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Coenzyme Q10

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Coenzyme Q10

Synopsis

ACTIVE PHARMA INGREDIENTS

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Chemistry

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Also known as: Ubidecarenone, 303-98-0, Ubiquinone-10, Coq10, Ubiquinone 50, Neuquinon

Molecular Formula

C₅₉H₉₀O₄

Molecular Weight

863.3 g/mol

InChI Key

ACTIUHUUMQJHFO-UPTCCGCDSA-N

FDA UNII

EJ27X76M46

Coenzyme Q10 is a naturally occurring benzoquinone important in electron transport in mitochondrial membranes. Coenzyme Q10 functions as an endogenous antioxidant; deficiencies of this enzyme have been observed in patients with many different types of cancer and limited studies have suggested that coenzyme Q10 may induce tumor regression in patients with breast cancer. This agent may have immunostimulatory effects. (NCI04)

1 2D Structure

Coenzyme Q10

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

2-[(2E,6E,10E,14E,18E,22E,26E,30E,34E)-3,7,11,15,19,23,27,31,35,39-decamethyltetraconta-2,6,10,14,18,22,26,30,34,38-decaenyl]-5,6-dimethoxy-3-methylcyclohexa-2,5-diene-1,4-dione

2.1.2 InChI

InChI=1S/C59H90O4/c1-44(2)24-15-25-45(3)26-16-27-46(4)28-17-29-47(5)30-18-31-48(6)32-19-33-49(7)34-20-35-50(8)36-21-37-51(9)38-22-39-52(10)40-23-41-53(11)42-43-55-54(12)56(60)58(62-13)59(63-14)57(55)61/h24,26,28,30,32,34,36,38,40,42H,15-23,25,27,29,31,33,35,37,39,41,43H2,1-14H3/b45-26+,46-28+,47-30+,48-32+,49-34+,50-36+,51-38+,52-40+,53-42+

2.1.3 InChI Key

ACTIUHUUMQJHFO-UPTCCGCDSA-N

2.1.4 Canonical SMILES

CC1=C(C(=O)C(=C(C1=O)OC)OC)CC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)C

2.1.5 Isomeric SMILES

CC1=C(C(=O)C(=C(C1=O)OC)OC)C/C=C(\C)/CC/C=C(\C)/CC/C=C(\C)/CC/C=C(\C)/CC/C=C(\C)/CC/C=C(\C)/CC/C=C(\C)/CC/C=C(\C)/CC/C=C(\C)/CCC=C(C)C

2.2 Other Identifiers

2.2.1 UNII

EJ27X76M46

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 2,3-dimethoxy-5-methyl-6-decaprenylbenzoquinone

2. Bio-quinone Q10

3. Co-enzyme Q10

4. Coenzyme Q10, (z,z,z,z,z,z,e,e,e)-isomer

5. Coenzyme Q10, Ion (1-), (all-e)-isomer

6. Coq 10

7. Coq10

8. Q-ter

9. Ubidecarenone

10. Ubiquinone 10

11. Ubiquinone 50

12. Ubiquinone Q10

13. Ubisemiquinone

14. Ubisemiquinone Radical

2.3.2 Depositor-Supplied Synonyms

1. Ubidecarenone

2. 303-98-0

3. Ubiquinone-10

4. Coq10

5. Ubiquinone 50

6. Neuquinon

7. Ubiquinone Q10

8. Ubiquinone

9. Justquinon

10. Neuquinone

11. Emitolon

12. Heartcin

13. Inokiten

14. Terekol

15. Udekinon

16. Coenzyme Q-10

17. Vitamin Q

18. Coenzyme Q

19. Coenzyme-q10

20. Bio-quinone Q10

21. Unispheres Q 10

22. Co-enzyme Q10

23. Coenzyme Q 10

24. Puresorb Q 40

25. Aqua Q10

26. Adelir

27. Nsc 140865

28. Oristar Ubq

29. Q 199

30. Api-31510

31. Ube-q

32. Coenzyme Q-199

33. Bpm-31510

34. Nsc-140865

35. Bpm31510

36. Q 10aa

37. 2-((2e,6e,10e,14e,18e,22e,26e,30e,34e)-3,7,11,15,19,23,27,31,35,39-decamethyltetraconta-2,6,10,14,18,22,26,30,34,38-decaen-1-yl)-5,6-dimethoxy-3-methylcyclohexa-2,5-diene-1,4-dione

