Carbetocin
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Also known as CarbetocinaCarbetocineDuratocinDuratocin long actingFE 992097FE-992097LV-101PabalCarbitocin
Summary
Carbetocin (CHEMBL3301668) is an approved protein oxytocic (ATC H01BB03) targeting OXTR; indicated across 4 conditions including prader-willi syndrome and uterine corpus leiomyoma.
At a glance
- Status: Approved (max clinical phase 4)
- Modality: Protein
- ATC class: H01BB03
- Targets: 1 (OXTR)
- Indications: 4 conditions
- Clinical trials: 89
- Chemistry: 988.2 Da · C45H69N11O12S
Identifiers
Drug identity and classification
| Field | Value |
|---|---|
| ChEMBL ID | CHEMBL3301668 |
| Name | Carbetocin |
| Type | Protein |
| Max phase | 4 |
| FDA approved | no |
| PubChem CID | 16681432 |
| ChEBI | CHEBI:59204 |
| ATC | H01BB03 |
| Molecular formula | C45H69N11O12S |
| Molecular weight | 988.2 |
| InChIKey | NSTRIRCPWQHTIA-DTRKZRJBSA-N |
SMILES: CC[C@H](C)[C@H]1C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@@H](CSCCCC(=O)N[C@H](C(=O)N1)CC2=CC=C(C=C2)OC)C(=O)N3CCC[C@H]3C(=O)N[C@@H](CC(C)C)C(=O)NCC(=O)N)CC(=O)N)CCC(=O)N
IUPAC name: (2S)-N-[(2S)-1-[(2-amino-2-oxoethyl)amino]-4-methyl-1-oxopentan-2-yl]-1-[(3R,6S,9S,12S,15S)-6-(2-amino-2-oxoethyl)-9-(3-amino-3-oxopropyl)-12-[(2S)-butan-2-yl]-15-[(4-methoxyphenyl)methyl]-5,8,11,14,17-pentaoxo-1-thia-4,7,10,13,16-pentazacycloicosane-3-carbonyl]pyrrolidine-2-carboxamide
ChEBI definition: Oxytocin in which the hydrogen on the phenolic hydroxy group is substituted by methyl, the amino group on the cysteine residue is substituted by hydrogen, and the sulfur of the cysteine residue is replaced by a methylene group. A synthetic carba-analogue of oxytocin, it is used to control bleeding after giving birth. Like oxytocin, it causes contraction of the uterus.
Pharmacological roles (ChEBI): oxytocic.
Also known as: Carbetocin, Carbetocina, Carbetocine, Duratocin, Duratocin long acting, FE 992097, FE-992097, LV-101, Pabal, CARBETOCIN, carbetocin, Carbitocin
Patent coverage: 613 distinct patent families (1,721 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 |
|---|---|---|---|---|---|
| OXTR | OT receptor | Agonist | 8 | 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: 12 potent at pChembl ≥ 5 of 13 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):
| Target | pChembl | Type | Value | Unit | Activity ID |
|---|---|---|---|---|---|
| OXTR | 9.15 | EC50 | 0.7 | nM | CHEMBL_ACT_15001073 |
| OXTR | 8.74 | Ki | 1.8 | nM | CHEMBL_ACT_19206182 |
| AVPR1A | 8.64 | EC50 | 2.3 | nM | CHEMBL_ACT_19206200 |
| OXTR | 8.52 | EC50 | 2.99 | nM | CHEMBL_ACT_18929237 |
| AVPR1B | 8.32 | EC50 | 4.8 | nM | CHEMBL_ACT_19206209 |
| OXTR | 8 | EC50 | 10 | nM | CHEMBL_ACT_18561466 |
| AVPR1A | 7.39 | EC50 | 41 | nM | CHEMBL_ACT_15001137 |
| OXTR | 7.39 | EC50 | 41 | nM | CHEMBL_ACT_18561457 |
| P97926 | 7.21 | EC50 | 62 | nM | CHEMBL_ACT_18561459 |
| AVPR2 | 6.77 | EC50 | 170 | nM | CHEMBL_ACT_15001006 |
| AVPR2 | 5.96 | EC50 | 1100 | nM | CHEMBL_ACT_18561470 |
| AVPR2 | 5.17 | EC50 | 6700 | nM | CHEMBL_ACT_18561464 |
Target pathways
Aggregated over 1 target gene(s): OXTR.
