Atosiban | CAS#90779-69-4 | vasopressin antagonist

MedKoo Cat#: 593038 | Name: Atosiban

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Description:

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

Atosiban, also known as ORF 22164, RWJ 22164, is an inhibitor of the hormones oxytocin and vasopressin. It is used as an intravenous medication as a labour repressant (tocolytic) to halt premature labor. Although initial studies suggested it could be used as a nasal spray and hence would not require hospital admission, it is not used in that form. It was developed by Ferring Pharmaceuticals in Sweden and first reported in the literature in 1985. Originally marketed by Ferring Pharmaceuticals, it is licensed in proprietary and generic forms for the delay of imminent pre-term birth in pregnant adult women.

Chemical Structure

Atosiban

CAS#90779-69-4 (free base)

Theoretical Analysis

MedKoo Cat#: 593038

Name: Atosiban

CAS#: 90779-69-4 (free base)

Chemical Formula: C43H67N11O12S2

Exact Mass: 993.4412

Molecular Weight: 994.19

Elemental Analysis: C, 51.95; H, 6.79; N, 15.50; O, 19.31; S, 6.45

Price and Availability

Size	Price	Availability	Quantity
5mg	USD 350.00	2 Weeks
10mg	USD 550.00	2 Weeks

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Related CAS #

914453-95-5 (acetate) 90779-69-4 (free base)

Synonym

Atosiban; RWJ 22164; RWJ-22164; RWJ22164; Antocin; ORF 22164; ORF-22164; ORF22164; Tractocile

IUPAC/Chemical Name

Oxytocin, 1-(3-mercaptopropanoic acid)-2-(O-ethyl-D-tyrosine)-4-L-threonine-8-L-ornithine-

InChi Key

VWXRQYYUEIYXCZ-OBIMUBPZSA-N

InChi Code

InChI=1S/C43H67N11O12S2/c1-5-23(3)35-41(63)53-36(24(4)55)42(64)50-29(20-32(45)56)38(60)51-30(43(65)54-17-8-10-31(54)40(62)49-27(9-7-16-44)37(59)47-21-33(46)57)22-68-67-18-15-34(58)48-28(39(61)52-35)19-25-11-13-26(14-12-25)66-6-2/h11-14,23-24,27-31,35-36,55H,5-10,15-22,44H2,1-4H3,(H2,45,56)(H2,46,57)(H,47,59)(H,48,58)(H,49,62)(H,50,64)(H,51,60)(H,52,61)(H,53,63)/t23-,24+,27-,28+,29-,30-,31-,35-,36-/m0/s1

SMILES Code

CCOc1ccc(C[C@H]2NC(CCSSC[C@@H](C(N3CCC[C@H]3C(N[C@H](C(NCC(N)=O)=O)CCCN)=O)=O)NC([C@@H](NC([C@H]([C@H](O)C)NC([C@H]([C@H](CC)C)NC2=O)=O)=O)CC(N)=O)=O)=O)cc1

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

2934.99.03.00

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Atosiban (RW22164; RWJ22164) is a nonapeptide competitive vasopressin/oxytocin receptor antagonist.

In vitro activity:

Instead incubation of amnion cells with Atosiban alone resulted in activation of NF-κB p65, ERK1/2, and p38 and downstream expression of COX-2 and p-cPLA2 to a similar degree as seen with OT treatment (Fig 1). This study therefore examined the effect of Atosiban on the expression of down-stream NF-κB regulated genes. As demonstrated at the protein level, treatment of amniotic cells with Atosiban alone increased mRNA expression of COX-2 (Fig 2A) as well as IL-6 and CCL5 (Fig. 2B–C). Atosiban treatment also led to increased excretion of prostaglandin (PGE2) and cytokines (IL-6 and CCL5) in cell supernatant as assessed by ELISA (Fig. 2D–F). Reference: Mol Cell Endocrinol. 2016 Jan 15;420:11-23. https://pubmed.ncbi.nlm.nih.gov/26586210/

In vivo activity:

