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Prestwick3_000033
Also known as: Diprophylline, 479-18-5, 7-(2,3-dihydroxypropyl)theophylline, Lufyllin, Neothylline, Diprophyllin
Molecular Formula
C10H14N4O4
Molecular Weight
254.24  g/mol
InChI Key
KSCFJBIXMNOVSH-UHFFFAOYSA-N
FDA UNII
263T0E9RR9

A THEOPHYLLINE derivative with broncho- and vasodilator properties. It is used in the treatment of asthma, cardiac dyspnea, and bronchitis.
1 2D Structure

Prestwick3_000033

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
7-(2,3-dihydroxypropyl)-1,3-dimethylpurine-2,6-dione
2.1.2 InChI
InChI=1S/C10H14N4O4/c1-12-8-7(9(17)13(2)10(12)18)14(5-11-8)3-6(16)4-15/h5-6,15-16H,3-4H2,1-2H3
2.1.3 InChI Key
KSCFJBIXMNOVSH-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CN1C2=C(C(=O)N(C1=O)C)N(C=N2)CC(CO)O
2.2 Other Identifiers
2.2.1 UNII
263T0E9RR9
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Dihydroxypropyltheophylline

2. Dilin

3. Diphylline

4. Diprophylline

5. Dylix

6. Lufyllin

7. Neothylline

2.3.2 Depositor-Supplied Synonyms

1. Diprophylline

2. 479-18-5

3. 7-(2,3-dihydroxypropyl)theophylline

4. Lufyllin

5. Neothylline

6. Diprophyllin

7. Glyphylline

8. Aristophyllin

9. Diprofilline

10. Dipropylline

11. Neutrafillina

12. Neutraphyllin

13. Neutraphylline

14. Neutroxantina

15. Propyphyllin

16. Protheophylline

17. Synthophylline

18. Corphyllin

19. Diprofillin

20. Glyphyllin

21. Neophyllin

22. Neophyl

23. Dilor

24. Hidroxiteofillina

25. Neostenovasan

26. Silbephylline

27. Asthmolysin

28. Astrophyllin

29. Coronarin

30. Glyfyllin

31. Hiphyllin

32. Hyphylline

33. Liactemin

34. Neotilina

35. Neutrafil

36. Purifilin

37. Silbephyllin

38. Solufilin

39. Solufyllin

40. Soluphyllin

41. Thefylan

42. Circain

43. Coronal

44. Droxine

45. Dyflex

46. Neufil

47. Tefilan

48. Teofen

49. Theal

50. Neo-vasophylline

51. Cor-theophylline

52. Afi-phyllin

53. Dihydroxypropyl Theophylline

54. Diprophyllinum

55. Diprofilina

56. Dihydroxypropyl Theopylin

57. (1,2-dihydroxy-3-propyl)thiophyllin

58. Iphyllin

59. 7-(2,3-dihydroxypropyl)-1,3-dimethylxanthine

60. 7-(2,3-dihydroxypropyl)-1,3-dimethylpurine-2,6-dione

61. 7-(2,3-dioxypropyl)theophylline

62. 7-(beta,gamma-dihydroxypropyl)theophylline

63. Dyphilline

64. 1,3-dimethyl-7-(2,3-dihydroxypropyl)xanthine

65. Mfcd00005759

66. 7-(2,3-dihydroxypropyl)-1,3-dimethyl-3,7-dihydro-1h-purine-2,6-dione

67. Dyphylline (usp)

68. Dyphylline [usp]

69. 7-[2,3-dihydroxypropyl]-theophylline

70. 1h-purine-2,6-dione, 7-(2,3-dihydroxypropyl)-3,7-dihydro-1,3-dimethyl-

71. Diprophylline [inn]

72. 7-(2,3-dihydroxypropyl)-3,7-dihydro-1,3-dimethyl-1h-purine-2,6-dione

73. (+-)-7-(2,3-dihydroxypropyl)theophylline

74. Nsc-14305

75. Mls000069403

76. Chebi:4728

77. Astmamasit

78. Glyphyllinum

79. Isophyllen

80. Circair

81. Tesfen

82. Theal Ampules

83. Neophyllin M

84. 263t0e9rr9

85. 7-(2,3-dihydroxypropyl)-1,3-dimethyl-1h-purine-2,6(3h,7h)-dione

86. Diphyllin (van)

87. Diprofillina

88. Smr000059068

89. Diprofillina [dcit]

90. (+/-)-7-(2,3-dihydroxypropyl)theophylline

91. Dilor-400

92. Dsstox_cid_2975

93. 7-(2,3-dimethylxanthine

94. Dsstox_rid_76813

95. Dsstox_gsid_22975

96. 1,3-dihydroxypropyl)xanthine

97. Diprofilina [inn-spanish]

98. Diprophyllinum [inn-latin]

99. Theophylline,3-dihydroxypropyl)-

