FK5

8-DEETHYL-8-[BUT-3-ENYL]-ASCOMYCIN

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is present as a standalone ligand in 35 entries

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Chemical Component Summary
Name	8-DEETHYL-8-[BUT-3-ENYL]-ASCOMYCIN
Synonyms	K506
Identifiers	n/a
Formula	C₄₄ H₆₉ N O₁₂
Molecular Weight	804.018
Type	NON-POLYMER
Isomeric SMILES	C[C@@H]1C[C@@H]([C@@H]2[C@H](C[C@H]([C@@](O2)(C(=O)C(=O)N3CCCC[C@H]3C(=O)O[C@@H]([C@@H]([C@H](CC(=O)[C@@H](\C=C(\C1)/C)CC=C)O)C)/C(=C/[C@@H]4CC[C@H]([C@@H](C4)OC)O)/C)O)C)OC)OC
InChI	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
InChIKey	QJJXYPPXXYFBGM-LFZNUXCKSA-N

Chemical Details
Formal Charge	0
Atom Count	126
Chiral Atom Count	14
Bond Count	129
Aromatic Bond Count	0

Drug Info: DrugBank

DrugBank ID	DB00864
Name	Tacrolimus
Groups	approved investigational
Description	Tacrolimus (also FK-506 or Fujimycin) is an immunosuppressive drug whose main use is after organ transplant to reduce the activity of the patient's immune system and so the risk of organ rejection. It is also used in a topical preparation in the treatment of severe atopic dermatitis, severe refractory uveitis after bone marrow transplants, and the skin condition vitiligo. It was discovered in 1984 from the fermentation broth of a Japanese soil sample that contained the bacteria Streptomyces tsukubaensis. Tacrolimus is chemically known as a macrolide. It reduces peptidyl-prolyl isomerase activity by binding to the immunophilin FKBP-12 (FK506 binding protein) creating a new complex. This FKBP12-FK506 complex inhibits calcineurin which inhibits T-lymphocyte signal transduction and IL-2 transcription.
Synonyms	Tacrolimus hydrate Tacrolimus, anhydrous Tacrolimus Tacrolimus anhydrous Anhydrous tacrolimus
Brand Names	Tacrolimus 0.1% In Pseudocatalase Taro-tacrolimus Apo-tacrolimus Modigraf Prograf Sandoz Tacrolimus Apo-tacrolimus Capsules Jamp-tacrolimus Leo Pharma - Tacrolimus Niacinamide 4% / Tacrolimus 0.03% Astagraf XL Protopic Envarsus Tacforius Tacrus Sandoz Tacrolimus XR Ach-tacrolimus Envarsus Pa Envarsus XR Tacrolimus Hyaluronic Acid Sodium Salt 1% / Tacrolimus 0.1% / Urea 20% Validerm Niacinamide 4% / Tacrolimus 0.1% Hyaluronic Acid Sodium Salt 1% / Niacinamide 4% / Tacrolimus 0.1% Tacrolimus 0.1% Advagraf Hecoria
Indication	Immediate-release formulations of tacrolimus are indicated for the prophylaxis of organ rejection in adult and pediatric patients receiving allogeneic liver, kidney, heart, or lung transplants, in combination with other immunosuppressants.[L8162] Extended-release formulations of tacrolimus are indicated for the prophylaxis of organ rejection in adult and pediatric patients receiving kidney transplants, in combination with other immunosuppressants,[L20034,L41005] and may be used in patients converted from immediate-release formulations.[L41005] Topical tacrolimus ointment is indicated as second-line therapy for short-term and non-continuous treatment of moderate-to-severe atopic dermatitis in non-immunocompromised adults and children who have failed to respond adequately to other topical treatments or for whom alternative treatments are not advisable.[L3935] Both available strengths are indicated in adult patients, while only the lower strength (0.03%) formulation is indicated in pediatric patients between 2 and 15 years of age.[L3935]
Categories	Agents causing hyperkalemia Agents Causing Muscle Toxicity Agents for Dermatitis, Excluding Corticosteroids Antineoplastic and Immunomodulating Agents Calcineurin Inhibitor Immunosuppressant Calcineurin Inhibitors Cytochrome P-450 CYP3A Inhibitors Cytochrome P-450 CYP3A Substrates Cytochrome P-450 CYP3A4 Inhibitors Cytochrome P-450 CYP3A4 Inhibitors (weak) Cytochrome P-450 CYP3A4 Substrates Cytochrome P-450 CYP3A4 Substrates with a Narrow Therapeutic Index Cytochrome P-450 CYP3A5 Substrates Cytochrome P-450 CYP3A5 Substrates with a Narrow Therapeutic Index Cytochrome P-450 Enzyme Inhibitors Cytochrome P-450 Substrates Dermatologicals Drugs causing inadvertant photosensitivity Enzyme Inhibitors Hyperglycemia-Associated Agents Immunologic Factors Immunosuppressive Agents Lactones Misc. Skin and Mucous Membrane Agents Myelosuppressive Agents Narrow Therapeutic Index Drugs Nephrotoxic agents OATP1B1/SLCO1B1 Inhibitors P-glycoprotein inducers P-glycoprotein inhibitors P-glycoprotein substrates P-glycoprotein substrates with a Narrow Therapeutic Index Photosensitizing Agents Polyketides Potential QTc-Prolonging Agents QTc Prolonging Agents
ATC-Code	D11AH01 L04AD02
CAS number	104987-11-3

Drug Targets

Name	Target Sequence	Pharmacological Action	Actions
Peptidyl-prolyl cis-trans isomerase FKBP1A	MGVQVETISPGDGRTFPKRGQTCVVHYTGMLEDGKKFDSSRDRNKPFKFM...	unknown	inhibitor
Cytochrome P450 3A4	MALIPDLAMETWLLLAVSLVLLYLYGTHSHGLFKKLGIPGPTPLPFLGNI...	unknown	substrate
Cytochrome P450 3A5	MDLIPNLAVETWLLLAVSLVLLYLYGTRTHGLFKRLGIPGPTPLPLLGNV...	unknown	substrate
Serum albumin	MKWVTFISLLFLFSSAYSRGVFRRDAHKSEVAHRFKDLGEENFKALVLIA...	unknown	substrate
Alpha-1-acid glycoprotein 1	MALSWVLTVLSLLPLLEAQIPLCANLVPVPITNATLDQITGKWFYIASAF...	unknown	substrate
P-glycoprotein 1	MDLEGDRNGGAKKKNFFKLNNKSEKDKKEKKPTVSVFSMFRYSNWLDKLY...	unknown	substrate,inhibitor,inducer
ATP-binding cassette sub-family A member 5	MSTAIREVGVWRQTRTLLLKNYLIKCRTKKSSVQEILFPLFFLFWLILIS...	unknown	substrate
Solute carrier organic anion transporter family member 1B1	MDQNQHLNKTAEAQPSENKKTRYCNGLKMFLAALSLSFIAKTLGAIIMKS...	unknown	inhibitor
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Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682