Barusiban

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

MedKoo CAT#: 466056

CAS#: 285571-64-4

Description: Barusiban is an oxytocin receptor antagonist.

Chemical Structure

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Barusiban
CAS# 285571-64-4
Instruction

Theoretical Analysis

MedKoo Cat#: 466056
Name: Barusiban
CAS#: 285571-64-4
Chemical Formula: C40H63N9O8S
Exact Mass: 829.45
Molecular Weight: 830.059
Elemental Analysis: C, 57.88; H, 7.65; N, 15.19; O, 15.42; S, 3.86

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

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Synonym: Barusiban; FE 200440; FE-200440; FE200440;

IUPAC/Chemical Name: (4S,7S,10S,13S,16R)-16-((1H-indol-3-yl)methyl)-N-((S)-5-amino-1-hydroxypentan-2-yl)-7-(2-amino-2-oxoethyl)-10-((R)-sec-butyl)-13-((S)-sec-butyl)-N-methyl-6,9,12,15,18-pentaoxo-1-thia-5,8,11,14,17-pentaazacycloicosane-4-carboxamide

InChi Key: UGNGRKKDUVKQDF-IHOMMZCZSA-N

InChi Code: InChI=1S/C40H63N9O8S/c1-6-23(3)34-38(55)46-31(20-32(42)51)36(53)45-29(40(57)49(5)26(22-50)11-10-16-41)14-17-58-18-15-33(52)44-30(19-25-21-43-28-13-9-8-12-27(25)28)37(54)47-35(24(4)7-2)39(56)48-34/h8-9,12-13,21,23-24,26,29-31,34-35,43,50H,6-7,10-11,14-20,22,41H2,1-5H3,(H2,42,51)(H,44,52)(H,45,53)(H,46,55)(H,47,54)(H,48,56)/t23-,24+,26+,29+,30-,31+,34+,35+/m1/s1

SMILES Code: CC[C@H](C)[C@H]1C(N[C@H](C(N[C@@H](CC(N)=O)C(N[C@H](C(N([C@H](CO)CCCN)C)=O)CCSCCC(N[C@H](CC2=CNC3=CC=CC=C32)C(N1)=O)=O)=O)=O)[C@@H](CC)C)=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: To be determined

Shelf Life: >2 years if stored properly

Drug Formulation: To be determined

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:

Preparing Stock Solutions

The following data is based on the product molecular weight 830.06 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: Neumann K, Griesinger G. Is oxytocin receptor antagonist administration around embryo transfer associated with IVF treatment success? A systematic review and meta-analysis. Reprod Biomed Online. 2021 Dec;43(6):983-994. doi: 10.1016/j.rbmo.2021.08.020. Epub 2021 Aug 28. PMID: 34686417.

2: Craciunas L, Tsampras N, Kollmann M, Raine-Fenning N, Choudhary M. Oxytocin antagonists for assisted reproduction. Cochrane Database Syst Rev. 2021 Sep 1;9(9):CD012375. doi: 10.1002/14651858.CD012375.pub2. PMID: 34467530; PMCID: PMC8408576.

3: Helmer H, Saleh L, Petricevic L, Knöfler M, Reinheimer TM. Barusiban, a selective oxytocin receptor antagonist: placental transfer in rabbit, monkey, and human†. Biol Reprod. 2020 Jun 23;103(1):135-143. doi: 10.1093/biolre/ioaa048. PMID: 32307542; PMCID: PMC7313255.

4: Wiśniewski K. Design of Oxytocin Analogs. Methods Mol Biol. 2019;2001:235-271. doi: 10.1007/978-1-4939-9504-2_11. PMID: 31134574.

5: Wolfe M, Wisniewska H, Tariga H, Ibanez G, Collins JC, Wisniewski K, Qi S, Srinivasan K, Hargrove D, Lindstrom BF. Selective and non-selective OT receptor agonists induce different locomotor behaviors in male rats via central OT receptors and peripheral V1a receptors. Neuropeptides. 2018 Aug;70:64-75. doi: 10.1016/j.npep.2018.05.007. Epub 2018 May 21. PMID: 29807652.

