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

Stem definition	Drug id	CAS RN
nucleosides antiviral or antineoplastic agents, cytarabine or azacitidine derivatives	25	320-67-2

Description:

Molecule	Description
Molfile Inchi Smiles Synonyms: 5-azacytidine azacitidine azacytidine ladakamycin ledakamycin vidaza U-18496	A pyrimidine analogue that inhibits DNA methyltransferase, impairing DNA methylation. It is also an antimetabolite of cytidine, incorporated primarily into RNA. Azacytidine has been used as an antineoplastic agent. Molecular weight: 244.21 Formula: C8H12N4O5 CLOGP: -2.20 LIPINSKI: 0 HAC: 9 HDO: 4 TPSA: 140.97 ALOGS: -1.30 ROTB: 2 Status: OFP Legend: OFP - off patent OFM - off market ONP - on patent

Molecule

Description

Molfile Inchi Smiles

Synonyms:

5-azacytidine
azacitidine
azacytidine
ladakamycin
ledakamycin
vidaza
U-18496

A pyrimidine analogue that inhibits DNA methyltransferase, impairing DNA methylation. It is also an antimetabolite of cytidine, incorporated primarily into RNA. Azacytidine has been used as an antineoplastic agent.

Molecular weight: 244.21
Formula: C8H12N4O5
CLOGP: -2.20
LIPINSKI: 0
HAC: 9
HDO: 4
TPSA: 140.97
ALOGS: -1.30
ROTB: 2

Status: OFP

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

Drug dosage:

None

ADMET properties:

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Property	Value	Reference
S (Water solubility)	89 mg/mL	Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine)	62 %	Benet LZ, Broccatelli F, Oprea TI
CL (Clearance)	35 mL/min/kg	Lombardo F, Berellini G, Obach RS
BDDCS (Biopharmaceutical Drug Disposition Classification System)	3	Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose)	177.10 µM/kg/day	Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
Vd (Volume of distribution)	0.47 L/kg	Lombardo F, Berellini G, Obach RS
t_half (Half-life)	0.36 hours	Lombardo F, Berellini G, Obach RS

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Approvals:

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Date	Agency	Company
Aug. 2, 2019	EMA	Celgene Europe BV
Jan. 21, 2011	PMDA	Nippon Shinyaku Co., Ltd.
May 19, 2004	FDA	CELGENE

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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
Febrile neutropenia	1634.10	22.16	732	15754	117717	63354819
Acute myeloid leukaemia	687.22	22.16	231	16255	16916	63455620
Death	475.29	22.16	532	15954	373849	63098687
Thrombocytopenia	473.52	22.16	357	16129	150800	63321736
Pancytopenia	385.75	22.16	265	16221	96668	63375868
Acute myeloid leukaemia recurrent	361.41	22.16	84	16402	1539	63470997
Neutropenia	352.34	22.16	320	16166	174685	63297851
Sepsis	352.18	22.16	302	16184	152821	63319715
Pneumonia	348.35	22.16	504	15982	456263	63016273
Myelosuppression	264.02	22.16	127	16359	23576	63448960

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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
Febrile neutropenia	1875.17	18.21	1196	24824	135653	34795258
Acute myeloid leukaemia	858.41	18.21	367	25653	17903	34913008
Pneumonia	558.18	18.21	976	25044	361651	34569260
Sepsis	457.03	18.21	589	25431	165972	34764939
Neutrophil count decreased	401.08	18.21	320	25700	50784	34880127
Death	390.98	18.21	889	25131	397160	34533751
Neutropenia	367.84	18.21	514	25506	156264	34774647
Platelet count decreased	333.39	18.21	427	25593	119290	34811621
Acute myeloid leukaemia recurrent	297.93	18.21	96	25924	2074	34928837
Pancytopenia	270.33	18.21	343	25677	94814	34836097

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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
Febrile neutropenia	3256.93	18.57	1750	35801	229249	79477588
Acute myeloid leukaemia	1094.34	18.57	445	37106	30440	79676397
Pneumonia	868.00	18.57	1289	36262	658957	79047880
Death	791.34	18.57	1139	36412	565375	79141462
Sepsis	772.85	18.57	782	36769	268646	79438191
Neutropenia	648.23	18.57	735	36816	286975	79419862
Thrombocytopenia	635.80	18.57	700	36851	264559	79442278
Acute myeloid leukaemia recurrent	621.23	18.57	169	37382	3214	79703623
Neutrophil count decreased	580.41	18.57	424	37127	93535	79613302
Pancytopenia	514.69	18.57	503	37048	165242	79541595

