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sirolimus 🐶 Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definition	Drug id	CAS RN
immunosuppressants, rapamycin derivatives	2446	53123-88-9

Description:

Molecule	Description
Molfile Inchi Smiles Synonyms: sirolimus rapamycin rapammune rapamune supralimus rapalimus AY22989 AY-22989	A macrolide compound obtained from Streptomyces hygroscopicus that acts by selectively blocking the transcriptional activation of cytokines thereby inhibiting cytokine production. It is bioactive only when bound to IMMUNOPHILINS. Sirolimus is a potent immunosuppressant and possesses both antifungal and antineoplastic properties. Limited data describing efficacy in patients with COVID-19 is available. However, its efficacy and safety in the treatment of COVID-19 was not established. Molecular weight: 914.19 Formula: C51H79NO13 CLOGP: 7.04 LIPINSKI: 3 HAC: 14 HDO: 3 TPSA: 195.43 ALOGS: -5.72 ROTB: 6 Status: OFP Legend: OFP - off patent OFM - off market ONP - on patent

Molecule

Description

Molfile Inchi Smiles

Synonyms:

sirolimus
rapamycin
rapammune
rapamune
supralimus
rapalimus
AY22989
AY-22989

A macrolide compound obtained from Streptomyces hygroscopicus that acts by selectively blocking the transcriptional activation of cytokines thereby inhibiting cytokine production. It is bioactive only when bound to IMMUNOPHILINS. Sirolimus is a potent immunosuppressant and possesses both antifungal and antineoplastic properties. Limited data describing efficacy in patients with COVID-19 is available. However, its efficacy and safety in the treatment of COVID-19 was not established.

Molecular weight: 914.19
Formula: C51H79NO13
CLOGP: 7.04
LIPINSKI: 3
HAC: 14
HDO: 3
TPSA: 195.43
ALOGS: -5.72
ROTB: 6

Status: OFP

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

Drug dosage:

Dose	Unit	Route
3	mg	O

ADMET properties:

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Property	Value	Reference
EoM (Fraction excreted unchanged in urine)	2 %	Benet LZ, Broccatelli F, Oprea TI
BDDCS (Biopharmaceutical Drug Disposition Classification System)	2	Benet LZ, Broccatelli F, Oprea TI
BA (Bioavailability)	15 %	Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
MRTD (Maximum Recommended Therapeutic Daily Dose)	0.15 µM/kg/day	Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
S (Water solubility)	0.00 mg/mL	Bocci G, Oprea TI, Benet LZ

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Approvals:

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Date	Agency	Company
July 4, 2014	PMDA	NOBELPHARMA CO., LTD
March 13, 2001	EMA	Pfizer Europe MA EEIG
Sept. 15, 1999	FDA	PF PRISM CV

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FDA Adverse Event Reporting System (Female)

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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
Transplant dysfunction	2119.59	18.08	445	18051	4427	63466099
Transplant rejection	2050.09	18.08	501	17995	10279	63460247
Ovarian cyst	1445.06	18.08	412	18084	15533	63454993
Acne	1295.14	18.08	413	18083	22880	63447646
Alopecia	345.40	18.08	456	18040	337080	63133446
Epstein-Barr virus infection	266.66	18.08	97	18399	7953	63462573
Sleep disorder due to general medical condition, insomnia type	246.55	18.08	166	18330	52051	63418475
Liver function test abnormal	236.68	18.08	157	18339	48024	63422502
Product use in unapproved indication	222.37	18.08	267	18229	178813	63291713
Post transplant lymphoproliferative disorder	209.99	18.08	72	18424	4959	63465567

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FDA Adverse Event Reporting System (Male)

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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
Transplant rejection	464.54	14.32	187	19979	10124	34926641
Off label use	350.33	14.32	753	19413	418771	34517994
Product use in unapproved indication	348.77	14.32	382	19784	117117	34819648
Kidney transplant rejection	310.32	14.32	128	20038	7369	34929396
Cytomegalovirus infection	167.64	14.32	131	20035	26004	34910761
Adenovirus infection	159.19	14.32	72	20094	5185	34931580
Immunosuppressant drug level increased	152.51	14.32	73	20093	5982	34930783
Post transplant lymphoproliferative disorder	150.27	14.32	74	20092	6454	34930311
Liver transplant rejection	140.57	14.32	51	20115	2068	34934697
Thrombotic microangiopathy	139.52	14.32	83	20083	10547	34926218

