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ACTIVE PHARMA INGREDIENTS

1 API Suppliers, 1 EU WC

1 API Suppliers
1 EU WC

Synopsis

ACTIVE PHARMA INGREDIENTS

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CEP/COS

JDMF

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Chemistry

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Also known as: Rubimycin, Espinomycin a, Platenomycin b1, Turimycin p3, Medecamycin a1, Macropen

Molecular Formula

C₄₁H₆₇NO₁₅

Molecular Weight

814.0 g/mol

InChI Key

DMUAPQTXSSNEDD-QALJCMCCSA-N

FDA UNII

N34Z0Y5UH7

Midecamycin is a naturally occurring 16-membered macrolide that fits under the category of acetoxy-substituted macrolide antibiotics. In this molecule, an acetoxy group is substituted on the position 9 of the 16-member ring and on position 4 of the terminal sugar. Until 2017, midecamycin was still under the list of approved antimicrobial active pharmaceutical ingredients by Health Canada.

1 2D Structure

Midecamycin

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

[(4R,5S,6S,7R,9R,10R,11E,13E,16R)-6-[(2S,3R,4R,5S,6R)-4-(dimethylamino)-3-hydroxy-5-[(2S,4R,5S,6S)-4-hydroxy-4,6-dimethyl-5-propanoyloxyoxan-2-yl]oxy-6-methyloxan-2-yl]oxy-10-hydroxy-5-methoxy-9,16-dimethyl-2-oxo-7-(2-oxoethyl)-1-oxacyclohexadeca-11,13-dien-4-yl] propanoate

2.1.2 InChI

InChI=1S/C41H67NO15/c1-11-30(45)54-29-21-32(47)51-24(4)16-14-13-15-17-28(44)23(3)20-27(18-19-43)37(38(29)50-10)57-40-35(48)34(42(8)9)36(25(5)53-40)56-33-22-41(7,49)39(26(6)52-33)55-31(46)12-2/h13-15,17,19,23-29,33-40,44,48-49H,11-12,16,18,20-22H2,1-10H3/b14-13+,17-15+/t23-,24-,25-,26+,27+,28+,29-,33+,34-,35-,36-,37+,38+,39+,40+,41-/m1/s1

2.1.3 InChI Key

DMUAPQTXSSNEDD-QALJCMCCSA-N

2.1.4 Canonical SMILES

CCC(=O)OC1CC(=O)OC(CC=CC=CC(C(CC(C(C1OC)OC2C(C(C(C(O2)C)OC3CC(C(C(O3)C)OC(=O)CC)(C)O)N(C)C)O)CC=O)C)O)C

2.1.5 Isomeric SMILES

CCC(=O)O[C@@H]1CC(=O)O[C@@H](C/C=C/C=C/[C@@H]([C@@H](C[C@@H]([C@@H]([C@H]1OC)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)C)O[C@H]3C[C@@]([C@H]([C@@H](O3)C)OC(=O)CC)(C)O)N(C)C)O)CC=O)C)O)C

2.2 Other Identifiers

2.2.1 UNII

N34Z0Y5UH7

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Maidimeisu

2. Midecamin

3. Midecamycin Acetate

4. Midecamycin Diacetate

5. Midekamycin

6. Midekamycin Acetate

7. Mosil

8. Mydecamycin

9. Myoxam

10. Neoisomidecamycin

11. Normicina

12. Sf 837

13. Sf-837

2.3.2 Depositor-Supplied Synonyms

1. Rubimycin

2. Espinomycin A

3. Platenomycin B1

4. Turimycin P3

5. Medecamycin A1

6. Macropen

7. Mydecamycin

8. Normicina

9. Myoxam

10. 35457-80-8

11. Midecamycin A1

12. Medemycin A1

13. Momicine

14. Medemycin

15. Mydecamycin A1

16. Leucomycin V, 3,4b-dipropanoate

17. Antibiotic Sf 837

18. N34z0y5uh7

19. Sf 837

20. Madecacine

21. Midecamicina

22. Midecamycine

23. Midecamycinum

24. Yl 704 B1

25. Macro-dil

26. Antibiotic Sf-837

27. Turimycin P(sub 3)

28. Midecamycin A(sub 1)

29. Antibiotic Sf 837 A1

30. Antibiotic Yl 704 B1

31. Midecamycine [inn-french]

32. Midecamycinum [inn-latin]

33. Nsc 154011

34. Midecamicina [inn-spanish]

35. Unii-n34z0y5uh7

36. Midecamycin [inn:dcf:jan]

37. Midecamycin,(s)

38. Nsc-154011

39. Medemycin (tn)

40. Ncgc00016830-01

41. Einecs 252-578-0

42. Cas-35457-80-8

43. Midecamycin [inn]

44. Midecamycin [jan]

45. Midecamycin (jp17/inn)

46. Dsstox_cid_25463

47. Dsstox_rid_80894

48. Midecamycin [mart.]

49. Dsstox_gsid_45463

50. Midecamycin [who-dd]

51. Midecamycin A1 [mi]

52. Schembl141581

53. Chembl444963

54. Dtxsid5045463

55. Chebi:31845

56. (4r,5s,6s,7r,9r,10r,11e,13e,16r)-6-(((2s,3r,4r,5s,6r)-4-(dimethylamino)-3-hydroxy-5-(((2s,4r,5s,6s)-4-hydroxy-4,6-dimethyl-5-(propionyloxy)tetrahydro-2h-pyran-2-yl)oxy)-6-methyltetrahydro-2h-pyran-2-yl)oxy)-10-hydroxy-5-methoxy-9,16-dimethyl-2-oxo-7-(2-oxoethyl)oxacyclohexadeca-11,13-dien-4-yl Propionate

