Atosiban

Summary

Atosiban (CHEMBL382301) is an approved protein (ATC G02CX01) targeting AVPR1A, AVPR1B, and AVPR2; indicated across 2 conditions including endometriosis.

At a glance

• Status: Approved (max clinical phase 4)
• Modality: Protein
• ATC class: G02CX01
• Targets: 4 (AVPR1A, AVPR1B, AVPR2…)
• Indications: 2 conditions
• Clinical trials: 22
• Chemistry: 994.2 Da · C43H67N11O12S2

Identifiers

Drug identity and classification

Field	Value
ChEMBL ID	CHEMBL382301
Name	Atosiban
Type	Protein
Max phase	4
FDA approved	no
PubChem CID	5311010
ATC	G02CX01
Molecular formula	C43H67N11O12S2
Molecular weight	994.2
InChIKey	VWXRQYYUEIYXCZ-OBIMUBPZSA-N

SMILES: CC[C@H](C)[C@H]1C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@@H](CSSCCC(=O)N[C@@H](C(=O)N1)CC2=CC=C(C=C2)OCC)C(=O)N3CCC[C@H]3C(=O)N[C@@H](CCCN)C(=O)NCC(=O)N)CC(=O)N)[C@@H](C)O

IUPAC name: (2S)-N-[(2S)-5-amino-1-[(2-amino-2-oxoethyl)amino]-1-oxopentan-2-yl]-1-[(4R,7S,10S,13S,16R)-7-(2-amino-2-oxoethyl)-13-[(2S)-butan-2-yl]-16-[(4-ethoxyphenyl)methyl]-10-[(1R)-1-hydroxyethyl]-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentazacycloicosane-4-carbonyl]pyrrolidine-2-carboxamide

Also known as: Antocile, Antocin, Antocin ii, Atosiban, CAP-449, CAP-476, CAP-581, F-314, ORF 22164, ORF-22164, RW-22164, RWJ 22164

Parent form; salt/anhydrous children: CHEMBL5315050

Patent coverage: 640 distinct patent families (2,367 SureChEMBL compound mentions), from 1 matched compound structure(s). Mentions count patents naming the compound (not distinct inventions), so promiscuous / reference molecules inflate the mention figure — families are the dedup metric.

Targets

Targets

Primary targets (GtoPdb curated mechanism): the Cancer dependency column is the DepMap CRISPR fitness signal (% of screened cell lines dependent on the target).

Gene	Target	Action	pAffinity	Cancer dependency	UniProt
AVPR1A	V1A receptor	Antagonist	8.5	4.6%	P37288
AVPR1B	V1B receptor	Antagonist	6.6	0.4%	P47901
AVPR2	V2 receptor	Antagonist	6	0%	P30518
OXTR	OT receptor	Antagonist	7.6	0.1%	P30559

Broader ChEMBL bioactivity targets: 5 (assay-derived). Sample: Vasopressin V2 receptor, Vasopressin V1a receptor, Vasopressin V1b receptor, Oxytocin receptor, Oxytocin receptor.

Bioactivity

ChEMBL activities: 18 potent at pChembl ≥ 5 of 18 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):

Target	pChembl	Type	Value	Unit	Activity ID
AVPR1A	9.82	Ki	0.15	nM	CHEMBL_ACT_2089519
AVPR1A	9.2	Ki	0.63	nM	CHEMBL_ACT_1659077
AVPR1A	8.33	Ki	4.7	nM	CHEMBL_ACT_2488028
P70536	8.29	Kd	5.13	nM	CHEMBL_ACT_1945516
OXTR	7.96	Ki	11	nM	CHEMBL_ACT_2089517
P70536	7.92	IC50	12	nM	CHEMBL_ACT_1683309
AVPR1A	7.7	AC50	20	nM	CHEMBL_ACT_25162029
OXTR	7.57	Ki	27	nM	CHEMBL_ACT_1657887
OXTR	7.5	Ki	32	nM	CHEMBL_ACT_2089518
P70536	7.4	Ki	39.81	nM	CHEMBL_ACT_1732818
OXTR	7.4	Ki	39.81	nM	CHEMBL_ACT_1732821
AVPR1B	7.36	Ki	44	nM	CHEMBL_ACT_2089520
OXTR	7.23	IC50	59	nM	CHEMBL_ACT_1657807
P70536	7.12	Ki	76	nM	CHEMBL_ACT_1657796
AVPR2	6.48	Ki	330	nM	CHEMBL_ACT_2089521
OXTR	6.43	IC50	372	nM	CHEMBL_ACT_18343908
OXTR	6.4	Ki	397	nM	CHEMBL_ACT_2488026
AVPR2	5.43	AC50	3700	nM	CHEMBL_ACT_25163181

