Drug Details

General Information of the Drug (ID: DR1791)
Name
Tacrolimus
Synonyms
tacrolimus; Fujimycin; Prograf; 104987-11-3; Protopic; FK506; Tacrolimus anhydrous; Advagraf; Modigraf; Protopy; Fk-506; LCP-Tacro; Anhydrous Tacrolimus; tacrolimus (fk506); FK 506; FR-900506; 8-DEETHYL-8-[BUT-3-ENYL]-ASCOMYCIN; UNII-Y5L2157C4J; Astagraf XL; FR 900506; (-)-FK 506; Tsukubaenolide; Prograf (TN); FR900506; CHEMBL269732; CHEBI:61049; Y5L2157C4J; K506; NCGC00163470-03; Prograft; Avagraf; Envarsus; Graceptor; Envarsus XR; (3S,4R,5S,8R,9E,12S,14S,15R,16S,18R,19R,26aS)-5,6,8,11,12,13,14,15,16,17,18,19,24,25,26,26a-Hexadecahydro-5,19-dihydroxy-3-[(1E)-2-[(1R,3R,4R)-4-hydroxy-3-methoxycyclohexyl]-1-methylethenyl]-14,16-dimethoxy-4,10,12,18-tetramethyl-8-(2-propen-1-yl)-15,19-epoxy-3H-pyrido[2,1-c][1,4]oxaazacyclotricosine-1,7,20,21(4H,23H)tetrone; Tacrolimus (INN); Tacrolimus [USAN]; Tacrolimus, anhydrous; MFCD11045918; Tacrolimus (anhydrous); SR-05000001879; Tacrolimus [USAN:INN]; Hecoria; Talymus; CCRIS 7124; MFCD00869853; HSDB 8195; C44H69NO12; L 679934; FK-506/Tacrolimus; PubChem18875; FK-506 (Tacrolimus); SCHEMBL3088; DSSTox_CID_26354; DSSTox_RID_81557; DSSTox_GSID_46354; BSPBio_001279; CHEMBL66247; L-679934; GTPL6784; DTXSID5046354; CHEBI:93221; HMS503O21; HMS1792O21; HMS1990O21; HMS2093M19; HMS3403O21; Pharmakon1600-01503968; EX-A1677; Tox21_112056; ABP000474; BDBM50030448; BDBM50079777; LMPK04000003; NSC758659; s5003; AKOS005145901; ZINC169289411; AC-1182; AM81227; AT-2441; CCG-270494; CS-1507; DB00864; NSC-758659; IDI1_001040; NCGC00163470-01; NCGC00163470-02; NCGC00163470-04; NCGC00163470-05; NCGC00163470-06; NCGC00163470-07; NCGC00163470-27; (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; HY-13756; Fujimycin; ; ; FK-506; ; ; FR-900506; SBI-0052894.P002; AB0012538; CAS-104987-11-3; M2258; C01375; D08556; W-1246; AB01209746-01; AB01209746_03; 581T933; Q411648; Q-201775; SR-05000001879-1; SR-05000001879-2; SR-05000001879-5; BRD-K35452788-001-02-1; BRD-K69608737-001-03-7; BRD-K69608737-001-10-2; [(E)-2-[(1R,3R,4R)-4-hydroxy-3-methoxycyclohexyl]-1-methylethenyl]-14,16-; 15,19-epoxy-3H-pyrido[2,1-c][1,4]oxaazacyclotricosine-1,7,20,21(23H)-tetrone,; (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; (3S,4R,5S,8R,9E,12S,14S,15R,16S,18R,19R,26aS)-5,19-dihydroxy-3-{(E)-2-[(1R,3R,4R)-4-hydroxy-3-methoxycyclohexyl]-1-methylethenyl}-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; (E)-(1R,9S,12S,13R,14R,21S,23S,24R,25S,27R)-17-Allyl-1,14-dihydroxy-12-[(E)-2-((3R,4R)-4-hydroxy-3-methoxy-cyclohexyl)-1-methyl-vinyl]-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-aza-tricyclo[22.3.1.0*4,9*]octacos-18-ene-2,3,10,16-tetraone; 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*))-; 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-[(1E)-2-[(1R,3R,4R)-4-hydroxy-3-methoxycyc; 4,5,6,8,11,12,13,14,15,16,17,18,19,24,25,26,26a-heptadecahydro-5,19-dihydroxy-3-; dimethoxy-4,10,12,18-tetramethyl-8-(2-propenyl)-,(3S,4R,5S,8R,12S,14S,15R,16S,18R,19R,26aS)-; lohexyl]-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)-; Tacrolimus solution, 1.0 mg/mL in acetonitrile, ampule of 1 mL, certified reference material
    Click to Show/Hide
Molecular Type
Small molecule
Disease Transplant rejection [ICD-11: NE84] Approved [1]
Structure
Click to Download Mol
2D MOL

