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Chemistry

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Also known as: 83-12-5, 2-phenyl-1,3-indandione, 2-phenyl-1h-indene-1,3(2h)-dione, Rectadione, Dindevan, Phenylindanedione
Molecular Formula
C15H10O2
Molecular Weight
222.24  g/mol
InChI Key
NFBAXHOPROOJAW-UHFFFAOYSA-N
FDA UNII
5M7Y6274ZE

Phenindione
An indandione that has been used as an anticoagulant. Phenindione has actions similar to WARFARIN, but it is now rarely employed because of its higher incidence of severe adverse effects. (From Martindale, The Extra Pharmacopoeia, 30th ed, p234)
1 2D Structure

Phenindione

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
2-phenylindene-1,3-dione
2.1.2 InChI
InChI=1S/C15H10O2/c16-14-11-8-4-5-9-12(11)15(17)13(14)10-6-2-1-3-7-10/h1-9,13H
2.1.3 InChI Key
NFBAXHOPROOJAW-UHFFFAOYSA-N
2.1.4 Canonical SMILES
C1=CC=C(C=C1)C2C(=O)C3=CC=CC=C3C2=O
2.2 Other Identifiers
2.2.1 UNII
5M7Y6274ZE
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 2 Phenyl 1,3 Indandione

2. 2-phenyl-1,3-indandione

3. Dindevan

4. Fenilin

5. Phenylindanedione

6. Phenyline

7. Pindione

2.3.2 Depositor-Supplied Synonyms

1. 83-12-5

2. 2-phenyl-1,3-indandione

3. 2-phenyl-1h-indene-1,3(2h)-dione

4. Rectadione

5. Dindevan

6. Phenylindanedione

7. Phenylindione

8. Danilone

9. Hedulin

10. Athrombon

11. Diophindane

12. Emandione

13. Fenhydren

14. Phenhydren

15. Phenillin

16. Phenyline

17. Theradione

18. Danedion

19. Fenilin

20. Pindione

21. Diadilan

22. Emandion

23. Eridione

24. Fenindion

25. Hemolidione

26. Phenylen

27. Phenylin

28. Tromazal

29. Bindan

30. Dineval

31. Indema

32. Trombol

33. Indon

34. Cronodione

35. Thrombasal

36. Indion

37. 2-phenylindandione

38. 2-phenyl-1,3-diketohydrindene

39. 1h-indene-1,3(2h)-dione, 2-phenyl-

40. 2-phenylindene-1,3-dione

41. Phenindionum

42. Fenindiona

43. Phenyllin

44. 2-phenyl-1,3-indanedione

45. 1,3-indandione, 2-phenyl-

46. 2-phenyl-2,3-dihydro-1h-indene-1,3-dione

47. Pid

48. 2-phenyl-1,3(2h)-indenedione

49. 2-phenylindan-1,3-dione

50. 2-phenylindane-1,3-dione

51. Phenindione-d5

52. Phenindione (inn)

53. Nsc-41693

54. Chembl711

55. Mls000069422

56. Chebi:8066

57. 5m7y6274ze

58. Cas-83-12-5

59. Ncgc00016329-01

60. Smr000059058

61. Phenindione [inn]

62. Dsstox_cid_3453

63. Dsstox_rid_77033

64. Dsstox_gsid_23453

65. Fenindiona [inn-spanish]

66. Phenindionum [inn-latin]

67. Phenylindandione

68. 2-fenyloindandion-1,3

69. 2-fenyloindandion-1,3 [polish]

