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Compound Detail

CHEMBL3301668

CARBETOCIN
🧪 Phase III
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🧪 Phase III
CC[C@H](C)[C@@H]1NC(=O)[C@H](Cc2ccc(OC)cc2)NC(=O)CCCSC[C@@H](C(=O)N2CCC[C@H]2C(=O)N[C@@H](CC(C)C)C(=O)NCC(N)=O)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CCC(N)=O)NC1=O

Basic Information

ChEMBL ID CHEMBL3301668
Name CARBETOCIN
Phase Phase III
Structure Type MOL
InChI Key NSTRIRCPWQHTIA-DTRKZRJBSA-N
Therapeutic ✓ Yes

Known Names

Carbetocin Carbetocina Carbetocine Duratocin Duratocin long acting FE 992097 FE-992097 LV-101 Pabal
5
Targets
14
Activities
2
Assay Types
5
PK Parameters
20
Publications
9
Known Names
4
Indications
1
Mechanisms

Molecular Properties

988.2
MW (Da)
-2.50
ALogP
13
HBA
10
HBD
362.5
PSA (Ų)
0.07
QED
3
Ro5 Violations
18
Rot. Bonds

Drug Information

Molecule Type Protein
Chirality Single Enantiomer

Flags

Natural Product
USAN Stem -tocin
USAN Year 2020

Extended Properties

Molecular Formula C45H69N11O12S
MW 988.18
Aromatic Rings 1
Heavy Atoms 69
NP-Likeness 0.18

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Oxytocin receptor agonist AGONIST Oxytocin receptor

Indications

Postpartum Hemorrhage Prader-Willi Syndrome Leiomyoma Uterine Inertia

ATC Classification

H01BB03
carbetocin
Level 1: SYSTEMIC HORMONAL PREPARATIONS, EXCL. SEX HORMONES AND INSULINS
Level 2: PITUITARY AND HYPOTHALAMIC HORMONES AND ANALOGUES

Activity Summary

EC50 13 meas. best 9.15
Ki 1 meas. best 8.74

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Oxytocin receptor
CHEMBL2049
EC50 9.15 8.265 0.7 4
Oxytocin receptor
CHEMBL2049
Ki 8.74 8.74 1.8 1
Vasopressin V1a receptor
CHEMBL1889
EC50 8.64 8.015 2.3 2
Vasopressin V1b receptor
CHEMBL1921
EC50 8.32 6.445 4.8 2
Oxytocin receptor
CHEMBL3243907
EC50 7.21 7.21 62.0 1
Vasopressin V2 receptor
CHEMBL1790
EC50 6.77 5.9667 170.0 3

Pharmacokinetic Data

Parameter Value Units Species
CL 22.0 mL.min-1.kg-1 Rattus norvegicus
T1/2 0.6667 hr Mus musculus
T1/2 24.0 hr -
T1/2 0.2167 hr -
T1/2 0.6667 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Oxytocin receptor EC50 = 0.7 nM 9.15 Agonist activity at human oxytocin receptor expressed in CHO-K1 cells after 5 hr... 24874785
Oxytocin receptor Ki = 1.8 nM 8.74 Displacement of [3H]OT from recombinant human OTR expressed in HEK293 cell membr... 30896946
Vasopressin V1a receptor EC50 = 2.3 nM 8.64 Agonist activity at recombinant human V1a receptor expressed in HEK293 cells ass... 30896946
Oxytocin receptor EC50 = 2.99 nM 8.52 Agonist activity at recombinant human Gi/Go-coupled OTR expressed in CHOK1 cells... 31850759
Vasopressin V1b receptor EC50 = 4.8 nM 8.32 Agonist activity at recombinant human V1b receptor expressed in HEK293 cells ass... 30896946
Oxytocin receptor EC50 = 10.0 nM 8.0 Agonist activity at human OTR receptor expressed in HEK293FT cells incubated for... 30199637
Vasopressin V1a receptor EC50 = 41.0 nM 7.39 Agonist activity at human vasopressin V1a expressed in HEK293 cells after 5 hrs ... 24874785
Oxytocin receptor EC50 = 41.0 nM 7.39 Agonist activity at human OTR receptor expressed in HEK293FT cells assessed as s... 30199637
Oxytocin receptor EC50 = 62.0 nM 7.21 Agonist activity at mouse OTR receptor expressed in HEK293FT cells assessed as s... 30199637
Vasopressin V2 receptor EC50 = 170.0 nM 6.77 Agonist activity at human vasopressin V2 expressed in HEK293 cells after 5 hrs b... 24874785
Vasopressin V2 receptor EC50 = 1100.0 nM 5.96 Agonist activity at human V2 receptor expressed in HEK293FT cells incubated for ... 30199637
Vasopressin V2 receptor EC50 = 6700.0 nM 5.17 Agonist activity at human V2 receptor expressed in HEK293FT cells assessed as st... 30199637
Vasopressin V1b receptor EC50 = 27000.0 nM 4.57 Agonist activity at human V1b receptor expressed in HEK293FT cells assessed as s... 30199637

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL5058564 HEK-293T 8
30199637 10.1021/acs.jmedchem.8b00697 Oxytocin receptor 6
31850759 10.1021/acs.jmedchem.9b01862 Mus musculus 5
24874785 10.1021/jm500365s Vasopressin V1a receptor 4
30199637 10.1021/acs.jmedchem.8b00697 Vasopressin V2 receptor 4
- 10.6019/CHEMBL5058564 Fibroblast 4
24874785 10.1021/jm500365s Unchecked 3
30199637 10.1021/acs.jmedchem.8b00697 Vasopressin V1b receptor 3
30896946 10.1021/acs.jmedchem.8b01691 Oxytocin receptor 3
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
35420805 10.1021/acs.jmedchem.2c00094 ADMET 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
30896946 10.1021/acs.jmedchem.8b01691 Unchecked 2
- 10.6019/CHEMBL5209801 Apelin receptor 2
31850759 10.1021/acs.jmedchem.9b01862 Oxytocin receptor 2
- 10.6019/CHEMBL5209801 G-protein coupled receptor 35 2
30199637 10.1021/acs.jmedchem.8b00697 Vasopressin V1a receptor 2
- 10.6019/CHEMBL5209801 Glucose-dependent insulinotropic receptor 2
- 10.6019/CHEMBL5209801 Alpha-2A adrenergic receptor 2
- 10.6019/CHEMBL5209801 Free fatty acid receptor 4 2

Data from ChEMBL 36 via Core Engine