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Acenocoumarol

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Chemistry

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Also known as: Acenocoumarin, 152-72-7, Nicoumalone, Sintrom, Nitrovarfarian, Nitrowarfarin

Molecular Formula

C₁₉H₁₅NO₆

Molecular Weight

353.3 g/mol

InChI Key

VABCILAOYCMVPS-UHFFFAOYSA-N

FDA UNII

I6WP63U32H

A coumarin that is used as an anticoagulant. Its actions and uses are similar to those of WARFARIN. (From Martindale, The Extra Pharmacopoeia, 30th ed, p233)

1 2D Structure

Acenocoumarol

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

4-hydroxy-3-[1-(4-nitrophenyl)-3-oxobutyl]chromen-2-one

2.1.2 InChI

InChI=1S/C19H15NO6/c1-11(21)10-15(12-6-8-13(9-7-12)20(24)25)17-18(22)14-4-2-3-5-16(14)26-19(17)23/h2-9,15,22H,10H2,1H3

2.1.3 InChI Key

VABCILAOYCMVPS-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CC(=O)CC(C1=CC=C(C=C1)[N+](=O)[O-])C2=C(C3=CC=CC=C3OC2=O)O

2.2 Other Identifiers

2.2.1 UNII

I6WP63U32H

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Acenocoumarin

2. Mini Sintrom

3. Mini-sintrom

4. Minisintrom

5. Nicoumalone

6. Sinkumar

7. Sinthrome

8. Sintrom

9. Syncoumar

10. Syncumar

11. Synthrom

2.3.2 Depositor-Supplied Synonyms

1. Acenocoumarin

2. 152-72-7

3. Nicoumalone

4. Sintrom

5. Nitrovarfarian

6. Nitrowarfarin

7. Nicumalon

8. Sinthrome

9. Acenocumarol

10. Sinkumar

11. Syncoumar

12. Syncumar

13. Acenokumarin

14. Sincoumar

15. Sinthrom

16. Ascumar

17. Syntrom

18. Zotil

19. Acenocoumarolum

20. Acenocumarolo

21. Sintroma

22. Mini-sintrom

23. Nitrophenylacetylethyl-4-hydroxycoumarine

24. Acenocoumarolum [inn-latin]

25. Acitrom

26. Trombostop

27. Acenocoumarol [inn]

28. G-23350

29. 3-(alpha-acetonyl-4-nitrobenzyl)-4-hydroxycoumarin

30. G 23350

31. 3-(alpha-acetonyl-p-nitrobenzyl)-4-hydroxycoumarin

32. 4-hydroxy-3-(1-(4-nitrophenyl)-3-oxobutyl)-2h-1-benzopyran-2-one

33. 3-(alpha-p-nitrophenyl-beta-acetylethyl)-4-hydroxycoumarin

34. 4-hydroxy-3-[1-(4-nitrophenyl)-3-oxobutyl]chromen-2-one

35. 3-(alpha-(p-nitrophenol)-beta-acetylethyl)-4-hydroxycoumarin

36. 3-(alpha-(4'-nitrophenyl)-beta-acetylethyl)-4-hydroxycoumarin

37. Acenocoumarol (inn)

38. Neositron

39. 4-hydroxy-3-[1-(4-nitrophenyl)-3-oxobutyl]-2h-chromen-2-one

40. Nsc-760052

41. 2h-1-benzopyran-2-one, 4-hydroxy-3-(1-(4-nitrophenyl)-3-oxobutyl)-

42. Mls000539171

43. I6wp63u32h

44. Acenocumarolum

45. Chebi:53766

46. Minisintrom

47. Smr000162652

48. Acenokumarin [czech]

49. Acenocumarolo [dcit]

50. Dsstox_cid_2541

51. 3-(a-acetonyl-p-nitrobenzyl)-4-hydroxycoumarin

52. Dsstox_rid_76619

53. Dsstox_gsid_22541

54. 2h-1-benzopyran-2-one, 4-hydroxy-3-[1-(4-nitrophenyl)-3-oxobutyl]-

55. Mini-sintrom (tn)

56. Hsdb 3201

57. Einecs 205-807-3

58. G-23,350

59. Unii-i6wp63u32h

