Carbetocin

Base Information

• Chemical Name: Carbetocin
• CAS No.: 37025-55-1
• Molecular Formula: C₄₅H₆₉N₁₁O₁₂S
• Molecular Weight: 988.175
• European Community (EC) Number: 253-312-6
• UNII: 88TWF8015Y
• ChEMBL ID: CHEMBL3301668
• DSSTox Substance ID: DTXSID90897527
• Metabolomics Workbench ID: 43478
• NCI Thesaurus Code: C96858
• Nikkaji Number: J268.177C
• Pharos Ligand ID: HJ9V3GW612Z1
• Wikidata: Q5037853
• Wikipedia: Carbetocin
• Mol file: 37025-55-1.mol

Synonyms:1-deamino-1-monocarba-2-(Tyr(OMe))-oxytocin;carbetocin;dcomot;Depotocin;oxytocin, 1-desamino-1-monocarba-(Tyr(OMe))(2)-;oxytocin, 1-desamino-1-monocarba-(tyrosine(O-methyl))(2)-

Chemical Property of Carbetocin

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.541
• Boiling Point: 1477.9 °C at 760 mmHg
• PKA: 13.07±0.70(Predicted)
• Flash Point: 847.6 °C
• PSA: 387.81000
• Density: 1.218 g/cm³
• LogP: 1.96370
• Storage Temp.: -15°C
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: -1.1
• Hydrogen Bond Donor Count: 10
• Hydrogen Bond Acceptor Count: 13
• Rotatable Bond Count: 18
• Exact Mass: 987.48478785
• Heavy Atom Count: 69
• Complexity: 1850

Purity/Quality:

98% ^*data from raw suppliers

Carbetocin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC(C)C1C(=O)NC(C(=O)NC(C(=O)NC(CSCCCC(=O)NC(C(=O)N1)CC2=CC=C(C=C2)OC)C(=O)N3CCCC3C(=O)NC(CC(C)C)C(=O)NCC(=O)N)CC(=O)N)CCC(=O)N
• Isomeric 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
• Recent ClinicalTrials: Comparative Efficacy of Carbetocin and Oxytocin in Parturients at Risk of Atonic Postpartum Hemorrhage Undergoing Elective Cesarean Delivery
• Recent EU Clinical Trials: A phase III, randomized, double-blind, active, controlled, multinational, multicentre, non-inferiority trial using Carbetocin room temperature stable (RTS) for the prevention of postpartum haemorrhage during the third stage of labour in women delivering vaginally.
• Recent NIPH Clinical Trials: Effect of intramyometrial injection of carbetocin versus rectal misoprostol on blood loss during myomectomy
• Description: Carbetocin is an alternative synthetic oxytocin-receptor agonist available in Canada, the United Kingdom, and other countries，but not the United States. A large multinational randomized noninferiority trial (N=29,645) found that carbetocin was noninferior to oxytocin for prevention of postpartum hemorrhage and need for additional uterotonic agents after vaginal delivery. Carbetocin has a longer duration of action than oxytocin, eliminating the need for prolonged infusion.
• Uses: Carbetocin is an obstetric drug used to control postpartum hemorrhaging.A new synthetic analog of oxytocin, carbetocin, is long acting and also has a rapid onset of action. It is an oxytocin receptor agonist and also stimulates milk let down due to its action on oxytocin receptors of myoepithelial cells.

Technology Process of Carbetocin

There total 2 articles about Carbetocin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

C45H71N11O13S*C2HF3O2 → Carbetocin (37025-55-1)

Guidance literature:

With 4-methyl-morpholine; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; In N,N-dimethyl-formamide; at 0 - 30 ℃; for 3h;

Reference yield:

N-(fluoren-9-ylmethoxycarbonyl)glycine (29022-11-5) + Fmoc-Leu-OH (35661-60-0) + Fmoc-Pro-OH (71989-31-6) + Fmoc-Ile-OH (71989-23-6,251316-98-0) + L-Asn(Trt) (132388-59-1) + Fmoc-L-Gln(Trt)-OH (132327-80-1,200623-62-7) + 4-[(2R)-carboxy-2-(9H-fluoren-9-ylmethoxycarbonylamino)ethylsulfanyl]butyric acid tert butyl ester (102971-73-3) + N-(9-fluorenylmethoxycarbonyl)-O-methyl-L-tyrosine (77128-72-4,201335-88-8) → Carbetocin (37025-55-1)

Guidance literature:

N-(fluoren-9-ylmethoxycarbonyl)glycine; With benzotriazol-1-ol; diisopropyl-carbodiimide; In N,N-dimethyl-formamide;

With piperidine; In N,N-dimethyl-formamide;

Fmoc-Leu-OH; Fmoc-Pro-OH; Fmoc-Ile-OH; L-Asn(Trt); Fmoc-L-Gln(Trt)-OH; 4-[(2R)-carboxy-2-(9H-fluoren-9-ylmethoxycarbonylamino)ethylsulfanyl]butyric acid tert butyl ester; N-(9-fluorenylmethoxycarbonyl)-O-methyl-L-tyrosine; Further stages;

DOI:10.1021/jm500365s

Reference yield:

Carbetocin (37025-55-1) → 9-desglycineamide carbetocin

Guidance literature:

With alpha chymotrypsin; In water; at 20 ℃; pH=7.6; Enzyme kinetics;

DOI:10.1111/j.1600-0773.1997.tb00045.x

upstream raw materials:

N-(fluoren-9-ylmethoxycarbonyl)glycine

Fmoc-Leu-OH

Fmoc-Pro-OH

Fmoc-Ile-OH

Refernces

• 1、 Wi?niewski, Kazimierz,Alagarsamy, Sudarkodi,Galyean, Robert,Tariga, Hiroe,Thompson, Dorain,Ly, Brian,Wi?niewska, Halina,Qi, Steve,Croston, Glenn,Laporte, Regent,Rivière, Pierre J.-M.,Schteingart, Claudio D.. "New, potent, and selective peptidic oxytocin receptor agonists". supporting information. p. 5306 - 5317. Retrieved 2014/07/08.