70. Hedulin (tn)

71. 70711-53-4

72. Hsdb 3155

73. Sr-01000721861

74. Einecs 201-454-4

75. Nsc 41693

76. Phenindione [usp:inn:ban]

77. Unii-5m7y6274ze

78. Prestwick_872

79. Phenindione(rectadione)

80. Spectrum_000927

81. Phenindione (rectadione)

82. Phenindione [mi]

83. Opera_id_1966

84. Prestwick0_000538

85. Prestwick1_000538

86. Prestwick2_000538

87. Prestwick3_000538

88. Spectrum2_000999

89. Spectrum3_000710

90. Spectrum4_000476

91. Spectrum5_001070

92. P1029

93. Rectadione;phenylindandione

94. Phenindione [hsdb]

95. 2-phenyl-indan-1,3-dione

96. Phenindione [mart.]

97. 1h-indene-1, 2-phenyl-

98. Oprea1_684242

99. Schembl33831

100. Bspbio_000555

101. Bspbio_002499

102. Kbiogr_000952

103. Kbioss_001407

104. Phenindione [who-dd]

105. Mls001148439

106. Divk1c_000307

107. Spectrum1500477

108. Spbio_001097

109. Spbio_002476

110. Bpbio1_000611

111. Gtpl6838

112. Dtxsid5023453

113. Hms500p09

114. Kbio1_000307

115. Kbio2_001407

116. Kbio2_003975

117. Kbio2_006543

118. Kbio3_001719

119. Phenindione [orange Book]

120. Ninds_000307

121. Wln: L56 Bv Dv Chj Cr

122. Hms1569l17

123. Hms1920f20

124. Hms2091n22

125. Hms2096l17

126. Hms2234n06

127. Hms3651m04

128. Hms3713l17

129. Pharmakon1600-01500477

130. 2-phenyl-1,3-indandione, 97%

131. Hy-b0325

132. Nsc41693

133. 1,3(2h)-indenedione, 2-phenyl-

134. Tox21_110375

135. Bdbm50280157

136. Ccg-40217

137. Mfcd00003782

138. Nsc757269

139. S1921

140. Stk395038

141. Akos000445019

142. Tox21_110375_1

143. Zinc100004862

144. Db00498

145. Nsc-757269

146. Idi1_000307

147. Ncgc00016329-02

148. Ncgc00016329-03

149. Ncgc00016329-04

150. Ncgc00016329-05

151. Ncgc00016329-07

152. Ncgc00094756-01

153. Ncgc00094756-02

154. Ncgc00094756-03

155. Ncgc00094756-04

156. Bs-18169

157. Sbi-0051480.p003

158. Ab00052069

159. Sw196997-3

160. C07584

161. D08354

162. D92057

163. Ab00052069_13

164. Ab00052069_14

165. Q1640947

166. Sr-01000721861-2

167. Sr-01000721861-3

168. Brd-k70592963-001-21-7

169. Brd-k70592963-001-26-6

170. Phenindione, United States Pharmacopeia (usp) Reference Standard

171. Uas

2.4 Create Date
2004-09-16
3 Chemical and Physical Properties
Molecular Weight 222.24 g/mol
Molecular Formula C15H10O2
XLogP32.9
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count2
Rotatable Bond Count1
Exact Mass222.068079557 g/mol
Monoisotopic Mass222.068079557 g/mol
Topological Polar Surface Area34.1 Ų
Heavy Atom Count17
Formal Charge0
Complexity304
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 Therapeutic Uses

Anticoagulants

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


...ORAL ANTICOAGULANTS ARE USEFUL IN PREVENTION & TREATMENT OF VARIETY OF THROMBOEMBOLIC DISORDERS. /ORAL ANTICOAGULANTS/

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 1362


...INDICATIONS FOR ANTICOAGULANTS...1) MYOCARDIAL INFARCTION, 2) RHEUMATIC HEART DISEASE, 3) CEREBROVASCULAR DISEASE, 4) VENOUS THROMBOSIS & PULMONARY EMBOLISM, & 5) DISSEMINATED INTRAVASCULAR COAGULATION. /ANTICOAGULANTS/

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 1363


4.2 Drug Warning

IT IS INADVISABLE TO CARRY OUT LONG-TERM THERAPY IN CHRONIC ALCOHOLIC, IN INDIVIDUAL WHO MAY REQUIRE INTENSIVE SALICYLATE THERAPY, OR IN CASES OF MALIGNANT HYPERTENSION & ACTIVE TUBERCULOSIS. ORAL ANTICOAGULANT THERAPY DURING PREGNANCY CARRIES SIGNIFICANT HEMORRHAGIC RISK FOR FETUS. /ORAL ANTICOAGULANTS/

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 1360


...CONTRAINDICATED IN HEMORRHAGIC TENDENCIES, BLOOD DYSCRASIAS, ULCERATIVE LESIONS OF GI TRACT, DIVERTICULITIS, COLITIS, SUBACUTE BACTERIAL ENDOCARDITIS, THREATENED ABORTION, RECENT OPERATIONS ON BRAIN OR SPINAL CORD. REGIONAL & LUMBAR-BLOCK ANESTHESIA, VITAMIN K DEFICIENCY...HEPATIC OR RENAL DISEASE. /ORAL ANTICOAGULANTS/

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 1360


CHANGES IN AVAIL OF VITAMIN K ALTER THERAPEUTIC RESPONSE TO ORAL ANTICOAGULANTS. ... NEWBORN ARE PARTICULARLY SENSITIVE TO ORAL ANTICOAGULANTS. ... RENAL INSUFFICIENCY, FEVER, & SCURVY ENHANCE OR PROLONG ORAL ANTICOAGULANT RESPONSE. /ORAL ANTICOAGULANTS/

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 1357


IT CANNOT BE EMPHASIZED TOO STRONGLY THAT TREATMENT OF EACH PT IS HIGHLY INDIVIDUALIZED MATTER. PT ON ANTICOAGULANT THERAPY MUST BE FOLLOWED BY MEANS OF PROTHROMBIN TIME TESTS & OBSERVED CAREFULLY FOR ANY DEVELOPMENT OF BLEEDING TENDENCY. /ANTICOAGULANTS/

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 1359


For more Drug Warnings (Complete) data for PHENINDIONE (15 total), please visit the HSDB record page.


