Details of the Drug

General Information of Drug (ID: DMZLGRB)

Drug Name
Pimecrolimus
Synonyms Elidel; ASM 981; SDZ ASM 981; ASM-981; ASM-998; Elidel (TN); SDZ-ASM 981; Pimecrolimus [USAN:INN:BAN]; SDZ-ASM-981; Pimecrolimus (JAN/USAN/INN); 33-epi-Chloro-33-desoxyascomycin
Indication
Disease Entry ICD 11 Status REF
Atopic dermatitis EA80 Approved [1], [2]
Therapeutic Class
Dermatologic Agents
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 2 Molecular Weight (mw) 810.4
Topological Polar Surface Area (xlogp) 3.8
Rotatable Bond Count (rotbonds) 6
Hydrogen Bond Donor Count (hbonddonor) 2
Hydrogen Bond Acceptor Count (hbondacc) 11
ADMET Property
BDDCS Class
Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 2: low solubility and high permeability [3]
Elimination
0% of drug is excreted from urine in the unchanged form [3]
Metabolism
The drug is metabolized via skin [4]
MRTD
The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 0.6169 micromolar/kg/day [5]
Chemical Identifiers
Formula
C43H68ClNO11
IUPAC Name
(1R,9S,12S,13R,14S,17R,18E,21S,23S,24R,25S,27R)-12-[(E)-1-[(1R,3R,4S)-4-chloro-3-methoxycyclohexyl]prop-1-en-2-yl]-17-ethyl-1,14-dihydroxy-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-azatricyclo[22.3.1.04,9]octacos-18-ene-2,3,10,16-tetrone
Canonical SMILES
CC[C@@H]1/C=C(/C[C@@H](C[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](CC1=O)O)C)/C(=C/[C@@H]4CC[C@@H]([C@@H](C4)OC)Cl)/C)O)C)OC)OC)C)\\C
InChI
InChI=1S/C43H68ClNO11/c1-10-30-18-24(2)17-25(3)19-36(53-8)39-37(54-9)21-27(5)43(51,56-39)40(48)41(49)45-16-12-11-13-32(45)42(50)55-38(28(6)33(46)23-34(30)47)26(4)20-29-14-15-31(44)35(22-29)52-7/h18,20,25,27-33,35-39,46,51H,10-17,19,21-23H2,1-9H3/b24-18+,26-20+/t25-,27+,28+,29-,30+,31-,32-,33-,35+,36-,37-,38+,39+,43+/m0/s1
InChIKey
KASDHRXLYQOAKZ-XDSKOBMDSA-N
Cross-matching ID
PubChem CID
6509979
ChEBI ID
CHEBI:135888
CAS Number
137071-32-0
DrugBank ID
DB00337
TTD ID
D0Z4UN
INTEDE ID
DR1289

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Calcineurin (PPP3CA) TTA4LDE PP2BA_HUMAN Inhibitor [6]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 3A4 (CYP3A4) DE4LYSA CP3A4_HUMAN Substrate [7]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease Atopic dermatitis
ICD Disease Classification EA80
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Calcineurin (PPP3CA) DTT PPP3CA 5.29E-01 1.74E-03 9.99E-03
Cytochrome P450 3A4 (CYP3A4) DME CYP3A4 8.67E-01 -3.83E-03 -1.24E-02
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Disease Different from Pimecrolimus (Comorbidity)
DDI Drug Name DDI Drug ID Severity Mechanism Comorbidity REF
Dronedarone DMA8FS5 Minor Decreased metabolism of Pimecrolimus caused by Dronedarone mediated inhibition of CYP450 enzyme. Angina pectoris [BA40] [21]
Nifedipine DMSVOZT Minor Decreased metabolism of Pimecrolimus caused by Nifedipine mediated inhibition of CYP450 enzyme. Angina pectoris [BA40] [21]
Voriconazole DMAOL2S Minor Decreased metabolism of Pimecrolimus caused by Voriconazole mediated inhibition of CYP450 enzyme. Aspergillosis [1F20] [21]
Posaconazole DMUL5EW Minor Decreased metabolism of Pimecrolimus caused by Posaconazole mediated inhibition of CYP450 enzyme. Aspergillosis [1F20] [21]
Zafirlukast DMHNQOG Minor Decreased metabolism of Pimecrolimus caused by Zafirlukast mediated inhibition of CYP450 enzyme. Asthma [CA23] [21]
