A peptide oxytocin receptor agonist
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Carbetocin (acetate)

Item No. 33234

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N-(4-mercapto-1-oxobutyl)-O-methyl-L-tyrosyl-L-isoleucyl-L-glutaminyl-L-asparaginyl-L-cysteinyl-L-prolyl-L-leucyl-glycinamide, cyclic (1→5)-thioether, acetate
CAS Number
1631754-28-3
Molecular Formula
C45H69N11O12S • XC2H4O2
Formula Weight
988.2
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 30 mg/mlEthanol: 30 mg/mlPBS (pH 7.2): 5 mg/ml
SMILES
O=C([C@@H](NC([C@@H](NC([C@@H](NC([C@@]([C@@H](C)CC)([H])NC1=O)=O)CCC(N)=O)=O)CC(N)=O)=O)CSCCCC(N[C@H]1CC2=CC=C(OC)C=C2)=O)N3[C@H](C(N[C@@H](CC(C)C)C(NCC(N)=O)=O)=O)CCC3.CC(O)=O
InChi Code
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)/t25-,28-,29-,30-,31-,32-,33-,38-;/m0./s1
InChi Key
AWSBRHKQUFVWPU-AJDWMHSWSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
Certificates of Analysis & Batch Specific Data

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    5 mg

    $95

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    10 mg

    $149

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    25 mg

    $279

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    50 mg

    $510

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    Product Description

    Carbetocin is an oxytocin receptor agonist and a peptide analog of oxytocin (Item No. 11799).1 It selectively binds to oxytocin receptors over vasopressin V2 receptors (Kds = 1.96 and 61.3 nM, respectively). Carbetocin induces contraction of isolated rat uterine strips (EC50 = 48 nM) and inhibits oxytocin-induced contraction of isolated rat uterine strips (pA2 = 8.21). In vivo, carbetocin (0.35 mg/animal) increases the frequency and amplitude of uterine contractions in early postpartum dairy cows.2 Carbetocin (6.4 mg/kg, i.p.) prevents stress-induced reinstatement of morphine-seeking behavior in mice.3 It also reverses learned helplessness and decreases social withdrawal induced by chronic unpredictable stress in tree shrews.4 Formulations containing carbetocin have been used in the prevention of excessive bleeding after childbirth.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Engstrøm, T., Barth, T., Melin, P., et al. Oxytocin receptor binding and uterotonic activity of carbetocin and its metabolites following enzymatic degradation. Eur. J. Pharmacol. 355(2-3), 203-210 (1998).

    2. Bajcsy, Á.C., Szenci, O., van der Weijden, G.C., et al. The effect of a single oxytocin or carbetocin treatment on uterine contractility in early postpartum dairy cows. Theriogenology 65(2), 400-414 (2006).

    3. Zanos, P., Georgiou, P., Wright, S.R., et al. The oxytocin analogue carbetocin prevents emotional impairment and stress-induced reinstatement of opioid-seeking in morphine-abstinent mice. Neuropsychopharmacology 39(4), 855-865 (2014).

    4. Meng, X., Shen, F., Li, C., et al. Depression-like behaviors in tree shrews and comparison of the effects of treatment with fluoxetine and carbetocin. Pharmacol. Biochem. Behav. 145, 1-8 (2016).