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Compound Detail

CHEMBL1434

MINOCYCLINE
💊 Approved Drug
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💊 Approved Drug
CN(C)c1ccc(O)c2c1C[C@H]1C[C@H]3[C@H](N(C)C)C(O)=C(C(N)=O)C(=O)[C@@]3(O)C(O)=C1C2=O

Basic Information

ChEMBL ID CHEMBL1434
Name MINOCYCLINE
Phase Approved
Structure Type MOL
InChI Key DYKFCLLONBREIL-KVUCHLLUSA-N
Therapeutic ✓ Yes

Known Names

Minociclina Minocycline
16
Targets
49
Activities
4
Assay Types
11
PK Parameters
20
Publications
2
Known Names
20
Indications

Molecular Properties

457.5
MW (Da)
0.19
ALogP
9
HBA
5
HBD
164.6
PSA (Ų)
0.40
QED
0
Ro5 Violations
3
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1971
Availability Prescription
Chirality Single Enantiomer

Routes of Administration

Oral Parenteral Topical

Flags

Natural Product
USAN Stem -cycline
USAN Year 1966

Extended Properties

Molecular Formula C23H27N3O7
MW 457.48
Aromatic Rings 1
Heavy Atoms 33
NP-Likeness 1.30

Indications

Acne Vulgaris Bacterial Infections Infections Amyotrophic Lateral Sclerosis Arthritis, Rheumatoid Bipolar Disorder Depressive Disorder Depressive Disorder, Treatment-Resistant Heroin Dependence Hypertension Idiopathic Pulmonary Fibrosis Lichen Planus, Oral Multiple Sclerosis Neurobehavioral Manifestations Peri-Implantitis Periodontitis Pneumothorax Psychotic Disorders Psychotic Disorders Rosacea

ATC Classification

A01AB23
minocycline
Level 1: ALIMENTARY TRACT AND METABOLISM
Level 2: STOMATOLOGICAL PREPARATIONS
D10AF07
minocycline
Level 1: DERMATOLOGICALS
Level 2: ANTI-ACNE PREPARATIONS
J01AA08
minocycline
Level 1: ANTIINFECTIVES FOR SYSTEMIC USE
Level 2: ANTIBACTERIALS FOR SYSTEMIC USE

Activity Summary

IC50 37 meas. best 5.58
Kd 6 meas. best 6.22
EC50 4 meas. best 6.46
Ki 2 meas.

