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1H-Purine-2,6-dione, 3,9-dihydro-1,3-dimethyl-, hydrate (1:1)

PubChem CID
91268
Structure
1H-Purine-2,6-dione, 3,9-dihydro-1,3-dimethyl-, hydrate (1:1)_small.png
1H-Purine-2,6-dione, 3,9-dihydro-1,3-dimethyl-, hydrate (1:1)_3D_Structure.png
Molecular Formula
Synonyms
  • Theophylline monohydrate
  • 5967-84-0
  • 1,3-Dimethylxanthine monohydrate
  • Theolair-SR
  • Theophylline (monohydrate)
Molecular Weight
198.18 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2005-08-01
  • Modify:
    2025-01-18
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 ADENYLYL CYCLASES and cyclic AMP.
See also: Theophylline (annotation moved to).

1 Structures

1.1 2D Structure

Chemical Structure Depiction
1H-Purine-2,6-dione, 3,9-dihydro-1,3-dimethyl-, hydrate (1:1).png

1.2 3D Conformer

3D Conformer of Parent

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

1,3-dimethyl-7H-purine-2,6-dione;hydrate
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 InChI

InChI=1S/C7H8N4O2.H2O/c1-10-5-4(8-3-9-5)6(12)11(2)7(10)13;/h3H,1-2H3,(H,8,9);1H2
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

INQSMEFCAIHTJG-UHFFFAOYSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.4 SMILES

CN1C2=C(C(=O)N(C1=O)C)NC=N2.O
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C7H8N4O2.H2O
C7H10N4O3
Computed by PubChem 2.2 (PubChem release 2021.10.14)

2.3 Other Identifiers

2.3.1 CAS

5967-84-0

2.3.2 European Community (EC) Number

2.3.3 UNII

2.3.4 ChEMBL ID

2.3.5 DSSTox Substance ID

2.3.6 KEGG ID

2.3.7 Wikidata

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • 1,3 Dimethylxanthine
  • 1,3-Dimethylxanthine
  • 3,7-Dihydro-1,3-dimethyl-1H-purine-2,6-dione
  • Accurbron
  • Aerobin
  • Aerolate
  • Afonilum Retard
  • Anhydrous, Theophylline
  • Aquaphyllin
  • Armophylline
  • Bronchoparat
  • Bronkodyl
  • Constant T
  • Constant-T
  • ConstantT
  • ct, theo von
  • Elixophyllin
  • Euphylong
  • Glycinate, Theophylline Sodium
  • Glycine Theophyllinate
  • Lodrane
  • Monospan
  • Nuelin
  • Nuelin S.A.
  • Quibron T SR
  • Quibron T-SR
  • Quibron TSR
  • Slo Phyllin
  • Slo-Phyllin
  • SloPhyllin
  • Sodium Glycinate, Theophylline
  • Somophyllin T
  • Somophyllin-T
  • SomophyllinT
  • Sustaire
  • Synophylate
  • Theo 24
  • Theo Dur
  • theo von ct
  • Theo-24
  • Theo-Dur
  • Theo24
  • Theobid
  • Theocin
  • Theoconfin Continuous
  • Theodur
  • Theolair
  • Theolix
  • Theon
  • Theonite
  • Theopek
  • Theophyllinate, Glycine
  • Theophylline
  • Theophylline Anhydrous
  • Theophylline Sodium Glycinate
  • Theospan
  • Theostat
  • Theovent
  • Uniphyl
  • Uniphyllin
  • Uniphylline
  • von ct, theo

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
198.18 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
2
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
4
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
0
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
198.07529019 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
198.07529019 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
70.3 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
14
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
267
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Covalently-Bonded Unit Count
Property Value
2
Reference
Computed by PubChem
Property Name
Compound Is Canonicalized
Property Value
Yes
Reference
Computed by PubChem (release 2021.10.14)

3.2 Chemical Classes

3.2.1 Drugs

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

5 Chemical Vendors

6 Drug and Medication Information

6.1 Drug Classes

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

6.2 Clinical Trials

6.2.1 EU Clinical Trials Register

7 Pharmacology and Biochemistry

7.1 MeSH Pharmacological Classification

Bronchodilator Agents
Agents that cause an increase in the expansion of a bronchus or bronchial tubes. (See all compounds classified as Bronchodilator Agents.)
Phosphodiesterase Inhibitors
Compounds which inhibit or antagonize the biosynthesis or actions of phosphodiesterases. (See all compounds classified as Phosphodiesterase Inhibitors.)
Vasodilator Agents
Drugs used to cause dilation of the blood vessels. (See all compounds classified as Vasodilator Agents.)
Purinergic P1 Receptor Antagonists
Compounds that bind to and block the stimulation of PURINERGIC P1 RECEPTORS. (See all compounds classified as Purinergic P1 Receptor Antagonists.)

