decitabine 🐶 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	790	2353-33-5

Description:

Molecule	Description
Molfile Inchi Smiles Synonyms: decitabine mesylate decitabine mesilate decitabine dacogen	An azacitidine derivative and antineoplastic antimetabolite. It inhibits DNA methyltransferase to re-activate silent genes, limiting METASTASIS and NEOPLASM DRUG RESISTANCE. Decitabine is used in the treatment of MYELODISPLASTIC SYNDROMES, and ACUTE MYELOID LEUKEMIA. Molecular weight: 228.21 Formula: C8H12N4O4 CLOGP: -1.90 LIPINSKI: 0 HAC: 8 HDO: 3 TPSA: 120.74 ALOGS: -1.62 ROTB: 2 Status: OFP Legend: OFP - off patent OFM - off market ONP - on patent

Molecule

Description

Molfile Inchi Smiles

Synonyms:

decitabine mesylate
decitabine mesilate
decitabine
dacogen

An azacitidine derivative and antineoplastic antimetabolite. It inhibits DNA methyltransferase to re-activate silent genes, limiting METASTASIS and NEOPLASM DRUG RESISTANCE. Decitabine is used in the treatment of MYELODISPLASTIC SYNDROMES, and ACUTE MYELOID LEUKEMIA.

Molecular weight: 228.21
Formula: C8H12N4O4
CLOGP: -1.90
LIPINSKI: 0
HAC: 8
HDO: 3
TPSA: 120.74
ALOGS: -1.62
ROTB: 2

Status: OFP

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

Drug dosage:

None

ADMET properties:

Property	Value	Reference
MRTD (Maximum Recommended Therapeutic Daily Dose)	4.87 µM/kg/day	Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
Vd (Volume of distribution)	4.60 L/kg	Lombardo F, Berellini G, Obach RS
CL (Clearance)	130 mL/min/kg	Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma)	1 %	Lombardo F, Berellini G, Obach RS
t_half (Half-life)	0.58 hours	Lombardo F, Berellini G, Obach RS

Approvals:

Date	Agency	Company	Orphan
May 2, 2006	FDA	Astex Pharmaceuticals, Inc.

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
Febrile neutropenia	295.51	31.20	131	2656	97536	50504801
Neutropenia	87.22	31.20	69	2718	147896	50454441
Bone marrow failure	82.83	31.20	37	2750	27587	50574750
Pneumonia	82.03	31.20	102	2685	378299	50224038
Acute myeloid leukaemia	67.97	31.20	27	2760	15047	50587290
Thrombocytopenia	59.44	31.20	52	2735	127621	50474716
Pancytopenia	57.75	31.20	43	2744	83987	50518350
Acute myeloid leukaemia recurrent	53.86	31.20	13	2774	1377	50600960
Sepsis	51.79	31.20	49	2738	132876	50469461
Off label use	48.18	31.20	90	2697	474336	50128001
Haematotoxicity	45.81	31.20	17	2770	7878	50594459
Pyrexia	38.34	31.20	72	2715	380131	50222206
Product use in unapproved indication	38.19	31.20	39	2748	115780	50486557
Myelosuppression	36.97	31.20	17	2770	13500	50588837
Splenic abscess	35.91	31.20	6	2781	95	50602242
Myelodysplastic syndrome	32.15	31.20	16	2771	15116	50587221

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
Febrile neutropenia	281.46	26.42	183	4054	112057	29458233
Acute myeloid leukaemia	127.09	26.42	57	4180	16456	29553834
Neutropenia	93.25	26.42	104	4133	131607	29438683
Bone marrow failure	89.07	26.42	53	4184	27396	29542894
Pneumonia	72.49	26.42	148	4089	320024	29250266
Pancytopenia	69.86	26.42	72	4165	83096	29487194
Off label use	62.10	26.42	134	4103	300666	29269624
Infection	56.54	26.42	62	4175	76689	29493601
Sepsis	48.65	26.42	79	4158	142603	29427687
Acute myeloid leukaemia recurrent	46.40	26.42	15	4222	1765	29568525
Acute myeloid leukaemia refractory	45.52	26.42	7	4230	20	29570270
Product use in unapproved indication	45.52	26.42	59	4178	86816	29483474
Aspergillus infection	41.12	26.42	23	4214	10558	29559732
Myelosuppression	38.03	26.42	23	4214	12204	29558086
Pyrexia	37.80	26.42	108	4129	287514	29282776
Thrombocytopenia	35.92	26.42	67	4170	134756	29435534
Platelet count decreased	35.67	26.42	58	4179	104614	29465676
Respiratory failure	29.32	26.42	51	4186	97080	29473210
Mucormycosis	27.94	26.42	14	4223	5144	29565146
Choroidal effusion	27.70	26.42	6	4231	147	29570143
Bacteraemia	27.48	26.42	21	4216	16302	29553988