100. Dihydroxypropyl Theopylin (german)

101. 7-(2,3-dihydroxypropyl)-theophylline

102. Lufyllin (tn)

103. (+-)-dyphylline

104. (+-)-diprophylline

105. Hsdb 3322

106. 7-(.beta.,.gamma.-dihydroxypropyl)theophylline

107. Wln: T56 Bn Dn Fnvnvj B1yq1q F1 H1

108. Sr-01000002972

109. Einecs 207-526-1

110. Nsc 14305

111. Diprophylline (jan/inn)

112. Brn 0284563

113. Theophylline, 7-(2,3-dihydroxypropyl)-

114. Unii-263t0e9rr9

115. 1h-purine-2, 7-(2,3-dihydroxypropyl)-3,7-dihydro-1,3-dimethyl-

116. Ncgc00016455-01

117. Diprophylline,(s)

118. 1h-purine-2,6-dione, 7-(2,3-dihydroxypropyl)-3,7-dihydro-1,3-dimethyl

119. Cas-479-18-5

120. Prestwick_465

121. Dyphylline (dilor)

122. (+/-)-dyphylline

123. (+/-)-diprophylline

124. Spectrum_000809

125. Dyphylline [mi]

126. Opera_id_1754

127. Prestwick0_000033

128. Prestwick1_000033

129. Prestwick2_000033

130. Prestwick3_000033

131. Spectrum2_000090

132. Spectrum3_000411

133. Spectrum4_000530

134. Spectrum5_000953

135. Dyphylline [hsdb]

136. Dyphylline [inci]

137. Dyphylline [vandf]

138. 7-(2,3-dihydroxypropyl)-1,3-dimethyl-2,3,6,7-tetrahydro-1h-purine-2,6-dione

139. Diprophylline [jan]

140. Schembl8192

141. Chembl1752

142. Dyphylline [usp-rs]

143. Oprea1_363458

144. Bspbio_000125

145. Bspbio_001962

146. Kbiogr_001139

147. Kbioss_001289

148. 5-26-14-00070 (beilstein Handbook Reference)

149. Mls001076466

150. Diprophylline [mart.]

151. Divk1c_000022

152. Spectrum1500269

153. Spbio_000020

154. Spbio_002046

155. Diprophylline [who-dd]

156. Bpbio1_000139

157. Gtpl7070

158. Dtxsid6022975

159. Dyphylline [orange Book]

160. Bdbm82016

161. Hms500b04

162. Kbio1_000022

163. Kbio2_001289

164. Kbio2_003857

165. Kbio2_006425

166. Kbio3_001182

167. Kscfjbixmnovsh-uhfffaoysa-

168. Ninds_000022

169. Dyphylline [usp Monograph]

170. Hms1568g07

171. Hms1920k08

172. Hms2091b13

173. Hms2095g07

174. Hms2232k09

175. Hms3372h13

176. Hms3654d18

177. Hms3712g07

178. Hms3884e19

179. Pharmakon1600-01500269

180. Bcp02003

181. Hy-b0128

182. Nsc_3182

183. Nsc14305

184. Nsc40844

185. Diprophylline [ep Monograph]

186. Tox21_110444

187. Ac7833

188. Bbl009638

189. Ccg-38906

190. Nsc-40844

191. Nsc756753

192. S1504

193. Stk796769

194. Akos005203076

195. Tox21_110444_1

196. Bcp9000631

197. Cs-1901

198. Db00651

199. Nsc-756753

200. 1h-purine-2,6-dione, 7-(2,3-dihydroxypropyl)-3,7-dihydro-1,3-dimethyl-, (+-)-

201. Idi1_000022

202. Smp1_000108

203. Ncgc00018099-02

204. Ncgc00018099-03

205. Ncgc00018099-04

206. Ncgc00018099-05

207. Ncgc00018099-06

208. Ncgc00018099-09

209. Ncgc00018099-10

210. Ncgc00089736-02

211. Ncgc00089736-03

212. Ncgc00178894-01

213. Ncgc00178894-02

214. Ac-11186

215. As-12460

216. Cas_479-18-5

217. Sy011592

218. Sbi-0051359.p003

219. Db-051485

220. Ab00051977

221. D3600

222. Ft-0632186

223. Sw196679-3

224. C07819

225. D00691

226. Ab00051977-15

227. Ab00051977_16

228. Ab00051977_17

229. Q-201013

230. Q1073333

231. Sr-01000002972-2

232. Sr-01000002972-3

233. Sr-01000002972-4

234. Brd-a00827783-001-05-5

235. Brd-a00827783-001-15-4

236. Diprophylline, European Pharmacopoeia (ep) Reference Standard

237. Dyphylline, United States Pharmacopeia (usp) Reference Standard

238. 1h-purine-2,6-dione, 7-(2,3-dihydroxypropyl)-3,7-dihydro-1,3-dimethyl-, (+/-)-

