U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C3H4O2
Molecular Weight 72.0628
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PROPIOLACTONE

SMILES

C1COC1=O

InChI

InChIKey=VEZXCJBBBCKRPI-UHFFFAOYSA-N
InChI=1S/C3H4O2/c4-3-1-2-5-3/h1-2H2

HIDE SMILES / InChI

Molecular Formula C3H4O2
Molecular Weight 72.0628
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Propiolactone (or beta-propiolactone) is a disinfectant used in vapor form to sterilize vaccines, grafts, blood plasma, surgical instruments. It has been used against bacteria, fungi, and virus. Propiolactone was first commercially available in the United States in 1958 but then was withdrawn because it was discovered that compound was a human carcinogen. The results have shown the generation of tumors in several tissues and from different administration routes. Propiolactone is a direct-acting alkylating agent that reacts with polynucleotides and DNA, mainly at N7 of guanine and N1 of adenine, to form carboxyethyl derivatives.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Inactivation of hepatitis viruses and HIV in plasma and plasma derivatives by treatment with beta-propiolactone/UV irradiation.
1989
ß-Propiolactone.
2004
The effect of chemical inactivation of bovine viral diarrhea virus with beta-propiolactone and binary ethyleneimine on plasma proteins and coagulation factors.
2004
SARS vaccine protective in mice.
2005 Aug
Ru-catalyzed alkene-alkyne coupling. Total synthesis of amphidinolide P.
2005 Dec 21
A kinetic approach to the alkylating potential of carcinogenic lactones.
2005 Jul
[Conditions for SARS-CoV cultivation and inactivation].
2005 Jun
Profile of animal bite cases in Pune.
2005 Mar
Ophiopojaponin D, a new phenylpropanoid glycoside from Ophiopogon japonicus Ker-Gawl.
2005 Nov
Immunogenicity and protective efficacy in monkeys of purified inactivated Vero-cell SARS vaccine.
2006 Feb 13
Clinical responses of patients with Kawasaki disease to different brands of intravenous immunoglobulin.
2006 Jan
Structures of heterogeneous proton-bond dimers with a high dipole moment monomer: covalent vs electrostatic interactions.
2006 May 11
[The development of mucosal vaccines].
2006 Nov 2
Influenza: the virus and prophylaxis with inactivated influenza vaccine in "at risk" groups, including COPD patients.
2007
Quantification of growth factors in allogenic bone grafts extracted with three different methods.
2007
Making a difference on excited-state chemistry by controlling free space within a nanocapsule: photochemistry of 1-(4-alkylphenyl)-3-phenylpropan-2-ones.
2007 Aug 30
Ab initio study of the reaction of propionyl (C2H5CO) radical with oxygen (O2).
2007 Aug 7
Intravaginal administration of an inactivated vaccine prevents lesions induced by caprine herpesvirus-1 in goats.
2007 Feb 19
Reactivity of indanedioneketene dimer with amines.
2007 Jan 19
Frequencies of mutagen-induced coincident mitotic recombination at unlinked loci in Saccharomyces cerevisiae.
2007 Mar 1
Harvesting and concentration of human influenza A virus produced in serum-free mammalian cell culture for the production of vaccines.
2007 May 1
Enzymatic synthesis of poly(hydroxyalkanoates) in ionic liquids.
2007 Nov 1
