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Technical details about Prestwick3_000142, learn more about the structure, uses, toxicity, action, side effects and more

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2D Structure
Also known as: 58-32-2, Persantin, Dipyridamol, Dipyridamine, Persantine, Dipyudamine
Molecular Formula
C24H40N8O4
Molecular Weight
504.6  g/mol
InChI Key
IZEKFCXSFNUWAM-UHFFFAOYSA-N
FDA UNII
64ALC7F90C

A phosphodiesterase inhibitor that blocks uptake and metabolism of adenosine by erythrocytes and vascular endothelial cells. Dipyridamole also potentiates the antiaggregating action of prostacyclin. (From AMA Drug Evaluations Annual, 1994, p752)
Dipyridamole is a Platelet Aggregation Inhibitor. The physiologic effect of dipyridamole is by means of Decreased Platelet Aggregation.
1 2D Structure

2D Structure

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
2-[[2-[bis(2-hydroxyethyl)amino]-4,8-di(piperidin-1-yl)pyrimido[5,4-d]pyrimidin-6-yl]-(2-hydroxyethyl)amino]ethanol
2.1.2 InChI
InChI=1S/C24H40N8O4/c33-15-11-31(12-16-34)23-26-20-19(21(27-23)29-7-3-1-4-8-29)25-24(32(13-17-35)14-18-36)28-22(20)30-9-5-2-6-10-30/h33-36H,1-18H2
2.1.3 InChI Key
IZEKFCXSFNUWAM-UHFFFAOYSA-N
2.1.4 Canonical SMILES
C1CCN(CC1)C2=NC(=NC3=C2N=C(N=C3N4CCCCC4)N(CCO)CCO)N(CCO)CCO
2.2 Other Identifiers
2.2.1 UNII
64ALC7F90C
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Antistenocardin

2. Apo Dipyridamole

3. Apo-dipyridamole

4. Cerebrovase

5. Clridium

6. Curantil

7. Curantyl

8. Dipyramidole

9. Kurantil

10. Miosen

11. Novo Dipiradol

12. Novo-dipiradol

13. Persantin

14. Persantine

2.3.2 Depositor-Supplied Synonyms

1. 58-32-2

2. Persantin

3. Dipyridamol

4. Dipyridamine

5. Persantine

6. Dipyudamine

7. Curantyl

8. Stimolcardio

9. Cardoxin

10. Kurantil

11. Stenocardil

12. Cardioflux

13. Dipiridamol

14. Dipyridan

15. Peridamol

16. Anginal

17. Apricor

18. Coribon

19. Corosan

20. Coroxin

21. Stenocardiol

22. Agilease

23. Chilcolan

24. Justpertin

25. Permiltin

26. Piroan

27. Cleridium 150

28. Coronarine

29. Gulliostin

30. Prandiol

31. Natyl

32. Prandiol 75

33. Usaf Ge-12

34. Dypyridamol

35. Dipyridamolum

36. Dypyridamole

37. 2,2',2'',2'''-((4,8-di(piperidin-1-yl)pyrimido[5,4-d]pyrimidine-2,6-diyl)bis(azanetriyl))tetraethanol

38. Ra 8

39. Ra-8

40. Nsc-515776

41. Dipyridamole (persantine)

42. Nsc 515776

43. Mls000028420

44. 2-[[2-[bis(2-hydroxyethyl)amino]-4,8-di(piperidin-1-yl)pyrimido[5,4-d]pyrimidin-6-yl]-(2-hydroxyethyl)amino]ethanol

45. Cleridium

46. 2-({6-[bis(2-hydroxyethyl)amino]-4,8-bis(piperidin-1-yl)pyrimido[5,4-d][1,3]diazin-2-yl}(2-hydroxyethyl)amino)ethan-1-ol

47. Chembl932

48. 2,6-bis(diethanolamino)-4,8-dipiperidinopyrimido(5,4-d)pyrimidine

49. Iv Persantine

50. Smr000058382

51. 64alc7f90c

52. Chebi:4653

53. Cardoxil

54. B01ac07

55. Pyrimido(5,4-d)pyrimidine, 2,6-bis(bis(2-hydroxyethyl)amino)-4,8-dipiperidino-

56. Nsc515776

57. Ethanol, 2,2',2'',2'''-[(4,8-di-1-piperidinylpyrimido[5,4-d]pyrimidine-2,6-diyl)dinitrilo]tetrakis-

58. Cas-58-32-2

59. Ncgc00015385-12

60. Coridil

61. Protangix

62. 2,6-bis(diethanolamino)-4,8-dipiperidinopyrimido[5,4-d]pyrimidine

63. Dsstox_cid_20668

64. Dsstox_rid_79531

65. Dsstox_gsid_40668

66. 2,2',2'',2'''-((4,8-di(piperidin-1-yl)pyrimido[5,4-d]pyrimidine-2,6-diyl)bis(azanetriyl))tetrakis(ethan-1-ol)

