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cytarabine 🐶 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	770	147-94-4

Description:

Molecule	Description
Molfile Inchi Smiles Synonyms: cytarabine hydrochloride cytarabine arabinocytosine Arabinoside C aracytidine cyclocide cytarabin cytarabinoside cytosine beta-D-arabinofuranoside cytarabine liposome cytarabine HCl	A pyrimidine nucleoside analog that is used mainly in the treatment of leukemia, especially acute non-lymphoblastic leukemia. Cytarabine is an antimetabolite antineoplastic agent that inhibits the synthesis of DNA. Its actions are specific for the S phase of the cell cycle. It also has antiviral and immunosuppressant properties. (From Martindale, The Extra Pharmacopoeia, 30th ed, p472) Molecular weight: 243.22 Formula: C9H13N3O5 CLOGP: -2.19 LIPINSKI: 0 HAC: 8 HDO: 4 TPSA: 128.61 ALOGS: -0.74 ROTB: 2 Status: OFP Legend: OFP - off patent OFM - off market ONP - on patent

Molecule

Description

Molfile Inchi Smiles

Synonyms:

cytarabine hydrochloride
cytarabine
arabinocytosine
Arabinoside C
aracytidine
cyclocide
cytarabin
cytarabinoside
cytosine beta-D-arabinofuranoside
cytarabine liposome
cytarabine HCl

A pyrimidine nucleoside analog that is used mainly in the treatment of leukemia, especially acute non-lymphoblastic leukemia. Cytarabine is an antimetabolite antineoplastic agent that inhibits the synthesis of DNA. Its actions are specific for the S phase of the cell cycle. It also has antiviral and immunosuppressant properties. (From Martindale, The Extra Pharmacopoeia, 30th ed, p472)

Molecular weight: 243.22
Formula: C9H13N3O5
CLOGP: -2.19
LIPINSKI: 0
HAC: 8
HDO: 4
TPSA: 128.61
ALOGS: -0.74
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
CL (Clearance)	41.67 mL/min/kg	Lombardo F, Berellini G, Obach RS
BA (Bioavailability)	20 %	Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
MRTD (Maximum Recommended Therapeutic Daily Dose)	11.10 µM/kg/day	Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
EoM (Fraction excreted unchanged in urine)	11 %	Benet LZ, Broccatelli F, Oprea TI
BDDCS (Biopharmaceutical Drug Disposition Classification System)	1	Benet LZ, Broccatelli F, Oprea TI
fu (Fraction unbound in plasma)	0.87 %	Lombardo F, Berellini G, Obach RS
Vd (Volume of distribution)	0.67 L/kg	Lombardo F, Berellini G, Obach RS
t_half (Half-life)	0.17 hours	Lombardo F, Berellini G, Obach RS

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Approvals:

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Date	Agency	Company
Aug. 21, 2020	PMDA	Nippon Shinyaku Co., Ltd.
July 11, 2001	EMA	PACIRA LIMITED
June 17, 1969	FDA

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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	3938.73	18.51	1958	53369	116491	63317204
Mucosal inflammation	720.18	18.51	470	54857	46458	63387237
Neutropenia	714.19	18.51	819	54508	174186	63259509
Febrile bone marrow aplasia	710.78	18.51	260	55067	7065	63426630
Bone marrow failure	700.07	18.51	390	54937	28900	63404795
Pancytopenia	649.45	18.51	593	54734	96340	63337355
Thrombocytopenia	620.80	18.51	710	54617	150447	63283248
Venoocclusive liver disease	603.74	18.51	207	55120	4628	63429067
Septic shock	599.93	18.51	483	54844	66146	63367549
Sepsis	526.22	18.51	657	54670	152466	63281229

