pimecrolimus ๐Ÿถ Veterinary Use | 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 ยตM/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 85.82 23.94 22 2186 3776 50599140
Steroid withdrawal syndrome 63.15 23.94 12 2196 515 50602401
Application site erythema 54.53 23.94 16 2192 4522 50598394
Psoriasis 54.11 23.94 35 2173 68965 50533951
Eczema 50.44 23.94 23 2185 22679 50580237
Dermatitis atopic 40.27 23.94 12 2196 3574 50599342
Application site pruritus 39.71 23.94 12 2196 3747 50599169
Application site irritation 39.65 23.94 10 2198 1605 50601311
Skin burning sensation 31.37 23.94 13 2195 10172 50592744
Vulval disorder 30.99 23.94 7 2201 703 50602213
Skin exfoliation 28.66 23.94 18 2190 33594 50569322
Application site swelling 27.76 23.94 6 2202 492 50602424
Application site dryness 27.58 23.94 5 2203 165 50602751
Pruritus 27.04 23.94 46 2162 283522 50319394
Lymphadenopathy 26.23 23.94 17 2191 33482 50569434

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 41.88 30.75 10 984 1669 29571864
Dermatitis atopic 39.11 30.75 10 984 2209 29571324
Limbic encephalitis 37.33 30.75 7 987 365 29573168

FDA Adverse Event Reporting System (Geriatric)

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 107.76 24.18 26 2302 4222 64492182
Steroid withdrawal syndrome 95.04 24.18 17 2311 633 64495771
Application site erythema 70.94 24.18 19 2309 4670 64491734
Limbic encephalitis 44.30 24.18 9 2319 662 64495742
Eczema 42.62 24.18 21 2307 29699 64466705
Dermatitis atopic 41.59 24.18 12 2316 3864 64492540
Application site pruritus 38.17 24.18 11 2317 3528 64492876
Skin burning sensation 36.84 24.18 14 2314 10569 64485835
Application site irritation 36.65 24.18 9 2319 1567 64494837
Pruritus 33.10 24.18 48 2280 312352 64184052
Application site vesicles 33.04 24.18 8 2320 1314 64495090
Application site swelling 33.01 24.18 7 2321 635 64495769
Psoriasis 32.14 24.18 24 2304 71679 64424725
Ocular hyperaemia 29.56 24.18 15 2313 22549 64473855
Erythema 29.52 24.18 35 2293 187035 64309369
Application site dryness 28.13 24.18 5 2323 179 64496225
Application site dermatitis 28.10 24.18 5 2323 180 64496224
Skin exfoliation 27.02 24.18 18 2310 44867 64451537
Eye swelling 26.84 24.18 14 2314 22267 64474137
Application site discolouration 26.69 24.18 6 2322 714 64495690
Lymphadenopathy 26.38 24.18 18 2310 46668 64449736
Eye pruritus 24.47 24.18 11 2317 12648 64483756

FDA Adverse Event Reporting System (Pediatric)

None

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 | Suggest Off label Use Form| |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




๐Ÿถ Veterinary Drug Use

None

๐Ÿถ Veterinary products

None

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
Interleukin-5 Cytokine WOMBAT-PK
Interferon gamma Cytokine WOMBAT-PK
Interleukin-2 Cytokine WOMBAT-PK
Serine/threonine-protein phosphatase 2B catalytic subunit gamma isoform Enzyme WOMBAT-PK
Peptidyl-prolyl cis-trans isomerase FKBP1A Enzyme INHIBITOR IC50 8.22 IUPHAR

External reference:

IDSource
4021291 VUID
N0000148728 NUI
D05480 KEGG_DRUG
4021291 VANDF
C1099414 UMLSCUI
CHEBI:135888 CHEBI
CHEMBL1200686 ChEMBL_ID
DB00337 DRUGBANK_ID
C117268 MESH_SUPPLEMENTAL_RECORD_UI
6783 IUPHAR_LIGAND_ID
7632 INN_ID
7KYV510875 UNII
6509979 PUBCHEM_CID
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