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Details

Stereochemistry ACHIRAL
Molecular Formula C3H4O2
Molecular Weight 72.0627
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PROPIOLACTONE

SMILES

O=C1CCO1

InChI

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

HIDE SMILES / InChI

Molecular Formula C3H4O2
Molecular Weight 72.0627
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 Propiolactone was first commercially available in the United States in 1958 but then was withdrawn because it was discovered that compound was a human carcinogen.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
[Clinical trial of YU BHK Rabivak vaccine against rabies in volunteers].
2001
Inactivation of an astrovirus associated with poult enteritis mortality syndrome.
2001 Jan-Mar
Long-term follow-up of HIV-1-infected Thai patients immunized with Remune monotherapy.
2001 Sep-Oct
beta-Propiolactone.
2002
Effect of beta propiolactone viral inactivation on alpha1 antitrypsin values.
2002 Sep
Platelet adhesion onto segmented polyurethane surfaces modified by carboxybetaine.
2003
Development of a non-immunising, paraspecific vaccine from attenuated pox viruses: a new type of vaccine.
2003 Jan
ß-Propiolactone.
2004
Establishment of batch 4 of the Biological Reference Preparation (BRP) for rabies vaccine (inactivated) for veterinary use.
2004 Dec
In vitro inactivation of the rabies virus by ascorbic acid.
2004 Jan
SARS vaccine protective in mice.
2005 Aug
A kinetic approach to the alkylating potential of carcinogenic lactones.
2005 Jul
Modulation of macrophage functions by sheeppox virus provides clues to understand interaction of the virus with host immune system.
2005 Mar 22
Clinical responses of patients with Kawasaki disease to different brands of intravenous immunoglobulin.
2006 Jan
[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
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
Development of stable influenza vaccine powder formulations: challenges and possibilities.
2008 Jun
Chemical addressability of ultraviolet-inactivated viral nanoparticles (VNPs).
2008 Oct 2
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
Development of a potent inhibitor of 2-arachidonoylglycerol hydrolysis with antinociceptive activity in vivo.
2009 Jan
From where did the 2009 'swine-origin' influenza A virus (H1N1) emerge?
2009 Nov 24
Safety and efficacy of an inactivated Carbopol-adjuvanted goose haemorrhagic polyomavirus vaccine for domestic geese.
2010 Apr
Seroepidemiology of pandemic influenza A (H1N1) 2009 virus infections in Pune, India.
2010 Aug 25
Randomised controlled double-blind non-inferiority trial of two antivenoms for saw-scaled or carpet viper (Echis ocellatus) envenoming in Nigeria.
2010 Jul 27
Molecular identification of the vaccine strain from the inactivated oil emulsion H9N2 low pathogenic avian influenza vaccine.
2010 Jun
Receptor specificity and transmission of H2N2 subtype viruses isolated from the pandemic of 1957.
2010 Jun 21
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
Hemagglutinin displayed baculovirus protects against highly pathogenic influenza.
2010 Oct 4
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 Fri Dec 15 16:20:38 UTC 2023
Edited
by admin
on Fri Dec 15 16:20:38 UTC 2023
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
β-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 Fri Dec 15 16:20:38 UTC 2023 , Edited by admin on Fri Dec 15 16:20:38 UTC 2023
IARC beta-Propiolactone
NCI_THESAURUS C606
Created by admin on Fri Dec 15 16:20:38 UTC 2023 , Edited by admin on Fri Dec 15 16:20:38 UTC 2023
Code System Code Type Description
WIKIPEDIA
BETA-PROPIOLACTONE
Created by admin on Fri Dec 15 16:20:38 UTC 2023 , Edited by admin on Fri Dec 15 16:20:38 UTC 2023
PRIMARY
NSC
21626
Created by admin on Fri Dec 15 16:20:38 UTC 2023 , Edited by admin on Fri Dec 15 16:20:38 UTC 2023
PRIMARY
EPA CompTox
DTXSID8021197
Created by admin on Fri Dec 15 16:20:38 UTC 2023 , Edited by admin on Fri Dec 15 16:20:38 UTC 2023
PRIMARY
DRUG CENTRAL
3495
Created by admin on Fri Dec 15 16:20:38 UTC 2023 , Edited by admin on Fri Dec 15 16:20:38 UTC 2023
PRIMARY
MESH
D011420
Created by admin on Fri Dec 15 16:20:38 UTC 2023 , Edited by admin on Fri Dec 15 16:20:38 UTC 2023
PRIMARY
RXCUI
1311565
Created by admin on Fri Dec 15 16:20:38 UTC 2023 , Edited by admin on Fri Dec 15 16:20:38 UTC 2023
PRIMARY RxNorm
FDA UNII
6RC3ZT4HB0
Created by admin on Fri Dec 15 16:20:38 UTC 2023 , Edited by admin on Fri Dec 15 16:20:38 UTC 2023
PRIMARY
CHEBI
49073
Created by admin on Fri Dec 15 16:20:38 UTC 2023 , Edited by admin on Fri Dec 15 16:20:38 UTC 2023
PRIMARY
EVMPD
SUB10109MIG
Created by admin on Fri Dec 15 16:20:38 UTC 2023 , Edited by admin on Fri Dec 15 16:20:38 UTC 2023
PRIMARY
HSDB
811
Created by admin on Fri Dec 15 16:20:38 UTC 2023 , Edited by admin on Fri Dec 15 16:20:38 UTC 2023
PRIMARY
INN
1749
Created by admin on Fri Dec 15 16:20:38 UTC 2023 , Edited by admin on Fri Dec 15 16:20:38 UTC 2023
PRIMARY
MERCK INDEX
m9204
Created by admin on Fri Dec 15 16:20:38 UTC 2023 , Edited by admin on Fri Dec 15 16:20:38 UTC 2023
PRIMARY Merck Index
SMS_ID
100000081358
Created by admin on Fri Dec 15 16:20:38 UTC 2023 , Edited by admin on Fri Dec 15 16:20:38 UTC 2023
PRIMARY
PUBCHEM
2365
Created by admin on Fri Dec 15 16:20:38 UTC 2023 , Edited by admin on Fri Dec 15 16:20:38 UTC 2023
PRIMARY
DRUG BANK
DB09348
Created by admin on Fri Dec 15 16:20:38 UTC 2023 , Edited by admin on Fri Dec 15 16:20:38 UTC 2023
PRIMARY
ECHA (EC/EINECS)
200-340-1
Created by admin on Fri Dec 15 16:20:38 UTC 2023 , Edited by admin on Fri Dec 15 16:20:38 UTC 2023
PRIMARY
ChEMBL
CHEMBL1200627
Created by admin on Fri Dec 15 16:20:38 UTC 2023 , Edited by admin on Fri Dec 15 16:20:38 UTC 2023
PRIMARY
CAS
57-57-8
Created by admin on Fri Dec 15 16:20:38 UTC 2023 , Edited by admin on Fri Dec 15 16:20:38 UTC 2023
PRIMARY
NCI_THESAURUS
C44339
Created by admin on Fri Dec 15 16:20:38 UTC 2023 , Edited by admin on Fri Dec 15 16:20:38 UTC 2023
PRIMARY
Related Record Type Details
ACTIVE MOIETY