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Chemistry

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Also known as: 3963-95-9, Metacycline hydrochloride, Methacycline hcl, Rondomycin, Adriamicina, Ciclobiotic
Molecular Formula
C22H23ClN2O8
Molecular Weight
478.9  g/mol
InChI Key
VXPSARQTYDZXAO-CCHMMTNSSA-N
FDA UNII
9GJ0N7ZAP0

Methacycline Hydrochloride
A broad-spectrum semisynthetic antibiotic related to TETRACYCLINE but excreted more slowly and maintaining effective blood levels for a more extended period.
1 2D Structure

Methacycline Hydrochloride

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(4S,4aR,5S,5aR,12aR)-4-(dimethylamino)-1,5,10,11,12a-pentahydroxy-6-methylidene-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboxamide;hydrochloride
2.1.2 InChI
InChI=1S/C22H22N2O8.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;/h4-6,10,14-15,17,25-27,30,32H,1H2,2-3H3,(H2,23,31);1H/t10-,14-,15+,17+,22+;/m1./s1
2.1.3 InChI Key
VXPSARQTYDZXAO-CCHMMTNSSA-N
2.1.4 Canonical SMILES
CN(C)C1C2C(C3C(=C)C4=C(C(=CC=C4)O)C(=C3C(=O)C2(C(=C(C1=O)C(=O)N)O)O)O)O.Cl
2.1.5 Isomeric SMILES
CN(C)[C@H]1[C@@H]2[C@H]([C@@H]3C(=C)C4=C(C(=CC=C4)O)C(=C3C(=O)[C@@]2(C(=C(C1=O)C(=O)N)O)O)O)O.Cl
2.2 Other Identifiers
2.2.1 UNII
9GJ0N7ZAP0
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Lysocline

2. Metacycline

3. Methacycline

4. Methacycline Monohydrochloride

5. Methyleneoxytetracycline

6. Monohydrochloride, Methacycline

7. Physiomycine

8. Rondomycin

2.3.2 Depositor-Supplied Synonyms

1. 3963-95-9

2. Metacycline Hydrochloride

3. Methacycline Hcl

4. Rondomycin

5. Adriamicina

6. Ciclobiotic

7. Germiciclin

8. Metadomus

9. Londomycin

10. Methacycline (hydrochloride)

11. Nsc-356465

12. Nsc-757835

13. 9gj0n7zap0

14. Chebi:6806

15. 2-naphthacenecarboxamide, 4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,5,10,12,12a-pentahydroxy-6-methylene-1,11-dioxo-, Monohydrochloride, (4s,4ar,5s,5ar,12as)-

16. 4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,5,10,12,12a-pentahydroxy-6-methylene-1,11-dioxo-2-naphthacenecarboxamide Monohydrochloride

17. Globociclina

18. Metilenbiotic

19. Physiomycine

20. Megamycine

21. Optimycin

22. Rindex

23. Dsstox_cid_25382

24. Dsstox_rid_80840

25. Dsstox_gsid_45382

26. Metacycline Hydrochloride 100 Microg/ml In Acetonitrile

27. Metacycline Hcl

28. Methacycline Monohydrochloride

29. C22h23cln2o8

30. Einecs 223-568-3

31. Unii-9gj0n7zap0

32. Nsc 356465

33. Sr-05000001769

34. Methacycline Hydrochloride [usp]

35. Rondomycin (tn)

36. Methacycline Hydrochloride (physiomycine)

37. (4s,4ar,5s,5ar,12as)-4-(dimethylamino)-3,5,10,12,12a-pentahydroxy-6-methylidene-1,11-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboxamide;hydrochloride

38. 2-naphthacenecarboxamide,4,4a,5,5a,6,11,12a-octahydro-3,5,10,12,12a-pentahydroxy-6-methylene-1,11-dioxo-, Monohydrochloride, (4s-(4.alpha.,4a.alpha.,5.alpha.,5a.alpha.,12a.alpha.))-