8 Safety and Hazards

8.1 Hazards Identification

8.1.1 GHS Classification

Pictogram(s)
Acute Toxic
Signal
Danger
GHS Hazard Statements

H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]

H311 (20%): Toxic in contact with skin [Danger Acute toxicity, dermal]

H330 (20%): Fatal if inhaled [Danger Acute toxicity, inhalation]

Precautionary Statement Codes

P260, P262, P264, P270, P271, P280, P284, P301+P316, P302+P352, P304+P340, P316, P320, P321, P330, P361+P364, P403+P233, P405, and P501

(The corresponding statement to each P-code can be found at the GHS Classification page.)

ECHA C&L Notifications Summary

Aggregated GHS information provided per 5 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

8.1.2 Hazard Classes and Categories

Acute Tox. 3 (100%)

Acute Tox. 3 (20%)

Acute Tox. 2 (20%)

8.2 Regulatory Information

The Australian Inventory of Industrial Chemicals
Chemical: 1H-Purine-2,6-dione, 3,7-dihydro-1,3-dimethyl-, monohydrate

8.3 Other Safety Information

Chemical Assessment
Evaluation - 1H-Purine-2,6-dione, 3,7-dihydro-1,3-dimethyl- (theophylline)

9 Toxicity

9.1 Toxicological Information

9.1.1 Effects During Pregnancy and Lactation

◉ Summary of Use during Lactation

Expert opinion considers use of theophylline to be acceptable during breastfeeding. Maternal theophylline use may occasionally cause stimulation and irritability and fretful sleep in infants. Newborn and especially preterm infants are most likely to be affected because of their slow elimination and low serum protein binding of theophylline. There is no need to avoid theophylline products; however, keep maternal serum concentrations in the lower part of the therapeutic range and monitor the infant for signs of theophylline side effects. Infant serum theophylline concentrations can help to determine if signs of agitation are due to theophylline. Avoiding breastfeeding for 2 hours after intravenous or 4 hours after an immediate-release oral theophylline product can decrease the dose received by the breastfed infant. When theophylline is given as an oral sustained-release product, timing of nursing with respect to the dose is of little or no benefit.

◉ Effects in Breastfed Infants

Irritability and fretful sleeping occurred in a 3-day-old breastfed infant on days of maternal aminophylline intake of 200 mg every 6 hours. These effects ceased with discontinuation and recurred on rechallenge over the next 9 months. These effects were probably caused by theophylline in breastmilk. Another five infants reported in this paper showed no adverse reactions after maternal theophylline ingestion. Accumulation of theophylline in infant serum appears most likely in neonates and premature infants because they eliminate theophylline slowly.

◉ Effects on Lactation and Breastmilk

Relevant published information was not found as of the revision date.

