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Substance Name: Tacrolimus [USAN:INN:BAN]
RN: 109581-93-3
UNII: WM0HAQ4WNM
InChIKey: NWJQLQGQZSIBAF-MLAUYUEBSA-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.H2-O

Molecular Weight

  • 822.0389
 

Classification Codes

  • Calcineurin Inhibitors
  • Drug / Therapeutic Agent
  • Enzyme Inhibitors
  • Immunologic Factors
  • Immunosuppressant
  • Immunosuppressive Agents

Names and Synonyms

Name of Substance

  • Tacrolimus
  • Tacrolimus [USAN:INN:BAN]

MeSH Heading

  • Tacrolimus

Synonyms

  • (-)-(3S,4R,5S,8R,9E,12S,14S,15R,16S,18R,19R,26aS)-8-allyl-5,6,8,11,12,13,14,15,16,17,18,19,24,25,26,26a-Hexadecahydro-5,19-dihydroxy-3-((E)-2-((1R,3R,4R)-4-hydroxy-3-methoxycyclohexyl)-1-methylvinyl)-14,16-dimethoxy-4,10,12,18-tetramethyl-15,19-epoxy-3H-pyrido(2,1-c)(1,4)oxaazacyclotricosine-1,7,20,21(4H,23H)-tetrone)monohydrate
  • 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*))-
  • Astagraf XL
  • FK 506
  • FR 900506
  • FR900506
  • LCP-Tacro
  • Prograf
  • Protopic
  • Tacrolimus
  • Tacrolimus hydrate
  • Tsukubaenolide hydrate
  • UNII-WM0HAQ4WNM

Systematic 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*))-

Registry Numbers

CAS Registry Number

  • 109581-93-3

FDA UNII

  • WM0HAQ4WNM

Related Registry Number

  • 104987-11-3 (Parent)

System Generated Number

  • 0109581933

Molecular Formulas

Molecular Formula

  • C44-H69-N-O12.H2-O

Molecular Formula Fragments

  • C44-H69-N-O12
  • COMPONENT
  • H2-O

Structure Descriptors

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

InChIKey

NWJQLQGQZSIBAF-MLAUYUEBSA-N

Smiles

O.CO[C@@H]1C[C@@H](CC[C@H]1O)\C=C(/C)\[C@H]2OC(=O)[C@@H]3CCCCN3C(=O)C(=O)[C@]4(O)O[C@H]([C@H](C[C@@H](C)C\C(=C\[C@@H](CC=C)C(=O)C[C@H](O)[C@H]2C)\C)OC)[C@H](C[C@H]4C)OC

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
rat LD50 intravenous 23600ug/kg (23.6mg/kg)   Drugs in Japan Vol. -, Pg. 720, 1995.
rat LD50 oral 134mg/kg (134mg/kg)   Drugs in Japan Vol. -, Pg. 720, 1995.