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:

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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
S (Water solubility)	10 mg/mL	Bocci G, Oprea TI, Benet LZ
fu (Fraction unbound in plasma)	1 %	Lombardo F, Berellini G, Obach RS
BDDCS (Biopharmaceutical Drug Disposition Classification System)	1	Bocci G, Oprea TI, Benet LZ
t_half (Half-life)	0.58 hours	Lombardo F, Berellini G, Obach RS

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Approvals:

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

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	369.34	28.96	163	3385	118286	63367188
Neutropenia	98.62	28.96	80	3468	174925	63310549
Myelosuppression	94.44	28.96	39	3509	23664	63461810
Pancytopenia	92.56	28.96	61	3487	96872	63388602
Bone marrow failure	89.69	28.96	40	3508	29250	63456224
Pneumonia	89.41	28.96	118	3430	456649	63028825
Thrombocytopenia	78.60	28.96	66	3482	151091	63334383
Acute myeloid leukaemia	74.39	28.96	30	3518	17117	63468357
Acute myeloid leukaemia recurrent	66.89	28.96	16	3532	1607	63483867
Off label use	63.65	28.96	125	3423	674337	62811137

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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	326.76	25.21	221	5070	136628	34815012
Acute myeloid leukaemia	137.05	25.21	63	5228	18207	34933433
Neutropenia	117.64	25.21	131	5160	156647	34794993
Off label use	99.49	25.21	204	5087	419320	34532320
Bone marrow failure	93.34	25.21	57	5234	29196	34922444
Pancytopenia	88.02	25.21	89	5202	95068	34856572
Myelosuppression	86.76	25.21	47	5244	19218	34932422
Infection	85.86	25.21	86	5205	90829	34860811
Pneumonia	76.06	25.21	168	5123	362459	34589181
Thrombocytopenia	71.32	25.21	102	5189	156145	34795495

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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	661.01	25.35	365	7887	230634	79505502
Neutropenia	186.05	25.35	186	8066	287524	79448612
Bone marrow failure	182.28	25.35	94	8158	51013	79685123
Pneumonia	177.48	25.35	274	7978	659972	79076164
Acute myeloid leukaemia	174.73	25.35	78	8174	30807	79705329
Myelosuppression	169.80	25.35	83	8169	40213	79695923
Acute myeloid leukaemia recurrent	164.33	25.35	43	8209	3340	79732796
Product use in unapproved indication	142.04	25.35	151	8101	250208	79485928
Pancytopenia	137.16	25.35	123	8129	165622	79570514
Thrombocytopenia	133.11	25.35	150	8102	265109	79471027

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FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

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Source	Code	Description
ATC	L01BC08	ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS ANTINEOPLASTIC AGENTS ANTIMETABOLITES Pyrimidine analogues
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
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

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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	12.94	acidic
pKa2	13.68	acidic
pKa3	4.39	Basic
pKa4	2.93	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
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

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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;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.

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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	7.52		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
011499	NDDF
15657	RXNORM
203877	MMSL
21366	MMSL
4025438	VUID
4025438	VANDF
420517007	SNOMEDCT_US
420759005	SNOMEDCT_US
451668	PUBCHEM_CID
6374	INN_ID

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Pharmaceutical products:

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Product	Category	Ingredients	NDC	Form	Quantity	Route	Marketing	Label
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	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	28 sections
decitabine	HUMAN PRESCRIPTION DRUG LABEL	1	25021-231	INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION	50 mg	INTRAVENOUS	ANDA	28 sections
Decitabine	HUMAN PRESCRIPTION DRUG LABEL	1	43598-348	INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION	50 mg	INTRAVENOUS	ANDA	27 sections

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