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Carbetocin Acetate

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CAT#
10-101-42
Synonyms/Alias
Calcihexal; Calcimar; Forcaltonin; Fortical; Miacalcic; Miacalcin; Carbetocino; Carbetocinum; CID71715; EINECS 253-312-6; AC-3444; DB01282; I06-1830; AC3444; AC 3444; I06 1830
CAS No.
37025-55-1
Sequence
Butyryl-Tyr(Me)-Ile-Gln-Asn-Cys-Pro-Leu-Gly-NH2(Disulfide bond)
M.W/Mr.
988.2
Molecular Formula
C45H69N11O12S
Source
Synthetic
Long-term Storage Conditions
−20°C
Application
Carbetocin is a drug used to control postpartum hemorrhage, bleeding after giving birth, since it causes contraction of the uterus.
Description
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.
Areas of Interest
Diseases
  • Background
  • Related Products
  • References

Carbetocin, or 1-butanoic acid-2-(O-methy-L-tyrosine)-1-carbaoxytocin, is an oxytocic used in obstetrics to control postpartum hemorrhage and bleeding after giving birth, particularly following Cesarean section. It is an eight amino acid long analogue of oxytocin (a nonapeptide) and has a similar mechanism of action.

CAS: 38821-49-7
Sequence: ---
M.W: 244.24
Molecular Formula: C10H16N2O5
CAS: 638-23-3
Sequence: H-Cys(carboxymethyl)-OH
M.W: 179.19
Molecular Formula: C5H9NO4S
CAS: 35144-91-3
Sequence: H-Trp-Met-Asp-Phe-NH2 acetate
M.W: 596.71
Molecular Formula: C29H36N6O6S
CAS: 133099-04-4 (net), 133099-07-7 (hydrobromide)
Sequence: ---
M.W: 505.44606
Molecular Formula: C28H29BrN2O2
CAS: 201530-41-8
Sequence: ---
M.W: 373.3615
Molecular Formula: C21H15N3O4

Carbetocin was as effective as oxytocin in the prevention of postpartum hemorrhage in women with severe preeclampsia. Carbetocin had a safety profile similar to that of oxytocin, and it was not associated with the development of oliguria or hypertension in this cohort.

Reyes, O. A., & Gonzalez, G. M. (2011). Carbetocin versus oxytocin for prevention of postpartum hemorrhage in patients with severe preeclampsia: a double-blind randomized controlled trial. Journal of Obstetrics and Gynaecology Canada, 33(11), 1099-1104.

The aims of the present study were to compare the haemodynamic effects of oxytocin and carbetocin and to assess the efficacy of these two drugs in terms of blood loss and the additional uterotonic needed in caesarean section at high risk of primary post-partum haemorrhage.

Larciprete, G., Montagnoli, C., Frigo, M., Panetta, V., Todde, C., Zuppani, B., ... & Valensise, H. (2013). Carbetocin versus oxytocin in caesarean section with high risk of post-partum haemorrhage. Journal of prenatal medicine, 7(1), 12.

The objective of this review was to evaluate the efficacy and safety of carbetocin in the prevention of postpartum hemorrhage. All trials found during a targeted Medline and Cochrane database search were screened for eligibility. Outcome measures were estimated blood loss, uterine tone, amount and type of lochia, fundal position after delivery (number of centimeters above or below the umbilicus), side-effects, adverse effects, vital signs, levels of hemoglobin/hematocrit before delivery compared with 24 or 48 hours postpartum, the need for additional uterotonic therapy, and/or uterine massage and duration of the third stage of labor. The retrieved studies were difficult to compare because of differences in study design and outcome. We conclude that carbetocin probably is as effective as oxytocin or syntometrine in the prophylactic management of the third stage of labor. Also carbetocin has a similar safety profile to oxytocin, which is now used as a standard prophylactic treatment. However, more research on this subject is needed.

Peters, N. C., & Duvekot, J. J. (2009). Carbetocin for the prevention of postpartum hemorrhage: a systematic review. Obstetrical & gynecological survey, 64(2), 129-135.

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