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

Stem definition	Drug id	CAS RN
	1112	33419-42-0

Description:

Molecule	Description
Molfile Inchi Smiles Synonyms: etoposide etosid fytosid toposar zuyeyidal VP-16	A semisynthetic derivative of PODOPHYLLOTOXIN that exhibits antitumor activity. Etoposide inhibits DNA synthesis by forming a complex with topoisomerase II and DNA. This complex induces breaks in double stranded DNA and prevents repair by topoisomerase II binding. Accumulated breaks in DNA prevent entry into the mitotic phase of cell division, and lead to cell death. Etoposide acts primarily in the G2 and S phases of the cell cycle. Molecular weight: 588.56 Formula: C29H32O13 CLOGP: 0.59 LIPINSKI: 2 HAC: 13 HDO: 3 TPSA: 160.83 ALOGS: -2.78 ROTB: 5 Status: OFP Legend: OFP - off patent OFM - off market ONP - on patent

Molecule

Description

Molfile Inchi Smiles

Synonyms:

etoposide
etosid
fytosid
toposar
zuyeyidal
VP-16

A semisynthetic derivative of PODOPHYLLOTOXIN that exhibits antitumor activity. Etoposide inhibits DNA synthesis by forming a complex with topoisomerase II and DNA. This complex induces breaks in double stranded DNA and prevents repair by topoisomerase II binding. Accumulated breaks in DNA prevent entry into the mitotic phase of cell division, and lead to cell death. Etoposide acts primarily in the G2 and S phases of the cell cycle.

Molecular weight: 588.56
Formula: C29H32O13
CLOGP: 0.59
LIPINSKI: 2
HAC: 13
HDO: 3
TPSA: 160.83
ALOGS: -2.78
ROTB: 5

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)	6.30 µM/kg/day	Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability)	52 %	Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
t_half (Half-life)	5.70 hours	Lombardo F, Berellini G, Obach RS
BDDCS (Biopharmaceutical Drug Disposition Classification System)	4	Bocci G, Oprea TI, Benet LZ
EoM (Fraction excreted unchanged in urine)	38 %	Benet LZ, Broccatelli F, Oprea TI
CL (Clearance)	0.50 mL/min/kg	Lombardo F, Berellini G, Obach RS
Vd (Volume of distribution)	0.18 L/kg	Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma)	0.12 %	Lombardo F, Berellini G, Obach RS
S (Water solubility)	0.11 mg/mL	Bocci G, Oprea TI, Benet LZ

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Approvals:

Date	Agency	Company	Orphan
March 26, 2019	PMDA	BRISTOL-MYERS SQUIBB K.K.
Nov. 10, 1983	FDA

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	3122.49	17.28	1717	57632	116732	63312941
Neutropenia	1309.99	17.28	1173	58176	173832	63255841
Mucosal inflammation	1103.46	17.28	633	58716	46295	63383378
Pancytopenia	935.79	17.28	753	58596	96180	63333493
Disease progression	843.04	17.28	785	58564	121973	63307700
Bone marrow failure	819.04	17.28	443	58906	28847	63400826
Thrombocytopenia	804.55	17.28	841	58508	150316	63279357
Acute myeloid leukaemia	660.87	17.28	322	59027	16825	63412848
Haematotoxicity	556.98	17.28	238	59111	9138	63420535
Product use in unapproved indication	548.06	17.28	752	58597	178328	63251345

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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	3196.52	14.45	2598	79084	134251	34740998
Neutropenia	1015.96	14.45	1519	80163	155259	34719990
Mucosal inflammation	793.80	14.45	684	80998	37938	34837311
Disease progression	774.14	14.45	1099	80583	106978	34768271
Pancytopenia	747.81	14.45	1012	80670	94145	34781104
Myelosuppression	730.85	14.45	492	81190	18773	34856476
Bone marrow failure	689.76	14.45	561	81121	28692	34846557
Off label use	678.91	14.45	2330	79352	417194	34458055
Acute myeloid leukaemia	623.09	14.45	437	81245	17833	34857416
Thrombocytopenia	588.92	14.45	1193	80489	155054	34720195

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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	5815.59	14.56	3961	125001	227038	79388388
Neutropenia	2065.51	14.56	2429	126533	285281	79330145
Pancytopenia	1660.87	14.56	1670	127292	164075	79451351
Mucosal inflammation	1638.05	14.56	1187	127775	74393	79541033
Bone marrow failure	1404.15	14.56	929	128033	50178	79565248
Thrombocytopenia	1281.89	14.56	1844	127118	263415	79352011
Disease progression	1277.92	14.56	1531	127431	182831	79432595
Acute myeloid leukaemia	1128.78	14.56	673	128289	30212	79585214
Off label use	1073.84	14.56	3553	125409	903662	78711764
Product use in unapproved indication	1046.71	14.56	1627	127335	248732	79366694

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FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