67. 2,2',2'',2'''-{[4,8-di(piperidin-1-yl)pyrimido[5,4-d]pyrimidine-2,6-diyl]dinitrilo}tetraethanol

68. Ethanol, 2,2',2'',2'''-((4,8-di-1-piperidinylpyrimido(5,4-d)pyrimidine-2,6-diyl)dinitrilo)tetrakis-

69. Dipiridamol [inn-spanish]

70. Dipyridamolum [inn-latin]

71. Permole

72. Persantine (tn)

73. (3e)-3-[[(1s,4as,8as)-decahydro-5,5,8a-trimethyl-2-methylene-1-naphthalenyl]methylene]dihydro-5-methoxy-2(3h)3-[(1e)-2-[(1s,4as,8as)-decahydro-5,5,8a-trimethyl-2-methylene-1-naphthalenyl]ethenyl]furan; (+)-coronarin E-furanone; Coronarin D Methyl Ethe

74. 2,2',2'',2'''-((4,8-di(piperidin-1-yl)pyrimido[5,4-d]-pyrimidine-2,6-diyl)bis(azanetriyl))tetraethanol

75. Sr-01000003065

76. Einecs 200-374-7

77. Brn 0068373

78. Unii-64alc7f90c

79. Dipridacot

80. Curanty

81. Prestwick_145

82. Mfcd00010555

83. Dipyridamole [usan:usp:inn:ban:jan]

84. Spectrum_001004

85. Tocris-0691

86. Opera_id_494

87. Prestwick0_000142

88. Prestwick1_000142

89. Prestwick2_000142

90. Prestwick3_000142

91. Spectrum2_000972

92. Spectrum3_000402

93. Spectrum4_000522

94. Spectrum5_000839

95. Dipyridamole [mi]

96. Lopac-d-9766

97. Dipyridamole [inn]

98. Dipyridamole [jan]

99. Upcmld-dp072

100. D 9766

101. Dipyridamole [usan]

102. Cid_3108

103. 2,2',2'',2'''-((4,8-dipiperidinopyrimido(5,4-d)pyrimidine-2,6-diyl)dinitrilo)tetraethanol

104. Dipyridamole [vandf]

105. Lopac0_000464

106. Schembl16119

107. Bspbio_000244

108. Bspbio_001554

109. Bspbio_001924

110. Dipyridamole [mart.]

111. Kbiogr_001123

112. Kbioss_001484

113. 4-26-00-03840 (beilstein Handbook Reference)