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
Febrile neutropenia	541.41	26.96	297	6306	187360	64304769
Bone marrow failure	168.53	26.96	87	6516	47865	64444264
Pneumonia	163.68	26.96	240	6363	559336	63932793
Acute myeloid leukaemia	154.97	26.96	69	6534	27394	64464735
Neutropenia	149.17	26.96	151	6452	239473	64252656
Acute myeloid leukaemia recurrent	133.75	26.96	35	6568	2749	64489380
Product use in unapproved indication	116.56	26.96	115	6488	176503	64315626
Sepsis	101.18	26.96	121	6482	230220	64261909
Pancytopenia	90.19	26.96	91	6512	143218	64348911
Haematotoxicity	87.74	26.96	37	6566	12859	64479270
Thrombocytopenia	75.22	26.96	103	6500	223698	64268431
Off label use	73.95	26.96	184	6419	632622	63859507
Myelosuppression	68.88	26.96	38	6565	23792	64468337
Infection	58.94	26.96	83	6520	184797	64307332
Aspergillus infection	55.40	26.96	29	6574	16350	64475779
Pyrexia	53.47	26.96	151	6452	558493	63933636
Acute myeloid leukaemia refractory	49.52	26.96	8	6595	51	64492078
Platelet count decreased	48.61	26.96	72	6531	167639	64324490
Respiratory failure	46.43	26.96	69	6534	161114	64331015
Leukaemia recurrent	45.79	26.96	15	6588	2579	64489550
Bacteraemia	37.43	26.96	27	6576	26884	64465245
Mucormycosis	36.79	26.96	17	6586	7324	64484805
Gene mutation	36.59	26.96	12	6591	2070	64490059
Cardiac failure	34.33	26.96	54	6549	132319	64359810
Anaemia	33.81	26.96	100	6503	378580	64113549
Pneumonia fungal	33.72	26.96	17	6586	8860	64483269
Chronic graft versus host disease	32.92	26.96	15	6588	6261	64485868
Disease progression	31.61	26.96	54	6549	141626	64350503
Organising pneumonia	27.70	26.96	15	6588	9040	64483089

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

Source	Code	Description
ATC	L01BC08	ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS ANTINEOPLASTIC AGENTS ANTIMETABOLITES Pyrimidine analogues
FDA MoA	N0000000233	Nucleic Acid Synthesis Inhibitors
FDA EPC	N0000175595	Nucleoside Metabolic Inhibitor
MeSH PA	D000963	Antimetabolites
MeSH PA	D000964	Antimetabolites, Antineoplastic
MeSH PA	D000970	Antineoplastic Agents
MeSH PA	D004791	Enzyme Inhibitors
MeSH PA	D009676	Noxae

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

Disease	Relation	SNOMED_ID	DOID
Acute myeloid leukemia, disease	indication	91861009
Myelodysplastic syndrome	indication	109995007
Diabetes mellitus	contraindication	73211009	DOID:9351
Kidney disease	contraindication	90708001	DOID:557
Disease of liver	contraindication	235856003	DOID:409
Pregnancy, function	contraindication	289908002
Thrombocytopenic disorder	contraindication	302215000	DOID:1588
Neutropenic disorder	contraindication	303011007	DOID:1227
Breastfeeding (mother)	contraindication	413712001

🐶 Veterinary Drug Use

None

🐶 Veterinary products

None

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation level	Dissociation constant	Type (acidic/basic)
pKa1	12.94	acidic
pKa2	13.68	acidic
pKa3	4.39	Basic
pKa4	2.93	Basic

Orange Book patent data (new drug applications)

