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Compound Detail

CHEMBL373742

VASOPRESSIN
💊 Approved Drug
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💊 Approved Drug
N=C(N)NCCC[C@H](NC(=O)[C@@H]1CCCN1C(=O)[C@@H]1CSSC[C@H](N)C(=O)N[C@@H](Cc2ccc(O)cc2)C(=O)N[C@@H](Cc2ccccc2)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC(N)=O)C(=O)N1)C(=O)NCC(N)=O

Basic Information

ChEMBL ID CHEMBL373742
Name VASOPRESSIN
Phase Approved
Structure Type BOTH
InChI Key KBZOIRJILGZLEJ-LGYYRGKSSA-N
Therapeutic ✓ Yes

Known Names

Arginine vasopressin Argipressin or lypressin Beta-hypophamine Inyectable de vasopresina Leiormone Solute injectable de vasopressine Vasophysin Vasopressin Vasopressin component of hbn-1 Vasopressin injection Vasopressin, unspecified Vasostrict
11
Targets
63
Activities
4
Assay Types
5
PK Parameters
20
Publications
12
Known Names
20
Indications
1
Mechanisms

Molecular Properties

1084.2
MW (Da)

Drug Information

Molecule Type Protein
First Approval 2014
Availability Prescription
Chirality Single Enantiomer

Routes of Administration

Parenteral
USAN Stem -pressin

Extended Properties

Molecular Formula C46H65N15O12S2
MW 1084.25

Mechanism of Action

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

Indications

Diabetes Insipidus Sepsis Heart Arrest Heart Diseases Myoma Pain Shock Shock, Septic Syndrome Acute Lung Injury Autistic Disorder Child Development Disorders, Pervasive Death, Sudden, Cardiac Depressive Disorder, Major Hernias, Diaphragmatic, Congenital Hypertension, Pulmonary Leiomyoma Pleural Effusion Abortion, Spontaneous Hypotension

Activity Summary

EC50 27 meas. best 10.3
Ki 27 meas. best 9.59
Kd 6 meas. best 9.19
IC50 3 meas. best 8.48

