Tacrolimus Monohydrate - Moligand™,≥80%(HPLC) , CAS No.109581-93-3

CAS: 109581-93-3 Cat. No.: F138016 Peso molecular: 822.03 Número EC: 634-559-2

GRADE & PURITY Moligand™, ≥80%(HPLC)

Synonyms

D00107 | Tacrolimus, Pharmaceutical Secondary Standard; Certified Reference Material | TACROLIMUS [USP-RS] | TACROLIMUS MONOHYDRATE [WHO-DD] | FK 506 | TACROLIMUS [ORANGE BOOK] | TACROLIMUS MONOHYDRATE | WM0HAQ4WNM | FK-506 monohydrate, >=98% (HPLC) | Pro

Storage

Protected from light,Store at -20°C,Argon charged

Shipped In

Ice chest + Ice pads

Descripción general

Application

FK-506 monohydrate has been used:

as an immunosuppressive agent in coculture medium to study the effect of immunologic reaction

as a calcineurin inhibitor, in anhydrous Me2SO solution

to treat retinal pigment epithelial cells to measure possible cytotoxicity

Specifications

Sinónimos

D00107 | Tacrolimus, Pharmaceutical Secondary Standard; Certified Reference Material | TACROLIMUS [USP-RS] | TACROLIMUS MONOHYDRATE [WHO-DD] | FK 506 | TACROLIMUS [ORANGE BOOK] | TACROLIMUS MONOHYDRATE | WM0HAQ4WNM | FK-506 monohydrate, >=98% (HPLC) | Pro

Especificaciones y pureza

Moligand™, ≥80%(HPLC)

Mecanismos bioquímicos y fisiológicos

It is a potent immunosuppressant, neuroprotective and neuroregenerative, and in vitro T cell proliferation blocker. FK-506 disrupts calcineurin-mediated signal transduction in T lymphocytes and interacts with its FK-506-binding protein-12 (FKBP12).

Condiciones de almacenamiento de almacenamiento

Protected from light, Store at -20°C, Argon charged

Enviado en

Ice chest + Ice pads

Este producto requiere envío en cadena de frío. Los servicios terrestres y otros servicios económicos no están disponibles.

Grado

Moligand™

Tipo de acción

INHIBITOR

Pureza

≥80%(HPLC)

Nombres e identificadores

• Pubchem Sid: 504763414
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504763414
• Sonrisas canónicas: CC1CC(C2C(CC(C(O2)(C(=O)C(=O)N3CCCCC3C(=O)OC(C(C(CC(=O)C(C=C(C1)C)CC=C)O)C)C(=CC4CCC(C(C4)OC)O)C)O)C)OC)OC.O
• 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;hydrate
• InChIKey: NWJQLQGQZSIBAF-MLAUYUEBSA-N
• 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
• Isómeros 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.O
• WGK Alemania: 3
• RTECS: KD4201200
• Peso molecular: 822.03
• Reaxy-Rn: 43416939
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=43416939&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Phenylpropanoids and polyketides
    • Clase Macrolide lactams

• Kingdom: Organic compounds
• Superclass: Phenylpropanoids and polyketides
• Clase: Macrolide lactams
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: Macrolide lactams
• Alternative Parents: Alpha amino acid esters Macrolides and analogues Cyclohexanols Piperidines Oxanes Tertiary carboxylic acid amides Carboxylic acid esters Cyclic alcohols and derivatives Cyclic ketones Hemiacetals Lactams Lactones Azacyclic compounds Dialkyl ethers Oxacyclic compounds Monocarboxylic acids and derivatives Hydrocarbon derivatives Organopnictogen compounds Organonitrogen compounds Organic oxides
• Molecular Framework: Aliphatic heteropolycyclic compounds
• Substituents: Macrolide lactam - Alpha-amino acid ester - Macrolide - Alpha-amino acid or derivatives - Cyclohexanol - Oxane - Piperidine - Cyclic alcohol - Tertiary carboxylic acid amide - Cyclic ketone - Secondary alcohol - Carboxamide group - Carboxylic acid ester - Hemiacetal - Ketone - Lactam - Lactone - Organoheterocyclic compound - Azacycle - Carboxylic acid derivative - Oxacycle - Dialkyl ether - Ether - Monocarboxylic acid or derivatives - Organopnictogen compound - Alcohol - Organic oxygen compound - Carbonyl group - Organooxygen compound - Organonitrogen compound - Organic nitrogen compound - Hydrocarbon derivative - Organic oxide - Aliphatic heteropolycyclic compound
• Descripción: This compound belongs to the class of organic compounds known as macrolide lactams. These are cyclic polyketides containing both a cyclic amide and a cyclic ester group.
• External Descriptors: hydrate

