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Compound Report Card

Compound Name and Classification

Compound ID CHEMBL269732
CHEMBL269732
Compound Name TACROLIMUS
ChEMBL Synonyms FK-506 | PROTOPIC | TACROLIMUS HYDRATE | TACROLIMUS | FR-900506 | FK 506 | FR900506 | PROGRAF
Max Phase 4 (Approved)
Trade Names PROGRAF | PROTOPIC | TACROLIMUS
Molecular Formula C44H69NO12

Additional synonyms for CHEMBL269732 found using NCI Chemical Identifier Resolver

Compound Representations

Molfile Download MolFile
Canonical SMILES CO[C@@H]1C[C@@H](CC[C@H]1O)\C=C(/C)\[C@H]2OC(=O)[C@@H]3CCCCN ...
Download SMILES
Standard InChI InChI=1S/C44H69NO12/c1-10-13-31-19-25(2)18-26(3)20-37(54-8)4 ...
Download InChI
Standard InChI Key QJJXYPPXXYFBGM-LFZNUXCKSA-N

Sources

  • British National Formulary
  • Curated Drug Metabolism Pathways
  • DrugMatrix
  • Gene Expression Atlas Compounds
  • Orange Book
  • PubChem BioAssays
  • Scientific Literature
  • TP-search Transporter Database
  • USP Dictionary of USAN and International Drug Names
  • WHO Anatomical Therapeutic Chemical Classification

Alternate Forms of Compound in ChEMBL


CHEMBL269732

Molecule Features

CHEMBL269732 compound icon
Drug Type:Natural Product-derived Rule of Five:N First In Class:N Chirality:Single Stereoisomer Prodrug:N Oral:Y Parenteral:Y Topical:Y Black Box:Y Availability Type:Prescription-only

Mechanism of Action

Mechanism of Action ChEMBL Target References
FK506-binding protein 1A inhibitor FK506-binding protein 1A DailyMed

Indications

MESH Heading MESH ID EFO ID EFO Term Max phase for indication References
DERMATITIS, ATOPICD003876EFO:0000274ATOPIC ECZEMA3ClinicalTrials
COLITIS, ULCERATIVED003093EFO:0000729ULCERATIVE COLITIS3ClinicalTrials
ECZEMAD004485HP:0000964ECZEMA4ATC
GLOMERULONEPHRITIS, IGAD005922EFO:0004194IGA GLOMERULONEPHRITIS2ClinicalTrials
LIVER FAILURED017093HP:0001399LIVER FAILURE2ClinicalTrials
HYPERTENSION, PULMONARYD006976EFO:0001361PULMONARY HYPERTENSION2ClinicalTrials
CROHN DISEASED003424EFO:0000384CROHN'S DISEASE2ClinicalTrials
GRAFT VS HOST DISEASED006086EFO:0004599ACUTE GRAFT VS. HOST DISEASE2ClinicalTrials
IMMUNE SYSTEM DISEASESD007154EFO:0000540IMMUNE SYSTEM DISEASE4ATC
KIDNEY DISEASESD007674EFO:0003086KIDNEY DISEASE2ClinicalTrials
WOUNDS AND INJURIESD014947EFO:0000546INJURY2ClinicalTrials
BRONCHIOLITIS OBLITERANSD001989EFO:0007183BRONCHIOLITIS OBLITERANS3ClinicalTrials
DERMATITIS, SEBORRHEICD012628EFO:1000764SEBORRHEIC DERMATITIS3ClinicalTrials
HEPATITIS CD006526EFO:0003047HEPATITIS C INFECTION2ClinicalTrials
LUPUS ERYTHEMATOSUS, SYSTEMICD008180EFO:0002690SYSTEMIC LUPUS ERYTHEMATOSUS3ClinicalTrials
SCLERODERMA, SYSTEMICD012595EFO:0000717SYSTEMIC SCLERODERMA1ClinicalTrials
COLITISD003092EFO:0003872COLITIS2ClinicalTrials
DIABETES MELLITUSD003920EFO:0000400DIABETES MELLITUS2ClinicalTrials
LIVER DISEASESD008107EFO:0001421LIVER DISEASE2ClinicalTrials
MYASTHENIA GRAVISD009157EFO:0004991MYASTHENIA GRAVIS3ClinicalTrials
VITILIGOD014820EFO:0004208VITILIGO3ClinicalTrials
CONJUNCTIVITIS, ALLERGICD003233EFO:0007141ALLERGIC CONJUNCTIVITIS2ClinicalTrials
LICHEN PLANUSD008010EFO:1000726LICHEN PLANUS2ClinicalTrials
NEPHROTIC SYNDROMED009404EFO:0004255NEPHROTIC SYNDROME3ClinicalTrials

Clinical Data

ClinicalTrials.gov TACROLIMUS
The Cochrane Collaboration TACROLIMUS

Metabolites for CHEMBL269732

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Compound Bioactivity Summary

Compound Assay Summary

Compound Target Summary

Calculated Compound Parent Properties

Mol. Weight Mol. Weight Monoisotopic ALogP #Rotatable Bonds Polar Surface Area Molecular Species
804 803.482 4.83 7 178.36 NEUTRAL


HBA HBD #Ro5 Violations HBA (Lipinski) HBD (Lipinski) #Ro5 Violations (Lipinski)
12 3 2 13 3 1


ACD Acidic pKa ACD Basic pKa ACD LogP ACD LogD pH7.4 Aromatic Rings Heavy Atoms QED Weighted
9.97 - 4.79 4.78 0 57 0.18

Structural Alerts

There are 7 structural alerts for CHEMBL269732. To view alerts please click here.

Compound Cross References

ATC L - ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
L04 - IMMUNOSUPPRESSANTS
L04A - IMMUNOSUPPRESSANTS
L04AD - Calcineurin inhibitors
L04AD02 - tacrolimus

D - DERMATOLOGICALS
D11 - OTHER DERMATOLOGICAL PREPARATIONS
D11A - OTHER DERMATOLOGICAL PREPARATIONS
D11AH - Agents for dermatitis, excluding corticosteroids
D11AH01 - tacrolimus

ChemSpider ChemSpider:QJJXYPPXXYFBGM-LFZNUXCKSA-N
DailyMed tacrolimus
PubChem SID: 144205609 SID: 50111459

UniChem Cross References

View the UniChem Connectivity matches for CHEMBL269732



ACToR 104987-11-3
Atlas tacrolimus
BindingDB 50030448
Brenda 5400 5545
ChEBI 61049
DrugBank DB00864
eMolecules 26941752
EPA CompTox Dashboard DTXSID5046354
FDA SRS Y5L2157C4J
Guide to Pharmacology 6784
KEGG Ligand C01375
LINCS LSM-43009
LipidMaps LMPK04000003
Metabolights MTBLC61049
MolPort MolPort-003-666-518
Nikkaji J313.679E
PDBe FK5
PharmGKB PA451578
PubChem 445643
PubChem: Drugs of the Future 12013904
PubChem: Thomson Pharma 14889261 14815954
Selleck FK-506-(Tacrolimus)
SureChEMBL SCHEMBL3088
ZINC ZINC000169289411

UniChem REST Service Call:
https://www.ebi.ac.uk/unichem/rest/verbose_inchikey/QJJXYPPXXYFBGM-LFZNUXCKSA-N spacer
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