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

Stem definition	Drug id	CAS RN
antineoplastics, topoisomerase I inhibitors	1482	97682-44-5

Description:

Molecule	Description
Molfile Inchi Smiles Synonyms: irinotecan liposome injection onivyde irinotecan liposome irinotecan irinotecan hydrochloride irinotecan hydrochloride hydrate irinotecan hydrochloride trihydrate irinotecan HCl	Irinotecan is a derivative of camptothecin. Camptothecins act as specific inhibitors of the enzyme DNA topoisomerase I. Irinotecan and its active metabolite SN-38 bind reversibly to the topoisomerase I-DNA complex and induce single-strand DNA lesions which block the DNA replication fork and are responsible for the cytotoxicity. Irinotecan is metabolized by carboxylesterase to SN-38. SN-38 is approximately 1000 times as potent as irinotecan as an inhibitor of topoisomerase I purified from human and rodent tumour cell lines. Molecular weight: 586.69 Formula: C33H38N4O6 CLOGP: 3.07 LIPINSKI: 1 HAC: 10 HDO: 1 TPSA: 112.51 ALOGS: -3.74 ROTB: 5 Status: OFP Legend: OFP - off patent OFM - off market ONP - on patent

Molecule

Description

Molfile Inchi Smiles

Synonyms:

irinotecan liposome injection
onivyde
irinotecan liposome
irinotecan
irinotecan hydrochloride
irinotecan hydrochloride hydrate
irinotecan hydrochloride trihydrate
irinotecan HCl

Irinotecan is a derivative of camptothecin. Camptothecins act as specific inhibitors of the enzyme DNA topoisomerase I. Irinotecan and its active metabolite SN-38 bind reversibly to the topoisomerase I-DNA complex and induce single-strand DNA lesions which block the DNA replication fork and are responsible for the cytotoxicity. Irinotecan is metabolized by carboxylesterase to SN-38. SN-38 is approximately 1000 times as potent as irinotecan as an inhibitor of topoisomerase I purified from human and rodent tumour cell lines.

Molecular weight: 586.69
Formula: C33H38N4O6
CLOGP: 3.07
LIPINSKI: 1
HAC: 10
HDO: 1
TPSA: 112.51
ALOGS: -3.74
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
t_half (Half-life)	9 hours	Lombardo F, Berellini G, Obach RS
BA (Bioavailability)	8 %	Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
CL (Clearance)	7 mL/min/kg	Lombardo F, Berellini G, Obach RS
Vd (Volume of distribution)	3.50 L/kg	Lombardo F, Berellini G, Obach RS
EoM (Fraction excreted unchanged in urine)	16.70 %	Benet LZ, Broccatelli F, Oprea TI
S (Water solubility)	10 mg/mL	Benet LZ, Broccatelli F, Oprea TI
BDDCS (Biopharmaceutical Drug Disposition Classification System)	1	Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose)	0.75 µM/kg/day	Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
fu (Fraction unbound in plasma)	0.51 %	Lombardo F, Berellini G, Obach RS

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Approvals:

Date	Agency	Company	Orphan
June 14, 1996	FDA	PFIZER INC
March 25, 2020	PMDA	Nihon Servier Co., Ltd

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
Neutropenia	859.66	22.08	702	30718	174303	63283299
Diarrhoea	790.39	22.08	1323	30097	714043	62743559
Disease progression	762.04	22.08	566	30854	122192	63335410
Neuropathy peripheral	478.70	22.08	418	31002	113249	63344353
Myelosuppression	334.71	22.08	184	31236	23519	63434083
Malignant neoplasm progression	331.43	22.08	295	31125	81826	63375776
Febrile neutropenia	308.77	22.08	335	31085	118114	63339488
Mucosal inflammation	287.28	22.08	215	31205	46713	63410889
Neurotoxicity	270.91	22.08	143	31277	16847	63440755
Vomiting	262.72	22.08	735	30685	558882	62898720

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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
Diarrhoea	1217.47	18.10	1892	40826	388020	34526193
Disease progression	889.61	18.10	860	41858	107217	34806996
Neutropenia	798.78	18.10	968	41750	155810	34758403
Skin toxicity	426.01	18.10	175	42543	4609	34909604
Dermatitis acneiform	395.28	18.10	179	42539	6010	34908203
Myelosuppression	379.09	18.10	256	42462	19009	34895204
Neuropathy peripheral	355.63	18.10	472	42246	82791	34831422
Palmar-plantar erythrodysaesthesia syndrome	354.12	18.10	233	42485	16562	34897651
Stomatitis	349.77	18.10	339	42379	42175	34872038
Neoplasm progression	300.60	18.10	240	42478	23060	34891153

