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Chemistry

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Also known as: Poloxamer 188, 9003-11-6, Poloxamer 407, Pluronic f-68, 106392-12-5, 2-methyloxirane;oxirane
Molecular Formula
C5H10O2
Molecular Weight
102.13  g/mol
InChI Key
RVGRUAULSDPKGF-UHFFFAOYSA-N

Detalan
A copolymer of polyethylene and polypropylene ether glycol. It is a non-ionic polyol surface-active agent used medically as a fecal softener and in cattle for prevention of bloat.
1 2D Structure

Detalan

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
2-methyloxirane;oxirane
2.1.2 InChI
InChI=1S/C3H6O.C2H4O/c1-3-2-4-3;1-2-3-1/h3H,2H2,1H3;1-2H2
2.1.3 InChI Key
RVGRUAULSDPKGF-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CC1CO1.C1CO1
2.2 Synonyms
2.2.1 MeSH Synonyms

1. Bloat Guard

2. Oxyethylene Oxypropylene Polymer

3. Oxypropylene Polymer, Oxyethylene

4. Poloxalene 2930

5. Polymer, Oxyethylene Oxypropylene

6. Polyoxyethylene Polyoxypropylene Polyoxyethylene Polymer

7. Proxanol

8. Sk And F 18667

9. Sk And F-18667

10. Sk And F18667

11. Tergitol

12. Therabloat

2.2.2 Depositor-Supplied Synonyms

1. Poloxamer 188

2. 9003-11-6

3. Poloxamer 407

4. Pluronic F-68

5. 106392-12-5

6. 2-methyloxirane;oxirane

7. Tergitol(tm)xh(nonionic)

8. Pluronic L

9. Pluronic L 122

10. Polyethylene-polypropylene Glycol

11. Pluronic

12. Polyethylene Oxide-polypropylene Oxide

13. 691397-13-4

14. Poloxalkol

15. F-108

16. Poloxamer 331

17. Pluronic L 61

18. Pluronic L-81

19. Therabloat

20. Proxanol

21. Epan 485

22. Epan 710

23. Epan 785

24. Bloat Guard

25. Tergitol Xh

26. Oxirane, Methyl-, Polymer With Oxirane, Ether With 1,2-propanediol (2:1)

27. Pluronic L44

28. Pluronic F 38

29. Pluronic F 68

30. Pluronic F 108

31. Pluronic F 127

32. Pluronic L 101

33. Pluronic L 121

34. Pluronic L-101

35. 2-methyloxirane; Oxirane

36. Hydrowet

37. Polykol

38. Proksanol

39. Regulaid

40. Slovanik

41. Magcyl

42. Ethylene Oxide-propylene Oxide Block Polymer

43. Pluracol V

44. Pluronic F

45. Pluronic P

46. Monolan Pb

47. Pluriol Pe

48. Polyethylene Glycol, Propoxylated

49. Poloxalene L64

50. Glycols, Polyethylene-polypropylene

51. Poloxamer (nf)

52. Pluronic-68

53. Pluronic F86

54. Bsp 5000

55. Poloxamer 108

56. Poloxamer 182lf

57. Rokopol 16p

58. Rokopol 30p

59. Component Of Casakol

60. Pluronic 10r8

61. Pluronic 31r2

62. Pluronic F 68lf

63. Pluronic F 87

64. Pluronic F 88

65. Pluronic F 98

66. Pluronic L 24

67. Pluronic L 31

68. Pluronic L 35

69. Pluronic L 44

70. Pluronic L 62

71. Pluronic L 64

72. Pluronic L 68

73. Pluronic L 92

74. Pluronic L122

75. Pluronic P 75

76. Pluronic P 85

77. Pluronic P-65

78. Pluronic P-75

79. Propylen M 12

80. Proxanol 158

81. Proxanol 228

82. Slovanik 630

83. Slovanik 660

84. Supronic B 75

85. Rc 102

86. Wyandotte 7135

87. Emkalyx Ep 64

88. Emkalyx L101

89. Genapol Pf 10

90. Nixolen Sl 19

91. Rokopol 30p9

92. Tergitol Monionic Xh

93. Vepoloxamer (usan)

94. Pluronic C 121

95. Pluronic F 125

96. Pluronic P 104

97. Supronic E 400

98. Teric Pe40

99. Teric Pe60

100. Teric Pe70

101. Velvetol Oe 2nt1

102. Lutrol F (tn)

103. Newpol Pe-88

104. Nissan Pronon 201

105. Emkalyx L 101

106. Oxirane, Methyl-, Polymer With Oxirane

107. Plonon 201

108. Plonon 204

109. Pronon 102

110. Pronon 104

111. Pronon 201

112. Pronon 204

113. Pronon 208

114. Unilube 50mb26x

115. Polylon 13-5

116. Oxirane-propylene Oxide

117. Sk&f 18,667

118. Teric Pe 61

119. Teric Pe 62

120. Laprol 1502

121. Pluriol Pe 6810

122. Voranol P 2001

123. Berol Tvm 370

124. Peg-ppg-peg

125. Unilube 50mb168x

