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Chemistry

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Also known as: 10592-13-9, Doxycycline hcl, Doxycycline, hcl, Doxylin, Doxycycline hyclate, Doxycycline (hydrochloride)
Molecular Formula
C22H25ClN2O8
Molecular Weight
480.9  g/mol
InChI Key
PTNZGHXUZDHMIQ-CVHRZJFOSA-N
FDA UNII
4182Z6T2ET

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

Doxycycline Hydrochloride

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;hydrochloride
2.1.2 InChI
InChI=1S/C22H24N2O8.ClH/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);1H/t7-,10+,14+,15-,17-,22-;/m0./s1
2.1.3 InChI Key
PTNZGHXUZDHMIQ-CVHRZJFOSA-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.Cl
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.Cl
2.2 Other Identifiers
2.2.1 UNII
4182Z6T2ET
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

13. Doxycycline Calcium

14. Doxycycline Calcium Salt (1:2)

15. Doxycycline Chinoin

16. Doxycycline Hemiethanolate

17. Doxycycline Hyclate

18. Doxycycline Monohydrate

19. Doxycycline Monohydrochloride, 6 Epimer

20. Doxycycline Monohydrochloride, 6-epimer

21. Doxycycline Monohydrochloride, Dihydrate

22. Doxycycline Phosphate (1:1)

23. Doxycycline-chinoin

24. Hydramycin

25. Oracea

26. Periostat

27. Vibra Tabs

28. Vibra-tabs

29. Vibramycin

30. Vibramycin Novum

31. Vibravenos

2.3.2 Depositor-Supplied Synonyms

1. 10592-13-9

2. Doxycycline Hcl

3. Doxycycline, Hcl

4. Doxylin

5. Doxycycline Hyclate

6. Doxycycline (hydrochloride)

7. Vibramycin

8. Nsc-756751

9. Chebi:652992

10. 4182z6t2et

11. 24390-14-5

12. Doxigalumicina

13. Vibramycin (tn)

14. Dsstox_cid_25405

15. Dsstox_rid_80856

16. Dsstox_gsid_45405

17. (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;hydrochloride

18. 6-desoxy-5-hydroxytetracycline Hydrochloride

19. Biocamycin

20. Idocyklin

21. Liomycin

22. Midoxin

23. Nivocilin

24. Novadox

25. Samecin

26. Tanamicin

27. Tecacin

28. Vibradox

29. Ecodox

30. Doxy-tablinen

31. Alpha-6-deoxy-5-hydroxytetracycline Hydrochloride

32. Vibramycin Hyclate

33. Doxy-ii

34. Nsc633557

35. Vibramycin Hydrochloride

36. Hyclate

37. C22h25cln2o8

38. Unii-4182z6t2et

39. Sr-01000075844

40. Doxycycline Hydrochloride [jan]

41. Deoxyoxytetracycline Hydrochloride

42. Einecs 234-198-7

43. Deoxy-5-hydroxytetracycline Hydrochloride

44. (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 Hydrochloride Hemiethanolate Hemihydrate

45. (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 Hydrochloride

46. (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

47. Ncgc00016693-01

48. Cas-10592-13-9

49. Schembl40834

50. Spectrum1500266

51. Chembl1256723

52. Dtxsid1045405

53. Hy-n0565a

54. Hms1920i20

55. Pharmakon1600-01500266

56. Tox21_110566

57. Tox21_500405

58. Bdbm50248132

59. Ccg-38949

60. Mfcd03427564

61. Nsc756751

62. Akos015924649

63. Tox21_110566_1

64. Ks-5254

65. Lp00405

66. Nsc 756751

67. Nsc-633557

68. Ncgc00161602-06

69. Ncgc00261090-01

70. 100929-47-3

71. 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, (4s,4ar,5s,5ar,6r,12as)-

72. 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, (4s-(4alpha,4aalpha,5alpha,5aalpha,6alpha,12aalpha))-

73. Ac-12044

74. Bd166411

75. Doxycycline Hydrochloride [who-dd]

76. Eu-0100405

77. D 9891

78. D07877

79. J-000264

80. Sr-01000075844-1

81. Sr-01000075844-8

82. Q27105187

83. 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)-, Hydrochloride (1:1)

84. 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.))- Hydrochloride

85. 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

86. 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,(4s,4ar,5s,5ar,6r,12as)-

87. 4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,5,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-2-naphthacenecarboxamide Hydrochloride

2.4 Create Date
2011-12-26
3 Chemical and Physical Properties
Molecular Weight 480.9 g/mol
Molecular Formula C22H25ClN2O8
Hydrogen Bond Donor Count7
Hydrogen Bond Acceptor Count9
Rotatable Bond Count2
Exact Mass480.1299435 g/mol
Monoisotopic Mass480.1299435 g/mol
Topological Polar Surface Area182 Ų
Heavy Atom Count33
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 Count2
4 Pharmacology and Biochemistry
4.1 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.)


4.2 FDA Pharmacological Classification
4.2.1 Pharmacological Classes
Tetracyclines [CS]; Tetracycline-class Drug [EPC]

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