Formulation strength	Trade name	Applicant	Application number	Approval date	Type	Dose form	Route	Patent number	Patent expiration date	Patent use
100MG;35MG	INQOVI	OTSUKA	N212576	July 7, 2020	RX	TABLET	ORAL	8618075	Oct. 16, 2028	METHOD FOR INHIBITING CYTIDINE DEAMINASE BY ADMINISTERING CEDAZURIDINE
100MG;35MG	INQOVI	OTSUKA	N212576	July 7, 2020	RX	TABLET	ORAL	8618075	Oct. 16, 2028	METHOD FOR INHIBITING DEGRADATION OF A CDA SUBSTRATE BY ADMINISTERING CEDAZURIDINE
100MG;35MG	INQOVI	OTSUKA	N212576	July 7, 2020	RX	TABLET	ORAL	8268800	Aug. 22, 2030	METHOD FOR INHIBITING CYTIDINE DEAMINASE BY ADMINISTERING CEDAZURIDINE
100MG;35MG	INQOVI	OTSUKA	N212576	July 7, 2020	RX	TABLET	ORAL	8268800	Aug. 22, 2030	METHOD FOR INHIBITING DEGRADATION OF A CDA SUBSTRATE BY ADMINISTERING CEDAZURIDINE
100MG;35MG	INQOVI	OTSUKA	N212576	July 7, 2020	RX	TABLET	ORAL	8268800	Aug. 22, 2030	TREATMENT OF CHRONIC MYELOMONOCYTIC LEUKEMIA
100MG;35MG	INQOVI	OTSUKA	N212576	July 7, 2020	RX	TABLET	ORAL	8268800	Aug. 22, 2030	TREATMENT OF MYELODYSPLASTIC SYNDROME

Orange Book exclusivity data (new drug applications)

Formulation strength	Trade name	Applicant	Application number	Approval date	Type	Dose form	Route	Exclusivity date	Description
100MG;35MG	INQOVI	OTSUKA	N212576	July 7, 2020	RX	TABLET	ORAL	July 7, 2025	NEW CHEMICAL ENTITY
100MG;35MG	INQOVI	OTSUKA	N212576	July 7, 2020	RX	TABLET	ORAL	July 7, 2027	TREATMENT OF ADULT PATIENTS WITH MYELODYSPLASTIC SYNDROMES (MDS), INCLUDING PREVIOUSLY TREATED AND UNTREATED, DE NOVO AND SECONDARY MDS WITH THE FOLLOWING FRENCH-AMERICAN-BRITISH SUBTYPES (REFRACTORY ANEMIA, REFRACTORY ANEMIA WITH RINGED SIDEROBLASTS, REFRACTORY ANEMIA WITH EXCESS BLASTS, AND CHRONIC MYELOMONOCYTIC LEUKEMIA [CMML]) AND INTERMEDIATE-1, INTERMEDIATE-2, AND HIGH-RISK INTERNATIONAL PROGNOSTIC SCORING SYSTEM GROUPS.

Bioactivity Summary:

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	7.52		CHEMBL	CHEMBL
DNA (cytosine-5)-methyltransferase 3A	Enzyme	Q9Y6K1	DNM3A_HUMAN	INHIBITOR				CHEMBL	CHEMBL

External reference:

ID	Source
4025438	VUID
N0000179023	NUI
D03665	KEGG_DRUG
879492-57-6	SECONDARY_CAS_RN
15657	RXNORM
4025438	VANDF
C0049065	UMLSCUI
CHEBI:50131	CHEBI
CHEMBL1201129	ChEMBL_ID
DB01262	DRUGBANK_ID
D000077209	MESH_DESCRIPTOR_UI
451668	PUBCHEM_CID
6374	INN_ID
6805	IUPHAR_LIGAND_ID
776B62CQ27	UNII
203877	MMSL
21366	MMSL
81707	MMSL
d05788	MMSL
011499	NDDF
420517007	SNOMEDCT_US
420759005	SNOMEDCT_US

Pharmaceutical products:

