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

Stem definition	Drug id	CAS RN
immunosuppressants, rapamycin derivatives	2552	104987-11-3

Description:

Molecule	Description
Molfile Inchi Smiles Synonyms: FK-506 tacrolimus hydrate tacrolimus fujimycin tsukubaenolide anhydrous tacrolimus tacrolimus anhydrous modigraf FR900506	A macrolide isolated from the culture broth of a strain of Streptomyces tsukubaensis that has strong immunosuppressive activity in vivo and prevents the activation of T-lymphocytes in response to antigenic or mitogenic stimulation in vitro. Molecular weight: 804.03 Formula: C44H69NO12 CLOGP: 5.78 LIPINSKI: 3 HAC: 13 HDO: 3 TPSA: 178.36 ALOGS: -5.30 ROTB: 7 Status: OFP Legend: OFP - off patent OFM - off market ONP - on patent

Molecule

Description

Molfile Inchi Smiles

Synonyms:

FK-506
tacrolimus hydrate
tacrolimus
fujimycin
tsukubaenolide
anhydrous tacrolimus
tacrolimus anhydrous
modigraf
FR900506

A macrolide isolated from the culture broth of a strain of Streptomyces tsukubaensis that has strong immunosuppressive activity in vivo and prevents the activation of T-lymphocytes in response to antigenic or mitogenic stimulation in vitro.

Molecular weight: 804.03
Formula: C44H69NO12
CLOGP: 5.78
LIPINSKI: 3
HAC: 13
HDO: 3
TPSA: 178.36
ALOGS: -5.30
ROTB: 7

Status: OFP

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

Drug dosage:

Dose	Unit	Route
5	mg	O
5	mg	P

ADMET properties:

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Property	Value	Reference
t_half (Half-life)	26 hours	Lombardo F, Berellini G, Obach RS
BA (Bioavailability)	25 %	Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
BDDCS (Biopharmaceutical Drug Disposition Classification System)	2	Benet LZ, Broccatelli F, Oprea TI
Vd (Volume of distribution)	1.20 L/kg	Lombardo F, Berellini G, Obach RS
CL (Clearance)	0.70 mL/min/kg	Lombardo F, Berellini G, Obach RS
EoM (Fraction excreted unchanged in urine)	0.50 %	Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose)	0.24 µM/kg/day	Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
S (Water solubility)	0.01 mg/mL	Benet LZ, Broccatelli F, Oprea TI
fu (Fraction unbound in plasma)	0.01 %	Lombardo F, Berellini G, Obach RS

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Approvals:

Date	Agency	Company	Orphan
April 8, 1994	FDA	ASTELLAS
Feb. 27, 2002	EMA	LEO PHARMA A/S

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 rejection	4232.28	11.04	1362	133492	9418	63344750
Cytomegalovirus infection	2816.11	11.04	1204	133650	19748	63334420
Post transplant lymphoproliferative disorder	2600.85	11.04	785	134069	4246	63349922
Thrombotic microangiopathy	2109.06	11.04	807	134047	9754	63344414
Immunosuppressant drug level increased	1589.38	11.04	499	134355	3139	63351029
Kidney transplant rejection	1434.83	11.04	480	134374	3791	63350377
Transplant dysfunction	1326.97	11.04	468	134386	4404	63349764
Epstein-Barr virus infection	1273.75	11.04	520	134334	7530	63346638
Cytomegalovirus viraemia	1125.19	11.04	431	134423	5218	63348950
Polyomavirus-associated nephropathy	1119.06	11.04	326	134528	1522	63352646

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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	3091.86	11.09	1335	169901	8976	34776719
Cytomegalovirus infection	2236.62	11.09	1464	169772	24671	34761024
Post transplant lymphoproliferative disorder	1874.10	11.09	820	170416	5708	34779987
Immunosuppressant drug level increased	1739.54	11.09	761	170475	5294	34780401
Polyomavirus-associated nephropathy	1693.29	11.09	656	170580	3188	34782507
Kidney transplant rejection	1395.47	11.09	698	170538	6799	34778896
Thrombotic microangiopathy	1298.76	11.09	748	170488	9882	34775813
Complications of transplanted kidney	1156.51	11.09	527	170709	4082	34781613
Nocardiosis	1001.53	11.09	455	170781	3496	34782199
BK virus infection	968.04	11.09	500	170736	5238	34780457

