Propiolactone
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Identification
- Generic Name
- Propiolactone
- DrugBank Accession Number
- DB09348
- Background
Propiolactone is a lactone compound with a four-membered ring. It is a colorless liquid with a pungent slightly sweet odor. Propiolactone is a disinfectant used for the sterilization of blood plasma, vaccines, tissue grafts, surgical instruments, and enzymes. It has been used against bacteria, fungi, and virus.1 It is currently FDA approved for its use as an indirect additive used in food contact substances. Propiolactone was first commercially available in the United States in 1958.1
- Type
- Small Molecule
- Groups
- Approved, Withdrawn
- Structure
- Weight
- Average: 72.063
Monoisotopic: 72.021129369 - Chemical Formula
- C3H4O2
- Synonyms
- 1,3-propiolactone
- 3-propanolide
- beta-Propiolactone
- betapron
- Propiolactona
- Propiolactone
- β-propiolactone
- External IDs
- NSC-21626
Pharmacology
- Indication
Propiolactone was used for vaccines, tissue grafts, surgical instruments, and enzymes, as a sterilant of blood plasma, water, milk and nutrient broth as a vapor-phase disinfectant in enclosed spaces. Its sporicidal action is used against vegetative bacteria, pathologic fungi, and viruses.5 It is no longer used in medical procedures or in food.1
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- Pharmacodynamics
When employed under conditions of maximum effectiveness, propiolactone is approximately 25 more active as a vapor phase disinfectant than formaldehyde, 4000 times more active than ethylene oxide and 50000 times more active than methyl bromide.6 It has been shown to be mutagenic by inducing cell transformation, chromosomal aberrations and chromatoid exchange. Propiolactone has been shown to be mutagenic in both somatic and germ cells.7
- Mechanism of action
Propiolactone is an alkylating agent that acts through alkylation of carboxyl- and hydroxyl- groups. The lactone ring splits either at the first or third carbon.6 Propiolactone reacts with polynucleotides and DNA, mainly at N7 of guanine and N1 of adenine to form carboxyethyl derivatives. It also forms adducts with N3 of cytosine and thymine.7
Target Actions Organism ADNA adductHumans - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Propiolactone is highly bound to proteins showing an almost 2-fold binding increase when compared to DNA and RNA.4
- Metabolism
Propiolactone is completely hydrolyzed after 3 hours of being in an aqueous solution and this time can be even faster in the presence of cellular debris and cell culture media.8 When in water, the lactone ring opens at the alkyl and acyl bonds.3 The degradation products of propiolactone are not toxic.8
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- Route of elimination
Not Available
- Half-life
The half-life of propiolactone in water is of 225 minutes.2
- Clearance
Not Available
- Adverse Effects
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- Toxicity
Based on experimental trials, it has been determined that propiolactone is a human carcinogen. The results have shown the generation of tumors in several tissues and from different administration routes.1
- 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.Not Available
- Food Interactions
- Not Available
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as beta propiolactones. These are organic compounds containing a four-member lactone (a cyclic ester).
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Lactones
- Sub Class
- Beta propiolactones
- Direct Parent
- Beta propiolactones
- Alternative Parents
- Oxetanes / Carboxylic acid esters / Oxacyclic compounds / Monocarboxylic acids and derivatives / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
- Substituents
- Aliphatic heteromonocyclic compound / Beta_propiolactone / Carbonyl group / Carboxylic acid derivative / Carboxylic acid ester / Hydrocarbon derivative / Monocarboxylic acid or derivatives / Organic oxide / Organic oxygen compound / Organooxygen compound
- Molecular Framework
- Aliphatic heteromonocyclic compounds
- External Descriptors
- propan-3-olide (CHEBI:49073)
- Affected organisms
- Humans and other mammals
- Fungi
- Bacteria
- Various viruses
Chemical Identifiers
- UNII
- 6RC3ZT4HB0
- CAS number
- 57-57-8
- InChI Key
- VEZXCJBBBCKRPI-UHFFFAOYSA-N
- InChI
- InChI=1S/C3H4O2/c4-3-1-2-5-3/h1-2H2
- IUPAC Name
- oxetan-2-one
- SMILES
- O=C1CCO1
References
- General References