126. Monolan 8000e80

127. Niax Lg 56

128. Tergitol Xh (nonionic)

129. Thanol E 4003

130. Eban 710

131. Epan 750

132. Epon 420

133. Ppg Diol 3000eo

134. Synperonic Pe 30/40

135. Pluronic F87-a7850

136. Methyloxirane-oxirane Polymer

137. Niax 16-46

138. Oxirane-methyloxirane Polymer

139. Schembl11737

140. Pluronic L62(mw 2500)

141. Pluronic L64(mw 2900)

142. Ethylene Oxide Propylene Oxide

143. Oxirane, Polymer With Oxirane

144. Methyloxirane-oxirane Copolymer

145. Polyethylene-pluronic L-62lf

146. Propylene Oxide Ethylene Oxide

147. Tsl 431

148. Adeka Pluronic F-108

149. Polyoxyethylene Polyoxypropylene

150. Polyoxyethylene-polyoxypropylene

151. Oligoether L-1502-2-30

152. Chebi:32026

153. Polypropylene Glycol, Ethoxylated

154. Glycols, Polyethylenepolypropylene

155. Tvm 370

156. Lg 56

157. Oxirane, Polymer With Methyloxirane

158. Peg/ppg-24/34 Triblock Copolymer

159. Nsc63908

160. Poly(propylene Oxide-ethylene Oxide)

161. Polyoxyethylenated Poly(oxypropylene)

162. Nsc-63908

163. Ws 661

164. Poly(mixed Ethylene, Propylene)glycol

165. Propylene Oxide-ethylene Oxide Polymer

166. Akos015912614

167. Db11451

168. Polyoxyethylene-polyoxypropylene Polymer

169. Ethylene Glycol-propylene Glycol Polymer

170. Ethylene Oxide-propylene Oxide Copolymer

171. Propylene Oxide-ethylene Oxide Copolymer

172. Sk & F 18,667

173. Poly(oxyethylene)-poly(oxypropylene) Glycol

174. N 480

175. Poly(oxyethylene)-poly(oxypropylene) Polymer

176. Polypropylene Glycol-ethylene Oxide Copolymer

177. Propane-1,2-diol, Ethoxylated, Propoxylated

178. D01941

179. D10680

180. Polyethylene Oxide-polypropylene Oxide Copolymer

181. Polypropoxylated, Polyethoxylated Propylene Glycol

182. 1,2-propyleneglycol, Ethoxylated And Propoxylated

183. M 90/20

184. 75h90000

185. Propylene Glycol, Propylene Oxide, Ethylene Oxide Polymer

186. Oxirane, 2-methyl-, Polymer With Oxirane, Ether With 1,2-propanediol (2:1)

187. .alpha.-hydro-.omega.-hydroxypoly(oxyethylene)poly(oxypropylene)poly(oxyethylene) Block Copolymer

2.3 Create Date
2005-03-26
3 Chemical and Physical Properties
Molecular Weight 102.13 g/mol
Molecular Formula C5H10O2
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count2
Rotatable Bond Count0
Exact Mass102.068079557 g/mol
Monoisotopic Mass102.068079557 g/mol
Topological Polar Surface Area25.1 Ų
Heavy Atom Count7
Formal Charge0
Complexity36.7
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count1
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count2
4 Drug and Medication Information
4.1 Therapeutic Uses

Mechanical cleansing of a wound with a sponge soaked in a surfactant has prevented the development of experimental wound infection. The surfactant utilized for wound cleansing is Pluronic F-68 (poloxalene; I), a member of a family of block copolymers called Pluronic polyls. Long term toxicity studies and clinical trials suggest that this surfactant is safe for human use. I is a nonionic detergent that does not have any intrinsic antibacterial activity. Although mechanical cleansing with saline-soaked sponges effectively removes bacteria, it damages the wound and impairs its resistance to infection. The severity of the damage to the skin exerted by the sponge can be correlated with its porosity. Sponges with a low porosity are abrasive and exert more damage to skin than do sponges with a higher porosity. The addition of I to even the most abrasive sponges ensures that the bacterial removal efficiency of the sponge scrub is maintained, while tissue trauma is minimized. This dual effect of the surfactant results in a dramatic reduction in the infection rate of contaminated wounds.

