CAPTAN

US Previously Marketed

Details

Stereochemistry	ACHIRAL
Molecular Formula	C9H8Cl3NO2S
Molecular Weight	300.589
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@@]12CC=CC[C@]1([H])C(=O)N(SC(Cl)(Cl)Cl)C2=O

InChI

InChIKey=LDVVMCZRFWMZSG-OLQVQODUSA-N

InChI=1S/C9H8Cl3NO2S/c10-9(11,12)16-13-7(14)5-3-1-2-4-6(5)8(13)15/h1-2,5-6H,3-4H2/t5-,6+

HIDE SMILES / InChI

Molecular Formula	C9H8Cl3NO2S
Molecular Weight	300.589
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: http://npic.orst.edu/factsheets/captangen.pdf
Curator's Comment: description was created based on several sources, including: https://archive.epa.gov/pesticides/reregistration/web/pdf/0120red.pdf http://www.wikidoc.org/index.php/Captan http://www.ncbi.nlm.nih.gov/pubmed/20569196

Captan is a fungicide. It is used on a variety of agricultural and greenhouse food/feed crops, indoor non-food uses, seed treatments and ornamental plant sites. People who mixed captan products or worked in fields where captan had been applied reported eye and skin irritation. A few human volunteers reported skin irritation and allergic reactions after captan was applied to their backs. Captan was previously cited as Group B2, a probable human carcinogen by the US Environmental Protection Agency (EPA), but was reclassified in 2004. The EPA now states: “Captan is not likely to be a human carcinogen nor pose cancer risks of concern when used in accordance with approved product labels.”

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Aldehyde dehydrogenase 8 Target ID: CHEMBL1935 Sources: http://www.ncbi.nlm.nih.gov/pubmed/24491970	Inhibitor 8297
Estrogen receptor alpha 127 Target ID: CHEMBL206 Sources: http://www.ncbi.nlm.nih.gov/pubmed/15253041	Binding Agent 1064		142.0 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2578

AUC

Value	Dose	Co-administered	Analyte	Population
1652 nM × h/kg EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/21381057/	1 mg/kg bw single, oral dose: 1 mg/kg bw route of administration: Oral experiment type: SINGLE co-administered:		4-CYCLOHEXENE-1,2-DICARBOXIMIDE, CIS- plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
15.7 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/21381057/	1 mg/kg bw single, oral dose: 1 mg/kg bw route of administration: Oral experiment type: SINGLE co-administered:		4-CYCLOHEXENE-1,2-DICARBOXIMIDE, CIS- plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

Doses

Dose	Population	Adverse events
3.75 g 1 times / day single, oral Studied dose Dose: 3.75 g, 1 times / day Route: oral Route: single Dose: 3.75 g, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/14514005/	healthy, 17 years n = 1 Health Status: healthy Age Group: 17 years Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/14514005/	Other AEs: Headache, Nausea... Other AEs: Headache Nausea Weakness Numbness of limbs Sources: https://pubmed.ncbi.nlm.nih.gov/14514005/
0.5 % 1 times / day single, topical Studied dose Dose: 0.5 %, 1 times / day Route: topical Route: single Dose: 0.5 %, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/8365173/	healthy, 21 years n = 1 Health Status: healthy Age Group: 21 years Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/8365173/	Other AEs: Allergic reaction... Other AEs: Allergic reaction Sources: https://pubmed.ncbi.nlm.nih.gov/8365173/
0.5 % 1 times / day single, topical Studied dose Dose: 0.5 %, 1 times / day Route: topical Route: single Dose: 0.5 %, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/7924295/	healthy, 26 years n = 1 Health Status: healthy Age Group: 26 years Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/7924295/	Other AEs: Contact dermatitis... Other AEs: Contact dermatitis Sources: https://pubmed.ncbi.nlm.nih.gov/7924295/
0.1 % 1 times / day single, topical Studied dose Dose: 0.1 %, 1 times / day Route: topical Route: single Dose: 0.1 %, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/1839725/	healthy, 45 years n = 1 Health Status: healthy Age Group: 45 years Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/1839725/	Other AEs: Eczema... Other AEs: Eczema Sources: https://pubmed.ncbi.nlm.nih.gov/1839725/
0.1 % 1 times / day single, topical Studied dose Dose: 0.1 %, 1 times / day Route: topical Route: single Dose: 0.1 %, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/9923784/	healthy, 45 years n = 1 Health Status: healthy Age Group: 45 years Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/9923784/	Other AEs: Photosensitivity... Other AEs: Photosensitivity Sources: https://pubmed.ncbi.nlm.nih.gov/9923784/

