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

Details

Stereochemistry ACHIRAL
Molecular Formula C3H4O2
Molecular Weight 72.0627
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 Propiolactone was first commercially available in the United States in 1958 but then was withdrawn because it was discovered that compound was a human carcinogen.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
Immunogenicity, safety and lot consistency in adults of a chromatographically purified Vero-cell rabies vaccine: a randomized, double-blind trial with human diploid cell rabies vaccine.
2001 Sep 14
beta-Propiolactone.
2002
Effect of beta propiolactone viral inactivation on alpha1 antitrypsin values.
2002 Sep
ß-Propiolactone.
2004
Augmentation of immune responses to SARS coronavirus by a combination of DNA and whole killed virus vaccines.
2005 Aug 15
Ru-catalyzed alkene-alkyne coupling. Total synthesis of amphidinolide P.
2005 Dec 21
Reactivity of lactones and GHB formation.
2005 Jan 21
Profile of animal bite cases in Pune.
2005 Mar
[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
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
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
Pandemic influenza vaccines - the challenges.
2009 Dec
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
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
GMP-grade pneumococcal whole-cell vaccine injected subcutaneously protects mice from nasopharyngeal colonization and fatal aspiration-sepsis.
2010 Nov 3
Patents
Substance Class Chemical
Created
by admin
on Fri Dec 15 16:20:38 GMT 2023
Edited
by admin
on Fri Dec 15 16:20:38 GMT 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 GMT 2023 , Edited by admin on Fri Dec 15 16:20:38 GMT 2023
IARC beta-Propiolactone
NCI_THESAURUS C606
Created by admin on Fri Dec 15 16:20:38 GMT 2023 , Edited by admin on Fri Dec 15 16:20:38 GMT 2023
Code System Code Type Description
WIKIPEDIA
BETA-PROPIOLACTONE
Created by admin on Fri Dec 15 16:20:38 GMT 2023 , Edited by admin on Fri Dec 15 16:20:38 GMT 2023
PRIMARY
NSC
21626
Created by admin on Fri Dec 15 16:20:38 GMT 2023 , Edited by admin on Fri Dec 15 16:20:38 GMT 2023
PRIMARY
EPA CompTox
DTXSID8021197
Created by admin on Fri Dec 15 16:20:38 GMT 2023 , Edited by admin on Fri Dec 15 16:20:38 GMT 2023
PRIMARY
DRUG CENTRAL
3495
Created by admin on Fri Dec 15 16:20:38 GMT 2023 , Edited by admin on Fri Dec 15 16:20:38 GMT 2023
PRIMARY
MESH
D011420
Created by admin on Fri Dec 15 16:20:38 GMT 2023 , Edited by admin on Fri Dec 15 16:20:38 GMT 2023
PRIMARY
RXCUI
1311565
Created by admin on Fri Dec 15 16:20:38 GMT 2023 , Edited by admin on Fri Dec 15 16:20:38 GMT 2023
PRIMARY RxNorm
FDA UNII
6RC3ZT4HB0
Created by admin on Fri Dec 15 16:20:38 GMT 2023 , Edited by admin on Fri Dec 15 16:20:38 GMT 2023
PRIMARY
CHEBI
49073
Created by admin on Fri Dec 15 16:20:38 GMT 2023 , Edited by admin on Fri Dec 15 16:20:38 GMT 2023
PRIMARY
EVMPD
SUB10109MIG
Created by admin on Fri Dec 15 16:20:38 GMT 2023 , Edited by admin on Fri Dec 15 16:20:38 GMT 2023
PRIMARY
HSDB
811
Created by admin on Fri Dec 15 16:20:38 GMT 2023 , Edited by admin on Fri Dec 15 16:20:38 GMT 2023
PRIMARY
INN
1749
Created by admin on Fri Dec 15 16:20:38 GMT 2023 , Edited by admin on Fri Dec 15 16:20:38 GMT 2023
PRIMARY
MERCK INDEX
m9204
Created by admin on Fri Dec 15 16:20:38 GMT 2023 , Edited by admin on Fri Dec 15 16:20:38 GMT 2023
PRIMARY Merck Index
SMS_ID
100000081358
Created by admin on Fri Dec 15 16:20:38 GMT 2023 , Edited by admin on Fri Dec 15 16:20:38 GMT 2023
PRIMARY
PUBCHEM
2365
Created by admin on Fri Dec 15 16:20:38 GMT 2023 , Edited by admin on Fri Dec 15 16:20:38 GMT 2023
PRIMARY
DRUG BANK
DB09348
Created by admin on Fri Dec 15 16:20:38 GMT 2023 , Edited by admin on Fri Dec 15 16:20:38 GMT 2023
PRIMARY
ECHA (EC/EINECS)
200-340-1
Created by admin on Fri Dec 15 16:20:38 GMT 2023 , Edited by admin on Fri Dec 15 16:20:38 GMT 2023
PRIMARY
ChEMBL
CHEMBL1200627
Created by admin on Fri Dec 15 16:20:38 GMT 2023 , Edited by admin on Fri Dec 15 16:20:38 GMT 2023
PRIMARY
CAS
57-57-8
Created by admin on Fri Dec 15 16:20:38 GMT 2023 , Edited by admin on Fri Dec 15 16:20:38 GMT 2023
PRIMARY
NCI_THESAURUS
C44339
Created by admin on Fri Dec 15 16:20:38 GMT 2023 , Edited by admin on Fri Dec 15 16:20:38 GMT 2023
PRIMARY
Related Record Type Details
ACTIVE MOIETY