Human Metabolome Database Version 3.5

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Showing metabocard for Azythromycin (HMDB01916)

Blood
Urine

Record Information

Version

3.5

Creation Date

2006-05-17 09:37:38 -0600

Update Date

2013-02-08 17:11:00 -0700

HMDB ID

HMDB01916

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Azythromycin

Description

Azithromycin is an azalide, a subclass of macrolide antibiotics. Azithromycin is derived from erythromycin; however, it differs chemically from erythromycin in that a methyl-substituted nitrogen atom is incorporated into the lactone ring, thus making the lactone ring 15-membered. Azithromycin is sold under the brand names Zithromax ("Zmax") and Sumamed, and is one of the world's best-selling antibiotics. Azithromycin is used to treat certain bacterial infections, most often bacteria causing middle ear infections, tonsillitis, throat infections, laryngitis, bronchitis, pneumonia and sinusitis. It is also effective against certain sexually transmitted infectious diseases, such as non-gonococcal urethritis and cervicitis.

Structure

Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure

Synonyms

Azithramycine
Azithromycin
Azithromycin (AIDS Initiative)
Azithromycin dihydrate
Azithromycin plus Tumor Necrosis Factor
Azithromycin Sterile
Azithromycine
N,N-Dimethyl-4-amino-benzaldehyde
ZIT
Zithromax

Chemical Formula

C₃₈H₇₂N₂O₁₂

Average Molecular Weight

748.9845

Monoisotopic Molecular Weight

748.508525778

IUPAC Name

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

Traditional IUPAC Name

CAS Registry Number

83905-01-5

SMILES

CC[C@@H]1OC(=O)[C@H](C)[C@@H](O[C@@H]2C[C@](C)(OC)[C@H](O)[C@@H](C)O2)[C@@H](C)[C@H](O[C@H]2O[C@@H](C)C[C@H]([C@@H]2O)N(C)C)[C@@](C)(O)C[C@H](C)CN(C)[C@@H](C)[C@@H](O)[C@]1(C)O

InChI Identifier

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+/m0/s1

InChI Key

MQTOSJVFKKJCRP-HHZDEWPHSA-N

Chemical Taxonomy

Kingdom

Organic Compounds

Super Class

Carbohydrates and Carbohydrate Conjugates

Class

Disaccharides

Sub Class

Dihexoses

Other Descriptors

Aliphatic Heteropolycyclic Compounds
macrolide antibiotic(ChEBI)

Substituents

1,2 Diol
Acetal
Carboxylic Acid Ester
Desosamine
Dialkyl Ether
Glycosyl Compound
Lactone
Macrolide
O Glycosyl Compound
Oxane
Secondary Alcohol
Tertiary Alcohol
Tertiary Aliphatic Amine (Trialkylamine)

Direct Parent

Dihexoses

Ontology

Status

Expected and Not Quantified

Origin

Drug

Biofunction

Not Available

Application

Not Available

Cellular locations

Membrane (predicted from logP)

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	114 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	2.461	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.51 g/L	ALOGPS
LogP	3.03	ALOGPS
LogP	2.44	ChemAxon
LogS	-3.16	ALOGPS
pKa (strongest acidic)	12.43	ChemAxon
pKa (strongest basic)	9.57	ChemAxon
Hydrogen Acceptor Count	13	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	180.08 A²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	194.11	ChemAxon
Polarizability	82.63	ChemAxon
Formal Charge	0	ChemAxon
Physiological Charge	2	ChemAxon