8-Bromotheophylline acts as an antagonist at adenosine receptors, particularly the A2A receptor. It also inhibits muscarinic acetylcholine receptors, especially M1 and M3 subtypes. It modulates various ion channels, including sodium and calcium channels. It is used to synthesize oxazolo[2,3-f]purinediones for evaluating adenosine A1 and A2A receptor affinity.

In vitro, 8-Bromotheophylline inhibits a diverse range of enzymes, receptors, and ion channels. It acts as an antagonist at adenosine A2A receptors and inhibits muscarinic acetylcholine receptors. It modulates sodium and calcium channels. It is used to study adenosine signaling, cholinergic signaling, and ion channel function in various biological processes.

In vivo, 8-Bromotheophylline's inhibition of adenosine receptors helps researchers understand the role of adenosine signaling in the cardiovascular system, including its effects on heart rate and blood pressure. Its ability to modulate various receptors and ion channels makes it relevant to research on neurological disorders like epilepsy and Parkinson's disease.

Cell-free assays for 8-Bromotheophylline: adenosine A2A receptor binding is assessed using radioligand binding assays with membrane preparations. The compound is incubated with receptor membranes and radiolabeled ligands, and specific binding is measured by scintillation counting. IC50 or Ki values are calculated from displacement curves. Ion channel modulation is studied using patch-clamp electrophysiology.

In vitro cellular assays for 8-Bromotheophylline: cells expressing adenosine receptors or muscarinic receptors are treated with 8-Bromotheophylline at concentrations of 0.1-100 µM for 1-24 hours. Receptor-mediated signaling (e.g., cAMP levels for adenosine receptors, calcium flux for muscarinic receptors) is measured. Cell viability is assessed by MTT assay.

In vivo animal studies for 8-Bromotheophylline: animal models of neurological disorders (e.g., epilepsy, Parkinson's disease) or cardiovascular disease are used. Animals are administered 8-Bromotheophylline orally or intraperitoneally at doses of 1-10 mg/kg. Disease progression, behavioral changes, and physiological parameters are assessed.

Absorption, Distribution and Excretion
Following a single oral dose of theoBromotheophylline, absorption is rapid, reaching a peak plasma concentration of 2.5 mg/L within 0.78 hours. The mean residence time is 12 hours, with an AUC of 27 mg·h/L in the first 8 hours. Pharmacokinetics This pharmacokinetic profile has not been determined. Metabolism/Metabolites This pharmacokinetic profile has not been determined. Biological Half-Life The apparent elimination half-life is 21.35 hours.

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Pharmacokinetic properties of 8-Bromotheophylline: as a small molecule (molecular weight 259.06), it may have good oral bioavailability and tissue distribution. It is likely metabolized in the liver and excreted via the kidneys. The compound is soluble in various solvents. Storage: powder at -20°C for up to 3 years.

Protein Binding
The pharmacokinetic properties of this product have not yet been determined.

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Toxicity of 8-Bromotheophylline: comprehensive toxicity data are limited. As a xanthine derivative, it may have stimulant effects at high doses. It is for research use only and not for human therapeutic applications. Standard laboratory safety precautions should be followed.

[1]. Drabczyńska A, et al. Tricyclic oxazolo[2,3-f]purinediones: potency as adenosine receptor ligands and anticonvulsants. Bioorg Med Chem. 2004;12(18):4895-4908.

Bromotheophylline is the active ingredient in pamabrom, a mixture of 2-amino-2-methylpropanol and Bromotheophylline. Bromotheophylline in this mixture is a weak diuretic and has been used in combination with some analgesics to relieve symptoms of premenstrual syndrome. Since March 1980, Bromotheophylline has been listed as an inactive pharmaceutical ingredient by the U.S. Food and Drug Administration (FDA). It has also been approved by Health Canada for use alone or in combination with [DB00316] in over-the-counter drug products.
See also: Pamabrom (active ingredient); Pyrbromide (active ingredient).
Indications
Bromotheophylline is used as a diuretic and may also be used in combination with [DB00316] to relieve temporary edema, bloating, swelling, and fullness caused before and during menstruation.
Mechanism of Action
Bromotheophylline belongs to the xanthine class of drugs. As a drug in this class, theophylline is thought to increase renal tubular permeability, improve glomerular filtration rate, and inhibit proximal tubular reabsorption of sodium. It is speculated (but not yet confirmed) that the pamabromine mixture appears to have an additional mechanism of action, in which the presence of 2-amino-2-methyl-1-propanol inhibits the secretion of antidiuretic hormone from the posterior pituitary gland.

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Pharmacodynamics
The diuretic effect of theophylline immediately increases the frequency of urination. This effect helps relieve bloating and dysmenorrhea. This diuretic effect is achieved by increasing the glomerular filtration rate and possibly affecting renal tubular reabsorption, as it has been shown that taking these drugs leads to an increase in the concentration of sodium chloride in the urine, thereby increasing its excretion rate.

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8-Bromotheophylline is a research compound used for studying adenosine and muscarinic receptor signaling, ion channel modulation, and neurological disorders. It is the active moiety of pamabrom, used for premenstrual syndrome symptoms. It is used as a synthetic intermediate for oxazolo[2,3-f]purinediones. No FDA approvals as a standalone drug have been reported.

C7H7BRN4O2

259.06

257.975

10381-75-6

11808

Typically exists as solid at room temperature

1.9±0.1 g/cm3

469.5±55.0 °C at 760 mmHg

295-297ºC

237.7±31.5 °C

0.0±1.2 mmHg at 25°C

1.652

0.08

1

3

0

14

297

0

BrC1=NC2=C(C(N(C([H])([H])[H])C(N2C([H])([H])[H])=O)=O)N1[H]

SKTFQHRVFFOHTQ-UHFFFAOYSA-N

InChI=1S/C7H7BrN4O2/c1-11-4-3(9-6(8)10-4)5(13)12(2)7(11)14/h1-2H3,(H,9,10)

8-bromo-1,3-dimethyl-7H-purine-2,6-dione

2934.99.9001

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Note: Please store this product in a sealed and protected environment, avoid exposure to moisture.

Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples

Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.

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Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)
*Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution.
Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline)
Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil)
Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals).

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Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)]
*Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.
Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin → 500 μL Saline)
Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO → 100 μLPEG300 → 200 μL castor oil → 650 μL Saline)
Injection Formulation 7: Ethanol : Cremophor : Saline = 10： 10 : 80 (i.e. 100 μL Ethanol → 100 μL Cremophor → 800 μL Saline)
Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline
Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH → 900 μL Corn oil)
Injection Formulation 10: EtOH : PEG300：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline)

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Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium)
Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose
Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals).

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Oral Formulation 3: Dissolved in PEG400
Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose
Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose
Oral Formulation 6: Mixing with food powders

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Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently.

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 (Please use freshly prepared in vivo formulations for optimal results.)