Topotecan

HCID 60700CAS 119413-54-6

Basic information

Standard SMILES
CC[C@@]1(O)C(=O)OCc2c1cc1n(c2=O)Cc2cc3c(CN(C)C)c(O)ccc3nc2-1
InChIKey
UCFGDBYHRUNTLO-QHCPKHFHSA-N
Molecular formula
C23H23N3O5
Average molar mass
421.4 g/mol
Monoisotopic mass
421.16377084

Overview

Topotecan is a pyranoindolizinoquinoline used as an antineoplastic agent. It is a derivative of camptothecin and works by binding to the topoisomerase I-DNA complex and preventing religation of these 328 single strand breaks. It has a role as an antineoplastic agent and an EC 5.99.1.2 (DNA topoisomerase) inhibitor.

Names & identifiers

Preferred name
Topotecan
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
English name
Topotecan hydrochloride
Molecular formula
C23H24ClN3O5
Molecular weight
457.91

Names & synonyms

topotecan123948-87-8HycamptamineTopotecan lactoneNogitecanHycamptinTopotecane(S)-TopotecanTopotecanumTopophore CTopoCEDSKF-104864-A
Show more names
HYDROCHLORIDE3-[1-methyl-6-(4-piperidyl)indazol-3-yl]piperidine-2,6-dioneHycamtinTOPOTECAN HCL3-amino-1,3-dimethyl-cyclobutanol2-(3-Chloro-5-trifluoromethyl-pyridin-2-yl)-ethylamine(1R)-6,7-dimethoxy-1-[(4-methoxyphenyl)methyl]-1,2,3,4-tetrahydroisoquinoline108563NSC 609669SKF-104864A
9-Dimethylaminomethyl-10-hydroxycamptothecinNSC-641007SKF-1048647M7YKX2N15FF-10850 (liposomal topotecan)NSC609699NSC-609699SK&F 104864 A

Database identifiers

CAS
119413-54-6、123948-87-8
PubChem CID
60700
DTXSID
DTXSID3042685
ChEMBL
CHEMBL84
ChEBI
CHEBI:63632
UNII
7M7YKX2N15
EC Number
687-471-1
Nikkaji
J2.256.757H、J362.027A

Properties

Computed structural properties

XLogP
0.5
Topological polar surface area
103 Ų
Hydrogen bond donors
2
Hydrogen bond acceptors
7
Rotatable bonds
3
Heavy atoms
31

Experimental & physicochemical properties

DrugsPharmaceuticals -> Listed in ZINC15
LogP · 2 items

0.8

0.91

Solubility8.61e-01 g/L
Human Drugs · 4 items

Breast Feeding; Lactation; Antineoplastic Agents; Topoisomerase I Inhibitors

EMA approved medicines: Human medicine

EMA approved medicines: Human medicine

EMA approved medicines: Human medicine

DecompositionHazardous decomposition products: Hazardous decomposition products formed under fire conditions. - Carbon oxides, nitrogen oxides (NOx), hydrogen chloride gas.
Melting Point · 2 items

213-218 °C

213 - 218 °C

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

Safety & regulation

GHS classification

GHS Classification · 6 items

Danger

H301 (18.8%): Toxic if swallowed [Danger Acute toxicity, oral]

P203, P261, P264, P264+P265, P270, P271, P280, P301+P316, P302+P352, P304+P340, P305+P351+P338, 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 48 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Warning

H341: Suspected of causing genetic defects [Warning Germ cell mutagenicity]

Hazard information

FDA Requirements · 1 item

The Approved Drug Products with Therapeutic Equivalence Evaluations identifies currently marketed prescription drug products, including topotecan hydrochloride, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act. /Topotecan hydrochloride/

Hazard Classes and CategoriesAcute Tox. 3 (18.8%)
Hazardous Reactivities and IncompatibilitiesIncompatible materials: Strong oxidizing agents.

Safety & protection

Fire Fighting Procedures · 2 items

Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.

Advice for firefighters: Wear self contained breathing apparatus for fire fighting if necessary.

Storage Conditions · 2 items

Store the vials protected from light in the original cartons at controlled room temperature between 20 deg and 25 °C (68 deg and 77 °F).

Conditions for safe storage, including any incompatibilities: Keep container tightly closed in a dry and well-ventilated place. Recommended storage temperature: -20 °C.

