Carbetocin Acetate

Carbetocin (trade name Duratocin) is an eight amino acid long analogue of oxytocin (a nonapeptide) with improved in vivo stability over oxytocin. Carbetocin primarily agonizes peripherally expressed oxytocin receptors.

Designed for biological research and industrial applications, not intended for individual clinical or medical purposes.
Carbetocin Acetate(CAS 37025-55-1)

CAT No: 10-101-42

CAS No:37025-55-1

Synonyms/Alias:Carbetocin acetate;(S)-1-((3R,6S,9S,12S,15S)-6-(2-Amino-2-oxoethyl)-9-(3-amino-3-oxopropyl)-12-((S)-sec-butyl)-15-(4-methoxybenzyl)-5,8,11,14,17-pentaoxo-1-thia-4,7,10,13,16-pentaazacycloicosane-3-carbonyl)-N-((S)-1-((2-amino-2-oxoethyl)amino)-4-methyl-1-oxopentan-2-yl)pyrr;1936459-26-5;

Chemical Name:acetic acid;N-[1-[(2-amino-2-oxoethyl)amino]-4-methyl-1-oxopentan-2-yl]-1-[6-(2-amino-2-oxoethyl)-9-(3-amino-3-oxopropyl)-12-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

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cGMP Peptide
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M.F/Formula
C47H73N11O14S
M.W/Mr.
1048.2
Sequence
Three Letter Code: Butyryl-Tyr(Me)-Ile-Gln-Asn-Cys-Pro-Leu-Gly-NH2(Disulfide bond)
Application
Carbetocin is a drug used to control postpartum hemorrhage, bleeding after giving birth, since it causes contraction of the uterus.
Activity
Agonist
Biological Activity
Carbetocin acetate, an oxytocin (OT) analogue, is an oxytocin receptor agonist with a Ki of 7.1 nM. Carbetocin acetate has high affinity to chimeric N-terminus (E1) of the oxytocin receptor (Ki=1.17 μM). Carbetocin acetate has the potential for postpartum hemorrhage research. Carbetocin acetate can crosse the blood-brain barrier and produces antidepressant-like activity via activation of oxytocin receptors in the CNS.
Target
Oxytocin Receptor

Carbetocin Acetate is a synthetic peptide analogue of the naturally occurring hormone oxytocin, designed to closely mimic its structure and biological activity while offering enhanced stability and prolonged action. As a peptide compound, Carbetocin Acetate exhibits high affinity for oxytocin receptors, making it a valuable tool for investigating receptor-mediated signaling pathways and peptide-receptor interactions. Its structural modifications confer resistance to enzymatic degradation, enabling extended functional studies in biochemical and pharmacological research. The compound's ability to induce uterotonic responses and modulate smooth muscle contractility has established it as a reference molecule in peptide research, with broad applications spanning receptor pharmacology, peptide synthesis validation, and mechanistic studies of peptide hormone action.

Receptor Pharmacology: Carbetocin Acetate serves as a precise probe for dissecting oxytocin receptor pharmacology, enabling researchers to characterize ligand-receptor binding dynamics, receptor activation profiles, and downstream signaling cascades. Its well-defined structure and robust receptor selectivity facilitate detailed studies on oxytocinergic signaling, supporting the development of new receptor modulators and advancing understanding of peptide hormone-receptor interactions. These investigations are critical for elucidating the molecular basis of receptor specificity and for benchmarking the activity of novel peptide analogues in vitro.

Peptide Structure-Activity Relationship Studies: The synthetic nature and engineered modifications of Carbetocin Acetate make it a valuable reference compound in structure-activity relationship (SAR) analyses. By comparing the biological effects and receptor affinities of Carbetocin Acetate with those of native oxytocin and other analogues, researchers gain insight into the impact of specific amino acid substitutions and chemical modifications on peptide function. Such SAR studies are fundamental for rational peptide design, supporting the optimization of stability, receptor selectivity, and pharmacokinetic properties in next-generation peptide therapeutics and research tools.

Peptide Synthesis Validation: Carbetocin Acetate is frequently employed as a standard in peptide synthesis and analytical workflows. Its defined sequence and well-characterized properties allow peptide chemists to validate synthetic protocols, optimize purification strategies, and calibrate analytical instrumentation such as HPLC and mass spectrometry. The compound's stability and consistent performance make it ideal for benchmarking synthetic efficiency and confirming the identity and purity of newly synthesized peptide analogues, thereby supporting quality control in peptide production environments.

Smooth Muscle Contractility Research: Due to its potent agonistic activity at oxytocin receptors, Carbetocin Acetate is widely used to investigate the mechanisms underlying smooth muscle contraction, particularly within uterine and myometrial tissues. Researchers utilize the compound to model contractile responses, assess receptor-mediated calcium signaling, and explore the modulation of muscle tone by peptide hormones. These studies contribute to a deeper understanding of smooth muscle physiology and the regulatory roles of peptide ligands in reproductive and non-reproductive tissues.

Peptide Hormone Signaling Pathway Elucidation: Carbetocin Acetate provides a reliable platform for dissecting the intracellular signaling events triggered by oxytocin receptor activation. By applying the compound in cell-based assays or ex vivo tissue models, investigators can map the downstream effectors, second messenger systems, and gene expression changes associated with peptide hormone stimulation. This approach enables the identification of key molecular targets and regulatory nodes, informing broader research into peptide hormone networks and their roles in physiological and pathophysiological processes.

Shipping Condition
Room temperature in continental US; may vary elsewhere.
Solubility
-20 °C
InChI
InChI=1S/C45H69N11O12S.C2H4O2/c1-6-25(4)38-44(66)51-28(15-16-34(46)57)40(62)52-31(21-35(47)58)41(63)54-32(23-69-18-8-10-37(60)50-30(42(64)55-38)20-26-11-13-27(68-5)14-12-26)45(67)56-17-7-9-33(56)43(65)53-29(19-24(2)3)39(61)49-22-36(48)59;1-2(3)4/h11-14,24-25,28-33,38H,6-10,15-23H2,1-5H3,(H2,46,57)(H2,47,58)(H2,48,59)(H,49,61)(H,50,60)(H,51,66)(H,52,62)(H,53,65)(H,54,63)(H,55,64);1H3,(H,3,4)
InChI Key
AWSBRHKQUFVWPU-UHFFFAOYSA-N
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.CC(=O)O

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