38. Chebi:46245

39. Ej27x76m46

40. Ubidecarenone For System Suitability

41. Api 31510

42. Nsc-140665

43. 2-[(2e,6e,10e,14e,18e,22e,26e,30e,34e)-3,7,11,15,19,23,27,31,35,39-decamethyltetraconta-2,6,10,14,18,22,26,30,34,38-decaenyl]-5,6-dimethoxy-3-methylcyclohexa-2,5-diene-1,4-dione

44. Ncgc00159429-02

45. Luvacor

46. Dsstox_cid_26054

47. Dsstox_rid_81308

48. Dsstox_gsid_46054

49. (all-e)-2-(3,7,11,15,19,23,27,31,35,39-decamethyl-2,6,10,14,18,22,26,30,34,38-tetracontadecaenyl)-5,6-dimethoxy-3-methyl-2,5-cyclohexadiene-1,4-dione

50. 2,5-cyclohexadiene-1,4-dione, 2-((2e,6e,10e,14e,18e,22e,26e,30e,34e)-3,7,11,15,19,23,27,31,35,39-decamethyl-2,6,10,14,18,22,26,30,34,38-tetracontadecaenyl)-5,6-dimethoxy-3-methyl

51. 2,5-cyclohexadiene-1,4-dione, 2-(3,7,11,15,19,23,27,31,35,39-decamethyl-2,6,10,14,18,22,26,30,34,38-tetracontadecaenyl)-5,6-dimethoxy-3-methyl-, (all-e)-

52. 2-((all-e)-3,7,11,15,19,23,27,31,35,39-decamethyl-2,6,10,14,18,22,26,30,34,38-tetracontadecaenyl)-5,6-dimethoxy-3-methyl-p-benzoquinone

53. 2-(3,7,11,15,19,23,27,31,35,39-decamethyl-2,6,10,14,18,22,26,30,34,38-tetracontadecaenyl)-5,6-dimethoxy-3-methyl-p-benzoquinone

54. P-benzoquinone, 2-(3,7,11,15,19,23,27,31,35,39-decamethyl-2,6,10,14,18,22,26,30,34,38-tetracontadecaenyl)-5,6-dimethoxy-3-methyl-

55. Coq 10

56. Bio-quinon

57. Ubidecarenona

58. Ubidecarenonum

59. Ubidecarenonum [latin]

60. Coenzyme Q(sub 10)

61. Ubidecarenona [spanish]

62. Coq(sub 10)

63. Ubiquinone Q(sub 10)

64. Cas-303-98-0

65. Ccris 9016

66. Co-enzyme Q-10

67. Einecs 206-147-9

68. Co Q10

69. Unbiquinone

70. Armolipid

71. Kudesan

72. Mitocor

73. Akvion

74. Unii-ej27x76m46

75. Nsc140865

76. Liquid-q

77. Ubiquinone-q10

78. Ubidecarenone [inn:ban:jan:nf]

79. Ubiquinone(10)

80. Ncgc00095322-03

81. Kanekaq10

82. 2,5-cyclohexadiene-1,4-dione, 2-((2e,6e,10e,14e,18e,22e,26e,30e,34e)-3,7,11,15,19,23,27,31,35,39-decamethyl-2,6,10,14,18,22,26,30,34,38-tetracontadecaenyl)-5,6-dimethoxy-3-methyl-

83. 2-((2e,6e,10e,14e,18e,22e,26e,30e,34e)-3,7,11,15,19,23,27,31,35,39-decamethyltetraconta-2,6,10,14,18,22,26,30,34,38-decaenyl)-5,6-dimethoxy-3-methylcyclohexa-2,5-diene-1,4-dione

