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Compound Detail

CHEMBL1591

DEMECLOCYCLINE
💊 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)ccc(Cl)c4[C@@H](O)[C@H]3C[C@@H]12

Basic Information

ChEMBL ID CHEMBL1591
Name DEMECLOCYCLINE
Phase Approved
Structure Type MOL
InChI Key FMTDIUIBLCQGJB-SEYHBJAFSA-N
Therapeutic ✓ Yes

Known Names

Demeclociclina Demeclocycline Demethylchlortetracycline
2
Targets
7
Activities
1
Assay Types
5
PK Parameters
20
Publications
3
Known Names
2
Indications

Molecular Properties

464.9
MW (Da)
0.26
ALogP
9
HBA
6
HBD
181.6
PSA (Ų)
0.33
QED
1
Ro5 Violations
2
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1960
Availability Prescription
Chirality Single Enantiomer

Routes of Administration

Oral

Flags

Natural Product
USAN Stem -cycline

Extended Properties

Molecular Formula C21H21ClN2O8
MW 464.86
Aromatic Rings 1
Heavy Atoms 32
NP-Likeness 1.56

Indications

Bacterial Infections Osteomyelitis

ATC Classification

D06AA01
demeclocycline
Level 1: DERMATOLOGICALS
Level 2: ANTIBIOTICS AND CHEMOTHERAPEUTICS FOR DERMATOLOGICAL USE
J01AA01
demeclocycline
Level 1: ANTIINFECTIVES FOR SYSTEMIC USE
Level 2: ANTIBACTERIALS FOR SYSTEMIC USE

Activity Summary

IC50 7 meas. best 5.86

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Alpha-ketoglutarate-dependent dioxygenase FTO
CHEMBL2331065
IC50 5.86 5.86 1390.0 1
Mycolicibacterium smegmatis
CHEMBL613088
IC50 5.73 5.44 1880.0 6

Pharmacokinetic Data

Parameter Value Units Species
CL 1.1 mL.min-1.kg-1 Homo sapiens
F 66.0 % Homo sapiens
Fu 0.59 - Homo sapiens
MRT 17.0 hr Homo sapiens
T1/2 12.0 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Literature References

PubMed DOI Target Context # Activities
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
19786608 10.1128/aac.00803-09 Mycolicibacterium smegmatis 12
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
18426954 10.1124/dmd.108.020479 ADMET 4
37468498 10.1038/s41467-023-40064-9 Alpha-2A adrenergic receptor 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
- 10.6019/CHEMBL4651402 SARS-CoV-2 2
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 1A 2
26948801 10.1016/j.drudis.2016.02.015 Homo sapiens 2
37468498 10.1038/s41467-023-40064-9 Progesterone receptor 2
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 2B 2
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 2A 2
37468498 10.1038/s41467-023-40064-9 Muscarinic acetylcholine receptor M2 2
37468498 10.1038/s41467-023-40064-9 Gamma-aminobutyric acid receptor subunit alpha-1 2
24224794 10.1021/np400145u Acinetobacter baumannii 1
38318365 10.1016/j.isci.2024.108907 Deoxynucleoside triphosphate triphosphohydrolase SAMHD1 1
17428028 10.1021/ci6004542 Phospholipidosis 1
18426954 10.1124/dmd.108.020479 NON-PROTEIN TARGET 1
19947605 10.1021/jm901421c ADMET 1

Data from ChEMBL 36 via Core Engine