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Home> Encyclopedia >   /  Antibiotic and Antimicrobial Agents  /  Antioxidants  /  Pharmaceutical Intermediates
Natamycin structure
Natamycin structure

Natamycin

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
CAS No.: 7681-93-8
Molecular Weight:665.733
Modify Date.: 2022-10-27 13:10
Introduction: Pimaricin (also known as natamycin, INN) belongs to a naturally occurring antifungal agent produced through the fermentation of the bacterium Streptomyces natalensis. It is a kind of macrolide polyene antifungal used for the treatment of fungal keratitis, which is a kind of eye infection. In medical field, it can be used for the treatment of various kind of fungal infections caused by Candida, Aspergillus, Cephalosporium, Fusarium, and Penicillium. In food industry, it can be used as a natural preservative to prevent fungal outgrowth. Its mechanism of action is through binding to the ergosterol in the plasma membrane of fungi, inhibiting the process of ergosterol-dependent fusion of vacuoles and membrane fusion, further inhibiting the fungal growth. It also inhibit the transport of amino acid and glucose through inhibiting membrane transport proteins. View more+
1. Names and Identifiers
1.1 Name
Natamycin
1.2 Synonyms

(1R,3S,5R,7R,8E,12R,14E,16E,18E,20E,22R,24S,25R,26S)-22-[(3-Amino-3,6-dideoxy-β-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-pentaene-25-carboxylic acid (8E,14E,16E,18E,20E)-(1R,3S,5R,7R,12R,22R,24S,25R,26S)-22-(3-amino-3,6-dideoxy-β-D-mannopyranosyloxy)-1,3,26-trihydroxy-12-methyl-10-oxo-6,11,28-trioxatric (8E,14E,16E,18E,20E)-(1R,3S,5R,7R,12R,22R,24S,25R,26S)-22-(3-amino-3,6-dideoxy-Β-D-mannopyranosyloxy)-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 [1R-(1R*,3S*,5R*,7R*,8E,12R*,14E,16E,18E,20E,22R*,24S*,25R*,26S*)]-22-[(3-Amino-3,6-dideoxy-β-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-pentaene-25-carboxylic acid 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-β-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)- 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-β-D-mannopyranosyl)oxy]-1,3,26-trihydroxy-12-methyl-10-oxo-, [1R-(1R*,3S*,5R*,7R*,8E,12R*,14E,16E,18E,20E,22R*,24S*,25R*,26S*)]- 6,11,28-Trioxatricyclo[22.3.1.05,7]octacosane, pimaricin deriv. Antibiotic A 5283 antibiotica-5283 CL 12625 cl12,625 Delvocid delvolan delvopos E 235 EINECS 231-683-5 MFCD00135085 Mycophyt Myprozine Myuprozine Natacyn Natajen Natamatrix Natamax Natamax lactose Natamax SF Natamycin(FermentionProcess) NataMycin, A 5283, Delvolan, Delvocid, Myprozine, Natacyn, Natafucin, PiMafucin, PiMafugin, A5263, CL 12625, E235 PIMAFUCIN Pimaricin PIMARICIN, STREPTOMYCES CHATTANOOGENSIS Synogil Tennecetin δ-Natamycin

1.3 CAS No.
7681-93-8
1.4 CID
5284447
1.5 EINECS(EC#)
231-683-5
1.6 Molecular Formula
C33H47NO13 (isomer)
1.7 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
1.8 InChkey
NCXMLFZGDNKEPB-FFPOYIOWSA-N
1.9 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
1.10 Isomers 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. Properties
3.1 Density
1.0 g/mL at 20 °C(lit.)
3.1 Melting point
2000 °C
3.1 Boiling point
952.2 °C at 760 mmHg
3.1 Refractive index
1.62
3.1 Flash Point
529.7 °C
3.1 Precise Quality
665.30500
3.1 PSA
230.99000
3.1 logP
0.82000
3.1 Solubility
Soluble in DMSO
3.2 Appearance
white to off-white solid
3.3 Storage

2-8℃

3.4 Chemical Properties
Natamycin (more commonly known as pimaricin) belongs to the polyene macrolide group of antifungal antibiotics. It was derived from Streptomyces natalensis or S. chattanoogensis. In therapeutic use, it is prescribed for a variety of fungal infections, mainly topically, but some ophthalmic applications as well. In addition to therapeutic and food use, pimaricin has applications including use as an agricultural chemical and wood preservative.In the dry state, pimaricin is very stable, as long as it is protected from light and heat, and stability is maintained for a minimum of 1 to 2 years. As long as aqueous suspensions are stored in a cooland dark place, they can be kept for at least six months. Once placed on the surface of the cheese (pimaricin does not penetrate the surface of cheese as do sorbic acid salts), the antimycotic decomposes in about six weeks.
3.5 Color/Form
Powder
3.6 PH
5,5-7,5 (1?% w/v solution in previously neutralised mixture of 20 parts dimethylformamide and 80 parts of water)
3.7 Physical
White to creamy-white crystalline powder
3.8 pKa
pKa 4.6(50% aq. MeOEtOH) (Uncertain);8.35 (Uncertain)
3.9 Water Solubility
Insoluble
3.10 Stability
Light sensitive
3.11 StorageTemp
2-8°C
3. Use and Manufacturing
4.1 Usage
Natamycin (l), from Streptomyces nataIensis and Streptomyces chat tanoogensis,is used for the control of diseases of bulbs.
4. Safety and Handling
5.1 Hazard Codes
Xn
5.1 Risk Statements
R22
5.1 Safety Statements
S24/25
5.1 Safety Profile
Poison by intravenous,intramuscular, subcutaneous, andintraperitoneal routes. Moderately toxic byingestion. When heated to decomposition it emits toxic fumes of NOx. Used as anantibacterial agent.
5.2 WGK Germany
2
5.2 RTECS
TK3325000
5.2 Safety

