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EC number: 205-275-2 | CAS number: 137-05-3
- Life Cycle description
- Uses advised against
- Endpoint summary
- Appearance / physical state / colour
- Melting point / freezing point
- Boiling point
- Density
- Particle size distribution (Granulometry)
- Vapour pressure
- Partition coefficient
- Water solubility
- Solubility in organic solvents / fat solubility
- Surface tension
- Flash point
- Auto flammability
- Flammability
- Explosiveness
- Oxidising properties
- Oxidation reduction potential
- Stability in organic solvents and identity of relevant degradation products
- Storage stability and reactivity towards container material
- Stability: thermal, sunlight, metals
- pH
- Dissociation constant
- Viscosity
- Additional physico-chemical information
- Additional physico-chemical properties of nanomaterials
- Nanomaterial agglomeration / aggregation
- Nanomaterial crystalline phase
- Nanomaterial crystallite and grain size
- Nanomaterial aspect ratio / shape
- Nanomaterial specific surface area
- Nanomaterial Zeta potential
- Nanomaterial surface chemistry
- Nanomaterial dustiness
- Nanomaterial porosity
- Nanomaterial pour density
- Nanomaterial photocatalytic activity
- Nanomaterial radical formation potential
- Nanomaterial catalytic activity
- Endpoint summary
- Stability
- Biodegradation
- Bioaccumulation
- Transport and distribution
- Environmental data
- Additional information on environmental fate and behaviour
- Ecotoxicological Summary
- Aquatic toxicity
- Endpoint summary
- Short-term toxicity to fish
- Long-term toxicity to fish
- Short-term toxicity to aquatic invertebrates
- Long-term toxicity to aquatic invertebrates
- Toxicity to aquatic algae and cyanobacteria
- Toxicity to aquatic plants other than algae
- Toxicity to microorganisms
- Endocrine disrupter testing in aquatic vertebrates – in vivo
- Toxicity to other aquatic organisms
- Sediment toxicity
- Terrestrial toxicity
- Biological effects monitoring
- Biotransformation and kinetics
- Additional ecotoxological information
- Toxicological Summary
- Toxicokinetics, metabolism and distribution
- Acute Toxicity
- Irritation / corrosion
- Sensitisation
- Repeated dose toxicity
- Genetic toxicity
- Carcinogenicity
- Toxicity to reproduction
- Specific investigations
- Exposure related observations in humans
- Toxic effects on livestock and pets
- Additional toxicological data
Basic toxicokinetics
Administrative data
- Endpoint:
- basic toxicokinetics in vivo
- Type of information:
- experimental study
- Adequacy of study:
- supporting study
- Reliability:
- 2 (reliable with restrictions)
- Rationale for reliability incl. deficiencies:
- other: Acceptable, well-documented publication which meets basic scientific principles
Data source
Reference
- Reference Type:
- publication
- Title:
- Unnamed
- Year:
- 1 969
Materials and methods
- Objective of study:
- other: absorption and degradation
Test guideline
- Qualifier:
- no guideline followed
- GLP compliance:
- not specified
Test material
- Reference substance name:
- Mecrilate
- EC Number:
- 205-275-2
- EC Name:
- Mecrilate
- Cas Number:
- 137-05-3
- Molecular formula:
- C5H5NO2
- IUPAC Name:
- methyl 2-cyanoprop-2-enoate
- Test material form:
- other: liquid (Part 1) or polymerized powder (Part 2)
- Details on test material:
- - Part 1: radioactive methyl α-cyanoacrylate (MCA, 18.4 x 10E6 dpm/mL) or n-butyl α-cyanoacrylate (BCA, 14.9 x 10E6 dpm/mL)
- Part 2: radioactive methyl α-cyanoacrylate polymer powder (21.8 x 10E6 dpm/g) or n-butyl α-cyanoacrylate polymer powder (18.3 x 10E6 dpm/g)
Constituent 1
- Radiolabelling:
- yes
- Remarks:
- 14C
Test animals
- Species:
- rat
- Strain:
- Sprague-Dawley
- Sex:
- not specified
- Details on test animals or test system and environmental conditions:
- - Part 1: Rats weighing approx. 375g were placed singly in limited-motion metabolic cages. Hydration was maintained, during the period of the study, with subcutaneous and intraperitoneal injections of sterile normal saline solution (no feeding).
- Part 2: Rats weighing approx. 425g were placed singly in limited-motion metabolic cages and allowed to eat and drink ad libitum.