Ciprofloxacin XR DM2NLS9 Minor Decreased metabolism of Pimecrolimus caused by Ciprofloxacin XR mediated inhibition of CYP450 enzyme. Bacterial infection [1A00-1C4Z] [21]
Dalfopristin DM4LTKV Minor Decreased metabolism of Pimecrolimus caused by Dalfopristin mediated inhibition of CYP450 enzyme. Bacterial infection [1A00-1C4Z] [21]
Clarithromycin DM4M1SG Minor Decreased metabolism of Pimecrolimus caused by Clarithromycin mediated inhibition of CYP450 enzyme. Bacterial infection [1A00-1C4Z] [21]
Chloramphenicol DMFXEWT Minor Decreased metabolism of Pimecrolimus caused by Chloramphenicol mediated inhibition of CYP450 enzyme. Bacterial infection [1A00-1C4Z] [21]
Troleandomycin DMUZNIG Minor Decreased metabolism of Pimecrolimus caused by Troleandomycin mediated inhibition of CYP450 enzyme. Bacterial infection [1A00-1C4Z] [21]
Telithromycin DMZ4P3A Minor Decreased metabolism of Pimecrolimus caused by Telithromycin mediated inhibition of CYP450 enzyme. Bacterial infection [1A00-1C4Z] [21]
Pexidartinib DMS2J0Z Moderate Increased metabolism of Pimecrolimus caused by Pexidartinib mediated induction of CYP450 enzyme. Bone/articular cartilage neoplasm [2F7B] [22]
Lapatinib DM3BH1Y Minor Decreased metabolism of Pimecrolimus caused by Lapatinib mediated inhibition of CYP450 enzyme. Breast cancer [2C60-2C6Y] [21]
Tucatinib DMBESUA Minor Decreased metabolism of Pimecrolimus caused by Tucatinib mediated inhibition of CYP450 enzyme. Breast cancer [2C60-2C6Y] [21]
Grepafloxacin DMGLX0T Minor Decreased metabolism of Pimecrolimus caused by Grepafloxacin mediated inhibition of CYP450 enzyme. Bronchitis [CA20] [21]
Mifepristone DMGZQEF Minor Decreased metabolism of Pimecrolimus caused by Mifepristone mediated inhibition of CYP450 enzyme. Cushing syndrome [5A70] [21]
Ivacaftor DMZC1HS Minor Decreased metabolism of Pimecrolimus caused by Ivacaftor mediated inhibition of CYP450 enzyme. Cystic fibrosis [CA25] [21]
MK-8228 DMOB58Q Minor Decreased metabolism of Pimecrolimus caused by MK-8228 mediated inhibition of CYP450 enzyme. Cytomegaloviral disease [1D82] [21]
Aprepitant DM053KT Minor Decreased metabolism of Pimecrolimus caused by Aprepitant mediated inhibition of CYP450 enzyme. Depression [6A70-6A7Z] [21]
Nefazodone DM4ZS8M Minor Decreased metabolism of Pimecrolimus caused by Nefazodone mediated inhibition of CYP450 enzyme. Depression [6A70-6A7Z] [21]
Stiripentol DMMSDOY Minor Decreased metabolism of Pimecrolimus caused by Stiripentol mediated inhibition of CYP450 enzyme. Epilepsy/seizure [8A61-8A6Z] [21]
Itraconazole DMCR1MV Minor Decreased metabolism of Pimecrolimus caused by Itraconazole mediated inhibition of CYP450 enzyme. Fungal infection [1F29-1F2F] [21]
Miconazole DMPMYE8 Minor Decreased metabolism of Pimecrolimus caused by Miconazole mediated inhibition of CYP450 enzyme. Fungal infection [1F29-1F2F] [21]
Ketoconazole DMPZI3Q Minor Decreased metabolism of Pimecrolimus caused by Ketoconazole mediated inhibition of CYP450 enzyme. Fungal infection [1F29-1F2F] [21]
Cimetidine DMH61ZB Minor Decreased metabolism of Pimecrolimus caused by Cimetidine mediated inhibition of CYP450 enzyme. Gastro-oesophageal reflux disease [DA22] [21]
Boceprevir DMBSHMF Minor Decreased metabolism of Pimecrolimus caused by Boceprevir mediated inhibition of CYP450 enzyme. Hepatitis virus infection [1E50-1E51] [21]
