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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 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

14 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

15 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

16 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

17 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

18 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

4.2 Therapeutic Uses

Antibiotics, Tetracycline

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


AGAINST GRAM-POSITIVE BACTERIA IT IS ABOUT TWICE AS POTENT AS TETRACYCLINE, EXCEPT THAT IT IS UP TO 10 TIMES AS POTENT AGAINST STREP VIRIDANS. FURTHERMORE, STRAINS OF STREP FAECALIS THAT ARE RESISTANT TO OTHER TETRACYCLINES MAY BE SENSITIVE TO DOXYCYCLINE.

Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 1140


DOSE OF DOXYCYCLINE FOR ADULTS IS 100 MG EVERY 12 HR DURING FIRST 24 HR, FOLLOWED BY 100 MG ONCE DAY, OR TWICE DAILY WHEN SEVERE INFECTION IS PRESENT. CHILDREN OVER 8 YR SHOULD RECEIVE 4-5 MG/KG/DAY, DIVIDED INTO 2 EQUAL DOSES GIVEN @ 12 HR INTERVAL DURING FIRST DAY, AFTER WHICH SINGLE DOSE OF HALF THIS AMT IS ADMIN.

Gilman, A.G., T.W. Rall, A.S. Nies and P. Taylor (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 8th ed. New York, NY. Pergamon Press, 1990., p. 1120


AFFINITY OF DOXYCYCLINE FOR METALLIC IONS MAY NOT BE AS GREAT AS THAT OF OTHER TETRACYCLINES SINCE IT CAN BE GIVEN WITH FOOD OR MILK WITHOUT SIGNIFICANT INACTIVATION OR IMPAIRMENT OF ABSORPTION.

American Medical Association, AMA Department of Drugs, AMA Drug Evaluations. 3rd ed. Littleton, Massachusetts: PSG Publishing Co., Inc., 1977., p. 746


For more Therapeutic Uses (Complete) data for DOXYCYCLINE (27 total), please visit the HSDB record page.


4.3 Drug Warning

TETRACYCLINES SHOULD NOT BE ADMIN TO PREGNANT OR NURSING WOMEN & CHILDREN UNDER 8 YR UNLESS THERE ARE COMPELLING REASONS TO DO SO.

American Medical Association. AMA Drug Evaluations Annual 1991. Chicago, IL: American Medical Association, 1991., p. 1298


TREATMENT OF PREGNANT PATIENTS ... MAY PRODUCE DISCOLORATION OF TEETH IN THEIR OFFSPRING. ... CHILDREN UP TO 8 YR OLD MAY BE SUSCEPTIBLE ... TETRACYCLINES ARE DEPOSITED IN SKELETON DURING GESTATION. ... 40% DEPRESSION OF BONE GROWTH ... DEMONSTRATED IN PREMATURE INFANTS TREATED WITH THESE AGENTS. /TETRACYCLINES/

Gilman, A.G., T.W. Rall, A.S. Nies and P. Taylor (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 8th ed. New York, NY. Pergamon Press, 1990., p. 1122


TETRACYCLINES POSE SPECIAL DANGER IN PREGNANT WOMEN, WITH RESPECT TO POSSIBLE HEPATIC INJURY, PARTICULARLY IF USED FOR TREATMENT OF PYELONEPHRITIS, RELATIVELY COMMON OCCURRENCE IN SUCH PATIENTS INDEED, FATALITIES HAVE OCCURRED. /TETRACYCLINES/

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 1188


IT SHOULD BE EMPHASIZED THAT CROSS-SENSITIZATION AMONG VARIOUS TETRACYCLINES IS COMMON.

Gilman, A.G., T.W. Rall, A.S. Nies and P. Taylor (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 8th ed. New York, NY. Pergamon Press, 1990., p. 1122


For more Drug Warnings (Complete) data for DOXYCYCLINE (12 total), please visit the HSDB record page.


4.4 Drug Indication

Doxycycline is indicated for the treatment of various infections by gram-positive and gram-negative bacteria, aerobes and anaerobes, as well other types of bacteria. A complete list of organisms is available in the FDA label and in the "indications" section of this drug entry. The following are some of the major infections that may be treated with doxycycline: Rocky mountain spotted fever, typhus fever and the typhus group, Q fever, rickettsialpox, and tick fevers caused by Rickettsiae Respiratory tract infections caused by Mycoplasma pneumoniae Lymphogranuloma venereum caused by Chlamydia trachomatis Psittacosis (ornithosis) caused by Chlamydia psittaci Trachoma caused by Chlamydia trachomatis, although the infectious agent is not always eliminated as judged by immunofluorescence Inclusion conjunctivitis caused by Chlamydia trachomatis Uncomplicated urethral, endocervical or rectal infections in adults caused by Chlamydia trachomatis Nongonococcal urethritis caused by Ureaplasma urealyticum Relapsing fever due to Borrelia recurrentis **A note regarding anti-microbial resistance** It is important to note that doxycycline is not the drug of choice in the treatment of any type of staphylococcal infection. Up to 44 percent of strains of Streptococcus pyogenes and 74 percent of Streptococcus faecalis have been found to be resistant to tetracyclines. Therefore, tetracyclines such as doxycycline should not be used to treat streptococcal infections unless the microorganism has been demonstrated to be susceptible.