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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	6652.02	10.46	2512	274361	16925	79450590
Cytomegalovirus infection	4684.50	10.46	2486	274387	40158	79427357
Post transplant lymphoproliferative disorder	4469.30	10.46	1631	275242	9833	79457682
Thrombotic microangiopathy	3170.24	10.46	1500	275373	18669	79448846
Immunosuppressant drug level increased	3167.87	10.46	1189	275684	7838	79459677
Polyomavirus-associated nephropathy	2839.01	10.46	970	275903	4657	79462858
Kidney transplant rejection	2457.19	10.46	1025	275848	9221	79458294
Product use in unapproved indication	2307.62	10.46	3536	273337	246823	79220692
Transplant dysfunction	2020.76	10.46	807	276066	6414	79461101
Complications of transplanted kidney	1944.60	10.46	758	276115	5608	79461907

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FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

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Source	Code	Description
ATC	D11AH01	DERMATOLOGICALS OTHER DERMATOLOGICAL PREPARATIONS OTHER DERMATOLOGICAL PREPARATIONS Agents for dermatitis, excluding corticosteroids
ATC	L04AD02	ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS IMMUNOSUPPRESSANTS IMMUNOSUPPRESSANTS Calcineurin inhibitors
CHEBI has role	CHEBI:35705	immunosuppressive agents
FDA EPC	N0000175457	Calcineurin Inhibitor Immunosuppressant
FDA MoA	N0000175458	Calcineurin Inhibitors
MeSH PA	D065095	Calcineurin Inhibitors
MeSH PA	D004791	Enzyme Inhibitors
MeSH PA	D007155	Immunologic Factors
MeSH PA	D007166	Immunosuppressive Agents

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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
Atopic dermatitis	indication	24079001	DOID:3310
Transplanted organ rejection	indication	213148006
Liver transplant rejection	indication	235911006
Renal transplant rejection	indication	236570004
Prevention of Cardiac Transplant Rejection	indication
Prevention of Transplant Rejection	indication
Prevention of Liver Transplant Rejection	indication
Intractable Eczema	indication
Prevention of Kidney Transplant Rejection	indication
Prevention of Lung 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	12.4	acidic
pKa2	13.12	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
EQ 0.75MG BASE	ENVARSUS XR	VELOXIS PHARMS INC	N206406	July 10, 2015	RX	TABLET, EXTENDED RELEASE	ORAL	10548880	Aug. 30, 2024	PROPHYLAXIS OF ORGAN REJECTION IN DE NOVO TRANSPLANT PATIENT
EQ 0.75MG BASE	ENVARSUS XR	VELOXIS PHARMS INC	N206406	July 10, 2015	RX	TABLET, EXTENDED RELEASE	ORAL	10548880	Aug. 30, 2024	PROPHYLAXIS OF ORGAN REJECTION IN PATIENTS CONVERTED FROM TACROLIMUS IMMEDIATE-RELEASE FORMULATIONS
EQ 0.75MG BASE	ENVARSUS XR	VELOXIS PHARMS INC	N206406	July 10, 2015	RX	TABLET, EXTENDED RELEASE	ORAL	8486993	Aug. 30, 2024	PROPHYLAXIS OF ORGAN REJECTION
EQ 0.75MG BASE	ENVARSUS XR	VELOXIS PHARMS INC	N206406	July 10, 2015	RX	TABLET, EXTENDED RELEASE	ORAL	8586084	Aug. 30, 2024	PROPHYLAXIS OF ORGAN REJECTION
EQ 0.75MG BASE	ENVARSUS XR	VELOXIS PHARMS INC	N206406	July 10, 2015	RX	TABLET, EXTENDED RELEASE	ORAL	8623411	Aug. 30, 2024	PROPHYLAXIS OF ORGAN REJECTION
EQ 0.75MG BASE	ENVARSUS XR	VELOXIS PHARMS INC	N206406	July 10, 2015	RX	TABLET, EXTENDED RELEASE	ORAL	8889185	Aug. 30, 2024	PROPHYLAXIS OF ORGAN REJECTION
EQ 0.75MG BASE	ENVARSUS XR	VELOXIS PHARMS INC	N206406	July 10, 2015	RX	TABLET, EXTENDED RELEASE	ORAL	8889186	Aug. 30, 2024	PROPHYLAXIS OF ORGAN REJECTION
EQ 0.75MG BASE	ENVARSUS XR	VELOXIS PHARMS INC	N206406	July 10, 2015	RX	TABLET, EXTENDED RELEASE	ORAL	9161907	Aug. 30, 2024	PROPHYLAXIS OF ORGAN REJECTION
EQ 0.75MG BASE	ENVARSUS XR	VELOXIS PHARMS INC	N206406	July 10, 2015	RX	TABLET, EXTENDED RELEASE	ORAL	10864199	May 30, 2028	PROPHYLAXIS OF ORGAN REJECTION IN DE NOVO TRANSPLANT PATIENT
EQ 0.75MG BASE	ENVARSUS XR	VELOXIS PHARMS INC	N206406	July 10, 2015	RX	TABLET, EXTENDED RELEASE	ORAL	10864199	May 30, 2028	PROPHYLAXIS OF ORGAN REJECTION IN PATIENTS CONVERTED FROM TACROLIMUS IMMEDIATE-RELEASE FORMULATIONS

