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Natamycin

Natamycin

Synopsis, Chemistry

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Also known as: Pimaricin, Tennecetin, Delvocid, Mycophyt, Myprozine, Synogil

Molecular Formula

C₃₃H₄₇NO₁₃

Molecular Weight

665.7 g/mol

InChI Key

NCXMLFZGDNKEPB-FFPOYIOWSA-N

FDA UNII

8O0C852CPO

Amphoteric macrolide antifungal antibiotic from Streptomyces natalensis or S. chattanoogensis. It is used for a variety of fungal infections, mainly topically.

Natamycin is a Polyene Antimicrobial.

1 2D Structure

Natamycin

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(1R,3S,5R,7R,8E,12R,14E,16E,18E,20E,22R,24S,25R,26S)-22-[(2R,3S,4S,5S,6R)-4-amino-3,5-dihydroxy-6-methyloxan-2-yl]oxy-1,3,26-trihydroxy-12-methyl-10-oxo-6,11,28-trioxatricyclo[22.3.1.05,7]octacosa-8,14,16,18,20-pentaene-25-carboxylic acid

2.1.2 InChI

InChI=1S/C33H47NO13/c1-18-10-8-6-4-3-5-7-9-11-21(45-32-30(39)28(34)29(38)19(2)44-32)15-25-27(31(40)41)22(36)17-33(42,47-25)16-20(35)14-24-23(46-24)12-13-26(37)43-18/h3-9,11-13,18-25,27-30,32,35-36,38-39,42H,10,14-17,34H2,1-2H3,(H,40,41)/b4-3+,7-5+,8-6+,11-9+,13-12+/t18-,19-,20+,21+,22+,23-,24-,25+,27-,28+,29-,30+,32+,33-/m1/s1

2.1.3 InChI Key

NCXMLFZGDNKEPB-FFPOYIOWSA-N

2.1.4 Canonical SMILES

CC1CC=CC=CC=CC=CC(CC2C(C(CC(O2)(CC(CC3C(O3)C=CC(=O)O1)O)O)O)C(=O)O)OC4C(C(C(C(O4)C)O)N)O

2.1.5 Isomeric SMILES

C[C@@H]1C/C=C/C=C/C=C/C=C/[C@@H](C[C@H]2[C@@H]([C@H](C[C@](O2)(C[C@H](C[C@@H]3[C@H](O3)/C=C/C(=O)O1)O)O)O)C(=O)O)O[C@H]4[C@H]([C@H]([C@@H]([C@H](O4)C)O)N)O

2.2 Other Identifiers

2.2.1 UNII

8O0C852CPO

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Myprozine

2. Pimafucin

3. Pimaricin

4. Tennecetin

2.3.2 Depositor-Supplied Synonyms

1. Pimaricin

2. Tennecetin

3. Delvocid

4. Mycophyt

5. Myprozine

6. Synogil

7. 7681-93-8

8. Pimafucin

9. Natacyn

10. Pimaracin

11. Antibiotic A-5283

12. Cl 12,625

13. Pimaricine

14. Delvolan

15. Delvopos

16. Natafucin

17. 8o0c852cpo

18. Ins No.235

19. Ins-235

20. Nsc-759167

21. Cl-12625

22. Ene-25-carboxylic Acid

23. E-235

24. Cl 12625

25. Natamicina

26. Natamycine

27. Natamycinum

28. Pimarizin

29. 6,11,28-trioxatricyclo[22.3.1.05,7]octacosa-8,14,16,18,20-pentaene-25-carboxylic Acid, 22-[(3-amino-3,6-dideoxy-.beta.-d-mannopyranosyl)oxy]-1,3,26-trihydroxy-12-methyl-10-oxo-, (1r,3s,5r,7r,8e,12r,14e,16e,18e,20e,22r,24s,25r,26s)-

30. Pimarizin [german]

31. Natamycin(pimaricin)

32. Natamycine [inn-french]

33. Natamycinum [inn-latin]

34. Natamicina [inn-spanish]

35. Unii-8o0c852cpo

36. Natamycin [usan:usp:inn:ban]

37. Ncgc00016686-01

38. (1r,3s,5r,7r,8e,12r,14e,16e,18e,20e,22r,24s,25r,26s)-22-[(3-amino-3,6-dideoxy-?-d-mannopyranosyl)oxy]-1,3,26-trihydroxy-12-methyl-10-oxo-6,11,28-trioxatricyclo[22.3.1.05,7]octacosa-8,14,16,18,20-penta

