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
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 Propiolactone was first commercially available in the United States in 1958 but then was withdrawn because it was discovered that compound was a human carcinogen.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
Glycidol degrades scrapie mouse prion protein.
2001 Sep
Long-term follow-up of HIV-1-infected Thai patients immunized with Remune monotherapy.
2001 Sep-Oct
beta-Propiolactone.
2002
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
Vero-cell rabies vaccine produced using serum-free medium.
2004 Dec 9
SARS vaccine protective in mice.
2005 Aug
Ru-catalyzed alkene-alkyne coupling. Total synthesis of amphidinolide P.
2005 Dec 21
Anticomplementary activity of equine whole IgG antivenoms: comparison of three fractionation protocols.
2005 Jan
A kinetic approach to the alkylating potential of carcinogenic lactones.
2005 Jul
Profile of animal bite cases in Pune.
2005 Mar
[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
Clinical responses of patients with Kawasaki disease to different brands of intravenous immunoglobulin.
2006 Jan
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
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
Frequencies of mutagen-induced coincident mitotic recombination at unlinked loci in Saccharomyces cerevisiae.
2007 Mar 1
Inactivated infectious haematopoietic necrosis virus (IHNV) vaccines.
2008 Oct
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
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
Molecular identification of the vaccine strain from the inactivated oil emulsion H9N2 low pathogenic avian influenza vaccine.
2010 Jun
GMP-grade pneumococcal whole-cell vaccine injected subcutaneously protects mice from nasopharyngeal colonization and fatal aspiration-sepsis.
2010 Nov 3
Patents
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