Administration / exposure
- Route of administration:
- other: Part 1: oral mucosa / Part 2: oral feeding tube
- Vehicle:
- other: Part 1: unchanged (no vehicle) / Part 2: vegetable oil
- Details on exposure:
- - Part 1: liquid application of test material on intact oral mucosa of the cheeks (ligated esophagus)
- Part 2: placement of polymer powder with vegetable oil as a vehicle in the stomach using a size 8 French feeding tube - Duration and frequency of treatment / exposure:
- - Part 1: 2 days, single application
- Part 2: 4 days, single application
Doses / concentrations
- Remarks:
- Doses / Concentrations:
- Part 1: 0.05 mL of methyl α-cyanoacrylate-ß-14C or n-butyl α-cyanoacrylate-ß-14C
- Part 2: 100 mg of polimerized powder of methyl α-cyanoacrylate-ß-14C or n-butyl α-cyanoacrylate-ß-14C
- No. of animals per sex per dose / concentration:
- - Part 1: total 4, 2 for each substance
- Part 2: total 4, 2 for each substance - Control animals:
- no
- Positive control reference chemical:
- no
- Details on study design:
- see "any other information on materials and methods"
- Details on dosing and sampling:
- see "any other information on materials and methods"
- Statistics:
- no data
Results and discussion
- Preliminary studies:
- not applicable
Main ADME resultsopen allclose all
- Type:
- absorption
- Results:
- MCA / intact oral mucosa: approx. 1 % per day (urine)
- Type:
- absorption
- Results:
- BCA / intact oral mucosa: max. 0.1 % per day (urine)
- Type:
- other: degradation
- Results:
- MCA polymer powder / stomach: approx. 15.9 % total (urine)
- Type:
- other: degradation
- Results:
- BCA polymer powder / stomach: approx. 2.2 % total (urine)
- Type:
- excretion
- Results:
- MCA polymer powder / stomach: approx. 17.8 % total (stool)
- Type:
- excretion
- Results:
- BCA polymer powder / stomach: approx. 73.1 % total (stool)
Toxicokinetic / pharmacokinetic studies
- Details on absorption:
- The mechanism of absorption of cyanoacrylate applied to intact oral mucosa (Part 1) is not known.
- Details on distribution in tissues:
- Not in the scope of the study.
- Details on excretion:
- see "any other information on results"
Metabolite characterisation studies
- Metabolites identified:
- not measured
- Details on metabolites:
- The hydrolytic degradation of cyanoacrylate has been reported (J. Appl. Polym. Sc. 10, 259-272, 1966). During hydrolytic degradation, water molecules are randomly added to the polymer chain at the beta carbon atoms, which then degrades to a polymer fraction (ultimately alkyl cyanoacetate) and formaldehyde. If the monomer has carbon-14 in the beta position, much of the carbon-14 is ultimately found in urine as urea-14C, a product of formaldehyde metabolism.
Bioaccessibility (or Bioavailability)
- Bioaccessibility (or Bioavailability) testing results:
- not applicable
Any other information on results incl. tables
PART 1
The radioactivity of urine, representing carbon-14 oral absorption from MCA or BCA monomer polymerized on intact oral mucosa, was determined as shown in Table 1.
TABLE 1: % of original radioactivity counted in urine
rat no. / test material |
day 1 |
day 2 |
total |
1 / MCA |
1.1 |
1.1 |
2.2 |
2 / MCA |
1.0 |
0.4 |
1.4 |
average / MCA |
1.1 |
0.8 |
1.8 |
3 / BCA |
0.1 |
0.1 |
0.2 |
4 / BCA |
no |
no |
no |
average / BCA |
0.1 |
0.1 |
0.1 |
PART 2
MCA or BCA polymer powder was placed in the rat's stomach and the carbon-14 radioactivity of urine and stool was determined. The urine radioactivity represents polymer degradation, while the stool carbon-14 activity probably represents primarily undegraded polymer.
The data from this portion of the study are shown in Table 2.
The hydrolytic degradation rate of MCA is relatively fast when compared to BCA, therefore only a small percentage of radioactivity from MCA has been found in the stool, compared to BCA, while a large percentage of radioactivity from MCA has been obtained in the urine, compared to BCA.
The 4 days of stool collection seem to be adequate in view of the lack of low level of radioactivity in the stools and urine on the fourth day of collection and the report that the gastrointestinal clearance time in the rat is approximately 3 days.
TABLE 2: % of original radioactivity delivered to stomach
rat no. / test material / sample |
day 1 |
day 2 |
day 3 |
day 4 |
total |
5 / MCA / urine |
5.7 |
2.8 |
0.6 |
0.1 |
9.2 |
6 / MCA / urine |
9.4 |
11.5 |
1.7 |
no |
22.6 |
average / MCA / urine |
7.6 |
7.2 |
1.2 |
0.1 |
15.9 |
7 / BCA / urine |
1.8 |
no |
no |
no |
1.8 |
8 / BCA / urine |
2.1 |
0.3 |
0.1 |
no |
2.5 |
average / BCA / urine |
2.0 |
0.2 |
0.1 |
no |
2.2 |
5 / MCA / stool |
2.5 |
8.0 |
0.4 |
no |
10.9 |
6 / MCA / stool |
0.6 |
20.2 |
3.6 |
0.2 |
24.6 |
average / MCA / stool |
1.6 |
14.1 |
2.0 |
0.1 |
17.8 |
7 / BCA / stool |
80.4 |
7.5 |
0.7 |
0.4 |
89.0 |
8 / BCA / stool |
28.3 |
21.7 |
5.1 |
2.1 |
57.2 |
average / BCA / stool |
54.4 |
14.6 |
2.9 |
1.3 |
73.1 |
Applicant's summary and conclusion
- Conclusions:
- Interpretation of results (migrated information): other: Because of limited oral absorption and fast degradation, a low bioaccumulation potential is assumed.
When MCA monomer was applied to the oral mucosa of rats, the absorption rate of 1%/day corresponded to the rate of degradation that is known for implanted MCA. After application of MCA polymer via gavage, degradation occured, and 33.7% of the original radioactivity was found in the urine and the stool within four days. - Executive summary:
Absorption and assimilation of methyl- and n-butyl α-cyanoacrylate-ß-14C was evaluated in the digestive tract of the rat. By evaluating the urine for carbon-14, it was demonstrated that there is absorption of monomer and/or polymer degradation products of cyanoacrylate when applied as a monomer and allowed to polymerize on the oral mucosa.
It was also demonstrated that if these materials in polymer form were to be inadvertently swallowed, degradation and assimilation of a significant percentage of the polymer would occur.
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