Top Reactome pathways
2 total, by targets touching each:
| Pathway | Targets | Genes |
|---|---|---|
| Vasopressin-like receptors | 1 | OXTR |
| G alpha (q) signalling events | 1 | OXTR |
Dominant GO biological processes
| GO term | Targets |
|---|---|
| regulation of systemic arterial blood pressure by vasopressin | 1 |
| muscle contraction | 1 |
| cell surface receptor signaling pathway | 1 |
| G protein-coupled receptor signaling pathway | 1 |
| female pregnancy | 1 |
| lactation | 1 |
| cellular response to hormone stimulus | 1 |
| positive regulation of blood pressure | 1 |
| positive regulation of vasoconstriction | 1 |
| maternal process involved in parturition | 1 |
| positive regulation of cold-induced thermogenesis | 1 |
| system process | 1 |
| signal transduction | 1 |
| regulation of biological quality | 1 |
Indications & clinical
Indications
4 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 |
|---|---|---|---|
| Prader-Willi syndrome | 3 | MONDO:0008300 | MONDO:0008300 |
| uterine corpus leiomyoma | 1 | MONDO:0007886 | EFO:0000731 |
2 further indication records had no mapped disease name (EFO/MeSH-only) or were duplicates, and are omitted.
Clinical trials
Total trials: 89.
Phase distribution
| Phase | Trials |
|---|---|
| Not specified | 38 |
| PHASE4 | 32 |
| PHASE3 | 11 |
| PHASE2 | 2 |
| EARLY_PHASE1 | 2 |
| PHASE1 | 2 |
| PHASE2/PHASE3 | 1 |
| PHASE1/PHASE2 | 1 |
Top trials by phase / activity
| NCT | Phase | Status | Title |
|---|---|---|---|
| NCT06946589 | PHASE4 | NOT_YET_RECRUITING | Cardiac Changes After Effective Dose Carbetocin for Elective Caesarian Section |
| NCT07401524 | PHASE4 | RECRUITING | Carbetocin Uterotonic Treatment in Twin Pregnancies for Prevention of Postpartum Hemorrhage |
| NCT00499005 | PHASE4 | COMPLETED | Carbetocin Versus Syntometrine for the Third Stage of Labour |
| NCT00977769 | PHASE4 | COMPLETED | Carbetocin Versus Oxytocin and Hemodynamic Effects |
| NCT01579201 | PHASE4 | UNKNOWN | ED90 Determination of Carbetocin for the Prevention of Uterine Atony in Women Undergoing an Elective Cesarean Delivery |
| NCT01630187 | PHASE4 | COMPLETED | Comparison of Two Doses of Carbetocin for Prevention of Uterine Atony, During Elective Cesarean Section |
| NCT01827124 | PHASE4 | UNKNOWN | Randomized Clinical Trial for Comparison Of Intravenous Carbeitocin Versus Oxytocin In Management Of Placental Delivery In Second Trimester Interruption |
| NCT02044549 | PHASE4 | COMPLETED | Carbetocin Versus Syntometrine for Prevention of Postpartum Hemorrhage After Cesarean Section |
| NCT02101567 | PHASE4 | COMPLETED | Carbetocin Versus Oxytocin and Ergometrine for the Prevention of Postpartum Haemorrhage Following Caesarean Section |
| NCT02221531 | PHASE4 | COMPLETED | Carbetocin Trial: Carbetocin Appropriate Rate Better Equilibrium Between Tonus (TOnus) and CIrculatioN |
| NCT02277041 | PHASE4 | UNKNOWN | Carbetocin Versus Misoprostol in Cases With Placenta Previa After C.S. |
| NCT02277067 | PHASE4 | UNKNOWN | Carbetocin Versus Misoprostol in High Risk Patients for Postpartum Hemorrhage After C.S. |
| NCT02391636 | PHASE4 | COMPLETED | Carbetocin and Oxytocin in Elective Caesarean Section With High Risk of Postpartum Hemorrhage |
| NCT02528136 | PHASE4 | COMPLETED | The Clinical Carbetocin Myocardium Trial |
| NCT02636816 | PHASE4 | COMPLETED | Cardiovascular Effects of Carbetocin Given During Elective Cesarean |
| NCT02642263 | PHASE4 | UNKNOWN | Effect of the Uterotonic Carbetocin on Acute Post Cesarean-Section Pain |
| NCT03404544 | PHASE4 | COMPLETED | Impact of Carbetocin Administration on Heart Rate When Given as an Infusion Versus as a Bolus. |
| NCT03556852 | PHASE4 | COMPLETED | CARBETOCIN VERSUS RECTAL MISOPROSTOL FOR MANAGEMENT OF THIRD STAGE OF LABOR IN WOMEN AT LOW RISK OF POSTPARTUM HEMORRHAGE |
