MITOTOX

Drug

D1374 | Irinotecan

Properties

Molecular Formula	C33H38N4O6
Molecular Weight	586.7
Structure
State	solid
Clearance	* 13.3 L/h/m^2 [Dose of 125 mg/m^2, patients with solid tumours] * 13.9 L/h/m^2 [Dose of 340 mg/m^2, patients with solid tumours]
Volume of distribution	The volume of distribution of terminal elimination phase is 110 L/m^2 when a dose of 125 mg/m^2 is given to patients with solid tumours. The volume of distribution of terminal elimination phase is 234 L/m^2 when a dose of 340 mg/m^2 is given to patients with solid tumours.
Route of elimination	The cumulative biliary and urinary excretion of irinotecan and its metabolites (SN-38 and SN-38 glucuronide) over a period of 48 hours following administration of irinotecan in two patients ranged from approximately 25% (100 mg/m2) to 50% (300 mg/m2).
Protein binding	30%-68% protein bound, mainly to albumin.
Half life	The half life of irinotecan is about 6 - 12 hours. The terminal elimination half-life of the active metabolite, SN-38 is 10 - 20 hours.
Absorption	The maximum plasma concentration (Cmax) when a dose of 125 mg/m^2 is given to patients with solid tumours is 1660 ng/mL. The AUC (0-24) is 10,200 ng·h/mL. The Cmax when a dose of 340 mg/m^2 is given to patients with solid tumours is 3392 ng/mL. The AUC (0-24) is 20,604 ng·h/mL.
Trade names	Camptosar, Campto, Onivyde
Description	antineoplastic enzyme inhibitor; derivative of camptothecin; inhibits the action of topoisomerase I (prevents religation of the DNA strand by binding to topoisomerase I-DNA complex, and causes double-strand DNA breakage and cell death)

Therapeutic Classification Source: DrugBank

L01XX19 Irinotecan

[L01XX] Other antineoplastic agents

[L01X] OTHER ANTINEOPLASTIC AGENTS

[L01] ANTINEOPLASTIC AGENTS

[L] Antineoplastic and immunomodulating agents

Mitochondrial Toxicity Evaulation

Toxicity	Dose	Time	Species	Model	Method	Action	Positive criterion	Reference
MITOCHONDRIAL FATTY ACID BETA OXIDATION	6μM	10	mice	Lean mice vs Ob/ob mice	Measurement of oxygen consumption in the presence of ADP (state 3) and the different substrates was carried out on the Mitologics screening platform		EC20	227

GHS Hazard Tables Source: PubChem

Pictogram	Signal	Statements	Precautionary Statement Codes
	Danger	Aggregated GHS information provided by 9 companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral] H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation] H318 (100%): Causes serious eye damage [Danger Serious eye damage/eye irritation] H361 (100%): Suspected of damaging fertility or the unborn child [Warning Reproductive toxicity] H373 (100%): Causes damage to organs through prolonged or repeated exposure [Warning Specific target organ toxicity, repeated exposure] Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.	P201, P202, P260, P264, P270, P280, P281, P301+P312, P302+P352, P305+P351+P338, P308+P313, P310, P314, P321, P330, P332+P313, P362, P405, and P501; (The corresponding statement to each P-code can be found at the GHS Classification page.)

Pictogram

Signal

Statements

Precautionary Statement Codes

Danger

Aggregated GHS information provided by 9 companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]

H318 (100%): Causes serious eye damage [Danger Serious eye damage/eye irritation]

H361 (100%): Suspected of damaging fertility or the unborn child [Warning Reproductive toxicity]

H373 (100%): Causes damage to organs through prolonged or repeated exposure [Warning Specific target organ toxicity, repeated exposure]

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

P201, P202, P260, P264, P270, P280, P281, P301+P312, P302+P352, P305+P351+P338, P308+P313, P310, P314, P321, P330, P332+P313, P362, P405, and P501; (The corresponding statement to each P-code can be found at the GHS Classification page.)

