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Product Description
Mechanism of action
Carbetocin is a long-acting synthetic analogue of oxytocin in which structural modifications increase resistance to enzymatic degradation. It selectively activates oxytocin receptors on uterine smooth muscle, triggering phospholipase C activation, inositol trisphosphate (IP₃) release, and calcium mobilisation from intracellular stores. This produces strong, sustained uterine contractions and stimulation of myoepithelial cells in the mammary gland.
Benefits and advantages
Used in obstetric pharmacology, oxytocin-receptor signalling studies, uterine-contractility models, receptor-desensitisation research and peptide-agonist structure–activity relationship investigations. Its prolonged action compared with oxytocin makes it particularly useful for modelling sustained uterotonic effects.
Side effects and risks
Risks include uterine hyperstimulation, hypotension, tachycardia, nausea, headache and, rarely, water intoxication due to oxytocin-like antidiuretic effects. Handle as a potent uterotonic peptide with appropriate biosafety precautions.
Datasheet
| Molecular Formula | C45H69N11O12S |
|---|---|
| Molecular Weight | 988.2 g/mol |
| CAS Number | 6170-42-9 |
| Storage Condition | Store in a cool, dry place. Keep container tightly closed. Protect from moisture and light. |
| Solubility | 2.65e-02 g/L |
| Purity | Purity information is available upon request (COA). |
| Synonym | Carbetocin; 37025-55-1; Pabal; Carbetocino; Carbetocinum |
| IUPAC/Chemical 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 |
| InChl Key | NSTRIRCPWQHTIA-DTRKZRJBSA-N |
| InChl Code | InChI=1S/C45H69N11O12S/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/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)/t25-,28-,29-,30-,31-,32-,33-,38-/m0/s1 |
| References |
3D Conformer.
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