Camptosar

HCID 60837
NotesReactions
Substructure searchFind similar structures

Basic information

CAS
136572-09-3
Standard SMILES
CCc1c2c(nc3ccc(OC(=O)N4CCC(N5CCCCC5)CC4)cc13)-c1cc3c(c(=O)n1C2)COC(=O)[C@]3(O)CC.Cl.O.O.O
InChIKey
KLEAIHJJLUAXIQ-JDRGBKBRSA-N
Molecular formula
C33H45ClN4O9
Average molar mass
677.2 g/mol
Monoisotopic mass
676.2875067

Overview

Irinotecan hydrochloride hydrate is a hydrate that is the trihydrate form of irinotecan hydrochloride. Onivyde is used in combination with fluorouracil and leucovorin, for the treatment of patients with metastatic adenocarcinoma of the pancreas after disease progression following gemcitabine-based therapy. It is converted via hydrolysis of the carbamate linkage to its active metabolite, SN-38, which is ~1000 times more active. It has a role as an antineoplastic agent, a prodrug, an EC 5.99.1.2 (DNA topoisomerase) inhibitor and an apoptosis inducer. It contains an irinotecan hydrochloride (anhydrous).

Names & identifiers

Preferred name
Camptosar
IUPAC
[(19S)-10,19-diethyl-19-hydroxy-14,18-dioxo-17-oxa-3,13-diazapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-1(21),2,4(9),5,7,10,15(20)-heptaen-7-yl] 4-piperidin-1-ylpiperidine-1-carboxylate;trihydrate;hydrochloride
English name
Irinotecan hydrochloride trihydrate
Molecular formula
C33H45ClN4O9
Molecular weight
677.18

Names & synonyms

CamptosarIrinotecan hydrochloride hydrateCHEBI:90881RefChem:148744(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 monohydrochloride trihydrateIRINOTECAN HYDROCHLORIDE Trihydrate136572-09-3Irinotecan Hcl TrihydrateCPT-11 TrihydrateMFCD01765731Irinotecan (hydrochloride trihydrate)(+)-7-Ethyl-10-hydroxycamptothecine 10-(1,4'-bipiperidine)-1'-carboxylate, monohydrochloride, trihydrate
Show more names
Iriontecan HCLIrinotecan HCL 3H2OIrinotecan HydrochLIrinotecan TrihydrateCPT-11 HCl TrihydrateIrinotecan HydrochloridIRINOTECON HCL TRIHYDRATEVincristine-d 3 -1 sulfate
IRINOTECAN HYDROCHLORIDE [ORANGE BOOK](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 hydrochloride trihydrate[(19S)-10,19-diethyl-19-hydroxy-14,18-dioxo-17-oxa-3,13-diazapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-1(21),2,4(9),5,7,10,15(20)-heptaen-7-yl] 4-piperidin-1-ylpiperidine-1-carboxylate;trihydrate;hydrochlorideIrinotecan HCI TrihydrateUNII-042LAQ1IISCamptosar (TN)[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 monohydrochloride trihydrate; Irinotecan hydrochloride hydrate; Irinotecan hydrochloride trihydrateOnivyde (TN)

Database identifiers

CAS
136572-09-3
PubChem CID
60837
DTXSID
DTXSID60929485
ChEMBL
CHEMBL1200512
ChEBI
CHEBI:90881
UNII
042LAQ1IIS

Properties

Computed structural properties

Topological polar surface area
116 Ų
Hydrogen bond donors
5
Hydrogen bond acceptors
11
Rotatable bonds
5
Heavy atoms
47

Experimental & physicochemical properties

Human Drugs · 2 items

Breast Feeding; Lactation; Milk, Human; Antineoplastic Agents; Enzyme Inhibitors; Topoisomerase I Inhibitors

EMA approved medicines: Human medicine (Orphan designations)

Physicochemical properties

Melting point
250 · 250-256°C (dec.)
Boiling point
257 °C · 257°C(lit.)
storage temp.
2 · 2-8°C
solubility
Soluble in DMSO (up to 50 mg/ml), in Water (up to 4 mg/ml) or in Ethanol (up to 4 mg/ml).
form
White solid.
color
Yellow

Safety & regulation

Toxicology

Effects During Pregnancy and Lactation◉ Summary of Use during Lactation

Safety data

wgk
WGK 3
rtecs
DW1060750
hs_code
29349990
Toxicity
dog,LD50,intravenous,40mg/kg (40mg/kg),Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 26, Pg. 953, 1995.
risk_code
22
Signal word
Danger

Chemistry & industry

Pharmacology

MeSH Pharmacological ClassificationCompounds that inhibit the activity of DNA TOPOISOMERASE I.
Applications · 2 items

DescriptionIrinotecan (136572-09-3) is a semi-synthetic derivative of camptothecin (Cat.# 10-1041) that is an FDA approved anticancer drug. It is a prodrug that is converted by tissue esterases to 7-ethyl-10-hydroxycamptothecin (SN-38, Cat.# 10-2425), a potent inhibitor of DNA topoisomerase I.1,2 Although irinotecan is also a topoisomerase inhibitor, SN-38 is approximately 1000 times as potent in purified enzyme studies. In vitro cytotoxicity assays show much greater variability in potency between the two (2-2000 fold).3

UsesIrinotecan Hydrochloride Trihydrate is a DNA topoisomerase inhibitor.

Upstream & downstream products

Suppliers100 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
北京华美互利生物化工010-56205725 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
南京云志欣合生物科技有限公司18115209001 · [email protected]
Additional notes · 1 item

DefinitionChEBI: A hydrate that is the trihydrate form of irinotecan hydrochloride. Onivyde is used in combination with fluorouracil and leucovorin, for the treatment of patients with metastatic adenocarcinoma of the pancreas after disease progression following gemcitabine based therapy. It is converted via hydrolysis of the carbamate linkage to its active metabolite, SN-38, which is ~1000 times more active.

Related reactions

6 records
New reaction record

Compound notes

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