Compound Detail
CHEMBL1756
ESTRAMUSTINE PHOSPHATE 💊 Approved Drug
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💊 Approved Drug
C[C@]12CC[C@@H]3c4ccc(OC(=O)N(CCCl)CCCl)cc4CC[C@H]3[C@@H]1CC[C@@H]2OP(=O)(O)O
Basic Information
| ChEMBL ID | CHEMBL1756 |
| Name | ESTRAMUSTINE PHOSPHATE |
| Phase | Approved |
| Structure Type | MOL |
| InChI Key | ADFOJJHRTBFFOF-RBRWEJTLSA-N |
| Therapeutic | ✓ Yes |
| Active Moiety | CHEMBL1575 |
4
Targets
8
Activities
2
Assay Types
5
PK Parameters
20
Publications
6
Known Names
1
Indications
Molecular Properties
520.4
MW (Da)
5.30
ALogP
4
HBA
2
HBD
96.3
PSA (Ų)
0.37
QED
2
Ro5 Violations
7
Rot. Bonds
Drug Information
| Molecule Type | Small molecule |
| First Approval | 1981 |
| Availability | Discontinued |
| Chirality | Single Enantiomer |
Indications
Prostatic Neoplasms, Castration-Resistant
Activity Summary
IC50 7 meas. best 4.77
Kd 1 meas. best 5.08
Target Activity Profile
| Target | Type | Best pChEMBL | Mean pChEMBL | Best (nM) | # Data |
|---|---|---|---|---|---|
| Tyrosine-protein phosphatase non-receptor type 11 CHEMBL3864 | Kd | 5.08 | 5.08 | 8400.0 | 1 |
| Tyrosine-protein phosphatase non-receptor type 11 CHEMBL3864 | IC50 | 4.77 | 4.77 | 17100.0 | 2 |
| Phosphatidylinositol 3,4,5-trisphosphate 5-phosphatase 2 CHEMBL2331064 | IC50 | 4.45 | 4.415 | 35500.0 | 2 |
| Tyrosine-protein phosphatase non-receptor type 6 CHEMBL3166 | IC50 | 4.39 | 4.39 | 40400.0 | 1 |
| Tyrosine-protein phosphatase non-receptor type 1 CHEMBL335 | IC50 | 4.21 | 4.21 | 62400.0 | 1 |
Pharmacokinetic Data
| Parameter | Value | Units | Species |
|---|---|---|---|
| CL | 0.9 | mL.min-1.kg-1 | Homo sapiens |
| CL | 0.94 | mL.min-1.kg-1 | Homo sapiens |
| CL | 0.94 | mL.min-1.kg-1 | Homo sapiens |
| MRT | 2.1 | hr | Homo sapiens |
| T1/2 | 2.4 | hr | Homo sapiens |
Activity Data Samples
Top measurements by pChEMBL value
| Target | Type | Rel. | Value | Units | pChEMBL | Assay | PubMed |
|---|---|---|---|---|---|---|---|
| Tyrosine-protein phosphatase non-receptor type 11 | Kd | = | 8400.0 | nM | 5.08 | Binding affinity to recombinant SHP2 by surface plasmon response | 21193311 |
| Tyrosine-protein phosphatase non-receptor type 11 | IC50 | = | 17100.0 | nM | 4.77 | Inhibition of recombinant SHP2 | 21193311 |
| Tyrosine-protein phosphatase non-receptor type 11 | IC50 | = | 17100.0 | nM | 4.77 | Inhibition of SHP2 (unknown origin) | 35157464 |
| Phosphatidylinositol 3,4,5-trisphosphate 5-phosphatase 2 | IC50 | = | 35500.0 | nM | 4.45 | Inhibition of 2-FAM-InsP5 binding to human SHIP2 catalytic domain (419 to 832 re... | 33724834 |
| Tyrosine-protein phosphatase non-receptor type 6 | IC50 | = | 40400.0 | nM | 4.39 | Inhibition of recombinant SHP1 | 21193311 |
| Phosphatidylinositol 3,4,5-trisphosphate 5-phosphatase 2 | IC50 | = | 41700.0 | nM | 4.38 | Inhibition of human SHIP2 catalytic domain (419 to 832 residues) phosphatase act... | 33724834 |
| Tyrosine-protein phosphatase non-receptor type 1 | IC50 | = | 62400.0 | nM | 4.21 | Inhibition of recombinant PTP1B | 21193311 |
Literature References
| PubMed | DOI | Target Context | # Activities |
|---|---|---|---|
| 20070106 | 10.1021/jm901371v | Homo sapiens | 8 |
| 18426954 | 10.1124/dmd.108.020479 | ADMET | 4 |
| 21193311 | 10.1016/j.bmcl.2010.11.117 | Tyrosine-protein phosphatase non-receptor type 11 | 4 |
| 33724834 | 10.1021/acs.jmedchem.0c01944 | Phosphatidylinositol 3,4,5-trisphosphate 5-phosphatase 2 | 3 |
| 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 | Muscarinic acetylcholine receptor M1 | 2 |
| - | 10.6019/CHEMBL4808148 | Histone deacetylase 6 | 2 |
| 37468498 | 10.1038/s41467-023-40064-9 | Alpha-1A adrenergic receptor | 2 |
| 35157464 | 10.1021/acs.jmedchem.1c02008 | Tyrosine-protein phosphatase non-receptor type 11 | 1 |
| 37468498 | 10.1038/s41467-023-40064-9 | Mu-type opioid receptor | 1 |
| 37468498 | 10.1038/s41467-023-40064-9 | Alpha-2A adrenergic receptor | 1 |
| 37468498 | 10.1038/s41467-023-40064-9 | Sodium-dependent noradrenaline transporter | 1 |
| 37468498 | 10.1038/s41467-023-40064-9 | Acetylcholinesterase | 1 |
| 37468498 | 10.1038/s41467-023-40064-9 | Estrogen receptor | 1 |
| 37468498 | 10.1038/s41467-023-40064-9 | Sodium-dependent dopamine transporter | 1 |
| 37468498 | 10.1038/s41467-023-40064-9 | D(1A) dopamine receptor | 1 |
| 18834112 | 10.1021/jm800656v | Amine oxidase [flavin-containing] A | 1 |
| 21193311 | 10.1016/j.bmcl.2010.11.117 | Tyrosine-protein phosphatase non-receptor type 1 | 1 |
| 21193311 | 10.1016/j.bmcl.2010.11.117 | Tyrosine-protein phosphatase non-receptor type 6 | 1 |
Data from ChEMBL 36 via Core Engine