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AM20020040
Also known as: 2-oxetanone, Propiolactone, 57-57-8, Oxetan-2-one, Betaprone, Propanolide
Molecular Formula
C3H4O2
Molecular Weight
72.06  g/mol
InChI Key
VEZXCJBBBCKRPI-UHFFFAOYSA-N
FDA UNII
6RC3ZT4HB0

Disinfectant used in vapor form to sterilize vaccines, grafts, etc. The vapor is very irritating and the liquid form is carcinogenic.
1 2D Structure

AM20020040

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
oxetan-2-one
2.1.2 InChI
InChI=1S/C3H4O2/c4-3-1-2-5-3/h1-2H2
2.1.3 InChI Key
VEZXCJBBBCKRPI-UHFFFAOYSA-N
2.1.4 Canonical SMILES
C1COC1=O
2.2 Other Identifiers
2.2.1 UNII
6RC3ZT4HB0
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Beta Propiolactone

2. Propanolide

3. Propiolactone

2.3.2 Depositor-Supplied Synonyms

1. 2-oxetanone

2. Propiolactone

3. 57-57-8

4. Oxetan-2-one

5. Betaprone

6. Propanolide

7. 3-propanolide

8. 1,3-propiolactone

9. 3-propiolactone

10. Beta-propionolactone

11. .beta.-propiolactone

12. Beta-propiolakton

13. Hydracrylic Acid Beta-lactone

14. 3-hydroxypropionic Acid Lactone

15. Propiolactona

16. Propiolactonum

17. Beta-propanoic Acid Lactone

18. Betapron

19. Nsc-21626

20. .beta.-proprolactone

21. Bpl

22. .beta.-propionolactone

23. Propiolactone .beta.-

24. 3-hydroxypropionic Acid Beta-lactone

25. 6rc3zt4hb0

26. Beta-lactone Hydracrylic Acid

27. .beta.-propanoic Acid Lactone

28. Hydracrylic Acid .beta.-lactone

29. 3-hydroxypropionic Acid, Lactone

30. Chebi:49073

31. Nsc21626

32. Ncgc00090802-01

33. Propiolattone

34. B-propiolactone

35. Beta-proprolactone

36. Caswell No. 709

37. Propiolattone [dcit]

38. Propionolactone

39. Oxetanone

40. Beta-propiolakton [czech]

41. Propiolactonum [inn-latin]

42. Nsc 21626

43. Propiolactona [inn-spanish]

44. Ccris 536

45. Hsdb 811

46. Propiolactone, Beta-

47. Propiolactone [usan:inn:ban]

48. Einecs 200-340-1

49. Unii-6rc3zt4hb0

50. Epa Pesticide Chemical Code 010901

51. Brn 0001360

52. Propanoic Acid, 3-hydroxy-, Beta-lactone

53. Propionic Acid, 3-hydroxy-, Beta-lactone

54. Ai3-24257

55. Oxetan-2one

56. 2-oxooxetane

57. 2-oxacyclobutanone

58. Betaprone (tn)

59. .beta.-propiolakton

60. Mfcd00005169

61. .beta.-propriolactone

62. Spectrum_000216

63. Spectrum2_001982

64. Spectrum4_001274

65. Wln: T4ovtj

66. Dsstox_cid_1197

67. Ec 200-340-1

68. Hydracrylic Acid Ss-lactone

69. Propiolactone [inn]

70. Propiolactone (usan/inn)

71. Dsstox_rid_76006

72. Propiolactone [hsdb]

73. Propiolactone [usan]

74. Dsstox_gsid_21197

75. Kbiogr_001888

76. Kbioss_000696

77. 5-17-09-00003 (beilstein Handbook Reference)

