NAV

Propiolactone

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Approved, Withdrawn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
3D
Similar Structures
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
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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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Contraindications & Blackbox Warnings
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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

TargetActionsOrganism
ADNA
adduct
Humans
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
  1. Authors unspecified: betaPropiolactone. Rep Carcinog. 2011;12:366-7. [Article]
  2. 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]
  3. LOGRIPPO GA: Investigations of the use of beta-propiolactone in virus inactivation. Ann N Y Acad Sci. 1960 Jan 13;83:578-94. [Article]
  4. 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]
  5. EPA report [Link]
  6. Himedialabs [Link]
  7. Monograph propiolactone [Link]
  8. Science alert [Link]
KEGG Drug
D05630
KEGG Compound
C19297
PubChem Compound
2365
PubChem Substance
310265222
ChemSpider
2275
RxNav
1311565
ChEBI
49073
ChEMBL
CHEMBL1200627
ZINC
ZINC000001482154
Wikipedia
Beta-Propiolactone
MSDS
Download (49.6 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Liquid
Experimental Properties
PropertyValueSource
melting point (°C)-33.4ºCRep Carcinog. 2011; 12:366-7
boiling point (°C)Decomposes (155ºC)'MSDS'
water solubility370 g/L at 25ºCRep Carcinog. 2011; 12:366-7
logP-0.564EPA
Predicted Properties
PropertyValueSource
Water Solubility436.0 mg/mLALOGPS
logP-0.55ALOGPS
logP-0.14Chemaxon
logS0.78ALOGPS
pKa (Strongest Basic)-7.1Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count1Chemaxon
Hydrogen Donor Count0Chemaxon
Polar Surface Area26.3 Å2Chemaxon
Rotatable Bond Count0Chemaxon
Refractivity15.55 m3·mol-1Chemaxon
Polarizability6.55 Å3Chemaxon
Number of Rings1Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleYesChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-05fs-9000000000-6f1067ec053d96ab5d1f
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-00di-9000000000-3f4ab9e91ad5d5e76493
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4i-9000000000-906598d624f8a0fbe3fd
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-00di-9000000000-86f86ed4fdea237fc046
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-006x-9000000000-16724e93b0a63e8cdd03
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4i-9000000000-bb38a4a925fce30f2697
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-99.3798435
predicted
DarkChem Lite v0.1.0
[M-H]-99.3022435
predicted
DarkChem Lite v0.1.0
[M-H]-118.310135
predicted
DeepCCS 1.0 (2019)
[M+H]+100.2065435
predicted
DarkChem Lite v0.1.0
[M+H]+100.2226435
predicted
DarkChem Lite v0.1.0
[M+H]+120.20555
predicted
DeepCCS 1.0 (2019)
[M+Na]+99.8723435
predicted
DarkChem Lite v0.1.0
[M+Na]+128.33672
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. DNA
Kind
Nucleotide
Organism
Humans
Pharmacological action
Yes
Actions
Adduct
DNA is the molecule of heredity, as it is responsible for the genetic propagation of most inherited traits. It is a polynucleic acid that carries genetic information on cell growth, division, and function. DNA consists of two long strands of nucleotides twisted into a double helix and held together by hydrogen bonds. The sequence of nucleotides determines hereditary characteristics. Each strand serves as the template for subsequent DNA replication and as a template for mRNA production, leading to protein synthesis via ribosomes.
References
  1. Himedialabs [Link]
  2. Monograph propiolactone [Link]

Carriers

Details1. Serum albumin
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Binder
General Function
Toxic substance binding
Specific Function
Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
Gene Name
ALB
Uniprot ID
P02768
Uniprot Name
Serum albumin
Molecular Weight
69365.94 Da
References
  1. 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