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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	4012.20	14.08	2900	74073	133949	34746009
Neutropenia	764.24	14.08	1292	75681	155486	34724472
Venoocclusive liver disease	737.01	14.08	357	76616	7609	34872349
Bone marrow failure	708.42	14.08	556	76417	28697	34851261
Mucosal inflammation	692.60	14.08	617	76356	38005	34841953
Myelosuppression	593.16	14.08	423	76550	18842	34861116
Febrile bone marrow aplasia	564.17	14.08	301	76672	7908	34872050
Haematotoxicity	539.46	14.08	292	76681	7902	34872056
Pancytopenia	497.14	14.08	810	76163	94347	34785611
Thrombocytopenia	464.37	14.08	1046	75927	155201	34724757

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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	7330.64	14.95	4460	115815	226539	79397574
Bone marrow failure	1369.54	14.95	891	119384	50216	79573897
Neutropenia	1363.60	14.95	1910	118365	285800	79338313
Mucosal inflammation	1221.82	14.95	969	119306	74611	79549502
Pancytopenia	1030.62	14.95	1259	119016	164486	79459627
Haematotoxicity	1012.43	14.95	486	119789	15033	79609080
Thrombocytopenia	1002.99	14.95	1585	118690	263674	79360439
Venoocclusive liver disease	924.00	14.95	419	119856	11352	79612761
Septic shock	915.14	14.95	1024	119251	121777	79502336
Myelosuppression	903.05	14.95	629	119646	39667	79584446

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FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

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Source	Code	Description
ATC	L01BC01	ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS ANTINEOPLASTIC AGENTS ANTIMETABOLITES Pyrimidine analogues
ATC	L01XY01	ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS ANTINEOPLASTIC AGENTS OTHER ANTINEOPLASTIC AGENTS Combinations of antineoplastic agents
CHEBI has role	CHEBI:22587	antiviral agents
CHEBI has role	CHEBI:35221	antimetabolite
CHEBI has role	CHEBI:35610	antineoplastic agents
CHEBI has role	CHEBI:35705	immunosuppressive agents
FDA EPC	N0000175595	Nucleoside Metabolic Inhibitor
FDA MoA	N0000000233	Nucleic Acid Synthesis Inhibitors
MeSH PA	D000890	Anti-Infective Agents
MeSH PA	D000963	Antimetabolites

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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 lymphoid leukemia	indication	91857003	DOID:9952
Acute myeloid leukemia, disease	indication	91861009
Acute promyelocytic leukemia, FAB M3	indication	110004001
Lymphomatous meningitis	indication	426128009
Meningeal Leukemia	indication
Allogeneic bone marrow transplantation	off-label use	58390007
Chronic myeloid leukemia	off-label use	92818009	DOID:8552
Diffuse non-Hodgkin's lymphoma, large cell	off-label use	109969005
Myelodysplastic syndrome	off-label use	109995007
Burkitt's lymphoma	off-label use	118617000

