Tacrolimus
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MedKoo CAT#: 100795

CAS#: 104987-11-3 (free base)

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
CAS# 104987-11-3 (free base)

Theoretical Analysis

MedKoo Cat#: 100795
Name: Tacrolimus
CAS#: 104987-11-3 (free base)
Chemical Formula: C44H69NO12
Exact Mass: 803.48198
Molecular Weight: 804.02
Elemental Analysis: C, 65.73; H, 8.65; N, 1.74; O, 23.88

Price and Availability

Size Price Availability Quantity
50.0mg USD 190.0 Same day
200.0mg USD 250.0 Same day
1.0g USD 450.0 Same day
2.0g USD 850.0 Same day
5.0g USD 1850.0 2 Weeks
10.0g USD 3350.0 2 Weeks
20.0g USD 5850.0 2 Weeks
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Related CAS #: 109581-93-3 (hydrate)   104987-11-3 (free base)    

Synonym: FK 506, FK-506, FK506, fujimycin, fujimycin, Prograf, Protopic, Advagraf; Astagraf XL;

IUPAC/Chemical Name: [3S [3R*[E(1S*,3S*,4S*)], 4S*,5R*,8S*,9E,12R*,14R*,15S*,16R*,18S*,19S*,26aR*]] -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)-15,19-epoxy-3H-pyrido[2,1-c][1,4] oxaazacyclotricosine-1,7,20,21(4H,23H)-tetrone

InChi Key: QJJXYPPXXYFBGM-GANIDMSDSA-N

InChi Code: InChI=1S/C44H69NO12/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/b25-19+,27-21+/t26-,28+,29+,30-,31+,32-,33?,34-,36?,37-,38-,39+,40+,44+/m0/s1

SMILES Code: O=C([C@@](CCCC1)([H])N1C(C([C@@]2(O)[C@H](C)C[C@H](OC)[C@@](O2)([H])[C@@H](OC)C[C@@H](C)C/C(C)=C/[C@H]3CC=C)=O)=O)O[C@H](/C(C)=C/[C@H]4CC(OC)C(O)CC4)[C@H](C)[C@@H](O)CC3=O

Appearance: White 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).

HS Tariff Code: 2934.99.9001

Preparing Stock Solutions

The following data is based on the product molecular weight 804.02 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

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1: Penninga L, Penninga EI, Møller CH, Iversen M, Steinbrüchel DA, Gluud C. Tacrolimus versus cyclosporin as primary immunosuppression for lung transplant recipients. Cochrane Database Syst Rev. 2013 May 31;5:CD008817. doi: 10.1002/14651858.CD008817.pub2. Review. PubMed PMID: 23728681.

2: Sekiguchi Y, Shimada A, Imai H, Wakabayashi M, Sugimoto K, Nakamura N, Sawada T, Komatsu N, Noguchi M. Epstein-Barr virus-negative, CD5-positive diffuse large B-cell lymphoma developing after treatment with oral tacrolimus for mixed connective tissue disease : a case report and review of the literature. J Clin Exp Hematop. 2012;52(3):211-8. Review. PubMed PMID: 23269082.

3: Remitz A, Reitamo S. Long-term safety of tacrolimus ointment in atopic dermatitis. Expert Opin Drug Saf. 2009 Jul;8(4):501-6. doi: 10.1517/14740330902969441 . Review. PubMed PMID: 19435404.

4: Sánchez-Pérez J. [Safety information for tacrolimus: present and future]. Actas Dermosifiliogr. 2008 Feb;99 Suppl 2:19-25. Review. Spanish. PubMed PMID: 18346426.

5: Torrelo A. [Topical tacrolimus in atopic dermatitis in children]. Actas Dermosifiliogr. 2008 Feb;99 Suppl 2:14-8. Review. Spanish. PubMed PMID: 18346425.

6: Ortiz de Frutos FJ. [Atopic dermatitis and tacrolimus in adults]. Actas Dermosifiliogr. 2008 Feb;99 Suppl 2:8-13. Review. Spanish. PubMed PMID: 18346424.

7: Rustin MH. The safety of tacrolimus ointment for the treatment of atopic dermatitis: a review. Br J Dermatol. 2007 Nov;157(5):861-73. Epub 2007 Sep 13. Review. PubMed PMID: 17854353.

8: Sánchez-Pérez J. [Topical pimecrolimus and tacrolimus and the risk of cancer]. Actas Dermosifiliogr. 2007 Jun;98(5):312-7. Review. Spanish. PubMed PMID: 17555673.

9: van Dieren JM, Kuipers EJ, Samsom JN, Nieuwenhuis EE, van der Woude CJ. Revisiting the immunomodulators tacrolimus, methotrexate, and mycophenolate mofetil: their mechanisms of action and role in the treatment of IBD. Inflamm Bowel Dis. 2006 Apr;12(4):311-27. Review. PubMed PMID: 16633053.

10: Ormerod AD. Topical tacrolimus and pimecrolimus and the risk of cancer: how much cause for concern? Br J Dermatol. 2005 Oct;153(4):701-5. Review. PubMed PMID: 16181449.

11: Dé Tran QH, Guay E, Chartier S, Tousignant J. Tacrolimus in dermatology. J Cutan Med Surg. 2001 Jul-Aug;5(4):329-35. Epub 2001 May 2. Review. PubMed PMID: 11907845.

12: Nghiem P, Pearson G, Langley RG. Tacrolimus and pimecrolimus: from clever prokaryotes to inhibiting calcineurin and treating atopic dermatitis. J Am Acad Dermatol. 2002 Feb;46(2):228-41. Review. PubMed PMID: 11807435.

13: Woo M, Przepiorka D, Ippoliti C, Warkentin D, Khouri I, Fritsche H, Körbling M. Toxicities of tacrolimus and cyclosporin A after allogeneic blood stem cell transplantation. Bone Marrow Transplant. 1997 Dec;20(12):1095-8. Review. PubMed PMID: 9466284.