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pimecrolimus 🐶 Veterinary Use | 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
Dermatitis atopic	235.43	24.70	61	3082	9663	63476216
Application site pain	80.93	24.70	22	3121	4160	63481719
Eczema	74.80	24.70	35	3108	32256	63453623
Pruritus	74.12	24.70	90	3053	361363	63124516
Skin exfoliation	62.42	24.70	34	3109	43068	63442811
Dry skin	61.30	24.70	37	3106	56850	63429029
Steroid withdrawal syndrome	61.22	24.70	12	3131	533	63485346
Psoriasis	58.21	24.70	42	3101	86915	63398964
Application site erythema	51.52	24.70	16	3127	4819	63481060
Erythema	39.53	24.70	46	3097	175705	63310174
Application site irritation	37.59	24.70	10	3133	1740	63484139
Application site pruritus	37.52	24.70	12	3131	3972	63481907
Skin burning sensation	36.41	24.70	16	3127	12718	63473161
Skin fissures	34.82	24.70	15	3128	11373	63474506
Rash	33.95	24.70	81	3062	560790	62925089
Dry eye	30.27	24.70	21	3122	40740	63445139
Drug ineffective	29.27	24.70	115	3028	1044650	62441229
Vulval disorder	28.67	24.70	7	3136	865	63485014
Application site dryness	26.86	24.70	5	3138	168	63485711
Product use in unapproved indication	26.31	24.70	38	3105	179042	63306837
Application site swelling	26.11	24.70	6	3137	572	63485307

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
Dermatitis atopic	179.01	28.98	42	1410	5305	34950174
Pruritus	46.80	28.98	42	1410	141939	34813540
Application site pain	38.49	28.98	10	1442	1898	34953581
Limbic encephalitis	34.62	28.98	7	1445	436	34955043
Drug ineffective	32.27	28.98	63	1389	456688	34498791

FDA Adverse Event Reporting System (Geriatric)

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
Dermatitis atopic	246.89	23.51	61	3098	9995	79731234
Application site pain	102.45	23.51	26	3133	4721	79736508
Steroid withdrawal syndrome	91.69	23.51	17	3142	704	79740525
Pruritus	71.92	23.51	83	3076	394565	79346664
Eczema	68.30	23.51	33	3126	40785	79700444
Application site erythema	67.55	23.51	19	3140	5091	79736138
Skin exfoliation	48.31	23.51	29	3130	55071	79686158
Erythema	43.99	23.51	49	3110	223241	79517988
Dry skin	42.72	23.51	29	3130	67966	79673263
Limbic encephalitis	41.08	23.51	9	3150	866	79740363
Psoriasis	39.86	23.51	31	3128	89556	79651673
Drug ineffective	39.28	23.51	112	3047	1080801	78660428
Ocular hyperaemia	38.87	23.51	20	3139	28186	79713043
Application site pruritus	36.35	23.51	11	3148	3799	79737430
Rash	34.91	23.51	73	3086	578285	79162944
Application site irritation	34.91	23.51	9	3150	1735	79739494
Skin burning sensation	32.50	23.51	14	3145	13258	79727971
Eye pruritus	32.49	23.51	16	3143	20554	79720675
Eye irritation	32.41	23.51	16	3143	20665	79720564
Application site vesicles	31.61	23.51	8	3151	1432	79739797
Application site swelling	31.25	23.51	7	3152	746	79740483
Application site dermatitis	27.40	23.51	5	3154	189	79741040
Application site dryness	26.26	23.51	5	3154	239	79740990
Dry eye	26.20	23.51	17	3142	36914	79704315
Eye swelling	25.99	23.51	15	3144	26453	79714776
Application site discolouration	25.04	23.51	6	3153	858	79740371
Dermatitis contact	24.94	23.51	11	3148	11022	79730207

FDA Adverse Event Reporting System (Pediatric)

None

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 | Suggest Off label Use Form| |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

🐶 Veterinary Drug Use

None

🐶 Veterinary products

None

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