Identification
- Generic Name
- Choline C 11
- DrugBank Accession Number
- DB09277
- Background
Choline C 11 is a marker for cellular proliferation as its main molecule is a precursor for the biosynthesis of phospholipids which are essential components of all cell membranes.4 It was developed by MCPRF and FDA first approved in September 2012.
- Type
- Small Molecule
- Groups
- Approved, Investigational
- Structure
Structure for Choline C 11 (DB09277)
- Weight
- Average: 138.62
Monoisotopic: 138.0878256 - Chemical Formula
- C5H14ClNO
- Synonyms
- 11C-choline
- 11C-choline chloride
Pharmacology
- Indication
Choline C11 is indicated for its use in positron emission tomography (PET) imaging in patients with suspected prostate cancer recurrence and non-informative bone scintigraphy, computerized tomography or magnetic resonance imaging.Label,2
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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
Choline is phosphorylated by choline kinase into phosphorylcholine. This phosphorylated form gets trapped inside the cell. Cancer cells exhibit an increased cell wall membrane synthesis as well as an increased activity of choline kinase. Choline C11 presents a small tracer activity in the urinary collecting system and this property makes it a very noble compound in the evaluation of ureters and bladder.3
- Mechanism of action
Choline is incorporated into phosphatidylcholine which is a major membrane phospholipid in mammalian cells. The use of choline C11 is based on the knowledge that malignant tumors with increased cellular proliferation take up more choline when compared with normal cells for the formation of cellular membranes.1 The increased uptake of choline is explained by its use as a substrate in phospholipid synthesis in cell membranes, transmembrane signaling, and lipid and cholesterol transport and metabolism.2
- Absorption
The highest normal tissue uptake is seen in renal cortex, liver, pancreas and salivary glands. It presents a variable bowel, prostate and pituitary uptake and a low uptake in the cerebral cortex. The short half-life of choline C11 limits the availability and it is recommended to be delivered within 2-3 half-lives from producing cyclotron.5
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
Choline C11 is phosphorylated by choline kinase and incorporated into phospholipids in the body. In some of the tissues, choline oxidation is prominent. The oxidative metabolite of choline is betaine which is the major metabolite of choline C11. A small portion of the administered dose remains unchanged 40 minutes after administration.5
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- Route of elimination
Choline 11 presents a minimal urinary excretion and it represents <2% of the injected radioactivity.2 After intravenous administration, choline C11 gets rapidly cleared from the circulation (<3 min) with a high clearance by liver and kidneys.5 The oxidation metabolite of choline, named betaine, is excreted into the urine.5
- Half-life
The isotope half-life of choline C11 is 20.4 min.2
- Clearance
After intravenous injection, choline C11 is rapidly cleared from the bloodstream. The clearance rate of choline C11 is or 0.014 ml/min.5
- Adverse Effects
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Choline is a natural compound with no known toxic effects at the levels administered in the form of choline C11. The carcinogenic effect of choline C11 has not been determined in long-term studies.5
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- 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 softwareAbacavir Abacavir may decrease the excretion rate of Choline C 11 which could result in a higher serum level. Aceclofenac Aceclofenac may decrease the excretion rate of Choline C 11 which could result in a higher serum level. Acemetacin Acemetacin may decrease the excretion rate of Choline C 11 which could result in a higher serum level. Acetaminophen Acetaminophen may decrease the excretion rate of Choline C 11 which could result in a higher serum level. Acetazolamide Acetazolamide may increase the excretion rate of Choline C 11 which could result in a lower serum level and potentially a reduction in efficacy. - Food Interactions
- Not Available
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as cholines. These are organic compounds containing a N,N,N-trimethylethanolammonium cation.
