Tacrolimus hydrate | CAS#109581-93-3 | Immunosuppressive

MedKoo Cat#: 592996 | Name: Tacrolimus hydrate

Description:

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

Tacrolimus, also known as FK-506, is an immunosuppressive drug used mainly after allogeneic organ transplant to reduce the activity of the patient's immune system and to lower the risk of organ rejection. It is also used in a topical preparation in the treatment of atopic dermatitis (eczema), severe refractory uveitis after bone marrow transplants, exacerbations of minimal change disease, TH2-mediated diseases such as Kimura's disease, and the skin condition vitiligo. FK-506 is a macrolide isolated from the fungus Streptomyces tsukubaensis.

Chemical Structure

Tacrolimus hydrate

CAS#109581-93-3 (hydrate)

Theoretical Analysis

MedKoo Cat#: 592996

Name: Tacrolimus hydrate

CAS#: 109581-93-3 (hydrate)

Chemical Formula: C44H71NO13

Exact Mass: 821.4925

Molecular Weight: 822.05

Elemental Analysis: C, 64.29; H, 8.71; N, 1.70; O, 25.30

Price and Availability

Size	Price	Availability
50mg	USD 90.00	Ready to ship
100mg	USD 150.00	Ready to ship
200mg	USD 250.00	Ready to ship
500mg	USD 450.00	Ready to ship
1g	USD 750.00	Ready to ship
2g	USD 1,350.00	Ready to ship
5g	USD 2,650.00	Ready to ship

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Related CAS #

109581-93-3 (hydrate) 104987-11-3 (anhydrous)

Synonym

FR 900506; FR900506; LCP-Tacro; Prograf; FK 506; FK-506; FK506; Protopic; Tacrolimus; Tacrolimus hydrate; Tsukubaenolide hydrate; Tacrolimus monohydrate

IUPAC/Chemical Name

15,19-Epoxy-3H-pyrido(2,1-c)(1,4)oxaazacyclotricosine-1,7,20,21(4H,23H)-tetrone, 5,6,8,11,12,13,14,15,16,17,18,19,24,25,26,26a-hexadecahydro-5,19-dihydroxy-3-(2-(4-hydroxy-3-methoxycyclohexyl)-1-methylethenyl)-14,16-dimethoxy-4,10,12,18-tetramethyl-8-(2-propenyl)-, monohydrate, (3S-(3R*,(E(1S*,3S*,4S*)),4S*,5R*,8S*,9E,12R*,14R*,15S*,16R*,18S*,19S*,26aR*))-

InChi Key

NWJQLQGQZSIBAF-MLAUYUEBSA-N

InChi Code

InChI=1S/C44H69NO12.H2O/c1-10-13-31-19-25(2)18-26(3)20-37(54-8)40-38(55-9)22-28(5)44(52,57-40)41(49)42(50)45-17-12-11-14-32(45)43(51)56-39(29(6)34(47)24-35(31)48)27(4)21-30-15-16-33(46)36(23-30)53-7;/h10,19,21,26,28-34,36-40,46-47,52H,1,11-18,20,22-24H2,2-9H3;1H2/b25-19+,27-21+;/t26-,28+,29+,30-,31+,32-,33+,34-,36+,37-,38-,39+,40+,44+;/m0./s1

SMILES Code

CO[C@@H]1C[C@H](/C=C([C@H]2OC([C@@H]3CCCCN3C(C([C@@]4(O[C@@H]([C@@H](OC)C[C@H]4C)[C@@H](OC)C[C@H](C/C(C)=C/[C@H](C(C[C@@H]([C@H]2C)O)=O)CC=C)C)O)=O)=O)=O)\C)CC[C@H]1O.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

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

Certificate of Analysis

View CoA: current batch, Lot#A21T08K05

QC Data

View QC data: current batch, Lot#A21T08K05

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

Biological target:

Tacrolimus inhibits calcineurin phosphatase, which inhibits T-lymphocyte signal transduction and IL-2 transcription.

In vitro activity:

Scanning electron microscopy revealed mineralized bone matrix in the cell clusters, which was identical to that of living bone. High levels of alkaline phosphatase (ALP), indicating osteoblastic activity, and high levels of osteocalcin (Oc) and calcium were found in the mature bone matrix of the cultures. There was significantly increased expression of mRNAs for ALP and Oc. These results indicate that the cultures contained both bone matrix and high osteoblastic activity, suggesting that FK506 induces ossification. Reference: Yoshikawa T, Nakajima H, Uemura T, Kasai T, Enomoto Y, Tamura T, Nonomura A, Takakura Y. In vitro bone formation induced by immunosuppressive agent tacrolimus hydrate (FK506). Tissue Eng. 2005 Mar-Apr;11(3-4):609-17. doi: 10.1089/ten.2005.11.609. PMID: 15869437.

