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Aminophylline structure
Aminophylline structure

Aminophylline

Iupac Name:1,3-dimethyl-7H-purine-2,6-dione;ethane-1,2-diamine
CAS No.: 317-34-0
Molecular Weight:420.42600
Modify Date.: 2022-04-01 06:58
Introduction: Aminophylline is a drug combination consisting of bronchodilator theophylline and ethylenediamine in 2: 1 ratio. It is a kind of non-selective adenosine receptor blocker, histone deacetylase activator and phosphodiesterase inhibition. It is mainly indicated for the treatment of various kinds of lung diseases including asthma, COPD, chronic bronchitis and emphysema. Aminophylline exerts its effect through the component of theophylline in vivo. Theophylline can relax the smooth muscle of the bronchial airways and pulmonary blood vessels. It can competitively inhibits type III and type IV phosphodiesterase (PDE), which breaks down cyclic AMP in smooth muscle cells, possibly leading to bronchodilation. Theophylline also binds to the adenosine A2B receptor to block the adenosine mediated bronchoconstriction. Furthermore, during the inflammatory states, theophylline can activate the histone deacetylase to prevent transcription of inflammatory genes that require the acetylation of histones to initiate the transcription. View more+
1. Names and Identifiers
1.1 Name
Aminophylline
1.2 Synonyms

(Theophylline)2 Ethylenediamine, Theophylline hemiethylenediamine complex, 3,7-Dihydro-1,3-dimethyl-1H-purine-2,6-dione, cmpd. with 1,2-ethanediamine (2:1) 1,2-Ethanediamine compd. with 3,7-Dihydro-1,3-dimethyl-1H-purine-2,6-dione (1:2) 1,3-diméthyl-3,7-dihydro-1H-purine-2,6-dione - éthane-1,2-diamine (2:1) 1,3-Dimethyl-3,7-dihydro-1H-purin-2,6-dion-ethan-1,2-diamin(2:1) 1,3-Dimethyl-3,7-dihydro-1H-purine-2,6-dione - 1,2-ethanediamine (2:1) 1,3-Dimethyl-3,7-dihydro-1H-purine-2,6-dione - ethane-1,2-diamine (2:1) 1,3-Dimethyl-3,9-dihydro-1H-purine-2,6-dione - ethane-1,2-diamine (2:1) 1H-Purine-2,6-dione, 3,7-dihydro-1,3-dimethyl-, compd. with 1,2-ethanediamine (2:1) 1H-purine-2,6-dione, 3,9-dihydro-1,3-dimethyl-, compd. with 1,2-ethanediamine (2:1) aminodur Aminophylline ethylenediamine Aminophylline hydrat AMinophylline(Phyllocontin, Truphylline) carena CaRine cariomin Cidophylline dobo EINECS 206-264-5 Ethylenediamine compd. with Theophylline (1:2) Etilen-Xantisan eufilina euufilin lasodex MFCD00013221 Novophyllin Novphyllin Pecram tefamin th/100 theomin THEOPHYLLINE COMPOUND WITH ETHYLENEDIAMINE Theophylline ethylenediamine Theophylline-e Theophylline-ethylenediaMine anhydrous COS Variaphylline LA

