Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C12H11NO2 |
| Molecular Weight | 201.2212 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CNC(=O)OC1=C2C=CC=CC2=CC=C1
InChI
InChIKey=CVXBEEMKQHEXEN-UHFFFAOYSA-N
InChI=1S/C12H11NO2/c1-13-12(14)15-11-8-4-6-9-5-2-3-7-10(9)11/h2-8H,1H3,(H,13,14)
| Molecular Formula | C12H11NO2 |
| Molecular Weight | 201.2212 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
DescriptionSources: http://www.toxipedia.org/display/toxipedia/CarbarylCurator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/6814883 and https://www.ncbi.nlm.nih.gov/pubmed/6804141
Sources: http://www.toxipedia.org/display/toxipedia/Carbaryl
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/6814883 and https://www.ncbi.nlm.nih.gov/pubmed/6804141
Carbaryl (1-naphthyl methylcarbamate) is a chemical in the carbamate family used chiefly as an insecticide. It is a white crystalline solid commonly sold under the brand name Sevin, a trademark of the Bayer Company.Union Carbide discovered carbaryl and introduced it commercially in 1958. Bayer purchased Aventis CropScience in 2002, a company that included Union Carbide pesticide operations. It remains the third-most-used insecticide in the United States for home gardens, commercial agriculture, and forestry and rangeland protection. As a veterinary drug, it is known as carbaril. Carbaryl is an anticholinesterase inhibitor. It is indicated for the treatment of head and pubic lice. It is available as a lotion (Carylderm) and a shampoo (Carylderm; New Suleo; Derbac). Carbaryl was developed because lice began to show resistance to organochlorine insecticides such as DDT and gamma benzene hexachloride (Quellada; Lorexane). It was introduced in the late 1960s particularly for the control of head lice; it is less effective against mites, and not recommended for scabies.
Originator
Sources: http://www.toxipedia.org/display/toxipedia/Carbaryl
Curator's Comment: Discovered in 1958 by Union Carbide
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL220 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23632007 |
109.98 µM [IC50] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Curative | Carylderm Approved UseFor the treatment of head lice infections |
Doses
| Dose | Population | Adverse events |
|---|---|---|
0.5 % single, topical Studied dose |
unhealthy, CHILD|ADULT Health Status: unhealthy Age Group: CHILD|ADULT Sex: M+F Food Status: UNKNOWN Sources: |
Other AEs: Scalp irritation, Irritation skin... Other AEs: Scalp irritation Sources: Irritation skin Flaking skin Stinging Eyes irritation |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| Eyes irritation | 0.5 % single, topical Studied dose |
unhealthy, CHILD|ADULT Health Status: unhealthy Age Group: CHILD|ADULT Sex: M+F Food Status: UNKNOWN Sources: |
|
| Flaking skin | 0.5 % single, topical Studied dose |
unhealthy, CHILD|ADULT Health Status: unhealthy Age Group: CHILD|ADULT Sex: M+F Food Status: UNKNOWN Sources: |
|
| Irritation skin | 0.5 % single, topical Studied dose |
unhealthy, CHILD|ADULT Health Status: unhealthy Age Group: CHILD|ADULT Sex: M+F Food Status: UNKNOWN Sources: |
|
| Scalp irritation | 0.5 % single, topical Studied dose |
unhealthy, CHILD|ADULT Health Status: unhealthy Age Group: CHILD|ADULT Sex: M+F Food Status: UNKNOWN Sources: |
|
| Stinging | 0.5 % single, topical Studied dose |
unhealthy, CHILD|ADULT Health Status: unhealthy Age Group: CHILD|ADULT Sex: M+F Food Status: UNKNOWN Sources: |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Multiresidue screening methods for the determination of pesticides in tomatoes. | 2003-09 |
|
| Amperometric and spectrophotometric determination of carbaryl in natural waters and commercial formulations. | 2003-09 |
|
| Competitive degradation and detoxification of carbamate insecticides by membrane anodic Fenton treatment. | 2003-08-27 |
|
| Characterization of cholinesterase activity in three bivalves inhabiting the North Adriatic sea and their possible use as sentinel organisms for biosurveillance programmes. | 2003-08-01 |
|
| A simple method for the determination of carbaryl and 1-naphthol in fruit juices by high-performance liquid chromatography-diode-array detection. | 2003-08 |
|
| Evaluation of pesticide uptake by Lupinus seeds. | 2003-08 |
|
| Monitoring some phenoxyl-type N-methylcarbamate pesticide residues in fruit juices using high-performance liquid chromatography with peroxyoxalate-chemiluminescence detection. | 2003-07-25 |
|
| Multiresidue analysis of carbamate pesticides in soil by sonication-assisted extraction in small columns and liquid chromatography. | 2003-07-25 |
|
| Susceptibility of black fly larvae (Diptera: Simuliidae) to lawn-care insecticides individually and as mixtures. | 2003-07 |
|
| Development of a toxic bait for control of eastern lubber grasshopper (Orthoptera: Acrididae). | 2003-06 |
|
| Continuous ultrasound-assisted extraction coupled to on line filtration-solid-phase extraction-column liquid chromatography--post column derivatisation-fluorescence detection for the determination of N-methylcarbamates in soil and food. | 2003-05-23 |
|
| Photodecomposition of carbaryl in the presence of silver-doped zeolite Y and Suwannee River natural organic matter. | 2003-05-15 |
|
| Considerations on ultra trace analysis of carbamates in water samples. | 2003-05-09 |
|
| Analysis of pesticides in water and sediment under different storage conditions using gas chromatography. | 2003-05 |
|
| [Simultaneous determination of carbaryl and propanil in human serum and urine by on-line column-switching technique followed by automatic reversed-phase HPLC]. | 2003-04 |
|
| Simultaneous analysis of carbamate pesticides in tap and raw water by LC/ESI/MS. | 2003-04 |
|