In vivo activity:

P-gp function was estimated by transporter activity that was inferred from a decrease in fluorescent P-gp substrate Rhodamine 123 (Rh123) and its inhibition by cyclosporine A (CsA). The P-gp efflux function in MG (FK+) patients assessed by the Kolmogorov-Smirnov (KS) statistic D was lower than in the healthy subjects (p=0.0084). However, PBMC sensitivity to FK506 in MG (FK+) patients was significantly higher compared to that of the healthy subjects (p=0.02). There was a significant correlation between the Rh123 efflux activity and PBMC sensitivity to FK506 in vitro (p=0.011). The data raise the possibility that FK506 treatment attenuated P-gp function in the PBMCs of the MG patients. Reference: Tanaka S, Hirano T, Saito T, Wakata N, Oka K. P-glycoprotein function in peripheral blood mononuclear cells of myasthenia gravis patients treated with tacrolimus. Biol Pharm Bull. 2007 Feb;30(2):291-6. doi: 10.1248/bpb.30.291. PMID: 17268068.

	Solvent	mg/mL	mM
Solubility
	DMSO	20.0	24.33

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 822.05 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:

Yoshikawa T, Nakajima H, Uemura T, Kasai T, Enomoto Y, Tamura T, Nonomura A, Takakura Y. In vitro bone formation induced by immunosuppressive agent tacrolimus hydrate (FK506). Tissue Eng. 2005 Mar-Apr;11(3-4):609-17. doi: 10.1089/ten.2005.11.609. PMID: 15869437.

In vitro protocol:

In vivo protocol:

Tanaka S, Hirano T, Saito T, Wakata N, Oka K. P-glycoprotein function in peripheral blood mononuclear cells of myasthenia gravis patients treated with tacrolimus. Biol Pharm Bull. 2007 Feb;30(2):291-6. doi: 10.1248/bpb.30.291. PMID: 17268068.