Telaprevir DMMRV29 Minor Decreased metabolism of Pimecrolimus caused by Telaprevir mediated inhibition of CYP450 enzyme. Hepatitis virus infection [1E50-1E51] [21]
Isoniazid DM5JVS3 Minor Decreased metabolism of Pimecrolimus caused by Isoniazid mediated inhibition of CYP450 enzyme. HIV-infected patients with tuberculosis [1B10-1B14] [21]
Delavirdine DM3NF5G Minor Decreased metabolism of Pimecrolimus caused by Delavirdine mediated inhibition of CYP450 enzyme. Human immunodeficiency virus disease [1C60-1C62] [21]
Fosamprenavir DM4W9B3 Minor Decreased metabolism of Pimecrolimus caused by Fosamprenavir mediated inhibition of CYP450 enzyme. Human immunodeficiency virus disease [1C60-1C62] [21]
Cobicistat DM6L4H2 Minor Decreased metabolism of Pimecrolimus caused by Cobicistat mediated inhibition of CYP450 enzyme. Human immunodeficiency virus disease [1C60-1C62] [21]
Saquinavir DMG814N Minor Decreased metabolism of Pimecrolimus caused by Saquinavir mediated inhibition of CYP450 enzyme. Human immunodeficiency virus disease [1C60-1C62] [21]
Amprenavir DMLMXE0 Minor Decreased metabolism of Pimecrolimus caused by Amprenavir mediated inhibition of CYP450 enzyme. Human immunodeficiency virus disease [1C60-1C62] [21]
Darunavir DMN3GCH Minor Decreased metabolism of Pimecrolimus caused by Darunavir mediated inhibition of CYP450 enzyme. Human immunodeficiency virus disease [1C60-1C62] [21]
Atazanavir DMSYRBX Minor Decreased metabolism of Pimecrolimus caused by Atazanavir mediated inhibition of CYP450 enzyme. Human immunodeficiency virus disease [1C60-1C62] [21]
Ritonavir DMU764S Minor Decreased metabolism of Pimecrolimus caused by Ritonavir mediated inhibition of CYP450 enzyme. Human immunodeficiency virus disease [1C60-1C62] [21]
Verapamil DMA7PEW Minor Decreased metabolism of Pimecrolimus caused by Verapamil mediated inhibition of CYP450 enzyme. Hypertension [BA00-BA04] [21]
Diltiazem DMAI7ZV Minor Decreased metabolism of Pimecrolimus caused by Diltiazem mediated inhibition of CYP450 enzyme. Hypertension [BA00-BA04] [21]
Conivaptan DM1V329 Minor Decreased metabolism of Pimecrolimus caused by Conivaptan mediated inhibition of CYP450 enzyme. Hypo-osmolality/hyponatraemia [5C72] [21]
Berotralstat DMWA2DZ Minor Decreased metabolism of Pimecrolimus caused by Berotralstat mediated inhibition of CYP450 enzyme. Innate/adaptive immunodeficiency [4A00] [21]
Crizotinib DM4F29C Minor Decreased metabolism of Pimecrolimus caused by Crizotinib mediated inhibition of CYP450 enzyme. Lung cancer [2C25] [21]
Selpercatinib DMZR15V Minor Decreased metabolism of Pimecrolimus caused by Selpercatinib mediated inhibition of CYP450 enzyme. Lung cancer [2C25] [21]
Idelalisib DM602WT Minor Decreased metabolism of Pimecrolimus caused by Idelalisib mediated inhibition of CYP450 enzyme. Mature B-cell leukaemia [2A82] [21]
IPI-145 DMWA24P Minor Decreased metabolism of Pimecrolimus caused by IPI-145 mediated inhibition of CYP450 enzyme. Mature B-cell leukaemia [2A82] [21]
Danazol DML8KTN Minor Decreased metabolism of Pimecrolimus caused by Danazol mediated inhibition of CYP450 enzyme. Menstrual cycle bleeding disorder [GA20] [21]
Fedratinib DM4ZBK6 Minor Decreased metabolism of Pimecrolimus caused by Fedratinib mediated inhibition of CYP450 enzyme. Myeloproliferative neoplasm [2A20] [21]