78. Divk1c_001003

79. Propiolactone [mart.]

80. Spectrum1503234

81. Spbio_002163

82. Hydracylic Acid, .beta.lactone

83. .beta.-lactone Hydracrylic Acid

84. Propanoic Acid, .beta.-lactone

85. Propionic Acid, .beta.-lactone

86. Chembl1200627

87. Dtxsid8021197

88. Hms503i07

89. Kbio1_001003

90. Kbio2_000696

91. Kbio2_003264

92. Kbio2_005832

93. Beta-propiolactone [iarc]

94. Hydracrylic Acid, .beta.-lactone

95. Beta-hydroxypropionic Acid Lactone

96. Ninds_001003

97. Hms1922k19

98. Hms2092p12

99. Pharmakon1600-01503234

100. .beta.-propiolactone [mi]

101. Propiolactone [orange Book]

102. Bcp07366

103. Zinc1482154

104. Tox21_111026

105. Ccg-39865

106. Nsc758422

107. Akos015906936

108. (2s)-2-amino-3-hydroxy-propanoicacid

109. 3-hydroxypropionic Acid .beta.-lactone

110. At19319

111. Db09348

112. Nsc-758422

113. Beta-propiolactone, Grade Ii, >=90%

114. Cas-57-57-8

115. Idi1_001003

116. Ncgc00090802-02

117. Ncgc00090802-03

118. Bp-31191

119. Sbi-0051797.p002

120. Db-003748

121. Am20020040

122. Ft-0622937

123. H0168

124. Propanoic Acid, 3-hydroxy-, .beta.-lactone

125. Propionic Acid, 3-hydroxy-, .beta.-lactone

126. C19297

127. D05630

128. Ab00052333_02

129. A936942

130. Q420715

131. Sr-05000001970

132. Sr-05000001970-1

133. 25037-58-5

2.4 Create Date
2005-03-25
3 Chemical and Physical Properties
Molecular Weight 72.06 g/mol
Molecular Formula C3H4O2
XLogP3-0.2
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count2
Rotatable Bond Count0
Exact Mass72.021129366 g/mol
Monoisotopic Mass72.021129366 g/mol
Topological Polar Surface Area26.3 Ų
Heavy Atom Count5
Formal Charge0
Complexity57.9
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Warning

Because production of skin cancer is felt to be the overriding consideration in the toxic potential of BPL, all contact with liquid BPL should be avoided.

American Conference of Governmental Industrial Hygienists. Documentation of the Threshold Limit Values and Biological Exposure Indices. 5th ed. Cincinnati, OH: American Conference of Governmental Industrial Hygienists, 1986., p. 497


4.2 Drug Indication

Propiolactone was used for vaccines, tissue grafts, surgical instruments, and enzymes, as a sterilant of blood plasma, water, milk and nutrient broth as a vapor-phase disinfectant in enclosed spaces. Its sporicidal action is used against vegetative bacteria, pathologic fungi, and viruses. It is no longer used in medical procedures or in food.


5 Pharmacology and Biochemistry
5.1 Pharmacology

When employed under conditions of maximum effectiveness, propiolactone is approximately 25 more active as a vapor phase disinfectant than formaldehyde, 4000 times more active than ethylene oxide and 50000 times more active than methyl bromide. It has been shown to be mutagenic by inducing cell transformation, chromosomal aberrations and chromatoid exchange. Propiolactone has been shown to be mutagenic in both somatic and germ cells.


5.2 MeSH Pharmacological Classification

Disinfectants

Substances used on inanimate objects that destroy harmful microorganisms or inhibit their activity. Disinfectants are classed as complete, destroying SPORES as well as vegetative forms of microorganisms, or incomplete, destroying only vegetative forms of the organisms. They are distinguished from ANTISEPTICS, which are local anti-infective agents used on humans and other animals. (From Hawley's Condensed Chemical Dictionary, 11th ed) (See all compounds classified as Disinfectants.)


5.3 Absorption, Distribution and Excretion

THE LD50 BY SKIN APPLICATION IS LESS THAN 5 ML/KG IN THE GUINEA PIG, INDICATING CONSIDERABLE ABSORPTION.