| NCT03651882 | PHASE4 | COMPLETED | Oxytocin i.m./i.v. Versus Carbetocin i.v. in Elective Cesarean Sections |
| NCT03693599 | PHASE4 | COMPLETED | Carbetocin Versus Syntometrine in Obese Women Undergoing Elective Cesarean |
| NCT03716076 | PHASE4 | COMPLETED | Carbetocin on Myocardial Repolarization Dynamics in Obstetrics Study |
| NCT03755531 | PHASE4 | COMPLETED | Carbetocin Versus Oxytocin for the Prevention of Postpartum Hemorrhage in Emergency Caesarean Delivery |
| NCT03899961 | PHASE4 | COMPLETED | Carbetocin Myocardium Trial 2014 Part 2 |
| NCT04083625 | PHASE4 | COMPLETED | the Effect of Carbetocin in Decreasing Intraoperative Blood Loss in Abdominal Myomectomy |
| NCT04300452 | PHASE4 | UNKNOWN | Carbetocin Versus Ergometrin in the Prevention of Postpartum Hemorrhage |
| NCT04357015 | PHASE4 | UNKNOWN | Intravenous Tranexamic Acid Versus IV Carbetocin in Abdominal Myomectomy |
| NCT04482959 | PHASE4 | COMPLETED | Intraoperative Carbetocin to Decrease Blood Loss During Hysteroscopic Myomectomy |
| NCT04595812 | PHASE4 | UNKNOWN | Methods to Reduce Blood Loss in Abdominal Myomectomy |
| NCT05110482 | PHASE4 | UNKNOWN | Carbetocin Versus Syntocinon for Prevention of Postpartum Hemorrhage in Cardiac Patients Undergoing Caesarean Section |
| NCT05664659 | PHASE4 | COMPLETED | Efficacy of Carbetocin Versus Oxytocin Plus Misoprostol in Decreasing Blood Loss During Cesarean Section |
| NCT05742854 | PHASE4 | UNKNOWN | Comparison Of The Effects Of Carbetocin And Oxytocin In C-Sectıon |
| NCT05806307 | PHASE4 | UNKNOWN | Methods Decreasing Bleeding in Open Myomectomy |
| NCT06173531 | PHASE3 | ACTIVE_NOT_RECRUITING | Study of Carbetocin Nasal Spray for the Treatment of Hyperphagia in Prader-Willi Syndrome |
| NCT06420297 | PHASE3 | ENROLLING_BY_INVITATION | OLE Study of Carbetocin Nasal Spray for the Treatment of Hyperphagia in Prader-Willi Syndrome |
| NCT01382732 | PHASE3 | UNKNOWN | Carbetocin vs. Oxytocin for Prevention of Postpartum Bleeding in Patients With Severe Preeclampsia |
| NCT02053922 | PHASE3 | COMPLETED | The Use of Oxytocin, Carbetocin and Buccal Misoprostol in Patients Undergoing Elective Cesarean Section (CS) |
| NCT02086994 | PHASE3 | COMPLETED | Prevention of Postpartum Hemorrhage in Patients With Severe Preeclampsia Using Carbetocin Versus Misoprostol |
| NCT02216383 | PHASE3 | COMPLETED | Intramuscular Oxytocics: A Randomised Control Trial |
| NCT02303418 | PHASE3 | UNKNOWN | Carbetocin Versus Oxytocin in the Prevention of Post Partum Haemorrhage (PPH) in Women Undergoing Caesarean Sections for Placenta Previa: A Randomised Controlled Trial |
| NCT02304042 | PHASE3 | COMPLETED | Carbetocin Versus Oxytocin in the Prevention of Post Partum Haemorrhage (PPH) in Women Delivered Vaginally With at Least 2 Risk Factors for Atonic PPH: A Randomised Controlled Trial |
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.
15 molecules share ≥1 primary target. Top 15 by shared-target count:
| Molecule | Source | Status | Shared targets |
|---|---|---|---|
| OXYTOCIN | ChEMBL + PubChem | Phase 4 (approved) | OXTR |
| ATOSIBAN | ChEMBL | Phase 4 (approved) | OXTR |
| DESMOPRESSIN | ChEMBL | Phase 4 (approved) | OXTR |
| MOZAVAPTAN | ChEMBL | Phase 4 (approved) | OXTR |
| VASOPRESSIN | ChEMBL | Phase 4 (approved) | OXTR |
| LIXIVAPTAN | ChEMBL | Phase 3 | OXTR |
| NOLASIBAN | ChEMBL | Phase 3 | OXTR |
| RETOSIBAN | ChEMBL | Phase 3 | OXTR |
| SEMAXANIB | ChEMBL | Phase 3 | OXTR |
| EPELSIBAN | ChEMBL | Phase 2 | OXTR |
| NELIVAPTAN | ChEMBL | Phase 2 | OXTR |
| ORNIPRESSIN | ChEMBL | Phase 2 | OXTR |
| PECAVAPTAN | ChEMBL | Phase 2 | OXTR |
| SELEPRESSIN | ChEMBL | Phase 2 | OXTR |
| Belzutifan | PubChem | Approved | OXTR |
Related Atlas pages
- Genes: OXTR
- Diseases: Prader-Willi syndrome
- Drugs: Oxytocin, Atosiban, Desmopressin, Mozavaptan, Vasopressin, Lixivaptan, Nolasiban, Retosiban, Semaxanib, Belzutifan