However, compared to saline treatment, the antinociceptive effect was significantly reduced in the atosiban treated females during both intromissions (t = 3.5; df = 14, p < 0.01) and ejaculations (t = 5.1; df = 14, p < 0.01) (Fig. 1A). Thus, the antinociceptive effect induced by mounts (t = −3.2; df = 14, p < 0.05) intromissions (t = −3.5; df = 14, p < 0.01) and ejaculations (t = −5.1; df = 14, p < 0.01) was significantly reduced in atosiban-treated females, compared to saline controls (Fig. 1B). Animals that received icv saline displayed significantly reduced vocalizations in response to intromissions (t = 14.7; df = 14, p < 0.01) and ejaculations (t = 18.8; df = 14, p < 0.01), compared to their baseline response. However, in females that received icv atosiban, the vocalizations in response to intromissions and ejaculations did not differ significantly from the number of their baseline vocalization responses. Thus, the antinociceptive effect induced by intromissions (t = −6.9; df = 16, p < 0.01) and ejaculations (t = −5.6; df = 16, p < 0.01) was significantly reduced in atosiban-treated females, compared to saline controls (Fig. 1C). Reference: Horm Behav. 2019 Jan;107:76-79. https://pubmed.ncbi.nlm.nih.gov/30529271/

	Solvent	mg/mL	mM
Solubility
	DMSO	15.3	15.43
	DMF	30.0	30.18
	Ethanol	5.0	5.03
	PBS (pH 7.2)	5.0	5.03
	Water	16.7	16.77

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 994.19 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.

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:

1. Kim SH, Riaposova L, Ahmed H, Pohl O, Chollet A, Gotteland JP, Hanyaloglu A, Bennett PR, Terzidou V. Oxytocin Receptor Antagonists, Atosiban and Nolasiban, Inhibit Prostaglandin F2α-induced Contractions and Inflammatory Responses in Human Myometrium. Sci Rep. 2019 Apr 8;9(1):5792. doi: 10.1038/s41598-019-42181-2. PMID: 30962532; PMCID: PMC6453954. 2. Kim SH, MacIntyre DA, Hanyaloglu AC, Blanks AM, Thornton S, Bennett PR, Terzidou V. The oxytocin receptor antagonist, Atosiban, activates pro-inflammatory pathways in human amnion via G(αi) signalling. Mol Cell Endocrinol. 2016 Jan 15;420:11-23. doi: 10.1016/j.mce.2015.11.012. Epub 2015 Nov 14. PMID: 26586210. 3. Gómora-Arrati P, Gonzalez-Flores O, Galicia-Aguas YL, Hoffman KL, Komisaruk B. Copulation-induced antinociception in female rats is blocked by atosiban, an oxytocin receptor antagonist. Horm Behav. 2019 Jan;107:76-79. doi: 10.1016/j.yhbeh.2018.12.001. Epub 2018 Dec 18. PMID: 30529271. 4. Simsek Y, Celik O, Karaer A, Gul M, Yılmaz E, Koc O, Colak C, Zengin S, Aydin NE. Therapeutic efficiency of Atosiban, an oxytocin receptor blocking agent in the treatment of experimental endometriosis. Arch Gynecol Obstet. 2012 Sep;286(3):777-83. doi: 10.1007/s00404-012-2390-7. Epub 2012 May 31. PMID: 22648446.

In vitro protocol:

In vivo protocol:

1. Gómora-Arrati P, Gonzalez-Flores O, Galicia-Aguas YL, Hoffman KL, Komisaruk B. Copulation-induced antinociception in female rats is blocked by atosiban, an oxytocin receptor antagonist. Horm Behav. 2019 Jan;107:76-79. doi: 10.1016/j.yhbeh.2018.12.001. Epub 2018 Dec 18. PMID: 30529271. 2. Simsek Y, Celik O, Karaer A, Gul M, Yılmaz E, Koc O, Colak C, Zengin S, Aydin NE. Therapeutic efficiency of Atosiban, an oxytocin receptor blocking agent in the treatment of experimental endometriosis. Arch Gynecol Obstet. 2012 Sep;286(3):777-83. doi: 10.1007/s00404-012-2390-7. Epub 2012 May 31. PMID: 22648446.

