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ジプロフィリン

Diprophylline

HCID 3182
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
479-18-5
標準SMILES
Cn1c(=O)c2c(ncn2CC(O)CO)n(C)c1=O
InChIKey
KSCFJBIXMNOVSH-UHFFFAOYSA-N
分子式
C10H14N4O4
平均分子量
254.24 g/mol
単同位体質量
254.10150494

概要

Dyphylline is an oxopurine that is theophylline bearing a 2,3-dihydroxypropyl group at the 7 position. It has broncho- and vasodilator properties, and is used in the treatment of asthma, cardiac dyspnea, and bronchitis. It is also an ingredient in preparations that have been promoted for coughs. It has a role as a bronchodilator agent, a vasodilator agent, an EC 3.1.4.* (phosphoric diester hydrolase) inhibitor and a muscle relaxant. It is an oxopurine and a member of propane-1,2-diols.

名称と識別子

優先名称
Diprophylline
IUPAC
7-(2,3-dihydroxypropyl)-1,3-dimethylpurine-2,6-dione
現地名
ジプロフィリン
英語名
Diprophylline
分子式
C10H14N4O4
分子量
254.24

名称と別名

dyphyllineDiprophylline479-18-57-(2,3-Dihydroxypropyl)theophyllineDiphyllineGlyphyllineCorphyllinNeutrafillinaNeutraphyllineNeutroxantinaProtheophyllineSynthophylline
名称をさらに表示
7-(2,3-ジヒドロキシプロピル)テオフィリン7-(2,3-ジヒドロキシプロピル)-1,3-ジメチルキサンチンジプロフィリン7‐(2,3‐ジヒドロキシプロピル)テオフィリンディフィリンダイフィリンジプロフィリン (JAN)DIPHYLLINDihydroxypropylDilordihydroxypropyltheophyllineTeofenCircainNeophyl
GlyfyllinGlyphyllinHyphyllineNeophyllinHidroxiteofillinaAstrophyllinCoronarinHiphyllin

データベース識別子

CAS
479-18-5
PubChem CID
3182
DTXSID
DTXSID6022975
ChEMBL
CHEMBL1752

物性

構造計算による物性

XLogP
-1.8
極性表面積
98.9 Ų
水素結合供与体数
2
水素結合受容体数
5
回転可能結合数
3
重原子数
18
形式電荷
0
複雑度
364

実験および物理化学的性質

DrugsPharmaceuticals -> Brochodilators
pH(1% AQ SOLN) 6.6 TO 7.3
LogP · 2 件

-1.9

-1.25

TasteEXTREME BITTER TASTE
Color/Form · 2 件

CRYSTALS FROM ALCOHOL

WHITE AMORPHOUS SOLID

Solubility · 4 件

FREELY SOL IN WATER; 1 G IN 3 ML H2O @ 25 °C

SOL IN ALC: 2 G/100 ML; IN CHLOROFORM: 1 G/100 ML

1.43e+01 g/L

>38.1 [ug/mL] (The mean of the results at pH 7.4)

Human Drugs · 4 件

Breast Feeding; Lactation; Milk, Human; Anti-Asthmatic Agents; Bronchodilator Agents

FDA approved drugs -> Active ingredient

FDA approved drugs -> Active ingredient

Pharmaceuticals

Melting Point · 3 件

155-157

158 °C

161.5 °C

Physical DescriptionSolid
Stability/Shelf LifeIS STABLE IN GASTRIC JUICE

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 · 6 件

Warning

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

P261, P264, P270, P271, P301+P317, P304+P340, P317, P330, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 61 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Danger

H302: Harmful if swallowed [Warning Acute toxicity, oral]

危険有害性情報

Other Safety InformationIMAP assessments - 1H-Purine-2,6-dione, 7-(2,3-dihydroxypropyl)-3,7-dihydro-1,3-dimethyl-: Environment tier I assessment
Hazard Classes and Categories · 2 件

Acute Tox. 4 (100%)

Acute toxicity (Oral) - Category 4

毒性情報

Interactions · 2 件

METHYLXANTHINES CAN ALSO ANTAGONIZE EFFECTS OF HYPOPROTHROMBINEMIA CAUSED BY COUMARIN DERIV... /METHYLXANTHINES/

XANTHINES CAN MARKEDLY POTENTIATE CARDIAC INOTROPIC RESPONSES TO BETA-ADRENERGIC AGONISTS & TO GLUCAGON. /XANTHINES/

Human Toxicity Excerpts · 3 件

PARENTERALLY ADMIN THEOPHYLLINE...INCR RATE & DEPTH OF RESP... AFTER ADMIN OF LARGE AMT OF...THEOPHYLLINE, ENTIRE CNS, INCL SPINAL CORD, IS STIMULATED. REFLEX EXCITABILITY IS INCR, & LOWER MOTOR CENTERS MAY BE DIRECTLY EXCITED. /THEOPHYLLINE/