FDA Label


Treatment of periodontal disease in dogs.

Periodontal pocket probing depths > =4 mm are evidence of disease that may be responsive to treatment with the Doxirobe Gel. Use of this product as directed should result in attachment level gains, periodontal pocket depth reductions, local antimicrobial effect and improved gingival health. Noticeable improvements in these parameters should be evident within 2-4 weeks following treatment. The response in individual dogs is dependent on the severity of the condition and rigor of adjunctive therapy.


5 Pharmacology and Biochemistry
5.1 Pharmacology

The tetracyclines, including doxycycline, are mainly bacteriostatic and are thought to exert antimicrobial effects by the inhibition of protein synthesis. Bacteriostatic antibiotics suppress the growth of bacteria, or keep them in the stationary phase of growth. The tetracyclines, including doxycycline, have a similar antimicrobial spectrum of activity against a variety of gram-positive and gram-negative microorganisms, treating numerous infectious diseases. Cross-resistance of these microorganisms to tetracyclines is a common occurrence. Doxycycline shows favorable intra-cellular penetration, with bacteriostatic activity on a wide range of bacteria. Doxycycline has antiparasitic effects,,. In addition to the above effects, this drug has demonstrated anti-inflammatory actions, which may help to manage inflammatory conditions such as rosacea.


5.2 MeSH Pharmacological Classification

Anti-Bacterial Agents

Substances that inhibit the growth or reproduction of BACTERIA. (See all compounds classified as Anti-Bacterial Agents.)


Antimalarials

Agents used in the treatment of malaria. They are usually classified on the basis of their action against plasmodia at different stages in their life cycle in the human. (From AMA, Drug Evaluations Annual, 1992, p1585) (See all compounds classified as Antimalarials.)


5.3 FDA Pharmacological Classification
5.3.1 Active Moiety
DOXYCYCLINE ANHYDROUS
5.3.2 FDA UNII
334895S862
5.3.3 Pharmacological Classes
Tetracyclines [CS]; Tetracycline-class Drug [EPC]
5.4 ATC Code

QJ01AA02


J01AA02

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


A - Alimentary tract and metabolism

A01 - Stomatological preparations

A01A - Stomatological preparations

A01AB - Antiinfectives and antiseptics for local oral treatment

A01AB22 - Doxycycline


J - Antiinfectives for systemic use

J01 - Antibacterials for systemic use

J01A - Tetracyclines

J01AA - Tetracyclines

J01AA02 - Doxycycline


5.5 Absorption, Distribution and Excretion

Absorption

Tetracyclines, such as doxycycline, are readily absorbed and are bound to plasma proteins by varying degrees. Doxycycline is almost completely absorbed after oral administration. This drug is highly lipid soluble and has a low affinity for calcium binding. Absorption is not significantly affected by the concomitant ingestion of food or milk. Peak serum levels of approximately 2.6 mcg/ml are reached at 2 hours following a 200 mg tablet oral dose.


Route of Elimination

Mainly the urine and feces as active and unchanged drug. Between 40% and 60% of an administered dose can be accounted for in the urine by 92 hours, and approximately 30% can be accounted for in the feces.


Volume of Distribution

Doxycycline diffuses readily into most body tissues, fluid and/or cavities and the volume of distribution has been measured as 0.7 L/kg.


Clearance

The excretion of doxycycline by the kidney is about 40% over 72 hours in individuals with normal kidney function (creatinine clearance approximately 75 mL/min). This rate may fall as low as 1-5% over 72 hours in individuals with severe renal insufficiency (creatinine clearance below 10 mL/min). Some clinical studies have shown no major difference in serum half-life of doxycycline (range 18-22 hours) in patients with normal and severely impaired renal function. Hemodialysis does not affect serum half-life of doxycycline.