PMID:1119685 Rodeheaver GT et al; Am J Surg 129 (3): 241-5 (1975)


(VET): Prevention of bloat in cattle.

O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. 13th Edition, Whitehouse Station, NJ: Merck and Co., Inc., 2001., p. 1357


4.2 Drug Warning

A randomized, double blind, placebo controlled, dose escalation study of the toxicity and pharmacokinetics of poloxamer 188 (RheothRx) was conducted in 36 healthy male subjects (ages 19-35 yr) who received iv injections of 10-90 mg/kg/hr poloxamer or placebo. ... The most common adverse effects were pain, injection site abnormality, and nausea. Eight subjects discontinued treatment with poloxamer due to adverse events.

PMID:9232521 Jewell RC et al; J Pharm Sci 86 (7): 808-812 (1997)


4.3 Drug Indication

Indicated to reduce viscosity in the blood before transfusions.


5 Pharmacology and Biochemistry
5.1 Pharmacology

Poloxamer 188 (P188) exerts a protective action against oxidative stress and inflammation in tissue injury in various experimental models. In the rat model of excitotoxic injury, immediate intrathecal administration of P188 reduced neuronal loss, indicated by smaller spherical excitotoxic lesions. In a murine hind-limb model, P188 mediated a protective action against ischemia-reperfusion injury as indicated by decreased myocyte injury, preserved tissue adenosine 5'-triphosphate levels, and improved survival rates, suggesting that P188 can seal defects in cell membranes and attenuate damage induced by reactive oxygen species. P188 was shown to elicit protective effects against excitotoxic injury, and trauma-induced necrotic and apoptotic cell death in cultured neurons. In the mouse stroke models, P188 exerted a neuroprotective effect in brain ischemia-reperfusion induced acute injury by significantly reducing infarct volume and water content in brain edema and ameliorating the neurological symptoms 24 h after ischemia or reperfusion injury. P188 also significantly inhibited inflammatory, coagulation, and apoptotic responses resulting from superior mesenteric artery occlusion. In the experimental model of striatum injury in rats, P188 was shown to reduce excitotoxicity-induced tissue loss and macrophage infiltrate.


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.)


Surface-Active Agents

Agents that modify interfacial tension of water; usually substances that have one lipophilic and one hydrophilic group in the molecule; includes soaps, detergents, emulsifiers, dispersing and wetting agents, and several groups of antiseptics. (See all compounds classified as Surface-Active Agents.)


Cathartics

Agents that are used to stimulate evacuation of the bowels. (See all compounds classified as Cathartics.)


5.3 Absorption, Distribution and Excretion

Absorption

Following a 48-hour continuous intravenous infusion of purified P188 in healthy volunteers, the mean concentration of P188 at steady state concentration (Css) was 522 118 mg/L and the maximum concentration occurring at the end of the loading dose was approximately 909 165 mg/L. The plasma concentrations were dose-proportional.


Route of Elimination

Renal clearance accounted for 90% of total plasma clearance in healthy male subjects.


Volume of Distribution

The volume of distribution at steady state (Vss) after a continuous intravenous infusion of 500 mg/kg of P188 on day 7 was approximately 2.13 mL/kg in pregnant female rats. Vss was 876 mL/kg in dogs receiving a dose of 720 mg/kg/day.


Clearance

Following a 48-hour continuous intravenous infusion of purified P188 in healthy volunteers, the mean total body clearance was estimated to be 4.40 0.77 L/h when using the plasma concentration data only. Estimated mean renal clearance from the amount of P-188 excreted in urine was 5.21 1.28 L/h. The clearance of a single metabolite HW1 was slower than the parent compound.


