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

MedKoo CAT#: 205912

CAS#: 441798-33-0

Description: Macitentan (trade name Opsumit) is an endothelin receptor antagonist (ERA) approved for the treatment of pulmonary arterial hypertension (PAH). The other two ERAs marketed as of 2014 are bosentan and ambrisentan. Macitentan is a dual ERA, meaning that it acts as an antagonist of two endothelin (ET) receptor subtypes, ETA and ETB. However, macitentan has a 50-fold increased selectivity for the ETA subtype compared to the ETB subtype. The drug received approval from the U.S. Food and Drug Administration (FDA) on October 13, 2013.


Price and Availability

Size
Price

1g
USD 650
10g
USD 2650
100g
USD 5850
Size
Price

2g
USD 950
25g
USD 3450
200g
USD 7950
Size
Price

5g
USD 1450
50g
USD 4250
500g
USD 14650

Macitentan, purity > 98%, is in stock. Current shipping out time is about 2 weeks after order is received. CoA, QC data and MSDS documents are available in one week after order is received. Delivery time: overnight (USA/Canada); 3-5 days (worldwide). Shipping fee: from $30.00 (USA); from $45.00 (Canada); from $70.00 (international).


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 205912
Name: Macitentan
CAS#: 441798-33-0
Chemical Formula: C19H20Br2N6O4S
Exact Mass: 585.96335
Molecular Weight: 588.27
Elemental Analysis: C, 38.79; H, 3.43; Br, 27.17; N, 14.29; O, 10.88; S, 5.45


Synonym: ACT-064992; ACT 064992; ACT064992; Macitentan; brand name: Opsumit.

IUPAC/Chemical Name: N-[5-(4-bromophenyl)-6-{2-[(5-bromopyrimidin-2-yl)oxy]ethoxy}pyrimidin-4-yl]-N'- propylsulfamide

InChi Key: JGCMEBMXRHSZKX-UHFFFAOYSA-N

InChi Code: InChI=1S/C19H20Br2N6O4S/c1-2-7-26-32(28,29)27-17-16(13-3-5-14(20)6-4-13)18(25-12-24-17)30-8-9-31-19-22-10-15(21)11-23-19/h3-6,10-12,26H,2,7-9H2,1H3,(H,24,25,27)

SMILES Code: O=S(NCCC)(NC1=NC=NC(OCCOC2=NC=C(Br)C=N2)=C1C3=CC=C(Br)C=C3)=O


Technical Data

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, not in water

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).

Harmonized System Code:
293490


Additional Information

  
 
 
 


References

1: Shinohara T, Sawada H, Otsuki S, Yodoya N, Kato T, Ohashi H, Zhang E, Saitoh S, Shimpo H, Maruyama K, Komada Y, Mitani Y. Macitentan reverses early obstructive pulmonary vasculopathy in rats: Early intervention in overcoming the survivin-mediated resistance to apoptosis. Am J Physiol Lung Cell Mol Physiol. 2014 Dec 24:ajplung.00129.2014. doi: 10.1152/ajplung.00129.2014. [Epub ahead of print] PubMed PMID: 25539851.

2: Kholdani CA, Fares WH, Trow TK. Macitentan for the treatment of pulmonary arterial hypertension. Vasc Health Risk Manag. 2014 Nov 25;10:665-73. doi: 10.2147/VHRM.S33904. eCollection 2014. PubMed PMID: 25473292; PubMed Central PMCID: PMC4251661.

3: Channick RN, Delcroix M, Ghofrani HA, Hunsche E, Jansa P, Le Brun FO, Mehta S, Pulido T, Rubin LJ, Sastry BK, Simonneau G, Sitbon O, Souza R, Torbicki A, Galiè N. Effect of Macitentan on Hospitalizations: Results From the SERAPHIN Trial (Study with an Endothelin Receptor Antagonist in Pulmonary arterial Hypertension to Improve cliNical outcome). JACC Heart Fail. 2014 Nov 11. pii: S2213-1779(14)00384-9. doi: 10.1016/j.jchf.2014.07.013. [Epub ahead of print] PubMed PMID: 25457902.

4: Tullos NA, Stewart NJ, Davidovich R, Chade AR. Chronic blockade of endothelin A and B receptors using macitentan in experimental renovascular disease. Nephrol Dial Transplant. 2014 Nov 21. pii: gfu361. [Epub ahead of print] PubMed PMID: 25438341.

5: Said K. Macitentan in pulmonary arterial hypertension: The SERAPHIN trial. Glob Cardiol Sci Pract. 2014 Jun 18;2014(2):26-30. doi: 10.5339/gcsp.2014.20. eCollection 2014. PubMed PMID: 25405173; PubMed Central PMCID: PMC4220429.

6: Sood N. Macitentan for the treatment of pulmonary arterial hypertension. Expert Opin Pharmacother. 2014 Dec;15(18):2733-9. doi: 10.1517/14656566.2014.980403. Epub 2014 Nov 11. PubMed PMID: 25385427.