114. Mls001076306

115. Mls001333724

116. Mls002548866

117. Dipyridamole [usp-rs]

118. Dipyridamole [who-dd]

119. Divk1c_000696

120. Spectrum1500259

121. Spbio_001003

122. Spbio_002183

123. Bpbio1_000270

124. Gtpl4807

125. Dtxsid6040668

126. Thymidine,6-dihydro-6-methoxy-

127. Upcmld-dp072:001

128. Bdbm23620

129. Dipyridamole (jp17/usp/inn)

130. Hms502c18

131. Izekfcxsfnuwam-uhfffaoysa-

132. Kbio1_000696

133. Kbio2_001484

134. Kbio2_004052

135. Kbio2_006620

136. Kbio3_001144

137. Ninds_000696

138. Bcpp000256

139. Dipyridamole [orange Book]

140. Hms1568m06

141. Hms1791n16

142. Hms1920i10

143. Hms1989n16

144. Hms2089n15

145. Hms2091o18

146. Hms2095m06

147. Hms2232e19

148. Hms3259c03

149. Hms3261m10

150. Hms3266j17

151. Hms3371j03

152. Hms3402n16

153. Hms3411b03

154. Hms3655i20

155. Hms3675b03

156. Hms3712m06

157. Hms3742o03

158. Hms3867f13

159. Pharmakon1600-01500259

160. Zinc643046

161. Dipyridamole [ep Monograph]

162. Amy40468

163. Bcp26947

164. Hy-b0312

165. Dipyridamole [usp Monograph]

166. Tox21_110133

167. Tox21_500464

168. 2,6-bis(diethanolamine)-4,8-dipiperidinopyrimido[5,4-d]pyrimidine

169. Bbl027781

170. Ccg-40190

171. Nsc756743

172. S1895

173. Stl377790

174. Aggrenox Component Dipyridamole

175. Akos000509426

176. Tox21_110133_1

177. Bcp9000613

178. Db00975

179. Dipyridamole, >=98% (tlc), Powder

180. Hs-0041

181. Lp00464

182. Nc00448

183. Nsc-619103

184. Nsc-756743

185. Sdccgsbi-0050449.p005

186. Idi1_000696

187. Smp2_000208

188. Dipyridamole Component Of Aggrenox

189. Ncgc00015385-01

190. Ncgc00015385-02

191. Ncgc00015385-03

192. Ncgc00015385-04

193. Ncgc00015385-05

194. Ncgc00015385-06

195. Ncgc00015385-07

196. Ncgc00015385-08

197. Ncgc00015385-09

198. Ncgc00015385-10

199. Ncgc00015385-11

200. Ncgc00015385-13

201. Ncgc00015385-14

202. Ncgc00015385-15

203. Ncgc00015385-16

204. Ncgc00015385-17

205. Ncgc00015385-18

206. Ncgc00015385-29

207. Ncgc00023914-02

208. Ncgc00023914-04

209. Ncgc00023914-05

210. Ncgc00023914-06

211. Ncgc00023914-07

212. Ncgc00023914-08

213. Ncgc00023914-09

214. Ncgc00023914-10

215. Ncgc00023914-11

216. Ncgc00261149-01

217. 2-({6-[bis(2-hydroxyethyl)amino]-4,8-bis(piperidin-1-yl)-[1,3]diazino[5,4-d]pyrimidin-2-yl}(2-hydroxyethyl)amino)ethan-1-ol

218. 2-[[2-[bis(2-hydroxyethyl)amino]-4,8-bis(1-piperidyl)pyrimido[5,4-d]pyrimidin-6-yl]-(2-hydroxyethyl)amino]ethanol

219. Ac-18100

220. Ac-30804

221. Ethanol, 2,2',2'',2'''-((4,8-dipiperidinopyrimido(5,4-d)pyrimidine-2,6-diyl)dinitrilo)tetra-

222. Ethanol,2,2',2'',2'''-[(4,8-di-1-piperidinylpyrimido[5,4-d]pyrimidine-2,6-diyl)dinitrilo]tetrakis-

223. Nci60_005689

224. Sbi-0050449.p004

225. 2,8-dipiperidinopyrimido[5,4-d]pyrimidine

226. Ab00051974

227. B1933

228. Eu-0100464

229. Ft-0603242

230. Sw196456-3

231. En300-70723

232. Bim-0050449.0001

233. D00302

234. O10551

235. Ab00051974-18

236. Ab00051974-19

237. Ab00051974_20

238. Ab00051974_21

239. A828156

240. A831828

241. Q419374

242. Sr-01000003065-2

243. Sr-01000003065-4

244. Sr-01000003065-5

245. Sr-01000003065-7

246. W-105400

247. Brd-k86301799-001-04-1

248. Brd-k86301799-001-19-9

249. Brd-k86301799-001-24-9

250. Z1259192074

251. Dipyridamole, British Pharmacopoeia (bp) Reference Standard

252. Dipyridamole, European Pharmacopoeia (ep) Reference Standard

253. 2,6-bis(diethanolamino)-4,8-dipiperidinopyrimido-[5,4-d]pyrimidin

254. Dipyridamole, United States Pharmacopeia (usp) Reference Standard

255. Pyrimido(5, 2,6-bis[bis(2-hydroxyethyl)amino]-4,8-diperidino-

256. 2,2'',2'''-[4,8-dipiperidinopyrimido[5,4-d]pyrimidine-2,6-diyl]dinitrilotetraethanol

257. 2,2',2'',2'''-(4,8-dipiperidinopyrimido(5,4-d)pyrimidine-2,6-diyl)dinitrilotetraethanol

258. 2-[[2-(bis(2-hydroxyethyl)amino)-4,8-di(piperidin-1-yl)pyrimido[6,5-e]pyrimidin-