Indications Source: SIDER

Synonyms Source: PubChem

(+)-Irinotecan	(1,4'-Bipiperidine)-1'-carboxylic acid, 4,11-diethyl-3,4,12-14-tetrahydro-4-hydroxy-3,14-dioxo-1H-pyrano(3',4':6,7)indolizino(1,2-b)quinolin-9-yl ester, (S)-	(19S)-10,19-diethyl-19-hydroxy-14,18-dioxo-17-oxa-3,13-diazapentacyclo[11.8.0.0^{2,11}.0^{4,9}.0^{15,20}]henicosa-1(21),2(11),3,5,7,9,15(20)-heptaen-7-yl 4-(piperidin-1-yl)piperidine-1-carboxylate
(4S)-4,11-DIETHYL-4-HYDROXY-3,14-DIOXO-3,4,12,14-TETRAHYDRO-1H-PYRANO[3'',4'':6,7]INDOLIZINO[1,2-B]QUINOLIN-9-YL 1,4''-BIPIPERIDINE-1''-CARBOXYLATE	(4S)-4,11-DIETHYL-4-HYDROXY-3,14-DIOXO-3,4,12,14-TETRAHYDRO-1H-PYRANO[3',4':6,7]INDOLIZINO[1,2-B]QUINOLIN-9-YL 1,4'-BIPIPERIDINE-1'-CARBOXYLATE	(4S)-4,11-Diethyl-3,4,12,14-tetrahydro-4-hydroxy-3,14-dioxo-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinolin-9-yl [1,4'-bipiperidine]-1'-carboxylic acid ester hydrochloride
(4S)-4,11-Diethyl-4-hydroxy-3,14-dioxo-4,12-dihydro-1H-pyrano[3,4-f]quinolino[2,3-a]indolizin-9-yl 4-piperidylpiperidinecarboxylate	(4S)-4,11-diethyl-4-hydroxy-3,14-dioxo-3,4,12,14-tetrahydro-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinolin-9-yl [1,4'-bipiperidine]-1'-carboxylate	(S)-4,11-diethyl-4-hydroxy-3,14-dioxo-3,4,12,14-tetrahydro-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinolin-9-yl [1,4'-bipiperidine]-1'-carboxylate
(diethyl-hydroxy-dioxo-[?]yl) 4-(1-piperidyl)piperidine-1-carboxylate	1,4'-Bipiperidine-1'-carboxylic acid (S)-4,11-diethyl-3,4,12,14- tetrahydro-4-hydroxy-3,14-dioxo-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinolin-9-yl ester	1,4'-bipiperidine-1'-carboxylic acid (s)-4,11-diethyl-3,4,12,14- tetrahydro-4-hydroxy-3,14-dioxo-1h-pyrano(3',4':6,7)indolizino(1,2-b)quinolin-9-yl ester
1u65	682I445	97682-44-5
AB0014364	AB00698464-07	AB00698464-09
AB00698464-10	AB00698464-11	AB00698464_12
AB00698464_13	AB00698464_14	AB07527
AC-7469	AK163712	AKOS015894969
ANW-41679	AS-14323	BCP02860
BCP9000793	BDBM50128267	BRD-K08547377-003-02-4
BSPBio_002346	Biotecan	Biotecan (TN)
C16641	C33H38N4O6	CHEBI:80630
CHEMBL481	CPT-11	CPT-11
CPT-11 hydrochloride;Camptothecin 11 hydrochloride	CS-1138	CTK8B3046
Camptosar	D08086	DB00762
DTXSID1041051	EBD36403	GTPL6823
HSDB 7607	HY-16562	IRINOTECAN
Irinophore C	Irinotecan (INN)	Irinotecan [INN:BAN]
Irinotecan lactone	Irinotecan mylan	Irinotecan;Irinotecan hydrochloride;(+)-7-Ethyl-10-[4-(1-piperidino)-1-piperidino]-carbonyloxycamptothecin, monohydrochloride, trihydrate;[1,4-Bipiperidine]-1-carboxylic acid, (4S)-4,11-diethyl-3,4,12,14-tetrahydro-4-hydroxy-3,14-dioxo-1H-pyrano[3,4:6,7]indolizino[1,2-b]quinolin-9-yl ester, hydrochloride, hydrate (1:1:3);IRINOTECAN;irrinotecan
Irinotecanum	Irinotecanum [INN-Latin]	Irrinotecan
K754	KS-00000NVX	LS-44589
MCULE-1702653278	NCGC00178697-02	NCGC00178697-05
NCI60_005051	NSC-728073	NSC728073
Onivyde	PubChem13094	PubChem16441
Q412197	SC-17271	SCHEMBL4034
UNII-7673326042	W-5141	ZINC1612996
[1,4'']Bipiperidinyl-1''-carboxylic acid 4,11-diethyl-4-hydroxy-3,13-dioxo-3,4,12,13-tetrahydro-1H-2-oxa-6,12a-diaza-dibenzo[b,h]fluoren-9-yl ester	[1,4'']bipiperidinyl-1''-carboxylic acid (S)-4,11-diethyl-4-hydroxy-3,13-dioxo-3,4,12,13-tetrahydro-1H-2-oxa-6,12a-diaza-dibenzo[b,h]fluoren-9-yl ester	irinotecan
s1198

External IDs

DrugBank	DB00762
CAS Number	100286-90-6, 97682-44-5
PubChem Compound	60838