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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
Diarrhoea	1822.25	17.51	2900	64551	877589	78799348
Neutropenia	1664.60	17.51	1597	65854	286113	79390824
Disease progression	1454.10	17.51	1220	66231	183142	79493795
Neuropathy peripheral	882.34	17.51	820	66631	140485	79536452
Myelosuppression	632.51	17.51	405	67046	39891	79637046
Dermatitis acneiform	609.03	17.51	251	67200	9742	79667195
Palmar-plantar erythrodysaesthesia syndrome	532.33	17.51	338	67113	32796	79644141
Skin toxicity	507.23	17.51	209	67242	8105	79668832
Neoplasm progression	503.72	17.51	388	67063	51294	79625643
Mucosal inflammation	466.02	17.51	436	67015	75144	79601793

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FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

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Source	Code	Description
ATC	L01CE02	ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS ANTINEOPLASTIC AGENTS PLANT ALKALOIDS AND OTHER NATURAL PRODUCTS Topoisomerase 1 (TOP1) inhibitors
CHEBI has role	CHEBI:35610	antineoplastic agents
CHEBI has role	CHEBI:50266	Prodrugs
CHEBI has role	CHEBI:50276	topoisomerase I inhibitors
CHEBI has role	CHEBI:68495	Type I cell-death inducers
FDA EPC	N0000175609	Topoisomerase Inhibitor
FDA MoA	N0000000176	Topoisomerase Inhibitors
MeSH PA	D000970	Antineoplastic Agents
MeSH PA	D004791	Enzyme Inhibitors
MeSH PA	D059004	Topoisomerase I 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
Secondary malignant neoplasm of pancreas	indication	94459006
Metastasis from malignant tumor of colon	indication	314998002
Adenocarcinoma of pancreas	indication	700423003	DOID:4074
Astrocytoma, anaplastic	off-label use	55353007	DOID:3078
Ewing's sarcoma	off-label use	76909002	DOID:3369
Small cell carcinoma of lung	off-label use	254632001	DOID:5409
Non-small cell lung cancer	off-label use	254637007	DOID:3908
Glioblastoma multiforme of brain	off-label use	276828006	DOID:3073
Hyperbilirubinemia	contraindication	14783006	DOID:2741
Dehydration	contraindication	34095006

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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	10.46	acidic
pKa2	9.25	Basic
pKa3	2.69	Basic

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
EQ 43MG BASE/10ML (EQ 4.3MG BASE/ML)	ONIVYDE	IPSEN INC	N207793	Oct. 22, 2015	RX	INJECTABLE, LIPOSOMAL	INTRAVENOUS	8703181	May 2, 2025	TREATMENT OF PANCREATIC CANCER
EQ 43MG BASE/10ML (EQ 4.3MG BASE/ML)	ONIVYDE	IPSEN INC	N207793	Oct. 22, 2015	RX	INJECTABLE, LIPOSOMAL	INTRAVENOUS	9730891	May 2, 2025	TREATMENT OF METASTATIC ADENOCARCINOMA OF THE PANCREAS THAT HAS PROGRESSED ON GEMCITABINE-BASED THERAPY, IN COMBINATION WITH 5-FLUOROURACIL AND LEUCOVORIN
EQ 43MG BASE/10ML (EQ 4.3MG BASE/ML)	ONIVYDE	IPSEN INC	N207793	Oct. 22, 2015	RX	INJECTABLE, LIPOSOMAL	INTRAVENOUS	10980795	June 12, 2033	TREATMENT OF METASTATIC ADENOCARCINOMA OF THE PANCREAS THAT HAS PROGRESSED ON GEMCITABINE-BASED THERAPY, IN COMBINATION WITH 5-FLUOROURACIL AND LEUCOVORIN
EQ 43MG BASE/10ML (EQ 4.3MG BASE/ML)	ONIVYDE	IPSEN INC	N207793	Oct. 22, 2015	RX	INJECTABLE, LIPOSOMAL	INTRAVENOUS	11369597	June 12, 2033	TREATMENT OF METASTATIC ADENOCARCINOMA OF THE PANCREAS THAT HAS PROGRESSED ON GEMCITABINE-BASED THERAPY, IN COMBINATION WITH 5-FLUOROURACIL AND LEUCOVORIN
EQ 43MG BASE/10ML (EQ 4.3MG BASE/ML)	ONIVYDE	IPSEN INC	N207793	Oct. 22, 2015	RX	INJECTABLE, LIPOSOMAL	INTRAVENOUS	9339497	June 12, 2033	TREATMENT OF METASTATIC ADENOCARCINOMA OF THE PANCREAS THAT HAS PROGRESSED ON GEMCITABINE-BASED THERAPY, IN COMBINATION WITH 5-FLUOROURACIL AND LEUCOVORIN
EQ 43MG BASE/10ML (EQ 4.3MG BASE/ML)	ONIVYDE	IPSEN INC	N207793	Oct. 22, 2015	RX	INJECTABLE, LIPOSOMAL	INTRAVENOUS	9364473	June 12, 2033	TREATMENT OF METASTATIC ADENOCARCINOMA OF THE PANCREAS THAT HAS PROGRESSED ON GEMCITABINE-BASED THERAPY, IN COMBINATION WITH 5-FLUOROURACIL AND LEUCOVORIN, IN A PATIENT HOMOZYGOUS FOR THE UGT1A1*28 ALLELE
EQ 43MG BASE/10ML (EQ 4.3MG BASE/ML)	ONIVYDE	IPSEN INC	N207793	Oct. 22, 2015	RX	INJECTABLE, LIPOSOMAL	INTRAVENOUS	9452162	June 12, 2033	TREATMENT OF PANCREATIC CANCER THAT HAS PROGRESSED ON GEMCITABINE-BASED THERAPY, IN COMBINATION WITH 5-FLUOROURACIL AND LEUCOVORIN
EQ 43MG BASE/10ML (EQ 4.3MG BASE/ML)	ONIVYDE	IPSEN INC	N207793	Oct. 22, 2015	RX	INJECTABLE, LIPOSOMAL	INTRAVENOUS	9492442	June 12, 2033	TREATMENT OF EXOCRINE PANCREATIC CANCER THAT HAS PROGRESSED ON GEMCITABINE-BASED THERAPY, IN COMBINATION WITH 5-FLUOROURACIL AND LEUCOVORIN
EQ 43MG BASE/10ML (EQ 4.3MG BASE/ML)	ONIVYDE	IPSEN INC	N207793	Oct. 22, 2015	RX	INJECTABLE, LIPOSOMAL	INTRAVENOUS	9492442	June 12, 2033	TREATMENT OF METASTATIC ADENOCARCINOMA OF THE PANCREAS THAT HAS PROGRESSED ON GEMCITABINE-BASED THERAPY, IN COMBINATION WITH 5-FLUOROURACIL AND LEUCOVORIN
EQ 43MG BASE/10ML (EQ 4.3MG BASE/ML)	ONIVYDE	IPSEN INC	N207793	Oct. 22, 2015	RX	INJECTABLE, LIPOSOMAL	INTRAVENOUS	9492442	June 12, 2033	TREATMENT OF PANCREATIC CANCER THAT HAS PROGRESSED ON GEMCITABINE-BASED THERAPY, IN COMBINATION WITH 5-FLUOROURACIL AND LEUCOVORIN