Target pathways

Aggregated over 4 target gene(s): AVPR1A, AVPR1B, AVPR2, OXTR.

Top Reactome pathways

8 total, by targets touching each:

Pathway	Targets	Genes
Vasopressin-like receptors	4	AVPR1A, AVPR1B, AVPR2, OXTR
G alpha (q) signalling events	3	AVPR1A, AVPR1B, OXTR
Defective AVP does not bind AVPR1A,B and causes neurohypophyseal diabetes insipidus (NDI)	2	AVPR1A, AVPR1B
G alpha (s) signalling events	1	AVPR2
Vasopressin regulates renal water homeostasis via Aquaporins	1	AVPR2
Cargo recognition for clathrin-mediated endocytosis	1	AVPR2
Clathrin-mediated endocytosis	1	AVPR2
Defective AVP does not bind AVPR2 and causes neurohypophyseal diabetes insipidus (NDI)	1	AVPR2

Dominant GO biological processes

GO term	Targets
regulation of systemic arterial blood pressure by vasopressin	4
G protein-coupled receptor signaling pathway	4
cellular response to hormone stimulus	4
positive regulation of vasoconstriction	4
signal transduction	4
positive regulation of blood pressure	3
positive regulation of systemic arterial blood pressure	2
positive regulation of cytosolic calcium ion concentration	2
positive regulation of cell population proliferation	2
telencephalon development	2
transport across blood-brain barrier	2
regulation of blood pressure	2
maternal aggressive behavior	1
generation of precursor metabolites and energy	1
negative regulation of female receptivity	1

Indications & clinical

Indications

2 indications (0 at ChEMBL trial phase 4). Phase below is the highest clinical-trial phase recorded for this drug against each disease — not the molecule’s overall approval status (that is in the Summary).

Indication	Trial phase	MONDO	EFO
endometriosis	2	MONDO:0005133	EFO:0001065

1 further indication record had no mapped disease name (EFO/MeSH-only) or were duplicates, and are omitted.

Clinical trials

Total trials: 22.

