TAK-044

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

MedKoo CAT#: 526688

CAS#: 157380-72-8

Description: TAK-044 is an Endothelin receptor antagonist. TAK-044 arrests and reverses the development of carbon tetrachloride induced cirrhosis in rats. TAK-044 showed protective effect on neuronal cell viability in in vitro oxygen-glucose deprivation model of stroke.


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TAK-044 is not in stock, but may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 526688
Name: TAK-044
CAS#: 157380-72-8
Chemical Formula: C45H51N9Na2O11S
Exact Mass:
Molecular Weight: 971.9945
Elemental Analysis: C, 55.61; H, 5.29; N, 12.97; Na, 4.73; O, 18.11; S, 3.30


Synonym: TAK-044, TAK 044, TAK044

IUPAC/Chemical Name: sodium 2,2'-((2R,5R,8S,11S,14R,17R)-17-((1H-indol-3-yl)methyl)-14-isobutyl-3,6,9,12,15,18-hexaoxo-5-(2-oxo-2-(4-phenylpiperazin-1-yl)ethyl)-11-(thiophen-2-yl)-1,4,7,10,13,16-hexaazacyclooctadecane-2,8-diyl)diacetate

InChi Key: UWHBIISPHYTOGL-KGKYADQVSA-L

InChi Code: InChI=1S/C45H53N9O11S.2Na/c1-25(2)19-30-40(60)47-31(20-26-24-46-29-12-7-6-11-28(26)29)41(61)49-33(22-37(56)57)43(63)48-32(21-36(55)54-16-14-53(15-17-54)27-9-4-3-5-10-27)42(62)50-34(23-38(58)59)44(64)52-39(45(65)51-30)35-13-8-18-66-35;;/h3-13,18,24-25,30-34,39,46H,14-17,19-23H2,1-2H3,(H,47,60)(H,48,63)(H,49,61)(H,50,62)(H,51,65)(H,52,64)(H,56,57)(H,58,59);;/q;2*+1/p-2/t30-,31-,32-,33-,34+,39-;;/m1../s1

SMILES Code: O=C(N1CCN(C2=CC=CC=C2)CC1)C[C@H](C(N[C@@H](CC([O-])=O)C(N[C@H](C3=CC=CS3)C(N[C@H](CC(C)C)C(N[C@@H]4CC5=CNC6=C5C=CC=C6)=O)=O)=O)=O)NC([C@@H](CC([O-])=O)NC4=O)=O.[Na+].[Na+]


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


References

1: Briyal S, Gulati A, Gupta YK. Effect of combination of endothelin receptor antagonist (TAK-044) and aspirin in middle cerebral artery occlusion model of acute ischemic stroke in rats. Methods Find Exp Clin Pharmacol. 2007 May;29(4):257-63. PubMed PMID: 17609737.

2: Briyal S, Pant AB, Gupta YK. Protective effect of endothelin antagonist (TAK-044) on neuronal cell viability in in vitro oxygen-glucose deprivation model of stroke. Indian J Physiol Pharmacol. 2006 Apr-Jun;50(2):157-62. PubMed PMID: 17051735.

3: Behrend M. The endothelin receptor antagonist TAK-044 in the treatment of reperfusion injury in organ transplantation. Expert Opin Investig Drugs. 1999 Jul;8(7):1079-91. PubMed PMID: 15992108.

4: Gupta YK, Briyal S, Sharma U, Jagannathan NR, Gulati A. Effect of endothelin antagonist (TAK-044) on cerebral ischemic volume, oxidative stress markers and neurobehavioral parameters in the middle cerebral artery occlusion model of stroke in rats. Life Sci. 2005 May 20;77(1):15-27. PubMed PMID: 15848215.

5: Thirunavukkarasu C, Yang Y, Subbotin VM, Harvey SA, Fung J, Gandhi CR. Endothelin receptor antagonist TAK-044 arrests and reverses the development of carbon tetrachloride induced cirrhosis in rats. Gut. 2004 Jul;53(7):1010-9. PubMed PMID: 15194653; PubMed Central PMCID: PMC1774118.

6: Yomogida S, Maruya J, Norota I, Ishii K, Endoh M. Differential inhibition by TAK-044 of the inotropic effects of endothelin-1 and endothelin-3. Eur J Pharmacol. 2004 May 25;492(2-3):217-24. PubMed PMID: 15178368.

7: Maeshiba Y, Yamashita K, Tsukuda R, Yoshimura Y. Pharmacokinetic interaction between TAK-044, a new endothelin antagonist, and ciclosporin in rats. Arzneimittelforschung. 2002;52(9):664-8. PubMed PMID: 12404880.