1: Xu YJ, Ran LM, Zhai SS, Luo XH, Zhang YY, Zhou ZY, Liu YH, Ren LD, Hong T, Liu R. Evaluation of the efficacy of atosiban in pregnant women with threatened preterm labor associated with assisted reproductive technology. Eur Rev Med Pharmacol Sci. 2016 May;20(9):1881-7. PubMed PMID: 27212183. 2: He Y, Wu H, He X, Xing Q, Zhou P, Cao Y, Wei Z. Application of atosiban in frozen-thawed cycle patients with different times of embryo transfers. Gynecol Endocrinol. 2016 May 5:1-5. [Epub ahead of print] PubMed PMID: 27147474. 3: He Y, Wu H, He X, Xing Q, Zhou P, Cao Y, Wei Z. Administration of atosiban in patients with endometriosis undergoing frozen-thawed embryo transfer: a prospective, randomized study. Fertil Steril. 2016 Apr 30. pii: S0015-0282(16)61111-1. doi: 10.1016/j.fertnstert.2016.04.019. [Epub ahead of print] PubMed PMID: 27143518. 4: Weissman A, Tobia RS, Burke YZ, Maxymovski O, Drugan A. The effects of oxytocin and atosiban on the modulation of heart rate in pregnant women. J Matern Fetal Neonatal Med. 2016 Apr 19:1-5. [Epub ahead of print] PubMed PMID: 27030149. 5: van Vliet EO, Nijman TA, Schuit E, Heida KY, Opmeer BC, Kok M, Gyselaers W, Porath MM, Woiski M, Bax CJ, Bloemenkamp KW, Scheepers HC, Jacquemyn Y, Beek EV, Duvekot JJ, Franssen MT, Papatsonis DN, Kok JH, van der Post JA, Franx A, Mol BW, Oudijk MA. Nifedipine versus atosiban for threatened preterm birth (APOSTEL III): a multicentre, randomised controlled trial. Lancet. 2016 Mar 1. pii: S0140-6736(16)00548-1. doi: 10.1016/S0140-6736(16)00548-1. [Epub ahead of print] PubMed PMID: 26944026. 6: Kim SH, MacIntyre DA, Hanyaloglu AC, Blanks AM, Thornton S, Bennett PR, Terzidou V. The oxytocin receptor antagonist, Atosiban, activates pro-inflammatory pathways in human amnion via G(αi) signalling. Mol Cell Endocrinol. 2016 Jan 15;420:11-23. doi: 10.1016/j.mce.2015.11.012. Epub 2015 Nov 14. PubMed PMID: 26586210. 7: Bartekova M, Barancik M, Pokusa M, Prokopova B, Radosinska J, Rusnak A, Breier A, Jezova D. Molecular changes induced by repeated restraint stress in the heart: the effect of oxytocin receptor antagonist atosiban. Can J Physiol Pharmacol. 2015 Sep;93(9):827-34. doi: 10.1139/cjpp-2015-0096. Epub 2015 Jun 24. PubMed PMID: 26323039. 8: Babic S, Pokusa M, Danevova V, Ding ST, Jezova D. Effects of atosiban on stress-related neuroendocrine factors. J Endocrinol. 2015 Apr;225(1):9-17. doi: 10.1530/JOE-14-0560. Epub 2015 Jan 21. PubMed PMID: 25609735. 9: Ng EH, Li RH, Chen L, Lan VT, Tuong HM, Quan S. A randomized double blind comparison of atosiban in patients undergoing IVF treatment. Hum Reprod. 2014 Dec;29(12):2687-94. doi: 10.1093/humrep/deu263. Epub 2014 Oct 21. PubMed PMID: 25336707. 10: Driul L, Londero AP, Adorati-Menegato A, Vogrig E, Bertozzi S, Fachechi G, Forzano L, Cacciaguerra G, Perin E, Miceli A, Marchesoni D. Therapy side-effects and predictive factors for preterm delivery in patients undergoing tocolysis with atosiban or ritodrine for threatened preterm labour. J Obstet Gynaecol. 2014 Nov;34(8):684-9. doi: 10.3109/01443615.2014.930094. Epub 2014 Jun 24. PubMed PMID: 24959721. 