259. Dipyridamole For Peak Identification, European Pharmacopoeia (ep) Reference Standard

260. Ethanol,2',2'',2'''-(4,8-dipiperidinopyrimido[5,4-d]pyrimidine-2,6-diyldinitrilo)tetra-

261. Wln: T66 Bn Dn Gn Inj Ccn Hcn E- At6ntj B2q F2q& J- At6ntj B2q F2q

262. 2,2',2'',2'''-(4,8-di(piperidin-1-yl)pyrimido[5,4-d]pyrimidine-2,6-diyl)bis(azanetriyl)tetraethanol

263. 2,2',2'',2'''-[(4,8-dipiperidin-1-ylpyrimido[5,4-d]pyrimidine-2,6-diyl)dinitrilo]tetraethanol

264. 2,2',2'',2'''-[(4,8-dipiperidinylpyrimido[5,4-d]pyrimidine-2,6-diyl)dinitrilo]tetraethanol

265. 2,2',2'',2'''-[(4,8-dipiperidinylpyrimido[5,4-d]pyrimidine-2,6-diyl)dinitrilo]tetrakisethanol

266. 2-[[2-[bis(2-hydroxyethyl)amino]-4,8-bis(1-piperidinyl)-6-pyrimido[5,4-d]pyrimidinyl]-(2-hydroxyethyl)amino]ethanol

267. Ethanol, 2,2',2'',2'''-(4,8-dipiperidinopyrimido(5,4-d)pyrimidine-2,6-diyldinitrilo)tetra-

268. Ethanol, 2,2',2',2'''-((4,8-di-1-iperidinylpyrimido(5,4-d)pyrimidine-2,6-diyl)dinitrilo)tetrakis-

269. Ethanol,2',2'',2'''-[(4,8-di-1-piperidinylpyrimido[5,4-d]pyrimidine-2,6-diyl)dinitrilo]tetrakis-

270. Ethanol,2',2'',2'''-[(4,8-dipiperidinopyrimido[5,4-d]pyrimidine-2,6-diyl)dinitrilo]tetra-

271. H9f

2.4 Create Date
2005-03-25
3 Chemical and Physical Properties
Molecular Weight 504.6 g/mol
Molecular Formula C24H40N8O4
XLogP30.7
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count12
Rotatable Bond Count12
Exact Mass504.31725179 g/mol
Monoisotopic Mass504.31725179 g/mol
Topological Polar Surface Area145 Ų
Heavy Atom Count36
Formal Charge0
Complexity561
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 Information
1 of 6  
Drug NameAggrenox
PubMed HealthAspirin/Dipyridamole (By mouth)
Drug ClassesPlatelet Aggregation Inhibitor, Phosphodiesterase Inhibitor/Salicylate, Aspirin Combination
Active IngredientAspirin; dipyridamole
Dosage FormCapsule, extended release
RouteOral
Strength200mg; 25mg
Market StatusPrescription
CompanyBoehringer Ingelheim

2 of 6  
Drug NameDipyridamole
PubMed HealthDipyridamole
Drug ClassesDiagnostic Agent, Cardiac Function, Platelet Aggregation Inhibitor
Drug LabelDipyridamole is a coronary vasodilator described as 2,6 bis-(diethanolamino)-4,8 dipiperidino-pyrimido-(5,4-d) pyrimidine. The structural formula is:C24H40N8O4MW 504.63Dipyri...
Active IngredientDipyridamole
Dosage FormInjectable; Tablet
RouteInjection; Oral
Strength75mg; 5mg/ml; 25mg; 50mg
Market StatusPrescription
CompanyBedford; Fresenius Kabi Usa; Hikma Maple; Lannett; Purepac Pharm; Zydus Pharms Usa; Impax Labs; Murty Pharms; Barr

3 of 6  
Drug NamePersantine
PubMed HealthDipyridamole
Drug ClassesDiagnostic Agent, Cardiac Function, Platelet Aggregation Inhibitor
Drug LabelPERSANTINE (dipyridamole USP) is a platelet inhibitor chemically described as 2,2',2",2"'-[(4,8- Dipiperidinopyrimido[5,4-d]pyrimidine-2,6-diyl)dinitrilo]-tetraethanol. It has the following structural formula:Dipyridamole is an odorles
Active IngredientDipyridamole
Dosage FormTablet
RouteOral
Strength25mg; 75mg; 50mg
Market StatusPrescription
CompanyBoehringer Ingelheim

