Tacrolimus hydrate
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MedKoo CAT#: 592996

CAS#: 109581-93-3 (hydrate)

Description: 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

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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: 821.49
Molecular Weight: 822.050
Elemental Analysis: C, 64.29; H, 8.71; N, 1.70; O, 25.30

Price and Availability

Size Price Availability Quantity
50mg USD 90 Ready to ship
100mg USD 150 Ready to ship
200mg USD 250 Ready to ship
500mg USD 450 Ready to ship
1g USD 750 Ready to ship
2g USD 1350 Ready to ship
5g USD 2650 Ready to ship
Bulk inquiry

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:

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.

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 20.0 24.33

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.

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: 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: 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 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.

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5: Garaix F, Stern M, Lamy FX, Dubel L, Kamar N. Tacrolimus Granules for Oral Suspension as Post-Transplant Immunosuppression in Routine Medical Practice in France: The OPTIMOD Study. Ann Transplant. 2018 Aug 10;23:561-571. doi: 10.12659/AOT.908522. PubMed PMID: 30093607.

6: Zhao LN, Liang Y, Fang XJ, Liu XM, Jiang QL, Wang SS, She SF, Cao M. Efficacy and safety of tacrolimus in Osserman grade III and Osserman grade IV Myasthenia Gravis. Clin Neurol Neurosurg. 2018 Jul 30;173:70-76. doi: 10.1016/j.clineuro.2018.07.023. [Epub ahead of print] PubMed PMID: 30092406.

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9: Shibuya T, Haga K, Kamei M, Okahara K, Ito S, Takahashi M, Nomura O, Murakami T, Makino M, Kodani T, Ishikawa D, Sakamoto N, Osada T, Ogihara T, Watanabe S, Nagahara A. Successful remission of ulcerative colitis flare-up during pregnancy with adsorptive granulomonocytapheresis plus tacrolimus. Intest Res. 2018 Jul;16(3):484-488. doi: 10.5217/ir.2018.16.3.484. Epub 2018 Jul 27. PubMed PMID: 30090048; PubMed Central PMCID: PMC6077305.

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11: Klaasen RA, Bergan S, Bremer S, Daleq L, Andersen AM, Midtvedt K, Skauby MH, Vethe NT. A Longitudinal Study of Tacrolimus in Lymphocytes during the First Year after Kidney Transplantation. Ther Drug Monit. 2018 Aug 1. doi: 10.1097/FTD.0000000000000539. [Epub ahead of print] PubMed PMID: 30086087.

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13: Lawson BO, Seth H, Quan D. Phenytoin and Rifampin Do Not Decrease Levels in Acute Tacrolimus Toxicity. J Investig Med High Impact Case Rep. 2018 Mar 24;6:2324709618765862. doi: 10.1177/2324709618765862. eCollection 2018 Jan-Dec. PubMed PMID: 30083554; PubMed Central PMCID: PMC6062773.

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