pimecrolimus Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
immunosuppressants, rapamycin derivatives 2168 137071-32-0

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • elidel
  • pimecrolimus
  • picrolimus
an ascomycin derivative; mechanism of action involves calcineurin inhibition, blockage of T cell activation, blocking signal transduction pathways in T cells, and inhibition of the synthesis of inflammatory cytokines, specifically Th1- and Th2-type cytokines
  • Molecular weight: 810.46
  • Formula: C43H68ClNO11
  • CLOGP: 7.10
  • LIPINSKI: 3
  • HAC: 12
  • HDO: 2
  • TPSA: 158.13
  • ALOGS: -5.73
  • ROTB: 6

  • Status: OFP

  • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

None

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 2 Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 0 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 0.62 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 0 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H

Approvals:

DateAgencyCompanyOrphan
Dec. 13, 2001 FDA VALEANT BERMUDA

FDA Adverse Event Reporting System (Female)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Application site pain 86.77 23.18 22 1821 4001 46680218
Psoriasis 58.12 23.18 37 1806 78567 46605652
Application site erythema 54.90 23.18 16 1827 4888 46679331
Steroid withdrawal syndrome 52.51 23.18 10 1833 481 46683738
Eczema 41.95 23.18 19 1824 20381 46663838
Application site pruritus 40.13 23.18 12 1831 4001 46680218
Application site irritation 39.46 23.18 10 1833 1809 46682410
Application site dryness 28.11 23.18 5 1838 164 46684055
Lymphadenopathy 27.81 23.18 17 1826 33471 46650748
Application site swelling 27.53 23.18 6 1837 566 46683653
Skin burning sensation 25.32 23.18 11 1832 10681 46673538

FDA Adverse Event Reporting System (Male)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Application site pain 43.26 28.90 10 875 1653 29949940
Dermatitis atopic 36.38 28.90 8 877 1056 29950537
Application site erythema 30.24 28.90 8 877 2295 29949298
Insulin resistance 29.38 28.90 6 879 556 29951037

Pharmacologic Action:

SourceCodeDescription
ATC D11AH02 DERMATOLOGICALS
OTHER DERMATOLOGICAL PREPARATIONS
OTHER DERMATOLOGICAL PREPARATIONS
Agents for dermatitis, excluding corticosteroids
FDA EPC N0000175457 Calcineurin Inhibitor Immunosuppressant
FDA MoA N0000175458 Calcineurin Inhibitors
MeSH PA D000700 Analgesics
MeSH PA D018712 Analgesics, Non-Narcotic
MeSH PA D000893 Anti-Inflammatory Agents
MeSH PA D000894 Anti-Inflammatory Agents, Non-Steroidal
MeSH PA D018501 Antirheumatic Agents
MeSH PA D065095 Calcineurin Inhibitors
MeSH PA D003879 Dermatologic Agents
MeSH PA D004791 Enzyme Inhibitors
MeSH PA D007155 Immunologic Factors
MeSH PA D007166 Immunosuppressive Agents
MeSH PA D018373 Peripheral Nervous System Agents
MeSH PA D018689 Sensory System Agents

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Atopic dermatitis indication 24079001 DOID:3310
Intractable Eczema indication
Herpes zoster contraindication 4740000 DOID:8536
Lymphadenopathy contraindication 30746006
Immunosuppression contraindication 38013005
Varicella contraindication 38907003 DOID:8659
Verruca vulgaris contraindication 57019003 DOID:11165
Herpes simplex contraindication 88594005 DOID:8566
Viral infection of skin contraindication 128937004
Eczema herpeticum contraindication 186535001 DOID:9123
Infectious mononucleosis contraindication 271558008 DOID:8568
Netherton's syndrome contraindication 312514006
Impetiginized atopic dermatitis contraindication 402201001
Pre-Malignant Skin Lesion contraindication

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 12.4 acidic
pKa2 13.57 acidic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Peptidyl-prolyl cis-trans isomerase FKBP1A Enzyme INHIBITOR Kd 9 WOMBAT-PK CHEMBL
Serine/threonine-protein phosphatase 2B catalytic subunit gamma isoform Enzyme WOMBAT-PK
Interleukin-2 Cytokine WOMBAT-PK
Interferon gamma Cytokine WOMBAT-PK
Interleukin-5 Cytokine WOMBAT-PK
Peptidyl-prolyl cis-trans isomerase FKBP1A Unclassified INHIBITOR IC50 8.22 IUPHAR

External reference:

IDSource
4021291 VUID
N0000148728 NUI
D05480 KEGG_DRUG
4021291 VANDF
C0971833 UMLSCUI
CHEBI:135888 CHEBI
CHEMBL1200686 ChEMBL_ID
DB00337 DRUGBANK_ID
C117268 MESH_SUPPLEMENTAL_RECORD_UI
6509979 PUBCHEM_CID
6783 IUPHAR_LIGAND_ID
7632 INN_ID
7KYV510875 UNII
306865 RXNORM
16235 MMSL
302773 MMSL
42597 MMSL
009525 NDDF
385580005 SNOMEDCT_US
385581009 SNOMEDCT_US

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
ELIDEL HUMAN PRESCRIPTION DRUG LABEL 1 0187-5100 CREAM 10 mg TOPICAL NDA 27 sections
ELIDEL HUMAN PRESCRIPTION DRUG LABEL 1 0187-5101 CREAM 10 mg TOPICAL NDA 27 sections
ELIDEL HUMAN PRESCRIPTION DRUG LABEL 1 0187-5102 CREAM 10 mg TOPICAL NDA 27 sections
ELIDEL HUMAN PRESCRIPTION DRUG LABEL 1 0187-5103 CREAM 10 mg TOPICAL NDA 27 sections
pimecrolimus HUMAN PRESCRIPTION DRUG LABEL 1 0591-2944 CREAM 10 mg TOPICAL ANDA 25 sections
Elidel HUMAN PRESCRIPTION DRUG LABEL 1 54868-4878 CREAM 10 mg TOPICAL NDA 25 sections
Pimecrolimus HUMAN PRESCRIPTION DRUG LABEL 1 68462-609 CREAM 10 mg TOPICAL ANDA 25 sections
Pimecrolimus HUMAN PRESCRIPTION DRUG LABEL 1 68682-110 CREAM 10 mg TOPICAL NDA authorized generic 27 sections
Pimecrolimus HUMAN PRESCRIPTION DRUG LABEL 1 68682-111 CREAM 10 mg TOPICAL NDA authorized generic 27 sections
Pimecrolimus HUMAN PRESCRIPTION DRUG LABEL 1 68682-112 CREAM 10 mg TOPICAL NDA authorized generic 27 sections
pimecrolimus HUMAN PRESCRIPTION DRUG LABEL 1 70518-2292 CREAM 10 mg TOPICAL ANDA 25 sections