- Kingdom
- Organic compounds
- Super Class
- Organic nitrogen compounds
- Class
- Organonitrogen compounds
- Sub Class
- Quaternary ammonium salts
- Direct Parent
- Cholines
- Alternative Parents
- Tetraalkylammonium salts / 1,2-aminoalcohols / Primary alcohols / Organopnictogen compounds / Organic zwitterions / Organic chloride salts / Hydrocarbon derivatives
- Substituents
- 1,2-aminoalcohol / Alcohol / Aliphatic acyclic compound / Alkanolamine / Amine / Choline / Hydrocarbon derivative / Organic chloride salt / Organic oxygen compound / Organic salt
- Molecular Framework
- Aliphatic acyclic compounds
- External Descriptors
- chloride salt, quaternary ammonium salt (CHEBI:72321)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- 381E0BTR5Q
- CAS number
- 87591-54-6
- InChI Key
- SGMZJAMFUVOLNK-ULWFUOSBSA-M
- InChI
- InChI=1S/C5H14NO.ClH/c1-6(2,3)4-5-7;/h7H,4-5H2,1-3H3;1H/q+1;/p-1/i1-1;
- IUPAC Name
- (2-hydroxyethyl)((¹¹C)methyl)dimethylazanium chloride
- SMILES
- [Cl-].C[N+](C)([11CH3])CCO
References
- General References
- Chotipanich C, Kunawudhi A, Promteangtrong C, Tungsuppawattanakit P, Sricharunrat T, Wongsa P: Diagnosis of Hepatocellular Carcinoma Using C11 Choline PET/CT: Comparison with F18 FDG, ContrastEnhanced MRI and MDCT. Asian Pac J Cancer Prev. 2016;17(7):3569-73. [Article]
- Fox JJ, Schoder H, Larson SM: Molecular imaging of prostate cancer. Curr Opin Urol. 2012 Jul;22(4):320-7. doi: 10.1097/MOU.0b013e32835483d5. [Article]
- Welle CL, Cullen EL, Peller PJ, Lowe VJ, Murphy RC, Johnson GB, Binkovitz LA: (1)(1)C-Choline PET/CT in Recurrent Prostate Cancer and Nonprostatic Neoplastic Processes. Radiographics. 2016 Jan-Feb;36(1):279-92. doi: 10.1148/rg.2016150135. [Article]
- Krohn KA: Evaluation of alternative approaches for imaging cellular growth. Q J Nucl Med. 2001 Jun;45(2):174-8. [Article]
- Society of nuclear medicine and molecular imaging [Link]
- External Links
- PubChem Compound
- 14989482
- PubChem Substance
- 310265171
- ChemSpider
- 28514887
- ChEBI
- 72321
- ChEMBL
- CHEMBL2095207
- FDA label
- Download (400 KB)
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 3 Completed Diagnostic Metastatic Prostate Cancer 1 2 Unknown Status Diagnostic Hepatocellular Carcinoma 1 1 Completed Diagnostic Prostate Cancer 1 0 Not Yet Recruiting Diagnostic Lymphangioleiomyomatosis (LAM) 1 Not Available Active Not Recruiting Diagnostic Prostate Cancer 2
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source water solubility Soluble 'Choline MSDS' Radioactivity (mCi/mL) 33 'FDA label' - Predicted Properties
Property Value Source Water Solubility 5.45 mg/mL ALOGPS logP -4 ALOGPS logP -4.7 Chemaxon logS -1.4 ALOGPS pKa (Strongest Acidic) 13.97 Chemaxon pKa (Strongest Basic) -3.2 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 1 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 20.23 Å2 Chemaxon Rotatable Bond Count 2 Chemaxon Refractivity 42.19 m3·mol-1 Chemaxon Polarizability 12.57 Å3 Chemaxon Number of Rings 0 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule Yes Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-0ab9-6900000000-86eed754d1143fcb884d - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 109.878494 predictedDeepCCS 1.0 (2019) [M+H]+ 112.25815 predictedDeepCCS 1.0 (2019) [M+Na]+ 119.64653 predictedDeepCCS 1.0 (2019)
Drug created at October 28, 2015 22:45 / Updated at June 12, 2020 16:52