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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 1	Enzyme	P11387	TOP1_HUMAN	INHIBITOR			DRUGBANK	CHEMBL
Muscarinic acetylcholine receptor M4	GPCR	P08173	ACM4_HUMAN		Ki	6.66	DRUG MATRIX
Canalicular multispecific organic anion transporter 1	Transporter	Q92887	MRP2_HUMAN				WOMBAT-PK
Alpha-2C adrenergic receptor	GPCR	P18825	ADA2C_HUMAN		Ki	6.34	DRUG MATRIX
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 4	Transporter	O15439	MRP4_HUMAN				WOMBAT-PK
Acetylcholinesterase	Enzyme	P22303	ACES_HUMAN		Ki	7.30	CHEMBL
Interstitial collagenase	Enzyme	P03956	MMP1_HUMAN		IC50	5.22	DRUG MATRIX
Solute carrier family 22 member 1	Transporter	O15245	S22A1_HUMAN		IC50	4.68	CHEMBL

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External reference:

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ID	Source
CP0	PDB_CHEM_ID
005262	NDDF
005263	NDDF
108783005	SNOMEDCT_US
12129	MMSL
136572-09-3	SECONDARY_CAS_RN
153329	RXNORM
236647	MMSL
372538008	SNOMEDCT_US
386912006	SNOMEDCT_US

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Pharmaceutical products:

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Product	Category	Ingredients	NDC	Form	Quantity	Route	Marketing	Label
Camptosar	HUMAN PRESCRIPTION DRUG LABEL	1	0009-7529	INJECTION, SOLUTION	20 mg	INTRAVENOUS	NDA	35 sections
Camptosar	HUMAN PRESCRIPTION DRUG LABEL	1	0009-7529	INJECTION, SOLUTION	20 mg	INTRAVENOUS	NDA	35 sections
Camptosar	HUMAN PRESCRIPTION DRUG LABEL	1	0009-7529	INJECTION, SOLUTION	20 mg	INTRAVENOUS	NDA	35 sections
Irinotecan Hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	0143-9583	INJECTION	20 mg	INTRAVENOUS	ANDA	28 sections
Irinotecan Hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	0143-9583	INJECTION	20 mg	INTRAVENOUS	ANDA	28 sections
Irinotecan Hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	0143-9701	INJECTION	20 mg	INTRAVENOUS	ANDA	28 sections
Irinotecan Hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	0143-9701	INJECTION	20 mg	INTRAVENOUS	ANDA	28 sections
Irinotecan Hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	0143-9702	INJECTION	20 mg	INTRAVENOUS	ANDA	28 sections
Irinotecan Hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	0143-9702	INJECTION	20 mg	INTRAVENOUS	ANDA	28 sections
Irinotecan hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	16714-027	INJECTION	20 mg	INTRAVENOUS	ANDA	30 sections

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