57. Act02621

58. Hy-b1908

59. Tox21_110635

60. S5560

61. Akos022185298

62. Zinc169368401

63. Ccg-270507

64. Cs-5909

65. Db13456

66. Leucomycin V, 3,4(sup B)-dipropanoate

67. D01339

68. H10500

69. Midecamycin), Antibiotic For Culture Media Use Only

70. Q2636110

71. W-106669

72. Espinomycin A;medecamycin A1;platenomycin B1;rubimycin;turimycin P3

73. 7-(formylmethyl)-4,10-dihydroxy-5-methoxy-9,16-dimethyl-2-oxooxacyclohexadeca-11,13-dien-6-yl 3,6-dideoxy-4-o-(2,6-dideoxy-3-c-methyl-alpha-l-ribo-hexopyranosyl)-3-(dimethylamino)-beta-d-glucopyranoside 4',4''-dipropionate (ester)

74. 7-(formylmethyl)-4,10-dihydroxy-5-methoxy-9,16-dimethyl-2-oxooxacyclohexadeca-11,13-dien-6-yl 3,6-dideoxy-4-o-(2,6-dideoxy-3-c-methyl-alpha-l-ribo-hexopyranosyl)-3-(dimethylamino)-beta-d-glucopyranoside 4',4'-dipropionate (ester)

2.4 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₄₁H₆₇NO₁₅
Molecular Weight	814.0 g/mol
XLogP3	2.6
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	16
Rotatable Bond Count	14
Exact Mass	813.45107043 g/mol
Monoisotopic Mass	813.45107043 g/mol
Topological Polar Surface Area	206 Å²
Heavy Atom Count	57
Formal Charge	0
Complexity	1360
Isotope Atom Count	0
Defined Atom Stereocenter Count	16
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	2
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Indication

Midecamycin was used for the treatment of infections in the oral cavity, upper and lower respiratory tracts and skin and soft tissue infections. The alone use of midecamycin was mainly used in Europe or Japan.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Reports have indicated that midecamycin is active against both erythromycin-susceptible and efflux-mediated erythromycin-resistant strains. The diacetate form of this product reduces gastrointestinal side effects and improves its pharmacokinetic profile. Studies have proved that midecamycin is highly active against Gram-positive organisms. The activity of midecamycin in the form of acetate salt presents a better activity, which seems to be potentiated at pH 7-8, as well as a longer half-life.

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.)

5.3 ATC Code

J - Antiinfectives for systemic use

J01 - Antibacterials for systemic use

J01F - Macrolides, lincosamides and streptogramins

J01FA - Macrolides

J01FA03 - Midecamycin

5.4 Absorption, Distribution and Excretion

Absorption

Midecamycin is rapidly and almost completely absorbed when orally administered. It is mainly absorbed in the alkaline intestinal environment. This rapid absorption is due to its liposoluble property which allows for good penetration in the tissues, especially bronchial secretion, prostatic tissue, middle ear exudates and bone tissue. The tissue/serum ratio concentration is greater than 1 which indicates that this product does not stay long in the plasma. After oral administration of 600 mg of midecamycin, the peak serum concentration is 0.8 mg/L and it is attained 1 hour after oral administration. This concentration dereased significantly after 4-6 hours.

Route of Elimination

The major route of elimination of midecamycin is is the liver, followed by a low significance of renal elimination. Urinary concentrations accounts for about 3.3% of the administered dose after 6 hours.

Volume of Distribution

The reported apparent volume of distribution of midecamycin is 7.7 L/kg.

Clearance

Midecamycin presentas a low renal clearance value.

5.5 Metabolism/Metabolites

Midecamycin undergoes extensive biotransformation in the liver and its metabolites are characterized by presenting little to no antimicrobial activity. The main metabolite is formed by a 14-hydroxylation and it can be also detected in urine.

5.6 Biological Half-Life

The half-life of midecamycin is longer than the first macrolide antibiotics. after intravenous administration, the half-life reported is of 54 minutes.

5.7 Mechanism of Action

Midecamycin, as part of the macrolides, act by inhibiting bacterial protein synthesis. More specifically, midecamycin inhibits bacterial growth by targetting the 50S ribosomal subunit preventing peptide bond formation and translocation during protein synthesis. The presence of mutations in the 50S RNA can prevent midecamycin binding. Midecamycin is a broad spectrum antibiotic and thus, it can interact with different bacteria.

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