84. 2-[(2e,6e,10e,14e,18e,22e,26e,30e,34e)-3,7,11,15,19,23,27,31,35,39-decamethyltetraconta-2,6,10,14,18,22,26,30,34,38-decaen-1-yl]-5,6-dimethoxy-3-methylcyclohexa-2,5-diene-1,4-dione

85. All-trans-ubiquinone

86. Li-q-sorb

87. Q-gel

88. Adelir (tn)

89. Coenzymeq10,(s)

90. Kaneka Q10

91. Mfcd00042919

92. Bp31510

93. Co Enzyme Q-10

94. Ubiquinone [inci]

95. Coq10; Ubiquinone-10

96. Coenzyme Q10(coq10)

97. Aqua Q 10l10

98. Ubidecarenone [dsc]

99. Ubidecarenone [inn]

100. Ubidecarenone [jan]

101. Ubidecarenone (jp17/inn)

102. Q-gel 100

103. Schembl19858

104. Mls000028745

105. Ubidecarenone [mart.]

106. Ubiquinone 50 [mi]

107. Voriconazole Impurity C

108. Coenzyme Q10 [vandf]

109. Ubidecarenone [usp-rs]

110. Ubidecarenone [who-dd]

111. Chembl454801

112. (non-labelled)coenzyme Q10-d5

113. Dtxsid6046054

114. Schembl11901691

115. Ex-a973

116. Coenzyme Q10, Analytical Standard

117. Hy-n0111

118. Tox21_111660

119. Tox21_113394

120. Ubidecarenone [ep Monograph]

121. Lmpr02010001

122. S2398

123. Zinc85427689

124. Coenzyme Q10, >=98% (hplc)

125. Akos015897104

126. Akos015951232

127. Ac-4352

128. Db09270

129. 2-(3,7,11,15,19,23,27,31,35,39-decamethyl-tetraconta-2,6,10,14,18,22,26,30,34,38-decaenyl)-5,6-dimethoxy-3-methyl-[1,4]benzoquinone

130. 2-[(2e,6e,10e,14e,18e,22e,26e,30e,34e)-3,7,11,15,19,23,27,31,35,39-decamethyl-2,6,10,14,18,22,26,30,34,38-tetracontadecaen-1-yl]-5,6-dimethoxy-3-methyl-2,5-cyclohexadiene-1,4-dione

131. As-13341

132. Ls-15517

133. Q 10

134. Q-10

135. Smr000058651

136. C1971

137. Cs-0007796

138. N1796

139. C-7060

140. D01065

141. 303c980

142. A936217

143. Q321285

144. Ubidecarenone For System Suitability [usp-rs]

145. Ubidecarenone, European Pharmacopoeia (ep) Reference Standard

146. Ubidecarenone, United States Pharmacopeia (usp) Reference Standard

147. 2-deca(3-methylbut-2-enylene)-5,6-dimethoxy-3-methyl-p-benzoquinone

148. Coenzyme Q10 Solution, 1 Mg/ml In Ethanol, Certified Reference Material, Ampule Of 1 Ml

149. Ubidecarenone For System Suitability, European Pharmacopoeia (ep) Reference Standard

150. Ubidecarenone For System Suitability, United States Pharmacopeia (usp) Reference Standard

151. (all-e)-2,3-dimethoxy-5-methyl-6-(3,7,11,15,19,23,27,31-octamethyl-2,6,10,14,18,22,26,30-dotriacontaoctaenyl)-2,5-cyclohexadiene-1,4-dione

152. 2,4-dione, 2-(3,7,11,15,19,23,27,31,35,39-decamethyl-2,6,10,14,18,22,26,30,34,38-tetracontadecaenyl)-5,6-dimethoxy-3-methyl-