| Environmental monitoring of carbaryl applied in urban areas to control the glassy-winged sharpshooter in California. | 2003-03 |
|
| Inhibition of neurite outgrowth in N2a cells by leptophos and carbaryl: effects on neurofilament heavy chain, GAP-43 and HSP-70. | 2003-02 |
|
| Biological targets of neurotoxic pesticides analysed by alteration of developmental events in the Mediterranean sea urchin, Paracentrotus lividus. | 2003-02 |
|
| Turfgrass thatch effects on pesticide leaching: a laboratory and modeling study. | 2003-01-29 |
|
| Toxic effects of dimethoate and carbaryl pesticides on protein metabolism of the freshwater snail Lymnaea acuminata. | 2003-01 |
|
| Tumorigenic potential of carbaryl in the heterozygous p53 knockout mouse model. | 2003-01 |
|
| Long-term effectiveness of grain protectants and structural treatments against Liposcelis decolor (Pearman) (Psocoptera: Liposcelididae), a pest of stored products. | 2002-12 |
|
| Photoinduced degradation of carbaryl in a wetland surface water. | 2002-11-06 |
|
| Rapid enzyme immunoassays for the detection of carbaryl and methoprene in grains. | 2002-11 |
|
| In vitro metabolism of carbaryl by human cytochrome P450 and its inhibition by chlorpyrifos. | 2002-10-20 |
|
| Effects of Sevin (carbaryl insecticide) on early life stages of zebrafish (Danio rerio). | 2002-10 |
|
| Effects of pesticides on DNA and protein of shrimp larvae Litopenaeus stylirostris of the California Gulf. | 2002-10 |
|
| Carbaryl resistance in populations of grape berry moth (Lepidoptera: Tortricidae) in New York and Pennsylvania. | 2002-10 |
|
| A comparison between two brine shrimp assays to detect in vitro cytotoxicity in marine natural products. | 2002-09-23 |
|
| Insecticide susceptibilities of cat fleas (Siphonaptera: Pulicidae) from several regions of the United States. | 2002-09 |
|
| Causes of ambient toxicity in the Calleguas Creek watershed of southern California. | 2002-09 |
|
| Derivatization reactions of carbamate pesticides in supercritical carbon dioxide. | 2002-09 |
|
| Hazards of insecticides to the bumble bees Bombus impatiens (Hymenoptera: Apidae) foraging on flowering white clover in turf. | 2002-08 |
|
| Broad-spectrum insecticide resistance in obliquebanded leafroller Choristoneura rosaceana (Lepidoptera: Tortricidae) from Michigan. | 2002-08 |
|
| Purification and biochemical characterization of the carbamate hydrolase from Pseudomonas sp. 50432. | 2002-08 |
|
| Viability of textile systems for hand and body protection: effects of chemical interaction, wear, and storage conditions. | 2002-08 |
|
| Imidacloprid residues in Willapa Bay (Washington State) water and sediment following application for control of burrowing shrimp. | 2002-07-17 |
|
| [Analysis of carbaryl and other pesticides by capillary electrophoresis]. | 2002-07 |
|
| Validation of a method for the determination of multiclass pesticide residues in fruit juices by liquid chromatography/tandem mass spectrometry after extraction by matrix solid-phase dispersion. | 2002-06-27 |
|
| Pesticide impact on excretory physiology of the common frog, Rana tigrina (Daud) tadpoles. | 2002-05 |
|
| Electrochemical detection of carbamate pesticides at conductive diamond electrodes. | 2002-04-01 |
|
| Carbaryl-induced alterations in biochemical metabolism of the prawn, Macrobrachium malcolmsonii. | 2002-04 |
|
| Toxic effects of dimethoate and carbaryl pesticides on carbohydrate metabolism of freshwater snail Lymnaea acuminata. | 2002-04 |
|
| Evaluation of safety and efficacy of acaricides for control of the African tortoise tick (Amblyomma marmoreum) on leopard tortoises (Geochelone pardalis). | 2002-03 |
|
| Effect of some insecticides on acetylcholinesterase from beneficial insects: Coccinella septempunctata, Chrysoperla carnea and Forficula auricularia. | 2002 |
|
| The use of the radioisotope method in studies of pesticide penetration into the eyeball. | 2002 |
|
| Progress toward understanding the neurophysiological basis of predator-induced morphology in Daphnia pulex. | 2001-12-21 |
|
| Effect of pesticides carbaryl and phorate on serum cholesterol level in fish, Clarias batrachus (Linn). | 2001-07 |
|
| Episodic exposures to chemicals: what relevance to chemical intolerance? | 2001-03 |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.drugs.com/uk/pdf/leaflet/717199.pdf
Carylderm solution should be applied to the hair and scalp and left for 10 to 12 hours, to ensure that all the eggs are treated. This is eventually washed out and the eggs removed from the scalp using a special nit comb. It is usually recommended that family members and close contacts be treated at the same time, if infected. In the event of early re-infestation of lice from surviving eggs, carylderm preparations may be reapplied, provided 7 days have elapsed since the first application.
Route of Administration:
Topical
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27296064
Rat hair cell and neuronal damage was observed at carbaryl concentrations as low as 50 uM after 96-h treatment and 100 uM after 48-h treatment.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Wed Apr 02 09:30:17 GMT 2025
by
admin
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Wed Apr 02 09:30:17 GMT 2025
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| Record UNII |
R890C8J3N1
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Validated (UNII)
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EPA PESTICIDE CODE |
56801
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IARC | Carbaryl | ||
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QP53AE01
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carbaryl
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Carbaryl
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