A sensitive cell-based assay for the detection of residual infectious West Nile virus.
2007 Sep 28
Efficiency of Matricaria chamomilla CH12 and number of doses of rabies vaccine on the humoral immune response in cattle.
2008 Dec
Validation of betapropiolactone (BPL) as an inactivant for infectious bovine rhinotracheitis (IBR) virus.
2008 Dec
The mannose receptor mediates dengue virus infection of macrophages.
2008 Feb 8
6-sulfo sialyl Lewis X is the common receptor determinant recognized by H5, H6, H7 and H9 influenza viruses of terrestrial poultry.
2008 Jul 24
Development of stable influenza vaccine powder formulations: challenges and possibilities.
2008 Jun
Chemical reactivity and biological activity of diketene.
2008 Oct
Inactivated infectious haematopoietic necrosis virus (IHNV) vaccines.
2008 Oct
Chemical addressability of ultraviolet-inactivated viral nanoparticles (VNPs).
2008 Oct 2
Serological response in cattle immunized with inactivated oil and Algel adjuvant vaccines against infectious bovine rhinotracheitis.
2009 Apr
Matrix photochemistry, photoelectron spectroscopy, solid-phase structure, and ring strain energy of beta-propiothiolactone.
2009 Apr 16
Quantitative determination of the infectivity of the proviral DNA of a retrovirus in vitro: Evaluation of methods for DNA inactivation.
2009 Aug
Pandemic influenza vaccines - the challenges.
2009 Dec
Combined experimental and theoretical study on hydrogen-bonded complexes between cyclic ketones, lactones, and lactams with 3,4-dinitrophenol.
2009 Dec 31
A pilot study of the immune response to whole inactivated avian influenza H7N1 virus vaccine in mice.
2009 Jan
Development of a potent inhibitor of 2-arachidonoylglycerol hydrolysis with antinociceptive activity in vivo.
2009 Jan
Poly(lactide-co-glycolide) microspheres: a potent oral delivery system to elicit systemic immune response against inactivated rabies virus.
2009 Mar 26
From where did the 2009 'swine-origin' influenza A virus (H1N1) emerge?
2009 Nov 24
Induction of cell-cell fusion by ectromelia virus is not inhibited by its fusion inhibitory complex.
2009 Sep 29
Seroepidemiology of pandemic influenza A (H1N1) 2009 virus infections in Pune, India.
2010 Aug 25
The influence of the inactivating agent on the antigen content of inactivated Newcastle disease vaccines assessed by the in vitro potency test.
2010 Jan
Randomised controlled double-blind non-inferiority trial of two antivenoms for saw-scaled or carpet viper (Echis ocellatus) envenoming in Nigeria.
2010 Jul 27
Vaccination with DNA plasmids expressing Gn coupled to C3d or alphavirus replicons expressing gn protects mice against Rift Valley fever virus.
2010 Jun 22
Isolation of a 2-oxetanone from the fruits of Synsepalum dulcificum.
2010 Nov
GMP-grade pneumococcal whole-cell vaccine injected subcutaneously protects mice from nasopharyngeal colonization and fatal aspiration-sepsis.
2010 Nov 3
Immunogenicity and protective efficacy in mice and hamsters of a β-propiolactone inactivated whole virus SARS-CoV vaccine.
2010 Oct
Retrospective analysis of suspected rabies cases reported at bugando referral hospital, mwanza, Tanzania.
2010 Sep
The cap'n'collar transcription factor Nrf2 mediates both intrinsic resistance to environmental stressors and an adaptive response elicited by chemopreventive agents that determines susceptibility to electrophilic xenobiotics.
