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Substance Name: Tacrolimus [USAN:INN]
RN: 104987-11-3
UNII: Y5L2157C4J
InChIKey: QJJXYPPXXYFBGM-LFZNUXCKSA-N

Note

  • 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.

Molecular Formula

  • C44-H69-N-O12

Molecular Weight

  • 804.0241
 

Classification Codes

  • Drug / Therapeutic Agent
  • Immunologic Factors
  • Immunosuppressive Agents
  • Natural Product
  • Reproductive Effect

Names and Synonyms

Results Name

  • Tacrolimus [USAN:INN]

Name of Substance

  • Tacrolimus anhydrous
  • Tacrolimus [USAN:INN]

MeSH Heading

  • Tacrolimus

Synonyms

  • (-)-FK 506
  • Advagraf
  • Anhydrous tacrolimus
  • Astagraf XL
  • Avagraf
  • CCRIS 7124
  • Envarsus
  • Envarsus Xr
  • FK 506
  • FK506
  • FR 900506
  • Fujimycin
  • HSDB 8195
  • L 679934
  • LCP-Tacro
  • Modigraf
  • Prograf
  • Prograft
  • Protopic
  • Protopy
  • Tacrolimus
  • Tsukubaenolide
  • UNII-Y5L2157C4J

Systematic Names

  • 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)-14,16-dimethoxy-4,10,12,18-tetramethyl-8-(2-propenyl)-, (3S-(3R*(E(1S*,3S*,4S*)),4S*,5R*,8S*,9E,12R*,14R*,15S*,16R*,18S*,19S*,26aR*))-
  • FK506

Registry Numbers

CAS Registry Number

  • 104987-11-3

FDA UNII

  • Y5L2157C4J

Related Registry Number

  • 109581-93-3 (Hydrate)

System Generated Number

  • 0104987113

Structure Descriptors

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

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

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal > 200mg/kg (200mg/kg)   Journal of Antibiotics. Vol. 40, Pg. 1249, 1987.