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Vasopressin V2 receptor
CHEMBL1790
EC50 10.3 9.716 0.1 5
Vasopressin V1a receptor
CHEMBL2868
EC50 10.2 10.175 0.1 2
Oxytocin receptor
CHEMBL2049
EC50 10.0 8.1283 0.1 6
Vasopressin V1a receptor
CHEMBL1889
EC50 9.63 9.112 0.2 5
Vasopressin V1a receptor
CHEMBL1889
Ki 9.59 9.0027 0.3 11
Vasopressin V1b receptor
CHEMBL2659
Ki 9.54 9.54 0.3 1
Vasopressin V2 receptor
CHEMBL3766
Ki 9.35 9.35 0.5 1
Vasopressin V1b receptor
CHEMBL1921
Ki 9.31 9.06 0.5 3
Vasopressin V1a receptor
CHEMBL2868
Kd 9.19 9.19 0.6 2
Vasopressin V1 receptor
CHEMBL2095221
Kd 9.19 9.19 0.7 2
Oxytocin receptor
CHEMBL3996
Ki 8.93 8.93 1.2 1
Vasopressin V2 receptor
CHEMBL1790
Ki 8.92 8.53 1.2 4
Vasopressin V2 receptor
CHEMBL2344
Kd 8.82 8.82 1.5 1
Vasopressin V2 receptor
CHEMBL3766
Kd 8.82 8.82 1.5 1
Vasopressin V1a receptor
CHEMBL2868
Ki 8.81 8.81 1.5 1
Oxytocin receptor
CHEMBL2049
Ki 8.78 8.478 1.6 5
Vasopressin V1b receptor
CHEMBL1921
EC50 8.7 7.9314 2.0 7
Vasopressin V2 receptor
CHEMBL3944
IC50 8.48 8.48 3.3 1
Vasopressin V1 receptor
CHEMBL2095221
IC50 8.0 8.0 10.0 1
Vasopressin V2 receptor
CHEMBL1790
IC50 6.62 6.62 242.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL - - Rattus norvegicus
T1/2 1.7 hr Homo sapiens
T1/2 24.0 hr -
T1/2 0.05 hr -
Vd 0.067 L.kg-1 Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Vasopressin V2 receptor EC50 = 0.05 nM 10.3 Agonist activity at recombinant human vasopressin V2 receptor expressed in HEK29... 21688787
Vasopressin V2 receptor EC50 = 0.05012 nM 10.3 Agonist activity at recombinant human vasopressin V2 receptor expressed in HEK29... 21688787
Vasopressin V2 receptor EC50 = 0.05 nM 10.3 Agonist activity at human vasopressin V2 expressed in HEK293 cells after 5 hrs b... 24874785
Vasopressin V2 receptor EC50 = 0.052 nM 10.28 Binding to human V2 receptor expressed in LV2 cells by cAMP production 16297621
Vasopressin V1a receptor EC50 = 0.0631 nM 10.2 Agonist activity at recombinant rat vasopressin V1a receptor expressed in HEK293... 21688787
Vasopressin V1a receptor EC50 = 0.07 nM 10.15 Agonist activity at recombinant rat vasopressin V1a receptor expressed in HEK293... 21688787
Oxytocin receptor EC50 = 0.1 nM 10.0 Agonist activity at recombinant human OTR expressed in HEK293 cells assessed as ... 30896946
Vasopressin V1a receptor EC50 = 0.2344 nM 9.63 Agonist activity at recombinant human vasopressin V1a receptor expressed in HEK2... 21688787
Vasopressin V1a receptor EC50 = 0.24 nM 9.62 Agonist activity at recombinant human vasopressin V1a receptor expressed in HEK2... 21688787
Vasopressin V1a receptor EC50 = 0.24 nM 9.62 Agonist activity at human vasopressin V1a expressed in HEK293 cells after 5 hrs ... 24874785
Vasopressin V1a receptor Ki = 0.26 nM 9.59 Inhibition of human vasopressin V1a receptor expressed in CHO cells by polarisat... 17850055
Vasopressin V1b receptor Ki = 0.29 nM 9.54 Displacement of [3H]AVP from rat vasopressin V1b receptor expressed in At-T20 ce... 17300166
Vasopressin V1a receptor Ki = 0.35 nM 9.46 Inhibition of human vasopressin V1a receptor expressed in CHO cells by polarisat... 17850055
Vasopressin V2 receptor Ki = 0.45 nM 9.35 Displacement of [3H]AVP from vasopressin V2 receptor in rat kidney membranes 17300166
Vasopressin V1b receptor Ki = 0.49 nM 9.31 Displacement of [3H]-AVP from human vasopressin V1b receptor expressed in CHO ce... 22984902
Vasopressin V1a receptor Ki = 0.56 nM 9.25 Inhibition of human vasopressin V1a receptor expressed in COS7 cells by fluoresc... 17850055
Vasopressin V1 receptor Kd = 0.65 nM 9.19 Inhibition of radioligand [3H]AVP binding to V1 receptor in rat liver plasma mem... 7507528
Vasopressin V1 receptor Kd = 0.65 nM 9.19 Compound was evaluated for its dissociation constant (Kd) to rat liver Vasopress... 10201826
Vasopressin V1a receptor Kd = 0.6457 nM 9.19 Negative log of Kd. 1732523
Vasopressin V1a receptor Kd = 0.64 nM 9.19 Binding potency against V1 receptor in rat liver cells 1732523

Literature References

PubMed DOI Target Context # Activities
23312470 10.1016/j.bmcl.2012.12.041 ADMET 9
17850055 10.1021/jm061404q Vasopressin V1a receptor 9
490538 10.1021/jm00194a008 Rattus norvegicus 8
19418631 10.1016/j.ejmech.2008.12.010 Rattus norvegicus 5
21688787 10.1021/jm200278m Vasopressin V1a receptor 4
21428295 10.1021/jm1016208 Unchecked 3
926117 10.1021/jm00219a012 Rattus norvegicus 3
24874785 10.1021/jm500365s Unchecked 3
15537356 10.1021/jm040813o Rattus norvegicus 3
21428295 10.1021/jm1016208 Oxytocin receptor 3
1732523 10.1021/jm00079a020 Vasopressin V1a receptor 3
6187921 10.1021/jm00358a018 Rattus norvegicus 3
30896946 10.1021/acs.jmedchem.8b01691 Oxytocin receptor 3
10406639 10.1016/s0960-894x(99)00269-3 Rattus norvegicus 3
950656 10.1021/jm00228a023 Rattus norvegicus 3
3612693 10.1021/jm00391a040 Rattus norvegicus 3
22984902 10.1021/jm3006146 Vasopressin V2 receptor 3
21428295 10.1021/jm1016208 Vasopressin V1b receptor 2
7752199 10.1021/jm00010a020 Oxytocin receptor 2
2416923 10.1021/jm00151a016 Rattus norvegicus 2

Data from ChEMBL 36 via Core Engine