Basic information
- CAS
119413-54-6- Standard SMILES
CC[C@@]1(O)C(=O)OCc2c1cc1n(c2=O)Cc2cc3c(CN(C)C)c(O)ccc3nc2-1.Cl- InChIKey
DGHHQBMTXTWTJV-BQAIUKQQSA-N- Molecular formula
- C23H24ClN3O5
- Average molar mass
- 457.9 g/mol
- Monoisotopic mass
- 457.1404486
Names & identifiers
- Preferred name
- Topotecan Hydrochloride
- IUPAC
- (19S)-8-[(dimethylamino)methyl]-19-ethyl-7,19-dihydroxy-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)-heptaene-14,18-dione;hydrochloride
- English name
- Topotecan hydrochloride
- Molecular formula
- C23H24ClN3O5
- Molecular weight
- 457.91
Names & synonyms
Show more names
Database identifiers
- CAS
119413-54-6- PubChem CID
- 60699
- DTXSID
DTXSID1045952- ChEMBL
CHEMBL1607- ChEBI
CHEBI:232548- UNII
- 956S425ZCY
- EC Number
- 601-607-9
Properties
Computed structural properties
- Topological polar surface area
- 103 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 7
- Rotatable bonds
- 3
- Heavy atoms
- 32
- Formal charge
- 0
- Complexity
- 867
Experimental & physicochemical properties
Physicochemical properties
- Melting point
- 213 · 213-218°C
- storage temp.
- Sealed in dry,Room Temperature
- solubility
- DMSO (Slightly), Methanol (Slightly), Water (Slightly)
- form
- Light yellow to greenish powder.
- color
- White to Off-White
- Stability
- Hygroscopic
- InChIKey
- DGHHQBMTXTWTJV-UUTVKYGWNA-N
- SMILES
- C12C=C3N(CC4C=C5C(CN(C)C)=C(O)C=CC5=NC3=4)C(=O)C=1COC(=O)[C@]2(O)CC.Cl |&1:27,r|
- CAS DataBase Reference
- 119413 · 119413-54-6(CAS DataBase Reference)
- NCI Dictionary of Cancer Terms
- Hycamtin; topotecan hydrochloride
- FDA UNII
- 956 S425ZCY · 956S425ZCY
- NCI Drug Dictionary
- Hycamtin
- Symbol(GHS)
- 8 · GHS08
- Signal word
- Danger
- Hazard statements
- 351 · H351-H340-H361
- Precautionary statements
- 201 · P201-P202-P281-P308+P313-P405-P501-P201-P202-P281-P308+P313-P405-P501
- Hazard Codes
- T
- Risk Statements
- 25 · 25-36/37/38-46
- Safety Statements
- 26 · 26-36/37/39-45
- HS Code
- 29420000 · 29420000
Safety & regulation
GHS classification
GHS Classification
Danger
H300 (37.5%): Fatal if swallowed [Danger Acute toxicity, oral];H301 (12.5%): Toxic if swallowed [Danger Acute toxicity, oral];H302 (12.5%): Harmful if swallowed [Warning Acute toxicity, oral];H315 (12.5%): Causes skin irritation [Warning Skin corrosion/irritation];H319 (12.5%): Causes serious eye irritation [Warning Serious eye damage/eye irritation];H335 (12.5%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation];H340 (87.5%): May cause genetic defects [Danger Germ cell mutagenicity];H350 (50%): May cause cancer [Danger Carcinogenicity];H351 (25%): Suspected of causing cancer [Warning Carcinogenicity];H360 (37.5%): May damage fertility or the unborn child [Danger Reproductive toxicity];H360D (12.5%): May damage the unborn child [Danger Reproductive toxicity];H361 (25%): Suspected of damaging fertility or the unborn child [Warning Reproductive toxicity];H370 (25%): Causes damage to organs [Danger Specific target organ toxicity, single exposure];H412 (37.5%): Harmful to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]
P203, P260, P261, P264, P264+P265, P270, P271, P273, P280, P301+P316, P301+P317, P302+P352, P304+P340, P305+P351+P338, P308+P316, P318, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 8 reports by companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.;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. For more detailed information, please visit ECHA C&L website.