11: Nanetti L, Raffaelli F, Giulietti A, Sforza G, Raffaele Giannubilo S, Ciavattini A, Tranquilli AL, Mazzanti L, Vignini A. Oxytocin, its antagonist Atosiban, and preterm labor: a role for placental nitric oxide. J Matern Fetal Neonatal Med. 2015 Mar;28(5):611-6. doi: 10.3109/14767058.2014.927859. Epub 2014 Jul 11. PubMed PMID: 24920283. 12: van Vliet EO, Schuit E, Heida KY, Opmeer BC, Kok M, Gyselaers W, Porath MM, Woiski M, Bax CJ, Bloemenkamp KW, Scheepers HC, Jaquemyn Y, van Beek E, Duvekot HJ, Franssen MT, Bijvank BN, Kok JH, Franx A, Mol BW, Oudijk MA. Nifedipine versus atosiban in the treatment of threatened preterm labour (Assessment of Perinatal Outcome after Specific Tocolysis in Early Labour: APOSTEL III-Trial). BMC Pregnancy Childbirth. 2014 Mar 3;14:93. doi: 10.1186/1471-2393-14-93. PubMed PMID: 24589124; PubMed Central PMCID: PMC3944539. 13: Grzesiak M, Ahmed RB, Wilczynski J. Doppler evaluation of blood flow in fetal inferior vena cava during 48-hours Atosiban administration in spontaneous preterm labor. Neuro Endocrinol Lett. 2013;34(8):787-91. PubMed PMID: 24522017. 14: Grzesiak M, Wilczynski J. Preliminary report of 48-hours Atosiban administration in spontaneous preterm labor - Doppler blood flow assessment of placental and fetal circulation. Neuro Endocrinol Lett. 2013;34(7):681-6. PubMed PMID: 24464012. 15: Hadar E, Melamed N, Aviram A, Raban O, Saltzer L, Hiersch L, Yogev Y. Effect of an oxytocin receptor antagonist (atosiban) on uterine electrical activity. Am J Obstet Gynecol. 2013 Oct;209(4):384.e1-7. doi: 10.1016/j.ajog.2013.05.053. Epub 2013 Jun 15. PubMed PMID: 23727522. 16: Seinen LH, Simons SO, van der Drift MA, van Dillen J, Vandenbussche FP, Lotgering FK. [Maternal pulmonary oedema due to the use of atosiban in cases of multiple gestation]. Ned Tijdschr Geneeskd. 2013;157(1):A5316. Dutch. PubMed PMID: 23298725. 17: Saleh SS, Al-Ramahi MQ, Al Kazaleh FA. Atosiban and nifedipine in the suppression of pre-term labour: a comparative study. J Obstet Gynaecol. 2013 Jan;33(1):43-5. doi: 10.3109/01443615.2012.721822. PubMed PMID: 23259877. 18: Cheung CS, Li TK, Lee CP. Maternal atrial fibrillation after sequential use of nifedipine and atosiban for treatment of preterm labor: case report. Eur J Obstet Gynecol Reprod Biol. 2013 Feb;166(2):229. doi: 10.1016/j.ejogrb.2012.10.027. Epub 2012 Nov 20. PubMed PMID: 23182072. 19: Salim R, Garmi G, Nachum Z, Zafran N, Baram S, Shalev E. Nifedipine compared with atosiban for treating preterm labor: a randomized controlled trial. Obstet Gynecol. 2012 Dec;120(6):1323-31. doi: http://10.1097/AOG.0b013e3182755dff. PubMed PMID: 23168756. 20: Lan VT, Khang VN, Nhu GH, Tuong HM. Atosiban improves implantation and pregnancy rates in patients with repeated implantation failure. Reprod Biomed Online. 2012 Sep;25(3):254-60. doi: 10.1016/j.rbmo.2012.05.014. Epub 2012 Jun 16. PubMed PMID: 22818095.

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MedKoo CAT#: 532043

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