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CasNo: 37025-55-1
Molecular Formula: C45H69N11O12S
Description |
Carbetocin is a medication primarily used to prevent excessive bleeding after childbirth, especially following a Cesarean section. It is sold under various brand names such as Pabal and Duratocin. Carbetocin is an analog of oxytocin, a natural hormone that plays a crucial role in uterine contractions during labor. |
Uses |
Clinical studies have shown that carbetocin is as effective as oxytocin in preventing postpartum hemorrhage and the need for additional uterotonic agents after vaginal delivery. While it is a valuable option for preventing excessive bleeding after childbirth, its use may be limited in some healthcare settings due to cost considerations compared to other options like oxytocin. |
Definition |
ChEBI: Oxytocin in which the hydrogen on the phenolic hydroxy group is substituted by methyl, the amino group on the cysteine residue is substituted by hydrogen, and the sulfur of the cysteine residue is replaced by a methylene group. A synthetic carba-analogue o oxytocin, it is used to control bleeding after giving birth. Like oxytocin, it causes contraction of the uterus. |
Biochem/physiol Actions |
Carbetocin is a potent agonist of the oxytocin receptor, with improved in vivo stability over oxytocin. |
InChI:InChI=1/C45H69N11O12S/c1-6-25(4)38-44(67)50-28(15-16-34(46)58)40(63)51-30(21-35(47)59)41(64)53-31(23-69-18-8-10-37(61)55(5)33(43(66)54-38)20-26-11-13-27(57)14-12-26)45(68)56-17-7-9-32(56)42(65)52-29(19-24(2)3)39(62)49-22-36(48)60/h11-14,24-25,28-33,38,57H,6-10,15-23H2,1-5H3,(H2,46,58)(H2,47,59)(H2,48,60)(H,49,62)(H,50,67)(H,51,63)(H,52,65)(H,53,64)(H,54,66)/t25-,28-,29-,30-,31-,32-,33-,38-/m0/s1
The prolonged duration of activity after intramuscular compared with the intravenous carbetocin was significant (p = 0.020). Carbetocin produced mild lower abdominal cramping in most patients and severe pain in three patients who received 50 or 100 μg intravenously or 70 μg intramuscularly.
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.
C45H71N11O13S*C2HF3O2
Carbetocin
Conditions | Yield |
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With 4-methyl-morpholine; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; In N,N-dimethyl-formamide; at 0 - 30 ℃; for 3h;
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N-(fluoren-9-ylmethoxycarbonyl)glycine
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
Carbetocin
Conditions | Yield |
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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;
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N-(fluoren-9-ylmethoxycarbonyl)glycine
Fmoc-Leu-OH
Fmoc-Pro-OH
Fmoc-Ile-OH