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 Propiolactone was first commercially available in the United States in 1958 but then was withdrawn because it was discovered that compound was a human carcinogen.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
Serine and threonine beta-lactones: a new class of hepatitis A virus 3C cysteine proteinase inhibitors.
2002 Mar 8
ß-Propiolactone.
2004
[Development of purified HFRS bivalent vaccine].
2005 Mar
Ophiopojaponin D, a new phenylpropanoid glycoside from Ophiopogon japonicus Ker-Gawl.
2005 Nov
Efficiency of Matricaria chamomilla CH12 and number of doses of rabies vaccine on the humoral immune response in cattle.
2008 Dec
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
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
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
The influence of the inactivating agent on the antigen content of inactivated Newcastle disease vaccines assessed by the in vitro potency test.
2010 Jan
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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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