4.3 Drug Indication

For the treatment of pulmonary embolism, cardiomyopathy, atrial fibrillation and flutter, cerebral embolism, mural thrombosis, and thrombophili. Also used for anticoagulant prophylaxis.


5 Pharmacology and Biochemistry
5.1 Pharmacology

Phenindione thins the blood by antagonizing vitamin K which is required for the production of clotting factors in the liver. Anticoagulants such as Phenindione have no direct effect on an established thrombus, nor do they reverse ischemic tissue damage (damage caused by an inadequate blood supply to an organ or part of the body). However, once a thrombus has occurred, the goal of anticoagulant treatment is to prevent further extension of the formed clot and prevent secondary thromboembolic complications which may result in serious and possibly fatal sequelae. Phenindione has actions similar to warfarin, but it is now rarely employed because of its higer incidence of severe adverse effects.


5.2 MeSH Pharmacological Classification

Anticoagulants

Agents that prevent BLOOD CLOTTING. (See all compounds classified as Anticoagulants.)


5.3 ATC Code

B - Blood and blood forming organs

B01 - Antithrombotic agents

B01A - Antithrombotic agents

B01AA - Vitamin k antagonists

B01AA02 - Phenindione


5.4 Absorption, Distribution and Excretion

Absorption

Absorbed slowly from the gastrointestinal tract.


DURATION OF RESPONSE IS DIRECTLY PROPORTIONAL TO T/2 OF DRUG IN PLASMA. LARGER INITIAL DOSE (LOADING DOSE) OF DRUG, SOONER DESIRED THERAPEUTIC RESPONSE IS ATTAINED... /ORAL ANTICOAGULANTS/

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 1359


BOTH ITS ONSET & DURATION OF ACTION ARE SHORTER THAN THOSE OF DICUMAROL & WARFARIN. THERAPEUTICALLY EFFECTIVE PROTHROMBIN TIME IS ATTAINED IN 24 TO 48 HR. AFTER DISCONTINUATION OF MAINTENANCE THERAPY, PROTHROMBIN TIME RETURNS TO NORMAL IN 1 TO 4 DAYS.

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 1362


WELL ABSORBED FROM GI TRACT...PEAK PROLONGATION OF PROTHROMBIN TIME 18-48 HR, DURATION 1-4 DAYS...CIRCULATING /DRUG/ ALMOST COMPLETELY BOUND TO PLASMA PROTEINS. UPTAKE...BY ERYTHROCYTES IS VARIABLE...DISTRIBUTED TO LIVER, LUNGS, SPLEEN...KIDNEYS /HUMAN, ORAL/

American Society of Hospital Pharmacists. Data supplied on contract from American Hospital Formulary Service and other current ASHP sources., p. 1973


5.5 Metabolism/Metabolites

Hepatic.


5.6 Biological Half-Life

5-10 hours


5.7 Mechanism of Action

Phenindione inhibits vitamin K reductase, resulting in depletion of the reduced form of vitamin K (vitamin KH2). As vitamin K is a cofactor for the carboxylation of glutamate residues on the N-terminal regions of vitamin K-dependent proteins, this limits the gamma-carboxylation and subsequent activation of the vitamin K-dependent coagulant proteins. The synthesis of vitamin K-dependent coagulation factors II, VII, IX, and X and anticoagulant proteins C and S is inhibited. Depression of three of the four vitamin K-dependent coagulation factors (factors II, VII, and X) results in decreased prothrombin levels and a decrease in the amount of thrombin generated and bound to fibrin. This reduces the thrombogenicity of clots.


.../ANTICOAGULANTS/ BLOCK HEPATIC FORMATION OF FACTORS II, VII, IX, & X BY COMPETITIVELY INHIBITING ACTION OF VITAMIN K. ... COUMARIN ANTICOAGULANTS MAY ALSO AFFECT TRANSPORT OF VITAMIN K TO ITS SITE OF ACTION. /ANTICOAGULANTS/

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 1356


ORAL ANTICOAGULANTS HAVE ONLY ONE MAJOR PHARMACOLOGICAL EFFECT--INHIBITION OF BLOOD-CLOTTING MECHANISMS BY INTERFERING WITH HEPATIC SYNTH OF VITAMIN K-DEPENDENT CLOTTING FACTORS. ...EXERT THEIR INITIAL EFFECT IN VIVO ONLY AFTER LATENT PERIOD... /ORAL ANTICOAGULANTS/

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 1355


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