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Compound Detail

CHEMBL771

CYCLOSERINE
💊 Approved Drug
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💊 Approved Drug
N[C@@H]1CONC1=O

Basic Information

ChEMBL ID CHEMBL771
Name CYCLOSERINE
Phase Approved
Structure Type MOL
InChI Key DYDCUQKUCUHJBH-UWTATZPHSA-N
Therapeutic ✓ Yes

Known Names

Cicloserina Cycloserine Cycloserinum D-cycloserine NSC-154851 NSC-76029 Orientomycin Seromycin
5
Targets
24
Activities
3
Assay Types
0
PK Parameters
20
Publications
8
Known Names
20
Indications
2
Mechanisms

Molecular Properties

102.1
MW (Da)
-1.62
ALogP
3
HBA
2
HBD
64.3
PSA (Ų)
0.39
QED
0
Ro5 Violations
0
Rot. Bonds

Drug Information

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

Routes of Administration

Oral

Flags

Natural Product

Extended Properties

Molecular Formula C3H6N2O2
MW 102.09
Aromatic Rings 0
Heavy Atoms 7
NP-Likeness 1.90

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
D-alanylalanine synthetase inhibitor INHIBITOR D-alanine--D-alanine ligase
Alanine racemase inhibitor INHIBITOR Alanine racemase

Indications

Tuberculosis Tuberculosis Asperger Syndrome Autistic Disorder Obsessive-Compulsive Disorder Pain Panic Disorder Phobia, Social Phobic Disorders Schizophrenia Smoking Cessation Stress Disorders, Post-Traumatic Tuberculosis, Pulmonary Agoraphobia Alcohol Drinking Bipolar Disorder Brain Injuries Cocaine-Related Disorders Depressive Disorder, Major Fibromyalgia

ATC Classification

J04AB01
cycloserine
Level 1: ANTIINFECTIVES FOR SYSTEMIC USE
Level 2: ANTIMYCOBACTERIALS

Activity Summary

IC50 13 meas. best 5.64
EC50 6 meas. best 5.53
Ki 5 meas. best 4.66

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Glutamate NMDA receptor
CHEMBL1907608
IC50 5.64 5.64 2300.0 1
Glutamate NMDA receptor
CHEMBL1907608
EC50 5.53 5.53 2950.0 1
Unchecked
CHEMBL612545
EC50 5.2 5.2 6309.6 1
Glutamate receptor ionotropic, NMDA 1
CHEMBL330
IC50 5.13 5.13 7370.0 1
Mycobacterium tuberculosis
CHEMBL360
EC50 4.9 4.7133 12470.0 3
Mycobacterium tuberculosis
CHEMBL360
IC50 4.9 4.8267 12470.0 6
Glutamate receptor ionotropic, NMDA 2C
CHEMBL401
EC50 4.74 4.74 18100.0 1
Unchecked
CHEMBL612545
Ki 4.66 4.61 22000.0 3
Unchecked
CHEMBL612545
IC50 4.0 4.0 100000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Glutamate NMDA receptor IC50 = 2300.0 nM 5.64 In vitro inhibition of [3H]glycine at NMDA receptor 7990104
Glutamate NMDA receptor EC50 = 2950.0 nM 5.53 In vitro concentration eliciting half-maximal effect on [3H]-MK 801 radioligand ... 10360746
Unchecked EC50 = 6309.57 nM 5.2 Partial agonist activity at glycine site of NMDA receptor in rat brain cortex me... 19642674
Glutamate receptor ionotropic, NMDA 1 IC50 = 7370.0 nM 5.13 In vitro inhibitory activity to inhibit [3H]glycine binding to NMDA receptor 10360746
Mycobacterium tuberculosis IC50 = 12470.0 nM 4.9 Antimycobacterial activity against Mycobacterium tuberculosis H37Rv assessed as ... 25129868
Mycobacterium tuberculosis IC50 = 12470.0 nM 4.9 Antimycobacterial activity against Mycobacterium tuberculosis H37Rv assessed as ... 27687968
Mycobacterium tuberculosis IC50 = 12470.0 nM 4.9 Antimicrobial activity against Mycobacterium tuberculosis H37Rv by Alamar blue a... 28552337
Mycobacterium tuberculosis IC50 = 12470.0 nM 4.9 Antimicrobial activity against Mycobacterium tuberculosis H37Rv after 7 days by ... 24412719
Mycobacterium tuberculosis EC50 = 12470.0 nM 4.9 Antimycobacterial activity against Mycobacterium tuberculosis H37Rv assessed as ... 24472146
Glutamate receptor ionotropic, NMDA 2C EC50 = 18100.0 nM 4.74 Compound was evaluated for in vitro inhibition of [3H]TCP at NMDA receptor. 7990104
Mycobacterium tuberculosis IC50 = 20800.0 nM 4.68 Antimicrobial activity against Mycobacterium tuberculosis H37Rv ATCC 27294 incub... 27025343
Mycobacterium tuberculosis IC50 = 20800.0 nM 4.68 Antimycobacterial activity against Mycobacterium tuberculosis H37Rv 29202408
Unchecked Ki = 22000.0 nM 4.66 Inhibition of Escherichia coli DdlB 19053785
Mycobacterium tuberculosis EC50 = 23550.0 nM 4.63 Antitubercular activity against Mycobacterium tuberculosis H37Rv by BacTiter-Gl ... 23352268
Mycobacterium tuberculosis EC50 = 24760.0 nM 4.61 Antitubercular activity against Mycobacterium tuberculosis H37Rv by microdilutio... 23352268
Unchecked Ki = 25000.0 nM 4.6 Inhibition of full-length 6His-tagged Mycobacterium tuberculosis H37Rv Ddl expre... 30300845
Unchecked Ki = 27000.0 nM 4.57 Inhibition of D-alanine binding site of Escherichia coli D-alanine-D-alanine lig... 18321716
Unchecked IC50 = 100000.0 nM 4.0 Inhibition of C-terminal hexahistidine-tagged recombinant Staphylococcus aureus ... 37948922

Literature References

PubMed DOI Target Context # Activities
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
3137344 10.1021/jm00117a017 UDP-N-acetylmuramoyl-tripeptide--D-alanyl-D-alanine ligase 12
17908943 10.1128/aac.00845-07 Escherichia coli 12
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
22178557 10.1016/j.bmcl.2011.11.114 Mycobacterium tuberculosis 10
19546371 10.1128/aac.00200-09 Staphylococcus aureus 10
20718497 10.1021/jm100568q Mycobacterium tuberculosis 9
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
19470511 10.1128/aac.00166-09 Escherichia coli 8
19470511 10.1128/aac.00166-09 Unchecked 8
24268596 10.1016/j.ejmech.2013.09.061 Mycobacterium tuberculosis 7
22664188 10.1016/j.bmc.2012.05.004 Mycobacterium tuberculosis 7
34265421 10.1016/j.bmcl.2021.128261 Mycobacterium tuberculosis 6
32631549 10.1016/j.bmcl.2020.127351 Mycobacterium tuberculosis 6
18541730 10.1128/aac.00273-08 Staphylococcus aureus 6
23352268 10.1016/j.bmcl.2012.12.069 Mycobacterium tuberculosis 6
24087924 10.1021/np400497f Mycobacterium tuberculosis 6
20713679 10.1128/aac.00661-10 Mycobacterium tuberculosis 6
30803803 10.1016/j.bmcl.2019.02.019 Mycobacterium tuberculosis 6
19470511 10.1128/aac.00166-09 Staphylococcus aureus 5

Data from ChEMBL 36 via Core Engine