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Compound Detail

CHEMBL1025

ISOFLUROPHATE
💊 Approved Drug
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💊 Approved Drug
CC(C)OP(=O)(F)OC(C)C
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1025
Name ISOFLUROPHATE
Phase Approved
Structure Type MOL
InChI Key MUCZHBLJLSDCSD-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

Floropryl Fluostigmine Isoflurophate NSC-727370
6
Targets
10
Activities
3
Assay Types
0
PK Parameters
20
Publications
4
Known Names
1
Indications
1
Mechanisms

Molecular Properties

184.2
MW (Da)
2.91
ALogP
3
HBA
0
HBD
35.5
PSA (Ų)
0.63
QED
0
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1957
Availability Discontinued
Chirality Achiral

Routes of Administration

Topical

Extended Properties

Molecular Formula C6H14FO3P
MW 184.15
Aromatic Rings 0
Heavy Atoms 11
NP-Likeness -0.31

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Acetylcholinesterase inhibitor INHIBITOR Acetylcholinesterase ✓ ✓

Indications

Glaucoma

ATC Classification

S01EB07
fluostigmine
Level 1: SENSORY ORGANS
Level 2: OPHTHALMOLOGICALS

Activity Summary

IC50 6 meas. best 7.3
Kd 2 meas. best 4.89
Ki 2 meas. best 5.22

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Liver carboxylesterase
CHEMBL3383
 IC50 7.3 7.3 50.0 1
Acetylcholinesterase
CHEMBL220
 IC50 6.92 6.92 120.0 1
Acetylcholinesterase
CHEMBL4078
 IC50 6.32 6.32 480.0 1
Unchecked
CHEMBL612545
 IC50 5.3 5.0 5000.0 2
Acetylcholinesterase
CHEMBL220
 Ki 5.22 5.22 6000.0 1
Lysosomal protective protein
CHEMBL6115
 IC50 5.0 5.0 10000.0 1
Acetylcholinesterase
CHEMBL220
 Kd 4.89 4.89 13000.0 1
Acetylcholinesterase
CHEMBL4780
 Kd 4.16 4.16 70000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Liver carboxylesterase IC50 = 50.0 nM 7.3 Inhibition of porcine liver carboxylesterase using [14C]GS-7340 substrate 17145787
Acetylcholinesterase IC50 = 120.0 nM 6.92 Inhibition of human AChE by modified Ellman's spectrophotometric method 20189400
Acetylcholinesterase IC50 = 480.0 nM 6.32 In vitro inhibitory activity against acetylcholinesterase from electric eel 3193422
Unchecked IC50 = 5000.0 nM 5.3 Inhibition of purified prodrug hydrolase using [14C]GS-7340 substrate 17145787
Acetylcholinesterase Ki = 6000.0 nM 5.22 Inhibition of human AChE assessed as equilibrium binding by modified Ellman's sp... 20189400
Lysosomal protective protein IC50 = 10000.0 nM 5.0 Inhibition of recombinant CatA using [14C]GS-7340 substrate 17145787
Acetylcholinesterase Kd = 13000.0 nM 4.89 Binding affinity to human AChE 18479118
Unchecked IC50 = 20000.0 nM 4.7 Inhibition of crude human PBMC extract prodrug hydrolase using [14C]GS-7340 subs... 17145787
Acetylcholinesterase Kd = 70000.0 nM 4.16 Inhibition of Torpedo californica AChE 18479118

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885881 Rattus norvegicus 405
18479118 10.1021/jm701253t Acetylcholinesterase 3
3193422 10.1021/jm00120a008 Acetylcholinesterase 2
37468498 10.1038/s41467-023-40064-9 Thromboxane A2 receptor 2
37468498 10.1038/s41467-023-40064-9 Prostaglandin G/H synthase 1 2
37468498 10.1038/s41467-023-40064-9 Alpha-1A adrenergic receptor 2
37978953 10.1021/acs.jmedchem.3c01328 Pseudomonas aeruginosa 2
37468498 10.1038/s41467-023-40064-9 Muscarinic acetylcholine receptor M1 2
20189400 10.1016/j.bmc.2010.01.063 Acetylcholinesterase 2
17145787 10.1128/aac.00968-06 Unchecked 2
17664327 10.1128/aac.00671-07 Unchecked 1
36760737 10.1039/d2md00212d ATP-dependent Clp protease proteolytic subunit 1
37468498 10.1038/s41467-023-40064-9 D(1A) dopamine receptor 1
37468498 10.1038/s41467-023-40064-9 Sodium-dependent dopamine transporter 1
37468498 10.1038/s41467-023-40064-9 Estrogen receptor 1
37468498 10.1038/s41467-023-40064-9 Acetylcholinesterase 1
17145787 10.1128/aac.00968-06 Liver carboxylesterase 1
17145787 10.1128/aac.00968-06 Lysosomal protective protein 1
37468498 10.1038/s41467-023-40064-9 Alpha-2A adrenergic receptor 1
37468498 10.1038/s41467-023-40064-9 Mu-type opioid receptor 1

Data from ChEMBL 36 via Core Engine