Product	Category	Ingredients	NDC	Form	Quantity	Route	Marketing	Label
decitabine	HUMAN PRESCRIPTION DRUG LABEL	1	0143-9385	INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION	50 mg	INTRAVENOUS	ANDA	28 sections
Decitabine	Human Prescription Drug Label	1	0781-3296	INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION	50 mg	INTRAVENOUS	ANDA	27 sections
Decitabine	HUMAN PRESCRIPTION DRUG LABEL	1	16714-749	INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION	50 mg	INTRAVENOUS	ANDA	25 sections
Decitabine	HUMAN PRESCRIPTION DRUG LABEL	1	16714-928	INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION	50 mg	INTRAVENOUS	ANDA	27 sections
Decitabine	HUMAN PRESCRIPTION DRUG LABEL	1	16729-224	INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION	50 mg	INTRAVENOUS	ANDA	27 sections
Decitabine	HUMAN PRESCRIPTION DRUG LABEL	1	16729-224	INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION	50 mg	INTRAVENOUS	ANDA	27 sections
decitabine	HUMAN PRESCRIPTION DRUG LABEL	1	25021-231	INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION	50 mg	INTRAVENOUS	ANDA	27 sections
Decitabine	HUMAN PRESCRIPTION DRUG LABEL	1	43598-348	INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION	50 mg	INTRAVENOUS	ANDA	27 sections
Decitabine	HUMAN PRESCRIPTION DRUG LABEL	1	43598-427	INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION	50 mg	INTRAVENOUS	ANDA	27 sections
DECITABINE	HUMAN PRESCRIPTION DRUG LABEL	1	50742-430	INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION	50 mg	INTRAVENOUS	ANDA	24 sections
Decitabine	HUMAN PRESCRIPTION DRUG LABEL	1	55111-556	INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION	50 mg	INTRAVENOUS	ANDA	27 sections
Decitabine	Human Prescription Drug Label	1	55150-376	INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION	50 mg	INTRAVENOUS	ANDA	27 sections
Dacogen	HUMAN PRESCRIPTION DRUG LABEL	1	59148-046	INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION	50 mg	INTRAVENOUS	NDA	30 sections
Decitabine	HUMAN PRESCRIPTION DRUG LABEL	1	63323-825	INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION	50 mg	INTRAVENOUS	ANDA	27 sections
Decitabine	HUMAN PRESCRIPTION DRUG LABEL	1	64679-067	INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION	50 mg	INTRAVENOUS	ANDA	24 sections
INQOVI	HUMAN PRESCRIPTION DRUG LABEL	2	64842-0727	TABLET, FILM COATED	35 mg	ORAL	NDA	31 sections
INQOVI	HUMAN PRESCRIPTION DRUG LABEL	2	64842-0727	TABLET, FILM COATED	35 mg	ORAL	NDA	31 sections
Decitabine	HUMAN PRESCRIPTION DRUG LABEL	1	67184-0535	INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION	50 mg	INTRAVENOUS	ANDA	28 sections
Decitabine	HUMAN PRESCRIPTION DRUG LABEL	1	67457-316	INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION	50 mg	INTRAVENOUS	ANDA	27 sections
Decitabine	HUMAN PRESCRIPTION DRUG LABEL	1	68001-422	INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION	50 mg	INTRAVENOUS	ANDA	27 sections
decitabine	Human Prescription Drug Label	1	68083-528	INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION	50 mg	INTRAVENOUS	ANDA	27 sections
decitabine	HUMAN PRESCRIPTION DRUG LABEL	1	68180-738	INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION	50 mg	INTRAVENOUS	ANDA	25 sections
Decitabine	HUMAN PRESCRIPTION DRUG LABEL	1	69097-285	INJECTION	50 mg	INTRAVENOUS	ANDA	24 sections
Decitabine	HUMAN PRESCRIPTION DRUG LABEL	1	69097-905	INJECTION	50 mg	INTRAVENOUS	ANDA	21 sections
Decitabine	Human Prescription Drug Label	1	69539-115	INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION	50 mg	INTRAVENOUS	ANDA	27 sections
Decitabine	HUMAN PRESCRIPTION DRUG LABEL	1	70121-1644	INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION	50 mg	INTRAVENOUS	ANDA	28 sections
Decitabine	HUMAN PRESCRIPTION DRUG LABEL	1	70860-219	INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION	50 mg	INTRAVENOUS	ANDA	28 sections
Decitabine	HUMAN PRESCRIPTION DRUG LABEL	1	71288-119	INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION	50 mg	INTRAVENOUS	ANDA	27 sections
Decitabine	Human Prescription Drug Label	1	72205-031	INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION	50 mg	INTRAVENOUS	ANDA	27 sections
Decitabine	Human Prescription Drug Label	1	72205-036	INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION	50 mg	INTRAVENOUS	ANDA	27 sections