CAS 83905-01-5|CAS 117772-70-0|Zithromax, Azithrocin, Azin|(2R,3S,4R,5R,8R,10R,11R,12S,13S,14R)-11-{[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy}-2-ethyl-3,4,10-trihydroxy-13-{[(...

General Information

Structure

Molecular Formula

C₃₈H₇₂N₂O₁₂

Molecular Mass

748.98448

Exact Mass

748.50852575

Charge

InChI

InChI=1S/C38H72N2O12/c1-15-27-38(10,46)31(42)24(6)40(13)19-20(2)17-36(8,45)33(52-35-29(41)26(39(11)12)16-21(3)48-35)22(4)30(23(5)34(44)50-27)51-28-18-37(9,47-14)32(43)25(7)49-28/h20-33,35,41-43,45-46H,15-19H2,1-14H3/t20-,21-,22+,23-,24-,25+,26+,27-,28+,29-,30+,31-,32+,33-,35+,36-,37-,38-/m1/s1

InChIKey

MQTOSJVFKKJCRP-BICOPXKESA-N

Canonic Smiles

CC[C@H]1OC(=O)[C@H](C)[C@@H](O[C@@H]2O[C@@H](C)[C@@H]([C@](C2)(C)OC)O)[C@H](C)[C@@H](O[C@@H]2O[C@H](C)C[C@@H]([C@H]2O)N(C)C)[C@](C[C@H](CN([C@@H]([C@H]([C@]1(C)O)O)C)C)C)(C)O

Isomeric Smiles

[C@@H]1([C@@H]([C@H](C[C@H](O1)C)N(C)C)O)O[C@@H]1[C@H]([C@H]([C@H](C(=O)O[C@H]([C@]([C@@H]([C@@H](N(C[C@@H](C[C@]1(O)C)C)C)C)O)(O)C)CC)C)O[C@H]1C[C@]([C@H]([C@@H](O1)C)O)(OC)C)C

Calculated Properties

JChem

LogD (pH = 7.4)

-1.37

LogD (pH = 5.5)

-4.19

Log P

2.44

Rotatable Bonds

H Donor

H Acceptors

Lipinski's Rule of Five

false

Acid pKa

9.68

Polar Surface Area

180.08

Polarizability

82.87

Molar Refractivity

194.11

LOG S

-1.62

Data Source

Names and Identifiers

Brand Name

Zithromax, Azithrocin, AzinHemomycinZithromaxAzigramAzitrominAzenilAzimakrolZmaxAzifast

IUPAC name

(2R,3S,4R,5R,8R,10R,11R,12S,13S,14R)-11-{[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy}-2-ethyl-3,4,10-trihydroxy-13-{[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy}-3,5,6,8,10,12,14-heptamethyl-1-oxa-6-azacyclopentadecan-15-one

Synonyms

ZithromazAzitrocinTrozocinaAzithromycinAzithromycin DihydrateZithromaxXZ-450Trezid(2R,3S,4R,5R,8R,10R,11R,12S,13S,14R)-11-(((2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-2-ethyl-3,4,10-trihydroxy-13-(((2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethylt etrahydro-2H-pyran-2-yl)oxy)-3,5,6,8,10,12,14-heptameth yl-1-oxa-6-azacyclopentadecan-15-one(2R,3S,4R,5R,8R,10R,11R,12S,13S,14R)-13-[(2,6-Dideoxy-3-C-methyl-3-O-methyl-α-L-ribo-hexopyranosyl)oxy]-2-ethyl-3,4,10-trihydroxy-3,5,6,8,10,12,14-heptamethyl-11-[[3,4,6-trideoxy-3-(dimethylamino)-β-D-xylo-hexopyranosyl]oxy]-1-oxa-6-azacyclopentadecan-15-one Dihydrate9-deoxy-9a-aza-9a-methyl-9a-homoerythromycin AZitromaxCP-62993SumamedRibotrexAzithromycin(2R,3S,4R,5R,8R,10R,11R,12S,13S,14R)13-((2,6-Dideoxy-3-C-methyl-3-O-methyl-alpha-L-ribo-hexopyranosyl)oxy)-2-ethyl-3,4,10-trihydroxy-3,5,6,8,10,12,14-heptamethyl-11-((3,4,6-trideoxy-3-(dimethylamino)-beta-D-xylo-hexopyranosyl)oxy)-1-oxa-6-azacyclopentadecan-15-oneazithromycin

IUPAC Traditional name

International Nonproprietary Name (INN)

azitromicinaazithromycineazithromycinum

Names and Identifiers

Registration numbers

Properties

Safety Information

Storage Condition

-20°C Freezer, Under inert atmosphere

MSDS Link

Download link

Physical Property

Melting Point

122-124°C

Apperance

White Solid

Solubility

Chloroform

Ethanol,

Product Information

Certificate of Analysis

Download link

Application(s)

Antibacterial agent

Macrolide antibiotic

Properties

Related Proteins

Molecular Spectra

No Data Available

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Molecule Details

Wikipedia

Azithromycin

TRC

A927000

Semi-synthetic macrolide antibiotic; related to Erythromycin A. Antibacterial.

ChEBI

CHEBI:2955

A macrolide antibiotic useful for the treatment of bacterial infections.

Molecule Details

References

PubChem Literature

From Data Sources

• Langtry, H.D., et al.: Drugs, 56, 273 (1998)

• Peters, D.H. et al., Drugs, 1992, 44, 750, (rev)

• Awan, A. et al., J.C.S. Perkin 2, 2000, 1645-1652, (pmr, conformn)

• Eur. Pat., 1984, Pfizer, 109 253; CA, 101, 211651, (synth, props)

• Djokic, S. et al., J. Chem. Res., Synop., 1988, 152, (deriv, cryst struct)

• Barber, J., Magn. Reson. Chem., 1991, 29, 740, (pmr, cmr)

• Langtry, H.D. et al., Drugs, 1998, 56, 273-297, (rev)

• Girard, A.E. et al., Antimicrob. Agents Chemother., 1987, 31, 1939; 1948, (props)

• Drew, R.H. et al., Pharmacotherapy (Carlisle, Mass.), 1992, 12, 161, (rev)

• Martindale, The Extra Pharmacopoeia, 32nd edn., Pharmaceutical Press, 1999, 155

• Kovacic-Bosnjak, N. et al., Chromatographia, 1988, 25, 999

• Ballow, C.H. et al., Ann. Pharmacother., 1992, 26, 1253, (rev)

• Bright, G.M. et al., J. Antibiot., 1988, 41, 1029, (synth, pharmacol)

• Shepard, R.M. et al., J. Chromatogr., 1991, 565, 321, (hplc)

• Fortner, J.H. et al., Fundam. Appl. Toxicol., 1993, 21, 164, (tox)

• Laufen, H. et al., Arzneim.-Forsch., 1990, 40, 686, (pharmacol)

• Mansoor, G.A. et al., Ann. Intern. Med., 1993, 119, 636, (tox)

References

Bioactivity

PubChem BioAssay

Bioactivity