Cleanup Methods · 1 item

Accidental Release Measures. Personal precautions, protective equipment and emergency procedures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. Environmental precautions: Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Methods and materials for containment and cleaning up: Pick up and arrange disposal without creating dust. Sweep up and shovel. Keep in suitable, closed containers for disposal.

Disposal Methods · 2 items

SRP: Expired or waste pharmaceuticals shall carefully take into consideration applicable DEA, EPA, and FDA regulations. It is not appropriate to dispose by flushing the pharmaceutical down the toilet or discarding to trash. If possible return the pharmaceutical to the manufacturer for proper disposal being careful to properly label and securely package the material. Alternatively, the waste pharmaceutical shall be labeled, securely packaged and transported by a state licensed medical waste contractor to dispose by burial in a licensed hazardous or toxic waste landfill or incinerator.

Waste treatment methods. Product: Offer surplus and non-recyclable solutions to a licensed disposal company. Contact a licensed professional waste disposal service to dispose of this material. Dissolve or mix the material with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber. Contaminated packaging: Dispose of as unused product.

Preventive Measures · 4 items

Precautions for safe handling: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Provide appropriate exhaust ventilation at places where dust is formed.

Appropriate engineering controls: Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday.

Gloves must be inspected prior to use. Use proper glove removal technique (without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands.

SRP: Local exhaust ventilation should be applied wherever there is an incidence of point source emissions or dispersion of regulated contaminants in the work area. Ventilation control of the contaminant as close to its point of generation is both the most economical and safest method to minimize personnel exposure to airborne contaminants. Ensure that the local ventilation moves the contaminant away from the worker.

Personal Protective Equipment (PPE) · 4 items

Eye/face protection: Safety glasses with side-shields conforming to EN166 Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU).

Skin protection: Handle with gloves.

Body Protection: Impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace.

Respiratory protection: Where risk assessment shows air-purifying respirators are appropriate use a full-face particle respirator type N100 (US) or type P3 (EN 143) respirator cartridges as a backup to engineering controls. If the respirator is the sole means of protection, use a full-face supplied air respirator. Use respirators and components tested and approved under appropriate government standards such as NIOSH (US) or CEN (EU).

Toxicology

Interactions · 4 items

Topotecan is a substrate of the efflux transporters P-glycoprotein (Pgp, ABCB1) and ABCG2 (breast cancer resistance protein (BRCP)). Concomitant use of elacridar (not commercially available in the US), an inhibitor of both P-glycoprotein and ABCG2 transporters, with oral topotecan resulted in a 2.5-fold increase in the area under the plasma concentration-time curve (AUC) for both topotecan lactone, the pharmcologically active form of the drug, and total topotecan. Concomitant use of oral topotecan with inhibitors of P-glycoprotein (e.g., cyclosporine, ketoconazole, ritonavir, saquinavir) also resulted in substantial increases in topotecan exposure. In one study, concomitant use of cyclosporine administered within 4 hours of an oral dose of topotecan resulted in a 2- to 3-fold increase in the AUCs of both topotecan lactone and total topotecan. The manufacturer states that concomitant use of oral topotecan with Pgp inhibitors should be avoided. If topotecan is used concomitantly with a Pgp (ABCB1) and/or an ABCG2 inhibitor, careful monitoring for signs of toxicity should be performed.

Topotecan (TpT) is a major inhibitory compound of topoisomerase (topo) I that plays important roles in gene transcription and cell division. We have previously reported that heparin and heparan sulfate (HS) might be transported to the cell nucleus and they can interact with topoisomerase I. We hypothesized that heparin and HS might interfere with the action of TpT. To test this hypothesis we isolated topoisomerase I containing cell nuclear protein fractions from normal liver, liver cancer tissues, and hepatoma cell lines. The enzymatic activity of these extracts was measured in the presence of heparin, liver HS, and liver cancer HS. In addition, topo I activity, cell viability, and apoptosis of HepG2 and Hep3B cells were investigated after heparin and TpT treatments. Liver cancer HS inhibited topo I activity in vitro. Heparin treatment abrogated topo I enzyme activity in Hep3B cells, but not in HepG2 cells, where the basal activity was higher. Heparin protected the two hepatoma cell lines from TpT actions and decreased the rate of TpT induced S phase block and cell death. These results suggest that heparin and HS might interfere with the function of TpT in liver and liver cancer.