39. (1r,3s,5r,7r,8e,12r,14e,16e,18e,20e,22r,24s,25r,26s)-22-[(3-amino-3,6-dideoxy-beta-d-mannopyranosyl)oxy]-1,3,26-trihydroxy-12-methyl-10-oxo-6,11,28-trioxatricyclo[22.3.1.0~5,7~]octacosa-8,14,16,18,20-pentaene-25-carboxylic Acid

40. 6,11,28-trioxatricyclo(22.3.1.05,7)octacosa-8,14,16,18,20-pentaene-25-carboxylic Acid, 22-((3-amino-3,6-dideoxy-.beta.-d-mannopyranosyl)oxy)-1,3,26-trihydroxy-12-methyl-10-oxo-, (1r,3s,5r,7r,8e,12r,14e,16e,18e,20e,22r,24s,25r,26s)-

41. E235

42. Cas-7681-93-8

43. Einecs 231-683-5

44. Mfcd00135085

45. Pimaricin; Natamycin

46. Natamycin [fcc]

47. Natamycin [inn]

48. Pimaricin [jan]

49. Natamycin [mi]

50. Natamycin [inci]

51. Natamycin [usan]

52. Natamycin [vandf]

53. Dsstox_cid_1163

54. Natamycin [mart.]

55. Natamycin [usp-rs]

56. Natamycin [who-dd]

57. Dsstox_rid_75985

58. Dsstox_gsid_21163

59. Schembl18140

60. Natamycin [orange Book]

61. Chembl1200656

62. Natamycin [usp Monograph]

63. Pimaricin 100 Microg/ml In Water

64. Ex-a1989

65. Hy-b0133

66. Zinc8220909

67. Tox21_110561

68. Bdbm50370755

69. Akos030485970

70. Cs-1909

71. Db00826

72. Nsc 759167

73. Nicotinamide_adenine_dinucleotide

74. 16-(3-amino-3,6-didesoxy-beta-d-mannopyranosyloxy)-5,6-epoxy-8,12,14-trihydroxy-26-methyl-2,10-dioxo-1-oxacyclohexacosa-3,17,19,21,23-pentaen-13-carbonsaeure

75. Stereoisomer Of 22-((3-amino-3,6-dideoxy-beta-d-mannopyranosyl)oxy)-1,3,26-trihydroxy-12-methyl-10-oxo-6,11,28-trioxatricyclo(22.3.1.0(sup 5,7))octacosa-8,14,16,18,20-pentaene-25-carboxylic Acid

76. Natamycin, Vetranal(tm), Analytical Standard

77. Ncgc00373238-02_c33h47no13_delvocid

78. 681n938

79. Pimaricin Preparation, ~2.5%, Aqueous Suspension

80. Q248466

81. Natamycin, United States Pharmacopeia (usp) Reference Standard

82. Pimaricin, From Streptomyces Chattanoogensis, >=95% (hplc)

83. Natamycin, Pharmaceutical Secondary Standard; Certified Reference Material

84. (1r,3s,5r,7r,8e,12r,14e,16e,18e,20e,22r,24s,25r,26s)-22-[(2r,3s,4s,5s,6r)-4-amino-3,5-dihydroxy-6-methyloxan-2-yl]oxy-1,3,26-trihydroxy-12-methyl-10-oxo-6,11,28-trioxatricyclo[22.3.1.05,7]octacosa-8,14,16,18,20-pentaene-25-carboxylic Acid

2.4 Create Date

2005-07-19

3 Chemical and Physical Properties

Molecular Formula	C₃₃H₄₇NO₁₃
Molecular Weight	665.7 g/mol
XLogP3	-1.3
Hydrogen Bond Donor Count	7
Hydrogen Bond Acceptor Count	14
Rotatable Bond Count	3
Exact Mass	665.30474055 g/mol
Monoisotopic Mass	665.30474055 g/mol
Topological Polar Surface Area	231 Å²
Heavy Atom Count	47
Formal Charge	0
Complexity	1220
Isotope Atom Count	0
Defined Atom Stereocenter Count	14
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	5
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Information

