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 Propiolactone was first commercially available in the United States in 1958 but then was withdrawn because it was discovered that compound was a human carcinogen.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
A vanadium/aspirin complex controlled release using a poly(beta-propiolactone) film. Effects on osteosarcoma cells.
2001
Synthesis of poly(2-methyl-3-hydroxyoctanoate) via anionic polymerization of alpha-methyl-beta-pentyl-beta-propiolactone.
2001 Fall
Inactivation of an astrovirus associated with poult enteritis mortality syndrome.
2001 Jan-Mar
[Development of of non-immunising, paraspecific vaccine from attenuated pox viruses: a new type of vaccine].
2001 May-Jun
Glycidol degrades scrapie mouse prion protein.
2001 Sep
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
Long-term follow-up of HIV-1-infected Thai patients immunized with Remune monotherapy.
2001 Sep-Oct
beta-Propiolactone.
2002
Serine and threonine beta-lactones: a new class of hepatitis A virus 3C cysteine proteinase inhibitors.
2002 Mar 8
Conformation-dependent reaction thermochemistry: study of lactones and lactone enolates in the gas phase.
2002 May 8
Inactivated SARS-CoV vaccine prepared from whole virus induces a high level of neutralizing antibodies in BALB/c mice.
2004 Jun
[Direct identification of Ophiogon japonicus (Thunb.)Ker-Gawl. from its confusable varieties by second derivative FTIR spectroscopy combined with statistics].
2004 Sep
SARS vaccine protective in mice.
2005 Aug
Reactivity of lactones and GHB formation.
2005 Jan 21
[Development of purified HFRS bivalent vaccine].
2005 Mar
Modulation of macrophage functions by sheeppox virus provides clues to understand interaction of the virus with host immune system.
2005 Mar 22
Role of activation function domain-1, DNA binding, and coactivator GRIP1 in the expression of partial agonist activity of glucocorticoid receptor-antagonist complexes.
2005 Mar 8
Ophiopojaponin D, a new phenylpropanoid glycoside from Ophiopogon japonicus Ker-Gawl.
2005 Nov
[The development of mucosal vaccines].
2006 Nov 2
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
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
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
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
Induction of cell-cell fusion by ectromelia virus is not inhibited by its fusion inhibitory complex.
2009 Sep 29
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
Retrospective analysis of suspected rabies cases reported at bugando referral hospital, mwanza, Tanzania.
2010 Sep
Patents
Substance Class Chemical
Created
by admin
on Fri Dec 16 19:56:07 UTC 2022
Edited
by admin
on Fri Dec 16 19:56:07 UTC 2022
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
?-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 16 19:56:07 UTC 2022 , Edited by admin on Fri Dec 16 19:56:07 UTC 2022
IARC beta-Propiolactone
NCI_THESAURUS C606
Created by admin on Fri Dec 16 19:56:07 UTC 2022 , Edited by admin on Fri Dec 16 19:56:07 UTC 2022
Code System Code Type Description
WIKIPEDIA
BETA-PROPIOLACTONE
Created by admin on Fri Dec 16 19:56:07 UTC 2022 , Edited by admin on Fri Dec 16 19:56:07 UTC 2022
PRIMARY
NSC
21626
Created by admin on Fri Dec 16 19:56:07 UTC 2022 , Edited by admin on Fri Dec 16 19:56:07 UTC 2022
PRIMARY
EPA CompTox
DTXSID8021197
Created by admin on Fri Dec 16 19:56:07 UTC 2022 , Edited by admin on Fri Dec 16 19:56:07 UTC 2022
PRIMARY
DRUG CENTRAL
3495
Created by admin on Fri Dec 16 19:56:07 UTC 2022 , Edited by admin on Fri Dec 16 19:56:07 UTC 2022
PRIMARY
MESH
D011420
Created by admin on Fri Dec 16 19:56:07 UTC 2022 , Edited by admin on Fri Dec 16 19:56:07 UTC 2022
PRIMARY
RXCUI
1311565
Created by admin on Fri Dec 16 19:56:07 UTC 2022 , Edited by admin on Fri Dec 16 19:56:07 UTC 2022
PRIMARY RxNorm
FDA UNII
6RC3ZT4HB0
Created by admin on Fri Dec 16 19:56:07 UTC 2022 , Edited by admin on Fri Dec 16 19:56:07 UTC 2022
PRIMARY
DAILYMED
6RC3ZT4HB0
Created by admin on Fri Dec 16 19:56:07 UTC 2022 , Edited by admin on Fri Dec 16 19:56:07 UTC 2022
PRIMARY
CHEBI
49073
Created by admin on Fri Dec 16 19:56:07 UTC 2022 , Edited by admin on Fri Dec 16 19:56:07 UTC 2022
PRIMARY
EVMPD
SUB10109MIG
Created by admin on Fri Dec 16 19:56:07 UTC 2022 , Edited by admin on Fri Dec 16 19:56:07 UTC 2022
PRIMARY
HSDB
811
Created by admin on Fri Dec 16 19:56:07 UTC 2022 , Edited by admin on Fri Dec 16 19:56:07 UTC 2022
PRIMARY
INN
1749
Created by admin on Fri Dec 16 19:56:07 UTC 2022 , Edited by admin on Fri Dec 16 19:56:07 UTC 2022
PRIMARY
MERCK INDEX
M9204
Created by admin on Fri Dec 16 19:56:07 UTC 2022 , Edited by admin on Fri Dec 16 19:56:07 UTC 2022
PRIMARY Merck Index
PUBCHEM
2365
Created by admin on Fri Dec 16 19:56:07 UTC 2022 , Edited by admin on Fri Dec 16 19:56:07 UTC 2022
PRIMARY
DRUG BANK
DB09348
Created by admin on Fri Dec 16 19:56:07 UTC 2022 , Edited by admin on Fri Dec 16 19:56:07 UTC 2022
PRIMARY
ECHA (EC/EINECS)
200-340-1
Created by admin on Fri Dec 16 19:56:07 UTC 2022 , Edited by admin on Fri Dec 16 19:56:07 UTC 2022
PRIMARY
ChEMBL
CHEMBL1200627
Created by admin on Fri Dec 16 19:56:07 UTC 2022 , Edited by admin on Fri Dec 16 19:56:07 UTC 2022
PRIMARY
CAS
57-57-8
Created by admin on Fri Dec 16 19:56:07 UTC 2022 , Edited by admin on Fri Dec 16 19:56:07 UTC 2022
PRIMARY
NCI_THESAURUS
C44339
Created by admin on Fri Dec 16 19:56:07 UTC 2022 , Edited by admin on Fri Dec 16 19:56:07 UTC 2022
PRIMARY
Related Record Type Details
ACTIVE MOIETY