1.3 CAS No.
317-34-0
1.4 CID
9433
1.5 EINECS(EC#)
206-264-5
1.6 Molecular Formula
C16H24N10O4 (isomer)
1.7 Inchi
InChI=1S/2C7H8N4O2.C2H8N2/c2*1-10-5-4(8-3-9-5)6(12)11(2)7(10)13;3-1-2-4/h2*3H,1-2H3,(H,8,9);1-4H2
1.8 InChkey
FQPFAHBPWDRTLU-UHFFFAOYSA-N
1.9 Canonical Smiles
CN1C2=C(C(=O)N(C1=O)C)NC=N2.CN1C2=C(C(=O)N(C1=O)C)NC=N2.C(CN)N
1.10 Isomers Smiles
CN1C2=C(C(=O)N(C1=O)C)NC=N2.CN1C2=C(C(=O)N(C1=O)C)NC=N2.C(CN)N
2. Properties
3.1 Density
1.5140
3.1 Melting point
269-270 °C
3.1 Boiling point
454.1ºC at 760mmHg
3.1 Flash Point
454.1°Cat760mmHg
3.1 Precise Quality
420.19800
3.1 PSA
197.40000
3.1 logP
-1.77500
3.1 Solubility
H2O: 3.7?mg/mL solutions should be freshly prepared.
3.2 Appearance
white to slightly yellow powder or granular
3.3 Storage
Store at -20°C.
3.4 Chemical Properties
white to slightly yellowish powder
3.5 Color/Form
Powder
3.6 Contact Allergens
This drug is a 2:1 mixture of the alkaloid theophyllineand ethylenediamine (see below). It caused contactdermatitis in industrial plants, pharmacists, and nurses.Ethylenediamine is the sensitizer and patch testing isgenerally positive to both ethylenediamine and aminophyllineand negative to theophylline.
3.7 pKa
pKa 5.0 (Uncertain)
3.8 Water Solubility
soluble
3.9 Stability
Stable under normal temperatures and pressures. Absorbs carbon dioxide from the air. Unstable in acid solution.
3.10 StorageTemp
Inert atmosphere,Store in freezer, under -20°C
3. Use and Manufacturing
4.1 Usage
Bronchodilatator;Mastocytes degranulation inhibitor
4. Safety and Handling
5.1 Symbol
GHS06
5.1 Hazard Codes
C
5.1 Signal Word
Danger
5.1 Risk Statements
R22; R34; R42/43
5.1 Safety Statements
S45-S36/37/39-S26-S23
5.1 Packing Group
III
5.1 Hazard Class
6.1(b)
5.1 Hazard Declaration
H301
5.1 RIDADR
UN 2811 6.1/PG 3
5.1 Caution Statement
P301 + P310
5.1 WGK Germany
3
5.1 RTECS
XH5600000
5.1 Toxicity

CHEMICAL IDENTIFICATION

RTECS NUMBER :
XH5600000
CAS REGISTRY NUMBER :
317-34-0
LAST UPDATED :
199701
DATA ITEMS CITED :
35
MOLECULAR FORMULA :
C7-H8-N4-O2.1/2C2-H8-N2
MOLECULAR WEIGHT :
210.25
WISWESSER LINE NOTATION :
T56 BM DN FNVNVJ F H & 2 &621 &Z2Z &622

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Human - man
DOSE/DURATION :
1420 ug/kg
TOXIC EFFECTS :
Cardiac - other changes Lungs, Thorax, or Respiration - other changes
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - infant
DOSE/DURATION :
7595 mg/kg/5D-I
TOXIC EFFECTS :
Behavioral - convulsions or effect on seizure threshold Gastrointestinal - hypermotility, diarrhea
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - man
DOSE/DURATION :
19 mg/kg/3D
TOXIC EFFECTS :
Behavioral - withdrawal Gastrointestinal - nausea or vomiting
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - woman
DOSE/DURATION :
120 mg/kg
TOXIC EFFECTS :
Endocrine - hyperglycemia Nutritional and Gross Metabolic - changes in potassium Nutritional and Gross Metabolic - metabolic acidosis
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Human
DOSE/DURATION :
139 mg/kg/7D-C
TOXIC EFFECTS :
Behavioral - muscle contraction or spasticity Behavioral - coma Cardiac - arrhythmias (including changes in conduction)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Rectal
SPECIES OBSERVED :
Human - child
DOSE/DURATION :
39 mg/kg/8H
TOXIC EFFECTS :
Behavioral - coma Gastrointestinal - nausea or vomiting Nutritional and Gross Metabolic - dehydration
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Rectal
SPECIES OBSERVED :
Human - child
DOSE/DURATION :
221 mg/kg/3D
TOXIC EFFECTS :
Behavioral - convulsions or effect on seizure threshold Gastrointestinal - nausea or vomiting Nutritional and Gross Metabolic - body temperature increase
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
243 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
129 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
176 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
104 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intramuscular
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
167 mg/kg
TOXIC EFFECTS :
Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - respiratory stimulation Gastrointestinal - changes in structure or function of salivary glands
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
150 mg/kg
TOXIC EFFECTS :
Behavioral - convulsions or effect on seizure threshold
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
37 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
186 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
125 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intramuscular
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
215 mg/kg
TOXIC EFFECTS :
Behavioral - tremor Behavioral - convulsions or effect on seizure threshold
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Unreported
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
350 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
200 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
150 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Rectal
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
200 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rabbit
DOSE/DURATION :
330 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rabbit
DOSE/DURATION :
150 mg/kg
TOXIC EFFECTS :
Behavioral - convulsions or effect on seizure threshold
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - guinea pig
DOSE/DURATION :
184 mg/kg
TOXIC EFFECTS :
Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - respiratory stimulation Gastrointestinal - changes in structure or function of salivary glands
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - guinea pig
DOSE/DURATION :
130 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - guinea pig
DOSE/DURATION :
222 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - guinea pig
DOSE/DURATION :
143 mg/kg
TOXIC EFFECTS :
Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - respiratory stimulation Gastrointestinal - changes in structure or function of salivary glands
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
2400 mg/kg/12D-I
TOXIC EFFECTS :
Nutritional and Gross Metabolic - weight loss or decreased weight gain Related to Chronic Data - death
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
200 mg/kg/8D-I
TOXIC EFFECTS :
Blood - changes in serum composition (e.g. TP, bilirubin, cholesterol) Immunological Including Allergic - increase in humoral immune response
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
175 mg/kg/7D-I
TOXIC EFFECTS :
Immunological Including Allergic - decrease in cellular immune response

