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Compound Detail

CHEMBL3989887

TACROLIMUS
💊 Approved Drug
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💊 Approved Drug
C=CC[C@@H]1/C=C(\C)C[C@H](C)C[C@H](OC)[C@H]2O[C@@](O)(C(=O)C(=O)N3CCCC[C@H]3C(=O)O[C@H](/C(C)=C/[C@@H]3CC[C@@H](O)[C@H](OC)C3)[C@H](C)[C@@H](O)CC1=O)[C@H](C)C[C@@H]2OC.O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL3989887
Name TACROLIMUS
Phase Approved
Structure Type MOL
InChI Key NWJQLQGQZSIBAF-MLAUYUEBSA-N
Therapeutic ✓ Yes
Parent Compound CHEMBL269732
Active Moiety CHEMBL269732

Known Names

Adoport Advagraf Astagraf xl Capexion Envarsus Envarsus xr FK 506 FK-506 FK506 FR-900506 FR900506 Modigraf +11 more
1
Targets
1
Activities
1
Assay Types
0
PK Parameters
16
Publications
23
Known Names
15
Indications
1
Mechanisms

Molecular Properties

804.0
MW (Da)
4.64
ALogP
12
HBA
3
HBD
178.4
PSA (Ų)
0.18
QED
2
Ro5 Violations
7
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1994
Availability Prescription
Chirality Single Enantiomer

Routes of Administration

Oral Parenteral Topical

Flags

Black Box Warning
USAN Stem -imus
USAN Year 1992

Extended Properties

Molecular Formula C44H71NO13
MW 822.05
Aromatic Rings 0
Heavy Atoms 57
NP-Likeness 1.42

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
FK506-binding protein 1A inhibitor INHIBITOR Peptidyl-prolyl cis-trans isomerase FKBP1A ✓ ✓

Indications

Delayed Graft Function Dermatitis, Atopic Eczema Immune System Diseases Kidney Transplantation Liver Transplantation Conjunctivitis, Allergic Keratoconjunctivitis Anemia, Aplastic Anemia, Sickle Cell Graft vs Host Disease Graft vs Host Disease Lichen Planus, Oral Thalassemia Hematologic Neoplasms

ATC Classification

D11AH01
tacrolimus
Level 1: DERMATOLOGICALS
Level 2: OTHER DERMATOLOGICAL PREPARATIONS
L04AD02
tacrolimus
Level 1: ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
Level 2: IMMUNOSUPPRESSANTS

Drug Warnings

Black Box Warning
carcinogenicity
Country: United States
Black Box Warning
immune system toxicity
Country: United States
Black Box Warning
infectious disease
Country: United States

Activity Summary

Ki 1 meas. best 8.0

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Peptidyl-prolyl cis-trans isomerase FKBP1A
CHEMBL1902
 Ki 8.0 8.0 10.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Peptidyl-prolyl cis-trans isomerase FKBP1A Ki = 10.0 nM 8.0 PPlase Assay: The assay was conducted at 10° C. in 50 mM Tris buffer at pH8.0, 5... -

Literature References

PubMed DOI Target Context # Activities
31158845 10.1038/s41586-019-1291-3 ADMET 113
- 10.1101/2024.03.28.586928 ADMET 100
- 10.5281/zenodo.13943903 ADMET 89
- 10.6019/CHEMBL5303304 HEK-293T 9
- 10.6019/CHEMBL5303304 U2OS 9
- 10.6019/CHEMBL5303304 Fibroblast 7
- 10.6019/CHEMBL5308504 Casein kinase I isoform delta 1
- 10.6019/CHEMBL5308504 Cyclin-dependent kinase 2 1
- 10.6019/CHEMBL5308504 Glycogen synthase kinase-3 beta 1
- 10.6019/CHEMBL5308504 Mitogen-activated protein kinase 1 1
- 10.6019/CHEMBL5308504 Aurora kinase A 1
- 10.6019/CHEMBL5308504 Tyrosine-protein kinase ABL1 1
- 10.6019/CHEMBL5308504 Fibroblast growth factor receptor 3 1
- 10.6019/CHEMBL5308504 Peregrin 1
- 10.6019/CHEMBL5308504 Transcription intermediary factor 1-alpha 1
- 10.6019/CHEMBL5308504 Bromodomain-containing protein 4 1

Data from ChEMBL 36 via Core Engine