Phase distribution

Phase	Trials
Not specified	6
PHASE4	4
PHASE3	4
PHASE2	4
PHASE1	2
EARLY_PHASE1	2

Top trials by phase / activity

NCT	Phase	Status	Title
NCT00599898	PHASE4	COMPLETED	Nifedipine Compared to Atosiban for Treating Preterm Labor
NCT01501214	PHASE4	COMPLETED	Use of Atosiban in in Vitro Fertilization (IVF) Treatment
NCT01673399	PHASE4	COMPLETED	Oxytocin Antagonist in Patients With Repeated Failure of Implantation
NCT05693688	PHASE4	COMPLETED	Atosiban Versus Placebo in the Treatment of Late Threatened Pre-term Birth
NCT01314859	PHASE3	WITHDRAWN	Nifedipine Treatment in Preterm Labor
NCT02292771	PHASE3	TERMINATED	A Randomized Study Comparing the Efficacy and Safety of Retosiban Versus Atosiban for Women in Spontaneous Preterm Labour
NCT02292784	PHASE3	COMPLETED	Follow up Study to Assess Long Term Safety and Outcomes in Infants and Children Born to Mothers Participating in Retosiban Treatment Studies
NCT02725736	PHASE3	UNKNOWN	Tocolytic Therapy for Preterm Labor in Multiple Gestation
NCT00587327	PHASE2	COMPLETED	Effect of Oxytocin and Vasopressin Antagonists on Uterine Contractions
NCT01429545	PHASE2	COMPLETED	Single Versus Combination Therapy in Acute Tocolysis
NCT03369262	PHASE2	UNKNOWN	PoC Study of OBE022 in Threatened Preterm Labour
NCT05382143	PHASE2	UNKNOWN	The Effect of Selective Oxytocin Receptor Inhibitors on Endometriosis-related Pain
NCT00679705	PHASE1	COMPLETED	Influence of Tocolytical Medications on Hemodynamics (Central and Peripheral) and Vascular Function in a Pilot Study to Determine the Design of the Final Study and the Final Study Itself
NCT02893722	PHASE1	UNKNOWN	A Randomized Double Blind Comparison of Atosiban in Patients With RIF Undergoing IVF Treatment
NCT07093060	EARLY_PHASE1	RECRUITING	The Effect of Oral Oxytocin and Atosiban on Social Attention
NCT07140237	EARLY_PHASE1	RECRUITING	The Effect of Oral Oxytocin and Atosiban on Top-down Attention ( OTAtosiban )
NCT07185230	Not specified	RECRUITING	Atosiban in Women With Previous Implantation Failure and Abnormal Uterine Contractions
NCT01493440	Not specified	COMPLETED	Atosiban Improves Implantation and Pregnancy Rates in Patients With Repeated Implantation Failure
NCT03570294	Not specified	COMPLETED	Oxidative Stress in Women Treated With Atosiban for Impending Preterm Birth
NCT03904745	Not specified	UNKNOWN	Effect of Oxytocin Antagonists on Implantation Success Rates of Frozen-thawed Embryo Transfer
NCT04468568	Not specified	COMPLETED	In Utero Repair of Myelomeningocele: Atosiban Versus Terbutaline
NCT06537778	Not specified	COMPLETED	Perioperative Use of Atosiban for Ultrasound-indicated Cerclage to Reduce Spontaneous Preterm Birth(sPTB)

Clinical evidence (CIViC)

No CIViC predictive evidence (expected for non-precision-medicine drugs).

Pharmacology

Pharmacogenomics

No PharmGKB pharmacogenomic data curated for this drug.

Related molecules

Related molecules

Molecules sharing ≥1 of this drug’s curated primary targets, merged from two biobtree sources and ranked by shared-target count, then clinical phase: ChEMBL clinical-stage candidates (development phase ≥2) and PubChem drug-class bioactivity (approved / known drugs acting on the target). Deduplicated by drug name; the drug’s own salt forms are excluded. Note: for a drug with few primary targets a shared-target match can reflect off-target / promiscuous binding rather than the same therapeutic mechanism — the phase ordering surfaces bona-fide therapeutics first.

143 molecules share ≥1 primary target. Top 60 by shared-target count:

