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

Stem definition	Drug id	CAS RN
immunosuppressants, rapamycin derivatives	2168	137071-32-0

Description:

Molecule	Description
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

Molecule

Description

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:

Property	Value	Reference
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 µM/kg/day	Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability)	0 %	Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H

Approvals:

Date	Agency	Company	Orphan
Dec. 13, 2001	FDA	VALEANT BERMUDA

FDA Adverse Event Reporting System (Female)

MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Application site pain	86.44	23.96	22	2033	4161	53342850
Steroid withdrawal syndrome	63.68	23.96	12	2043	559	53346452
Psoriasis	60.34	23.96	39	2016	87050	53259961
Application site erythema	54.68	23.96	16	2039	5075	53341936
Eczema	42.35	23.96	20	2035	24162	53322849
Application site pruritus	40.02	23.96	12	2043	4137	53342874
Application site irritation	39.46	23.96	10	2045	1854	53345157
Dermatitis atopic	36.59	23.96	11	2044	3823	53343188
Vulval disorder	31.44	23.96	7	2048	747	53346264
Skin burning sensation	31.29	23.96	13	2042	11597	53335414
Application site dryness	28.06	23.96	5	2050	170	53346841
Application site swelling	27.65	23.96	6	2049	568	53346443
Lymphadenopathy	26.94	23.96	17	2038	36238	53310773

FDA Adverse Event Reporting System (Male)

MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Application site pain	42.63	31.94	10	949	1764	32510803
Dermatitis atopic	39.36	31.94	10	949	2457	32510110
Limbic encephalitis	38.71	31.94	7	952	341	32512226

Pharmacologic Action:

Source	Code	Description
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)

Disease	Relation	SNOMED_ID	DOID
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 level	Dissociation constant	Type (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:

Target	Class	Pharos	UniProt	Action	Type	Activity value (-log[M])	Bioact source	MoA source
Peptidyl-prolyl cis-trans isomerase FKBP1A	Enzyme	P62942	FKB1A_HUMAN	INHIBITOR	Kd	9	WOMBAT-PK	CHEMBL
Interleukin-5	Cytokine	P05113	IL5_HUMAN				WOMBAT-PK
Interferon gamma	Cytokine	P01579	IFNG_HUMAN				WOMBAT-PK
Interleukin-2	Cytokine	P60568	IL2_HUMAN				WOMBAT-PK
Serine/threonine-protein phosphatase 2B catalytic subunit gamma isoform	Enzyme	P48454	PP2BC_HUMAN				WOMBAT-PK
Peptidyl-prolyl cis-trans isomerase FKBP1A	Enzyme		FKB1A_RAT	INHIBITOR	IC50	8.22	IUPHAR

External reference:

ID	Source
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:

Product	Category	Ingredients	NDC	Form	Quantity	Route	Marketing	Label
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