4 of 6  
Drug NameAggrenox
PubMed HealthAspirin/Dipyridamole (By mouth)
Drug ClassesPlatelet Aggregation Inhibitor, Phosphodiesterase Inhibitor/Salicylate, Aspirin Combination
Active IngredientAspirin; dipyridamole
Dosage FormCapsule, extended release
RouteOral
Strength200mg; 25mg
Market StatusPrescription
CompanyBoehringer Ingelheim

5 of 6  
Drug NameDipyridamole
PubMed HealthDipyridamole
Drug ClassesDiagnostic Agent, Cardiac Function, Platelet Aggregation Inhibitor
Drug LabelDipyridamole is a coronary vasodilator described as 2,6 bis-(diethanolamino)-4,8 dipiperidino-pyrimido-(5,4-d) pyrimidine. The structural formula is:C24H40N8O4MW 504.63Dipyri...
Active IngredientDipyridamole
Dosage FormInjectable; Tablet
RouteInjection; Oral
Strength75mg; 5mg/ml; 25mg; 50mg
Market StatusPrescription
CompanyBedford; Fresenius Kabi Usa; Hikma Maple; Lannett; Purepac Pharm; Zydus Pharms Usa; Impax Labs; Murty Pharms; Barr

6 of 6  
Drug NamePersantine
PubMed HealthDipyridamole
Drug ClassesDiagnostic Agent, Cardiac Function, Platelet Aggregation Inhibitor
Drug LabelPERSANTINE (dipyridamole USP) is a platelet inhibitor chemically described as 2,2',2",2"'-[(4,8- Dipiperidinopyrimido[5,4-d]pyrimidine-2,6-diyl)dinitrilo]-tetraethanol. It has the following structural formula:Dipyridamole is an odorles
Active IngredientDipyridamole
Dosage FormTablet
RouteOral
Strength25mg; 75mg; 50mg
Market StatusPrescription
CompanyBoehringer Ingelheim

4.2 Drug Indication

For as an adjunct to coumarin anticoagulants in the prevention of postoperative thromboembolic complications of cardiac valve replacement and also used in prevention of angina.


FDA Label


5 Pharmacology and Biochemistry
5.1 Pharmacology

Dipyridamole, a non-nitrate coronary vasodilator that also inhibits platelet aggregation, is combined with other anticoagulant drugs, such as warfarin, to prevent thrombosis in patients with valvular or vascular disorders. Dipyridamole is also used in myocardial perfusion imaging, as an antiplatelet agent, and in combination with aspirin for stroke prophylaxis.


5.2 MeSH Pharmacological Classification

Vasodilator Agents

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


Phosphodiesterase Inhibitors

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


Platelet Aggregation Inhibitors

Drugs or agents which antagonize or impair any mechanism leading to blood platelet aggregation, whether during the phases of activation and shape change or following the dense-granule release reaction and stimulation of the prostaglandin-thromboxane system. (See all compounds classified as Platelet Aggregation Inhibitors.)


5.3 FDA Pharmacological Classification
5.3.1 Active Moiety
DIPYRIDAMOLE
5.3.2 FDA UNII
64ALC7F90C
5.3.3 Pharmacological Classes
Platelet Aggregation Inhibitor [EPC]; Decreased Platelet Aggregation [PE]
5.4 ATC Code

B - Blood and blood forming organs

B01 - Antithrombotic agents

B01A - Antithrombotic agents

B01AC - Platelet aggregation inhibitors excl. heparin

B01AC07 - Dipyridamole


5.5 Absorption, Distribution and Excretion

Absorption

70%


Route of Elimination

Dipyridamole is metabolized in the liver to the glucuronic acid conjugate and excreted with the bile.


Volume of Distribution

1 to 2.5 L/kg


Clearance

2.3-3.5 mL/min/kg


5.6 Metabolism/Metabolites

hepatic


5.7 Biological Half-Life

40 minutes


5.8 Mechanism of Action

Dipyridamole likely inhibits both adenosine deaminase and phosphodiesterase, preventing the degradation of cAMP, an inhibitor of platelet function. This elevation in cAMP blocks the release of arachidonic acid from membrane phospholipids and reduces thromboxane A2 activity. Dipyridamole also directly stimulates the release of prostacyclin, which induces adenylate cyclase activity, thereby raising the intraplatelet concentration of cAMP and further inhibiting platelet aggregation.


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