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Merck
CN

88308

Theophylline

≥99.0% (HPLC)

Synonym(s):

1,3-Dimethylxanthine, 2,6-Dihydroxy-1,3-dimethylpurine, 3,7-Dihydro-1,3-dimethyl-1H-purine-2,6-dione

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About This Item

Empirical Formula (Hill Notation):
C7H8N4O2
CAS Number:
58-55-9
Molecular Weight:
180.16
EC Number:
200-385-7
UNSPSC Code:
41106305
PubChem Substance ID:
329769646
Beilstein/REAXYS Number:
13463
MDL number:
MFCD00079619

Key Documents

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InChI

1S/C7H8N4O2/c1-10-5-4(8-3-9-5)6(12)11(2)7(10)13/h3H,1-2H3,(H,8,9)

InChI key

ZFXYFBGIUFBOJW-UHFFFAOYSA-N

SMILES string

CN1C(=O)N(C)c2[nH]cnc2C1=O

biological source

synthetic

assay

≥99.0% (HPLC)

form

powder (with lumps)

loss

≤0.5% loss on drying

mp

271-273 °C

solubility

water: 5.5 g/L at 19.9 °C

Gene Information

human ... ADORA1(134), ADORA2A(135), ADORA2B(136), ADORA3(140), PDE3A(5139), PDE3B(5140), PDE4A(5141), PDE4B(5142), PDE4C(5143), PDE4D(5144)

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Biochem/physiol Actions

Phosphodiesterase inhibitor; diuretic; cardiac stimulant; muscle relaxant; asthma medication.

Other Notes

Potent competitive inhibitor of cAMP phosphodiesterase

pictograms

Skull and crossbonesHealth hazard
GHS06,GHS08

signalword

Danger

Hazard Classifications

Acute Tox. 3 Oral - Repr. 1B

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk

WGK 1

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Faceshields, Gloves

Regulatory Information

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Adenosine 3',5'-phosphate in biological materials. I. Purification and properties of cyclic 3',5'-nucleotide phosphodiesterase and use of this enzyme to characterize adenosine 3',5'-phosphate in human urine.
R W BUTCHER et al.
The Journal of biological chemistry, 237, 1244-1250 (1962-04-01)
David J Henderson-Smart et al.
The Cochrane database of systematic reviews, (1)(1), CD000273-CD000273 (2010-01-22)
Recurrent apnea is common in preterm infants, particularly at very early gestational ages. These episodes of loss of effective breathing can lead to hypoxemia and bradycardia, which may be severe enough to require resuscitation including use of positive pressure ventilation.
Mazen Al-Alawi et al.
The American journal of medicine, 127(5), 370-378 (2014-01-02)
Global estimates on aging predict an increased burden of asthma in the older population. Consequently, its recognition, diagnosis, and management in clinical practice require optimization. This review aims to provide an update for clinicians, highlighting advances in the understanding of
F S F Ram et al.
Respiratory medicine, 99(2), 135-144 (2005-02-18)
To determine the efficacy of oral theophylline compared with placebo in people with stable chronic obstructive pulmonary disease (COPD). Systematic review of randomized-controlled trials comparing oral theophylline with placebo for a minimum of 7 days in people with stable COPD.
Manja Wachsmuth et al.
Nucleic acids research, 41(4), 2541-2551 (2013-01-01)
Riboswitches are regulatory RNA elements typically located in the 5'-untranslated region of certain mRNAs and control gene expression at the level of transcription or translation. These elements consist of a sensor and an adjacent actuator domain. The sensor usually is
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