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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:50 UTC
Update Date2018-05-20 20:10:01 UTC
HMDB IDHMDB0014733
Secondary Accession Numbers
  • HMDB0030518
  • HMDB14733
  • HMDB30518
Metabolite Identification
Common NameOxytetracycline
DescriptionOxytetracycline is a tetracycline analog isolated from the actinomycete streptomyces rimosus and used in a wide variety of clinical conditions. [PubChem]Oxytetracycline inhibits cell growth by inhibiting translation. It binds to the 30S ribosomal subunit and prevents the amino-acyl tRNA from binding to the A site of the ribosome. The binding is reversible in nature. Oxytetracycline is lipophilic and can easily pass through the cell membrane or passively diffuses through porin channels in the bacterial membrane. Oxytetracycline is a clinically used broad-spectrum antibacterial antibiotic. It is approved by FDA for use in fish and animal feeds. Oxytetracycline is known as a broad-spectrum antibiotic due to its activity against such a wide range of infections. It was the second of the tetracyclines to be discovered. Oxytetracycline, like other tetracyclines, is used to treat many infections common and rare. Its better absorption profile makes it preferable to tetracycline for moderately severe acne, but alternatives sould be sought if no improvement occurs by 3 months
Structure
Thumb
Synonyms
ValueSource
2058-46-0 (mono-Hydrochloride)HMDB
5-Hydroxy-tetracyclineHMDB
5-HydroxytetracyclineHMDB
6153-64-6 (Di-hydrate)HMDB
6153-65-7 (Di-hydrochloride salt, di-hydrate)HMDB
7179-50-2 (Calcium (1:1) salt)HMDB
79-57-2 (ANHYDROUS)HMDB
AbbocinHMDB
AdamycinHMDB
Antibiotic TM 25HMDB
BerkmycenHMDB
BiostatHMDB
Biostat paHMDB
BisolvomycinHMDB
DabicyclineHMDB
DalimycinHMDB
FanterrinHMDB
GalsenomycinHMDB
GeomycinHMDB
GeotilinHMDB
HydroxytetracyclineHMDB
ImperacinHMDB
LenocyclineHMDB
LiquamycinHMDB
Liquamycin la 200HMDB
MacocynHMDB
MedamycinHMDB
Mycoshield TMQTHC 20HMDB
NSC 9169HMDB
NSC9169 (HCL)HMDB
OksisyklinHMDB
OssitetraciclinaHMDB
OTCHMDB
OxacyclineHMDB
OxitetraciclinaHMDB
OxitetracyclinHMDB
OxitetracyclinumHMDB
Oxy-kesso-tetraHMDB
OxydonHMDB
OxymycinHMDB
OxymykoinHMDB
OxypamHMDB
OxysteclinHMDB
OxyterracinHMDB
OxyterracineHMDB
OxyterracyneHMDB
OxytetracidHMDB
OxytetracyclinHMDB
Oxytetracycline (anhydrous)HMDB
Oxytetracycline amphotericHMDB
Oxytetracycline anhydrousHMDB
Oxytetracycline calciumHMDB
OxytetracyclinumHMDB
Pennox 200HMDB
ProteroxynaHMDB
RiomitsinHMDB
RyomycinHMDB
SolkaciclinaHMDB
StecsolinHMDB
StevacinHMDB
TarocynHMDB
TarosinHMDB
TeravitHMDB
TerrafungineHMDB
TerramitsinHMDB
TerramycinHMDB
TetranHMDB
UnimycinHMDB
UrsocyclinHMDB
UrsocyclineHMDB
VendarcinHMDB
Chemical FormulaC22H24N2O9
Average Molecular Weight460.434
Monoisotopic Molecular Weight460.148180376
IUPAC Name(4S,4aR,5S,5aR,6S,12aS)-4-(dimethylamino)-3,5,6,10,11,12a-hexahydroxy-6-methyl-1,12-dioxo-1,4,4a,5,5a,6,12,12a-octahydrotetracene-2-carboxamide
Traditional Name(4S,4aR,5S,5aR,6S,12aS)-4-(dimethylamino)-3,5,6,10,11,12a-hexahydroxy-6-methyl-1,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboxamide
CAS Registry Number79-57-2
SMILES
[H][C@@]12[C@@H](O)[C@@]3([H])C(=C(O)C4=C(O)C=CC=C4[C@@]3(C)O)C(=O)[C@]1(O)C(=O)C(C(N)=O)=C(O)[C@H]2N(C)C
InChI Identifier