RELATIVE INSENSITIVITY OF DOXYCYCLINE PHARMACOKINETICS TO RENAL INSUFFICIENCY HAS ... BEEN DEMONSTRATED IN HUMANS & APPEARS TO BE ASSOC WITH INCR FECAL EXCRETION OWING TO DIFFUSION OF DRUG INTO LUMEN OF SMALL INTESTINE. ... RENAL CLEARANCE OF ACTIVE ANTIBIOTIC IS ... 20 ... ML/MIN FOR DOXYCYCLINE ... .

The Chemical Society. Foreign Compound Metabolism in Mammals Volume 3. London: The Chemical Society, 1975., p. 174


SERUM LEVELS OF DOXYCYCLINE ARE EQUIV WHETHER DRUG IS DOSED BY IV OR PER OS ROUTE. AFTER MULTIPLE DAILY IV DOSES OF 200 MG, SERUM LEVELS ... FLUCTUATED BETWEEN 5-6 & 1-2 UG/ML, WHICH IS ABOVE MIN INHIBITORY CONCN FOR MOST SUSCEPTIBLE PATHOGENS.

The Chemical Society. Foreign Compound Metabolism in Mammals Volume 3. London: The Chemical Society, 1975., p. 174


URINARY EXCRETION OF ... DOXYCYCLINE IS INCR @ HIGH URINARY PH VALUES. ALKALINE TREATMENT OF SUBJECTS RESULTED IN 24% INCR IN CUMULATIVE URINARY TETRACYCLINE EXCRETION COMPARED WITH ACID TREATMENT (P< 0.05) & 54% INCR FOR DOXYCYCLINE (P LESS THAN 0.05). RENAL CLEARANCE ... INCR DURING ALKALINE TREATMENT ... .

The Chemical Society. Foreign Compound Metabolism in Mammals Volume 3. London: The Chemical Society, 1975., p. 173


... MORE COMPLETELY ABSORBED AFTER ORAL ADMIN THAN OTHER TETRACYCLINES ... IN PLASMA, IT IS ABOUT 90% PROTEIN BOUND, WHICH IS HIGHEST DEGREE FOR ANY OF TETRACYCLINES.

Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 1140


For more Absorption, Distribution and Excretion (Complete) data for DOXYCYCLINE (20 total), please visit the HSDB record page.


5.6 Metabolism/Metabolites

Doxycycline is metabolized in the liver and gastrointestinal tract and concentrated in bile,. Major metabolic pathways of doxycycline have not been identified, however, enzyme inducers have been found to decrease the half-life of doxycycline.


/DOXYCYCLINE/ IS EXCRETED IN FECES (UP TO 90%) AS INACTIVE CONJUGATE OR PERHAPS AS CHELATE.

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 1186


Although it was previously suggested that doxycycline is partially metabolized in the liver, recent studies indicate that the drug is not metabolized but is partially deactivated in the intestine by chelate formation.

McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 93. Bethesda, MD: American Society of Hospital Pharmacists, Inc., 1993 (Plus Supplements, 1993)., p. 319


5.7 Biological Half-Life

16.33 hr ( 4.53 sd).


DOXYCYCLINE: ROUTES OF EXCRETION: HEPATIC, RENAL; NORMAL HALF-LIFE: 20 HR; MAINTENANCE DOSE INTERVALS: 12-24 HR.

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 1109


DOXYCYCLINE IS LONG-ACTING, HAVING SERUM HALF-LIFE OF 15-17 HR AFTER INITIAL DOSE & ABOUT 22 HR AFTER 4TH DAY OF TREATMENT.

American Medical Association, AMA Department of Drugs, AMA Drug Evaluations. 3rd ed. Littleton, Massachusetts: PSG Publishing Co., Inc., 1977., p. 736


The serum half-life of doxycycline is 14-17 hr after a single dose and 22-24 hr after multiple doses in patients with normal renal function. In patients with severe renal impairment, the serum half-life of doxycycline is reported to be 18-26 hr after a single dose, and 20-30 hr after multiple doses. It appears that serum half-life of doxycycline is not altered in patients undergoing hemodialysis. In patients with normal renal function, approximately 20-26% of a single oral or iv dose of doxycycline is excreted in urine and 20-40% is excreted in feces within 48 hr as active drug. In patients with creatinine clearances less than 10 ml/minute, the fraction of doxycycline excreted in urine within 72 hr may decrease to about 1-5%.

McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 93. Bethesda, MD: American Society of Hospital Pharmacists, Inc., 1993 (Plus Supplements, 1993)., p. 319


5.8 Mechanism of Action

In bacterial replication, an interaction that is important for translation initiation of proteins occurs at the 3 end of the 16S rRNA, found on the ribosome on the 30S subunit,,. The 30S subunit is the smaller subunit of the ribosome of prokaryotes, including bacteria. Tetracyclines such as doxycycline are thought to inhibit translation by binding to the 16S rRNA portion of the ribosome, preventing binding of tRNA to the RNA-30S bacterial ribosomal subunit, which is necessary for the delivery of amino acids for protein synthesis. As a result of the above actions, the initiation of protein synthesis by polyribosome formation is blocked. This stops the replication of bacteria and produces a bacteriostatic effect.