2.4 Create Date
2005-03-25
3 Chemical and Physical Properties
Molecular Weight 254.24 g/mol
Molecular Formula C10H14N4O4
XLogP3-1.8
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count5
Rotatable Bond Count3
Exact Mass254.10150494 g/mol
Monoisotopic Mass254.10150494 g/mol
Topological Polar Surface Area98.9 Ų
Heavy Atom Count18
Formal Charge0
Complexity364
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count1
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Information
1 of 2  
Drug NameLufyllin
PubMed HealthDyphylline (By mouth)
Drug ClassesBronchodilator
Drug LabelLUFYLLIN (dyphylline), a xanthine derivative, is a bronchodilator available for oral administration as tablets containing 200 mg and 400 mg of dyphylline. Other ingredients: magnesium stearate, microcrystalline cellulose.Chemically, dyphylline is 7-(...
Active IngredientDyphylline
Dosage FormTablet
RouteOral
Strength200mg; 400mg
Market StatusPrescription
CompanyMeda Pharms

2 of 2  
Drug NameLufyllin
PubMed HealthDyphylline (By mouth)
Drug ClassesBronchodilator
Drug LabelLUFYLLIN (dyphylline), a xanthine derivative, is a bronchodilator available for oral administration as tablets containing 200 mg and 400 mg of dyphylline. Other ingredients: magnesium stearate, microcrystalline cellulose.Chemically, dyphylline is 7-(...
Active IngredientDyphylline
Dosage FormTablet
RouteOral
Strength200mg; 400mg
Market StatusPrescription
CompanyMeda Pharms

4.2 Therapeutic Uses

Bronchodilator Agents; Phosphodiesterase Inhibitors; Vasodilator Agents

National Library of Medicine's Medical Subject Headings online file (MeSH, 1999)


THEOPHYLLINE PREPN...ARE USED TO RELAX BRONCHIAL SMOOTH MUSCLE & TO STIMULATE MYOCARDIUM. ... THEOPHYLLINE COMPD...PLAY IMPORTANT ROLE IN MGMNT OF ASTHMATIC PT. THEY ARE USEFUL AS PROPHYLACTIC DRUGS & ARE VALUABLE ADJUNCTS IN TREATMENT OF PROLONGED ATTACKS & IN MGMNT OF STATUS ASTHMATICUS. /THEOPHYLLINE COMPD/

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 375


PERIPHERAL VASODILATOR & BRONCHODILATOR ACTIONS CHARACTERISTIC OF THEOPHYLLINE DERIV. IT IS EFFECTIVE ORALLY BUT HAS NOT BEEN SHOWN TO BE SUPERIOR TO THEOPHYLLINE SODIUM GLYCINATE. IT ALSO HAS TYPICAL DIURETIC & MYOCARDIAL STIMULANT EFFECTS.

Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 1070


...CAN BE USED INTRAMUSCULARLY WITHOUT PRODUCING LOCAL PAIN BECAUSE IT IS NEUTRAL SOL DERIV.

American Medical Association, AMA Department of Drugs, AMA Drug Evaluations. 3rd ed. Littleton, Massachusetts: PSG Publishing Co., Inc., 1977., p. 638


For more Therapeutic Uses (Complete) data for DYPHYLLINE (11 total), please visit the HSDB record page.


4.3 Drug Warning

IT IS NOT RECOMMENDED FOR USE IN CORONARY DISEASE OR ANGINA PECTORIS UNTIL IT CAN BE SHOWN THAT INCR CORONARY BLOOD FLOW PRECEDES RATHER THAN FOLLOWS MYOCARDIAL STIMULATION.

Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 1070


METHYLXANTHINES CAN ALSO STIMULATE RELEASE OF CATECHOLAMINES FROM ADRENAL MEDULLA & LARGE INCR IN URINARY EXCRETION OF EPINEPHRINE OCCUR... /METHYLXANTHINES/

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 369


4.4 Drug Indication

For relief of acute bronchial asthma and for reversible bronchospasm associated with chronic bronchitis and emphysema.


5 Pharmacology and Biochemistry
5.1 Pharmacology

Dyphylline, a xanthine derivative, is a bronchodilator used for relief of acute bronchial asthma and for reversible bronchospasm associated with chronic bronchitis and emphysema. Dyphylline is a xanthine derivative with pharmacologic actions similar to theophylline and other members of this class of drugs. Its primary action is that of bronchodilation, but it also exhibits peripheral vasodilatory and other smooth muscle relaxant activity to a lesser degree.


