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Chlortetracycline

Synopsis, Chemistry

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Also known as: 57-62-5, 7-chlorotetracycline, Chlorotetracycline, Aureomycin, Acronize, Chlormax

Molecular Formula

C₂₂H₂₃ClN₂O₈

Molecular Weight

478.9 g/mol

InChI Key

DHPRQBPJLMKORJ-XRNKAMNCSA-N

FDA UNII

WCK1KIQ23Q

A TETRACYCLINE with a 7-chloro substitution.

1 2D Structure

Chlortetracycline

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

2.1.2 InChI

InChI=1S/C22H23ClN2O8/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)/t7-,8-,15-,21-,22-/m0/s1

2.1.3 InChI Key

DHPRQBPJLMKORJ-XRNKAMNCSA-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

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

2.2 Other Identifiers

2.2.1 UNII

WCK1KIQ23Q

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 Bisulfate

10. Chlortetracycline Hydrochloride

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. 57-62-5

2. 7-chlorotetracycline

3. Chlorotetracycline

4. Aureomycin

5. Acronize

6. Chlormax

7. Clortetraciclina

8. Chlortetracyclinum

9. Aureomycin A-377

10. Biomycin

11. (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

12. Duomycin

13. Wck1kiq23q

14. Aureomykoin

15. Chrysomykine

16. Aureocina

17. Biomitsin

18. Flamycin

19. Uromycin

20. Biomycin A

21. Chebi:27644

22. Ctc (abtibiotic)

23. Tri-chlortetracycline

24. Aureomycin (tn)

25. Chlortetracycline (inn)

26. Chlortetracycline [inn]

27. Caswell No. 219b

28. Unii-wck1kiq23q

29. Aueromycin

30. Chlortetracycline [inn:ban]

31. Chlortetracyclinum [inn-latin]

32. Clortetraciclina [inn-spanish]

33. 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-, (4s,4as,5as,6s,12as)-

34. Einecs 200-341-7

35. Mfcd00864876

36. Epa Pesticide Chemical Code 006301

37. Spectrum_000727

38. Spectrum_001315

39. Prestwick0_000145

40. Prestwick1_000145

41. Prestwick2_000145

42. Spectrum2_000802

43. Spectrum3_000348

44. Spectrum4_001001

45. Spectrum4_001791

46. Spectrum5_000461

47. Spectrum5_001870

48. Pig Liver-chlortetracycline

49. Schembl3110

50. Pig Kidney (ctc Free)

51. Pig Muscle (ctc Free)

52. Schembl62861

53. Bspbio_002015

54. Kbiogr_001461

55. Kbiogr_002364

56. Kbioss_001207

57. Kbioss_001795

58. Chlortetracycline [mi]

59. Divk1c_000253

60. Spbio_000663

61. Spbio_002189

62. Chembl404520

63. Schembl4099094

64. Chembl1622557

65. Dtxsid9022811

66. Schembl19981439

67. Chlortetracycline [vandf]

68. Hms500m15

69. Hy-b1327a

70. Kbio1_000253

71. Kbio2_001207

72. Kbio2_001795

73. Kbio2_003775

74. Kbio2_004363

75. Kbio2_006343

76. Kbio2_006931

77. Kbio3_001235

78. Chlortetracycline [mart.]

79. Ninds_000253

80. Chlortetracycline [who-dd]

81. (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

82. Rkl10090

83. Lmpk07000004

84. Zinc19701769

85. Chlortetracycline [green Book]

86. Zinc100154659

87. Zinc100302624

88. Ccg-269531

89. Chlortetracycline [ep Impurity]

90. Db09093

91. Idi1_000253

92. Ncgc00178862-01

93. Ncgc00178862-04

94. E702

95. Sbi-0051312.p003

96. Cs-0013541

97. Lymecycline Impurity G [ep Impurity]

98. C06571

99. D07689

100. H10649

101. Ab00643434_03

102. 864c876

103. Q417948

104. Q-200843

105. (4s,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

2.4 Create Date

2011-12-26

3 Chemical and Physical Properties

Molecular Formula	C₂₂H₂₃ClN₂O₈
Molecular Weight	478.9 g/mol
XLogP3	-1.3
Hydrogen Bond Donor Count	6
Hydrogen Bond Acceptor Count	9
Rotatable Bond Count	2
Exact Mass	478.1142934 g/mol
Monoisotopic Mass	478.1142934 g/mol
Topological Polar Surface Area	182 Å²
Heavy Atom Count	33
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	1

4 Drug and Medication Information

4.1 Drug Indication

Used in the manufacuring of medicated animal feeds.

FDA Label

5 Pharmacology and Biochemistry

5.1 Pharmacology

Tetracycline antibiotics are bacteriostatic agents which act to inhibit bacterial growth and reproduction.

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.)

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.)

5.3 ATC Code

S01AA02

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

A01AB21 - Chlortetracycline

D - Dermatologicals

D06 - Antibiotics and chemotherapeutics for dermatological use

D06A - Antibiotics for topical use

D06AA - Tetracycline and derivatives

D06AA02 - Chlortetracycline

J - Antiinfectives for systemic use

J01 - Antibacterials for systemic use

J01A - Tetracyclines

J01AA - Tetracyclines

J01AA03 - Chlortetracycline

S - Sensory organs

S01 - Ophthalmologicals

S01A - Antiinfectives

S01AA - Antibiotics

S01AA02 - Chlortetracycline

5.4 Absorption, Distribution and Excretion

Absorption

Chortetracycline reaches peak plasma concentation in about 3 hours. Its oral bioavailability is 25-30%.

Route of Elimination

Chlortetracycline is mainly eliminated in feces. Renal function does not appear to affect the rate of elimination.

Volume of Distribution

Chlortetracycline has a volume of distribution of 100 liters.

5.5 Metabolism/Metabolites

Chlortetracycline is not known to undergo significant metabolism.

5.6 Biological Half-Life

The half-life of Chlortetracycline is 5.6 hours.

5.7 Mechanism of Action

Chlortetracycline, like other tetracyclines, competes for the A site of the bacterial ribosome. This binding competes with tRNA carrying amino acids preventing the addition of more amino acids to the peptide chain. This inhibition of protein synthesis ultimately inhibits growth and reproduction of the bacterial cell as necessary proteins cannot be synthesized.