Carbetocin acetate
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MedKoo CAT#: 464007

CAS#: 1631754-28-3 (acetate)

Description: Carbetocin is an oxytocin receptor agonist and a peptide analog of oxytocin. It selectively binds to oxytocin receptors over vasopressin V2 receptors. Carbetocin induces contraction of isolated rat uterine strips and inhibits oxytocin-induced contraction of isolated rat uterine strips. In vivo, carbetocin increases the frequency and amplitude of uterine contractions in early postpartum dairy cows. Carbetocin 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. Formulations containing carbetocin have been used in the prevention of excessive bleeding after childbirth.

Chemical Structure

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Carbetocin acetate
CAS# 1631754-28-3 (acetate)
Instruction

Theoretical Analysis

MedKoo Cat#: 464007
Name: Carbetocin acetate
CAS#: 1631754-28-3 (acetate)
Chemical Formula: C47H73N11O14S
Exact Mass: 1,047.51
Molecular Weight: 1,048.224
Elemental Analysis: C, 53.85; H, 7.02; N, 14.70; O, 21.37; S, 3.06

Price and Availability

Size Price Availability Quantity
5mg USD 250 2 Weeks
10mg USD 450 2 Weeks
50mg USD 950 2 Weeks
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Related CAS #: 1631754-28-3 (acetate)   37025-55-1 (free)  

Synonym: Carbetocin acetate;

IUPAC/Chemical Name: (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)pyrrolidine-2-carboxamide acetate

InChi Key: AWSBRHKQUFVWPU-AJDWMHSWSA-N

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

SMILES Code: O=C(N1[C@@H](CCC1)C(N[C@H](C(NCC(N)=O)=O)CC(C)C)=O)[C@H](CSCCCC(N[C@H]2CC3=CC=C(C=C3)OC)=O)NC([C@H](CC(N)=O)NC([C@H](CCC(N)=O)NC([C@@]([H])(NC2=O)[C@H](CC)C)=O)=O)=O.CC(O)=O

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Biological target:
In vitro activity:
In vivo activity:

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
Soluble in DMSO 0.0 100.00

Preparing Stock Solutions

The following data is based on the product molecular weight 1,048.22 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Zhang C, Wang X, Jiang H, Hou L, Zou L. Placenta percreta after Strassman metroplasty of complete bicornuate uterus: a case report. BMC Pregnancy Childbirth. 2021 Jan 29;21(1):95. doi: 10.1186/s12884-021-03540-y. PMID: 33514327; PMCID: PMC7844894.

2: Theunissen F, Cleps I, Goudar S, Qureshi Z, Owa OO, Mugerwa K, Piaggio G, Gülmezoglu AM, Nakalembe M, Byamugisha J, Osoti A, Mandeep S, Poriot T, Gwako G, Vernekar S, Widmer M. Cost of hospital care of women with postpartum haemorrhage in India, Kenya, Nigeria and Uganda: a financial case for improved prevention. Reprod Health. 2021 Jan 22;18(1):18. doi: 10.1186/s12978-020-01063-x. PMID: 33482858; PMCID: PMC7821537.

3: Taher A, Farouk D, Mohamed Kotb MM, Ghamry NK, Kholaif K, A Mageed A Allah A, Ali AS, Osman OM, Nabil H, Islam Y, Bakry MS, Islam BA, Alalfy M, Nassar SA, Bosilah AH, Ghanem AA, Ali Rund NM, Refaat R, Abdel Wahed Ali HA, Bakry A, Ashour ASA, Nabil M, Zaki SS. Evaluating Efficacy of Intravenous Carbetocin in Reducing Blood Loss During Abdominal Myomectomy: A Randomized Controlled Trial. Fertil Steril. 2021 Jan 15:S0015-0282(20)32334-7. doi: 10.1016/j.fertnstert.2020.09.132. Epub ahead of print. PMID: 33461754.

4: Kwon K, Kim D, Jo H, Park JE, Kim KO. Hemodynamic effects of carbetocin administered as an intravenous bolus or infusion during cesarean delivery. Anesth Pain Med (Seoul). 2020 Apr 30;15(2):167-172. doi: 10.17085/apm.2020.15.2.167. Epub 2020 Apr 29. PMID: 33329809; PMCID: PMC7713823.

5: Muro BBD, Carnevale RF, Andretta I, Leal DF, Monteiro MS, Poor AP, Almond GW, Garbossa CAP. Effects of uterotonics on farrowing traits and piglet vitality: A systematic review and meta-analysis. Theriogenology. 2021 Feb;161:151-160. doi: 10.1016/j.theriogenology.2020.12.003. Epub 2020 Dec 9. PMID: 33321392.

6: van der Nelson H, O'Brien S, Burnard S, Mayer M, Alvarez M, Knowlden J, Winter C, Dailami N, Marques E, Burden C, Siassakos D, Draycott T. Intramuscular oxytocin versus Syntometrine® versus carbetocin for prevention of primary postpartum haemorrhage after vaginal birth: a randomised double-blinded clinical trial of effectiveness, side effects and quality of life. BJOG. 2020 Dec 10. doi: 10.1111/1471-0528.16622. Epub ahead of print. PMID: 33300296.