60. 4-hydroxy-3-(1-(4-nitrophenyl)-3-oxobutyl)-2h-chromen-2-one

61. Acenocoumarol [inn:ban:nf]

62. (+/-)-acenocoumarin

63. G23350

64. Ncgc00016414-01

65. Cas-152-72-7

66. Prestwick_773

67. Mfcd00137816

68. 1185071-64-0

69. Opera_id_1500

70. Prestwick0_000110

71. Prestwick1_000110

72. Prestwick2_000110

73. Prestwick3_000110

74. Acenocoumarol [mi]

75. Acenocoumarol [hsdb]

76. Schembl33543

77. Bspbio_000100

78. Ab-014/25000129

79. Mls001074461

80. Acenocoumarol [mart.]

81. 3-(alpha-acetonyl-p-nitrobenzyl)-4-hydroxy-coumarin

82. Spbio_002039

83. Acenocoumarol [who-dd]

84. Bpbio1_000110

85. Chembl397420

86. Gtpl9015

87. Schembl1477562

88. Coumarin, 3-(alpha-acetonyl-p-nitrobenzyl)-4-hydroxy-

89. Dtxsid2022541

90. Dtxsid00991186

91. Acenocoumarol, >=98% (hplc)

92. Hms1568e22

93. Hms2095e22

94. Hms2232p20

95. Hms3372j11

96. Hms3713f17

97. Pharmakon1600-01502411

98. Hy-b1014

99. Tox21_110430

100. Nsc760052

101. Akos015962123

102. Tox21_110430_1

103. Ab03786

104. Ab07575

105. Ab07577

106. Ccg-213077

107. Cs-4527

108. Db01418

109. Nsc 760052

110. Ncgc00179658-01

111. Ncgc00179658-04

112. As-56473

113. Ab00513804

114. Ft-0660959

115. Ft-0660960

116. Ft-0660961

117. D07064

118. T70324

119. Ab00513804_02

120. Ab00527557-09

121. 152a727

122. Q304088

123. Sr-01000678252

124. 2-acetamido-1,2,5-trideoxy-1,5-imino-d-glucitol

125. Sr-01000678252-3

126. W-108047

127. 3-(.alpha.-acetonyl-4-nitrobenzyl)-4-hydroxycoumarin

128. 3-(.alpha.-acetonyl-p-nitrophenyl)-4-hydroxycoumarin

129. Brd-a65051990-001-03-8

130. 3-(.alpha.-acetonyl-p-nitrobenzyl)-4-hydroxy-coumarin

131. Coumarin, 3-(.alpha.-acetonyl-p-nitrobenzyl)-4-hydroxy-

132. 3-(.alpha.-acetonyl-p-nitrobenzyl)-4-hydroxycoumarin

133. 3-(.alpha.-p-nitrophenyl-.beta.-acetylethyl)-4-hydroxycoumarin

134. 2-hydroxy-3-[1-(4-nitrophenyl)-3-oxobutyl]-4h-1-benzopyran-4-one

135. 3-(.alpha.-(4-nitrophenyl)-.beta.-acetylethyl)-4-hydroxycoumarin

136. 3-(.alpha.-(p-nitrophenol)-.beta.-acetylethyl)-4-hydroxycoumarin

137. 4-hydroxy-3-[1-(4-nitrophenyl)-3-oxobutyl]-2h-chromen-2-one #

138. Acenocoumarol, United States Pharmacopeia (usp) Reference Standard

2.4 Create Date

2011-12-26

3 Chemical and Physical Properties

Molecular Formula	C₁₉H₁₅NO₆
Molecular Weight	353.3 g/mol
XLogP3	2.5
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	4
Exact Mass	353.08993720 g/mol
Monoisotopic Mass	353.08993720 g/mol
Topological Polar Surface Area	109 Å²
Heavy Atom Count	26
Formal Charge	0
Complexity	614
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	1
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Therapeutic Uses

Anticoagulants

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

ACTIONS & USES OF ACENOCOUMAROL ARE THOSE OF DICOUMAROL. ... DRUG INTERACTIONS ARE SAME AS THOSE OF DICOUMAROL.

Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 73

ACENOCOUMAROL IS MOST POTENT OF PROTHROMBOPENIC ANTICOAGULANTS.

Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 763

In a randomized double blind study the efficacy and safety of continuous iv heparin plus acenocoumarol ... were compared with the efficacy and safety of acenocoumarol alone in the treatment of proximal vein thrombosis in 120 patients who were randomly assigned to receive heparin by continuous iv infusion for a minimum of 7 days plus acenocoumarol or an identical infusion of placebo acenocoumarol. Each patient was followed for 6 months . The study was terminated early in the group that received acenocoumarol alone because of an excess of symptomatic events (20% as compared with 6.7% in the combined therapy group). Asymptomatic extension of venous thrombosis was observed in 39.6% of the patients in the acenocoumarol group and in 8.2% of patients treated with heparin plus acenocoumarol. Major bleeding complications were infrequent and comparable in the 2 groups. It was concluded that patients with proximal vein thrombosis require initial treatment with full dose heparin, which can safely be combined with acenocoumarol therapy.

PMID:1406880 Brandjes DPN et al; New Eng J Med 327: 1485-9 (1992)

For more Therapeutic Uses (Complete) data for ACENOCOUMAROL (14 total), please visit the HSDB record page.

4.2 Drug Warning

Contraindications to oral anticoagulants include pre-existing or coexisting abnormalities of blood coagulation, active bleeding, recent or imminent surgery of the central nervous system or eye, diagnostic or therapeutic procedures with potential for uncontrollable bleeding including lumbar puncture, malignant hypertension, peptic ulceration, pregnancy, threatened abortion, intrauterine device, cerebrovascular hemorrhage, and bacterial endocarditis. Relative contraindications include thrombocytopenia, pericarditis, pericardial effusions, and unreliability of the patient or of patient supervision. /Oral anticoagulants/

Haddad, L.M., Clinical Management of Poisoning and Drug Overdose. 2nd ed. Philadelphia, PA: W.B. Saunders Co., 1990., p. 308

Most commonly, oral anticoagulant-induced bleeding is minor and consists of bruising, hematuria, epistaxis, conjunctival hemorrhage, minor gastrointestinal bleeding, bleeding from wounds and sites of trauma, and vaginal bleeding. More serious major or fatal bleeding is most commonly gastrointestinal, intracranial, vaginal, retroperitoneal, or related to a wound or site of trauma, although a large variety of other sites of bleeding have been reported. Intracranial bleeding occurs most frequently in patients receiving oral anticoagulants for cerebrovascular disease and most commonly presents as a subdural hematoma, often unassociated with head trauma. Fatal gastrointestinal bleeding is most commonly from a peptic ulcer, although any gastrointestinal lesion may be a potential source of major bleeding. Overall, a bleeding lesion can be identified in about two thirds of cases of oral anticoagulants-related hemorrhage. /Oral anticoagulants/

Haddad, L.M., Clinical Management of Poisoning and Drug Overdose. 2nd ed. Philadelphia, PA: W.B. Saunders Co., 1990., p. 311

Overall, the bleeding rate of oral anticoagulant therapy is influenced by several factors: the intensity of anticoagulation, either intentionally or inadvertent; the underlying clinical disorder for which anticoagulant therapy is used (with bleeding occurring most frequently in ischemic cerebrovascular disease and venous thromboembolism; and, with bleeding occurring most commonly in the elderly; the presence of adverse drug interactions or comorbid factors such as clinical states potentiating warfarin action, pre-existing hemorrhagic diathesis, malignancy, recent surgery, trauma, or pre-existing potential bleeding sites (e.g., surgical wound, peptic ulcer, recent cerebral hemorrhage, carcinoma of colon); the simultaneous use of aspirin (but not of dipyridamole); and patient reliability (e.g., increased bleeding in alcoholics not due to ethanol-warfarin drug interaction but rather to unreliability of drug intake). /Oral anticoagulants/

Haddad, L.M., Clinical Management of Poisoning and Drug Overdose. 2nd ed. Philadelphia, PA: W.B. Saunders Co., 1990., p. 310

OF COUMARIN DERIVATIVES, ACENOCOUMAROL...CONTAINS NITROBENZENE MOIETY & MAY BE POTENTIALLY DANGEROUS FOR LONG-TERM USE.

