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58-55-9 molecular structure
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1,3-dimethyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione

ChemBase ID: 162
Molecular Formular: C7H8N4O2
Molecular Mass: 180.16402
Monoisotopic Mass: 180.06472552
SMILES and InChIs

SMILES:
O=c1n(c(=O)n(c2nc[nH]c12)C)C
Canonical SMILES:
Cn1c(=O)n(C)c2c(c1=O)[nH]cn2
InChI:
InChI=1S/C7H8N4O2/c1-10-5-4(8-3-9-5)6(12)11(2)7(10)13/h3H,1-2H3,(H,8,9)
InChIKey:
ZFXYFBGIUFBOJW-UHFFFAOYSA-N

Cite this record

CBID:162 http://www.chembase.cn/molecule-162.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
1,3-dimethyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione
1,3-dimethyl-2,3,6,9-tetrahydro-1H-purine-2,6-dione
IUPAC Traditional name
theophylline
constant-T
Brand Name
Accurbron
Acet-Theocin
Aerobin
Aerolate
Aerolate III
Aerolate SR
Afonilm
Afonilum
Aquaphyllin
Armophylline
Asbron
Asmalix
Asmax
Austyn
Bilordyl
Bronchoretard
Bronkodyl
Bronkodyl SR
Cetraphylline
Choledyl SA
Chronophyllin
Constant T
Diffumal
Diphyllin
Doraphyllin
Duraphyl
Duraphyllin
Dyspne-Inhal
Egifilin
Elan
Elixex
Elixicon
Elixomin
Elixophyllin
Elixophyllin SR
Elixophylline
Etheophyl
Euphyllin
Euphylline
Euphylong
Labid
Lanophyllin
Lasma
Liquophylline
Liquorice
Maphylline
Medaphyllin
Nuelin
Optiphyllin
Parkophyllin
Physpan
Pro-Vent
Pulmidur
Pulmo-Timelets
Quibron
Quibron T
Quibron T/SR
Quibron-T
Quibron-T/SR
Respbid
Respicur
Respid
Slo-Bid
Slo-Phyllin
Solosin
Somophyllin CRT
Somophyllin T
Somophyllin-CRT
Somophyllin-DF
Somophyllin-T
Spophyllin Retard
Sustaire
Synophylate
Synophylate-L.A. Cenules
T-Phyl
Talotren
Tefamin
Telb-DS
Telbans Dry Syrup
Teocen 200
Teofilina
Teofyllamin
Teolair
Teonova
Teosona
Tesona
Theacitin
Theal Tablets
Theo 24
Theo-11
Theo-24
Theo-DS
Theo-Dur
Theo-Nite
Theo-Sav
Theobid
Theobid Duracap
Theobid Jr.
Theochron
Theocin
Theoclair-SR
Theoclear
Theoclear 80
Theoclear L.A.-130
Theoclear LA
Theoclear-200
Theoclear-80
Theocontin
Theodel
Theodrip
Theodur Dry Syrup
Theofol
Theograd
Theolair
Theolair-SR
Theolix
Theolixir
Theon
Theona P
Theopek
Theophyl
Theophyl-225
Theophyl-SR
Theophylline-SR
Theoplus
Theospan
Theostat
Theostat 80
Theotard
Theovent
Uni-Dur
Unifyl
Unilong
Uniphyl
Uniphyllin
Xanthium
Xantivent
Synonyms
Dimethylxanthine
Theophyline
Theophyllin
Theophylline aminoacetate
Pseudotheophylline
Theophylline Anhydrous
Theophylline
Theo-Dur
1,3-Dimethylxanthine
2,6-Dihydroxy-1,3-dimethylpurine
3,7-Dihydro-1,3-dimethyl-1H-purine-2,6-dione
THEOPHYLLINE ANHYDROUS
Theophylline
3,9-Dihydro-1,3-dimethyl-1H-purine-2,6-dione
3,7-Dihydro-1,3-dimethyl- 1H-purine-2,6-dione
Accurbron
Aerobin
Armophylline
Asmax
Bronkodyl
Theophyl
Theoplus
Theostat
Unifyl
Unilong
Xanthium
1,3-DIMETHYLXANTHINE
Theophylline
CAS Number
58-55-9
EC Number
200-385-7
MDL Number
MFCD00079619
Beilstein Number
13463
PubChem SID
160963625
46505949
24277677
PubChem CID
2153
CHEBI ID
28177
ATC CODE
R03DA04
CHEMBL
190
Chemspider ID
2068
DrugBank ID
DB00277
IUPHAR ligand ID
413
KEGG ID
D00371
Unique Ingredient Identifier
0I55128JYK
Wikipedia Title
Theophylline
Medline Plus
a681006