Patty, F. (ed.). Industrial Hygiene and Toxicology: Volume II: Toxicology. 2nd ed. New York: Interscience Publishers, 1963., p. 1834


BETA-PROPIOLACTONE BINDS IN VIVO TO DNA, RNA & PROTEINS OF MOUSE SKIN. DEGREE OF TUMOR-INITIATING ACTIVITY IS PROPORTIONAL TO EXTENT OF DNA BINDING BUT NOT TO EXTENT OF RNA OR PROTEIN-BINDING. MAJOR RNA & DNA BINDING PRODUCT IS 7-(2-CARBOXYETHYL)GUANINE. S-2-CARBOXYETHYLCYSTEINE ... FOUND IN ACID HYDROLYSATE OF PROTEIN ... .

IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V4 265 (1974)


5.4 Metabolism/Metabolites

Propiolactone is completely hydrolyzed after 3 hours of being in an aqueous solution and this time can be even faster in the presence of cellular debris and cell culture media. When in water, the lactone ring opens at the alkyl and acyl bonds. The degradation products of propiolactone are not toxic.


BETA-PROPIOLACTONE CAN REACT WITH CHLORIDE ION TO FORM 3-CHLOROPROPIONIC ACID, ESPECIALLY IN BLOOD PLASMA.

IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V4 265 (1974)


BETA-HYDROXYPROPIONIC ACID, THE HYDROLYSIS PRODUCT OF BETA-PROPIOLACTONE, FAILED TO PRODUCE EITHER LOCAL SARCOMAS IN SC STUDY IN RATS ... OR SKIN TUMORS AFTER APPLICATIONS TO SKIN OF MICE.

IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V4 265 (1974)


5.5 Biological Half-Life

The half-life of propiolactone in water is of 225 minutes.


No reports found; [TDR, p. 1048]

TDR - Ryan RP, Terry CE, Leffingwell SS (eds). Toxicology Desk Reference: The Toxic Exposure and Medical Monitoring Index, 5th Ed. Washington DC: Taylor & Francis, 1999., p. 1048


5.6 Mechanism of Action

Propiolactone is an alkylating agent that acts through alkylation of carboxyl- and hydroxyl- groups. The lactone ring splits either at the first or third carbon. Propiolactone reacts with polynucleotides and DNA, mainly at N7 of guanine and N1 of adenine to form carboxyethyl derivatives. It also forms adducts with N3 of cytosine and thymine.


Chemical mutagens 6-N-hydroxylaminopurine and propiolactone induce Lys2 mutants with high frequency in diploid yeast Saccharomyces cerevisiae. 6-N-hydroxylaminopurine induces such mutants even in tetraploid strains. The genetic analysis of mutants was performed. It is known that propiolactone induces mutants by means of mutation-mitotic segregation mechanism, while 6-N-hydroxylaminopurine induces mutants through novel mechamism both allele mutation. Manifestation of such mechanism is the null fertility after meiosis of diploid mutants induced by 6-N-hydroxylaminopurine.

PMID:3069577 Pavlov IuI et al; Genetika 24 (10): 1752-60 (1988)


Reactivity of beta-propiolactone, beta-butyrolactone and gamma-butyrolactone with guanosine, RNA, DNA and 4-(p-nitrobenzyl)pyridine was studied. beta-Propiolactone was 50 to 100 times more reactive with all the nucleophiles than beta-butyrolactone whereas gamma-butyrolactone was completely inactive. The rate of alkylation by lactones was guanosine greater than RNA= denatured DNA greater than double-stranded DNA. The type of the adducts formed were characterized by fluorescence and ultraviolet spectroscopy. Similar alkylation products were formed by the two lactones. The main sites alkylated were N-1 at adenosine, N-3 at cytidine and N-7 at guanosine. The results suggest that the carcinogenic potency of the lactones correlates with their reactivity rather than with specificity of the adducts formed.

PMID:6161710 Hemminki K; Chem Biol Interact 34 (3): 323-31 (1981)


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