InChI=1S/C22H24N2O9/c1-21(32)7-5-4-6-8(25)9(7)15(26)10-12(21)17(28)13-14(24(2)3)16(27)11(20(23)31)19(30)22(13,33)18(10)29/h4-6,12-14,17,25-28,32-33H,1-3H3,(H2,23,31)/t12-,13-,14+,17+,21-,22+/m1/s1
InChI KeyJLGOGFIHBRJQHY-PXOLEDIWSA-N
Chemical Taxonomy
DescriptionThis compound 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.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassTetracyclines
Sub ClassNot Available
Direct ParentTetracyclines
Alternative Parents
Substituents
  • Tetracycline
  • Anthracene carboxylic acid or derivatives
  • 1-naphthol
  • Naphthalene
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Cyclohexenone
  • Aralkylamine
  • Benzenoid
  • Cyclic alcohol
  • Tertiary alcohol
  • Vinylogous acid
  • Amino acid or derivatives
  • Tertiary amine
  • Tertiary aliphatic amine
  • Secondary alcohol
  • Primary carboxylic acid amide
  • Carboxamide group
  • Ketone
  • Polyol
  • Carboxylic acid derivative
  • Enol
  • Organooxygen compound
  • Amine
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organonitrogen compound
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point183 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1.4 g/LNot Available
LogP-1.3Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.87 g/LALOGPS
logP-0.94ALOGPS
logP-4.8ChemAxon
logS-2.7ALOGPS
pKa (Strongest Acidic)0.27ChemAxon
pKa (Strongest Basic)7.96ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area201.85 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity115.3 m³·mol⁻¹ChemAxon
Polarizability44.04 ųChemAxon
Number of Rings4ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-059w-9775700000-352b3c97029629bdf6deView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-03di-3063009000-aa89d9ddee9caea8ebdcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002f-0000900000-da39983197f199b0cc13View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004l-0000900000-f236df84f8ef8113e167View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-3239700000-c08203bbbefab1ff8d6aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0001900000-4037530eb747d1418771View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0295-0236900000-c490454f643a14ddc0e7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000f-8496000000-e06d26bc8c0a9a6c0d79View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00595 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00595 details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB002390
KNApSAcK IDNot Available
Chemspider ID10482174
KEGG Compound IDC06624
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkOxytetracycline
METLIN IDNot Available
PubChem Compound54715139
PDB IDOTC
ChEBI ID27701
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Solis Y, Chavarria G, Garcia F, Rodriguez C: Exposure of a Tropical Soil to MG/KG of Oxytetracycline Elicits Hormetic Responses in the Catabolic Activities of Its Microbial Community. Dose Response. 2011;9(3):434-41. doi: 10.2203/dose-response.10-045.Rodriguez. Epub 2011 Apr 30. [PubMed:22013404 ]
  2. Ci X, Chu X, Chen C, Li X, Yan S, Wang X, Yang Y, Deng X: Oxytetracycline attenuates allergic airway inflammation in mice via inhibition of the NF-kappaB pathway. J Clin Immunol. 2011 Apr;31(2):216-27. doi: 10.1007/s10875-010-9481-7. Epub 2010 Dec 7. [PubMed:21136283 ]