153. 2,4-dione, 2-(3,7,11,15,19,23,27,31,35,39-decamethyl-2,6,10,14,18,22,26,30,34,38-tetracontadecaenyl)-5,6-dimethoxy-3-methyl-, (all-e)-

154. 2,5-cyclohexadiene-1,4-dione, 2-((2e,6e,10e,14e,18e,22e,26e,30e,34e)-3,7,11,15,19,23,27,31,35,39-decamethyl-2,6,10,14,18,22,26,30,34,38-tetracontadecaen-1-yl)-5,6-dimethoxy-3-methyl-

155. 2,5-cyclohexadiene-1,4-dione, 2-(3,7,11,15,19,23,27,31,35,39-decamethyl-2,6,10,14,18,22,26,30,34,38-tetracontadecaenyl)-5,6-dimethoxy-3-methyl-, (all Trans)-

156. 2-((all-e)-3,7,11,15,19,23,27,31,35,39-decamethyl-2,6,10,14,18,22,26,30,34,38-tetracontadecaenyl)-5,6-dimethoxy-3-methyl-2,5-cyclohexadiene-1,4-dione

157. 2-(3,7,11,15,19,23,27,31,35,39-decamethyl-2,6,10,14,18,22,26,30,34,38-tetracontadecaenyl)-5,6-dimethoxy-3-methyl-p-benzoquinone, (all Trans)-

158. 2-(3,7,11,15,19,23,27,31,35,39-decamethyl-2,6,10,14,18,22,26,30,34,38-tetracontadecenyl)-5,6-dimethoxy-3-methyl-1,4-benzoquinone

159. 2-[(2e,6e,10e,14e,18e,22e,26e,30e,34e)-3,7,11,15,19,23,27,31,35,39-decamethyl-2,6,10,14,18,22,26,30,34,38-tetracontadecaenyl]-5,6-dimethoxy-3-methyl- 2,5-cyclohexadiene-1,4-dione

160. 2-[(2e,6e,10e,14e,18e,22e,26e,30e,34e)-3,7,11,15,19,23,27,31,35,39-decamethyl-2,6,10,14,18,22,26,30,34,38-tetracontadecaenyl]-5,6-dimethoxy-3-methylbenzo-1,4-quinone #

161. P-benzoquinone,7,11,15,19,23,27,31,35,39-decamethyl-2,6,10,14,18,22,26,30,34,38-tetracontadecaenyl)-5,6-dimethoxy-3-methyl-

2.4 Create Date

2005-03-26

3 Chemical and Physical Properties

Molecular Formula	C₅₉H₉₀O₄
Molecular Weight	863.3 g/mol
XLogP3	19.4
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	31
Exact Mass	862.68391135 g/mol
Monoisotopic Mass	862.68391135 g/mol
Topological Polar Surface Area	52.6 Å²
Heavy Atom Count	63
Formal Charge	0
Complexity	1840
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	9
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Indication

The diet supplements containing ubidecarenone are indicated, as stated in the product label, to assist individuals with cardiovascular complaints including congestive heart failure and systolic hypertension. In the product, ubidecarenone is used to increase the cardiac input as well as for the prevention of several other diseases like Parkinson, fibromyalgia, migraine, periodontal disease and diabetes, based on preclinical studies. It is important to highlight that these products are not FDA approved and it is recommended to use under discretion.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Ubidecarenon has roles in many prysiological process including sulfide oxidation, regulation of mitochondrial permeability transition pore and translocation of protons and calcium ions accross biological membranes. Studies have shown its benefitial effect in treating cancer, statin myopathy, congestive heart failure and hypertension.

5.2 MeSH Pharmacological Classification

Vitamins

Organic substances that are required in small amounts for maintenance and growth, but which cannot be manufactured by the human body. (See all compounds classified as Vitamins.)