TETRACYCLINES INHIBIT BACTERIAL PROTEIN SYNTHESIS. ... ONCE TETRACYCLINES GAIN ACCESS TO THE BACTERIAL CELL, THEY BIND PRINCIPALLY TO 30 S SUBUNITS OF BACTERIAL RIBOSOMES. THEY APPEAR TO PREVENT ACCESS OF AMINOACYL T-RNA TO M-RNA-RIBOSOME COMPLEX. ... ONLY SMALL PORTION OF DRUG IS IRREVERSIBLY BOUND, & INHIBITORY EFFECTS OF THE TETRACYCLINESARE REVERSIBLE WHEN THE DRUG IS REMOVED. /TETRACYCLINES/

Gilman, A.G., T.W. Rall, A.S. Nies and P. Taylor (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 8th ed. New York, NY. Pergamon Press, 1990., p. 1118


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ROAD,","city":"MUMBAI,MAHARASHTRA","supplier":"CHANGZHOU PHARMACEUTICAL FACTORY","supplierCountry":"CHINA","foreign_port":"SHENYANG TAOXIAN INTERNATIONAL APT, 21","customer":"LUPIN LTD","customerCountry":"INDIA","quantity":"1000.00","actualQuantity":"1000","unit":"KGS","unitRateFc":"197.5","totalValueFC":"201244.1","currency":"USD","unitRateINR":"16711.9","date":"02-Aug-2024","totalValueINR":"16711854","totalValueInUsd":"201244.1","indian_port":"M\/s MAHARASHTRA AIRPORT DEVELOPMENTCOMPANYLIMITED","hs_no":"29413010","bill_no":"1001782","productDescription":"API","marketType":"REGULATED MARKET","country":"CHINA","selfForZScoreResived":"Pharma Grade","supplierPort":"SHENYANG TAOXIAN INTERNATIONAL APT, 21","supplierAddress":"NO.518 LAODONG EAST ROAD, CHANGZHOU JIANGSU PROVINCE CHINA CN","customerAddress":"159, C.S.T. ROAD,"},{"dataSource":"API Import","activeIngredients":"","year":"2024","qtr":"Q3","strtotime":1722623400,"product":"DOXYCYCLINE HYCLATE BP","address":"25, 2ND PULIYUR MAIN ROAD,","city":"CHENNAI, TAMILNADU","supplier":"NUGEN PHARMA LLC","supplierCountry":"CHINA","foreign_port":"SHANGHAI","customer":"MEDOPHARM PRIVATE LIMITED","customerCountry":"INDIA","quantity":"1000.00","actualQuantity":"1000","unit":"KGS","unitRateFc":"45.6","totalValueFC":"46414.4","currency":"USD","unitRateINR":"3854.4","date":"03-Aug-2024","totalValueINR":"3854376","totalValueInUsd":"46414.4","indian_port":"Madras Sea","hs_no":"29413010","bill_no":"4863208","productDescription":"API","marketType":"REGULATED MARKET","country":"CHINA","selfForZScoreResived":"Pharma Grade","supplierPort":"SHANGHAI","supplierAddress":"NO122,M-FLOOR,NASSER LOOTAH AIRPORBUILDING, DUDAI INTERNATIONALAIRPORT ROAD,DUBAI,POST BOX #12556 UNITED ARAB EMIRATES","customerAddress":"25, 2ND PULIYUR MAIN ROAD,"},{"dataSource":"API Import","activeIngredients":"","year":"2024","qtr":"Q3","strtotime":1722969000,"product":"DOXYCYCLINE MONOHYDRATE","address":"ZYDUS TOWER, SARKHEJ-GANDHINAGAR","city":"AHMEDABAD\/GUJRAT","supplier":"HOVIONE HOLDINGS ASIA LIMITED","supplierCountry":"MACAU ISLANDS","foreign_port":"HONG KONG","customer":"ZYDUS LIFESCIENCES LIMITED","customerCountry":"INDIA","quantity":"622.49","actualQuantity":"622.492","unit":"KGS","unitRateFc":"366","totalValueFC":"232104.7","currency":"USD","unitRateINR":"30963.6","date":"07-Aug-2024","totalValueINR":"19274593.29","totalValueInUsd":"232104.7","indian_port":"Ahmedabad-ZIPL-SEZ","hs_no":"29413010","bill_no":"4917229","productDescription":"API","marketType":"","country":"MACAU ISLANDS","selfForZScoreResived":"Pharma Grade","supplierPort":"HONG