Identification
- Brand Names
- Pamprin Multi-symptom, Premsyn Pms
- Generic Name
- Bromotheophylline
- DrugBank Accession Number
- DB14018
- Background
Bromotheophylline is the active moiety of pamabrom, a mixture of 2-amino-2-methyl-propanol and bromotheophylline. From this mixture, bromotheophylline acts as a weak diuretic that has been used along with some analgesics to relieve the symptoms of premenstrual syndrome.1 Bromotheophylline is categorized on the FDA as a drug substance with an inactive state since March, 1980.3 It is also approved by Health Canada to be used alone or in combination with Acetaminophen in OTC products.4
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Bromotheophylline (DB14018)
- Weight
- Average: 259.063
Monoisotopic: 257.975238 - Chemical Formula
- C7H7BrN4O2
- Synonyms
- 8-Bromotheophylline
Pharmacology
- Indication
Bromotheophylline is used as a diuretic and also, in combination with Acetaminophen, it is used for the relief of temporary water weight gain, bloating, swelling and full feeling associated with the premenstrual and menstrual periods.5
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Used in combination for symptomatic treatment of Premenstrual syndrome Combination Product in combination with: Acetaminophen (DB00316), Mepyramine (DB06691) •••••••••••• ••••••• •••••• Used in combination for symptomatic treatment of Premenstrual syndrome Combination Product in combination with: Acetaminophen (DB00316) ••• ••• Used in combination for symptomatic treatment of Menstrual syndrome Combination Product in combination with: Acetaminophen (DB00316) ••• ••• Treatment of Water retention ••• ••• - Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Bromotheophylline diuretic action will produce an immediate increase in urination frequency. This effect aids in the relief of bloating and menstrual pain.1 This diuretic function is performed by the an increase in glomerular filtration and a potential effect in the tubular reabsorption as it is established that the administration of these agents produce a rise in the urinary concentration of sodium a chloride and thus, an increase in their rates of excretion.2
- Mechanism of action
Bromotheophylline is part of the group of the xanthines. As part of this group, it is thought that bromotheophylline increases the permeability of the renal tubule, increases glomerular filtration rate and inhibits the sodium reabsorption in the proximal tubule.2 It is thought but not confirmed that pamabrom as a mixture seems to have an additional mechanism of action in which the presence of 2-amino-2-methyl-1-propanol produces the suppression of the antidiuretic hormone in the posterior pituitary gland.8
- Absorption
When administered after one single oral dosage, bromotheophylline is rapidly absorbed and it reaches a maximal plasma concentration of 2.5 mg/L in 0.78 hours. The mean residence time is registered to be of 12 hours with an AUC in the first 8 hours of 27 mg.h/L.7
- Volume of distribution
This pharmacokinetic property has not been determined.
- Protein binding
This pharmacokinetic property has not been determined.
- Metabolism
This pharmacokinetic property has not been determined.
- Route of elimination
This pharmacokinetic property has not been determined.
- Half-life
The apparent elimination half-life is registered to be 21.35 hours.8
- Clearance
This pharmacokinetic property has not been determined.
- Adverse Effects
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In overdose, bromotheophylline does not produce hepatic toxicity.8
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your software1,2-Benzodiazepine The therapeutic efficacy of 1,2-Benzodiazepine can be decreased when used in combination with Bromotheophylline. Abacavir Bromotheophylline may increase the excretion rate of Abacavir which could result in a lower serum level and potentially a reduction in efficacy. Abametapir The serum concentration of Bromotheophylline can be increased when it is combined with Abametapir. Abatacept The metabolism of Bromotheophylline can be increased when combined with Abatacept. Abiraterone The serum concentration of Bromotheophylline can be increased when it is combined with Abiraterone. - Food Interactions
- Drink plenty of fluids. Avoid dehydration by drinking 6-8 glasses of water daily.
- Take with a full glass of water.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Pamabrom UA8U0KJM72 606-04-2 ATOTUUBRFJHZQG-UHFFFAOYSA-N - Over the Counter Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Diurex Capsule 50 mg/1 Oral Alva-Amco Pharmacal Companies, Inc. 2005-04-01 Not applicable US 
Diurex Capsule, liquid filled 50 mg/1 Oral Alva-Amco Pharmacal Companies, Inc. 2000-04-10 2022-01-31 US Diurex Max Tablet, film coated 50 mg/1 Oral Alva-Amco Pharmacal Companies, Inc. 2001-03-05 Not applicable US Diurex Max Tablet, film coated 50 mg/1 Oral Alva-Amco Pharmacal Companies, Inc. 1995-12-20 Not applicable US Diurex Water Caplets Tablet 50 mg Oral Alva Amco Pharmacal Companies, Inc. 2001-03-12 Not applicable Canada 
- Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image ActiMol Menstrual Tablet Pamabrom (25 mg) + Acetaminophen (500 mg) Tablet Oral PHARMANIAGA MANUFACTURING BERHAD 2020-09-08 Not applicable Malaysia 
