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Compound Detail

CHEMBL382301

ATOSIBAN
💊 Approved Drug
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💊 Approved Drug
CCOc1ccc(C[C@H]2NC(=O)CCSSC[C@@H](C(=O)N3CCC[C@H]3C(=O)N[C@@H](CCCN)C(=O)NCC(N)=O)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H]([C@@H](C)CC)NC2=O)cc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL382301
Name ATOSIBAN
Phase Approved
Structure Type MOL
InChI Key VWXRQYYUEIYXCZ-OBIMUBPZSA-N
Therapeutic ✓ Yes

Known Names

Antocile Antocin Antocin ii Atosiban CAP-449 CAP-476 CAP-581 F-314 ORF 22164 ORF-22164 RW-22164 RWJ 22164 +3 more
6
Targets
18
Activities
3
Assay Types
0
PK Parameters
20
Publications
15
Known Names
2
Indications
1
Mechanisms

Molecular Properties

994.2
MW (Da)
-3.04
ALogP
15
HBA
11
HBD
365.7
PSA (Ų)
0.07
QED
3
Ro5 Violations
18
Rot. Bonds

Drug Information

Molecule Type Protein
First Approval 2000
Availability Unknown
Chirality Single Enantiomer

Routes of Administration

Parenteral

Flags

Natural Product
USAN Stem -siban
USAN Year 1989

Extended Properties

Molecular Formula C43H67N11O12S2
MW 994.21
Aromatic Rings 1
Heavy Atoms 68
NP-Likeness 0.55

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Oxytocin receptor antagonist ANTAGONIST Oxytocin receptor ✓ ✓

Indications

Premature Birth Endometriosis

ATC Classification

G02CX01
atosiban
Level 1: GENITO URINARY SYSTEM AND SEX HORMONES
Level 2: OTHER GYNECOLOGICALS

Activity Summary

Ki 12 meas. best 9.82
IC50 4 meas. best 7.92
Kd 2 meas. best 8.29

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Vasopressin V1a receptor
CHEMBL1889
 Ki 9.82 9.1167 0.1 3
Oxytocin receptor
CHEMBL3996
 Kd 8.29 8.29 5.1 1
Oxytocin receptor
CHEMBL2049
 Ki 7.96 7.366 11.0 5
Oxytocin receptor
CHEMBL3996
 IC50 7.92 7.92 12.0 1
Oxytocin receptor
CHEMBL3996
 Ki 7.4 7.26 39.8 2
Vasopressin V1b receptor
CHEMBL1921
 Ki 7.36 7.36 44.0 1
Oxytocin receptor
CHEMBL2049
 IC50 7.23 6.83 59.0 2
Rattus norvegicus
CHEMBL376
 IC50 6.73 6.73 186.0 1
Vasopressin V2 receptor
CHEMBL1790
 Ki 6.48 6.48 330.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Vasopressin V1a receptor Ki = 0.15 nM 9.82 Binding affinity to human vasopressin V1a receptor 18032036
Vasopressin V1a receptor Ki = 0.63 nM 9.2 Displacement of [125I]LVA antagonist from human vasopressin 1a receptor expresse... 16302826
Vasopressin V1a receptor Ki = 4.7 nM 8.33 Binding affinity to vasopressin V1a receptor 19095447
Oxytocin receptor Kd = 5.129 nM 8.29 Antagonist activity in rat uterus by uterotonic assay 17316912
Oxytocin receptor Ki = 11.0 nM 7.96 Binding affinity to human oxytocin receptor 18032036
Oxytocin receptor IC50 = 12.0 nM 7.92 Antagonism of OT-induced response at OT receptor in rat uterine strips 16297621
Oxytocin receptor Ki = 27.0 nM 7.57 Displacement of [125I]OVTA antagonist from human oxytocin receptor expressed in ... 16302826
Oxytocin receptor Ki = 32.0 nM 7.5 Binding affinity to recombinant oxytocin receptor 18032036
Oxytocin receptor Ki = 39.81 nM 7.4 Displacement of [3H]oxytocin from human OTR 16821776
Oxytocin receptor Ki = 39.81 nM 7.4 Displacement of [3H]oxytocin from rat OTR 16821776
Vasopressin V1b receptor Ki = 44.0 nM 7.36 Binding affinity to human vasopressin V1b receptor 18032036
Oxytocin receptor IC50 = 59.0 nM 7.23 Inhibitory activity against human Oxytocin induced intracellular Calcium mobiliz... 16302826
Oxytocin receptor Ki = 76.0 nM 7.12 Displacement of [125I]OVTA antagonist from rat oxytocin receptor expressed in HE... 16302826
Rattus norvegicus IC50 = 186.0 nM 6.73 Reduction in oxytocin-induced uterine contraction in iv dosed anaesthetized rat 16821776
Vasopressin V2 receptor Ki = 330.0 nM 6.48 Binding affinity to human vasopressin V2 receptor 18032036
Oxytocin receptor IC50 = 372.0 nM 6.43 Antagonist activity at human OTR expressed in HEK293 cell membranes assessed as ... 28505537
Oxytocin receptor Ki = 397.0 nM 6.4 Binding affinity to oxytocin receptor 19095447

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL5209801 C5a anaphylatoxin chemotactic receptor 1 5
- 10.6019/CHEMBL5209801 Apelin receptor 5
- 10.6019/CHEMBL5209801 Glucagon-like peptide 1 receptor 5
- 10.6019/CHEMBL5058564 HEK-293T 5
- 10.6019/CHEMBL5058564 Fibroblast 5
- 10.6019/CHEMBL5209801 Sphingosine 1-phosphate receptor 1 5
- 10.6019/CHEMBL5209801 CX3C chemokine receptor 1 5
- 10.6019/CHEMBL5209801 Beta-2 adrenergic receptor 5
- 10.6019/CHEMBL5209801 Type-1 angiotensin II receptor 5
- 10.6019/CHEMBL5209801 Glucose-dependent insulinotropic receptor 5
- 10.6019/CHEMBL5209801 N-formyl peptide receptor 2 5
- 10.6019/CHEMBL5209801 Free fatty acid receptor 4 5
- 10.6019/CHEMBL5209801 Alpha-2A adrenergic receptor 5
- 10.6019/CHEMBL5058564 U2OS 5
- 10.6019/CHEMBL5209801 Adhesion G-protein coupled receptor F1 5
17316912 10.1016/j.ejmech.2006.12.016 Oxytocin receptor 4
16302826 10.1021/jm050645f Oxytocin receptor 3
37468498 10.1038/s41467-023-40064-9 Nuclear receptor subfamily 1 group I member 2 3
18032036 10.1016/j.bmcl.2007.11.008 Oxytocin receptor 2
16302826 10.1021/jm050645f No relevant target 2

Data from ChEMBL 36 via Core Engine