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Staphylococcus aureus
CHEMBL352
EC50 6.46 6.46 350.0 1
Unchecked
CHEMBL612545
Kd 6.22 6.032 597.0 5
Klebsiella pneumoniae subsp. pneumoniae
CHEMBL613207
EC50 6.16 6.16 700.0 1
Enterobacter cloacae
CHEMBL349
EC50 5.82 5.82 1500.0 1
Pseudomonas aeruginosa
CHEMBL348
EC50 5.62 5.62 2400.0 1
Multidrug transporter MdfA
CHEMBL4785
IC50 5.58 5.58 2600.0 1
Plasmodium falciparum
CHEMBL364
IC50 5.52 5.485 3000.0 2
BV-2
CHEMBL614781
IC50 5.31 4.8629 4900.0 7
Mycolicibacterium smegmatis
CHEMBL613088
IC50 5.3 5.2033 5020.0 6
NON-PROTEIN TARGET
CHEMBL3879801
IC50 5.03 4.5425 9420.0 4
Albumin
CHEMBL3253
Kd 4.92 4.92 12000.0 1
N9
CHEMBL613516
IC50 4.7 4.7 19890.0 1
Trypanosoma cruzi
CHEMBL368
IC50 4.65 4.65 22300.0 1
RAW264.7
CHEMBL612557
IC50 4.5 4.4733 31280.0 3
Trypanosoma brucei rhodesiense
CHEMBL612348
IC50 4.44 4.44 36550.0 1
Leishmania donovani
CHEMBL367
IC50 4.34 4.34 45680.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 1.1 mL.min-1.kg-1 Homo sapiens
CL 1.2 mL.min-1.kg-1 Homo sapiens
CL 1.2 mL.min-1.kg-1 Homo sapiens
Cmax 1311.53 nM Homo sapiens
F 97.5 % Homo sapiens
F 100.0 % Homo sapiens
MRT 22.0 hr Homo sapiens
T1/2 17.0 hr Homo sapiens
T1/2 12.0 hr Homo sapiens
T1/2 12.0 hr Homo sapiens
Tmax 2.3 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Staphylococcus aureus EC50 = 350.0 nM 6.46 Antibacterial activity against methicillin resistant Staphylococcus aureus subsp... 27184767
Unchecked Kd = 597.0 nM 6.22 Binding affinity to 5'-FAM-pre-miR-373 (unknown origin) after 4 hrs by fluoresce... 26264847
Unchecked Kd = 612.0 nM 6.21 Binding affinity to 5'-FAM-pre-miR-372 (unknown origin) after 4 hrs by fluoresce... 26264847
Unchecked Kd = 651.0 nM 6.19 Binding affinity to 5'-FAM-pre-miR-17 (unknown origin) after 4 hrs by fluorescen... 26264847
Klebsiella pneumoniae subsp. pneumoniae EC50 = 700.0 nM 6.16 Antibacterial activity against multidrug resistant Klebsiella pneumoniae subsp. ... 27184767
Unchecked Kd = 1450.0 nM 5.84 Binding affinity to 5'-FAM-pre-miR-372 (unknown origin) after 4 hrs by fluoresce... 26264847
Enterobacter cloacae EC50 = 1500.0 nM 5.82 Antibacterial activity against multidrug resistant Enterobacter cloacae subsp. c... 27184767
Unchecked Kd = 1980.0 nM 5.7 Binding affinity to 5'-FAM-pre-miR-372 (unknown origin) after 4 hrs by fluoresce... 26264847
Pseudomonas aeruginosa EC50 = 2400.0 nM 5.62 Antibacterial activity against multidrug resistant Pseudomonas aeruginosa NCTC 1... 27184767
Multidrug transporter MdfA IC50 = 2600.0 nM 5.58 Inhibition of [3H]tetracycline uptake into everted membrane vesicles, prepared f... 8426364
Plasmodium falciparum IC50 = 3000.0 nM 5.52 Antimicrobial activity against Plasmodium falciparum 20185316
Plasmodium falciparum IC50 = 3580.0 nM 5.45 DNDI: Malaria in Vitro, 72 hour -
BV-2 IC50 = 4900.0 nM 5.31 Antineuroinflammatory activity in mouse BV2 cells assessed as inhibition of LPS-... 30350995
Mycolicibacterium smegmatis IC50 = 5020.0 nM 5.3 Antimycobacterial activity against Mycobacterium smegmatis grown in carbon-limit... 19786608
Mycolicibacterium smegmatis IC50 = 5020.0 nM 5.3 Antimycobacterial activity against Mycobacterium smegmatis grown in carbon-limit... 19786608
Mycolicibacterium smegmatis IC50 = 6770.0 nM 5.17 Antimycobacterial activity against Mycobacterium smegmatis grown in Luria-Bertan... 19786608
Mycolicibacterium smegmatis IC50 = 6770.0 nM 5.17 Antimycobacterial activity against Mycobacterium smegmatis grown in Luria-Bertan... 19786608
Mycolicibacterium smegmatis IC50 = 7230.0 nM 5.14 Antimycobacterial activity against Mycobacterium smegmatis grown in nitrogen -li... 19786608
Mycolicibacterium smegmatis IC50 = 7230.0 nM 5.14 Antimycobacterial activity against Mycobacterium smegmatis grown in nitrogen -li... 19786608
BV-2 IC50 = 9070.0 nM 5.04 Antineuroinflammatory activity in mouse BV2 cells assessed as inhibition of LPS-... 28911817

Literature References

PubMed DOI Target Context # Activities
17620376 10.1128/aac.00625-07 Escherichia coli 48
19188385 10.1128/aac.01619-08 Staphylococcus aureus 37
19738019 10.1128/aac.00724-09 NON-PROTEIN TARGET 28
20211899 10.1128/aac.01420-09 Escherichia coli 28
17846127 10.1128/aac.01259-06 Acinetobacter baumannii 26
18519719 10.1128/aac.00922-07 Staphylococcus aureus 23
26264847 10.1016/j.bmc.2015.07.062 Unchecked 21
16472241 10.2174/1570163043334794 Hepatotoxicity 18
19015360 10.1128/aac.00883-08 Klebsiella pneumoniae 18
19015360 10.1128/aac.00883-08 Escherichia coli 17
19738027 10.1128/aac.00845-09 Staphylococcus aureus 16
19075049 10.1128/aac.01097-08 Acinetobacter baumannii 15
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
19188385 10.1128/aac.01619-08 Staphylococcus epidermidis 13
- 10.1039/C5MD00377F Acinetobacter baumannii 12
19786608 10.1128/aac.00803-09 Mycolicibacterium smegmatis 12
28409644 10.1021/acs.jmedchem.6b01742 Pseudomonas aeruginosa 12
17420217 10.1128/aac.01198-06 Acinetobacter baumannii 12
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
20038618 10.1128/aac.00899-09 NON-PROTEIN TARGET 11

Data from ChEMBL 36 via Core Engine