BackAid Max Pamabrom (25 mg/1) + Acetaminophen (500 mg/1) Tablet, film coated Oral Alva-Amco Pharmacal Companies, Inc. 1992-02-01 Not applicable US Cramp Tabs Pamabrom (25 mg/1) + Acetaminophen (325 mg/1) Tablet Oral Redicare Llc 2017-02-01 Not applicable US Cramp Tabs Pamabrom (25 1/1) + Acetaminophen (325 1/1) Tablet Oral Advanced First Aid, Inc. 2015-08-10 Not applicable US Crane Safety Cramp Pamabrom (25 mg/1) + Acetaminophen (325 mg/1) Tablet, film coated Oral Crane Safety LLC 2020-01-17 2023-11-01 US - Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Diurex Pamabrom (50 mg/1) Capsule, liquid filled Oral Alva-Amco Pharmacal Companies, Inc. 2000-04-10 2022-01-31 US Diurex Max Pamabrom (50 mg/1) Tablet, film coated Oral Alva-Amco Pharmacal Companies, Inc. 1995-12-20 Not applicable US Pamabrom Pamabrom (50 mg/1) Capsule, liquid filled Oral Walgreens Co. 2020-11-24 Not applicable US
Categories
- ATC Codes
- R03DA20 — Combinations of xanthines
- Drug Categories
- Classification
- Not classified
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- FZG87K1MQ6
- CAS number
- 10381-75-6
- InChI Key
- SKTFQHRVFFOHTQ-UHFFFAOYSA-N
- InChI
- InChI=1S/C7H7BrN4O2/c1-11-4-3(9-6(8)10-4)5(13)12(2)7(11)14/h1-2H3,(H,9,10)
- IUPAC Name
- 8-bromo-1,3-dimethyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione
- SMILES
- CN1C2=C(NC(Br)=N2)C(=O)N(C)C1=O
References
- General References
- Shah U, Kavad M, Raval M: Development and Validation of Stability-indicating RP-HPLC Method for Estimation of Pamabrom in Tablets. Indian J Pharm Sci. 2014 May;76(3):198-202. [Article]
- MUDGE GH, WEINER IM: The mechanism of action of mercurial and xanthine diuretics. Ann N Y Acad Sci. 1958 Feb 3;71(4):344-54. [Article]
- FDA Submission [Link]
- Health Canada [Link]
- FDA history [Link]
- Dailymed [Link]
- CNKI [Link]
- Annexpublishers [Link]
- External Links
- ChemSpider
- 11315
- BindingDB
- 50045345
- 1546386
- ChEMBL
- CHEMBL316160
- ZINC
- ZINC000100005670
- MSDS
- Download (47.6 KB)
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Capsule Oral 50 mg/1 Capsule, liquid filled Oral 50 mg/1 Tablet, film coated Oral 50 mg/1 Tablet Oral 50 mg Capsule Oral 50 mg Capsule Oral Tablet, film coated Oral Tablet Oral 50 mg/1 Tablet, coated Oral Tablet, film coated Oral 25 mg Tablet Oral - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 295-316 ºC 'MSDS' boiling point (°C) Decomposes at 300 ºC 'MSDS' water solubility Soluble Shah U., Kavad M. and Raval M. Indian J Pharm Sci. (2014) pKa 5.45 Brittain H. Profiles of drug substances, excipients and related methodology. (2007) - Predicted Properties
Property Value Source Water Solubility 3.92 mg/mL ALOGPS logP 0.23 ALOGPS logP 0.29 Chemaxon logS -1.8 ALOGPS pKa (Strongest Acidic) 5.58 Chemaxon pKa (Strongest Basic) -3 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 3 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 69.3 Å2 Chemaxon Rotatable Bond Count 0 Chemaxon Refractivity 52.56 m3·mol-1 Chemaxon Polarizability 20.67 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-0a4i-0090000000-64e1f352a8b3b078f4fd Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-0a4i-0290000000-e66daf8a4433105a0fd7 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-0pi0-0490000000-850278f0d18c82c8d997 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-0a6r-5490000000-b25cffc46a538e71e183 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0kft-1900000000-6aa84fe37ce908fd5240 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-004i-9200000000-885993cb246b81efc5fe Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 137.12422 predictedDeepCCS 1.0 (2019) [M+H]+ 139.51979 predictedDeepCCS 1.0 (2019) [M+Na]+ 146.31384 predictedDeepCCS 1.0 (2019)
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Substrate
- Curator comments
- This enzyme listing is based on pharmacokinetic data for methylxanthines as a drug class. Methylxanthines are metabolized by CYP1A2. This drug is a methylxanthine and is therefore assumed to be metabolized by this enzyme.
- General Function
- Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
- Gene Name
- CYP1A2
- Uniprot ID
- P05177
- Uniprot Name
- Cytochrome P450 1A2
- Molecular Weight
- 58293.76 Da
References
- Thorn CF, Aklillu E, McDonagh EM, Klein TE, Altman RB: PharmGKB summary: caffeine pathway. Pharmacogenet Genomics. 2012 May;22(5):389-95. doi: 10.1097/FPC.0b013e3283505d5e. [Article]
- Buters JT, Tang BK, Pineau T, Gelboin HV, Kimura S, Gonzalez FJ: Role of CYP1A2 in caffeine pharmacokinetics and metabolism: studies using mice deficient in CYP1A2. Pharmacogenetics. 1996 Aug;6(4):291-6. [Article]
- Hakooz NM: Caffeine metabolic ratios for the in vivo evaluation of CYP1A2, N-acetyltransferase 2, xanthine oxidase and CYP2A6 enzymatic activities. Curr Drug Metab. 2009 May;10(4):329-38. [Article]
- Rasmussen BB, Brosen K: Determination of urinary metabolites of caffeine for the assessment of cytochrome P4501A2, xanthine oxidase, and N-acetyltransferase activity in humans. Ther Drug Monit. 1996 Jun;18(3):254-62. [Article]
- Theophylline metabolic pathway [Link]
- CYP1A2 activity, gender and smoking, as variables influencing the toxicity of caffeine [File]
Drug created at April 27, 2018 01:52 / Updated at February 20, 2024 23:55