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Chemistry

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Also known as: 564-25-0, Vibramycin, Doxytetracycline, Doxycycline (anhydrous), Doxiciclina, Doxycyclinum
Molecular Formula
C22H24N2O8
Molecular Weight
444.4  g/mol
InChI Key
SGKRLCUYIXIAHR-AKNGSSGZSA-N
FDA UNII
334895S862

Doxycycline
A synthetic tetracycline derivative with similar antimicrobial activity.
Doxycycline anhydrous is a Tetracycline-class Drug.
1 2D Structure

Doxycycline

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(4S,4aR,5S,5aR,6R,12aR)-4-(dimethylamino)-1,5,10,11,12a-pentahydroxy-6-methyl-3,12-dioxo-4a,5,5a,6-tetrahydro-4H-tetracene-2-carboxamide
2.1.2 InChI
InChI=1S/C22H24N2O8/c1-7-8-5-4-6-9(25)11(8)16(26)12-10(7)17(27)14-15(24(2)3)18(28)13(21(23)31)20(30)22(14,32)19(12)29/h4-7,10,14-15,17,25-27,30,32H,1-3H3,(H2,23,31)/t7-,10+,14+,15-,17-,22-/m0/s1
2.1.3 InChI Key
SGKRLCUYIXIAHR-AKNGSSGZSA-N
2.1.4 Canonical SMILES
CC1C2C(C3C(C(=O)C(=C(C3(C(=O)C2=C(C4=C1C=CC=C4O)O)O)O)C(=O)N)N(C)C)O
2.1.5 Isomeric SMILES
C[C@@H]1[C@H]2[C@@H]([C@H]3[C@@H](C(=O)C(=C([C@]3(C(=O)C2=C(C4=C1C=CC=C4O)O)O)O)C(=O)N)N(C)C)O
2.2 Other Identifiers
2.2.1 UNII
334895S862
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 2-naphthacenecarboxamide, 4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,5,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-, (4s-(4alpha,4aalpha,5alpha,5aalpha,6alpha,12aalpha))-

2. Alpha 6 Deoxyoxytetracycline

3. Alpha-6-deoxyoxytetracycline

4. Atridox

5. Bmy 28689

6. Bmy-28689

7. Bmy28689

8. Bu 3839t

9. Bu-3839t

10. Bu3839t

11. Doryx

12. Doxycycline Calcium

13. Doxycycline Calcium Salt (1:2)

14. Doxycycline Chinoin

15. Doxycycline Hemiethanolate

16. Doxycycline Hyclate

17. Doxycycline Monohydrate

18. Doxycycline Monohydrochloride, 6 Epimer

19. Doxycycline Monohydrochloride, 6-epimer

20. Doxycycline Monohydrochloride, Dihydrate

21. Doxycycline Phosphate (1:1)

22. Doxycycline-chinoin

23. Hydramycin

24. Oracea

25. Periostat

26. Vibra Tabs

27. Vibra-tabs

28. Vibramycin

29. Vibramycin Novum

30. Vibravenos

2.3.2 Depositor-Supplied Synonyms

1. 564-25-0

2. Vibramycin

3. Doxytetracycline

4. Doxycycline (anhydrous)

5. Doxiciclina

6. Doxycyclinum

7. Monodox

8. Doxycycline Hyclate

9. Doxycycline Anhydrous

10. 6alpha-deoxy-5-oxytetracycline

11. 5-hydroxy-alpha-6-deoxytetracycline

12. Vibramycine

13. Doxychel

14. 6-alpha-deoxy-5-oxytetracycline

15. Doxycyclin

16. Alpha-6-deoxy-5-hydroxytetracycline

17. Bmy-28689

18. Anhydrous Doxycycline

19. Liviatin

20. Doxycycline (inn)

21. Doxy-caps

22. Deoxymykoin

23. Dossiciclina

24. Doxitard

25. Doxivetin

26. Doxycen

27. Investin

28. Chebi:50845

29. Doxy-puren

30. Alpha-doxycycline

31. Doxy-tabs

32. Alpha-6-deoxyoxytetracycline

33. Mmv000011

34. (4s,4ar,5s,5ar,6r,12ar)-4-(dimethylamino)-1,5,10,11,12a-pentahydroxy-6-methyl-3,12-dioxo-4a,5,5a,6-tetrahydro-4h-tetracene-2-carboxamide

35. Doxysol

36. Jenacyclin

37. 6-deoxyoxytetracycline

38. Dossiciclina [dcit]

39. Doxiciclina [italian]

40. Doxycycline [inn]

41. (4s,4ar,5s,5ar,6r,12as)-4-(dimethylamino)-3,5,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide

42. 2-naphthacenecarboxamide,4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,5,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-, (4s,4ar,5s,5ar,6r,12as)-

43. Doxycyclinum [inn-latin]

44. Doxycycline (internal Use)

45. Doxiciclina [inn-spanish]

46. 334895s862

47. Bu-3839t

48. Zenavod

49. Doxcycline Anhydrous

50. Oxytetracycline, 6-deoxy-

51. Doxycycline (tn)

52. Doxychel (tn)

53. Vivox (*hyclate)

54. Dmsc (*fosfatex)

55. Nsc633557

56. Hsdb 3071

57. Monodox (*monohydrate)

58. Bmy28689

59. Bu 3839t

60. 24390-14-5

61. Einecs 209-271-1

62. Bmy 28689

63. Vibramycin (*monohydrate)

64. 4-epioxytetracycline, 6-deoxy-

65. Gs-3065 (*monohydrate)

66. Doxycycline [usan:inn:ban]

67. Sr-01000075844

68. Unii-334895s862

69. 2-naphthacenecarboxamide, 4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,5,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-, (4s-(4alpha,4aalpha,5alpha,5aalpha,6alpha,12aalpha))-

70. Ab08 (*fosfatex)

71. Spectrum_000807

72. (4s,4ar,5s,5ar,6r,12as)-4-(dimethylamino)-3,5,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamidehydrochloride

73. Spectrum2_000143

74. Spectrum3_000408

75. Spectrum4_000527

76. Spectrum5_000947

77. Doxycycline [hsdb]

78. Upcmld-dp021

79. Vibramycin, Doxytetracycline

80. Chembl1433

81. Lopac0_000405

82. Schembl40930

83. Schembl66828

84. Bspbio_001936

85. Doxycycline [who-dd]

86. Kbiogr_001133

87. Kbioss_001287

88. Bidd:gt0146

89. Divk1c_000345

90. Spbio_000246

91. Chembl436921

92. Gtpl6464

93. Schembl1176275

94. Dtxsid0037653

95. Schembl17826665

96. Schembl19270298

97. Schembl21753474

98. Upcmld-dp021:001

99. Bcbcmap01_000024

100. Kbio1_000345

101. Kbio2_001287

102. Kbio2_003855

103. Kbio2_006423

104. Kbio3_001156

105. Dtxsid80992212

106. Ninds_000345

107. Doxycycline Anhydrous [mi]

108. Hms2090e06

109. Doxytetracycline; Doxycycline

110. Hy-n0565

111. Lmpk07000001

112. S5159

113. Zinc16052277

114. Anhydrous Doxycycline [mart.]

115. Akos015900372

116. Zinc100056779

117. Zinc100302137

118. Zinc100611210

119. Zinc109562088

120. Ccg-204498

121. Db00254

122. Sdccgsbi-0050391.p005

123. Idi1_000345

124. Smp1_000107

125. Ncgc00161602-01

126. Ncgc00161602-03

127. Ncgc00161602-04

128. Ncgc00161602-05

129. Ncgc00161602-07

130. Ncgc00161602-14

131. Ncgc00188979-01

132. (4s,4ar,5s,5ar,6r,12as)-4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,5,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-2-naphthacenecarboxamide

133. 2-naphthacenecarboxamide, 4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,5,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-, (4s,4ar,5s,5ar,6r,12as)

134. 2-naphthacenecarboxamide, 4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,5,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-, (4s,4ar,5s,5ar,6r,12as)-

135. 2-naphthacenecarboxamide, 4-alpha-s-(dimethylamino)-1,4,4a-alpha-5,5a-alpha,6,11,12a-octahydro-3,5-alpha,10,12,12a-alpha-pentahydroxy-6-alpha-methyl-1,11-dioxo-

136. As-13499

137. Sbi-0050391.p004

138. Cs-0009105

139. C06973

140. D07876

141. Ab00053465-03

142. Ab00053465_04

143. Ab00053465_05

144. 564d250

145. A817263

146. Doxycycline, Antibiotic For Culture Media Use Only

147. Q422442

148. Sr-01000075844-7

149. Vibramycin;doxytetracycline;doxiciclina;doxycyclinum

150. W-105517

151. Sr-01000075844-18

152. (4s,4ar,5s,5ar,6r,12as)-4-(dimethylamino)-3,5,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-4a,5,5a,6-tetrahydro-4h-tetracene-2-carboxamide