The severity of drug-induced myelosuppression may be increased when IV topotecan is used in combination with other cytotoxic agents, and dosage reduction may be necessary. Severe myelotoxicity, in some cases resulting in fatalities from sepsis, has occurred during combined therapy with IV topotecan and other antineoplastic agents (e.g., cisplatin, paclitaxel). A sequence-dependent interaction has been reported when IV topotecan is administered concomitantly with cisplatin; lower doses of each drug were required with administration of cisplatin on day 1 of the topotecan dosing schedule compared with administration of cisplatin on day 5 of the topotecan dosing schedule.

Concurrent administration of granulocyte colony-stimulating factor (G-CSF) can prolong the duration of neutropenia associated with IV topotecan therapy. If G-CSF (filgrastim) is to be used concomitantly, therapy should be initiated 24 hours after the final dose of IV topotecan (i.e., beginning on day 6 of the 21-day treatment course for monotherapy or beginning on day 4 of the 21-day treatment course for combination therapy with IV topotecan and cisplatin).

Milk Concentrations · 1 item

EXPERIMENTAL: In lactating rats receiving IV topotecan at a dosage of 4.72 mg/sq m, high concentrations of the drug (i.e., up to 48 times higher than plasma concentrations) were distributed into milk. It is not known whether topotecan is distributed into human milk.

Toxicity Summary · 1 item

IDENTIFICATION AND USE: Topotecan is antineoplastic medication acting as topoisomerase I inhibitor. HUMAN EXPOSURE AND TOXICITY: The dose-limiting toxicity of topotecan is leukopenia. Topotecan-induced neutropenia can cause neutropenic colitis. Fatalities due to neutropenic colitis have been reported in clinical trials with topotecan. Overdoses (up to 10-fold of the prescribed dose) occurred in patients treated with intravenous topotecan. The primary complication of overdosage is bone marrow suppression. Interstitial lung disease (sometimes fatal) has been reported during postmarketing experience with IV topotecan. Risk factors for developing interstitial lung disease include pulmonary fibrosis, lung cancer, exposure to thoracic radiation, use of drugs known to cause pulmonary toxicity, use of colony-stimulating factors (i.e., hematopoietic growth factors), and a history of interstitial lung disease. Patients should be monitored for symptoms suggestive of interstitial lung disease, including cough, fever, dyspnea, and/or hypoxia. Case report describes a patient with pre-existing pulmonary fibrosis and progressive extensive stage small cell lung cancer. After receiving a single intravenous dose of topotecan, the patient developed sub-acute respiratory failure, and died 15 days later with pathology findings of organizing, reparative phase, diffuse alveolar damage. Topotecan was clastogenic to cultured human lymphocytes with and without metabolic activation. ANIMAL STUDIES: Single dose toxicity was investigated in rodents and dogs following intravenous administration of topotecan. Doses of 56, 148 or 74 mg/ sq m were lethal in mice, rats or dogs respectively. Target organs of toxicity were bone marrow, lymphoid tissues, gastrointestinal tract and ovaries. In repeat dose experiments at or below the maximum tolerated dose, the toxicity profile was characterized by myelotoxicity (neutropenia, thrombocytopenia, lymphopenia and anemia), lymphoid depletion and gastrointestinal effects. Furthermore, other tissues with a rapid cell turnover, such as hair follicles and testis were affected. The main dose-limiting toxicity was the effect on bone marrow. In surviving animals, effects were reversible after termination of treatment. In mice, a single treatment with a cytotoxic agent causes cognitive impairment. Studies in dogs given about 1/4th the clinical dose of the drug daily for a month suggest that treatment may cause an increase in the incidence of multinucleated spermatogonial giant cells in the testes. Topotecan given to female rats prior to mating at a dose equal to the clinical dose caused superovulation possibly related to inhibition of follicular atresia. This dose given to pregnant female rats also caused increased pre-implantation loss. Topotecan was mutagenic to L5178Y mouse lymphoma cells with and without metabolic activation. It was also clastogenic to mouse bone marrow. Topotecan did not cause mutations in bacterial cells. Topotecan is also a germ cell mutagen and its effect is more pronounced during the post-meiotic stages through a mechanism that may involve increases in DNA oxidative stress.