10 Literature

10.1 Consolidated References

10.2 NLM Curated PubMed Citations

10.3 Springer Nature References

10.4 Chemical Co-Occurrences in Literature

10.5 Chemical-Gene Co-Occurrences in Literature

10.6 Chemical-Disease Co-Occurrences in Literature

11 Patents

11.1 Depositor-Supplied Patent Identifiers

11.2 WIPO PATENTSCOPE

11.3 Chemical Co-Occurrences in Patents

11.4 Chemical-Disease Co-Occurrences in Patents

11.5 Chemical-Gene Co-Occurrences in Patents

12 Interactions and Pathways

12.1 Chemical-Target Interactions

13 Biological Test Results

13.1 BioAssay Results

14 Classification

14.1 MeSH Tree

14.2 NCI Thesaurus Tree

14.3 KEGG: ATC

14.4 KEGG: Target-based Classification of Drugs

14.5 KEGG: Risk Category of Japanese OTC Drugs

14.6 KEGG: Drug Groups

14.7 ChemIDplus

14.8 UN GHS Classification

14.9 NORMAN Suspect List Exchange Classification

14.10 EPA DSSTox Classification

14.11 MolGenie Organic Chemistry Ontology

15 Information Sources

  1. Australian Industrial Chemicals Introduction Scheme (AICIS)
    1H-Purine-2,6-dione, 3,7-dihydro-1,3-dimethyl-, monohydrate
    https://services.industrialchemicals.gov.au/search-assessments/
    1H-Purine-2,6-dione, 3,7-dihydro-1,3-dimethyl-, monohydrate
    https://services.industrialchemicals.gov.au/search-inventory/
  2. CAS Common Chemistry
    LICENSE
    The data from CAS Common Chemistry is provided under a CC-BY-NC 4.0 license, unless otherwise stated.
    https://creativecommons.org/licenses/by-nc/4.0/
    1H-Purine-2,6-dione, 3,9-dihydro-1,3-dimethyl-, hydrate (1:1)
    https://commonchemistry.cas.org/detail?cas_rn=5967-84-0
  3. ChemIDplus
    ChemIDplus Chemical Information Classification
    https://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
  4. EPA DSSTox
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  5. European Chemicals Agency (ECHA)
    LICENSE
    Use of the information, documents and data from the ECHA website is subject to the terms and conditions of this Legal Notice, and subject to other binding limitations provided for under applicable law, the information, documents and data made available on the ECHA website may be reproduced, distributed and/or used, totally or in part, for non-commercial purposes provided that ECHA is acknowledged as the source: "Source: European Chemicals Agency, http://echa.europa.eu/". Such acknowledgement must be included in each copy of the material. ECHA permits and encourages organisations and individuals to create links to the ECHA website under the following cumulative conditions: Links can only be made to webpages that provide a link to the Legal Notice page.
    https://echa.europa.eu/web/guest/legal-notice
    1H-Purine-2,6-dione, 3,9-dihydro-1,3-dimethyl-, hydrate (1:1)
    https://echa.europa.eu/substance-information/-/substanceinfo/100.110.629
    1H-Purine-2,6-dione, 3,9-dihydro-1,3-dimethyl-, hydrate (1:1) (EC: 611-861-2)
    https://echa.europa.eu/information-on-chemicals/cl-inventory-database/-/discli/details/21441
  6. FDA Global Substance Registration System (GSRS)
    LICENSE
    Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required.
    https://www.fda.gov/about-fda/about-website/website-policies#linking
  7. ChEMBL
    LICENSE
    Access to the web interface of ChEMBL is made under the EBI's Terms of Use (http://www.ebi.ac.uk/Information/termsofuse.html). The ChEMBL data is made available on a Creative Commons Attribution-Share Alike 3.0 Unported License (http://creativecommons.org/licenses/by-sa/3.0/).
    http://www.ebi.ac.uk/Information/termsofuse.html
  8. Drug Gene Interaction database (DGIdb)
    LICENSE
    The data used in DGIdb is all open access and where possible made available as raw data dumps in the downloads section.
    http://www.dgidb.org/downloads
  9. Drugs and Lactation Database (LactMed)
  10. EU Clinical Trials Register
  11. KEGG
    LICENSE
    Academic users may freely use the KEGG website. Non-academic use of KEGG generally requires a commercial license
    https://www.kegg.jp/kegg/legal.html
    Anatomical Therapeutic Chemical (ATC) classification
    http://www.genome.jp/kegg-bin/get_htext?br08303.keg
    Target-based classification of drugs
    http://www.genome.jp/kegg-bin/get_htext?br08310.keg
    Risk category of Japanese OTC drugs
    http://www.genome.jp/kegg-bin/get_htext?br08312.keg
  12. Springer Nature
  13. Wikidata
  14. Medical Subject Headings (MeSH)
    LICENSE
    Works produced by the U.S. government are not subject to copyright protection in the United States. Any such works found on National Library of Medicine (NLM) Web sites may be freely used or reproduced without permission in the U.S.
    https://www.nlm.nih.gov/copyright.html
    Phosphodiesterase Inhibitors
    https://www.ncbi.nlm.nih.gov/mesh/68010726
    Purinergic P1 Receptor Antagonists
    https://www.ncbi.nlm.nih.gov/mesh/68058915
  15. PubChem
  16. GHS Classification (UNECE)
  17. NORMAN Suspect List Exchange
    LICENSE
    Data: CC-BY 4.0; Code (hosted by ECI, LCSB): Artistic-2.0
    https://creativecommons.org/licenses/by/4.0/
    NORMAN Suspect List Exchange Classification
    https://www.norman-network.com/nds/SLE/
  18. NCI Thesaurus (NCIt)
    LICENSE
    Unless otherwise indicated, all text within NCI products is free of copyright and may be reused without our permission. Credit the National Cancer Institute as the source.
    https://www.cancer.gov/policies/copyright-reuse
  19. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  20. PATENTSCOPE (WIPO)
CONTENTS