153. 2-naphthacenecarboxamide, 4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,5,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-, (4s-(4.alpha.,4a.alpha.,5.alpha.,5a.alpha.,6.alpha.,12a.alpha.))-

154. 4-(dimethylamino)-1,5,10,11,12a-pentahydroxy-6-methyl-3,12-dioxo-3,4,4a,5,5a,6,12,12a-octahydrotetracene-2-carboximidic Acid

155. 7164-70-7

2.4 Create Date
2011-12-26
3 Chemical and Physical Properties
Molecular Weight 444.4 g/mol
Molecular Formula C22H24N2O8
XLogP3-0.7
Hydrogen Bond Donor Count6
Hydrogen Bond Acceptor Count9
Rotatable Bond Count2
Exact Mass444.15326573 g/mol
Monoisotopic Mass444.15326573 g/mol
Topological Polar Surface Area182 Ų
Heavy Atom Count32
Formal Charge0
Complexity956
Isotope Atom Count0
Defined Atom Stereocenter Count6
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 18  
Drug NameAtridox
PubMed HealthDoxycycline (By mouth)
Drug ClassesAmebicide, Amebicide, Intestinal, Antiacne, Antibiotic, Antimalarial, Antiprotozoal, Dental Agent
Drug LabelDoxycycline is a broad-spectrum antibacterial synthetically derived from oxytetracycline. Monodox 100 mg, 75 mg, and 50 mg capsules contain doxycycline monohydrate equivalent to 100 mg, 75 mg, or 50 mg of doxycycline for oral administration. The chem...
Active IngredientDoxycycline hyclate
Dosage FormSystem, extended release
RoutePeriodontal
Strength50mg
Market StatusPrescription
CompanyTolmar

2 of 18  
Drug NameDoryx
PubMed HealthDoxycycline (By mouth)
Drug ClassesAmebicide, Amebicide, Intestinal, Antiacne, Antibiotic, Antimalarial, Antiprotozoal, Dental Agent
Active IngredientDoxycycline hyclate
Dosage FormTablet, delayed release
RouteOral
Strengtheq 100mg base; eq 80mg base; eq 200mg base; eq 150mg base; eq 75mg base
Market StatusPrescription
CompanyMayne Pharma

3 of 18  
Drug NameDoxy 100
PubMed HealthDoxycycline (Subgingival)
Drug ClassesAntibacterial
Drug LabelDORYX Capsules contain specially coated pellets of doxycycline hyclate, a broad-spectrum antibiotic synthetically derived from oxytetracycline, in a delayed-release formulation for oral administration.The structural formula for doxycycline hyclate is...
Active IngredientDoxycycline hyclate
Dosage FormInjectable
RouteInjection
Strengtheq 100mg base/vial
Market StatusPrescription
CompanyFresenius Kabi Usa

4 of 18  
Drug NameDoxycycline
PubMed HealthDoxycycline
Drug ClassesAmebicide, Amebicide, Intestinal, Antiacne, Antibacterial, Antibiotic, Antimalarial, Antiprotozoal, Dental Agent
Drug LabelDoxycycline for Injection, USP is a sterile, lyophilized powder prepared from a solution of doxycycline hyclate, ascorbic acid and mannitol in Water for Injection. Doxycycline hyclate is a broad spectrum antibiotic derived from oxytetracycline. It is...
Active IngredientDoxycycline; Doxycycline hyclate
Dosage FormInjectable; Tablet; Capsule; For suspension
Routeoral; Injection; Oral
Strengtheq 100mg base; eq 50mg base; eq 150mg base; 40mg; eq 25mg base/5ml; eq 75mg base; eq 100mg base/vial
Market StatusTentative Approval; Prescription
CompanyMylan Pharms; Ranbaxy; Lannett; Eurohlth Intl; Lupin; Agila Speclts; Chartwell Life Sci; Mylan; Par Pharm; Impax Labs; Heritage Pharms

5 of 18  
Drug NameDoxycycline hyclate
PubMed HealthDoxycycline (Injection)
Drug ClassesAntibiotic, Antimalarial, Antiprotozoal
Drug LabelDoxycycline hyclate is a broad-spectrum antibiotic synthetically derived from oxytetracycline. The structural formula is as follows:with a molecular formula of C22H24N2O8H2O and a molecular weight of 462.46. The chemical designation for doxycycline i...
Active IngredientDoxycycline hyclate
Dosage FormTablet; Capsule, delayed release; Capsule; Tablet, delayed release
RouteOral
Strengtheq 100mg base; eq 50mg base; eq 150mg base; eq 20mg base; eq 75mg base
Market StatusPrescription
CompanyCorepharma; Mutual Pharma; Vintage Pharms; Mylan Pharms; Blu Caribe; Ivax Sub Teva Pharms; Actavis Elizabeth; Larken Labs; Lannett; Mutual Pharm; Actavis Labs Fl; Medicis; Chartwell Life Sci; Hikma Pharms; Mylan; Impax Labs; Heritage Pharms