1 of 2
Drug Name	Natacyn
PubMed Health	Natamycin (Into the eye)
Drug Classes	Antifungal
Drug Label	NATACYN (natamycin ophthalmic suspension) 5% is a sterile, antifungal drug for topical ophthalmic administration. Each mL of the suspension contains: Active: natamycin 5% (50mg). Preservative: benzalkonium chloride 0.02%. Inactive: sodium hydroxi...
Active Ingredient	Natamycin
Dosage Form	Suspension
Route	Ophthalmic
Strength	5%
Market Status	Prescription
Company	Alcon

2 of 2
Drug Name	Natacyn
PubMed Health	Natamycin (Into the eye)
Drug Classes	Antifungal
Drug Label	NATACYN (natamycin ophthalmic suspension) 5% is a sterile, antifungal drug for topical ophthalmic administration. Each mL of the suspension contains: Active: natamycin 5% (50mg). Preservative: benzalkonium chloride 0.02%. Inactive: sodium hydroxi...
Active Ingredient	Natamycin
Dosage Form	Suspension
Route	Ophthalmic
Strength	5%
Market Status	Prescription
Company	Alcon

4.2 Drug Indication

For the treatment of fungal blepharitis, conjunctivitis, and keratitis caused by susceptible organisms including Fusarium solani keratitis.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Natamycin is an antifungal drug for topical ophthalmic administration. It is a tetraene polyene antibiotic derived from Streptomyces natalensis. It possesses in vitro activity against a variety of yeast and filamentous fungi, including Candida, Aspergillus, Cephalosporium, Fusarium and Penicillium. Although the activity against fungi is dose-related, natamycin is predominantly fungicidal. Natamycin is not effective in vitro against gram-positive or gram-negative bacteria. Topical administration appears to produce effective concentrations of natamycin within the corneal stroma but not in intraocular fluid.

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.)

Anti-Infective Agents, Local

Substances used on humans and other animals that destroy harmful microorganisms or inhibit their activity. They are distinguished from DISINFECTANTS, which are used on inanimate objects. (See all compounds classified as Anti-Infective Agents, Local.)

Antifungal Agents

Substances that destroy fungi by suppressing their ability to grow or reproduce. They differ from FUNGICIDES, INDUSTRIAL because they defend against fungi present in human or animal tissues. (See all compounds classified as Antifungal Agents.)

5.3 FDA Pharmacological Classification

5.3.1 Active Moiety

NATAMYCIN

5.3.2 FDA UNII

8O0C852CPO

5.3.3 Pharmacological Classes

Polyenes [CS]; Polyene Antimicrobial [EPC]

5.4 ATC Code

A - Alimentary tract and metabolism

A01 - Stomatological preparations

A01A - Stomatological preparations

A01AB - Antiinfectives and antiseptics for local oral treatment

A01AB10 - Natamycin

A - Alimentary tract and metabolism

A07 - Antidiarrheals, intestinal antiinflammatory/antiinfective agents

A07A - Intestinal antiinfectives

A07AA - Antibiotics

A07AA03 - Natamycin

D - Dermatologicals

D01 - Antifungals for dermatological use

D01A - Antifungals for topical use

D01AA - Antibiotics

D01AA02 - Natamycin

G - Genito urinary system and sex hormones

G01 - Gynecological antiinfectives and antiseptics

G01A - Antiinfectives and antiseptics, excl. combinations with corticosteroids

G01AA - Antibiotics

G01AA02 - Natamycin

S - Sensory organs

S01 - Ophthalmologicals

S01A - Antiinfectives

S01AA - Antibiotics

S01AA10 - Natamycin

5.5 Absorption, Distribution and Excretion

Absorption

Systemic absorption should not be expected following topical administration, and as with other polyene antibiotics, absorption from the gastrointestinal tract is very poor.

5.6 Mechanism of Action

Like other polyene antibiotics, Natamycin inhibits fungal growth by binding to sterols. Specifically, Natamycin binds to ergosterol in the plasma membrane, preventing ergosterol-dependent fusion of vacuoles, as well as membrane fusion and fission. This differs from the mechanism of most other polyene antibiotics, which tend to work by altering fungal membrane permeability instead.