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MedKoo Cat#: 412297 | Name: Carbetocin
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

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

Carbetocin
Carbetocin
CAS#37025-55-1 (free base)

Theoretical Analysis

MedKoo Cat#: 412297

Name: Carbetocin

CAS#: 37025-55-1 (free base)

Chemical Formula: C45H69N11O12S

Exact Mass: 987.4848

Molecular Weight: 988.17

Elemental Analysis: C, 54.70; H, 7.04; N, 15.59; O, 19.43; S, 3.24

Price and Availability

Size Price Availability Quantity
5mg USD 250.00 2 Weeks
10mg USD 450.00 2 Weeks
50mg USD 950.00 2 Weeks
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Related CAS #
1631754-28-3 (acetate) 37025-55-1 (free base)
Synonym
Carbetocin; Pabal; Carbetocino; Carbetocinum
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
InChi Key
NSTRIRCPWQHTIA-DTRKZRJBSA-N
InChi 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
SMILES Code
CC[C@@H]([C@@H]1NC([C@@H](N(C(CCCSC[C@@H](C(N2CCC[C@H]2C(N[C@H](C(NCC(N)=O)=O)CC(C)C)=O)=O)NC([C@@H](NC([C@@H](NC1=O)CCC(N)=O)=O)CC(N)=O)=O)=O)C)CC3=CC=C(C=C3)O)=O)C
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
>3 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

Preparing Stock Solutions

The following data is based on the product molecular weight 988.17 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
1: 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. 2: 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. 3: 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. 4: 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. 5: 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. 6: 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. 7: 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. 8: 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. 9: 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. 10: 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. 11: 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. 12: 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. 13: Clunies-Ross N, Roston TM, Taylor J, Whyte S, Albert A, Görges M, Chau A. The Effect of Carbetocin Dose on Transmural Dispersion of Myocardial Repolarization in Healthy Parturients Scheduled for Elective Cesarean Delivery Under Spinal Anesthesia: A Prospective, Randomized Clinical Trial. Anesth Analg. 2020 Mar 5. doi: 10.1213/ANE.0000000000004712. Epub ahead of print. PMID: 32149759. 14: Zhang L, Jiang Y, Wei M, Cheng BH, Zhou XC, Li J, Tian JH, Dong L, Hu RH. [Analysis of the pregnancy outcomes in pregnant women with COVID-19 in Hubei Province]. Zhonghua Fu Chan Ke Za Zhi. 2020 Mar 25;55(3):166-171. Chinese. doi: 10.3760/cma.j.cn112141-20200218-00111. PMID: 32145714. 15: Feduniw S, Warzecha D, Szymusik I, Wielgos M. Epidemiology, prevention and management of early postpartum hemorrhage - a systematic review. Ginekol Pol. 2020;91(1):38-44. doi: 10.5603/GP.2020.0009. PMID: 32039467. 16: Drew T, Balki M, Farine D, Ye XY, Downey K, Carvalho JCA. Carbetocin at elective caesarean section: a sequential allocation trial to determine the minimum effective dose in obese women. Anaesthesia. 2020 Mar;75(3):331-337. doi: 10.1111/anae.14944. Epub 2019 Dec 22. Erratum in: Anaesthesia. 2020 May;75(5):685. Downey, K [added]. PMID: 31867715. 17: Sun P, Xiao H, Wang J, Zhang S, Cao X. Pharmacokinetics and bioavailability of carbetocin after intravenous and intramuscular administration in cows and gilts. J Vet Pharmacol Ther. 2020 Mar;43(2):237-240. doi: 10.1111/jvp.12830. Epub 2019 Dec 19. PMID: 31856330. 18: Pflimlin E, Zhou Z, Amso Z, Fu Q, Lee C, Muppiddi A, Joseph SB, Nguyen-Tran V, Shen W. Engineering a Potent, Long-Acting, and Periphery-Restricted Oxytocin Receptor Agonist with Anorexigenic and Body Weight Reducing Effects. J Med Chem. 2020 Jan 9;63(1):382-390. doi: 10.1021/acs.jmedchem.9b01862. Epub 2019 Dec 18. PMID: 31850759. 19: Jin XH, Li D, Li X. Carbetocin vs oxytocin for prevention of postpartum hemorrhage after vaginal delivery: A meta-analysis. Medicine (Baltimore). 2019 Nov;98(47):e17911. doi: 10.1097/MD.0000000000017911. PMID: 31764790; PMCID: PMC6882650. 20: Maged AM, Waly M, Fahmy RM, Dieb AS, Essam A, Salah NM, Hussein EA, Nabil H. Carbetocin versus rectal misoprostol for management of third stage of labor among women with low risk of postpartum hemorrhage. Int J Gynaecol Obstet. 2020 Feb;148(2):238-242. doi: 10.1002/ijgo.13056. Epub 2019 Dec 2. PMID: 31736069.