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 7.8151274  H Acceptors
H Donor LogD (pH = 5.5) -0.7712048 
LogD (pH = 7.4) -0.89392424  Log P -0.7693217 
Molar Refractivity 44.9345 cm3 Polarizability 16.128607 Å3
Polar Surface Area 69.3 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P -0.26  LOG S -0.9 
Solubility (Water) 2.29e+01 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
0.1 M HCl: soluble expand Show data source
0.1 M NaOH: soluble expand Show data source
1-5 g/L expand Show data source
DMSO expand Show data source
ethanol: moderately soluble expand Show data source
H2O: slightly soluble expand Show data source
Apperance
white powder expand Show data source
White Solid expand Show data source
Melting Point
270-274 expand Show data source
271-273 °C expand Show data source
272-274°C expand Show data source
Hydrophobicity(logP)
-0.8 expand Show data source
Storage Condition
-20°C expand Show data source
Refrigerator expand Show data source
Room Temperature (15-30°C) expand Show data source
RTECS
XH3850000 expand Show data source
European Hazard Symbols
Harmful Harmful (Xn) expand Show data source
UN Number
1544 expand Show data source
2811 expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
1 expand Show data source
Hazard Class
6.1 expand Show data source
Packing Group
3 expand Show data source
III expand Show data source
Australian Hazchem
2X expand Show data source
Risk Statements
22 expand Show data source
R:22 expand Show data source
Safety Statements
S:36/37/39 expand Show data source
EU Classification
T2 expand Show data source
EU Hazard Identification Number
6.1B expand Show data source
Emergency Response Guidebook(ERG) Number
151 expand Show data source
GHS Pictograms
GHS06 expand Show data source
GHS Signal Word
Danger expand Show data source
GHS Hazard statements
H301 expand Show data source
GHS Precautionary statements
P301 + P310 expand Show data source
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Faceshields, Gloves expand Show data source
RID/ADR
UN 2811 6.1/PG 3 expand Show data source
Target
Respiratory Diseases expand Show data source
Admin Routes
oral, IV expand Show data source
Bioavailability
100% expand Show data source
Half Life
5-8 hours expand Show data source
Metabolism
hepatic to 1-methyluric acid expand Show data source
Protein Bound
40%, primarily to albumin expand Show data source
Legal Status
P (UK) expand Show data source
Rx (US) expand Show data source
Pregnancy Category
A (Australia) expand Show data source
C (US) expand Show data source
Gene Information
human ... ADORA1(134), ADORA2A(135), ADORA2B(136), ADORA3(140), PDE3A(5139), PDE4B(5142)mouse ... Adora2b(11541)rat ... Adora1(29290), Adora2a(25369), Adora2b(29316), Pde1b(29691), Pde3a(50678) expand Show data source
human ... ADORA2B(136), PDE3A(5139), PDE4B(5142) expand Show data source
Purity
≥99% expand Show data source
≥99.0% (HPLC) expand Show data source
Grade
anhydrous expand Show data source
Salt Data
Free Base expand Show data source
Certificate of Analysis
Download expand Show data source
Download expand Show data source
Download expand Show data source
Loss on Drying
≤0.5% loss on drying expand Show data source
Pharmacopeia Traceability
traceable to BP 327 expand Show data source
traceable to PhEur T080000 expand Show data source
traceable to USP 1653004 expand Show data source
Empirical Formula (Hill Notation)
C7H8N4O2 expand Show data source

