.15 MUG/0.1 G), LIVER (0.299 MUG/1.0 G) & KIDNEY (0.181 MUG/1.0 G).

Cellular LocationsCytoplasm
Metabolite PathwaysDibucaine Action Pathway

用途と製造

Uses · 4 件

MEDICATION (VET)

Therap cat: Anesthetic (local) /Hydrochloride/

Medicine (anesthetic)

Use (kg; approx.) in Germany (2009): >100

Methods of Manufacturing · 2 件

Miescher, US patent 1,825,623 (1931 to Ciba). /Dibucaine hydrochloride/

Quinoline derivative

Formulations/Preparations · 4 件

NUPERCAINAL (CIBA), TOPICAL: CREAM 0.5% WITH ACETONE SODIUM BISULFITE 0.37% IN 1.5 OZ CONTAINERS; OINTMENT 1% WITH ACETONE BISULFITE 0.5% IN 1 & 2 OZ CONTAINERS; AEROSOL SPRAY 0.25% WITH ALCOHOL 46% IN 6 OZ CONTAINERS; SUPPOSITORIES 2.5 MG /DIBUCAINE HCL/

BUCACET (LEMMON): EACH LOZENGE CONTAINS DIBUCAINE HCL 0.5 MG & CETALKONIUM CHLORIDE 4 MG. /DIBUCAINE HCL/

Grade: NF

Also available as the hydrochloride.

Use ClassificationPharmaceuticals
General Manufacturing Information · 2 件

A SPECTROPHOTOMETRIC TEST /FOR ATYPICAL CHOLINESTERASE/ WAS DEVELOPED BY KALOW & GENEST (1957) WHICH INCL DIBUCAINE AS AN INHIBITOR...MADE IT POSSIBLE TO IDENTIFY TYPE OF ESTERASE PRESENT IN TEST SERA...ALSO...TO DETECT HETEROZYGOUS CARRIERS OF /ATYPICAL ESTERASE/ TRAIT.

...toxicity resulted in its removal from the U.S. market as an injectable preparation ... It is currently available as a cream and an ointment for use on the skin.

応用分野 · 3 件

解説ジメチソキンとともにキノリン誘導体の合成局所麻酔薬である。ジブカインは，表面，浸潤，伝達，脊髄の各麻酔に使用される。水溶液は煮沸可能で，コカインのようには分解せず，コカインの約 12倍，プロカインの約 48倍の効力を示す。持続時間はコカインの約2倍，プロカインの約9倍である。毒性はコカインの5～9倍，プロカインの約 40倍である。血管分布の多い組織に注射したときや，誤って血管内に注射したときには，けいれん，振戦，血圧下降，心機能抑制，房室ブロック，心停止，過敏反応などを呈することもある。ブリタニカ国際大百科事典 小項目事典 ブリタニカ

使用Cinchocaine is a local anesthesic,used for Na+ channel blocker.

一般的な説明Articaine has a secondary nitrogen with a pKa of 7.8. It containsan aromatic thiophene ring bioisostere of the phenylring found in most other amide anesthetics. The log P of abenzene ring is 2.13 and the thiophene ring log P is 1.81,thus the thiophene ring is more hydrophilic than a phenylring. Although the thiophene ring has less lipid solubilitythan a phenyl ring, articaine is a lipid-soluble compound dueto the propylamine, the branched methyl and the substitutionson the thiophene ring. The onset of action of articaineis similar to lidocaine’s onset of action.

上流・下流製品情報

上流原料

N-(2-ジエチルアミノエチル)-2-クロロ-4-キノリンカルボキサミド1-ブタノール水酸化ナトリウムヘキサン

下流製品

ジブカイン塩酸塩

サプライヤー100 社

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補足説明 · 1 件

定義ChEBI: A monocarboxylic acid amide that is the 2-(diethylamino)ethyl amide of 2-butoxyquinoline-4-carboxylic acid. One of the most potent and toxic of the long-acting local anesthetics, its parenteral use was restricted to spinal anesthesia. It is now generally o ly used (usually as the hydrochloride) in creams and ointments and in suppositories for temporary relief of pain and itching associated with skin and anorectal conditions.