  3. Sundell K, Wiklund T: Effect of biofilm formation on antimicrobial tolerance of Flavobacterium psychrophilum. J Fish Dis. 2011 May;34(5):373-83. doi: 10.1111/j.1365-2761.2011.01250.x. Epub 2011 Mar 24. [PubMed:21488905 ]
  4. Le Breton MH, Savoy-Perroud MC, Diserens JM: Validation and comparison of the Copan Milk Test and Delvotest SP-NT for the detection of antimicrobials in milk. Anal Chim Acta. 2007 Mar 14;586(1-2):280-3. Epub 2006 Dec 2. [PubMed:17386724 ]
  5. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Transporters

General function:
Involved in transporter activity
Specific function:
Mediates saturable uptake of estrone sulfate, dehydroepiandrosterone sulfate and related compounds
Gene Name:
SLC22A11
Uniprot ID:
Q9NSA0
Molecular weight:
59970.9
References
  1. Babu E, Takeda M, Narikawa S, Kobayashi Y, Yamamoto T, Cha SH, Sekine T, Sakthisekaran D, Endou H: Human organic anion transporters mediate the transport of tetracycline. Jpn J Pharmacol. 2002 Jan;88(1):69-76. [PubMed:11855680 ]
General function:
Involved in ion transmembrane transporter activity
Specific function:
Involved in the renal elimination of endogenous and exogenous organic anions. Functions as organic anion exchanger when the uptake of one molecule of organic anion is coupled with an efflux of one molecule of endogenous dicarboxylic acid (glutarate, ketoglutarate, etc). Mediates the sodium-independent uptake of 2,3-dimercapto-1-propanesulfonic acid (DMPS). Mediates the sodium-independent uptake of p- aminohippurate (PAH), ochratoxin (OTA), acyclovir (ACV), 3'-azido- 3-'deoxythymidine (AZT), cimetidine (CMD), 2,4-dichloro- phenoxyacetate (2,4-D), hippurate (HA), indoleacetate (IA), indoxyl sulfate (IS) and 3-carboxy-4-methyl-5-propyl-2- furanpropionate (CMPF), cidofovir, adefovir, 9-(2- phosphonylmethoxyethyl) guanine (PMEG), 9-(2- phosphonylmethoxyethyl) diaminopurine (PMEDAP) and edaravone sulfate. PAH uptake is inhibited by p- chloromercuribenzenesulphonate (PCMBS), diethyl pyrocarbonate (DEPC), sulindac, diclofenac, carprofen, glutarate and okadaic acid. PAH uptake is inhibited by benzothiazolylcysteine (BTC), S-chlorotrifluoroethylcysteine (CTFC), cysteine S-conjugates S-dichlorovinylcysteine (DCVC), furosemide, steviol, phorbol 12-myristate 13-acetate (PMA), calcium ionophore A23187, benzylpenicillin, furosemide, indomethacin, bumetamide, losartan, probenecid, phenol red, urate, and alpha-ketoglutarate
Gene Name:
SLC22A6
Uniprot ID:
Q4U2R8
Molecular weight:
61815.8
References
  1. Babu E, Takeda M, Narikawa S, Kobayashi Y, Yamamoto T, Cha SH, Sekine T, Sakthisekaran D, Endou H: Human organic anion transporters mediate the transport of tetracycline. Jpn J Pharmacol. 2002 Jan;88(1):69-76. [PubMed:11855680 ]
General function:
Involved in transmembrane transport
Specific function:
Mediates sodium-independent multispecific organic anion transport. Transport of prostaglandin E2, prostaglandin F2, tetracycline, bumetanide, estrone sulfate, glutarate, dehydroepiandrosterone sulfate, allopurinol, 5-fluorouracil, paclitaxel, L-ascorbic acid, salicylate, ethotrexate, and alpha- ketoglutarate
Gene Name:
SLC22A7
Uniprot ID:
Q9Y694
Molecular weight:
60025.0
References
  1. Babu E, Takeda M, Narikawa S, Kobayashi Y, Yamamoto T, Cha SH, Sekine T, Sakthisekaran D, Endou H: Human organic anion transporters mediate the transport of tetracycline. Jpn J Pharmacol. 2002 Jan;88(1):69-76. [PubMed:11855680 ]