1: Yamamoto S, Nagaki Y, Fukuo Y, Hirata H. Cross-species transplantation of photoreceptors with tacrolimus hydrate (FK506) treatment. Jpn J Ophthalmol. 1995;39(4):334-9. PMID: 8926639. 2: Hayashi K, Nagamatsu T, Ito M, Suzuki Y. Suppression of experimental crescentic-type anti-glomerular basement membrane (GBM) nephritis by FK506 (tacrolimus hydrate) in rats. Jpn J Pharmacol. 1996 Jan;70(1):43-54. doi: 10.1254/jjp.70.43. PMID: 8822088. 3: Sempuku T, Ohgushi H, Okumura M, Tamai S. Osteogenic potential of allogeneic rat marrow cells in porous hydroxyapatite ceramics: a histological study. J Orthop Res. 1996 Nov;14(6):907-13. doi: 10.1002/jor.1100140610. PMID: 8982133. 4: Wu J, Furusawa S, Nakano S, Takahashi M, Chiba H, Takayanagi M, Takayanagi Y, Sasaki K. Reversal of multidrug resistance by tacrolimus hydrate. Methods Find Exp Clin Pharmacol. 1996 Dec;18(10):651-8. PMID: 9121220. 5: Yoshimoto T, Yagi K, Inoue M, Okamura T, Yasui M, Cyayama K, Nakano T, Tsuchiya H, Kawa K. [Leukoencephalopathy probably caused by tacrolimus hydrate after stem cell transplantation in a girl with MDS 7 monosomy]. Rinsho Ketsueki. 1997 Jul;38(7):616-21. Japanese. PMID: 9267167. 6: Tanaka H, Nakahara K, Hatanaka H, Inamura N, Kuroda A. [Discovery and development of a novel immunosuppressant, tacrolimus hydrate]. Yakugaku Zasshi. 1997 Aug;117(8):542-54. Japanese. doi: 10.1248/yakushi1947.117.8_542. PMID: 9306728. 7: Hiroi J, Sengoku T, Morita K, Kishi S, Sato S, Ogawa T, Tsudzuki M, Matsuda H, Wada A, Esaki K. Effect of tacrolimus hydrate (FK506) ointment on spontaneous dermatitis in NC/Nga mice. Jpn J Pharmacol. 1998 Feb;76(2):175-83. doi: 10.1254/jjp.76.175. PMID: 9541280. 8: Tamura F, Masuhara A, Sakaida I, Fukumoto E, Nakamura T, Okita K. FK506 promotes liver regeneration by suppressing natural killer cell activity. J Gastroenterol Hepatol. 1998 Jul;13(7):703-8. doi: 10.1111/j.1440-1746.1998.tb00717.x. PMID: 9715421. 9: Sengoku T, Morita K, Sakuma S, Motoyama Y, Goto T. Possible inhibitory mechanism of FK506 (tacrolimus hydrate) ointment for atopic dermatitis based on animal models. Eur J Pharmacol. 1999 Aug 27;379(2-3):183-9. doi: 10.1016/s0014-2999(99)00500-2. PMID: 10497905. 10: Matsuda J. [Tacrolimus hydrate (tacrolimus)]. Nihon Rinsho. 1999 Sep;57 Suppl:432-5. Japanese. PMID: 10543146. 11: Sengoku T, Kishi S, Sakuma S, Ohkubo Y, Goto T. FK506 inhibition of histamine release and cytokine production by mast cells and basophils. Int J Immunopharmacol. 2000 Mar;22(3):189-201. doi: 10.1016/s0192-0561(99)00076-4. PMID: 10685002. 12: Yoshizawa K, Nambu H, Yamamoto D, Yang J, Kiyozuka Y, Shikata N, Tsubura A. Time-specific occurrence of alopecia in neonatal C57BL mice treated with N-methyl-N-nitrosourea and the therapeutic efficacy of tacrolimus hydrate. Pathol Int. 2000 Mar;50(3):175-84. doi: 10.1046/j.1440-1827.2000.01021.x. PMID: 10792780. 13: Zaman AK. Effects of tacrolimus hydrate (FK-506) on the expression of tissue factor in THP-1 human monocyte cell line. Hokkaido Igaku Zasshi. 2000 May;75(3):179-86. PMID: 10884973. 14: Uchida K, Sakaida I, Hironaka K, Kayano K, Okita K. Preventive effect of FK 506 (tacrolimus hydrate) on experimentally induced acute liver injury in rats. Dig Dis Sci. 2000 Oct;45(10):1996-2001. doi: 10.1023/a:1005698818891. PMID: 11117573. 15: Sadahira Y, Kumori K, Mikami Y, Otsuki T, Manabe T, Aoyama K. Post- transplant malignant lymphoma with monoclonal immunoglobulin gene rearrangement and polyclonal Epstein-Barr virus episomes. J Clin Pathol. 2001 Nov;54(11):887-9. doi: 10.1136/jcp.54.11.887. PMID: 11684728; PMCID: PMC1731324. 16: Iguchi S, Nishi S, Shinbo J, Iino N, Kazama JJ, Shimada H, Ueno M, Saitou K, Tanigawa T, Takahashi K, Gejyo F. Intratubular calcification in a post-renal transplanted patient with secondary hyperparathyroidism. Clin Transplant. 2001;15 Suppl 5:51-4. doi: 10.1034/j.1399-0012.2001.0150s5051.x. PMID: 11791796. 17: Fujii Y, Takeuchi H, Tanaka K, Sakuma S, Ohkubo Y, Mutoh S. Effects of FK506 (tacrolimus hydrate) on chronic oxazolone-induced dermatitis in rats. Eur J Pharmacol. 2002 Dec 5;456(1-3):115-21. doi: 10.1016/s0014-2999(02)02554-2. PMID: 12450577. 18: Wakata N, Saito T, Tanaka S, Hirano T, Oka K. Tacrolimus hydrate (FK506): therapeutic effects and selection of responders in the treatment of myasthenia gravis. Clin Neurol Neurosurg. 2003 Dec;106(1):5-8. doi: 10.1016/s0303-8467(03)00046-5. PMID: 14643908. 19: Matsuda J. [Tacrolimus hydrate (tacrolimus)]. Nihon Rinsho. 2004 Dec;62 Suppl 12:465-8. Japanese. PMID: 15658364. 20: Yoshikawa T, Nakajima H, Uemura T, Kasai T, Enomoto Y, Tamura T, Nonomura A, Takakura Y. In vitro bone formation induced by immunosuppressive agent tacrolimus hydrate (FK506). Tissue Eng. 2005 Mar-Apr;11(3-4):609-17. doi: 10.1089/ten.2005.11.609. PMID: 15869437.