Natural Pollution SourcesTopotecan is manufactured from Camptothecin, a natural plant substance found in Camptothecin acuminata (Family: Nyssaceae) and Nothapodytes nimmoniana (Synonym: Mappia foetida, Family: Icacinaceae)(1,2).
Human Toxicity Excerpts · 5 items

/SIGNS AND SYMPTOMS/ Topotecan-induced neutropenia can cause neutropenic colitis (cecitis or typhlitis). Fatalities due to neutropenic colitis have been reported in clinical trials with topotecan. In patients presenting with fever, neutropenia, and a compatible pattern of abdominal pain, the possibility of neutropenic colitis should be considered.

/SIGNS AND SYMPTOMS/ Overdoses (up to 10-fold of the prescribed dose) occurred in patients treated with intravenous topotecan. The primary complication of overdosage is bone marrow suppression. The observed signs and symptoms of overdose are consistent with the known adverse reactions associated with Hycamtin for intravenous use. In addition, elevated hepatic enzymes and mucositis have been reported following overdose.

/SIGNS AND SYMPTOMS/ Interstitial lung disease (sometimes fatal) has been reported during postmarketing experience with IV topotecan. Risk factors for developing interstitial lung disease include pulmonary fibrosis, lung cancer, exposure to thoracic radiation, use of drugs known to cause pulmonary toxicity, use of colony-stimulating factors (i.e., hematopoietic growth factors), and a history of interstitial lung disease. Patients should be monitored for symptoms suggestive of interstitial lung disease, including cough, fever, dyspnea, and/or hypoxia. If a new diagnosis of interstitial lung disease is confirmed, the manufacturer states that topotecan therapy should be discontinued.

/CASE REPORTS/ Drug-induced pulmonary toxicities of anticancer agents have been well described, but the pathophysiology of agents typically used in advanced disease has not been well studied. Symptoms of pulmonary drug toxicity in advanced lung cancer patients may frequently be attributed to disease progression, pulmonary embolism, or infection. In patients with pre-existing interstitial pulmonary fibrosis even less is known. This report describes an unfortunate patient with pre-existing pulmonary fibrosis and progressive extensive stage small cell lung cancer. After receiving a single intravenous dose of topotecan, the patient developed sub-acute respiratory failure, and died 15 days later with pathology findings of organizing, reparative phase, diffuse alveolar damage. To our knowledge this is the first pathology confirmation of diffuse alveolar damage in a patient developing dyspnea following topotecan therapy. The frequency with which camptothecin-related dyspnea is associated with diffuse alveolar damage might be underestimated and is of special concern in patients with limited pulmonary reserve.

For more Human Toxicity Excerpts (Complete) data for Topotecan (6 total), please visit the HSDB record page.

Drug Induced Liver Injury · 5 items

Drug-Induced Liver Injury Severity and Toxicity (DILIst)

topotecan

DILI Negative

Oral

DOI:10.1016/j.drudis.2019.09.022

Regulatory information

FDA Requirements · 1 item

The Approved Drug Products with Therapeutic Equivalence Evaluations identifies currently marketed prescription drug products, including topotecan hydrochloride, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act. /Topotecan hydrochloride/

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

Chemistry & industry

Pharmacology

ATC Code · 3 items

L01XX17

L - Antineoplastic and immunomodulating agents

QL - Antineoplastic and immunomodulating agents

Protein Binding35%
Pharmacodynamics · 1 item

Topotecan, a semi-synthetic derivative of camptothecin (a plant alkaloid obtained from the <i>Camptotheca acuminata</i> tree), is an anti-tumor drug with topoisomerase I-inhibitory activity similar to irinotecan. DNA topoisomerases are enzymes in the cell nucleus that regulate DNA topology (3-dimensional conformation) and facilitate nuclear processes such as DNA replication, recombination, and repair. During these processes, DNA topoisomerase I creates reversible single-stranded breaks in double-stranded DNA, allowing intact single DNA strands to pass through the break and relieve the topologic constraints inherent in supercoiled DNA. The 3'-DNA terminus of the broken DNA strand binds covalently with the topoisomerase enzyme to form a catalytic intermediate called a cleavable complex. After DNA is sufficiently relaxed and the strand passage reaction is complete, DNA topoisomerase reattaches the broken DNA strands to form the unaltered topoisomers that allow transcription to proceed. Topotecan interferes with the growth of cancer cells, which are eventually destroyed. Since the growth of normal cells can be affected by the medicine, other effects may also occur. Unlike irinotecan, topotecan is found predominantly in the inactive carboxylate form at neutral pH and it is not a prodrug.