6 of 18  
Drug NameMonodox
Drug LabelVibramycin is an antibacterial drug synthetically derived from oxytetracycline, and is available as Vibramycin Monohydrate (doxycycline monohydrate); Vibramycin Hyclate and Vibra-Tabs (doxycycline hydrochloride hemiethanolate hemihydrate); and Vibram...
Active IngredientDoxycycline
Dosage FormCapsule
RouteOral
Strengtheq 100mg base; eq 50mg base; eq 75mg base
Market StatusPrescription
CompanyAqua Pharms

7 of 18  
Drug NameOracea
PubMed HealthDoxycycline
Drug ClassesAmebicide, Amebicide, Intestinal, Antiacne, Antibacterial, Antibiotic, Antimalarial, Antiprotozoal, Dental Agent
Drug LabelDoxycycline hyclate is a broad-spectrum antibiotic synthetically derived from oxytetracycline. The structural formula is as follows:with a molecular formula of C22H24N2O8H2O and a molecular weight of 462.46. The chemical designation for doxycycline i...
Active IngredientDoxycycline
Dosage FormCapsule
RouteOral
Strength40mg
Market StatusPrescription
CompanyGalderma Labs

8 of 18  
Drug NamePeriostat
PubMed HealthDoxycycline
Drug ClassesAmebicide, Amebicide, Intestinal, Antiacne, Antibacterial, Antibiotic, Antimalarial, Antiprotozoal, Dental Agent
Drug LabelORACEA (doxycycline, USP) Capsules 40 mg are hard gelatin capsule shells filled with two types of doxycycline beads (30 mg immediate release and 10 mg delayed release) that together provide a dose of 40 mg of anhydrous doxycycline (C22H24N2O8).The st...
Active IngredientDoxycycline hyclate
Dosage FormTablet
RouteOral
Strengtheq 20mg base
Market StatusPrescription
CompanyGalderma Labs

9 of 18  
Drug NameVibramycin
Active IngredientDoxycycline calcium; Doxycycline hyclate; Doxycycline
Dosage FormCapsule; Suspension; For suspension
RouteOral
Strengtheq 100mg base; eq 50mg base; eq 50mg base/5ml; eq 25mg base/5ml
Market StatusPrescription
CompanyPfizer

10 of 18  
Drug NameAtridox
PubMed HealthDoxycycline (By mouth)
Drug ClassesAmebicide, Amebicide, Intestinal, Antiacne, Antibiotic, Antimalarial, Antiprotozoal, Dental Agent
Drug LabelDoxycycline is a broad-spectrum antibacterial synthetically derived from oxytetracycline. Monodox 100 mg, 75 mg, and 50 mg capsules contain doxycycline monohydrate equivalent to 100 mg, 75 mg, or 50 mg of doxycycline for oral administration. The chem...
Active IngredientDoxycycline hyclate
Dosage FormSystem, extended release
RoutePeriodontal
Strength50mg
Market StatusPrescription
CompanyTolmar

11 of 18  
Drug NameDoryx
PubMed HealthDoxycycline (By mouth)
Drug ClassesAmebicide, Amebicide, Intestinal, Antiacne, Antibiotic, Antimalarial, Antiprotozoal, Dental Agent
Active IngredientDoxycycline hyclate
Dosage FormTablet, delayed release
RouteOral
Strengtheq 100mg base; eq 80mg base; eq 200mg base; eq 150mg base; eq 75mg base
Market StatusPrescription
CompanyMayne Pharma

12 of 18  
Drug NameDoxy 100
PubMed HealthDoxycycline (Subgingival)
Drug ClassesAntibacterial
Drug LabelDORYX Capsules contain specially coated pellets of doxycycline hyclate, a broad-spectrum antibiotic synthetically derived from oxytetracycline, in a delayed-release formulation for oral administration.The structural formula for doxycycline hyclate is...
Active IngredientDoxycycline hyclate
Dosage FormInjectable
RouteInjection
Strengtheq 100mg base/vial
Market StatusPrescription
CompanyFresenius Kabi Usa

13 of 18  
Drug