THEOPHYLLINE...CAN BE QUITE TOXIC & HAS OCCASIONALLY PROVED FATAL. /THEOPHYLLINE/

GREAT CARE...MUST BE EXERCISED WHEN /SALTS OF XANTHINES/...ARE ADMIN /IV/... ESP IN PT WITH SEVERE MYOCARDIAL DAMAGE, FOR HIGH LOCAL CONCN MAY RESULT IN PPT OF FREE ALKALOIDS WHEN SALTS ARE EXPOSED TO PH OF BLOOD. ...SHARP, USUALLY TRANSIENT, FALL IN BLOOD PRESSURE...WHEN INJECTION IS TOO RAPID. /XANTHINE SALTS/

化学と産業

薬理情報

ATC Code · 2 件

R - Respiratory system

QR - Respiratory system

Protein Binding84%
Pharmacodynamics · 1 件

Dyphylline, a xanthine derivative, is a bronchodilator used for relief of acute bronchial asthma and for reversible bronchospasm associated with chronic bronchitis and emphysema. Dyphylline is a xanthine derivative with pharmacologic actions similar to theophylline and other members of this class of drugs. Its primary action is that of bronchodilation, but it also exhibits peripheral vasodilatory and other smooth muscle relaxant activity to a lesser degree.

Mechanism of Action · 5 件

The bronchodilatory action of dyphylline, as with other xanthines, is thought to be mediated through competitive inhibition of phosphodiesterase with a resulting increase in cyclic AMP producing relaxation of bronchial smooth muscle as well as antagonism of adenosine receptors.

THEIR MOST IMPORTANT ACTION...IS THEIR ABILITY TO RELAX SMOOTH MUSCLES OF BRONCHI... THEOPHYLLINE IS MOST EFFECTIVE... /THEOPHYLLINE/

ACTION OF XANTHINES ON MOTOR ACTIVITY OF GI TRACT... DILUTE SOLN INCR, & HIGH CONCN DEPRESS, TONE & STRENGTH OF CONTRACTION OF ISOLATED INTESTINAL STRIPS. /XANTHINES/

...ACTION SEEMS TO RESULT FROM INCR IN CONCN OF FACTOR V (AC-GLOBULIN) IN PLASMA WHICH, IN TURN, MAY BE CAUSED BY INCR IN PLASMA CONCN OF FREE FATTY ACIDS PRODUCED...THERE ARE ALSO INCR IN CONCN OF CIRCULATING PROTHROMBIN & FIBRINOGEN. /XANTHINES/

...ACCOMPANYING DECR IN VENOUS FILLING PRESSURE, WHICH IS CAUSED @ LEAST PARTLY BY MORE COMPLETE EMPTYING OF HEART. /THEOPHYLLINE/

Biological Half-Life2 hours (range 1.8 - 2.1 hours)
Metabolism/Metabolites · 2 件

Hepatic

IN BODY XANTHINES ARE ONLY PARTIALLY DEMETHYLATED & OXIDIZED. THEY ARE LARGELY EXCRETED AS METHYLURIC ACIDS OR AS METHYLXANTHINES. /XANTHINES/

MeSH Pharmacological Classification · 3 件

関連反応

2 件
反応記録を作成
HRID 666511 の反応式
HRID 666511反応物としてTraining data from https://doi.org/10.1039/C8SC04228D (3/10)
HRID 1287239 の反応式
HRID 1287239反応物としてuspto-grants-1976_10

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
ChEBI
CHEBI:4728
UNII
263T0E9RR9
EC Number
207-526-1
Nikkaji
J2.054K
Collision Cross Section · 2 件

152.6 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

151.82 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

物理化学的性質

融点
161 · 161-162 °C(lit.)
沸点
397.46 °C · 397.46°C (rough estimate)
比重(密度)
1.3036 · 1.3036 (rough estimate)
屈折率
1.62 · 1.6200 (estimate)
貯蔵温度
Keep in dark place,Inert atmosphere,Room temperature
溶解性
96 %)。 · 水に溶けやすく、エタノールに溶けにくい(96%)。
酸解離定数(Pka)
13.74 · 13.74±0.20(Predicted)
外見
粉
色
白い
水溶解度
33 g/100mL · 33g/100mL(25℃)
Merck
14 · 14,3479
BRN
284563 · 284563
安定性
Hygroscopic
化粧品成分の機能
スキンコンディショニング
InChI
1S/C10H14N4O4/c1-12-8-7(9(17)13(2)10(12)18)14(5-11-8)3-6(16)4-15/h5-6,15-16H,3-4H2,1-2H3
InChIKey
KSCFJBIXMNOVSH-UHFFFAOYSA-N
SMILES
CN1C(=O)N(C)c2ncn(CC(O)CO)c2C1=O
LogP
-1.1 · -1.100 (est)
CAS データベース
479 · 479-18-5(CAS DataBase Reference)
NISTの化学物質情報
Dyphylline(479-18-5)
EPAの化学物質情報
Dyphylline (479-18-5)

化学的性質

化学的特性white to light yellow crystal powder

Drug Induced Liver Injury · 6 件

Drug Induced Liver Injury Rank (DILIrank 2.0)

Dyphylline

vNo-DILI-concern

0

No match

DOI:10.1016/j.drudis.2016.02.015

Effects During Pregnancy and Lactation◉ Summary of Use during Lactation

安全データ

wgk
3
tsca
TSCA listed
rtecs
XH5100000
毒性
LD50 in mice (mg/kg): 3400 orally; 1430 s.c. (Al'tshuler)
hs_code
29395900
risk_code
22-36/37/38
hazard_code
Xn,Xi
safety_code
36-36/37-26
Hazard Classifications
Acute Tox. 4 Oral
ストレージクラス
11 - Combustible Solids
有毒物質データの
479-18-5(Hazardous Substances Data)

Agents that cause an increase in the expansion of a bronchus or bronchial tubes.

