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디프로필린

Diprophylline

HCID 3182
노트반응
기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
부분 구조 검색유사 구조 찾기

기본 정보

CAS
479-18-5
표준 SMILES
Cn1c(=O)c2c(ncn2CC(O)CO)n(C)c1=O
InChIKey
KSCFJBIXMNOVSH-UHFFFAOYSA-N
분자식
C10H14N4O4
평균 분자량
254.24 g/mol
단동위원소 질량
254.10150494

개요

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.

이름 및 식별자

우선 이름
Diprophylline
IUPAC
7-(2,3-dihydroxypropyl)-1,3-dimethylpurine-2,6-dione
현지명
디프로필린
영어명
Diprophylline
분자식
C10H14N4O4
분자량
254.24

이름 및 동의어

dyphyllineDiprophylline479-18-57-(2,3-Dihydroxypropyl)theophyllineDiphyllineGlyphyllineCorphyllinNeutrafillinaNeutraphyllineNeutroxantinaProtheophyllineSynthophylline
이름 더 보기
디프로필린디필린DIPHYLLINDihydroxypropylDilordihydroxypropyltheophyllineTeofenCircainNeophyl
GlyfyllinGlyphyllinHyphyllineNeophyllinHidroxiteofillinaAstrophyllinCoronarinHiphyllin

데이터베이스 식별자

CAS
479-18-5
PubChem CID
3182
DTXSID
DTXSID6022975
ChEMBL
CHEMBL1752
ChEBI
CHEBI:4728
UNII
263T0E9RR9
EC Number
207-526-1
Nikkaji
J2.054K

물성

구조 계산 물성

XLogP
-1.8
극성 표면적
98.9 Ų
수소 결합 공여자 수
2
수소 결합 수용자 수
5
회전 가능 결합 수
3
무거운 원자 수
18
형식 전하
0
복잡도
364

실험 및 물리화학적 성질

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

-1.9

-1.25

TasteEXTREME BITTER TASTE
Color/Form · 2건

CRYSTALS FROM ALCOHOL

WHITE AMORPHOUS SOLID

Solubility · 4건

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 · 4건

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

FDA approved drugs -> Active ingredient

FDA approved drugs -> Active ingredient

Pharmaceuticals

Melting Point · 3건

155-157

158 °C

161.5 °C

Physical DescriptionSolid
Stability/Shelf LifeIS STABLE IN GASTRIC JUICE

안전 및 규제

안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.

GHS 분류

GHS Classification · 6건

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]

유해성 정보

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 · 2건

Acute Tox. 4 (100%)

Acute toxicity (Oral) - Category 4

독성 정보

Interactions · 2건

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 · 3건

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/

화학 및 산업

약리 정보

ATC Code · 2건

R - Respiratory system

QR - Respiratory system

Protein Binding84%
Pharmacodynamics · 1건

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 · 5건

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 · 2건

Hepatic

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

MeSH Pharmacological Classification · 3건

관련 반응

2건
반응 기록 만들기
HRID 666511 반응식
HRID 666511반응물로Training data from https://doi.org/10.1039/C8SC04228D (3/10)
HRID 1287239 반응식
HRID 1287239반응물로uspto-grants-1976_10

화합물 노트

불러오는 중…

이 페이지에서기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
Collision Cross Section · 2건

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]

물리화학적 성질

녹는점
161 · 161-162 °C(lit.)
끓는 점
397.46 °C · 397.46°C (rough estimate)
밀도
1.3036 · 1.3036 (rough estimate)
굴절률
1.62 · 1.6200 (estimate)
저장 조건
Keep in dark place,Inert atmosphere,Room temperature
용해도
물에는 잘 녹고, 에탄올에는 약간 녹습니다(96%).
산도 계수 (pKa)
13.74 · 13.74±0.20(Predicted)
물리적 상태
가루
색상
하얀색
수용성
33 g/100mL · 33g/100mL(25℃)
Merck
14 · 14,3479
BRN
284563 · 284563
안정성
흡습성
화장품 원료 기능
피부 컨디셔닝
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)
NIST
Dyphylline(479-18-5)
EPA
Dyphylline (479-18-5)

화학적 성질

white to light yellow crystal powder

Drug Induced Liver Injury · 6건

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

안전 데이터

wgk
3
tsca
TSCA listed
rtecs
XH5100000
독성
LD50 in mice (mg/kg): 3400 orally; 1430 s.c. (Al'tshuler)
HS 번호
29395900
risk_code
22-36/37/38
hazard_code
Xn,Xi
safety_code
36-36/37-26
기존화학 물질
KE-10863
Hazard Classifications
Acute Tox. 4 Oral
스토리지 클래스
11 - Combustible Solids
유해 물질 데이터
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 · 6건

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

용도 및 제조

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

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
응용 분야 · 2건

개요Dyphylline 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.

용도PDE inhibitor, bronchodilator, vasodilator

상·하류 제품 정보

상류 원료

프로필렌 글리콜Sodium Theophylline(1,3-Dimethyl-2,6-dione-purine-Na)1-Chloro-2,5-dimethyl-4-nitrobenzene2-chloro-5-nitro-p-xylene수산화나트륨테오필린1,3-Dimethyl-7-(oxiran-2-ylmethyl)-2,3,6,7-tetrahydro-1H-purine-2,6-dione1,3-dimethyl-7-prop-2-enyl-purine-2,6-dione3-Bromo-1,2-propanediol3-아미노-1,2-프로판디올

하류 제품

테오필린불순물1

공급사100 곳

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추가 설명 · 1건

정의ChEBI: 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.