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Doxycycline Hyclate
Also known as: Doxycycline hyclate, 24390-14-5, Atridox, Periostat, Vibra-tabs, Doxyprex
Molecular Formula
C46H58Cl2N4O18
Molecular Weight
1025.9  g/mol
InChI Key
UHHHTIKWXBRCLT-VDBOFHIQSA-N
FDA UNII
19XTS3T51U

A synthetic tetracycline derivative with similar antimicrobial activity.
1 2D Structure

Doxycycline Hyclate

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;ethanol;hydrate;dihydrochloride
2.1.2 InChI
InChI=1S/2C22H24N2O8.C2H6O.2ClH.H2O/c2*1-7-8-5-4-6-9(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;1-2-3;;;/h2*4-7,10,14-15,17,25-27,30,32H,1-3H3,(H2,23,31);3H,2H2,1H3;2*1H;1H2/t2*7-,10+,14+,15-,17-,22-;;;;/m00..../s1
2.1.3 InChI Key
UHHHTIKWXBRCLT-VDBOFHIQSA-N
2.1.4 Canonical SMILES
CCO.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.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.O.Cl.Cl
2.1.5 Isomeric SMILES
CCO.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.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.O.Cl.Cl
2.2 Other Identifiers
2.2.1 UNII
19XTS3T51U
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. Doxycycline

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. Doxycycline Hyclate

2. 24390-14-5

3. Atridox

4. Periostat

5. Vibra-tabs

6. Doxyprex

7. Monodoks

8. Tetraclean

9. Doxy-lemmon

10. Doxychel Hyclate

11. Vibramycin

12. Acticlate

13. Mespafin

14. Tetradox

15. Doxy

16. Doxycycline Hydrochloride Hemiethanolate Hemihydrate

17. Retens

18. Doxicrisol

19. Vibraveineuse

20. Vibravenos

21. Azudoxat

22. Clinofug

23. Diocimex

24. Duradoxal

25. Granudoxy

26. Ronaxan

27. Zadorin

28. Spanor

29. Unacil

30. Acticlate Cap

31. 19xts3t51u

32. Nsc-741421

33. 4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,5,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-2-naphthacenecarboxamide Monohydrochloride, Compound With Ethyl Alcohol (2:1), Monohydrate

34. Vivox

35. 6-deoxy-5-hydroxytetracycline Hydrochloride Hemihydrate

36. (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;ethanol;hydrate;dihydrochloride

37. Dentista

38. Doxteric

39. Doxy 100

40. 10592-13-9

41. Mfcd07357237

42. Doxy 200

43. Doxycycline Hyclate (internal Use)

44. Unii-19xts3t51u

45. Doryx Mpc

46. Doxycycline Hyclate [usan:usp]

47. Doxycyclini Hyclas

48. Periostat (tn)

49. (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;ethanol;hydrate;dihydrochloride

50. Vibra-tabs (tn)

51. Lymepak (tn)

52. Doxylar

53. Lymepak

54. Doryx (tn)

55. Wc 2031

56. 2-naphthacenecarboxamide, 4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,5,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-, Hydrochloride, (4s,4ar,5s,5ar,6r,12as)-, Compd. With Ethanol, Hydrate (2:2:1:1)

57. Doxycycline Hyclate (usp)

58. Chembl3989740

59. Doxycycline Hyclate [vandf]

60. (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 Compound With Ethanol (2:1) Dihydrochloride Hydrate

61. Amy32700

62. Doxycycline Hyclate [usp-rs]

63. Doxycycline Hyclate [who-dd]

64. Doxycycline Hyclate [who-ip]

65. S4163

66. Wc2031

67. Akos025402170

68. Ac-6017

69. Ccg-270611

70. Ds-9077

71. Nsc 741421

72. Doxycycline Hyclate [green Book]

73. Doxycycline Hyclate [ep Impurity]

74. Doxycycline Hyclate [orange Book]

75. 2-naphthacenecarboxamide, 4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,5,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-, Monohydrochloride, Compd. With Ethanol (2:1), Monohydrate, (4s-(4alpha,4aalpha,5alpha,5aalpha,6alpha,12aalpha))-

76. 2-naphthacenecarboxamide, 4beta-(dimeethylamino)-1,4,4abeta,5,5abeta,6,11,12a-octahydro-3,5beta,10,12,12abeta-pentahydroxy-6beta-methyl-1,11-dioxo-, Monohydrochloride, Compd. With Ethyl Alcohol (2:1), Monohydrate

77. Bd166236

78. Doxycycline Hyclate [ep Monograph]

79. Doxycycline Hydrochloride Hydrate (jp17)

80. Doxycyclini Hyclas [who-ip Latin]

81. Ethanol, Compd. With (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 Monohydrochloride (1:2), Monohydrate

82. Doxycycline Hyclate [usp Monograph]

83. Doxycycline, Hyclate - Cas 24390-14-5

84. Sw219440-1

85. Sw219440-2

86. D02129

87. Doxycycline Hydrochloride Hydrate [jan]

88. Doxycycline Hyclate 100 Microg/ml In Acetonitrile

89. Q27116248

90. Z2791720087

91. Doxycycline Hydrochloride Hemiethanolate Hemihydrate [mi]

92. Doxycycline Hyclate Is Known As A Broad-spectrum Tetracycline Antibiotic.

93. (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 - Ethanol (2:1) Dihydrochloride Hydrate

