General
Preferred name
ATOSIBAN
Synonyms
RW22164 ()
RWJ22164 ()
Atosiban Acetate ()
Tractocile ()
antocin II ()
c[Mpr-D-Tyr(OEt)-Ile-Thr-Asn-Cys]-Pro-Orn-Gly-NH2 ()
ORF-22164 ()
CAP-581 ()
F-314 ()
Tractocil ()
RWJ 22164 ()
Antocin ()
Antocile ()
CAP-449 ()
ORF 22164 ()
RWJ-22164 ()
RW-22164 ()
CAP-476 ()
P&D ID
PD041599
CAS
914453-95-5
90779-69-4
Tags
available
drug
Approved by
EMA
First approval
2000
Drug Status
investigational
approved
Max Phase
Phase 4
Drug indication
Antagonist (oxytocin)
Probe control
Probe control not defined
Orthogonal probes
0
No orthogonal probes found
Similar probes
0
No structurally similar probes found
Structure
P&D probe-likeness score
Structure formats
[[ format ]]
[[ compound[format === 'MOL' ? 'molblock' : format.toLowerCase()] ]]
Description
(extracted from source data)
MOA
Atosiban is a synthetic peptide oxytocin antagonist [L2469,A32685]. It resembles oxytocin with has modifications at the 1, 2, 4, and 8 positions. The N-terminus of the cysteine residue is deaminated to form 3-mercaptopropanic acid at position 1, at position 2 L-tyrosine is modified to D-tyrosine with an ethoxy group replacing the phenol , threonine replaces glutamine at postion 4, and ornithine replaces leucine at position 8.; ; It binds to membrane bound oxytocin receptors on the myometrium and prevents oxytocin-stimulated increases in inositol triphosphate production [A32685]. This ultimately prevents release of stored calcium from the sarcoplasmic reticulum and subsequent opening of voltage gated calcium channels. This shutdown of cytosolic calcium increase prevents contractions of the uterine muscle, reducing the frequency of contractions and inducing uterine quiescence.; ; Atosiban has more recently been found to act as a biased ligand at oxytocin receptors [A32694,A32695]. It acts as an antagonist of Gq coupling, explaining the inhibition of the inositol triphosphate pathway thought to be responsible for the effect on uterine contraction, but acts as an agonist of Gi coupling. This agonism produces a pro-inflammatory effect in the human amnion, activating pro-inflammatory signal tranducer NF-κB [A32695]. It is thought that this reduces atosiban's effectiveness compared to agents which do not produce inflammation as inflammatory mediators are known to play a role in the induction of labour.
DESCRIPTION
A synthetic analogue of oxytocin. There is some ambiguity over the exact stereochemistry of atosiban. Another representation is CID 68613.
(GtoPdb)
INDICATION
Atosiban is indicated for use in delaying imminent pre-term birth in pregnant adult women with: ; ; - regular uterine contractions of at least 30 s duration at a rate of at least 4 per 30 min; - a cervical dilation of 1-3cm (0-3cm for nulliparas) and effacement of at least 50%; - a gestational age of 24-33 weeks; - a normal fetal heart rate
[[ p.pathway_name ]]
[[ compound.targets[tid].gene_name ]]
Cell lines
0
Organisms
1
Compound Sets
18
AdooQ Bioactive Compound Library
Cayman Chemical Bioactives
ChEMBL Approved Drugs
ChEMBL Drugs
Drug Repurposing Hub
DrugBank
DrugBank Approved Drugs
DrugCentral
DrugCentral Approved Drugs
DrugMAP
Guide to Pharmacology
LSP-MoA library (Laboratory of Systems Pharmacology)
Mcule NIBR MoA Box Subset
Natural product-based probes and drugs
Novartis Chemogenetic Library (NIBR MoA Box)
ReFrame library
Selleckchem Bioactive Compound Library
TargetMol Bioactive Compound Library
[[ a.name ]]
[[ ligand_id ]]
free of charge
External IDs
39
Molecular Weight
993.44
Hydrogen Bond Acceptors
15
Hydrogen Bond Donors
11
Rotatable Bonds
18
Ring Count
3
Aromatic Ring Count
1
cLogP
-3.04
TPSA
365.67
Fraction CSP3
0.63
Chiral centers
9.0
Largest ring
20.0
QED
0.07
Structural alerts
0
No structural alerts detected
Related compounds
Custom attributes
(extracted from source data)
Pathway
GPCR/G protein
Member status
member
MOA
Oxytocin (OT) Antagonists
oxytocin receptor antagonist
Disease Area
neurology/psychiatry, cardiology, endocrinology
Indication
stroke, angina pectoris, myocardial infarction, hyperlipidemia
Target
AVPR1A, AVPR1B, AVPR2, OXTR
Biosynthetic Origin
Peptide (Ribosomal)
Therapeutic Indication
Premature Birth
Therapeutic Class
Hormone Therapy
Source data
