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| CAS No.: | 114-07-8 |
|---|---|
| Name: | Erythromycin |
| Article Data: | 25 |
| Molecular Structure: | |
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|
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| Formula: | C37H67NO13 |
| Molecular Weight: | 733.938 |
| 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: |
 Xn, Xi
|
| Risk Codes: | 42/43-36/37/38 |
| Safety: | 45-37-24-36-26 |
| PSA: | 193.91000 |
| LogP: | 1.78560 |
- 144851-82-1METHYL2-AMINO-3-FLUOROBENZOATE
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- 81281-59-67-Benzylideneaminotheophylline
- 50288-62-5threo-Phenyl-2-piperidyl acetamide
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| Conditions | Yield |
|---|---|
| With sodium hydroxide In methanol at 40℃; pH=9-9.8; | 99.33% |
| With ammonia In dichloromethane; water at 25 - 35℃; | |
| In dichloromethane; water at 37℃; pH=12; Product distribution / selectivity; | |
| With ammonia In water at 35 - 70℃; for 1.5h; Reagent/catalyst; | 106 g |
| Conditions | Yield |
|---|---|
| With hydrogen; Raney-Ni (W4) In ethanol at 25℃; for 1h; | 84% |
| With hydrogen; Rany Ni (W4) In ethanol at 25℃; for 1h; | 84% |
- 119665-62-2
(2',4''-O-bistrimethylsilyl)-6-O-methylerythromycinA-9[O-(1-ethoxy-1-methylethyl)]oxime
- 114-07-8
erythromycin
| Conditions | Yield |
|---|---|
| With formic acid; water; sodium hydrogensulfite In ethanol for 8h; Heating; | 66.7% |
| Conditions | Yield |
|---|---|
| With sodium cyanoborohydride In methanol; water for 0.5h; Ambient temperature; | A 11.4% B n/a |
| Conditions | Yield |
|---|---|
| In methanol; water for 0.5h; Ambient temperature; | A 11.4% B n/a |
- 30760-16-8
9-deoxo-9-iminoerythromycin A
- 114-07-8
erythromycin
| Conditions | Yield |
|---|---|
| With water at 5℃; Yield given; | |
| With water In methanol at 23℃; pH 7, methanol-phosphate buffer, various pH, other erythromycin; | |
| With hydrogenchloride; water In ethanol pH=5 - 6; |
- 123943-98-6
9-N,11-O-benzylidene-9-deoxo-9-iminoerythromycin A
- 114-07-8
erythromycin
| Conditions | Yield |
|---|---|
| With water at 37℃; Rate constant; pH 7 (1:1 methanol-phosphate buffer); |
- 123944-04-7
C45H74N2O12
- 114-07-8
erythromycin
| Conditions | Yield |
|---|---|
| With water at 37℃; Rate constant; pH 7 (1:1 methanol-phosphate buffer); |
- 123944-06-9
C44H71ClN2O12
- 114-07-8
erythromycin
| Conditions | Yield |
|---|---|
| With water at 37℃; Rate constant; pH 7 (1:1 methanol-phosphate buffer); |
- 123944-10-5
C45H74N2O13
- 114-07-8
erythromycin
| Conditions | Yield |
|---|---|
| With water at 37℃; Rate constant; pH 7 (1:1 methanol-phosphate buffer); |
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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%.
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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. |