ContaminantDB: Tetracycline

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (12)XML

Record Information

Version

1.0

Creation Date

2014-08-28 21:19:25 UTC

Update Date

2026-05-14 16:48:06 UTC

Accession Number

CHEM002915

Identification

Common Name

Tetracycline

Class

Small Molecule

Description

Tetracycline is a broad spectrum polyketide antibiotic produced by the Streptomyces genus of Actinobacteria. It exerts a bacteriostatic effect on bacteria by binding reversible to the bacterial 30S ribosomal subunit and blocking incoming aminoacyl tRNA from binding to the ribosome acceptor site. It also binds to some extent to the bacterial 50S ribosomal subunit and may alter the cytoplasmic membrane causing intracellular components to leak from bacterial cells.

Contaminant Sources

HMDB Contaminants - Urine
STOFF IDENT Compounds
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Anti-Bacterial Agent
Antiprotozoal Agent
Drug
Human Neurotoxin
Metabolite
Organic Compound
Protein Synthesis Inhibitor
Synthetic Compound
Tetracycline

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(4S,4AS,5as,12as)-4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-2-naphthacenecarboxamide	ChEBI
Abramycin	ChEBI
Achromycin	ChEBI
Anhydrotetracycline	ChEBI
Deschlorobiomycin	ChEBI
Liquamycin	ChEBI
Tetracyclin	ChEBI
Tetracyclinum	ChEBI
Tetrazyklin	ChEBI
Tsiklomitsin	ChEBI
TC	Kegg
Sumycin	Kegg
Tetracycline HCL	HMDB

Chemical Formula

C₂₂H₂₄N₂O₈

Average Molecular Mass

444.435 g/mol

Monoisotopic Mass

444.153 g/mol

CAS Registry Number

60-54-8

IUPAC Name

(4S,4aS,5aS,6S,12aS)-4-(dimethylamino)-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide

Traditional Name

tetracycline

SMILES

[H][C@@]12C[C@@]3([H])C(=C(O)[C@]1(O)C(=O)C(C(N)=O)=C(O)[C@H]2N(C)C)C(=O)C1=C(O)C=CC=C1[C@@]3(C)O

InChI Identifier

InChI=1S/C22H24N2O8/c1-21(31)8-5-4-6-11(25)12(8)16(26)13-9(21)7-10-15(24(2)3)17(27)14(20(23)30)19(29)22(10,32)18(13)28/h4-6,9-10,15,25,27-28,31-32H,7H2,1-3H3,(H2,23,30)/t9-,10-,15-,21+,22-/m0/s1

InChI Key

OFVLGDICTFRJMM-WESIUVDSSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as tetracyclines. These are polyketides having an octahydrotetracene-2-carboxamide skeleton, substituted with many hydroxy and other groups.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Tetracyclines

Sub Class

Not Available

Direct Parent

Tetracyclines

Alternative Parents

Substituents

Tetracycline
Naphthacene
Tetracene
Anthracene carboxylic acid or derivatives
Tetralin
Aryl ketone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Cyclohexenone
Aralkylamine
Benzenoid
Tertiary alcohol
Vinylogous acid
Tertiary aliphatic amine
Amino acid or derivatives
Tertiary amine
Carboxamide group
Primary carboxylic acid amide
Ketone
Polyol
Carboxylic acid derivative
Enol
Amine
Organic oxygen compound
Organopnictogen compound
Organonitrogen compound
Organooxygen compound
Alcohol
Carbonyl group
Organic nitrogen compound
Organic oxide
Hydrocarbon derivative
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

tetracyclines (CHEBI:27902 )
tetracyclines (C06570 )
Linear tetracyclines (C06570 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biofluid Locations

Not Available

Tissue Locations

Bone Marrow
Heart
Liver

Pathways

Name	SMPDB Link	KEGG Link
Tetracycline Action Pathway	SMP00294	Not Available

Applications

Biological Roles

Chemical Roles

protein synthesis inhibitor

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	172.5 dec°C
Boiling Point	Not Available
Solubility	231 mg/L (at 25°C)