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Source	Code	Description
ATC	L01CB01	ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS ANTINEOPLASTIC AGENTS PLANT ALKALOIDS AND OTHER NATURAL PRODUCTS Podophyllotoxin derivatives
CHEBI has role	CHEBI:35610	antineoplastic agents
CHEBI has role	CHEBI:59517	DNA synthesis inhibitors
FDA EPC	N0000175609	Topoisomerase Inhibitor
FDA MoA	N0000000176	Topoisomerase Inhibitors
MeSH PA	D000970	Antineoplastic Agents
MeSH PA	D000972	Antineoplastic Agents, Phytogenic
MeSH PA	D004791	Enzyme Inhibitors
MeSH PA	D059005	Topoisomerase II Inhibitors
MeSH PA	D059003	Topoisomerase Inhibitors

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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
Small cell carcinoma of lung	indication	254632001	DOID:5409
Malignant tumor of testis	indication	363449006	DOID:2998
Treatment prior to tumor-specific T-cell infusion therapy	indication
Allogeneic bone marrow transplantation	off-label use	58390007
Ewing's sarcoma	off-label use	76909002	DOID:3369
Acute myeloid leukemia, disease	off-label use	91861009
Kaposi's sarcoma	off-label use	109385007
Diffuse non-Hodgkin's lymphoma, large cell	off-label use	109969005
Multiple myeloma	off-label use	109989006	DOID:9538
Hodgkin's disease	off-label use	118599009

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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	11.96	acidic
pKa2	13.08	acidic
pKa3	13.86	acidic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

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Target	Class	Pharos	UniProt	Action	Type	Activity value (-log[M])	Bioact source	MoA source
DNA topoisomerase 2-alpha	Enzyme	P11388	TOP2A_HUMAN	INHIBITOR	IC50	7.30	IUPHAR	CHEMBL
Canalicular multispecific organic anion transporter 1	Transporter	Q92887	MRP2_HUMAN		Km	3.21	WOMBAT-PK
Nuclear receptor subfamily 1 group I member 2	Nuclear hormone receptor	O75469	NR1I2_HUMAN				WOMBAT-PK
Multidrug resistance-associated protein 1	Transporter	P33527	MRP1_HUMAN				WOMBAT-PK
ATP-binding cassette sub-family G member 2	Transporter	Q9UNQ0	ABCG2_HUMAN				WOMBAT-PK
Multidrug resistance-associated protein 6	Transporter	O95255	MRP6_HUMAN				WOMBAT-PK
Canalicular multispecific organic anion transporter 2	Transporter	O15438	MRP3_HUMAN				WOMBAT-PK
DNA topoisomerase 2-beta	Enzyme	Q02880	TOP2B_HUMAN		IC50	7.16	CHEMBL
Multidrug resistance protein 1	Transporter	P08183	MDR1_HUMAN		Ki	3.28	WOMBAT-PK
Arachidonate 15-lipoxygenase	Enzyme		LOX15_RABIT		IC50	5.50	DRUG MATRIX

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External reference:

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ID	Source
EVP	PDB_CHEM_ID
002674	NDDF
220347	RXNORM
36462	PUBCHEM_CID
3835	INN_ID
387316009	SNOMEDCT_US
4018141	VUID
4018141	VANDF
4209	MMSL
4709	MMSL

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Pharmaceutical products:

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Product	Category	Ingredients	NDC	Form	Quantity	Route	Marketing	Label
Etoposide	HUMAN PRESCRIPTION DRUG LABEL	1	0143-9376	INJECTION	20 mg	INTRAVENOUS	ANDA	22 sections
Etoposide	HUMAN PRESCRIPTION DRUG LABEL	1	0143-9510	INJECTION	20 mg	INTRAVENOUS	ANDA	22 sections
Etoposide	HUMAN PRESCRIPTION DRUG LABEL	1	0143-9511	INJECTION	20 mg	INTRAVENOUS	ANDA	22 sections
Etoposide	HUMAN PRESCRIPTION DRUG LABEL	1	0143-9512	INJECTION	20 mg	INTRAVENOUS	ANDA	22 sections
Etoposide	HUMAN PRESCRIPTION DRUG LABEL	1	0378-3266	CAPSULE	50 mg	ORAL	ANDA	24 sections
Etoposide	HUMAN PRESCRIPTION DRUG LABEL	1	16729-114	INJECTION	20 mg	INTRAVENOUS	ANDA	22 sections
Etoposide	HUMAN PRESCRIPTION DRUG LABEL	1	63323-104	INJECTION, SOLUTION	20 mg	INTRAVENOUS	ANDA	14 sections
Etoposide	HUMAN PRESCRIPTION DRUG LABEL	1	63323-104	INJECTION, SOLUTION	20 mg	INTRAVENOUS	ANDA	14 sections
Etoposide	HUMAN PRESCRIPTION DRUG LABEL	1	68001-265	INJECTION	20 mg	INTRAVENOUS	ANDA	22 sections
Toposar	HUMAN PRESCRIPTION DRUG LABEL	1	0703-5653	INJECTION, SOLUTION, CONCENTRATE	20 mg	INTRAVENOUS	ANDA	24 sections

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