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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
EQ 0.2MG BASE/PACKET	PROGRAF	ASTELLAS	N210115	May 24, 2018	RX	FOR SUSPENSION	ORAL	May 24, 2025	PROPHYLAXIS OF ORGAN REJECTION IN PEDIATRIC PATIENTS RECEIVING ALLOGENEIC KIDNEY TRANSPLANT, LIVER TRANSPLANTS, AND HEART TRANSPLANT, IN COMBINATION WITH OTHER IMMUNOSUPPRESSANTS
EQ 0.2MG BASE/PACKET	PROGRAF	ASTELLAS	N210115	May 24, 2018	RX	FOR SUSPENSION	ORAL	July 16, 2028	FOR PROPHYLAXIS OF ORGAN REJECTION IN ADULT AND PEDIATRIC PATIENTS RECEIVING ALLOGENEIC LUNG TRANSPLANT
EQ 0.5MG BASE	PROGRAF	ASTELLAS	N050708	Aug. 24, 1998	RX	CAPSULE	ORAL	May 24, 2025	PROPHYLAXIS OF ORGAN REJECTION IN PEDIATRIC PATIENTS RECEIVING ALLOGENEIC KIDNEY OR HEART TRANSPLANTS, IN COMBINATION WITH OTHER IMMUNOSUPPRESSANTS
EQ 0.5MG BASE	ASTAGRAF XL	ASTELLAS	N204096	July 19, 2013	RX	CAPSULE, EXTENDED RELEASE	ORAL	May 24, 2025	FDA HAS NOT RECOGNIZED ORPHAN-DRUG EXCLUSIVITY (ODE) FOR THIS DRUG, BUT IT CONTAINS THE SAME ACTIVE MOIETY OR MOIETIES AS ANOTHER DRUG(S) THAT WAS ELIGIBLE FOR ODE, AND ALSO SHARES ODE-PROTECTED USE(S) OR INDICATION(S) WITH THAT DRUG(S). AN APPLICATION SEEKING APPROVAL FOR THE SAME ACTIVE MOIETY OR MOIETIES, INCLUDING AN ANDA THAT CITES THIS NDA AS ITS BASIS OF SUBMISSION, MAY NOT BE APPROVED FOR SUCH ODE-PROTECTED USE(S) AND INDICATION(S)
EQ 0.5MG BASE	PROGRAF	ASTELLAS	N050708	Aug. 24, 1998	RX	CAPSULE	ORAL	July 16, 2028	FOR PROPHYLAXIS OF ORGAN REJECTION IN ADULT AND PEDIATRIC PATIENTS RECEIVING ALLOGENEIC LUNG TRANSPLANT
EQ 1MG BASE	PROGRAF	ASTELLAS	N050708	April 8, 1994	RX	CAPSULE	ORAL	May 24, 2025	PROPHYLAXIS OF ORGAN REJECTION IN PEDIATRIC PATIENTS RECEIVING ALLOGENEIC KIDNEY OR HEART TRANSPLANTS, IN COMBINATION WITH OTHER IMMUNOSUPPRESSANTS
EQ 1MG BASE	ASTAGRAF XL	ASTELLAS	N204096	July 19, 2013	RX	CAPSULE, EXTENDED RELEASE	ORAL	May 24, 2025	FDA HAS NOT RECOGNIZED ORPHAN-DRUG EXCLUSIVITY (ODE) FOR THIS DRUG, BUT IT CONTAINS THE SAME ACTIVE MOIETY OR MOIETIES AS ANOTHER DRUG(S) THAT WAS ELIGIBLE FOR ODE, AND ALSO SHARES ODE-PROTECTED USE(S) OR INDICATION(S) WITH THAT DRUG(S). AN APPLICATION SEEKING APPROVAL FOR THE SAME ACTIVE MOIETY OR MOIETIES, INCLUDING AN ANDA THAT CITES THIS NDA AS ITS BASIS OF SUBMISSION, MAY NOT BE APPROVED FOR SUCH ODE-PROTECTED USE(S) AND INDICATION(S)
EQ 1MG BASE	PROGRAF	ASTELLAS	N050708	April 8, 1994	RX	CAPSULE	ORAL	July 16, 2028	FOR PROPHYLAXIS OF ORGAN REJECTION IN ADULT AND PEDIATRIC PATIENTS RECEIVING ALLOGENEIC LUNG TRANSPLANT
EQ 1MG BASE/PACKET	PROGRAF	ASTELLAS	N210115	May 24, 2018	RX	FOR SUSPENSION	ORAL	May 24, 2025	PROPHYLAXIS OF ORGAN REJECTION IN PEDIATRIC PATIENTS RECEIVING ALLOGENEIC KIDNEY TRANSPLANT, LIVER TRANSPLANTS, AND HEART TRANSPLANT, IN COMBINATION WITH OTHER IMMUNOSUPPRESSANTS
EQ 1MG BASE/PACKET	PROGRAF	ASTELLAS	N210115	May 24, 2018	RX	FOR SUSPENSION	ORAL	July 16, 2028	FOR PROPHYLAXIS OF ORGAN REJECTION IN ADULT AND PEDIATRIC PATIENTS RECEIVING ALLOGENEIC LUNG TRANSPLANT