Predicted Properties

Property	Value	Source
Water Solubility	1.33 g/L	ALOGPS
logP	-0.56	ALOGPS
logP	-3.5	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	2.92	ChemAxon
pKa (Strongest Basic)	8.19	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	181.62 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	114.19 m³·mol⁻¹	ChemAxon
Polarizability	42.9 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0bvi-5259500000-bd5eacef407c7cbcfc2a	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive	splash10-0002-5023749000-5781179b3d4ec0f18e56	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 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_3_5) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_6) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_7) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_4_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_4_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_4_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_4_8) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_4_9) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_4_10) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_5_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_5_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_5_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_5_8) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_3_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_3_5) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_3_6) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_3_7) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS ("Tetracycline,2TMS,#2" TMS) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-01sc-1900000000-7b792268aeb0a63c32c5	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-01p9-1900000000-da0b69e206bb0369723c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-000i-3900000000-299e4496b1f8e2f213cc	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-01ta-0000900000-e5ca6594fe72eb2bcd1f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-0ik9-0402900000-9ef4a0d08180ce9b2a1c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-0ik9-0402900000-a84ce5e2767545f4dd7e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-01sc-1900000000-7b792268aeb0a63c32c5	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 15V, Positive	splash10-01ta-0000900000-908fcaa876a610a2ecbe	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 45V, Negative	splash10-01p9-1900000000-da0b69e206bb0369723c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004j-0000900000-b0b8239482dc0ab660e1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01t9-0001900000-11d8380f89252d777068	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0btc-2268900000-9b20bc13399f86c0ff4a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0002900000-bbde63c16f1d6207b45a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0fal-0118900000-1d65f8ee8fa0af312c20	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00r6-9166000000-84828062c581777db668	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-002b-0000900000-3355d21a81297e70a696	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-0000900000-aec34c9f29d5643c9dd7	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-015i-9333100000-24fa0a1d06d44e57511d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-002f-0004900000-ce47e08c76771852979b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-05ec-0049700000-8b1cbde084e892a26b15	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-001u-1069300000-553a5cff4aef98461f76	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Bioavailability is less than 40% when administered via intramuscular injection, 100% intravenously, and 60-80% orally (fasting adults). Food and/or milk reduce GI absorption of oral preparations of tetracycline by 50% or more.

Mechanism of Toxicity

Tetracyclines target the 28S small subunit of the mitochondrial ribosome thereby deactivation mitochondrial protein synthesis. As a result tetracyclines are cytotoxic to the most metabolically active cells or tissues including the heart, liver, thymus and bone-marrow. (2). The likely target of most tetracyclines is the 12S rRNA molecule in the mitochondrial ribosome, which is analogous to the 16S rRNA in bacterial ribosomes.

Metabolism

Not metabolized Route of Elimination: They are concentrated by the liver in the bile and excreted in the urine and feces at high concentrations in a biologically active form. Half Life: 6-12 hours

Toxicity Values

LD50=808mg/kg (orally in mice)

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

Used to treat bacterial infections such as Rocky Mountain spotted fever, typhus fever, tick fevers, Q fever, rickettsialpox and Brill-Zinsser disease. May be used to treat infections caused by Chlamydiae spp., B. burgdorferi (Lyme disease), and upper respiratory infections caused by typical (S. pneumoniae, H. influenzae, and M. catarrhalis) and atypical organisms (C. pneumoniae, M. pneumoniae, L. pneumophila). May also be used to treat acne. Tetracycline may be an alternative drug for people who are allergic to penicillin.

Minimum Risk Level

Not Available

Health Effects

Side effects from normal doses of tetracyclines are relatively minimal, but of particular note is phototoxicity. Tetracylclines increase the risk of sunburn under exposure to light from the sun or other sources. Tetracyclines may also cause stomach or bowel upsets, and, on rare occasions, allergic reactions. Very rarely, severe headache and vision problems may be signs of dangerous secondary intracranial hypertension, also known as pseudotumor cerebri. Tetracyclines are teratogens and cause tooth discolouration and poor tooth mineralization in the fetus as they develop in infancy. Symptoms of tetracycline overdose include anorexia, nausea, diarrhea, glossitis, dysphagia, enterocolitis and inflammatory lesions, skin reactions such as maculopapular and erythematous rashes, exfoliative dermatitis, photosensitivity, hypersensitivity reactions such as urticaria, angioneurotic oedema, anaphylaxis, anaphyl-actoid purpura, pericarditis, and exacerbation of systemic lupus erythematosus, benign intracranial hypertension in adults disappearing on discontinuation of the medicine, haematologic abnormalities such as haemolytic anaemia, thrombocytopenia, neutropenia, and eosinophilia.

Symptoms

Not Available

Treatment

Drug therapy is discontinued immediately; exchange transfusion may be required to remove the drug. Sometimes, phenobarbital (UGT induction) is used.

Concentrations

Not Available

External Links

DrugBank ID

DB00759

HMDB ID

HMDB0014897

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

CPD0-1414

METLIN ID

Not Available

PDB ID

Wikipedia Link

Chemspider ID

ChEBI ID

PubChem Compound ID

Not Available

Kegg Compound ID

C06570

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Thomas F. McNamara, Nungavaram S. Ramamurthy, Lorne M. Golub, “Non-antibacterial tetracycline compositions possessing anti-collagenolytic properties and methods of preparing and using same.” U.S. Patent US4704383, issued May, 1963.

MSDS

Link

General References

1. https://www.ncbi.nlm.nih.gov/pubmed/?term=11061623

2. https://www.ncbi.nlm.nih.gov/pubmed/?term=11550419

3. https://www.ncbi.nlm.nih.gov/pubmed/?term=11744940

4. https://www.ncbi.nlm.nih.gov/pubmed/?term=12934399

5. https://www.ncbi.nlm.nih.gov/pubmed/?term=14585720

6. https://www.ncbi.nlm.nih.gov/pubmed/?term=15825421

7. https://www.ncbi.nlm.nih.gov/pubmed/?term=15913752

8. https://www.ncbi.nlm.nih.gov/pubmed/?term=16443056

9. https://www.ncbi.nlm.nih.gov/pubmed/?term=1650428