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Compound Detail

CHEMBL1517

OXYTETRACYCLINE
💊 Approved Drug
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💊 Approved Drug
CN(C)[C@@H]1C(O)=C(C(N)=O)C(=O)[C@@]2(O)C(O)=C3C(=O)c4c(O)cccc4[C@@](C)(O)[C@H]3[C@H](O)[C@@H]12

Basic Information

ChEMBL ID CHEMBL1517
Name OXYTETRACYCLINE
Phase Approved
Structure Type MOL
InChI Key IWVCMVBTMGNXQD-PXOLEDIWSA-N
Therapeutic ✓ Yes

Known Names

5-hydroxytetracycline dihydrate Berkmycen Chemocycline E703 Galenomycin Hi-tet Imperacin Microtet Nitox NSC-757262 NSC-9169 Oxitetraciclina +12 more
2
Targets
12
Activities
2
Assay Types
6
PK Parameters
20
Publications
24
Known Names
5
Indications
1
Mechanisms

Molecular Properties

460.4
MW (Da)
-1.24
ALogP
10
HBA
7
HBD
201.8
PSA (Ų)
0.26
QED
1
Ro5 Violations
2
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1964
Availability Discontinued
Chirality Single Enantiomer

Routes of Administration

Oral Parenteral Topical

Flags

Natural Product
USAN Stem -cycline

Extended Properties

Molecular Formula C22H24N2O9
MW 460.44
Aromatic Rings 1
Heavy Atoms 33
NP-Likeness 1.83

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Bacterial 70S ribosome inhibitor INHIBITOR Bacterial 70S ribosome

Indications

Bacterial Infections Eye Infections Infections Acne Vulgaris Osteomyelitis

ATC Classification

A01AB25
oxytetracycline
Level 1: ALIMENTARY TRACT AND METABOLISM
Level 2: STOMATOLOGICAL PREPARATIONS
D06AA03
oxytetracycline
Level 1: DERMATOLOGICALS
Level 2: ANTIBIOTICS AND CHEMOTHERAPEUTICS FOR DERMATOLOGICAL USE
G01AA07
oxytetracycline
Level 1: GENITO URINARY SYSTEM AND SEX HORMONES
Level 2: GYNECOLOGICAL ANTIINFECTIVES AND ANTISEPTICS
J01AA06
oxytetracycline
Level 1: ANTIINFECTIVES FOR SYSTEMIC USE
Level 2: ANTIBACTERIALS FOR SYSTEMIC USE
J01AA56
oxytetracycline, combinations
Level 1: ANTIINFECTIVES FOR SYSTEMIC USE
Level 2: ANTIBACTERIALS FOR SYSTEMIC USE
S01AA04
oxytetracycline
Level 1: SENSORY ORGANS
Level 2: OPHTHALMOLOGICALS

Activity Summary

IC50 7 meas. best 4.47
Kd 5 meas. best 5.28

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Unchecked
CHEMBL612545
Kd 5.28 5.158 5200.0 5
Plasmodium falciparum
CHEMBL364
IC50 4.47 4.47 34000.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 2.0 mL.min-1.kg-1 Homo sapiens
CL 2.0 mL.min-1.kg-1 Homo sapiens
F 58.0 % Homo sapiens
Fu 0.9 - Homo sapiens
MRT 12.0 hr Homo sapiens
T1/2 10.0 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885881 Rattus norvegicus 270
26264847 10.1016/j.bmc.2015.07.062 Unchecked 16
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
- 10.1007/s00044-007-9020-0 Superoxide dismutase [Cu-Zn] 11
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
17638695 10.1128/aac.00420-07 Mycoplasma putrefaciens 5
- 10.1584/jpestics.28.183 Streptomyces scabiei 4
18426954 10.1124/dmd.108.020479 ADMET 4
- 10.1584/jpestics.28.183 Streptomyces acidiscabies 4
20855745 10.1128/aac.00580-10 Escherichia coli 3
20014752 10.1021/tx900326k Hepatotoxicity 3
- 10.1584/jpestics.28.183 Streptomyces alboniger 3
- 10.6019/CHEMBL4651402 SARS-CoV-2 2
19445515 10.1021/jm900403j Homo sapiens 2
31098005 10.1021/acsmedchemlett.9b00091 microRNA 21 2
26948801 10.1016/j.drudis.2016.02.015 Homo sapiens 2
21112128 10.1016/j.ejmech.2010.11.005 ADMET 1
21624500 10.1016/j.drudis.2011.05.007 Hepatotoxicity 1
37651876 10.1016/j.ejmech.2023.115732 NEDD8/NEDD8-conjugating enzyme Ubc12 1

Data from ChEMBL 36 via Core Engine