5.2 MeSH Pharmacological Classification

Vasodilator Agents

Drugs used to cause dilation of the blood vessels. (See all compounds classified as Vasodilator Agents.)


Bronchodilator Agents

Agents that cause an increase in the expansion of a bronchus or bronchial tubes. (See all compounds classified as Bronchodilator Agents.)


Phosphodiesterase Inhibitors

Compounds which inhibit or antagonize the biosynthesis or actions of phosphodiesterases. (See all compounds classified as Phosphodiesterase Inhibitors.)


5.3 ATC Code

R - Respiratory system

R03 - Drugs for obstructive airway diseases

R03D - Other systemic drugs for obstructive airway diseases

R03DA - Xanthines

R03DA01 - Diprophylline


5.4 Absorption, Distribution and Excretion

Route of Elimination

Dyphylline exerts its bronchodilatory effects directly and, unlike theophylline, is excreted unchanged by the kidneys without being metabolized by the liver. Approximately 88% of a single oral dose can be recovered from the urine unchanged.


...RAPID RATE OF DISPOSITION.

Miller, R. R., and D. J. Greenblatt. Handbook of Drug Therapy. New York: Elsevier North Holland, 1979., p. 939


IT MAY BE MORE CONSISTENTLY ABSORBED FROM GI TRACT & LESS IRRITATING THAN THEOPHYLLINE & AMINOPHYLLINE.

American Medical Association, AMA Department of Drugs, AMA Drug Evaluations. 3rd ed. Littleton, Massachusetts: PSG Publishing Co., Inc., 1977., p. 638


SINGLE DYPHYLLINE DOSE WAS GIVEN TO 5 NORMAL VOLUNTEERS. DOSES OF 19-27 MG/KG RESULTED IN PEAK SERUM CONCN OF 19.3-23.5 MUG/ML & WERE TOLERATED WELL BY 4 SUBJECTS. 1 HAD SEVERE HEADACHE AFTER 28 MG/KG DOSE ASSOC WITH 36.4 MUG/ML; WAS NOT METABOLIZED TO THEOPHYLLINE.

PMID:512873 SIMONS KJ, SIMONS FE R; J PHARM SCI 68 (10): 1327 (1979)


IN 5 NORMAL VOLUNTEERS MEAN T/2 WAS 1.8 HR; MEAN TOTAL BODY CLEARANCE RATE & MEAN RENAL CLEARANCE RATE WERE 333 & 276 ML/MIN, RESPECTIVELY. MEAN VOL OF DISTRIBUTION WAS 0.8 L/KG. IN URINE 83% OF DOSE WAS EXCRETED UNCHANGED & THEOPHYLLINE WAS NOT DETECTED.

PMID:512873 SIMONS KJ, SIMONS FE R; J PHARM SCI 68 (10): 1327 (1979)


For more Absorption, Distribution and Excretion (Complete) data for DYPHYLLINE (6 total), please visit the HSDB record page.


5.5 Metabolism/Metabolites

Hepatic


IN BODY XANTHINES ARE ONLY PARTIALLY DEMETHYLATED & OXIDIZED. THEY ARE LARGELY EXCRETED AS METHYLURIC ACIDS OR AS METHYLXANTHINES. /XANTHINES/

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 374


5.6 Biological Half-Life

2 hours (range 1.8 - 2.1 hours)


5.7 Mechanism of Action

The bronchodilatory action of dyphylline, as with other xanthines, is thought to be mediated through competitive inhibition of phosphodiesterase with a resulting increase in cyclic AMP producing relaxation of bronchial smooth muscle as well as antagonism of adenosine receptors.


THEIR MOST IMPORTANT ACTION...IS THEIR ABILITY TO RELAX SMOOTH MUSCLES OF BRONCHI... THEOPHYLLINE IS MOST EFFECTIVE... /THEOPHYLLINE/

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 370


ACTION OF XANTHINES ON MOTOR ACTIVITY OF GI TRACT... DILUTE SOLN INCR, & HIGH CONCN DEPRESS, TONE & STRENGTH OF CONTRACTION OF ISOLATED INTESTINAL STRIPS. /XANTHINES/

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 370


...ACTION SEEMS TO RESULT FROM INCR IN CONCN OF FACTOR V (AC-GLOBULIN) IN PLASMA WHICH, IN TURN, MAY BE CAUSED BY INCR IN PLASMA CONCN OF FREE FATTY ACIDS PRODUCED...THERE ARE ALSO INCR IN CONCN OF CIRCULATING PROTHROMBIN & FIBRINOGEN. /XANTHINES/

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 371


...ACCOMPANYING DECR IN VENOUS FILLING PRESSURE, WHICH IS CAUSED @ LEAST PARTLY BY MORE COMPLETE EMPTYING OF HEART. /THEOPHYLLINE/

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 369


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