Poison by intravenous, intramuscular, subcutaneous, and intraperitoneal routes. Moderately toxic by ingestion. When heated to decomposition, it emits toxic fumes of NOx.
Hazard Codes:??HarmfulXn
Risk Statements:? 22?
R22:Harmful if swallowed.
Safety Statements:? 24/25-36?
S24/25:Avoid contact with skin and eyes.?
S36:Wear suitable protective clothing.
WGK Germany:? 2
RTECS:? TK3325000
F:? 8-10

5.3 Specification

?Pimaricin (CAS NO.7681-93-8) is a naturally occurring antifungal agent produced during fermentation by the bacterium Streptomyces natalensis, commonly found in soil. It has some synonyms like Natamycin ; Pimaricin approx. 2.5% aqueous*suspension gamma-I ; Pimafucin (pimaricin in 2.5% sterile water suspen ; Pimaricin, Streptomyces chattanoogensis (1.07360) and so on.

5.4 Toxicity
1. ???

orl-rat LD50:2730?mg/kg

??? TXAPA9 ?? Toxicology and Applied Pharmacology. 8 (1966),97.
2. ???

ipr-rat LD50:85?mg/kg

??? ANTCAO ?? Antibiotics and Chemotherapy. 9 (1959),406.
3. ???

scu-rat LD50:190?mg/kg

??? ANTCAO ?? Antibiotics and Chemotherapy. 9 (1959),406.
4. ???

ivn-rat LD50:36?mg/kg

??? ANTCAO ?? Antibiotics and Chemotherapy. 9 (1959),406.
5. ???

ims-rat LD50:128?mg/kg

??? ANTCAO ?? Antibiotics and Chemotherapy. 9 (1959),406.
6. ???

orl-mus LD50:1500?mg/kg

??? 85FZAT ?? Index of Antibiotics from Actinomycetes Umezawa, H., et al., eds.,Tokyo, Japan.:?University of Tokyo Press,1967,517.
7. ???

ipr-mus LD50:96?mg/kg

??? NIIRDN ?? “Drugs in Japan. Ethical Drugs, 6th Edition 1982” Edited by Japan Pharmaceutical Information Center. 6 (1982),639.
8. ???

ivn-dog LD50:18?mg/kg

??? ANTCAO ?? Antibiotics and Chemotherapy. 9 (1959),406.
9. ???

orl-rbt LD50:1420?mg/kg

??? TXAPA9 ?? Toxicology and Applied Pharmacology. 8 (1966),97.???????????????????????
5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Not classified.

2.2 GHS label elements, including precautionary statements

Pictogram(s) No symbol.
Signal word

No signal word.

Hazard statement(s)

none

Precautionary statement(s)
Prevention

none

Response

none

Storage

none

Disposal

none

2.3 Other hazards which do not result in classification

none

6. Other Information
6.0 Usage
Pimaricin is an amphoteric antibiotic from Streptomyces chattanoogensis. It is used as an ergosterol and cholesterol binding agent to study lipid bilayer dynamics. It is used to study the pleitropic regulator AdpAch and the gamma-butyrolactone regulatory system of Streptomyces chattanoogensis.
7. Computational chemical data
  • Molecular Weight: 665.733g/mol
  • Molecular Formula: C33H47NO13
  • Compound Is Canonicalized: True
  • XLogP3-AA: -1.3
  • Exact Mass: 665.30474055
  • Monoisotopic Mass: 665.30474055
  • Complexity: 1220
  • Rotatable Bond Count: 3
  • Hydrogen Bond Donor Count: 7
  • Hydrogen Bond Acceptor Count: 14
  • Topological Polar Surface Area: 231
  • Heavy Atom Count: 47
  • Defined Atom Stereocenter Count: 14
  • Undefined Atom Stereocenter Count: 0
  • Defined Bond Stereocenter Count: 5
  • Undefined Bond Stereocenter Count: 0
  • Isotope Atom Count: 0
  • Covalently-Bonded Unit Count: 1
  • CACTVS Substructure Key Fingerprint: AAADcfB+PAAAAAAAAAAAAAAAEgAAAAAAAAAkSAAAAAAAAAAAAAAAHgAQCAAADTzxgAcCCABABgCIACDSCAAAAAAgAAAICIEAAEgbFBYAoQAiUAAH8AAPoYPI7OzOAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==
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