- Authors unspecified: betaPropiolactone. Rep Carcinog. 2011;12:366-7. [Article]
- Uittenbogaard JP, Zomer B, Hoogerhout P, Metz B: Reactions of beta-propiolactone with nucleobase analogues, nucleosides, and peptides: implications for the inactivation of viruses. J Biol Chem. 2011 Oct 21;286(42):36198-214. doi: 10.1074/jbc.M111.279232. Epub 2011 Aug 25. [Article]
- LOGRIPPO GA: Investigations of the use of beta-propiolactone in virus inactivation. Ann N Y Acad Sci. 1960 Jan 13;83:578-94. [Article]
- Colburn NH, Boutwell RK: The in vivo binding of beta-propiolactone to mouse skin DNA, RNA, and protein. Cancer Res. 1968 Apr;28(4):642-52. [Article]
- EPA report [Link]
- Himedialabs [Link]
- Monograph propiolactone [Link]
- Science alert [Link]
- External Links
- KEGG Drug
- D05630
- KEGG Compound
- C19297
- PubChem Compound
- 2365
- PubChem Substance
- 310265222
- ChemSpider
- 2275
- 1311565
- ChEBI
- 49073
- ChEMBL
- CHEMBL1200627
- ZINC
- ZINC000001482154
- Wikipedia
- Beta-Propiolactone
- MSDS
- Download (49.6 KB)
Clinical Trials
- Clinical Trials
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Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Liquid
- Experimental Properties
Property Value Source melting point (°C) -33.4ºC Rep Carcinog. 2011; 12:366-7 boiling point (°C) Decomposes (155ºC) 'MSDS' water solubility 370 g/L at 25ºC Rep Carcinog. 2011; 12:366-7 logP -0.564 EPA - Predicted Properties
Property Value Source Water Solubility 436.0 mg/mL ALOGPS logP -0.55 ALOGPS logP -0.14 Chemaxon logS 0.78 ALOGPS pKa (Strongest Basic) -7.1 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 1 Chemaxon Hydrogen Donor Count 0 Chemaxon Polar Surface Area 26.3 Å2 Chemaxon Rotatable Bond Count 0 Chemaxon Refractivity 15.55 m3·mol-1 Chemaxon Polarizability 6.55 Å3 Chemaxon Number of Rings 1 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 MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-05fs-9000000000-6f1067ec053d96ab5d1f Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-00di-9000000000-3f4ab9e91ad5d5e76493 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-0a4i-9000000000-906598d624f8a0fbe3fd Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-00di-9000000000-86f86ed4fdea237fc046 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-006x-9000000000-16724e93b0a63e8cdd03 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0a4i-9000000000-bb38a4a925fce30f2697 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]- 99.3798435 predictedDarkChem Lite v0.1.0 [M-H]- 99.3022435 predictedDarkChem Lite v0.1.0 [M-H]- 118.310135 predictedDeepCCS 1.0 (2019) [M+H]+ 100.2065435 predictedDarkChem Lite v0.1.0 [M+H]+ 100.2226435 predictedDarkChem Lite v0.1.0 [M+H]+ 120.20555 predictedDeepCCS 1.0 (2019) [M+Na]+ 99.8723435 predictedDarkChem Lite v0.1.0 [M+Na]+ 128.33672 predictedDeepCCS 1.0 (2019)
Targets
References
Carriers
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Binder
- General Function
- Binds water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs (Probable). Its main function is the regulation of the colloidal osmotic pressure of blood (Probable). Major zinc transporter in plasma, typically binds about 80% of all plasma zinc (PubMed:19021548). Major calcium and magnesium transporter in plasma, binds approximately 45% of circulating calcium and magnesium in plasma (By similarity). Potentially has more than two calcium-binding sites and might additionally bind calcium in a non-specific manner (By similarity). The shared binding site between zinc and calcium at residue Asp-273 suggests a crosstalk between zinc and calcium transport in the blood (By similarity). The rank order of affinity is zinc > calcium > magnesium (By similarity). Binds to the bacterial siderophore enterobactin and inhibits enterobactin-mediated iron uptake of E.coli from ferric transferrin, and may thereby limit the utilization of iron and growth of enteric bacteria such as E.coli (PubMed:6234017). Does not prevent iron uptake by the bacterial siderophore aerobactin (PubMed:6234017)
- Specific Function
- antioxidant activity
- Gene Name
- ALB
- Uniprot ID
- P02768
- Uniprot Name
- Albumin
- Molecular Weight
- 69365.94 Da
References
- Mate U, Solomon JJ, Segal A: In vitro binding of beta-propiolactone to calf thymus DNA and mouse liver DNA to form 1-(2-carboxyethyl) adenine. Chem Biol Interact. 1977 Sep;18(3):327-36. [Article]
Drug created at November 27, 2015 22:14 / Updated at February 21, 2021 18:52