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FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

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Source	Code	Description
ATC	L01BC07	ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS ANTINEOPLASTIC AGENTS ANTIMETABOLITES Pyrimidine analogues
CHEBI has role	CHEBI:35610	antineoplastic agents
FDA EPC	N0000175595	Nucleoside Metabolic Inhibitor
FDA MoA	N0000000233	Nucleic Acid Synthesis Inhibitors
MeSH PA	D000963	Antimetabolites
MeSH PA	D000964	Antimetabolites, Antineoplastic
MeSH PA	D000970	Antineoplastic Agents
MeSH PA	D004791	Enzyme Inhibitors
MeSH PA	D009676	Noxae

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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
Acute myeloid leukemia, disease	indication	91861009
Myelodysplastic syndrome	indication	109995007
Chronic myelomonocytic leukemia	indication	127225006
Hepatic failure	contraindication	59927004
Kidney disease	contraindication	90708001	DOID:557
Pregnancy, function	contraindication	289908002
Thrombocytopenic disorder	contraindication	302215000	DOID:1588
Neutropenic disorder	contraindication	303011007	DOID:1227
Breastfeeding (mother)	contraindication	413712001
Advanced Malignant Neoplasm of Liver	contraindication

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🐶 Veterinary Drug Use

None

🐶 Veterinary products

None

Acid dissociation constants calculated using MoKa v3.0.0

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Dissociation level	Dissociation constant	Type (acidic/basic)
pKa1	12.32	acidic
pKa2	12.92	acidic
pKa3	13.79	acidic
pKa4	4.43	Basic
pKa5	2.98	Basic

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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
200MG	ONUREG	BRISTOL	N214120	Sept. 1, 2020	RX	TABLET	ORAL	8846628	June 3, 2030	CONTINUED TREATMENT OF ADULTS WITH ACUTE MYELOID LEUKEMIA WHO ACHIEVED FIRST COMPLETE REMISSION (CR) OR CR WITH INCOMPLETE BLOOD COUNT RECOVERY FOLLOWING INTENSIVE INDUCTION CHEMOTHERAPY AND ARE NOT ABLE TO COMPLETE INTENSIVE CURATIVE THERAPY
300MG	ONUREG	BRISTOL	N214120	Sept. 1, 2020	RX	TABLET	ORAL	8846628	June 3, 2030	CONTINUED TREATMENT OF ADULTS WITH ACUTE MYELOID LEUKEMIA WHO ACHIEVED FIRST COMPLETE REMISSION (CR) OR CR WITH INCOMPLETE BLOOD COUNT RECOVERY FOLLOWING INTENSIVE INDUCTION CHEMOTHERAPY AND ARE NOT ABLE TO COMPLETE INTENSIVE CURATIVE THERAPY

