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114-07-8

Basic Information
CAS No.: 114-07-8
Name: Erythromycin
Molecular Structure:
Molecular Structure of 114-07-8 (Erythromycin)
Formula: C37H67NO13
Molecular Weight: 733.93
Synonyms: Erythromycin A;Erymax;Pentadecanoic acid, 3-[(2, 6-dideoxy-3-C-methyl-3-O-methyl-.alpha.-L-ribo-hexopyranosyl)oxy]- 6,11,12,13-tetrahydroxy-2,4,6,8,10,12-hexamethyl-9-oxo-5-[[3,4, 6-trideoxy-3-(dimethylamino)-.beta.-D-xylo-hexopyranosyl]oxy]-, .mu.-lactone, [2R-(2R*,3S*,4S*,5R*,6R*,8R*,10R*,11R*,12S*,13S*)]-;Taimoxin-F;EM;Abomacetin;Abboticin;Erythro;Kesso-Mycin;Erythromid;Erycin;Propiocine;Ilotycin;Prestwick_205;6-(4-dimethylamino-3-hydroxy-6-methyl-oxan-2-yl)oxy-14-ethyl-7,12,13-trihydroxy-4-(5-hydroxy-4-methoxy-4,6-dimethyl-oxan-2-yl)oxy-3,5,7,9,11,13-hexamethyl-1-oxacyclotetradecane-2,10-dione;Oxacyclotetradecane-2,10-dione, 4-[(2, 6-dideoxy-3-C-methyl-3-O-methyl-.alpha.-L-ribo-hexopyranosyl)oxy]- 14-ethyl-7,12,13-trihydroxy-3,5,7,9,11,13-hexamethyl-6-[[3,4, 6-trideoxy-3-(dimethylamino)-.beta.-D-xylo-hexopyranosyl]oxy]-, [2R-(2R*,3S*,4S*,5R*,6R*,8R*,10R*,11R*,12S*,13S*)]-;
EINECS: 204-040-1
Density: 1.209 g/cm3
Melting Point: 138-140 °C
Boiling Point: 818.401 °C at 760 mmHg
Flash Point: 448.753 °C
Solubility: soluble in ethanol, methanol and chloroform, insoluble in water
Appearance: white to off white crystalline powder
Hazard Symbols: HarmfulXn,IrritantXi
Risk Codes: 42/43-36/37/38
Safety: 45-37-24-36-26
Transport Information:
PSA: 193.91000
LogP: 1.78560
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History

1、Lilly filed for patent protection of the compound and U.S. patent 2,653,899 was granted in 1953. The product was launched commercially in 1952 under the brand name Ilosone.
2、In 1981, Nobel laureate (1965 in chemistry) and Professor of Chemistry at Harvard University (Cambridge, MA) Robert B. Woodward, along with a large number of members from his research group, posthumously reported the first stereocontrolled asymmetric chemical synthesis of Erythromycin A.
3、The antiobiotic clarithromycin was invented by scientists at the Japanese drug company Taisho Pharmaceutical in the 1970s as a result of their efforts to overcome the acid instability ofErythromycin (CAS NO.114-07-8).
4、Presently, Erythromycin (CAS NO.114-07-8) is commonly used off-label for gastric motility indications such as Gastroparesis.

Consensus Reports

EPA Genetic Toxicology Program.

Specification

The Erythromycin, with the CAS registry number 114-07-8, is also known as Abboticin. It belongs to the product categories of Antibiotics; Organics; Antibiotics for Research and Experimental Use; Biochemistry; Macrolides (Antibiotics for Research and Experimental Use); Antibiotic Explorer; Intermediates & Fine Chemicals; Pharmaceuticals; Immune System Regulation; MacrolidesMore...Close...; Antibiotics A-FAlphabetic; EQ - EZAntibiotics; Chemical Structure Class; Core Bioreagents; Interferes with Protein Synthesis Antibiotics; Mechanism of Action; Pharmacopoeia A-ZPharmacopoeia (USP); Spectrum of Activity; Macrolides; A - KCell Culture; Reagents and Supplements; API's. Its EINECS number is 204-040-1. This chemical's molecular formula is C37H67NO13 and molecular weight is 733.93. What's more, its systematic name is (3R,4S,5S,6R,7R,9R,11R,12R,13S,14R)-6-{[(2S,3R,4S,6R)-4-(Dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl]oxy}-14-ethyl-7,12,13-trihydroxy-4-{[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethylte trahydro-2H-pyran-2-yl]oxy}-3,5,7,9,11,13-hexamethyloxacyclotetradecane-2,10-dione. Its classification codes are: (1)Anti-Bacterial Agents; (2)Anti-Infective Agents; (3)Antibacterial; (4)Drug / Therapeutic Agent; (5)Enzyme Inhibitors; (6)Gastrointestinal agents; (7)Human Data; (8)Mutation data; (9)Natural Product; (10)Protein synthesis inhibitors; (11)Reproductive Effect. This chemical is a macrolide antibiotic that has an antimicrobial spectrum similar to or slightly wider than that of penicillin, and is often used for people who have an allergy to penicillins. Erythromycin is available in enteric-coated tablets, slow-release capsules, oral suspensions, ophthalmic solutions, ointments, gels, and injections.