AEs

AE	Dose	Population
Headache	3.75 g 1 times / day single, oral Studied dose Dose: 3.75 g, 1 times / day Route: oral Route: single Dose: 3.75 g, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/14514005/	healthy, 17 years n = 1 Health Status: healthy Age Group: 17 years Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/14514005/
Nausea	3.75 g 1 times / day single, oral Studied dose Dose: 3.75 g, 1 times / day Route: oral Route: single Dose: 3.75 g, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/14514005/	healthy, 17 years n = 1 Health Status: healthy Age Group: 17 years Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/14514005/
Numbness of limbs	3.75 g 1 times / day single, oral Studied dose Dose: 3.75 g, 1 times / day Route: oral Route: single Dose: 3.75 g, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/14514005/	healthy, 17 years n = 1 Health Status: healthy Age Group: 17 years Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/14514005/
Weakness	3.75 g 1 times / day single, oral Studied dose Dose: 3.75 g, 1 times / day Route: oral Route: single Dose: 3.75 g, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/14514005/	healthy, 17 years n = 1 Health Status: healthy Age Group: 17 years Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/14514005/
Allergic reaction	0.5 % 1 times / day single, topical Studied dose Dose: 0.5 %, 1 times / day Route: topical Route: single Dose: 0.5 %, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/8365173/	healthy, 21 years n = 1 Health Status: healthy Age Group: 21 years Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/8365173/
Contact dermatitis	0.5 % 1 times / day single, topical Studied dose Dose: 0.5 %, 1 times / day Route: topical Route: single Dose: 0.5 %, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/7924295/	healthy, 26 years n = 1 Health Status: healthy Age Group: 26 years Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/7924295/
Eczema	0.1 % 1 times / day single, topical Studied dose Dose: 0.1 %, 1 times / day Route: topical Route: single Dose: 0.1 %, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/1839725/	healthy, 45 years n = 1 Health Status: healthy Age Group: 45 years Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/1839725/
Photosensitivity	0.1 % 1 times / day single, topical Studied dose Dose: 0.1 %, 1 times / day Route: topical Route: single Dose: 0.1 %, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/9923784/	healthy, 45 years n = 1 Health Status: healthy Age Group: 45 years Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/9923784/

Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
		CYP2B 32 CYP3A 129 CYP1A2 701

Drug as perpetrator

Target	Modality	Activity
CYP1A2 1692	inducer 1573 Sources: https://www.sciencedirect.com/science/article/abs/pii/S0009279799001349 Page: 17.0	likely
CYP3A 298	inducer 1573 Sources: https://www.sciencedirect.com/science/article/abs/pii/S0009279799001349 Page: 17.0	likely
CYP2B 40	inducer 1573 Sources: https://pubmed.ncbi.nlm.nih.gov/11673071/ Page: 8.0	no
CYP1A1 218	supressor 155 Sources: https://www.sciencedirect.com/science/article/abs/pii/S0009279799001349 Page: 8 to 14	yes
CYP1A2 1692	supressor 155 Sources: https://www.sciencedirect.com/science/article/abs/pii/S0009279799001349 Page: 8 to 14	yes
CYP2B1 41	supressor 155 Sources: https://www.sciencedirect.com/science/article/abs/pii/S0009279799001349 Page: 8 to 14	yes
CYP2E1 970	supressor 155 Sources: https://www.sciencedirect.com/science/article/abs/pii/S0009279799001349 Page: 8 to 14	yes

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:34608	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:34608
ChemicalBook	CB4367608	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB4367608
MolPort	MolPort-006-109-747	https://www.molport.com/shop/molecule-link/MolPort-006-109-747
eMolecules	509613	https://www.emolecules.com/cgi-bin/more?vid=509613

PubMed

Title	Date	PubMed
Cytotoxicity and mutagenicity of the fungicides captan and folpet in cultured mammalian cells CHO/HGPRT system).	1981	7274179
A test series for pesticide dermatitis.	1986 Nov	2949929
Irritation and sensitization potential of pesticides.	1987 Oct	2962818
Evaluation of the carcinogenic potential of pesticides. 4. Chloroalkylthiodicarboximide compounds with fungicidal activity.	1993 Feb	8441825
Interaction of glutathione transferase P1-1 with captan and captafol.	1996 Jul 12	8678907
Estimation of estrogenic and antiestrogenic activities of selected pesticides by MCF-7 cell proliferation assay.	2004 May	15253041
Pesticide use and adult-onset asthma among male farmers in the Agricultural Health Study.	2009 Dec	19541724
Rhinitis associated with pesticide use among private pesticide applicators in the agricultural health study.	2010	20818537
Gender-linked haematopoietic and metabolic disturbances induced by a pesticide mixture administered at low dose to mice.	2010 Jan 12	19883720
A concentration addition model to assess activation of the pregnane X receptor (PXR) by pesticide mixtures found in the French diet.	2014 Sep	25028461
Population-based in vitro hazard and concentration-response assessment of chemicals: the 1000 genomes high-throughput screening study.	2015 May	25622337

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

Significant cytotoxicity of Captan on the human adrenocortical carcinoma cell line H295R was observed at the concentrations of 30 μM (26 %) and 100 μM (74 %).

Substance Class	Chemical Created by `admin` on `Sat Dec 16 05:45:18 GMT 2023` Edited by `admin` on `Sat Dec 16 05:45:18 GMT 2023`
Record UNII	EOL5G26Q9F
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

CAPTAN

Official Name

English

CAPTAN [II]

Common Name

English

CAPTAN [INCI]

Common Name

English

CAPTAN [IARC]

Common Name

English

CAPTAN [HSDB]

Common Name

English

CAPTAN [ISO]

Common Name

English

VANCIDE 89

Common Name

English

NSC-36726

Code

English

CAPTAN [MI]

Common Name

English

ORTHOCIDE-406

Brand Name

English

SR-406

Code

English

1H-ISOINDOLE-1,3(2H)-DIONE, 3A,4,7,7A-TETRAHYDRO-2-((TRICHLOROMETHYL)THIO)-, (3AR,7AS)-REL-

Common Name

English

N-(TRICHLOROMETHYLTHIO)CYCLOHEX-4-ENE-1,2-DICARBOXIMIDE

Common Name

English

MERPAN

Brand Name

English

ENT-26538

Code

English

1H-ISOINDOLE-1,3(2H)-DIONE, 3A,4,7,7A-TETRAHYDRO-2-((TRICHLOROMETHYL)THIO)-, CIS-

Common Name

English

4-CYCLOHEXENE-1,2-DICARBOXIMIDE, N-((TRICHLOROMETHYL)THIO)-, CIS-

Common Name

English

Classification Tree Code System Code

CFR

21 CFR 176.170