Mechanism of Action · 2 items

Topotecan has the same mechanism of action as irinotecan and is believed to exert its cytotoxic effects during the S-phase of DNA synthesis. Topoisomerase I relieves torsional strain in DNA by inducing reversible single strand breaks. Topotecan binds to the topoisomerase I-DNA complex and prevents religation of these single strand breaks. This ternary complex interferes with the moving replication fork, which leads to the induction of replication arrest and lethal double-stranded breaks in DNA. As mammalian cells cannot efficiently repair these double strand breaks, the formation of this ternary complex eventually leads to apoptosis (programmed cell death). Topotecan mimics a DNA base pair and binds at the site of DNA cleavage by intercalating between the upstream (−1) and downstream (+1) base pairs. Intercalation displaces the downstream DNA, thus preventing religation of the cleaved strand. By specifically binding to the enzyme–substrate complex, Topotecan acts as an uncompetitive inhibitor.

Topoisomerase I relieves torsional strain in DNA by inducing reversible single-strand breaks. Topotecan binds to the topoisomerase I-DNA complex and prevents religation of these single-strand breaks. The cytotoxicity of topotecan is thought to be due to double-strand DNA damage produced during DNA synthesis, when replication enzymes interact with the ternary complex formed by topotecan, topoisomerase I, and DNA. Mammalian cells cannot efficiently repair these double strand breaks.

Biological Half-Life · 4 items

2-3 hours

The pharmacokinetics of topotecan have been evaluated in cancer patients following doses of 0.5 to 1.5 mg/sq m administered as a 30-minute infusion. Topotecan exhibits multiexponential pharmacokinetics with a terminal half-life of 2 to 3 hours.

Topotecan has a terminal half-life of 3-6 hours following oral administration and 2-3 hours following IV administration of the drug.

... The objective of this study was to characterize the disposition of topotecan in a patient with severe renal insufficiency receiving hemodialysis. ... The topotecan terminal half-life off dialysis was 13.6 hr, compared with an apparent half-life determined during hemodialysis of 3.0 hr. ...

Metabolism/Metabolites · 2 items

Topotecan undergoes a reversible pH dependent hydrolysis of its lactone moiety; it is the lactone form that is pharmacologically active.

Topotecan undergoes a reversible pH-dependent hydrolysis of its lactone moiety; it is the lactone form that is pharmacologically active. At pH =4, the lactone is exclusively present, whereas the ring-opened hydroxy-acid form predominates at physiologic pH. In vitro studies in human liver microsomes indicate topotecan is metabolized to an N-demethylated metabolite. The mean metabolite:parent AUC ratio was about 3% for total topotecan and topotecan lactone following IV administration.

Uses & manufacturing

Uses · 4 items

MEDICATION

THERAPEUTIC CATEGORY: Antineoplastic

Topoisomerase I Inhibitors

Consumption (g per capita) in the USA (2002): 7.59e-07

Methods of Manufacturing · 2 items

Topotecan is semisynthetically manufactured from the plant-derived alkaloid camptothecin. The starting material may be obtained from two natural sources - Chinese (Acuminata) and Indian (Mappia). Purification of the crude extract from either source is required. The main steps in the synthesis involve reduction and selective oxidation of the quinoline moiety of camptothecin, followed by the introduction of an N,N-dimethylaminomethyl side-chain.

Preparation: J. C. Boehm et al., European Patent Office patent 321122,; eidem, United States of America patent 5004758 (1989, 1991 both to SmithKline Beecham).

Formulations/PreparationsTable: Topotacan Hydrochloride Preparations [Table#8197]
Applications · 6 items

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.

Suppliers50 total

北京华美互利生物化工010-56205725 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
南部县诚信科技有限公司0838-5675166 15883665058 · [email protected]
大连美仑生物技术有限公司0411-62910999 13889544652 · [email protected]
安耐吉化学&3A(安徽泽升科技股份有限公司)400-0056266 · [email protected]

Related reactions

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