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FDA Adverse Event Reporting System (Geriatric)

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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
Transplant rejection	2160.01	14.69	641	33384	18796	79691567
Transplant dysfunction	1899.21	14.69	470	33555	6751	79703612
Ovarian cyst	1338.39	14.69	402	33623	12253	79698110
Acne	1141.26	14.69	431	33594	26759	79683604
Product use in unapproved indication	577.48	14.69	618	33407	249741	79460622
Off label use	527.21	14.69	1176	32849	906039	78804324
Alopecia	357.92	14.69	466	33559	230889	79479474
Kidney transplant rejection	353.43	14.69	141	33884	10105	79700258
Epstein-Barr virus infection	335.56	14.69	150	33875	14266	79696097
Post transplant lymphoproliferative disorder	324.70	14.69	137	33888	11327	79699036

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FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

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Source	Code	Description
ATC	L01EG04	ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS ANTINEOPLASTIC AGENTS PROTEIN KINASE INHIBITORS Mammalian target of rapamycin (mTOR) kinase inhibitors
ATC	L04AA10	ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS IMMUNOSUPPRESSANTS IMMUNOSUPPRESSANTS Selective immunosuppressants
ATC	S01XA23	SENSORY ORGANS OPHTHALMOLOGICALS OTHER OPHTHALMOLOGICALS Other ophthalmologicals
CHEBI has role	CHEBI:35610	antineoplastic agents
CHEBI has role	CHEBI:35705	immunosuppressive agents
CHEBI has role	CHEBI:36047	antibacterial drugs
CHEBI has role	CHEBI:68481	mTOR inhibitors
CHEBI has role	CHEBI:149553	anticoronaviral drug
CHEBI has role	CHEBI:176497	geroprotectors
FDA EPC	N0000175605	Kinase Inhibitor

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Drug Use | Suggest Off label Use Form| |View source of the data|

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Disease	Relation	SNOMED_ID	DOID
Gorham's disease	indication	1515008
Tuberous sclerosis syndrome	indication	7199000	DOID:13515
Lymphangiectasis	indication	48087001
Pulmonary lymphangioleiomyomatosis	indication	277844007	DOID:3319
Lymphangioma	indication	400178008	DOID:1475
Lymphangiomatosis	indication	403546006
Renal cell carcinoma	indication	702391001	DOID:4450
Prevention of Kidney Transplant Rejection	indication
Coronavirus infection	off-label use	186747009
Prevention of Cardiac Transplant Rejection	off-label use

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🐶 Veterinary Drug Use

None

🐶 Veterinary products

None

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation level	Dissociation constant	Type (acidic/basic)
pKa1	10.5	acidic

Orange Book patent data (new drug applications)

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Formulation strength	Trade name	Applicant	Application number	Approval date	Type	Dose form	Route	Patent number	Patent expiration date	Patent use
100MG/VIAL	FYARRO	AADI	N213312	Nov. 22, 2021	RX	POWDER	INTRAVENOUS	8911786	Feb. 14, 2029	TREATMENT OF ADULT PATIENTS WITH LOCALLY ADVANCED UNRESECTABLE OR METASTATIC MALIGNANT PERIVASCULAR EPITHELIOID CELL TUMOR (PECOMA)
100MG/VIAL	FYARRO	AADI	N213312	Nov. 22, 2021	RX	POWDER	INTRAVENOUS	10973806	June 29, 2036	TREATMENT OF ADULT PATIENTS WITH LOCALLY ADVANCED UNRESECTABLE OR METASTATIC MALIGNANT PERIVASCULAR EPITHELIOID CELL TUMOR (PECOMA) WITH A DOSE BETWEEN ABOUT 56 MG/M2 AND ABOUT 100 MG/M2 ADMINISTERED ON DAYS 1 AND 8 OF A 21-DAY CYCLE

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Orange Book exclusivity data (new drug applications)