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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	9.40	WOMBAT-PK	CHEMBL
Potassium voltage-gated channel subfamily H member 2	Ion channel	Q12809	KCNH2_HUMAN		IC50	6	WOMBAT-PK
Cytochrome P450 3A4	Enzyme	P08684	CP3A4_HUMAN		IC50	6	DRUG MATRIX
Interleukin-5	Cytokine	P05113	IL5_HUMAN		IC50	10.22	WOMBAT-PK
Interferon gamma	Cytokine	P01579	IFNG_HUMAN		IC50	10.22	WOMBAT-PK
ATP-binding cassette sub-family G member 2	Transporter	Q9UNQ0	ABCG2_HUMAN		IC50	5.48	CHEMBL
Serine/threonine-protein phosphatase 2B catalytic subunit gamma isoform	Enzyme	P48454	PP2BC_HUMAN		Ki	7.46	WOMBAT-PK
Serine/threonine-protein kinase mTOR	Kinase	P42345	MTOR_HUMAN		IC50	9.02	CHEMBL
Serine/threonine-protein phosphatase 2B catalytic subunit alpha isoform	Enzyme	Q08209	PP2BA_HUMAN		Kd	7.70	CHEMBL
Peptidyl-prolyl cis-trans isomerase FKBP1B	Enzyme	P68106	FKB1B_HUMAN		Kd	9.40	CHEMBL

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External reference:

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ID	Source
004446	NDDF
004447	NDDF
109129008	SNOMEDCT_US
109581-93-3	SECONDARY_CAS_RN
1269093001	SNOMEDCT_US
133309	MMSL
235991	RXNORM
386975001	SNOMEDCT_US
4020868	VUID
4020868	VANDF

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Pharmaceutical products:

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Product	Category	Ingredients	NDC	Form	Quantity	Route	Marketing	Label
ASTAGRAF XL	HUMAN PRESCRIPTION DRUG LABEL	1	0469-0647	CAPSULE, COATED, EXTENDED RELEASE	0.50 mg	ORAL	NDA	27 sections
ASTAGRAF XL	HUMAN PRESCRIPTION DRUG LABEL	1	0469-0647	CAPSULE, COATED, EXTENDED RELEASE	0.50 mg	ORAL	NDA	27 sections
ASTAGRAF XL	HUMAN PRESCRIPTION DRUG LABEL	1	0469-0647	CAPSULE, COATED, EXTENDED RELEASE	0.50 mg	ORAL	NDA	27 sections
ASTAGRAF XL	HUMAN PRESCRIPTION DRUG LABEL	1	0469-0677	CAPSULE, COATED, EXTENDED RELEASE	1 mg	ORAL	NDA	27 sections
ASTAGRAF XL	HUMAN PRESCRIPTION DRUG LABEL	1	0469-0677	CAPSULE, COATED, EXTENDED RELEASE	1 mg	ORAL	NDA	27 sections
ASTAGRAF XL	HUMAN PRESCRIPTION DRUG LABEL	1	0469-0677	CAPSULE, COATED, EXTENDED RELEASE	1 mg	ORAL	NDA	27 sections
ASTAGRAF XL	HUMAN PRESCRIPTION DRUG LABEL	1	0469-0687	CAPSULE, COATED, EXTENDED RELEASE	5 mg	ORAL	NDA	27 sections
ASTAGRAF XL	HUMAN PRESCRIPTION DRUG LABEL	1	0469-0687	CAPSULE, COATED, EXTENDED RELEASE	5 mg	ORAL	NDA	27 sections
Prograf	HUMAN PRESCRIPTION DRUG LABEL	1	0469-0607	CAPSULE, GELATIN COATED	0.50 mg	ORAL	NDA	30 sections
Prograf	HUMAN PRESCRIPTION DRUG LABEL	1	0469-0607	CAPSULE, GELATIN COATED	0.50 mg	ORAL	NDA	30 sections

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