Nilotinib DM7HXWT Minor Decreased metabolism of Pimecrolimus caused by Nilotinib mediated inhibition of CYP450 enzyme. Myeloproliferative neoplasm [2A20] [21]
Imatinib DM7RJXL Minor Decreased metabolism of Pimecrolimus caused by Imatinib mediated inhibition of CYP450 enzyme. Myeloproliferative neoplasm [2A20] [21]
Dasatinib DMJV2EK Minor Decreased metabolism of Pimecrolimus caused by Dasatinib mediated inhibition of CYP450 enzyme. Myeloproliferative neoplasm [2A20] [21]
Netupitant DMEKAYI Minor Decreased metabolism of Pimecrolimus caused by Netupitant mediated inhibition of CYP450 enzyme. Nausea/vomiting [MD90] [21]
Entrectinib DMMPTLH Minor Decreased metabolism of Pimecrolimus caused by Entrectinib mediated inhibition of CYP450 enzyme. Non-small cell lung cancer [2C25] [21]
Rucaparib DM9PVX8 Minor Decreased metabolism of Pimecrolimus caused by Rucaparib mediated inhibition of CYP450 enzyme. Ovarian cancer [2C73] [21]
Abametapir DM2RX0I Moderate Decreased metabolism of Pimecrolimus caused by Abametapir mediated inhibition of CYP450 enzyme. Pediculosis [1G00] [23]
Lonafarnib DMGM2Z6 Minor Decreased metabolism of Pimecrolimus caused by Lonafarnib mediated inhibition of CYP450 enzyme. Premature ageing appearance [LD2B] [21]
Bicalutamide DMZMSPF Minor Decreased metabolism of Pimecrolimus caused by Bicalutamide mediated inhibition of CYP450 enzyme. Prostate cancer [2C82] [21]
Temsirolimus DMS104F Moderate Increased plasma concentrations of Pimecrolimus and Temsirolimus due to competitive inhibition of the same metabolic pathway. Renal cell carcinoma [2C90] [24]
Voxelotor DMCS6M5 Minor Decreased metabolism of Pimecrolimus caused by Voxelotor mediated inhibition of CYP450 enzyme. Sickle-cell disorder [3A51] [21]
Larotrectinib DM26CQR Minor Decreased metabolism of Pimecrolimus caused by Larotrectinib mediated inhibition of CYP450 enzyme. Solid tumour/cancer [2A00-2F9Z] [21]
LEE011 DMMX75K Minor Decreased metabolism of Pimecrolimus caused by LEE011 mediated inhibition of CYP450 enzyme. Solid tumour/cancer [2A00-2F9Z] [21]
Fostamatinib DM6AUHV Moderate Decreased metabolism of Pimecrolimus caused by Fostamatinib mediated inhibition of CYP450 enzyme. Thrombocytopenia [3B64] [25]
Brilinta DMBR01X Minor Decreased metabolism of Pimecrolimus caused by Brilinta mediated inhibition of CYP450 enzyme. Thrombosis [DB61-GB90] [21]
Sirolimus DMGW1ID Moderate Increased plasma concentrations of Pimecrolimus and Sirolimus due to competitive inhibition of the same metabolic pathway. Transplant rejection [NE84] [24]
Tacrolimus DMZ7XNQ Moderate Increased plasma concentrations of Pimecrolimus and Tacrolimus due to competitive inhibition of the same metabolic pathway. Transplant rejection [NE84] [24]
⏷ Show the Full List of 63 DDI Information of This Drug

References

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21 Product Information. Elidel (pimecrolimus topical). Novartis Pharmaceuticals, East Hanover, NJ.
22 Product Information. Sonata (zaleplon) Wyeth-Ayerst Laboratories, Philadelphia, PA.
23 Product Information. Xeglyze (abametapir topical). Dr. Reddy's Laboratories Inc, Upper Saddle River, NJ.
24 Product Information. Prograf (tacrolimus). Fujisawa, Deerfield, IL.
25 Product Information. Tavalisse (fostamatinib). Rigel Pharmaceuticals, South San Francisco, CA.