3D MOL

    Click to Show/Hide the Molecular Information and External Link(s) of This Natural Product
Formula
C44H69NO12
PubChem CID
445643
Canonical SMILES
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
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
CAS Number
CAS 104987-11-3
ChEBI ID
CHEBI:61049
TTD Drug ID
D06OMK
DrugBank ID
DB00864
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Natural Product(s) Able to Enhance the Efficacy of This Drug
          Glucosamine      Homo sapiens     Click to Show/Hide the Molecular Data of This NP
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [2]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    In-vivo Model NC/Nga mice Induction of AD using Df body ointment was performed.
                    Experimental
                    Result(s)		 Combination therapy of glucosamine plus FK-506 was more synergistic efficacy than single-modality treatment with either alone to improve the development of established dermatitis in NC/Nga mice model.
          Mycophenolate mofetil      Penicillium stoloniferum     Click to Show/Hide the Molecular Data of This NP
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [3]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    In-vivo Model Clinical Trial
                    Experimental
                    Result(s)		 The introduction of MMF combined with the reduction of at least 50% of CNI dose allowed the renal function of liver transplant recipients to significantly improve at 1 year, without any rejection episode and without significant secondary effects.
Target and Pathway
Target(s) Calcineurin (PPP3CA)  Molecule Info  [4]
KEGG Pathway MAPK signaling pathway Click to Show/Hide
2 Calcium signaling pathway
3 cGMP-PKG signaling pathway
4 Oocyte meiosis
5 Apoptosis
6 Wnt signaling pathway
7 Axon guidance
8 VEGF signaling pathway
9 Osteoclast differentiation
10 Natural killer cell mediated cytotoxicity
11 T cell receptor signaling pathway
12 B cell receptor signaling pathway
13 Long-term potentiation
14 Glutamatergic synapse
15 Dopaminergic synapse
16 Oxytocin signaling pathway
17 Glucagon signaling pathway
18 Alzheimer's disease
19 Amyotrophic lateral sclerosis (ALS)
20 Amphetamine addiction
21 Tuberculosis
22 HTLV-I infection
Reactome DARPP-32 events Click to Show/Hide
2 FCERI mediated Ca+2 mobilization
3 Ca2+ pathway
WikiPathways Mitochondrial Gene Expression Click to Show/Hide
2 MAPK Signaling Pathway
3 G Protein Signaling Pathways
4 Cardiac Hypertrophic Response
5 Fc epsilon receptor (FCERI) signaling
6 Signaling by the B Cell Receptor (BCR)
7 T-Cell Receptor and Co-stimulatory Signaling
8 Amyotrophic lateral sclerosis (ALS)
9 Spinal Cord Injury
10 Alzheimers Disease
11 miR-targeted genes in muscle cell - TarBase
12 miR-targeted genes in lymphocytes - TarBase
13 Opioid Signalling
14 MicroRNAs in cardiomyocyte hypertrophy
15 Physiological and Pathological Hypertrophy of the Heart
References
Reference 1 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 6784).
Reference 2 Therapeutic effects of combination using glucosamine plus tacrolimus (FK-506) on the development of atopic dermatitis-like skin lesions in NC/Nga mice. Scand J Immunol. 2012 May;75(5):471-8.
Reference 3 Mycophenolate mofetil in combination with reduction of calcineurin inhibitors for chronic renal dysfunction after liver transplantation. Liver Transpl. 2006 Dec;12(12):1755-60.
Reference 4 Emerging drugs for ocular allergy. Expert Opin Emerg Drugs. 2005 Aug;10(3):505-20.
 Download Picture         KEGG Link