5.3 ATC Code

C - Cardiovascular system

C01 - Cardiac therapy

C01E - Other cardiac preparations

C01EB - Other cardiac preparations

C01EB09 - Ubidecarenone

5.4 Absorption, Distribution and Excretion

Absorption

Ubidecarenone is absorbed from the small intestine into the lymphatics and then it can enter the blood. The hydrophobicity and large molecular weight limit its absorption making it very poor and variable depending on the food intake and the number of lipids presented in the food. The absorption is lower in the presence of an empty stomach and greater in presence of high lipid food diet. The daily dosage of ubidecarenone presents the reach of maximal serum concentration by reaching a plateau after three weeks. The pharmacokinetic properties may vary between different brands but studies have reported an AUC of 11.51 mcg h/ml and a Cmax of 0.32 mcg/ml at a time of 7.9 h.

Route of Elimination

The main elimination route of ubidecarenone is through the bile. After its oral administration, over 60% of the dose is excreted in the feces in the form of unchanged ubidecarenone and a small fraction of the metabolites. In the urine, ubidecarenone is bound to saposin B protein and represents only 8.3% of the total administered dose.

Volume of Distribution

Ubidecarenone is distributed to the various tissues of the body and it is able to enter the brain. In preclinical studies with intravenous administration of ubidecarenone, it is reported a volume of distribution of 20.4 L/kg which reflects its ability to penetrate extensively into organs and tissues. AS a general rule, tissues with high-energy requirements or metabolic activity tend to presents higher amounts of ubidecarenone, these organs can be heart, kidney, liver and muscle.

Clearance

In preclinical studies with intravenous administration of ubidecarenone, it is reported a total clearance of 1.18 ml h/kg which was indicative of a prolonged elimination.

5.5 Metabolism/Metabolites

Studies indicate that there is no saturation process during the metabolism of ubidecarenone. It is metabolized in all tissues by the phosphorylation in the cells and transportation to the kidneys for further excretion by the urine. After exerting its action, ubidecarenone is reduced and forms hydroquinone which is capable of recycling and regenerates other antioxidants such as tocopherol and ascorbate. The later metabolism of hydroquinone generates the formation of Q acid I and Q acid II in free and conjugated forms.

5.6 Biological Half-Life

The pharmacokinetic properties may vary between different brands but studies have reported a half-life of ubidecarenone of 21.7 h.

5.7 Mechanism of Action

Ubidecarenone is an essential cofactor in the mitochondrial electron transport chain. Its functions are the acceptance of electrons from the complex I and II and this activity is vital for the production of ATP. It acts as a mobile redox agent shuttling electrons and protons in the electron transport chain. Ubidecarenone also presents antioxidant activity in mitochondria and cellular membranes, protecting against peroxidation of lipid membranes as well as inhibiting oxidation of LDL-cholesterol.

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Coenzyme Q10

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As an ISO9001, ISO22000 certificated supplier, Basic Nutrition supply high-quality ingredients for nutraceuticals. We can offer a range of products from small to large quantites: herbal extract, amino acid, vitamin, etc. Featured products: cranberry extract, rhidiola extract, Q10, hyaluronic acid, cysteine (non-animals), glutathoninr, orgaic products like organic spirulina, organic red yeast rice powder, etc.

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Established in 1994, Rochem is a distributor of pharmaceutical, food, nutritional and animal health ingredients to some of the largest companies in the world. It sources high-quality ingredients manufactured in China. Headquartered in the Hauppauge, New York, Rochem has 16 offices spread across the globe to cater to the needs of its customers. Rochem’s operations are fully cGMP compliant and has been audited by the USFDA as well as several multinational organizations. It also trains and audits its partners to ensure all of their technologies and systems are FDA-compliant.

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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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Pharm-Rx has earned an outstanding reputation since its establishment in 1991, serving as a reputable importer and distributor of active ingredients to the pharmaceutical, nutritional supplement, and food industries. The company maintains an exceptionally selective approach to its suppliers, personally visiting manufacturers overseas to ensure the highest standards. The sustained growth of Pharm-Rx can be attributed to its steadfast commitment to three core values: quality ingredients, competitive pricing, and unparalleled customer service.

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