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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
100MG/VIAL	VIDAZA	BRISTOL-MYERS	N050794	May 19, 2004	RX	POWDER	INTRAVENOUS, SUBCUTANEOUS	May 20, 2025	TREATMENT OF PEDIATRIC PATIENTS AGED ONE MONTH AND OLDER WITH NEWLY DIAGNOSED JUVENILE MYELOMONOCYTIC LEUKEMIA (JMML)
100MG/VIAL	VIDAZA	BRISTOL-MYERS	N050794	May 19, 2004	RX	POWDER	INTRAVENOUS, SUBCUTANEOUS	May 20, 2029	TREATMENT OF PEDIATRIC PATIENTS AGED ONE MONTH AND OLDER WITH NEWLY DIAGNOSED JUVENILE MYELOMONOCYTIC LEUKEMIA (JMML)
200MG	ONUREG	BRISTOL	N214120	Sept. 1, 2020	RX	TABLET	ORAL	Sept. 1, 2023	NEW PRODUCT
200MG	ONUREG	BRISTOL	N214120	Sept. 1, 2020	RX	TABLET	ORAL	Sept. 1, 2027	INDICATED FOR CONTINUED TREATMENT OF ADULT PATIENTS WITH ACUTE MYELOID LEUKEMIA WHO ACHIEVED FIRST COMPLETE REMISSION (CR) OR COMPLETE REMISSION WITH INCOMPLETE BLOOD COUNT RECOVERY (CRI) FOLLOWING INTENSIVE INDUCTION CHEMOTHERAPY AND ARE NOT ABLE TO COMPLETE INTENSIVE CURATIVE THERAPY
300MG	ONUREG	BRISTOL	N214120	Sept. 1, 2020	RX	TABLET	ORAL	Sept. 1, 2023	NEW PRODUCT
300MG	ONUREG	BRISTOL	N214120	Sept. 1, 2020	RX	TABLET	ORAL	Sept. 1, 2027	INDICATED FOR CONTINUED TREATMENT OF ADULT PATIENTS WITH ACUTE MYELOID LEUKEMIA WHO ACHIEVED FIRST COMPLETE REMISSION (CR) OR COMPLETE REMISSION WITH INCOMPLETE BLOOD COUNT RECOVERY (CRI) FOLLOWING INTENSIVE INDUCTION CHEMOTHERAPY AND ARE NOT ABLE TO COMPLETE INTENSIVE CURATIVE THERAPY

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Bioactivity Summary:

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Target	Class	Pharos	UniProt	Action	Type	Activity value (-log[M])	Mechanism action	Bioact source	MoA source
DNA (cytosine-5)-methyltransferase 1	Enzyme	P26358	DNMT1_HUMAN	INHIBITOR	IC50	6.52		CHEMBL	CHEMBL
DNA (cytosine-5)-methyltransferase 3A	Enzyme	Q9Y6K1	DNM3A_HUMAN	INHIBITOR				CHEMBL	CHEMBL

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External reference:

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ID	Source
5AE	PDB_CHEM_ID
008661	NDDF
1251	RXNORM
18639	MMSL
205981	MMSL
4021468	VUID
4021468	VANDF
412328000	SNOMEDCT_US
412329008	SNOMEDCT_US
4520	INN_ID

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Pharmaceutical products:

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Product	Category	Ingredients	NDC	Form	Quantity	Route	Marketing	Label
Azacitidine	HUMAN PRESCRIPTION DRUG LABEL	1	0143-9606	INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION	100 mg	INTRAVENOUS	ANDA	24 sections
Azacitidine	HUMAN PRESCRIPTION DRUG LABEL	1	0143-9606	INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION	100 mg	INTRAVENOUS	ANDA	24 sections
Azacitidine	HUMAN PRESCRIPTION DRUG LABEL	1	0781-3253	INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION	100 mg	SUBCUTANEOUS	NDA AUTHORIZED GENERIC	28 sections
Azacitidine	HUMAN PRESCRIPTION DRUG LABEL	1	0781-3253	INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION	100 mg	SUBCUTANEOUS	NDA AUTHORIZED GENERIC	28 sections
Azacitidine	HUMAN PRESCRIPTION DRUG LABEL	1	0781-3253	INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION	100 mg	SUBCUTANEOUS	NDA AUTHORIZED GENERIC	28 sections
Azacitidine	HUMAN PRESCRIPTION DRUG LABEL	1	0781-9253	INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION	100 mg	SUBCUTANEOUS	NDA AUTHORIZED GENERIC	28 sections
Azacitidine	HUMAN PRESCRIPTION DRUG LABEL	1	0781-9253	INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION	100 mg	SUBCUTANEOUS	NDA AUTHORIZED GENERIC	28 sections
Azacitidine	HUMAN PRESCRIPTION DRUG LABEL	1	0781-9253	INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION	100 mg	SUBCUTANEOUS	NDA AUTHORIZED GENERIC	28 sections
Azacitidine	HUMAN PRESCRIPTION DRUG LABEL	1	16714-578	INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION	100 mg	INTRAVENOUS	ANDA	25 sections
Azacitidine	HUMAN PRESCRIPTION DRUG LABEL	1	16714-578	INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION	100 mg	INTRAVENOUS	ANDA	25 sections

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