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Chemistry

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Also known as: Isphamycin, 64-72-2, Chlortetracycline hcl, Aureociclina, Chlorotetracycline hydrochloride, Aureomycin

Molecular Formula

C₂₂H₂₄Cl₂N₂O₈

Molecular Weight

515.3 g/mol

InChI Key

QYAPHLRPFNSDNH-MRFRVZCGSA-N

FDA UNII

O1GX33ON8R

A TETRACYCLINE with a 7-chloro substitution.

1 2D Structure

Chlortetracycline Hydrochloride

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(4S,4aS,5aS,6S,12aR)-7-chloro-4-(dimethylamino)-1,6,10,11,12a-pentahydroxy-6-methyl-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboxamide;hydrochloride

2.1.2 InChI

InChI=1S/C22H23ClN2O8.ClH/c1-21(32)7-6-8-15(25(2)3)17(28)13(20(24)31)19(30)22(8,33)18(29)11(7)16(27)12-10(26)5-4-9(23)14(12)21;/h4-5,7-8,15,26-27,30,32-33H,6H2,1-3H3,(H2,24,31);1H/t7-,8-,15-,21-,22-;/m0./s1

2.1.3 InChI Key

QYAPHLRPFNSDNH-MRFRVZCGSA-N

2.1.4 Canonical SMILES

CC1(C2CC3C(C(=O)C(=C(C3(C(=O)C2=C(C4=C(C=CC(=C41)Cl)O)O)O)O)C(=O)N)N(C)C)O.Cl

2.1.5 Isomeric SMILES

C[C@@]1([C@H]2C[C@H]3[C@@H](C(=O)C(=C([C@]3(C(=O)C2=C(C4=C(C=CC(=C41)Cl)O)O)O)O)C(=O)N)N(C)C)O.Cl

2.2 Other Identifiers

2.2.1 UNII

O1GX33ON8R

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 4-epimer Chlortetracycline

2. Aureocyclin

3. Aureomycin

4. Aureomycine

5. Biomycin

6. Bisulfate, Chlortetracycline

7. Calcium Salt Chlortetracycline

8. Chlorotetracycline

9. Chlortetracycline

10. Chlortetracycline Bisulfate

11. Chlortetracycline Monohydrochloride

12. Chlortetracycline Sulfate (1:1)

13. Chlortetracycline Sulfate (2:1)

14. Chlortetracycline, 4 Epimer

15. Chlortetracycline, 4-epimer

16. Chlortetracycline, Calcium Salt

17. Hydrochloride, Chlortetracycline

18. Monohydrochloride, Chlortetracycline

19. Salt Chlortetracycline, Calcium

2.3.2 Depositor-Supplied Synonyms

1. Isphamycin

2. 64-72-2

3. Chlortetracycline Hcl

4. Aureociclina

5. Chlorotetracycline Hydrochloride

6. Aureomycin

7. Aureocycline

8. Aureocarmyl

9. Auxeomycin

10. Clorocipan

11. Fermycin Soluble

12. Aureomycin Monohydrochloride

13. Aureomycin Hydrochloride

14. B-aureo

15. Tetra 5

16. Cltc

17. Biomycin Hydrochloride

18. 7-chlorotetracycline Hydrochloride

19. Biomitsin Hydrochloride

20. Psittacin Hydrochloride

21. Nsc-13252

22. Chlortetracyclinium Chloride

23. Alexomycin

24. Chlortetracycline (hydrochloride)

25. Chlortetracycline, Monohydrochloride

26. 7-chlorotetracycline Monohydrochloride

27. Nsc13252

28. U-6780

29. O1gx33on8r

30. 7-chloro-4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-2-naphthacenecarboxamide Monohydrochloride

31. 64-72-2 (hcl)

32. Aureomycin (tn)

33. Dsstox_cid_25076

34. Dsstox_rid_80653

35. Dsstox_gsid_45076

36. (4s,4as,5as,6s,12as)-7-chloro-4-(dimethylamino)-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide Hydrochloride

37. Aurofac 100

38. Aureovit 12c80

39. Pennchlor 64

40. Einecs 200-591-7

41. Clorotetraciclina Cloridrato

42. Clorotetraciclina Cloridrato [italian]

43. Unii-o1gx33on8r

44. Tetracycline, 7-chloro-, Hydrochloride

45. Cltc 100 Mr

46. C22h24cl2n2o8

47. Ai3-50126

48. Sr-05000001588

49. (4s,4as,5as,6s,12as)-7-chloro-4-(dimethylamino)-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboxamide;hydrochloride