MUTATION DATA

TYPE OF TEST :
Cytogenetic analysis
TEST SYSTEM :
Rodent - mouse Mammary gland
DOSE/DURATION :
500 mg/L/24H (Continuous)
REFERENCE :
JTSCDR Journal of Toxicological Sciences. (Japanese Soc. of Toxicological Sciences, 4th Floor, Gakkai Center Bldg., 4-16, Yayoi 2-chome, Bunkyo-ku, Tokyo 113, Japan) V.1- 1976- Volume(issue)/page/year: 5,141,1980 *** OCCUPATIONAL EXPOSURE LIMITS *** OEL-RUSSIA:STEL 0.5 mg/m3 JAN 1993 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOHS - National Occupational Hazard Survey (1974) NOHS Hazard Code - 84313 No. of Facilities: 2405 (estimated) No. of Industries: 4 No. of Occupations: 18 No. of Employees: 10320 (estimated) NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - 84313 No. of Facilities: 724 (estimated) No. of Industries: 5 No. of Occupations: 16 No. of Employees: 37320 (estimated) No. of Female Employees: 28051 (estimated)
5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Acute toxicity - Oral, Category 3

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word

Danger

Hazard statement(s)

H301 Toxic if swallowed

Precautionary statement(s)
Prevention

P264 Wash ... thoroughly after handling.

P270 Do not eat, drink or smoke when using this product.

Response

P301+P310 IF SWALLOWED: Immediately call a POISON CENTER/doctor/\u2026

P321 Specific treatment (see ... on this label).

P330 Rinse mouth.

Storage

P405 Store locked up.

