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Compound Detail

CHEMBL1200356

CYCLACILLIN
💊 Approved Drug
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💊 Approved Drug
CC1(C)S[C@@H]2[C@H](NC(=O)C3(N)CCCCC3)C(=O)N2[C@H]1C(=O)O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1200356
Name CYCLACILLIN
Phase Approved
Structure Type MOL
InChI Key HGBLNBBNRORJKI-WCABBAIRSA-N
Therapeutic ✓ Yes

Known Names

Calthor Ciclacilina Ciclacillin Ciclacilline Cyclacillin Cyclapen-w NSC-88789 Vastcillin Vasticillin WY-4508
2
Targets
12
Activities
2
Assay Types
0
PK Parameters
20
Publications
10
Known Names
1
Mechanisms

Molecular Properties

341.4
MW (Da)
0.28
ALogP
5
HBA
3
HBD
112.7
PSA (Ų)
0.64
QED
0
Ro5 Violations
3
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1979
Availability Discontinued
Chirality Single Enantiomer

Routes of Administration

Oral

Flags

Natural Product
USAN Stem -cillin
USAN Year 1969

Extended Properties

Molecular Formula C15H23N3O4S
MW 341.43
Aromatic Rings 0
Heavy Atoms 23
NP-Likeness 0.84

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Bacterial penicillin-binding protein inhibitor INHIBITOR Bacterial penicillin-binding protein ✓ ✓

Activity Summary

Ki 9 meas. best 4.57
IC50 3 meas.

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Solute carrier family 15 member 2
CHEMBL3325
 Ki 4.57 4.465 27000.0 2
Solute carrier family 15 member 2
CHEMBL1743125
 Ki 4.43 4.39 36800.0 4

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Solute carrier family 15 member 2 Ki = 27000.0 nM 4.57 TP_TRANSPORTER: inhibition of Gly-Sar uptake in PEPT2-expressing LLC-PK1 cells 9374833
Solute carrier family 15 member 2 Ki = 36800.0 nM 4.43 TP_TRANSPORTER: inhibition of Chephalexin uptake in SKPT cells 7592745
Solute carrier family 15 member 2 Ki = 39100.0 nM 4.41 TP_TRANSPORTER: inhibition of Gly-Sar uptake in SKPT cells 7592745
Solute carrier family 15 member 2 Ki = 44000.0 nM 4.36 Binding affinity to human PepT2 in SKTP cells 21741846
Solute carrier family 15 member 2 Ki = 43651.58 nM 4.36 Binding affinity to human PepT2 in SKTP cells 21741846
Solute carrier family 15 member 2 Ki = 44000.0 nM 4.36 TP_TRANSPORTER: inhibition of Gly-Sar uptake (pH6.0) in SKPT cells 15567297

Literature References

PubMed DOI Target Context # Activities
16472241 10.2174/1570163043334794 Hepatotoxicity 18
37468498 10.1038/s41467-023-40064-9 Alpha-1A adrenergic receptor 3
7592745 10.1074/jbc.270.43.25672 Solute carrier family 15 member 2 3
37468498 10.1038/s41467-023-40064-9 Gamma-aminobutyric acid receptor subunit alpha-1 2
37468498 10.1038/s41467-023-40064-9 Cannabinoid receptor 1 2
37468498 10.1038/s41467-023-40064-9 Beta-2 adrenergic receptor 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 Progesterone receptor 2
- 10.6019/CHEMBL4651402 SARS-CoV-2 2
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 1A 2
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 2B 2
37468498 10.1038/s41467-023-40064-9 Alpha-2A adrenergic receptor 2
7592745 10.1074/jbc.270.43.25672 Solute carrier family 15 member 1 2
21741846 10.1016/j.bmc.2011.06.027 Solute carrier family 15 member 2 2
24249037 10.1007/s11095-013-1232-z No relevant target 1
- 10.1101/2020.04.03.023846 SARS-CoV-2 1
37468498 10.1038/s41467-023-40064-9 Voltage-gated inwardly rectifying potassium channel KCNH2 1
9374833 10.1152/ajprenal.1997.273.5.f706 Solute carrier family 15 member 2 1
10636865 10.1074/jbc.275.3.1699 Organic cation/carnitine transporter 2 1

Data from ChEMBL 36 via Core Engine