50. Alexomycin [usan]

51. Mfcd26142699

52. Chlortetracycline Hydrochloride [usp:ban]

53. Cas-64-72-2

54. Ncgc00016289-01

55. Schembl3841

56. 2-naphthacenecarboxamide, 7-chloro-4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-, Monohydrochloride, (4s,4as,5as,6s,12as)-

57. Mls001304009

58. Mls006011591

59. Spectrum1500186

60. Unii-sl2pe81977

61. Chlorotetracycline Hydrochloride 100 Microg/ml In Acetonitrile/water

62. Chlortetracyclini Hydrochloridum

63. Chembl2146063

64. Dtxsid2045076

65. Hms1568m12

66. Hms1920m07

67. Pharmakon1600-01500186

68. Sl2pe81977

69. 3671-08-7

70. Hy-b1327

71. Tox21_110353

72. Tox21_301710

73. Ccg-39737

74. Nsc756691

75. Akos015960769

76. Cs-4853

77. Ds-3304

78. Nsc-756691

79. Ncgc00256236-01

80. 165101-50-8

81. 2-naphthacenecarboxamide, 7-chloro-4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-, Monohydrochloride (4s-(4alpha,4aalpha,5aalpha,6beta,12aalpha))-

82. Ac-12254

83. Smr000387083

84. Smr004703365

85. Chlortetracycline Hydrochloride (jan/usp)

86. Chlortetracycline Hydrochloride [mi]

87. C3458

88. Chlortetracycline Hydrochloride [jan]

89. Chlortetracycline Hydrochloride [vandf]

90. Chlortetracycline Hydrochloride [mart.]

91. Chlortetracycline Hydrochloride [usp-rs]

92. Chlortetracycline Hydrochloride [who-dd]

93. Chlortetracycline Hydrochloride [who-ip]

94. D02255

95. U 82127

96. U-82127

97. Chlortetracycline Hydrochloride [green Book]

98. Sr-05000001588-2

99. U 82,127

100. U-82,127

101. Chlortetracycline Hydrochloride [ep Monograph]

102. Chlortetracycline Hydrochloride [usp Impurity]

103. Chlortetracycline Hydrochloride [usp Monograph]

104. Chlortetracyclini Hydrochloridum [who-ip Latin]

105. Q27285204

106. Wln: L E6 C666 Bv Fv Cu Guttt&j Dq Eq Gvz Hq In1&1 Mq M1 Og Rq &gh

107. (4s,4as,5as,6s,12ar)-7-chloro-4-(dimethylamino)-1,6,10,11,12a-pentahydroxy-6-methyl-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboxamide;hydrochloride

108. 2-naphthacenecarboxamide, 7-chloro-4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-, Monohydrochloride (4s-(4.alpha.,4a.alpha.,5a.alpha.,6.beta.,12a.alpha.))-

109. 2-naphthacenecarboxamide,4,4a,5,5a,6,11,12a-octahydro-3,6,10,12a-pentahydroxy-6-methyl-1,11-dioxo-, Monohydrochloride

110. 2-naphthacenecarboxamide,7-chloro-4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-, Monohydrochloride,(4s,4as,5as,6s,12as)-

111. 7-chloro-4-dimethylamino-1,4a,5,5a,6,11,12a-octahydro-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-2-naphthacene-carboxamide, Hydrochloride

2.4 Create Date

2011-12-26

3 Chemical and Physical Properties

Molecular Formula	C₂₂H₂₄Cl₂N₂O₈
Molecular Weight	515.3 g/mol
Hydrogen Bond Donor Count	7
Hydrogen Bond Acceptor Count	9
Rotatable Bond Count	2
Exact Mass	514.0909711 g/mol
Monoisotopic Mass	514.0909711 g/mol
Topological Polar Surface Area	182 Å²
Heavy Atom Count	34
Formal Charge	0
Complexity	1010
Isotope Atom Count	0
Defined Atom Stereocenter Count	5
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	2

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.)

Antiprotozoal Agents

Substances that are destructive to protozoans. (See all compounds classified as Antiprotozoal Agents.)

Protein Synthesis Inhibitors

Compounds which inhibit the synthesis of proteins. They are usually ANTI-BACTERIAL AGENTS or toxins. Mechanism of the action of inhibition includes the interruption of peptide-chain elongation, the blocking the A site of ribosomes, the misreading of the genetic code or the prevention of the attachment of oligosaccharide side chains to glycoproteins. (See all compounds classified as Protein Synthesis Inhibitors.)

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