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Compound Detail

CHEMBL1200686

PIMECROLIMUS
💊 Approved Drug
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💊 Approved Drug
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](Cl)[C@H](OC)C3)[C@H](C)[C@@H](O)CC1=O)[C@H](C)C[C@@H]2OC
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1200686
Name PIMECROLIMUS
Phase Approved
Structure Type MOL
InChI Key KASDHRXLYQOAKZ-XDSKOBMDSA-N
Therapeutic ✓ Yes

Known Names

(-)-pimecrolimus Elidel Pimecrolimus SDZ ASM 981 SDZ ASM-981 SDZ-ASM 981 SDZ-ASM-981
1
Targets
1
Activities
1
Assay Types
1
PK Parameters
20
Publications
7
Known Names
11
Indications
1
Mechanisms

Molecular Properties

810.5
MW (Da)
5.72
ALogP
11
HBA
2
HBD
158.1
PSA (Ų)
0.15
QED
3
Ro5 Violations
6
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 2001
Availability Prescription
Chirality Single Enantiomer

Routes of Administration

Topical

Flags

Black Box Warning Natural Product
USAN Stem -imus
USAN Year 2000

Extended Properties

Molecular Formula C43H68ClNO11
MW 810.47
Aromatic Rings 0
Heavy Atoms 56
NP-Likeness 1.33

Mechanism of Action

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

Indications

Dermatitis, Atopic Eczema Dermatitis Dermatitis, Perioral Lichen Planus Dermatitis, Seborrheic Dry Eye Syndromes Lichen Planus, Oral Lichen Sclerosus et Atrophicus Vitiligo Netherton Syndrome

ATC Classification

D11AH02
pimecrolimus
Level 1: DERMATOLOGICALS
Level 2: OTHER DERMATOLOGICAL PREPARATIONS

Drug Warnings

Black Box Warning
carcinogenicity
Country: United States

Activity Summary

IC50 1 meas. best 5.0

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Bile salt export pump
CHEMBL6020
 IC50 5.0 5.0 10000.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 18.64 ng.hr.mL-1 Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Bile salt export pump IC50 = 10000.0 nM 5.0 Inhibition of human BSEP overexpressed in Sf9 cell membrane vesicles assessed as... 23956101

Literature References

PubMed DOI Target Context # Activities
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
37468498 10.1038/s41467-023-40064-9 Thromboxane A2 receptor 2
37468498 10.1038/s41467-023-40064-9 Prostaglandin G/H synthase 1 2
23956101 10.1093/toxsci/kft176 Homo sapiens 2
37468498 10.1038/s41467-023-40064-9 Alpha-1A adrenergic receptor 2
37468498 10.1038/s41467-023-40064-9 Muscarinic acetylcholine receptor M1 2
37468498 10.1038/s41467-023-40064-9 Sodium-dependent dopamine transporter 1
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 1A 1
37468498 10.1038/s41467-023-40064-9 Amine oxidase [flavin-containing] A 1
37468498 10.1038/s41467-023-40064-9 Alpha-2A adrenergic receptor 1
37468498 10.1038/s41467-023-40064-9 Sodium-dependent serotonin transporter 1
37468498 10.1038/s41467-023-40064-9 Sodium-dependent noradrenaline transporter 1
37468498 10.1038/s41467-023-40064-9 Acetylcholinesterase 1
37468498 10.1038/s41467-023-40064-9 Estrogen receptor 1
37468498 10.1038/s41467-023-40064-9 D(1A) dopamine receptor 1
- 10.1101/2020.04.21.054387 SARS-CoV-2 1
23956101 10.1093/toxsci/kft176 Unchecked 1
23956101 10.1093/toxsci/kft176 ATP-binding cassette sub-family C member 4 1
23956101 10.1093/toxsci/kft176 ATP-binding cassette sub-family C member 3 1
23956101 10.1093/toxsci/kft176 ATP-binding cassette sub-family C member 2 1

Data from ChEMBL 36 via Core Engine