Disposal

P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

6. Synthesis Route
7. Precursor and Product
precursor:
58-55-9
58-55-9
8. Other Information
8.0 Merck
14,465
8.1 Description
Aminophylline is a drug combination consisting of bronchodilator theophylline and ethylenediamine in 2: 1 ratio. It is a kind of non-selective adenosine receptor blocker, histone deacetylase activator and phosphodiesterase inhibition. It is mainly indicated for the treatment of various kinds of lung diseases including asthma, COPD, chronic bronchitis and emphysema. Aminophylline exerts its effect through the component of theophylline in vivo. Theophylline can relax the smooth muscle of the bronchial airways and pulmonary blood vessels. It can competitively inhibits type III and type IV phosphodiesterase (PDE), which breaks down cyclic AMP in smooth muscle cells, possibly leading to bronchodilation. Theophylline also binds to the adenosine A2B receptor to block the adenosine mediated bronchoconstriction. Furthermore, during the inflammatory states, theophylline can activate the histone deacetylase to prevent transcription of inflammatory genes that require the acetylation of histones to initiate the transcription.
8.2 References
https://www.drugbank.ca/drugs/DB01223 https://en.wikipedia.org/wiki/Aminophylline
8.3 Description
Aminophylline is a 2/1 mixture of theophylline and ethylenediamine. It caused contact dermatitis in industrial plants, in pharmacists, and in nurses. Ethylenediamine is the sensitizer, and patch testing is generally positive to both ethylenediamine and aminophylline, but negative to theophylline.
8.4 Chemical Properties
white to slightly yellowish powder
8.5 Originator
Memcophylline,Memphis Co.
8.6 Uses
Bronchodilatator;Mastocytes degranulation inhibitor
8.7 Uses
Aminophylline is a bronchodilator and a non-selective phosphodiesterase (PDE) inhibitor.
8.8 Manufacturing Process
A mixture of 198 g (1 mol) theophylline and 60-78 g (0.75-1 mol) ethylenediamine hydrate in 300 g of water was stirred at 50°C and then the mixture was concentrated in vacuo. The product (aminophylline) was separeted by suction filtration. Aminophylline was used as an aqueous solution.
8.9 Brand name
Phyllocontin (Purdue Frederick); Somophyllin (Fisons); Truphylline (G & W);Afonilum;Aminomal;Aminophylline injection;Aminophylline mudrane;Aminophylline oral;Amino-slow;Amnivent;Asmafilin;Cardophylline;Carine;Colonofilin;Corfilamine;Corophylline;Corphyllamin;Duraphyllin;Escophylline;Eudiamine;Euphyllin 0.48;Euphyllin retard;Euphylllin cr;Euphylllina;Fadfilina;Godafilin;Jaa aminophylline;Mini-lix;Mudrane gg;Mundiphyllin;Palaran;Palaron;Pecram;Pecran;Peterphylin;Phyllotemp;Planphylline;Somophyllin-12;Syntophyllin;Teophyllamin;Thodrox;Variaphylline.
8.10 Therapeutic Function
Diuretic, Cardiac stimulant, Smooth muscle relaxant, Vasodilator
8.11 World Health Organization (WHO)
Aminophylline, the ethylenediamine salt of theophylline, was introduced many years ago as a treatment for asthma and is listed in the 8th WHO Model List of Essential Drugs. It has been recognized for some 10 years that aminophylline preparations are not interchangeable because bioavailability can vary considerably. The resulting variability in drug absorption can lead to adverse effects including irritation of the mucosa. Allergic reation can also be an adverse effect of aminophylline. Theophylline functions similarly but is considered less of an irritant.
8.12 Hazard
Cardiovascular and respiratory collapse.
8.13 Contact allergens
This drug is a 2:1 mixture of the alkaloid theophylline and ethylenediamine (see below). It caused contact dermatitis in industrial plants, pharmacists, and nurses. Ethylenediamine is the sensitizer and patch testing is generally positive to both ethylenediamine and aminophylline and negative to theophylline.
8.14 Veterinary Drugs and Treatments
The theophyllines are used primarily for their bronchodilatory effects, often in patients with myocardial failure and/or pulmonary edema. While they are still routinely used, the methylxanthines must be used cautiously due to their adverse effects and toxicity.
8.15 Usage
Aminophylline exhibits vasodilatory and anti-inflammatory activity and is occasionally clinically used to treat chronic obstructive pulmonary disorder (COPD). In animal models of allergen-induced lung inflammation, aminophylline decreases levels of IL-5, IL-8, and eosinophils. It is mostly used to prepare solutions for intravenous injections.
9. Computational chemical data
  • Molecular Weight: 420.42600g/mol
  • Molecular Formula: C16H24N10O4
  • Compound Is Canonicalized: True
  • XLogP3-AA: null
  • Exact Mass: 420.19819929
  • Monoisotopic Mass: 420.19819929
  • Complexity: 273
  • Rotatable Bond Count: 1
  • Hydrogen Bond Donor Count: 4
  • Hydrogen Bond Acceptor Count: 8
  • Topological Polar Surface Area: 191
  • Heavy Atom Count: 30
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count: 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Isotope Atom Count: 0
  • Covalently-Bonded Unit Count: 3
  • CACTVS Substructure Key Fingerprint: AAADceB7+AAAAAAAAAAAAAAAAAAAAWLAAAAsWAAAAAAAAFgB4AAAHgAQAAAACAjBlgQHsBfJkACoAQdxdACAgC2XEKABUYGoVECASAhASCAUAIgIFyJAAGAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==
11. Realated Product Infomation