Absorption and excretion of 14C-Poloxalene 2930 (PX), a nonionic hydrophobic surfactant of large molecular weight, were studied using bile fistula rats. Approximately half of the dose infused intraduodenally was absorbed and some of the absorbed surfactant was excreted in bile. The remainder was excreted in urine. Only trace quantities of the 14C-PX were recovered in liver and carcass at termination of the study. Two studies were also performed with 14C-PX incorporated into the diet. In the first feeding study of 7 days duration, most of the agent was excreted via the gastrointestinal tract within 72 hr of discontinuing treatment. In the second study, rats were fed dietary 14C-PX for 7, 14, or 23 days to determine whether the surfactant continued to accumulate in the body as the test period was extended. Further accumulation did occur between the 7th and 14th days but not when feeding was continued for a total of 23 days. Of the amount of 14C-PX ingested after 23 days of feeding, essentially all was excreted by the end of 7 days after discontinuing treatment. These studies indicate that despite its large molecular weight of about 3,000 some 14C-PX is absorbed. Furthermore, absorbed material is promptly excreted in bile and urine with little retained in body tissues.

PMID:6149916 Rodgers JB et al; Drug Metab Dispos 12 (5): 631-4 (1984)


To investigate the distribution of poloxamer 407 (Pluronic F-127), rats received 300 mg of intraperitoneal poloxamer 407 solution; blood and urine samples were taken frequently and liver and kidney homogenates were prepared and analyzed using a colorimetry assay. Clearance was 0.014 mL/min. The mean amount excreted in the urine was 76.3 mg in 24 hr. Amounts of poloxamer 407 in supernatants of liver and kidney homogenates were 15.9 and 3.1 mg, respectively.

PMID:8738197 Li C et al; J Pharm Biomed Anal 14 (5): 659-65 (1996)


...The disposition and pharmacokinetics of Poloxamer 108 was studied in rats as an initial step towards understanding its behavior in man. After iv administration in rats, about 94% of 7 or 100 mg/kg doses of ethylene-14-C-labeled polymer was excreted in the urine in 3 days. About 6% of the label appeared in feces. Erythrocyte membranes were not permeable to the polymer, and only the parent compound was demonstrable in urine. Twenty hours after dosing, small residues were detectable only in the kidney, liver, small intestine and carcass. The 3rd phase of the plasma disappearance pattern was evident only at the larger dose, but plasma disappearance kinetics were independent of the dose in the used range. Most of Poloxamer 108 was eliminated rapidly in rats by renal excretion; a smaller portion probably was removed by biliary excretion.

PMID:1231 Jo Wang Z-Y et al; Drug Metab Dispos 3 (6): 536-42 (1975)


A randomized, double blind, placebo controlled, dose escalation study of the toxicity and pharmacokinetics of poloxamer 188 (RheothRx) was conducted in 36 healthy male subjects (ages 19-35 yr) who received iv injections of 10-90 mg/kg/hr poloxamer or placebo. Poloxamer was eliminated primarily by renal excretion. Estimates of clearance, elimination rate constant, and apparent volume of distribution at steady state were independent of infusion rate. Steady state plasma levels increased linearly with increasing infusion rate values up to 90 mg/kg/hr. Mean plasma clearance was 1.06 mL/min/kg. ...

PMID:9232521 Jewell RC et al; J Pharm Sci 86 (7): 808-812 (1997)


5.4 Metabolism/Metabolites

A single metabolite, HW1, with a molecular weight of approximately 16000 Daltons was detected in a pharmacokinetic study in dogs and man. HW1 was present in 10-20 and 40% of the parent compound at steady state in dogs and humans, respectively. However, it is suggested that block polymers are not metabolized and are excreted unchanged in the urine and feces, and HW1 may be a component of the higher molecular weight distribution of P188 that concentrates in the plasma due to its lower clearance rate.


5.5 Biological Half-Life

In humans, P188 has half-life of 18 hours. The terminal plasma elimination half-life was approximately 7.65 1.10 hours in healthy volunteers receiving a 48-hour continuous intravenous infusion of purified P188.


5.6 Mechanism of Action

P188 seals stable defects in cell membranes induced by skeletal muscle cell membranes rupture induced by ischemia-reperfusion injury, electroporation, irradiation, and heat damage. The full mechanism of action of P188 in inducing cytoprotective effects is not clear; however, based on _in vitro_ experiments and the structural similarity to plasmalemma, P188 may be directly incorporated into the phospholipid bilayer to attenuate the extent of tissue injury. Its high surface activity facilitates P188 to be inserted into lipid monolayers. P188 is proposed to exert localized actions by only interacting with damaged and compromised bilayers where the local lipid packing density is reduced. In addition to the direct interaction with the membrane, P188 was shown to inhibit MMP-9 protein levels and activity, as well as the NF-B signal pathway, in the model of acute cerebral ischemia, which is associated with increased BBB permeability leading to cerebral edema and increased penetration. MMP-9 is a key factor in extracellular matrix (ECM) degradation and BBB disruption.


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