8: Maeshiba Y, Takeuchi T, Kondo T, Yamashita K, Tsukuda R, Yoshimura Y. Disposition of TAK-044, a new endothelin antagonist, in rats and dogs. Arzneimittelforschung. 2002;52(8):587-92. PubMed PMID: 12236045.

9: Anselmi K, Subbotin VM, Nemoto E, Gandhi CR. Accelerated reversal of carbon tetrachloride-induced cirrhosis in rats by the endothelin receptor antagonist TAK-044. J Gastroenterol Hepatol. 2002 May;17(5):589-97. PubMed PMID: 12084034.

10: Kaneda T, Zhang ZW, Ogawa T, Otaki M, Saga T. Pretreatment of donors with endothelin receptor antagonist TAK-044 improves cardiac functional recovery following preservation with University of Wisconsin solution. Scand Cardiovasc J. 2002 Mar;36(2):105-7. PubMed PMID: 12028874.

11: Takeuchi T, Tagawa Y, Hagihara K, Maeshiba Y, Yamashita K, Tsukuda R, Yoshimura Y. Nonlinear pharmacokinetics of TAK-044, a new endothelin antagonist, in rats. Biopharm Drug Dispos. 2001 Sep;22(6):221-30. PubMed PMID: 11754038.

12: Sunose Y, Ohwada S, Takeyoshi I, Matsumoto K, Tsutsumi H, Tomizawa N, Kawate S, Morishita Y. Effects of endothelin receptor antagonist TAK-044 on small bowel autograft from a controlled non-heart-beating donor model. Surgery. 2001 Nov;130(5):819-25. PubMed PMID: 11685191.

13: Bergström G, Nyström HC, Jia J, Evans RG. Effects of the ET(A)/ET(B) antagonist, TAK-044, on blood pressure and renal excretory function after unclipping of conscious one-kidney-one-clip hypertensive rats. J Hypertens. 2001 Mar;19(3 Pt 2):659-65. PubMed PMID: 11327643.

14: Watanabe K, Ohta Y, Kouda T, Sekiguchi T, Sato S, Nakazawa M, Hasegawa G, Naito M, Fuse K, Ito M, Hirono S, Tanabe N, Hanawa H, Kato K, Kodama M, Aizawa Y. Acute effects of endothelin-1 and TAK-044 (ET(A) and ET(B) receptor antagonist) in rats with dilated cardiomyopathy. J Cardiovasc Pharmacol. 2000;36 Suppl 2:S49-54. PubMed PMID: 11206720.

15: Shaw MD, Vermeulen M, Murray GD, Pickard JD, Bell BA, Teasdale GM. Efficacy and safety of the endothelin, receptor antagonist TAK-044 in treating subarachnoid hemorrhage: a report by the Steering Committee on behalf of the UK/Netherlands/Eire TAK-044 Subarachnoid Haemorrhage Study Group. J Neurosurg. 2000 Dec;93(6):992-7. PubMed PMID: 11117873.

16: Naruse M, Tanabe A, Naruse K, Adachi C, Yoshimoto T, Seki T, Takagi S, Imaki T, Watanabe T, Takano K. Hemodynamic and biochemical effects of endothelin-A- and -B-receptor antagonist TAK-044 in stroke-prone spontaneously hypertensive rats. J Cardiovasc Pharmacol. 2000 Nov;36(5 Suppl 1):S334-6. PubMed PMID: 11078413.

17: Takaya Y, Yamanaka N, Oriyama T, Furukawa K, Tanaka T, Nakagaki I I, Sasaki S, Hori S, Okamoto E. In vivo subcellular elemental dynamics in liver graft: With special reference to effect of non-selective endothelin receptor antagonist, TAK-044, on the graft injury. Hepatol Res. 2000 Nov;18(3):171-183. PubMed PMID: 11058822.

18: Yoshida K, Kagebayashi Y, Kitauchi T, Kimura S, Yoneda T, Ozono S, Hirao Y, Watanabe T. Effect of endothelin receptor antagonist (TAK-044) on autotransplanted perfused kidneys in dogs. Urol Int. 2000;65(3):148-54. PubMed PMID: 11054033.

19: Watanabe T, Hayasi J, Isogai A, Shimizu S, Takara T, Asakura T, Moriya H, Kubota S, Yamaguchi S. Effects of the endothelin-1 receptor antagonist TAK-044 on pulmonary injury in discordant xenotransplantation. Transplant Proc. 2000 Aug;32(5):911-2. PubMed PMID: 10936270.

20: Takizawa T, Horikoshi E, Shen MH, Masaoka T, Takagi H, Yamamoto M, Kasai K, Arishima K. Effects of TAK-044, a nonselective endothelin receptor antagonist, on the spontaneous and indomethacin- or methylene blue-induced constriction of the ductus arteriosus in rats. J Vet Med Sci. 2000 May;62(5):505-9. PubMed PMID: 10852399.