Chemicals and Drugs

Tacrolimus

A macrolide isolated from the culture broth of a strain of Streptomyces tsukubaensis that has strong immunosuppressive activity in vivo and prevents the activation of T-lymphocytes in response to antigenic or mitogenic stimulation in vitro.

National Library of MedicineMedical Subject Headings2026

Structured Summary

Abstract

A macrolide isolated from the culture broth of a strain of Streptomyces tsukubaensis that has strong immunosuppressive activity in vivo and prevents the activation of T-lymphocytes in response to antigenic or mitogenic stimulation in vitro.

Chemical Identity

Chemical Information

Molecular Formula
C44H69NO12
Molecular Weight
804.0 g/mol
CAS Registry No.
104987-11-3
IUPAC Name
(1R,9S,12S,13R,14S,17R,18E,21S,23S,24R,25S,27R)-1,14-dihydroxy-12-[(E)-1-[(1R,3R,4R)-4-hydroxy-3-methoxycyclohexyl]prop-1-en-2-yl]-23,25-dimethoxy-13,19,21,27-tetramethyl-17-prop-2-enyl-11,28-dioxa-4-azatricyclo[22.3.1.04,9]octacos-18-ene-2,3,10,16-tetrone
InChIKey
QJJXYPPXXYFBGM-LFZNUXCKSA-N
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
MeSH Unique ID
D016559
Source
PubChem CID 445643

MeSH Record

Classification

Broader headings

Related Concepts

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Drug Class

Pharmacological Action

MeSH Record

Synonyms

12 entry terms
  • Anhydrous Tacrolimus
  • FK-506
  • FK506
  • FR-900506
  • Prograf
  • Prograft
  • Tacrolimus Anhydrous
  • Anhydrous, Tacrolimus
  • FK 506
  • FR 900506
  • FR900506
  • Tacrolimus, Anhydrous

MeSH Record

Aspects Covered

25 allowable subheadings

Indexed with the subheadings administration & dosage, adverse effects, agonists, analogs & derivatives, analysis, antagonists & inhibitors, blood, cerebrospinal fluid, chemical synthesis, chemistry, classification, economics, history, immunology, isolation & purification, metabolism, pharmacokinetics, pharmacology, poisoning, radiation effects, standards, supply & distribution, therapeutic use, toxicity, urine.

MeSH Record

History Note

96; was FK-506 1992-95, was FK 506 (NM) 1987-91

MeSH Record

Previous Indexing

  • Antibiotics, Macrolide (1987-1991)
  • Immunosuppressive Agents (1987-1991)

MeSH Hierarchy

Tree Number

  1. D02w.540w.505w.810w

AMA Style

References

  1. National Library of Medicine. Tacrolimus. Medical Subject Headings (MeSH). 2026. Unique ID D016559. http://id.nlm.nih.gov/mesh/2026/D016559
  2. Tacrolimus. In: Wikipedia. https://en.wikipedia.org/wiki/Tacrolimus
  3. Tacrolimus. In: Wikidata. https://www.wikidata.org/wiki/Q411648
  4. Tacrolimus. In: PubChem Compound. CID 445643. https://pubchem.ncbi.nlm.nih.gov/compound/445643