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Mecanismos de acción

Propiedades químicas y físicas

• Solubilidad: Soluble in 20 mg/mL of DMSO
• Sensibilidad: light & heat sensitive
• Punto de fusión (°C): 127 °C
• Peso molecular: 822.000 g/mol
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 13
• Rotatable Bond Count: 7
• Exact Mass: 821.493 Da
• Monoisotopic Mass: 821.493 Da
• Topological Polar Surface Area: 179.000 Ų
• Heavy Atom Count: 58
• Formal Charge: 0
• Complexity: 1480.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 14
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 2
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 2
• Covalently-Bonded Unit Count: 2

XLogP3

Referencias

1. Feng Chen, Xiaoxia Yang, Huanhuan Li, Xiaodan Zeng, Ziwei Deng, Hongqiang Wang, Yuanxiang Jin, Chengfeng Qiu, Zhihua Shi.  (2023)  Improved LC–MS/MS method for the simultaneous quantification of tacrolimus and cyclosporine A in human blood and application to therapeutic drug monitoring.  BIOMEDICAL CHROMATOGRAPHY,  37  (12): (e5751).  [PMID:37772369] [10.1002/bmc.5751]

2. Xiaoqian Jiang, Xinxin Xu, Hua Kuang, Liqiang Liu, Liguang Xu, Aihua Qu, Chuanlai Xu.  (2023)  A gold-based immunochromatographic strip for the specific detection of tacrolimus in whole blood.  Journal of Materials Chemistry B,  11  (20): (4464-4474).  [PMID:37159048] [10.1039/D3TB00569K]

3. Fei Gong, Huihui Hu, Ying Ouyang, Zheng-Zheng Liao, Ying Kong, Jin-Fang Hu, Hua He, Ying Zhou.  (2023)  Physiologically-based pharmacokinetic modeling-guided rational combination of tacrolimus and voriconazole in patients with different CYP3A5 and CYP2C19 alleles.  TOXICOLOGY AND APPLIED PHARMACOLOGY,      [PMID:36931438] [10.1016/j.taap.2023.116475]

4. Wang Hongkang, Ji Zhe, Feng Yanru, Yan Tianhua, Cao Yongbing, Lu Hui, Jiang Yuanying.  (2022)  Myriocin enhances the antifungal activity of fluconazole by blocking the membrane localization of the efflux pump Cdr1.  Frontiers in Pharmacology,      [PMID:36618949] [10.3389/fphar.2022.1101553]

5. Qingfeng He, Fengjiao Bu, Qizhen Wang, Min Li, Jiaying Lin, Zhijia Tang, Wen Yao Mak, Xiaomei Zhuang, Xiao Zhu, Hai-Shu Lin, Xiaoqiang Xiang.  (2022)  Examination of the Impact of CYP3A4/5 on Drug–Drug Interaction between Schizandrol A/Schizandrol B and Tacrolimus (FK-506): A Physiologically Based Pharmacokinetic Modeling Approach.  INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES,  23  (9): (4485).  [PMID:35562875] [10.3390/ijms23094485]

6. Gao Ping, Du Xiaoyi, Liu Lili, Xu Hua, Liu Maochang, Guan Xinlei, Zhang Chengliang.  (2021)  Astragaloside IV Alleviates Tacrolimus-Induced Chronic Nephrotoxicity via p62-Keap1-Nrf2 Pathway.  Frontiers in Pharmacology,      [PMID:33536919] [10.3389/fphar.2020.610102]

7. Y. Chen, Y. Yang, F. Wang, X. Yang, F. Yao, K. Ming, W. Yuan, L. Zeng, J. Liu.  (2019)  Antiviral effect of baicalin phospholipid complex against duck hepatitis A virus type 1.  POULTRY SCIENCE,      [PMID:29757435] [10.3382/ps/pey155]

8. Hongyan Zhang, Fengjiao Bu, Lei Li, Zheng Jiao, Guo Ma, Weimin Cai, Xiaomei Zhuang, Hai-Shu Lin, Jae-Gook Shin, Xiaoqiang Xiang.  (2017)  Prediction of Drug–Drug Interaction between Tacrolimus and Principal Ingredients of Wuzhi Capsule in Chinese Healthy Volunteers Using Physiologically-Based Pharmacokinetic Modelling.  BASIC & CLINICAL PHARMACOLOGY & TOXICOLOGY,  122  (3): (331-340).  [PMID:28945011] [10.1111/bcpt.12914]

9. Xinhang Meng, Minfeng Shi, Jinfeng Qian, Yujie Luo, Liyuan Cui, Dajin Li, Songcun Wang.  (2025)  Tacrolimus (FK506) promotes placentation and maternal-fetal tolerance through modulating FASN-CEACAM1 pathway.  Frontiers in Immunology,      [PMID:40046057] [10.3389/fimmu.2025.1522346]