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Formulation strength	Trade name	Applicant	Application number	Approval date	Type	Dose form	Route	Exclusivity date	Description
0.2%	HYFTOR	NOBELPHARMA	N213478	March 22, 2022	RX	GEL	TOPICAL	March 22, 2025	NEW PRODUCT
0.2%	HYFTOR	NOBELPHARMA	N213478	March 22, 2022	RX	GEL	TOPICAL	March 22, 2029	TREATMENT OF FACIAL ANGIOFIBROMA ASSOCIATED WITH TUBEROUS SCLEROSIS IN ADULTS AND PEDIATRIC PATIENTS 6 YEARS OF AGE AND OLDER
100MG/VIAL	FYARRO	AADI	N213312	Nov. 22, 2021	RX	POWDER	INTRAVENOUS	Nov. 22, 2024	NEW PRODUCT
100MG/VIAL	FYARRO	AADI	N213312	Nov. 22, 2021	RX	POWDER	INTRAVENOUS	Nov. 22, 2028	FOR THE TREATMENT OF ADULT PATIENTS WITH LOCALLY ADVANCED UNRESECTABLE OR METASTATIC MALIGNANT PERIVASCULAR EPITHELIOID CELL TUMOR (PECOMA)

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Bioactivity Summary:

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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	8.96	WOMBAT-PK	CHEMBL
Cytochrome P450 3A4	Enzyme	P08684	CP3A4_HUMAN		IC50	5.70	DRUG MATRIX
Multidrug resistance protein 1	Transporter	P08183	MDR1_HUMAN		IC50	6.20	WOMBAT-PK
ATP-binding cassette sub-family G member 2	Transporter	Q9UNQ0	ABCG2_HUMAN		IC50	5.72	CHEMBL
Cytochrome P450 2C9	Enzyme	P11712	CP2C9_HUMAN		IC50	5.70	DRUG MATRIX
Serine/threonine-protein kinase mTOR	Kinase	P42345	MTOR_HUMAN		IC50	10	CHEMBL
Peptidyl-prolyl cis-trans isomerase FKBP3	Enzyme	Q00688	FKBP3_HUMAN		Kd	9.70	WOMBAT-PK
Cytochrome P450 2C19	Enzyme	P33261	CP2CJ_HUMAN		IC50	5.40	DRUG MATRIX
Peptidyl-prolyl cis-trans isomerase FKBP1B	Enzyme	P68106	FKB1B_HUMAN		Kd	9.70	CHEMBL
Peptidyl-prolyl cis-trans isomerase FKBP5	Enzyme	Q13451	FKBP5_HUMAN		Ki	8.52	CHEMBL

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External reference:

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ID	Source
007885	NDDF
116109004	SNOMEDCT_US
210889	MMSL
258355	RXNORM
31418	MMSL
387014003	SNOMEDCT_US
4021176	VUID
4021176	VANDF
5284616	PUBCHEM_CID
6031	IUPHAR_LIGAND_ID

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Pharmaceutical products:

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Product	Category	Ingredients	NDC	Form	Quantity	Route	Marketing	Label
Rapamune	HUMAN PRESCRIPTION DRUG LABEL	1	0008-1030	SOLUTION	1 mg	ORAL	NDA	34 sections
Rapamune	HUMAN PRESCRIPTION DRUG LABEL	1	0008-1030	SOLUTION	1 mg	ORAL	NDA	34 sections
Rapamune	HUMAN PRESCRIPTION DRUG LABEL	1	0008-1030	SOLUTION	1 mg	ORAL	NDA	34 sections
Rapamune	HUMAN PRESCRIPTION DRUG LABEL	1	0008-1040	TABLET, SUGAR COATED	0.50 mg	ORAL	NDA	34 sections
Rapamune	HUMAN PRESCRIPTION DRUG LABEL	1	0008-1040	TABLET, SUGAR COATED	0.50 mg	ORAL	NDA	34 sections
Rapamune	HUMAN PRESCRIPTION DRUG LABEL	1	0008-1040	TABLET, SUGAR COATED	0.50 mg	ORAL	NDA	34 sections
Rapamune	HUMAN PRESCRIPTION DRUG LABEL	1	0008-1041	TABLET, SUGAR COATED	1 mg	ORAL	NDA	34 sections
Rapamune	HUMAN PRESCRIPTION DRUG LABEL	1	0008-1041	TABLET, SUGAR COATED	1 mg	ORAL	NDA	34 sections
Rapamune	HUMAN PRESCRIPTION DRUG LABEL	1	0008-1041	TABLET, SUGAR COATED	1 mg	ORAL	NDA	34 sections
Rapamune	HUMAN PRESCRIPTION DRUG LABEL	1	0008-1042	TABLET, SUGAR COATED	2 mg	ORAL	NDA	34 sections

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