ContaminantDB: Azithromycin

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (1)XML

Record Information

Version

1.0

Creation Date

2016-05-22 04:14:14 UTC

Update Date

2026-05-14 16:24:40 UTC

Accession Number

CHEM017314

Identification

Common Name

Azithromycin

Class

Small Molecule

Description

Azithromycin is a broad-spectrum macrolide antibiotic with a long half-life and a high degree of tissue penetration . It was initially approved by the FDA in 1991 . It is primarily used for the treatment of respiratory, enteric and genitourinary infections and may be used instead of other macrolides for some sexually transmitted and enteric infections. It is structurally related to erythromycin . Azithromycin is a part of the _azalide_ subclass of macrolides, and contains a 15-membered ring, with a methyl-substituted nitrogen instead of a carbonyl group at the 9a position on the aglycone ring, which allows for the prevention of its metabolism. This differentiates azithromycin from other types of macrolides .

Contaminant Sources

FooDB Chemicals
HMDB Contaminants - Urine
STOFF IDENT Compounds
Suspected Compounds - Waste Water
ToxCast & Tox21 Chemicals

Contaminant Type

Human Neurotoxin
PMT

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(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-one	ChEBI
Azenil	ChEBI
Azifast	ChEBI
Azigram	ChEBI
Azimakrol	ChEBI
Azithromycine	ChEBI
Azithromycinum	ChEBI
Azitromicina	ChEBI
Azitromin	ChEBI
Hemomycin	ChEBI
Zithromax	ChEBI
Zmax	ChEBI
(2R,3S,4R,5R,8R,10R,11R,12S,13S,14R)13-((2,6-Dideoxy-3-C-methyl-3-O-methyl-a-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)-b-D-xylo-hexopyranosyl)oxy)-1-oxa-6-azacyclopentadecan-15-one	Generator
(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	Generator
Azithramycine	HMDB
Azithromycin dihydrate	HMDB
Azythromycin	HMDB
Dihydrate, azithromycin	HMDB
Monohydrate, azithromycin	HMDB
Pfizer brand OF azithromycin	HMDB
Azadose	HMDB
Azitrocin	HMDB
Funk brand OF azithromycin dihydrate	HMDB
Pharmacia brand OF azithromycin dihydrate	HMDB
Sumamed	HMDB
Zentavion	HMDB
Azithromycin monohydrate	HMDB
Azithromycin pfizer brand	HMDB
Goxal	HMDB
Mack brand OF azithromycin dihydrate	HMDB
Toraseptol	HMDB
Bayer brand OF azithromycin dihydrate	HMDB
Lesvi brand OF azithromycin dihydrate	HMDB
Pfizer brand OF azithromycin dihydrate	HMDB
Ultreon	HMDB
Vinzam	HMDB
Vita brand OF azithromycin dihydrate	HMDB
Zitromax	HMDB

Chemical Formula

C₃₈H₇₂N₂O₁₂

Average Molecular Mass

748.985 g/mol

Monoisotopic Mass

748.509 g/mol

CAS Registry Number

83905-01-5

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

Traditional Name

azithromycin

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-/m1/s1

InChI Key

MQTOSJVFKKJCRP-BICOPXKESA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as aminoglycosides. These are molecules or a portion of a molecule composed of amino-modified sugars.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Aminoglycosides

Alternative Parents

Substituents

Aminoglycoside core
Macrolide
Glycosyl compound
O-glycosyl compound
Monosaccharide
Oxane
Tertiary alcohol
1,2-aminoalcohol
Amino acid or derivatives
Carboxylic acid ester
Lactone
Secondary alcohol
Tertiary amine
Tertiary aliphatic amine
Oxacycle
Acetal
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Polyol
Azacycle
Ether
Dialkyl ether
Carboxylic acid derivative
Organic nitrogen compound
Alcohol
Carbonyl group
Organonitrogen compound
Organopnictogen compound
Amine
Organic oxide
Hydrocarbon derivative
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

macrolide antibiotic (CHEBI:2955 )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.51 g/L	ALOGPS
logP	3.03	ALOGPS
logP	2.44	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	12.43	ChemAxon
pKa (Strongest Basic)	9.57	ChemAxon
Physiological Charge	2	ChemAxon
Hydrogen Acceptor Count	13	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	180.08 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	194.11 m³·mol⁻¹	ChemAxon
Polarizability	82.93 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	0	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-9400002500-41dea9c95a10a1b1de40	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_5) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_7) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_8) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_9) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_10) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_4) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_5) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-0f6t-0300030900-1a7ea512a0aa566e59ed	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-066r-4911100000-f759f24274aebce8e08c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-052f-3912280200-df9a72a4769570064ef9	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-004l-0309050000-5e1be028a242f0d384eb	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-0f6t-0300030900-1a7ea512a0aa566e59ed	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-066r-4911100000-f759f24274aebce8e08c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-052f-3912280200-df9a72a4769570064ef9	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - -1V, Positive	splash10-052g-1500090600-c927b1d59baafc36f28a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-007p-0200290400-6b26ce4eae1da4ab7539	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-008c-1400980000-bd2668df569167cd3578	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052f-9202600000-d73ef5fca5d0b7f57440	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-002n-1711270900-c52a335bcbed8f5697ac	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-055u-1301292100-964dbaabd967748c6585	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-4310960000-a18b1f6c98eecf56c1a4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-0000000900-e672b5dc6a5cbe904a20	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-05i4-2900060400-4207a30e8e22ff575ffa	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-8900010000-9f3cd28580ffd31cbfe4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0000010900-0a636d0c8349389b6fca	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-006t-1900010600-77547434176448b7b870	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-3900000300-261e118cc7c9d298dc58	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	Spectrum