7: Temple IP, Monfredi O, Quigley G, Schneider H, Zi M, Cartwright EJ, Boyett MR, Mahadevan VS, Hart G. Macitentan treatment retards the progression of established pulmonary arterial hypertension in an animal model. Int J Cardiol. 2014 Dec 15;177(2):423-8. doi: 10.1016/j.ijcard.2014.09.005. Epub 2014 Oct 11. PubMed PMID: 25305681; PubMed Central PMCID: PMC4251701.

8: Gatfield J, Mueller Grandjean C, Bur D, Bolli MH, Nayler O. Distinct ETA receptor binding mode of macitentan as determined by site directed mutagenesis. PLoS One. 2014 Sep 16;9(9):e107809. doi: 10.1371/journal.pone.0107809. eCollection 2014. PubMed PMID: 25226600; PubMed Central PMCID: PMC4166607.

9: Kunita-Takanezawa M, Abe K, Hirooka Y, Kuwabara Y, Hirano K, Oka M, Sunagawa K. Novel dual endothelin receptor antagonist macitentan reverses severe pulmonary arterial hypertension in rats. J Cardiovasc Pharmacol. 2014 Nov;64(5):473-80. doi: 10.1097/FJC.0000000000000141. PubMed PMID: 25084082.

10: Dhillon S. Macitentan: a review of its use in patients with pulmonary arterial hypertension. Drugs. 2014 Sep;74(13):1495-507. doi: 10.1007/s40265-014-0266-9. PubMed PMID: 25060980.

11: DuBrock HM, Channick RN. Macitentan for the treatment of pulmonary arterial hypertension. Expert Rev Respir Med. 2014 Aug;8(4):393-9. doi: 10.1586/17476348.2014.937708. Epub 2014 Jul 6. PubMed PMID: 24998329.

12: Spikes L, Williamson T, Satterwhite L. Macitentan for the treatment of pulmonary arterial hypertension. Drugs Today (Barc). 2014 Jun;50(6):401-6. doi: 10.1358/dot.2014.50.6.2146837. Review. PubMed PMID: 24983588.

13: Sidharta PN, van Giersbergen PL, Wolzt M, Dingemanse J. Investigation of mutual pharmacokinetic interactions between macitentan, a novel endothelin receptor antagonist, and sildenafil in healthy subjects. Br J Clin Pharmacol. 2014 Nov;78(5):1035-42. doi: 10.1111/bcp.12447. PubMed PMID: 24962473; PubMed Central PMCID: PMC4243877.

14: Ahn LY, Kim SE, Yi S, Dingemanse J, Lim KS, Jang IJ, Yu KS. Pharmacokinetic-pharmacodynamic relationships of macitentan, a new endothelin receptor antagonist, after multiple dosing in healthy Korean subjects. Am J Cardiovasc Drugs. 2014 Oct;14(5):377-85. doi: 10.1007/s40256-014-0081-4. PubMed PMID: 24906252.

15: Sidharta PN, Dietrich H, Dingemanse J. Investigation of the effect of macitentan on the pharmacokinetics and pharmacodynamics of warfarin in healthy male subjects. Clin Drug Investig. 2014 Aug;34(8):545-52. doi: 10.1007/s40261-014-0207-0. PubMed PMID: 24861134.

16: Clarke M, Walter C, Agarwal R, Kanwar M, Benza RL. Macitentan (Opsumit) for the treatment of pulmonary arterial hypertension. Expert Rev Clin Pharmacol. 2014 Jul;7(4):415-21. doi: 10.1586/17512433.2014.919849. Epub 2014 May 22. PubMed PMID: 24851934.

17: Lindegger N, Sidharta PN, Reseski K, Dingemanse J. Macitentan, a dual endothelin receptor antagonist for the treatment of pulmonary arterial hypertension, does not affect cardiac repolarization in healthy subjects. Pulm Pharmacol Ther. 2014 Oct;29(1):41-8. doi: 10.1016/j.pupt.2014.04.007. Epub 2014 May 9. PubMed PMID: 24813561.

18: Treiber A, Äänismaa P, de Kanter R, Delahaye S, Treher M, Hess P, Sidharta P. Macitentan does not interfere with hepatic bile salt transport. J Pharmacol Exp Ther. 2014 Jul;350(1):130-43. doi: 10.1124/jpet.114.214106. Epub 2014 Apr 25. PubMed PMID: 24769543.

19: Steriade A, Seferian A, Jaïs X, Savale L, Jutant EM, Parent F, Sitbon O, Humbert M, Simonneau G, Montani D. The potential for macitentan, a new dual endothelin receptor antagonist, in the treatment of pulmonary arterial hypertension. Ther Adv Respir Dis. 2014 Apr 11;8(3):84-92. [Epub ahead of print] Review. PubMed PMID: 24728960.

20: Macitentan (Opsumit) for pulmonary arterial hypertension. Med Lett Drugs Ther. 2014 Feb 17;56(1436):15-6. PubMed PMID: 24663031.