Tacrolimus CAS 109581-93-3

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Identification

CAS Number

109581-93-3

Name

Tacrolimus

Synonyms

(1R,9S,12S,13R,14S,17R,18E,21S,23S,24R,25S,27R)-17-Allyl-1,14-dihydroxy-12-{(1E)-1-[(1R,3R,4R)-4-hydroxy-3-methoxycyclohexyl]-1-propen-2-yl}-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-azatr ;icyclo[22.3.1.04,9]octacos-18-en-2,3,10,16-tetronhydrat (1:1) [German] [ACD/IUPAC Name]
(1R,9S,12S,13R,14S,17R,18E,21S,23S,24R,25S,27R)-17-Allyl-1,14-dihydroxy-12-{(1E)-1-[(1R,3R,4R)-4-hydroxy-3-methoxycyclohexyl]-1-propen-2-yl}-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-azatr ;icyclo[22.3.1.04,9]octacos-18-ene-2,3,10,16-tetrone hydrate (1:1) [ACD/IUPAC Name]
(1R,9S,12S,13R,14S,17R,18E,21S,23S,24R,25S,27R)-17-Allyl-1,14-dihydroxy-12-{(1E)-1-[(1R,3R,4R)-4-hydroxy-3-méthoxycyclohexyl]-1-propén-2-yl}-23,25-diméthoxy-13,19,21,27-tétraméthyl-11,28-dioxa-4-azatr ;icyclo[22.3.1.04,9]octacos-18-ène-2,3,10,16-tétrone, hydrate (1:1) [French] [ACD/IUPAC Name]
109581-93-3 [RN]
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-[(E)-2-[(1R,3R,4R)-4-hydroxy-3-methoxycycl ohexyl]-1-methylethenyl]-14,16-dimethoxy-4,10,12,18-tetramethyl-8-(2-propen-1-yl)-, (3S,4R,5S,8R,9E,12S,14S,15R,16S,18R,19R,26aS)-, hydrate (1:1) [ACD/Index Name]
FK-506 monohydrate
KD4201200
MFCD11045918 [MDL number]
Tacrolimus [BAN] [INN] [JAN] [USAN] [Wiki]
Tacrolimus for system suitability
Tacrolimus hydrate
TACROLIMUS MONOHYDRATE
(-)-(3S,4R,5S,8R,9E,12S,14S,15R,16S,18R,19R,26aS)-5,19-dihydroxy-3-{(1E)-1-[(1R,3R,4R)-4-hydroxy-3-methoxycyclohexyl]prop-1-en-2-yl}-14,16-dimethoxy-4,10,12,18-tetramethyl-8-(prop-2-en-1-yl)-5,6,8,11,12,13,14,15,16,17,18,19,24,25,26,26a-hexadecahydro-3H-15,19-epoxypyrido[2,1-c][1,4]oxazacyclotricosine-1,7,20,21(4H,23H)-tetrone monohydratetacrolimus
(3S,4R,5S,8R,9E,12S,14S,15R,16S,18R,19R,26aS)-5,19-dihydroxy-3-{(1E)-1-[(1R,3R,4R)-4-hydroxy-3-methoxycyclohexyl]prop-1-en-2-yl}-14,16-dimethoxy-4,10,12,18-tetramethyl-8-(prop-2-en-1-yl)-5,6,8,11,12,1
(3S,4R,5S,8R,9E,12S,14S,15R,16S,18R,19R,26aS)-5,19-dihydroxy-3-{(1E)-1-[(1R,3R,4R)-4-hydroxy-3-methoxycyclohexyl]prop-1-en-2-yl}-14,16-dimethoxy-4,10,12,18-tetramethyl-8-(prop-2-en-1-yl)-5,6,8,11,12,13,14,15,16,17,18,19,24,25,26,26a-hexadecahydro-3H-15,19-epoxypyrido[2,1-c][1,4]oxazacyclotricosine-1,7,20,21(4H,23H)-tetrone–water (1/1)
[109581-93-3]
109581-93-3 (hydrate)
3,14,15,16,17,18,19,24,25,26,26a-hexadecahydro-3H-15,19-epoxypyrido[2,1-c][1,4]oxazacyclotricosine-1,7,20,21(4H,23H)-tetrone–water (1/1)
FK506
https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:61057
KS-1245
Prograf [Trade name]
Prograf (TN)
Prograf; Protopic
Protopic
Protopic (TN)
Tacrolimus (monohydrate)
Tacrolimus (USAN/INN)
Tacrolimus hydrate (JAN) [JAN]
Tacrolimus Monohydrate 1.0 mg/ml in Acetonitrile (as anhydrous substance)
Tacrolimus monohydrate; FK506
Tsukubaenolide hydrate

SMILES

C[[email protected]@H]1C[[email protected]@H]([[email protected]@H]2[[email protected]](C[[email protected]]([[email protected]@](O2)(C(=O)C(=O)N3CCCC[[email protected]]3C(=O)O[[email protected]@H]([[email protected]@H]([[email protected]](CC(=O)[[email protected]@H](/C=C(/C1)\C)CC=C)O)C)/C(=C/[[email protected]@H]4CC[[email protected]]([[email protected]@H](C4)OC)O)/C)O)C)OC)OC.O

StdInChI

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

StdInChIKey

NWJQLQGQZSIBAF-MLAUYUEBSA-N

Molecular Formula

C₄₄H₆₉NO₁₂ · H₂O

Molecular Weight

822.03

MDL Number

MFCD11045918

Properties

Appearance

White or almost white powder

Safety Data

Symbol

GHS06

Signal Word

Danger

Hazard statements

Precautionary Statements

RIDADR 

UN 2811 6.1 / PGIII

WGK Germany

3

Specifications and Other Information of Our Tacrolimus CAS 109581-93-3

Identification Methods

HNMR, HPLC

Assay

98.0% ~ 102.0%

Specific Optical Rotation

-110°~ -115°

Heavy Metals

≤10 ppm

Water

≤4.0%

Organic Impurities

Asomycin 19-Epimer

≤0.1%

Ascomycin

≤0.5%

Desmethyl Tacrolimus

≤0.1%

Tacrolimus 8-Epimer

≤0.15%

Tacrolimus 8-Propyl Analog

≤0.15%

Any Individual Un Specified Impurity

≤0.1%

Total Impurities

≤1.0%

Residual Solvent

Ethanol

≤0.5%

Acetone

≤0.5%

Ethyl Acetate

≤0.5%

Isopropyl Ether

≤0.5%

Shelf Life

2 years

Storage

Store at 2-8℃, sealed and away from light.

Known Application

Tacrolimus is a macrolide compound that binds to FK506 binding protein (FKBP) to form a complex and inhibits calcineurin phosphatase, thereby inhibiting T lymphocyte signal transduction and IL-2 transcription. It has strong immunosuppressive properties.

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