39. 2-naphthacenecarboxamide,4,4a,5,5a,6,11,12a-octahydro-3,5,10,12,12a-pentahydroxy-6-methylene-1,11-dioxo-, Monohydrochloride, [4s-(4.alpha.,4a.alpha.,5.alpha.,5a.alpha.,12a.alpha.)]-

40. Metacyclin Hydrochloride

41. Ncgc00016645-01

42. Cas-3963-95-9

43. Metacycline Hydrochloride Rs

44. Mls000766829

45. Schembl127702

46. Spectrum1501104

47. Chembl2146123

48. Doxycycline Impurity B Hcl Salt

49. Dtxsid5045382

50. Methacycline Hcl (physiomycine)

51. Dtxsid10947932

52. Hms1571a09

53. Hms1921d15

54. Pharmakon1600-01501104

55. (4s,4ar,5s,5ar,12as)-4-(dimethylamino)-3,5,10,12,12a-pentahydroxy-6-methylene-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide Hydrochloride

56. 6-demethyl-6-deoxy-6-methyleneoxytetracycline Monohydrochloride

57. Hy-b0449

58. Tox21_110542

59. Ccg-39016

60. Mfcd04972012

61. Nsc356465

62. Nsc757835

63. S2527

64. Methacycline Hydrochloride (jan/usp)

65. Akos015924655

66. Tox21_110542_1

67. Ac-4567

68. Ks-1240

69. Methacycline Hydrochloride [mi]

70. Methacycline Hydrochloride [jan]

71. Ncgc00179358-04

72. 2-naphthacenecarboxamide, 4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,5,10,12,12a-pentahydroxy-6-methylene-1,11-dioxo-, Monohydrochloride, (4s-(4alpha,4aalpha,5alpha,5aalpha,12aalpha))-

73. 2507-30-4

74. Metacycline Hydrochloride [who-dd]

75. Methacycline Hydrochloride [mart.]

76. Methacycline Hydrochloride [vandf]

77. Methacycline Hydrochloride [usp-rs]

78. C08029

79. D00849

80. Methacycline Hydrochloride [orange Book]

81. 963m959

82. Methacycline Hydrochloride [usp Monograph]

83. Sr-05000001769-2

84. Q27107336

85. Methacycline Hydrochloride, Vetranal(tm), Analytical Standard

86. Methacycline Hydrochloride, Pharmaceutical Secondary Standard; Certified Reference Material

87. Methacycline Hydrochloride, United States Pharmacopeia (usp) Reference Standard

88. (4s,4ar,5s,5ar,12ar)-4-(dimethylamino)-1,5,10,11,12a-pentahydroxy-6-methylene-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboxamide

89. 2-naphthacenecarboxamide,4,4a,5,5a,6,11,12a-octahydro-3,5,10,12,12a-pentahydroxy-6-methylene-1,11-dioxo-, Monohydrochloride, [4s-(4.alpha.,4a.alpha.,5.alpha.,5a.alpha.,12a.alpha.)]

90. 4-(dimethylamino)-1,5,10,11,12a-pentahydroxy-6-methylidene-3,12-dioxo-3,4,4a,5,5a,6,12,12a-octahydrotetracene-2-carboximidic Acid--hydrogen Chloride (1/1)

2.4 Create Date
2011-12-26
3 Chemical and Physical Properties
Molecular Weight 478.9 g/mol
Molecular Formula C22H23ClN2O8
Hydrogen Bond Donor Count7
Hydrogen Bond Acceptor Count9
Rotatable Bond Count2
Exact Mass478.1142934 g/mol
Monoisotopic Mass478.1142934 g/mol
Topological Polar Surface Area182 Ų
Heavy Atom Count33
Formal Charge0
Complexity998
Isotope Atom Count0
Defined Atom Stereocenter Count5
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.)


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Pfizer Inc

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Pfizer Inc

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U.S.A

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