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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	11.91	acidic
pKa2	12.58	acidic
pKa3	12.97	acidic
pKa4	4.04	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;44MG	VYXEOS	CELATOR PHARMS	N209401	Aug. 3, 2017	RX	POWDER	INTRAVENOUS	8431806	April 22, 2025	FOR THE TREATMENT OF NEWLY-DIAGNOSED THERAPY-RELATED ACUTE MYELOID LEUKEMIA (T-AML) OR AML WITH MYELODYSPLASIA-RELATED CHANGES (AML-MRC) IN ADULTS AND PEDIATRIC PATIENTS 1 YEAR AND OLDER
100MG;44MG	VYXEOS	CELATOR PHARMS	N209401	Aug. 3, 2017	RX	POWDER	INTRAVENOUS	7850990	Jan. 23, 2027	FOR THE TREATMENT OF NEWLY-DIAGNOSED THERAPY-RELATED ACUTE MYELOID LEUKEMIA (T-AML) OR AML WITH MYELODYSPLASIA-RELATED CHANGES (AML-MRC) IN ADULTS AND PEDIATRIC PATIENTS 1 YEAR AND OLDER
100MG;44MG	VYXEOS	CELATOR PHARMS	N209401	Aug. 3, 2017	RX	POWDER	INTRAVENOUS	8022279	Sept. 14, 2027	FOR THE TREATMENT OF NEWLY-DIAGNOSED THERAPY-RELATED ACUTE MYELOID LEUKEMIA (T-AML) OR AML WITH MYELODYSPLASIA-RELATED CHANGES (AML-MRC) IN ADULTS AND PEDIATRIC PATIENTS 1 YEAR AND OLDER
100MG;44MG	VYXEOS	CELATOR PHARMS	N209401	Aug. 3, 2017	RX	POWDER	INTRAVENOUS	8092828	April 1, 2029	FOR THE TREATMENT OF NEWLY-DIAGNOSED THERAPY-RELATED ACUTE MYELOID LEUKEMIA (T-AML) OR AML WITH MYELODYSPLASIA-RELATED CHANGES (AML-MRC) IN ADULTS AND PEDIATRIC PATIENTS 1 YEAR AND OLDER
100MG;44MG	VYXEOS	CELATOR PHARMS	N209401	Aug. 3, 2017	RX	POWDER	INTRAVENOUS	10028912	Oct. 15, 2032	METHOD OF ADMINISTERING A RECONSTITUTED LIPOSOMAL COMPOSITION CONTAINING CYTARABINE AND DAUNORUBICIN TO TREAT NEWLY-DIAGNOSED THERAPY-RELATED AML (T-AML) OR AML WITH MYELODYSPLASIA-RELATED CHANGES (AML-MRC) IN PATIENTS 1 YEAR AND OLDER
100MG;44MG	VYXEOS	CELATOR PHARMS	N209401	Aug. 3, 2017	RX	POWDER	INTRAVENOUS	10028912	Oct. 15, 2032	METHOD OF RECONSTITUTING A LYOPHILIZED LIPOSOMAL COMPOSITION FOR ADMINISTERING CYTARABINE AND DAUNORUBICIN TO TREAT NEWLY-DIAGNOSED THERAPY-RELATED AML (T-AML) OR AML WITH MYELODYSPLASIA-RELATED CHANGES (AML-MRC) IN PATIENTS 1 YEAR AND OLDER
100MG;44MG	VYXEOS	CELATOR PHARMS	N209401	Aug. 3, 2017	RX	POWDER	INTRAVENOUS	10166184	Oct. 15, 2032	METHOD OF RECONSTITUTING A LYOPHILIZED LIPOSOMAL COMPOSITION FOR ADMINISTERING CYTARABINE AND DAUNORUBICIN TO TREAT NEWLY-DIAGNOSED THERAPY-RELATED AML (T-AML) OR AML WITH MYELODYSPLASIA-RELATED CHANGES (AML-MRC) IN PATIENTS 1 YEAR AND OLDER
100MG;44MG	VYXEOS	CELATOR PHARMS	N209401	Aug. 3, 2017	RX	POWDER	INTRAVENOUS	10835492	Oct. 15, 2032	METHOD OF ADMINISTERING A RECONSTITUTED LIPOSOMAL COMPOSITION CONTAINING CYTARABINE AND DAUNORUBICIN TO TREAT NEWLY-DIAGNOSED THERAPY-RELATED AML (T-AML) OR AML WITH MYELODYSPLASIA-RELATED CHANGES (AML-MRC) IN PATIENTS 1 YEAR AND OLDER