Compounds which inhibit or antagonize the biosynthesis or actions of phosphodiesterases.

Drugs used to cause dilation of the blood vessels.

Absorption, Distribution and Excretion · 6 件

Dyphylline exerts its bronchodilatory effects directly and, unlike the­ophylline, is excreted unchanged by the kidneys without being metabolized by the liver. Approximately 88% of a single oral dose can be recovered from the urine unchanged.

...RAPID RATE OF DISPOSITION.

IT MAY BE MORE CONSISTENTLY ABSORBED FROM GI TRACT & LESS IRRITATING THAN THEOPHYLLINE & AMINOPHYLLINE.

SINGLE DYPHYLLINE DOSE WAS GIVEN TO 5 NORMAL VOLUNTEERS. DOSES OF 19-27 MG/KG RESULTED IN PEAK SERUM CONCN OF 19.3-23.5 MUG/ML & WERE TOLERATED WELL BY 4 SUBJECTS. 1 HAD SEVERE HEADACHE AFTER 28 MG/KG DOSE ASSOC WITH 36.4 MUG/ML; WAS NOT METABOLIZED TO THEOPHYLLINE.

IN 5 NORMAL VOLUNTEERS MEAN T/2 WAS 1.8 HR; MEAN TOTAL BODY CLEARANCE RATE & MEAN RENAL CLEARANCE RATE WERE 333 & 276 ML/MIN, RESPECTIVELY. MEAN VOL OF DISTRIBUTION WAS 0.8 L/KG. IN URINE 83% OF DOSE WAS EXCRETED UNCHANGED & THEOPHYLLINE WAS NOT DETECTED.

For more Absorption, Distribution and Excretion (Complete) data for DYPHYLLINE (6 total), please visit the HSDB record page.

Cellular LocationsCytoplasm

用途と製造

UsesMEDICATION
Methods of ManufacturingJONES, MANEY, US PATENT 2,575,344 (1951 TO STATE UNIV OF IOWA): ROTH ARCH PHARM 292, 234 (1959)
Formulations/Preparations · 2 件

TABLETS (200 MG), ELIXIR (100 MG/15 ML), & AMPULS (500 MG/2 ML) ARE AVAIL.

ORAL: ELIXIR 100 MG/15 ML; TABLETS 200 MG; TABLETS (TIMED-RELEASE) 400 MG. ... ELIXIR 160 MG/15 ML; TABLETS 200 & 400 MG. INJECTION: SOLN 250 MG/ML IN 2 & 10 ML CONTAINERS.

Use ClassificationPharmaceuticals
General Manufacturing Information1H-Purine-2,6-dione, 7-(2,3-dihydroxypropyl)-3,7-dihydro-1,3-dimethyl-: ACTIVE
応用分野 · 4 件

用途医薬品:気管支拡張剤、血管拡張剤

用途ホスホジエステラーゼ阻害作 用を示します。

説明Dyphylline is the N-7 dihydroxypropyl derivative of theophylline and is not a theophylline salt. Dyphylline does not get metabolized to theophylline in vivo, and even though it contains 70% theophylline by molecular weight ratio, the equivalent amount to theophylline is not known. Dosing must be accomplished independently by monitoring dyphylline blood levels. Dyphylline has a diminished bronchodilator effect compared to theophylline, but it may have lower and less serious side effects. Dosage forms available are an elixir and tablets.

使用PDE inhibitor, bronchodilator, vasodilator

上流・下流製品情報

上流原料

2,3-プロパンジオールSodium Theophylline(1,3-Dimethyl-2,6-dione-purine-Na)1-クロロ-2,5-ジメチル-4-ニトロベンゼン水酸化ナトリウムテオフィリン1,3-ジメチル-7-(オキシラニルメチル)-1,2,3,6-テトラヒドロ-7H-プリン-2,6-ジオン1,3-dimethyl-7-prop-2-enyl-purine-2,6-dione3-ブロモプロパン-1,2-ジオール3-アミノ-1,2-プロパンジオール

下流製品

Theophylline Impurity 1

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補足説明 · 1 件

定義ChEBI: An oxopurine that is theophylline bearing a 2,3-dihydroxypropyl group at the 7 position. It has broncho- and vasodilator properties, and is used in the treatment of asthma, cardiac dyspnea, and bronchitis. It is also an ingredient in preparations that have been promoted for coughs.