94. Bis((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) Ethanol Hydrate Dihydrochloride

2.4 Create Date
2011-12-26
3 Chemical and Physical Properties
Molecular Weight 1025.9 g/mol
Molecular Formula C46H58Cl2N4O18
Hydrogen Bond Donor Count16
Hydrogen Bond Acceptor Count20
Rotatable Bond Count4
Exact Mass1024.3123164 g/mol
Monoisotopic Mass1024.3123164 g/mol
Topological Polar Surface Area385 Ų
Heavy Atom Count70
Formal Charge0
Complexity958
Isotope Atom Count0
Defined Atom Stereocenter Count12
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count6
4 Drug and Medication Information
4.1 Drug Information
1 of 10  
Drug NameAtridox
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 FormSystem, extended release
RoutePeriodontal
Strength50mg
Market StatusPrescription
CompanyTolmar

2 of 10  
Drug NameDoryx
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 10  
Drug NameDoxy 100
PubMed HealthDoxycycline (Injection)
Drug ClassesAntibiotic, Antimalarial, Antiprotozoal
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 hyclate
Dosage FormInjectable
RouteInjection
Strengtheq 100mg base/vial
Market StatusPrescription
CompanyFresenius Kabi Usa

4 of 10  
Drug NameDoxy 200
PubMed HealthDoxycycline (Subgingival)
Drug ClassesAntibacterial
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 FormInjectable
RouteInjection
Strengtheq 200mg base/vial
Market StatusPrescription
CompanyFresenius Kabi Usa

5 of 10  
Drug NameDoxycycline hyclate
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; Hikma Intl Pharms; Mylan Pharms; Blu Caribe; Ivax Sub Teva Pharms; Actavis Elizabeth; Larken Labs; Lannett; Mutual Pharm; Actavis Labs Fl; Medicis; Chartwell Life Sci; Mylan; Impax Labs; Heritage Pharms

6 of 10  
Drug NameDoryx
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

7 of 10  
Drug NameDoxy 100
PubMed HealthDoxycycline (Injection)
Drug ClassesAntibiotic, Antimalarial, Antiprotozoal
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 hyclate
Dosage FormInjectable
RouteInjection
Strengtheq 100mg base/vial
Market StatusPrescription
CompanyFresenius Kabi Usa

8 of 10  
Drug NameDoxy 200
PubMed HealthDoxycycline (Subgingival)
Drug ClassesAntibacterial
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 FormInjectable
RouteInjection
Strengtheq 200mg base/vial
Market StatusPrescription
CompanyFresenius Kabi Usa

9 of 10  
Drug NameDoxycycline hyclate
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; Hikma Intl Pharms; Mylan Pharms; Blu Caribe; Ivax Sub Teva Pharms; Actavis Elizabeth; Larken Labs; Lannett; Mutual Pharm; Actavis Labs Fl; Medicis; Chartwell Life Sci; Mylan; Impax Labs; Heritage Pharms

10 of 10  
Drug NameAtridox
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 FormSystem, extended release
RoutePeriodontal
Strength50mg
Market StatusPrescription
CompanyTolmar

5 Pharmacology and Biochemistry
5.1 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.)


5.2 FDA Pharmacological Classification
5.2.1 Pharmacological Classes
Tetracyclines [CS]; Tetracycline-class Drug [EPC]
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  • TABLET;ORAL - EQ 150MG BASE
  • TABLET;ORAL - EQ 75MG BASE
  • TABLET;ORAL - EQ 100MG BASE
  • CAPSULE;ORAL - EQ 100MG BASE
  • CAPSULE;ORAL - EQ 50MG BASE **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**
  • CAPSULE, DELAYED RELEASE;ORAL - EQ 100MG BASE
  • CAPSULE, DELAYED RELEASE;ORAL - EQ 75MG BASE
  • SYSTEM, EXTENDED RELEASE;PERIODONTAL - 50MG
  • TABLET, DELAYED RELEASE;ORAL - EQ 100MG BASE
  • TABLET, DELAYED RELEASE;ORAL - EQ 120MG BASE
  • TABLET, DELAYED RELEASE;ORAL - EQ 150MG BASE
  • TABLET, DELAYED RELEASE;ORAL - EQ 200MG BASE
  • TABLET, DELAYED RELEASE;ORAL - EQ 50MG BASE
  • TABLET, DELAYED RELEASE;ORAL - EQ 60MG BASE
  • TABLET, DELAYED RELEASE;ORAL - EQ 75MG BASE
  • TABLET, DELAYED RELEASE;ORAL - EQ 80MG BASE
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