6: Flenady V, Reinebrant HE, Liley HG, Tambimuttu EG, Papatsonis DN. Oxytocin receptor antagonists for inhibiting preterm labour. Cochrane Database Syst Rev. 2014 Jun 6;(6):CD004452. doi: 10.1002/14651858.CD004452.pub3. PMID: 24903678.

7: Hughes A, Greisen G, Arce JC, Thornton S. Late preterm birth is associated with short-term morbidity but not with adverse neurodevelopmental and physical outcomes at 1 year. Acta Obstet Gynecol Scand. 2014 Jan;93(1):109-12. doi: 10.1111/aogs.12258. Epub 2013 Oct 15. PMID: 24127846.

8: Vrachnis N, Malamas FM, Sifakis S, Deligeoroglou E, Iliodromiti Z. The oxytocin-oxytocin receptor system and its antagonists as tocolytic agents. Int J Endocrinol. 2011;2011:350546. doi: 10.1155/2011/350546. Epub 2011 Dec 6. PMID: 22190926; PMCID: PMC3235456.

9: Usta IM, Khalil A, Nassar AH. Oxytocin antagonists for the management of preterm birth: a review. Am J Perinatol. 2011 Jun;28(6):449-60. doi: 10.1055/s-0030-1270111. Epub 2010 Dec 17. PMID: 21170825.

10: Pierzynski P. Oxytocin and vasopressin V(1A) receptors as new therapeutic targets in assisted reproduction. Reprod Biomed Online. 2011 Jan;22(1):9-16. doi: 10.1016/j.rbmo.2010.09.015. Epub 2010 Oct 14. PMID: 21130036.

11: Thornton S, Goodwin TM, Greisen G, Hedegaard M, Arce JC. The effect of barusiban, a selective oxytocin antagonist, in threatened preterm labor at late gestational age: a randomized, double-blind, placebo-controlled trial. Am J Obstet Gynecol. 2009 Jun;200(6):627.e1-10. doi: 10.1016/j.ajog.2009.01.015. PMID: 19306963.

12: Reinheimer TM. Barusiban suppresses oxytocin-induced preterm labour in non- human primates. BMC Pregnancy Childbirth. 2007 Jun 1;7 Suppl 1(Suppl 1):S15. doi: 10.1186/1471-2393-7-S1-S15. PMID: 17570159; PMCID: PMC1892056.

13: Rasmussen AD, Nelson JK, Chellman GJ, Golub M, McAnulty PA. Use of barusiban in a novel study design for evaluation of tocolytic agents in pregnant and neonatal monkeys, including behavioural and immunological endpoints. Reprod Toxicol. 2007 Jun;23(4):471-9. doi: 10.1016/j.reprotox.2006.12.007. Epub 2007 Jan 14. PMID: 17337159.

14: Reinheimer TM, Chellman GJ, Resendez JC, Meyer JK, Bee WH. Barusiban, an effective long-term treatment of oxytocin-induced preterm labor in nonhuman primates. Biol Reprod. 2006 Nov;75(5):809-14. doi: 10.1095/biolreprod.106.053637. Epub 2006 Aug 16. PMID: 16914691.

15: Gimpl G, Postina R, Fahrenholz F, Reinheimer T. Binding domains of the oxytocin receptor for the selective oxytocin receptor antagonist barusiban in comparison to the agonists oxytocin and carbetocin. Eur J Pharmacol. 2005 Mar 7;510(1-2):9-16. doi: 10.1016/j.ejphar.2005.01.010. PMID: 15740719.

16: Reinheimer TM, Bee WH, Resendez JC, Meyer JK, Haluska GJ, Chellman GJ. Barusiban, a new highly potent and long-acting oxytocin antagonist: pharmacokinetic and pharmacodynamic comparison with atosiban in a cynomolgus monkey model of preterm labor. J Clin Endocrinol Metab. 2005 Apr;90(4):2275-81. doi: 10.1210/jc.2004-2120. Epub 2005 Jan 25. PMID: 15671092.

17: Pierzynski P, Lemancewicz A, Reinheimer T, Akerlund M, Laudanski T. Inhibitory effect of barusiban and atosiban on oxytocin-induced contractions of myometrium from preterm and term pregnant women. J Soc Gynecol Investig. 2004 Sep;11(6):384-7. doi: 10.1016/j.jsgi.2004.02.008. PMID: 15350251.