7: Delorme P, Kayem G, Legardeur H, Roux-Dessarps LA, Girard G, Meunier G, Keita H, Mandelbrot L. Carbetocin versus Oxytocin for the Prevention of Postpartum Hemorrhage in Cesarean Deliveries: A Retrospective Study of Two Consecutive Periods. AJP Rep. 2020 Jul;10(3):e241-e246. doi: 10.1055/s-0040-1715163. Epub 2020 Aug 27. PMID: 33133760; PMCID: PMC7591351.

8: Briones JR, Talungchit P, Thavorncharoensap M, Chaikledkaew U. Economic evaluation of carbetocin as prophylaxis for postpartum hemorrhage in the Philippines. BMC Health Serv Res. 2020 Oct 26;20(1):975. doi: 10.1186/s12913-020-05834-x. PMID: 33106169; PMCID: PMC7586682.

9: Leung WC. Prevention of postpartum haemorrhage. Hong Kong Med J. 2020 Oct;26(5):370-371. doi: 10.12809/hkmj205107. PMID: 33089786.

10: Tse KY, Yu FNY, Leung KY. Comparison of carbetocin and oxytocin infusions in reducing the requirement for additional uterotonics or procedures in women at increased risk of postpartum haemorrhage after Caesarean section. Hong Kong Med J. 2020 Oct;26(5):382-389. doi: 10.12809/hkmj208683. Epub 2020 Oct 8. PMID: 33028723.

11: Imami AS, O'Donovan SM, Creeden JF, Wu X, Eby H, McCullumsmith CB, Uvnäs- Moberg K, McCullumsmith RE, Andari E. Oxytocin's anti-inflammatory and proimmune functions in COVID-19: a transcriptomic signature-based approach. Physiol Genomics. 2020 Sep 1;52(9):401-407. doi: 10.1152/physiolgenomics.00095.2020. Epub 2020 Aug 18. PMID: 32809918.

12: Onwochei DN, Owolabi A, Singh PM, Monks DT. Carbetocin compared with oxytocin in non-elective Cesarean delivery: a systematic review, meta-analysis, and trial sequential analysis of randomized-controlled trials. Can J Anaesth. 2020 Nov;67(11):1524-1534. English. doi: 10.1007/s12630-020-01779-1. Epub 2020 Aug 3. PMID: 32748189.

13: Torloni MR, Bonet M, Betrán AP, Ribeiro-do-Valle CC, Widmer M. Quality of medicines for life-threatening pregnancy complications in low- and middle-income countries: A systematic review. PLoS One. 2020 Jul 10;15(7):e0236060. doi: 10.1371/journal.pone.0236060. PMID: 32649710; PMCID: PMC7351160.

14: Patrick HS, Mitra A, Rosen T, Ananth CV, Schuster M. Pharmacologic intervention for the management of retained placenta: a systematic review and meta-analysis of randomized trials. Am J Obstet Gynecol. 2020 Sep;223(3):447.e1-447.e19. doi: 10.1016/j.ajog.2020.06.044. Epub 2020 Jun 25. PMID: 32592695.

15: Angheluta A, Guizani S, Saunier J, Rönnback R. Application of chemometric modelling to UV-Vis spectroscopy: development of simultaneous API and critical excipient assay in a liquid solution continuous flow. Pharm Dev Technol. 2020 Oct;25(8):919-929. doi: 10.1080/10837450.2020.1770789. Epub 2020 Jun 4. PMID: 32496145.

16: Ibrahim ZM, Sayed Ahmed WA, Abd El-Hamid EM, Taha OT, Elbahie AM. Carbetocin versus oxytocin for prevention of postpartum hemorrhage in hypertensive women undergoing elective cesarean section. Hypertens Pregnancy. 2020 Aug;39(3):319-325. doi: 10.1080/10641955.2020.1768268. Epub 2020 May 18. PMID: 32421401.

17: Weeks AD, Fawcus S. Management of the third stage of labour: (for the Optimal Intrapartum Care series edited by Mercedes Bonet, Femi Oladapo and Metin Gülmezoglu). Best Pract Res Clin Obstet Gynaecol. 2020 Aug;67:65-79. doi: 10.1016/j.bpobgyn.2020.03.003. Epub 2020 Mar 10. PMID: 32402601.

18: Ehab Ibrahim A, Hashem H, Elhenawee M, Saleh H. Monolithic and core-shell particles stationary phase morphologies in protein analysis; peptide mapping of erythropoietin hormone and determination of carbetocin. Ann Pharm Fr. 2020 May;78(3):206-216. doi: 10.1016/j.pharma.2020.01.008. Epub 2020 Feb 10. PMID: 32247515.

19: Williams AV, Duque-Wilckens N, Ramos-Maciel S, Campi KL, Bhela SK, Xu CK, Jackson K, Chini B, Pesavento PA, Trainor BC. Social approach and social vigilance are differentially regulated by oxytocin receptors in the nucleus accumbens. Neuropsychopharmacology. 2020 Aug;45(9):1423-1430. doi: 10.1038/s41386-020-0657-4. Epub 2020 Mar 20. PMID: 32198453; PMCID: PMC7360746.

20: Hinchcliffe JK, Mendl M, Robinson ESJ. Investigating hormone-induced changes in affective state using the affective bias test in male and female rats. Psychoneuroendocrinology. 2020 May;115:104647. doi: 10.1016/j.psyneuen.2020.104647. Epub 2020 Mar 7. PMID: 32179367; PMCID: PMC7193894.