KONG","supplierAddress":"Aubin House,11th Floor 171-172 Gloucester Road,Wanchal SDNF Hong Kong","customerAddress":"ZYDUS TOWER, SARKHEJ-GANDHINAGAR"},{"dataSource":"API Import","activeIngredients":"","year":"2024","qtr":"Q3","strtotime":1723228200,"product":"DOXYCYCLINE MONOHYDRATE CEP GRADE-PH.EUR. (BATCH NO. M202406001) (FOC) (VALUE FOR CUSTOMS PURPOSE)","address":"430, DLF TOWERS,","city":"NEW DELHI","supplier":"SHANDONG ZHIYE IMPORT AND EXPORT CO.,LTD.","supplierCountry":"CHINA","foreign_port":"SHANGHAI","customer":"XL LABORATORIES PRIVATE LIMITED","customerCountry":"INDIA","quantity":"6.00","actualQuantity":"6","unit":"KGS","unitRateFc":"206","totalValueFC":"1373","currency":"EUR","unitRateINR":"19003.5","date":"10-Aug-2024","totalValueINR":"114021","totalValueInUsd":"1373","indian_port":"Delhi Air","hs_no":"29413010","bill_no":"4992261","productDescription":"API","marketType":"REGULATED MARKET","country":"CHINA","selfForZScoreResived":"Pharma Grade","supplierPort":"SHANGHAI","supplierAddress":"NO. 51,LIUQUAN ROAD,ZIBO CITY,SHANDONG 255000., CHINA","customerAddress":"430, DLF TOWERS,"},{"dataSource":"API Import","activeIngredients":"","year":"2024","qtr":"Q3","strtotime":1723833000,"product":"DOXYCYCLINE MONOHYDRATE . (GREEN CARD. 21044 DT.31.07.2020 VLD.31.03.2025)","address":"PLOT NO.D16\/6, TTC INDL.AREA,","city":"NAVI MUMBAI, MAHARASHTRA","supplier":"YANCHENG SUHAI PHARMACEUTICAL CO., LTD","supplierCountry":"CHINA","foreign_port":"BEIJING","customer":"SVIZERA","customerCountry":"INDIA","quantity":"150.00","actualQuantity":"150","unit":"KGS","unitRateFc":"166","totalValueFC":"25441.9","currency":"USD","unitRateINR":"14085.1","date":"17-Aug-2024","totalValueINR":"2112765","totalValueInUsd":"25441.9","indian_port":"Bombay Air","hs_no":"29413010","bill_no":"5098118","productDescription":"API","marketType":"REGULATED MARKET","country":"CHINA","selfForZScoreResived":"Pharma Grade","supplierPort":"BEIJING","supplierAddress":"HUAFENG INDUSTRIAL PARK DAFENG PORTECONOMIC DEVELOPMENT ZONE DAFENGDISTRICT YANCHENG CITY JIANGSU ,PRO CN","customerAddress":"PLOT NO.D16\/6, TTC INDL.AREA,"},{"dataSource":"API Import","activeIngredients":"","year":"2024","qtr":"Q3","strtotime":1724437800,"product":"DOXYCYCLINE MONOHYDRATE USP (USE FOR PHARMACEUTICAL) (24 DRUMS)","address":"251-254,IIND FLOOR, DLF TOWER","city":"NEW DELHI","supplier":"ZHEJIANG CHEMICALS I & E CORP","supplierCountry":"CHINA","foreign_port":"SHANGHAI","customer":"GRACURE PHARMACEUTICALS LIMITED","customerCountry":"INDIA","quantity":"600.00","actualQuantity":"600","unit":"KGS","unitRateFc":"136","totalValueFC":"83375.9","currency":"USD","unitRateINR":"11539.6","date":"24-Aug-2024","totalValueINR":"6923760","totalValueInUsd":"83375.9","indian_port":"Delhi TKD ICD","hs_no":"29413010","bill_no":"5221971","productDescription":"API","marketType":"REGULATED MARKET","country":"CHINA","selfForZScoreResived":"Pharma Grade","supplierPort":"SHANGHAI","supplierAddress":"EXPORT CORPORATION, NO. 37,QINGCHUNROAD HANGZHOU, CHINAHANGZHOU HANGZHOU, CHINA SDNF","customerAddress":"251-254,IIND FLOOR, DLF TOWER"}]
04-Jan-2021
31-Aug-2024
KGS
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