2011 Jun 30
Patents
Substance Class Chemical
Created
by admin
on Sat Jun 26 01:47:22 UTC 2021
Edited
by admin
on Sat Jun 26 01:47:22 UTC 2021
Record UNII
6RC3ZT4HB0
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PROPIOLACTONE
HSDB   INN   MART.   ORANGE BOOK   USAN  
INN   USAN  
Official Name English
BETAPRONE
Brand Name English
NSC-21626
Code English
BETA-PROPIOLACTONE
Common Name English
.BETA.-PROPIOLACTONE
MI  
Common Name English
BETA-PROPIOLACTONE [IARC]
Common Name English
.BETA.-PROPIOLACTONE [MI]
Common Name English
PROPIOLACTONE [USAN]
Common Name English
PROPIOLACTONE [INN]
Common Name English
PROPIOLACTONE [ORANGE BOOK]
Common Name English
PROPIOLACTONE [HSDB]
Common Name English
PROPIOLACTONE [MART.]
Common Name English
2-OXETANONE
Systematic Name English
Classification Tree Code System Code
NCI_THESAURUS C45187
Created by admin on Sat Jun 26 01:47:22 UTC 2021 , Edited by admin on Sat Jun 26 01:47:22 UTC 2021
IARC beta-Propiolactone
NCI_THESAURUS C606
Created by admin on Sat Jun 26 01:47:22 UTC 2021 , Edited by admin on Sat Jun 26 01:47:22 UTC 2021
Code System Code Type Description
WIKIPEDIA
BETA-PROPIOLACTONE
Created by admin on Sat Jun 26 01:47:22 UTC 2021 , Edited by admin on Sat Jun 26 01:47:22 UTC 2021
PRIMARY
EPA CompTox
57-57-8
Created by admin on Sat Jun 26 01:47:22 UTC 2021 , Edited by admin on Sat Jun 26 01:47:22 UTC 2021
PRIMARY
DRUG CENTRAL
3495
Created by admin on Sat Jun 26 01:47:22 UTC 2021 , Edited by admin on Sat Jun 26 01:47:22 UTC 2021
PRIMARY
MESH
D011420
Created by admin on Sat Jun 26 01:47:22 UTC 2021 , Edited by admin on Sat Jun 26 01:47:22 UTC 2021
PRIMARY
RXCUI
1311565
Created by admin on Sat Jun 26 01:47:22 UTC 2021 , Edited by admin on Sat Jun 26 01:47:22 UTC 2021
PRIMARY RxNorm
FDA UNII
6RC3ZT4HB0
Created by admin on Sat Jun 26 01:47:22 UTC 2021 , Edited by admin on Sat Jun 26 01:47:22 UTC 2021
PRIMARY
EVMPD
SUB10109MIG
Created by admin on Sat Jun 26 01:47:22 UTC 2021 , Edited by admin on Sat Jun 26 01:47:22 UTC 2021
PRIMARY
HSDB
811
Created by admin on Sat Jun 26 01:47:22 UTC 2021 , Edited by admin on Sat Jun 26 01:47:22 UTC 2021
PRIMARY
INN
1749
Created by admin on Sat Jun 26 01:47:22 UTC 2021 , Edited by admin on Sat Jun 26 01:47:22 UTC 2021
PRIMARY
MERCK INDEX
M9204
Created by admin on Sat Jun 26 01:47:22 UTC 2021 , Edited by admin on Sat Jun 26 01:47:22 UTC 2021
PRIMARY Merck Index
PUBCHEM
2365
Created by admin on Sat Jun 26 01:47:22 UTC 2021 , Edited by admin on Sat Jun 26 01:47:22 UTC 2021
PRIMARY
DRUG BANK
DB09348
Created by admin on Sat Jun 26 01:47:22 UTC 2021 , Edited by admin on Sat Jun 26 01:47:22 UTC 2021
PRIMARY
ECHA (EC/EINECS)
200-340-1
Created by admin on Sat Jun 26 01:47:22 UTC 2021 , Edited by admin on Sat Jun 26 01:47:22 UTC 2021
PRIMARY
ChEMBL
CHEMBL1200627
Created by admin on Sat Jun 26 01:47:22 UTC 2021 , Edited by admin on Sat Jun 26 01:47:22 UTC 2021
PRIMARY
CAS
57-57-8
Created by admin on Sat Jun 26 01:47:22 UTC 2021 , Edited by admin on Sat Jun 26 01:47:22 UTC 2021
PRIMARY
NCI_THESAURUS
C44339
Created by admin on Sat Jun 26 01:47:22 UTC 2021 , Edited by admin on Sat Jun 26 01:47:22 UTC 2021
PRIMARY
Related Record Type Details
ACTIVE MOIETY