Physical properties of Erythromycin are: (1)ACD/LogP: 1.909; (2)# of Rule of 5 Violations: 3; (3)ACD/LogD (pH 5.5): -0.54; (4)ACD/LogD (pH 7.4): 1.16; (5)ACD/BCF (pH 5.5): 1.00; (6)ACD/BCF (pH 7.4): 2.98; (7)ACD/KOC (pH 5.5): 1.00; (8)ACD/KOC (pH 7.4): 46.71; (9)#H bond acceptors: 14; (10)#H bond donors: 5; (11)#Freely Rotating Bonds: 12; (12)Polar Surface Area: 193.91 Å2; (13)Index of Refraction: 1.535; (14)Molar Refractivity: 189.169 cm3; (15)Molar Volume: 607.183 cm3; (16)Polarizability: 74.992×10-24cm3; (17)Surface Tension: 51.42 dyne/cm; (18)Density: 1.209 g/cm3; (19)Flash Point: 448.753 °C; (20)Enthalpy of Vaporization: 135.404 kJ/mol; (21)Boiling Point: 818.401 °C at 760 mmHg; (22)Vapour Pressure: 0 mmHg at 25°C.

Preparation: it is a kind of Alkaline antibiotics extracted from culture solution of Streptomyces erythreus. During the process of purification, use butyl acetate and aqueous solution to ectract again and again to achieve the purpose of concentration purification. Finally, the products are got by freezing crystallization in the solution of butyl acetate.

Uses of Erythromycin: it can be used to produce pseudoerythromycin A enol ether and erythromycin A enol ether at the temperature of 70 °C. It will need reagents pyridine, acetic acid with the reaction time of 24 hours. The yield is about 71%.

Erythromycin can be used to produce pseudoerythromycin A enol ether and erythromycin A enol ether at the temperature of 70 °C

When you are using this chemical, please be cautious about it as the following:
This chemical is irritating to eyes, respiratory system and skin. It may cause sensitisation by inhalation and skin contact. You must avoid contact with skin. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. When using it, you need to wear suitable protective clothing and gloves. In case of accident or if you feel unwell, you should seek medical advice immediately (show the label where possible).

You can still convert the following datas into molecular structure:
(1)SMILES: CC[C@@H]1[C@@]([C@@H]([C@H](C(=O)[C@@H](C[C@@]([C@@H]([C@H]([C@@H]([C@H](C(=O)O1)C)O[C@H]2C[C@@]([C@H]([C@@H](O2)C)O)(C)OC)C)O[C@H]3[C@@H]([C@H](C[C@H](O3)C)N(C)C)O)(C)O)C)C)O)(C)O
(2)Std. InChI: InChI=1S/C37H67NO13/c1-14-25-37(10,45)30(41)20(4)27(39)18(2)16-35(8,44)32(51-34-28(40)24(38(11)12)15-19(3)47-34)21(5)29(22(6)33(43)49-25)50-26-17-36(9,46-13)31(42)23(7)48-26/h18-26,28-32,34,40-42,44-45H,14-17H2,1-13H3/t18-,19-,20+,21+,22-,23+,24+,25-,26+,28-,29+,30-,31+,32-,34+,35-,36-,37-/m1/s1
(3)Std. InChIKey: ULGZDMOVFRHVEP-RWJQBGPGSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
child TDLo oral 10mg/kg/1D-I (10mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) Annals of Internal Medicine. Vol. 115, Pg. 69, 1991.
child TDLo oral 250mg/kg (250mg/kg) GASTROINTESTINAL: NAUSEA OR VOMITING

GASTROINTESTINAL: OTHER CHANGES

BLOOD: CHANGES IN LEUCOCYTE (WBC) COUNT
Pediatrics. Vol. 90, Pg. 624, 1992.
dog LDLo unreported > 100mg/kg (100mg/kg)   Antibiotics and Chemotherapy Vol. 2, Pg. 281, 1952.
guinea pig LD50 intraperitoneal 413mg/kg (413mg/kg)   Journal of the American Pharmaceutical Association, Scientific Edition. Vol. 41, Pg. 555, 1952.
hamster LD50 oral 3018mg/kg (3018mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Journal of the American Pharmaceutical Association, Scientific Edition. Vol. 41, Pg. 555, 1952.
mouse LD50 intramuscular 394mg/kg (394mg/kg)   Journal of the American Pharmaceutical Association, Scientific Edition. Vol. 44, Pg. 199, 1955.
mouse LD50 intraperitoneal 280mg/kg (280mg/kg)   Journal of Antibiotics. Vol. 43, Pg. 938, 1990.
mouse LD50 intravenous 426mg/kg (426mg/kg)   "Index of Antibiotics from Actinomycetes," Umezawa, H. et al., eds., Tokyo, Univ. of Tokyo Press, 1967Vol. -, Pg. 273, 1967.
mouse LD50 oral 2580mg/kg (2580mg/kg)   Acta Poloniae Pharmaceutica. For English translation, see APPFAR. Vol. 31, Pg. 241, 1974.
mouse LD50 subcutaneous 1800mg/kg (1800mg/kg)   Antibiotics and Chemotherapy Vol. 2, Pg. 281, 1952.
rat LD50 oral 4600mg/kg (4600mg/kg)   Acta Poloniae Pharmaceutica. For English translation, see APPFAR. Vol. 31, Pg. 241, 1974.
rat LDLo subcutaneous 427mg/kg (427mg/kg)   Compilation of LD50 Values of New Drugs.