Molecule	Source	Status	Shared targets
DESMOPRESSIN	ChEMBL + PubChem	Phase 4 (approved)	AVPR1A, AVPR1B, AVPR2, OXTR
OXYTOCIN	ChEMBL + PubChem	Phase 4 (approved)	AVPR1A, AVPR1B, AVPR2, OXTR
CARBETOCIN	ChEMBL	Phase 4 (approved)	AVPR1A, AVPR1B, AVPR2, OXTR
MOZAVAPTAN	ChEMBL	Phase 4 (approved)	AVPR1A, AVPR1B, AVPR2, OXTR
VASOPRESSIN	ChEMBL	Phase 4 (approved)	AVPR1A, AVPR1B, AVPR2, OXTR
NELIVAPTAN	ChEMBL	Phase 2	AVPR1A, AVPR1B, AVPR2, OXTR
ORNIPRESSIN	ChEMBL	Phase 2	AVPR1A, AVPR1B, AVPR2, OXTR
PECAVAPTAN	ChEMBL	Phase 2	AVPR1A, AVPR1B, AVPR2, OXTR
SELEPRESSIN	ChEMBL	Phase 2	AVPR1A, AVPR1B, AVPR2, OXTR
LIXIVAPTAN	ChEMBL	Phase 3	AVPR1A, AVPR2, OXTR
Belzutifan	PubChem	Approved	AVPR1A, AVPR2, OXTR
PIMOZIDE	ChEMBL + PubChem	Phase 4 (approved)	AVPR1A, AVPR2
RIFAMPIN	ChEMBL + PubChem	Phase 4 (approved)	AVPR1A, AVPR2
TEGASEROD	ChEMBL + PubChem	Phase 4 (approved)	AVPR1A, AVPR2
BALSALAZIDE	ChEMBL	Phase 4 (approved)	AVPR1A, AVPR2
BOSUTINIB	ChEMBL	Phase 4 (approved)	AVPR1A, AVPR2
CHLORHEXIDINE	ChEMBL	Phase 4 (approved)	AVPR1A, AVPR2
CONIVAPTAN	ChEMBL	Phase 4 (approved)	AVPR1A, AVPR2
FLUSPIRILENE	ChEMBL	Phase 4 (approved)	AVPR1A, AVPR2
NITAZOXANIDE	ChEMBL	Phase 4 (approved)	AVPR1A, AVPR2
PYRVINIUM	ChEMBL	Phase 4 (approved)	AVPR1A, AVPR2
RIFAXIMIN	ChEMBL	Phase 4 (approved)	AVPR1A, AVPR2
TOLVAPTAN	ChEMBL	Phase 4 (approved)	AVPR1A, AVPR2
BALOVAPTAN	ChEMBL	Phase 3	AVPR1A, AVPR2
NOLASIBAN	ChEMBL	Phase 3	AVPR1A, OXTR
OTILONIUM BROMIDE	ChEMBL	Phase 3	AVPR1A, AVPR2
RETOSIBAN	ChEMBL	Phase 3	AVPR2, OXTR
SEMAXANIB	ChEMBL	Phase 3	AVPR1A, OXTR
BENZETHONIUM	ChEMBL	Phase 2	AVPR1A, AVPR2
DOMIPHEN	ChEMBL	Phase 2	AVPR1A, AVPR2
EPELSIBAN	ChEMBL	Phase 2	AVPR2, OXTR
RELCOVAPTAN	ChEMBL	Phase 2	AVPR1A, AVPR2
Abiraterone	PubChem	Approved	AVPR1A, AVPR2
acetylcysteine	PubChem	Approved	AVPR1A, AVPR2
Aclidinium Bromide	PubChem	Approved	AVPR1A, AVPR2
Acyclovir	PubChem	Approved	AVPR1A, AVPR2
Afatinib	PubChem	Approved	AVPR1A, AVPR2
Allopurinol	PubChem	Approved	AVPR1A, AVPR2
Almotriptan	PubChem	Approved	AVPR1A, AVPR2
Alogliptin	PubChem	Approved	AVPR1A, AVPR2
aminolevulinic acid	PubChem	Approved	AVPR1A, AVPR2
Anagrelide	PubChem	Approved	AVPR1A, AVPR2
Apixaban	PubChem	Approved	AVPR1A, AVPR2
Aprepitant	PubChem	Approved	AVPR1A, AVPR2
Bosentan	PubChem	Approved	AVPR1A, AVPR2
Clofarabine	PubChem	Approved	AVPR1A, AVPR2
Clozapine	PubChem	Approved	AVPR1A, AVPR2
Crizotinib	PubChem	Approved	AVPR1A, AVPR2
Dacarbazine	PubChem	Approved	AVPR1A, AVPR2
Desloratadine	PubChem	Approved	AVPR1A, AVPR2
Desoxycorticosterone Pivalate	PubChem	Approved	AVPR1A, AVPR2
Didanosine	PubChem	Approved	AVPR1A, AVPR2
Dihydroergotamine	PubChem	Approved	AVPR1A, AVPR2
Erythromycin	PubChem	Approved	AVPR1A, AVPR2
Ethambutol	PubChem	Approved	AVPR1A, AVPR2
Fidaxomicin	PubChem	Approved	AVPR1A, AVPR2
Fulvestrant	PubChem	Approved	AVPR1A, AVPR2
Ganciclovir	PubChem	Approved	AVPR1A, AVPR2
Gefitinib	PubChem	Approved	AVPR1A, AVPR2
Glycopyrrolate	PubChem	Approved	AVPR1A, AVPR2