Hazard information
Hazard Classes and Categories
Acute Tox. 2 (37.5%);Acute Tox. 3 (12.5%);Acute Tox. 4 (12.5%);Skin Irrit. 2 (12.5%);Eye Irrit. 2 (12.5%);STOT SE 3 (12.5%);Muta. 1B (87.5%);Carc. 1B (50%);Carc. 2 (25%);Repr. 1B (37.5%);Repr. 2 (25%);STOT SE 1 (25%);Aquatic Chronic 3 (37.5%)
Toxicology
Drug Induced Liver Injury
Drug Induced Liver Injury Rank (DILIrank 2.0)
Topotecan hydrochloride
vNo-DILI-concern
0
No match
DOI:10.1016/j.drudis.2016.02.015
Effects During Pregnancy and Lactation
◉ Summary of Use during Lactation;Most sources consider breastfeeding to be contraindicated during maternal high-dose antineoplastic drug therapy. The manufacturer recommends that women not breastfeed during treatment with topotecan and for 1 week after the last dose. Chemotherapy may adversely affect the normal microbiome and chemical makeup of breastmilk. Women who receive chemotherapy during pregnancy are more likely to have difficulty nursing their infant.;◉ Effects in Breastfed Infants;Relevant published information was not found as of the revision date.;◉ Effects on Lactation and Breastmilk;Relevant published information was not found as of the revision date.
Safety data
- hs_code
- 29420000
- risk_code
- 25-36/37/38-46
- Signal word
- Danger
- Symbol(GHS)
- GHS08
- hazard_code
- T
- safety_code
- 26-36/37/39-45
- Hazard statements
- H351-H340-H361
- Precautionary statements
- P201-P202-P281-P308+P313-P405-P501-P201-P202-P281-P308+P313-P405-P501
Chemistry & industry
Pharmacology
FDA Pharmacological Classification
TOPOTECAN HYDROCHLORIDE
Topoisomerase Inhibitor [EPC]; Topoisomerase Inhibitors [MoA]
Applications
UsesIt is used as antineoplastic agent.
DescriptionTopotecan is a chemotherapeutic agent medication and acts as a topoisomerase inhibitor. Topotecan is asynthetic, water-soluble analog of camptothecin. It is used in the form of its hydrochloride salt to treat ovarian cancer, lung cancer and other cancer types.
UsesNaturally occurring amino acid; precursor of tetrapyrroles in the biosynthesis of chlorophyll and heme. Antineoplastic (photosensitizer)
Usesantineoplastic; topoisomerase I inhibitor
UsesA DNA topoisomerase I inhibitor; semisynthetic analog of Camptothecin. Antineoplastic. Topotecan hydrochloride is a chemotherapy agent that is a topoisomerase 1 inhibitor.
General DescriptionTopotecan is supplied in 4-mg vials and administered IV forthe treatment of ovarian cancer, cervical cancer, and smallcell lung cancer in those patients who did not respond tofirst-line therapy. Following IV administration, the drug iswidely distributed with 10% to 35% of the agent bound toplasma proteins. There is evidence that the agent may crossthe blood-brain barrier to some extent. In plasma, an equilibriumis established between the lactone and the less activehydroxy acid with 20% of the drug present as the lactone 1hour after the infusion is complete. In contrast to irinotecan,both the lactone and the hydroxy acid bind equally well tohuman serum albumin. N-Demethylation of the tertiaryamine to give the secondary amine is mediated by CYP3A4and represents a minor route of metabolism. Glucuronidationof the parent and the phase I metabolites also occurs to a limited(10%) extent.Elimination occurs primarily in theurine, with 30% of the dose being recovered as unchangeddrug. The terminal elimination half-life is 2 to 3 hours. Themajor toxicity seen for topotecan is dose-limiting myelosuppression.Nausea and vomiting are seen in most (70%–80%)patients, along with diarrhea and abdominal pain. Other toxicitiesinclude headache myalgias, alopecia and elevation ofserum transaminases, alkaline phosphatases, and bilirubin.Microscopic hematuria (blood in the urine) may also be seen.
Upstream & downstream products
Upstream raw materials
Suppliers100 total
Related reactions
Compound notes
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