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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;44MG	VYXEOS	CELATOR PHARMS	N209401	Aug. 3, 2017	RX	POWDER	INTRAVENOUS	March 30, 2024	NEW PATIENT POPULATION
100MG;44MG	VYXEOS	CELATOR PHARMS	N209401	Aug. 3, 2017	RX	POWDER	INTRAVENOUS	Aug. 3, 2024	TREATMENT OF ADULTS WITH NEWLY DIAGNOSED THERAPY-RELATED ACUTE MYELOID LEUKEMIA (T-AML) OR AML WITH MYELODYSPLASIA-RELATED CHANGES (AML-MRC)
100MG;44MG	VYXEOS	CELATOR PHARMS	N209401	Aug. 3, 2017	RX	POWDER	INTRAVENOUS	March 30, 2028	TREATMENT OF NEWLY-DIAGNOSED THERAPY-RELATED ACUTE MYELOID LEUKEMIA (T-AML) OR AML WITH MYELODYSPLASIA-RELATED CHANGES (AML-MRC) IN PEDIATRIC PATIENTS AGES 1 YEAR AND OLDER

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Bioactivity Summary:

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Target	Class	Pharos	UniProt	Action	Type	Activity value (-log[M])	Bioact source	MoA source
DNA polymerase (alpha/delta/epsilon)	Enzyme	P09884 P28340 Q07864	DPOLA_HUMAN DPOD1_HUMAN DPOE1_HUMAN	INHIBITOR			CHEMBL	CHEMBL
Prostatic acid phosphatase	Enzyme	P15309	PPAP_HUMAN		GI50	7	WOMBAT-PK
DNA polymerase beta	Enzyme	P06746	DPOLB_HUMAN				WOMBAT-PK
E3 ubiquitin-protein ligase Mdm2	Nuclear other	Q00987	MDM2_HUMAN		IC50	7.70	CHEMBL
Enoyl-[acyl-carrier-protein] reductase [NADH]	Enzyme		Q5NGQ3_FRATT		IC50	4.23	CHEMBL

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External reference:

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ID	Source
AR3	PDB_CHEM_ID
002649	NDDF
007798	NDDF
017308	NDDF
04079A1RDZ	UNII
116089003	SNOMEDCT_US
17070	MMSL
1709	INN_ID
3041	RXNORM
372	MMSL

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Pharmaceutical products:

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Product	Category	Ingredients	NDC	Form	Quantity	Route	Marketing	Label
cytarabine	HUMAN PRESCRIPTION DRUG LABEL	1	25021-223	INJECTION, SOLUTION	100 mg	INTRAVENOUS	ANDA	24 sections
cytarabine	HUMAN PRESCRIPTION DRUG LABEL	1	25021-229	INJECTION, SOLUTION	20 mg	INTRAVENOUS	ANDA	24 sections
CYTARABINE	HUMAN PRESCRIPTION DRUG LABEL	1	61703-303	INJECTION, SOLUTION	20 mg	INTRAVENOUS	ANDA	22 sections
CYTARABINE	HUMAN PRESCRIPTION DRUG LABEL	1	61703-303	INJECTION, SOLUTION	20 mg	INTRAVENOUS	ANDA	22 sections
Cytarabine	HUMAN PRESCRIPTION DRUG LABEL	1	61703-304	INJECTION, SOLUTION	20 mg	INTRAVENOUS	ANDA	24 sections
Cytarabine	HUMAN PRESCRIPTION DRUG LABEL	1	61703-304	INJECTION, SOLUTION	20 mg	INTRAVENOUS	ANDA	24 sections
Cytarabine	HUMAN PRESCRIPTION DRUG LABEL	1	61703-305	INJECTION, SOLUTION	20 mg	INTRAVENOUS	ANDA	24 sections
Cytarabine	HUMAN PRESCRIPTION DRUG LABEL	1	61703-305	INJECTION, SOLUTION	20 mg	INTRAVENOUS	ANDA	24 sections
Cytarabine	HUMAN PRESCRIPTION DRUG LABEL	1	61703-319	INJECTION, SOLUTION	100 mg	INTRAVENOUS	ANDA	16 sections
Cytarabine	HUMAN PRESCRIPTION DRUG LABEL	1	61703-319	INJECTION, SOLUTION	100 mg	INTRAVENOUS	ANDA	16 sections

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