American Medical Association, AMA Department of Drugs, AMA Drug Evaluations. 3rd ed. Littleton, Massachusetts: PSG Publishing Co., Inc., 1977., p. 115

For more Drug Warnings (Complete) data for ACENOCOUMAROL (28 total), please visit the HSDB record page.

4.3 Drug Indication

For the treatment and prevention of thromboembolic diseases. More specifically, it is indicated for the prevention of cerebral embolism, deep vein thrombosis, pulmonary embolism, thromboembolism in infarction and transient ischemic attacks. It is used for the treatment of deep vein thrombosis and myocardial infarction.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Acenocoumarol inhibits the reduction of vitamin K by vitamin K reductase. This prevents carboxylation of certain glutamic acid residues near the N-terminals of clotting factors II, VII, IX and X, the vitamin K-dependent clotting factors. Glutamic acid carboxylation is important for the interaction between these clotting factors and calcium. Without this interaction, clotting cannot occur. Both the extrinsic (via factors VII, X and II) and intrinsic (via factors IX, X and II) are affected by acenocoumarol.

5.2 MeSH Pharmacological Classification

Anticoagulants

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

5.3 ATC Code

B01AA07

S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355

B - Blood and blood forming organs

B01 - Antithrombotic agents

B01A - Antithrombotic agents

B01AA - Vitamin k antagonists

B01AA07 - Acenocoumarol

5.4 Absorption, Distribution and Excretion

Absorption

Rapidly absorbed orally with greater than 60% bioavailability. Peak plasma levels are attained 1 to 3 hours following oral administration.

Route of Elimination

Mostly via the kidney as metabolites

Volume of Distribution

The volume of distribution at steady-state appeared to be significantly dose dependent: 78 ml/kg for doses < or = 20 microg/kg and 88 ml/kg for doses > 20 microg/kg respectively

ACENOCOUMAROL IS LARGELY EXCRETED BY KIDNEYS, IN UNCHANGED FORM.

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

Rats received sc 1 mg doses of the R- or S-enantiomers of acenocoumarol and biliary and urinary excretion patterns were studied. In 24 hr, 50% biliary and 20% urinary excretion was observed with no gross differences in metabolic pattern or amount of metabolites. Slight differences due to stereochemistry are /noted/.

PMID:2888860 Thussen HH, Baars LG; J Pharm Pharmacol 39: 655-7 (1987)

5.5 Metabolism/Metabolites

Extensively metabolized in the liver via oxidation forming two hydroxy metabolites and keto reduction producing two alcohol metabolites. Reduction of the nitro group produces an amino metabolite which is further transformed to an acetoamido metabolite. Metabolites do not appear to be pharmacologically active.

5.6 Biological Half-Life

8 to 11 hours.

MICROMEDEX Thomson Health Care. USPDI - Drug Information for the Health Care Professional. 22nd ed. Volume 1. MICROMEDEX Thomson Health Care, Greenwood Village, CO. 2002. Content Reviewed and Approved by the U.S. Pharmacopeial Convention, Inc., p. 266

Acenocoumarol has a short half-life of 10 to 24 hours.

Hardman, J.G., L.E. Limbird, P.B., A.G. Gilman. Goodman and Gilman's The Pharmacological Basis of Therapeutics. 10th ed. New York, NY: McGraw-Hill, 2001., p. 1531

5.7 Mechanism of Action

Acenocoumarol 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 clotting factors, 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 resulting in decreased prothrombin levels and a decrease in the amount of thrombin generated and bound to fibrin. This reduces the thrombogenicity of clots.