DETAILS

DETAILS

Sigma Aldrich Sigma Aldrich MP Biomedicals MP Biomedicals Selleck Chemicals Selleck Chemicals DrugBank DrugBank Wikipedia Wikipedia TRC TRC
Sigma Aldrich - 88308 external link
Biochem/physiol Actions
Phosphodiesterase inhibitor; diuretic; cardiac stimulant; muscle relaxant; asthma medication.
Other Notes
Potent competitive inhibitor of cAMP phosphodiesterase1
Sigma Aldrich - T1633 external link
Biochem/physiol Actions
Phosphodiesterase inhibitor; diuretic; cardiac stimulant; muscle relaxant; asthma medication.
Sigma Aldrich - 92033 external link
Biochem/physiol Actions
Phosphodiesterase inhibitor; diuretic; cardiac stimulant; muscle relaxant; asthma medication.
MP Biomedicals - 02103024 external link
Crystalline
Anhydrous
MP Biomedicals - 05214629 external link
MP Biomedicals Rare Chemical collection
Selleck Chemicals - S1621 external link
Related research area: Immunology
DrugBank - DB00277 external link
Item Information
Drug Groups approved
Description A methyl xanthine derivative from tea with diuretic, smooth muscle relaxant, bronchial dilation, cardiac and central nervous system stimulant activities. Theophylline inhibits the 3',5'-cyclic nucleotide phosphodiesterase that degrades cyclic AMP thus potentiates the actions of agents that act through adenylate cyclase and cyclic AMP. [PubChem]
Indication For the treatment of the symptoms and reversible airflow obstruction associated with chronic asthma and other chronic lung diseases, such as emphysema and chronic bronchitis.
Pharmacology Theophylline, an xanthine derivative chemically similar to caffeine and theobromine, is used to treat asthma and bronchospasm. Theophylline has two distinct actions in the airways of patients with reversible (asthmatic) obstruction; smooth muscle relaxation (i.e., bronchodilation) and suppression of the response of the airways to stimuli (i.e., non-bronchodilator prophylactic effects).
Toxicity Symptoms of overdose include seizures, arrhythmias, and GI effects.
Affected Organisms
Humans and other mammals
Biotransformation Hepatic. Biotransformation takes place through demethylation to 1-methylxanthine and 3-methylxanthine and hydroxylation to 1,3-dimethyluric acid. 1-methylxanthine is further hydroxylated, by xanthine oxidase, to 1-methyluric acid. About 6% of a theophylline dose is N-methylated to caffeine. Caffeine and 3-methylxanthine are the only theophylline metabolites with pharmacologic activity.
Absorption Theophylline is rapidly and completely absorbed after oral administration in solution or immediate-release solid oral dosage form.
Half Life 8 hours
Protein Binding 40%, primarily to albumin.
Elimination Theophylline does not undergo any appreciable pre-systemic elimination, distributes freely into fat-free tissues and is extensively metabolized in the liver. Renal excretion of unchanged theophylline in neonates amounts to about 50% of the dose, compared to about 10% in children older than three months and in adults.
Distribution * 0.3 to 0.7 L/kg
Clearance * 0.29 mL/kg/min [Premature neonates, postnatal age 3-15 days]
* 0.64 mL/kg/min [Premature neonates, postnatal age 25-57 days]
* 1.7 mL/kg/min [Children 1-4 years]
* 1.6 mL/kg/min [Children 4-12 years]
* 0.9 mL/kg/min [Children 13-15 years]
* 1.4 mL/kg/min [Children 16-17 years]
* 0.65 mL/kg/min [Adults (16-60 years), otherwise healthy non-smoking asthmatics]
* 0.41 mL/kg/min [Elderly (>60 years), non-smokers with normal cardiac, liver, and renal function]
* 0.33 mL/kg/min [Acute pulmonary edema]
* 0.54 mL/kg/min [COPD >60 years, stable, non-smoker >1 year]
* 0.48 mL/kg/min [COPD with cor pulmonale]
* 1.25 mL/kg/min [Cystic fibrosis (14-28 years)]
* 0.31 mL/kg/min [Liver disease cirrhosis]
* 0.35 mL/kg/min [acute hepatitis]
* 0.65 mL/kg/min [cholestasis]
* 0.47 mL/kg/min [Sepsis with multi-organ failure]
* 0.38 mL/kg/min [hypothyroid]
* 0.8 mL/kg/min [hyperthyroid]
External Links
Wikipedia
RxList
PDRhealth
Drugs.com
Toronto Research Chemicals - T343850 external link
Xanthine derivative with diuretic, cardiac stimulant and smooth muscle relaxant activities; isomeric with theobromine. Small amounts occur in tea. Bronchodilator.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Cohen, J.L., et al.: Anal. Profiles Drug Subs., 4, 466 (1975)
  • • Svedmyr, K., et al.: Allergy, 37, 111 (1975)
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PATENTS

PATENTS

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