The oral anticoagulants block the regeneration of reduced vitamin K and thereby induce a state of functional vitamin K deficiency. The mechanism of the inhibition of reductase(s) by the coumarin drugs is not known. There exist reductases that are less sensitive to these drugs but that act only at relatively high concentrations of oxidized vitamin K; this property may explain the observation that administration of sufficient vitamin K can counteract even large doses of oral anticoagulants. /Oral Anticoagulants/

Hardman, J.G., L.E. Limbird, P.B., A.G. Gilman. Goodman and Gilman's The Pharmacological Basis of Therapeutics. 10th ed. New York, NY: McGraw-Hill, 2001., p. 1527

Both 4-hydroxycoumarin derivatives and indandiones (also known as oral anticoagulants) are antagonists of vitamin K. Their use as rodenticides is based on the inhibition of the vitamin K-dependent step in the synthesis of a number of blood coagulation factors. The vitamin K-dependent proteins ...in the coagulation cascade... are the procoagulant factors II (prothrombin), VII (proconvertin), IX (Christmas factor) and X (Stuart-Prower factor), and the coagulation-inhibiting proteins C and S. All these proteins are synthesized in the liver. Before they are released into the circulation the various precursor proteins undergo substantial (intracellular) post-translational modification. Vitamin K functions as a co-enzyme in one of these modifications, namely the carboxylation at well-defined positions of 10-12 glutamate residues into gamma-carboxyglutamate (Gla). The presence of these Gla residues is essential for the procoagulant activity of the various coagulations factors. Vitamin K hydroquinone (KH2) is the active co-enzyme, and its oxidation to vitamin K 2,3-epoxide (KO) provides the energy required for the carboxylation reaction. The epoxide is than recycled in two reduction steps mediated by the enzyme KO reductase... . The latter enzyme is the target enzyme for coumarin anticoagulants. Their blocking of the KO reductase leads to a rapid exhaustion of the supply of KH2, and thus to an effective prevention of the formation of Gla residues. This leads to an accumulation of non-carboxylated coagulation factor precursors in the liver. In some cases these precursors are processed further without being carboxylated, and (depending on the species) may appear in the circulation. At that stage the under-carboxylated proteins are designated as descarboxy coagulation factors. Normal coagulation factors circulate in the form of zymogens, which can only participate in the coagulation cascade after being activated by limited proteolytic degradation. Descarboxy coagulation factors have no procoagulant activity (i.e. they cannot be activated) and neither they can be converted into the active zymogens by vitamin K action. Whereas in anticoagulated humans high levels of circulating descarboxy coagulation factors are detectable, these levels are negligible in warfarin-treated rats and mice. /Anticoagulant rodenticides/

WHO; Environ Health Criteria 175: Anticoagulant Rodenticides p.46 (1995)

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About the Company : Polpharma API. European CDMO partner and API manufacturer since 1951. Poland-based CDMO and API producer, delivering products to pharmaceutical companies worldwide. Aiming at the c...

Polpharma API. European CDMO partner and API manufacturer since 1951. Poland-based CDMO and API producer, delivering products to pharmaceutical companies worldwide. Aiming at the continuous development of Polpharma and caring for the future of patients, business partners and our employees, we are launching a specialized facility for the R&D and Production of HPAPI with an OEL value of 10 ng/m3 (OEB 6). The HP API investment includes separate process laboratories (PDL), analytical laboratories (ADL) with the possibility of performing QC analyses, and a GMP kilo-lab production line with volume up to 1.5 kg with potential volume increase.

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Jai Radhe Sales was founded in 1999 as an out-of-the-box distribution firm specializing in the global supply of high-quality pharmaceutical ingredients. The firm provides complete sourcing solutions for pharmaceutical products from India, including technical and regulatory assistance. It believes in providing its customers with high-quality products at reasonable prices. It has always endeavored to achieve global standards in the field of pharmaceuticals and has carved out a niche for itself through new methods based on current market needs. Today, it has established itself as a truly global company, with exports to almost every continent.

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Century Pharmaceuticals, established in 1982, has 40 years of experience in manufacturing APIs. It has been supplying APIs produced in-house to several major pharma companies in India and abroad. Its APIs are manufactured in accordance with cGMP, 21CFR part 10 and ICH guidelines. It also produces intermediates and develops new APIs as per the needs of its clients. Century conducts biotechnological research that focuses on human therapeutic proteins. Currently, research is underway to find treatments for asthma, mastocytosis and basophilic leukemia. Century supplies research-grade biotech products and a wide range of animal health products.

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API Reference Price

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