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Tioconazole

HCID 5482
NotesReactions
Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
Substructure searchFind similar structures

Basic information

CAS
65899-73-2
Standard SMILES
Clc1ccc(C(Cn2ccnc2)OCc2ccsc2Cl)c(Cl)c1
InChIKey
QXHHHPZILQDDPS-UHFFFAOYSA-N
Molecular formula
C16H13Cl3N2OS
Average molar mass
387.7 g/mol
Monoisotopic mass
385.98141708

Overview

1-{2-[(2-chloro-3-thienyl)methoxy]-2-(2,4-dichlorophenyl)ethyl}imidazole is a member of the class of imidazoles that comprises 2-(2,4-dichlorophenyl)ethylimidazole carrying an additional (2-chloro-3-thienyl)methoxy substituent at position 2. It is a dichlorobenzene, a member of imidazoles, an ether and a member of thiophenes.

Names & identifiers

Preferred name
Tioconazole
IUPAC
1-[2-[(2-chlorothiophen-3-yl)methoxy]-2-(2,4-dichlorophenyl)ethyl]imidazole
English name
Vagistat
Molecular formula
C16H13Cl3N2OS
Molecular weight
387.71

Names & synonyms

tioconazole65899-73-2VagistatVagistat-1TrosydTrosylTioconazolTioconazolumUK-203491-(2-((2-chlorothiophen-3-yl)methoxy)-2-(2,4-dichlorophenyl)ethyl)-1H-imidazole(+-)-TioconazoleDTXSID3046619
Show more names
ZonidenFungibacidVagistat 1ioconazoleGyno-Trosyd
UK 20349UK-20,349NSC-759169S57Y5X1117(+-)-1-(2,4-Dichloro-beta-((2-chloro-3-ethenyl)oxy)phenethyl)imidazoleDTXCID10266191H-Imidazole, 1-(2-((2-chloro-3-thienyl)methoxy)-2-(2,4-dichlorophenyl)ethyl)-1-{2-[(2-chlorothiophen-3-yl)methoxy]-2-(2,4-dichlorophenyl)ethyl}-1H-imidazole

Database identifiers

CAS
65899-73-2
PubChem CID
5482
DTXSID
DTXSID3046619
ChEMBL
CHEMBL1200438
ChEBI
CHEBI:77898
UNII
S57Y5X1117
EC Number
265-973-8
Nikkaji

Properties

Computed structural properties

XLogP
5.3
Topological polar surface area
55.3 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
3
Rotatable bonds
6
Heavy atoms
23
Formal charge
0
Complexity
379

Experimental & physicochemical properties

LogP4.4
Solubility1.65e-02 g/L
Human Drugs · 3 items

Breast Feeding; Lactation; Anti-Infective Agents; Antifungal Agents; Dermatologic Agents;

FDA approved drugs -> Active ingredient

FDA approved drugs -> Active ingredient

Physical DescriptionSolid
Collision Cross Section · 2 items

180.7 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

179.43 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

Physicochemical properties

Melting point
79 · 79-81oC
Boiling point
534.5 · 534.5±50.0 °C(Predicted)
Density
1.3115 · 1.3115 (rough estimate)
refractive index
1.6 · 1.6000 (estimate)
RTECS
4480000 · NI4480000

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 4 items

Warning

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

P203, P261, P264, P270, P272, P273, P280, P301+P317, P302+P352, P318, P321, P330, P333+P317, P362+P364, P391, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 100 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Hazard Classes and CategoriesAcute Tox. 4 (100%)

Toxicology

Exposure RoutesSystemic absorption following a single intravaginal application of tioconazole in nonpregnant patients is negligible.
Toxicity Summary · 1 item

Tioconazole interacts with 14-α demethylase, a cytochrome P-450 enzyme that converts lanosterol to ergosterol, an essential component of the yeast membrane. In this way, tioconazole inhibits ergosterol synthesis, resulting in increased cellular permeability. Tioconazole may also inhibit endogenous respiration, interact with membrane phospholipids, inhibit the transformation of yeasts to mycelial forms and the uptake of purine, impair triglyceride and/or phospholipid biosynthesis, and inhibit the movement of calcium and potassium ions across the cell membrane by blocking the ion transport pathway known as the Gardos channel.

Signs and SymptomsSymptoms of overdose include erythema, stinging, blistering, peeling, edema, pruritus, urticaria, burning, and general irritation of the skin, and cramps.
Carcinogen Classification

Chemistry & industry

Pharmacology

ATC Code · 4 items

D - Dermatologicals

G - Genito urinary system and sex hormones

QG - Genito urinary system and sex hormones

QD - Dermatologicals

Pharmacodynamics · 1 item

Tioconazole is a broad-spectrum imidazole antifungal agent that inhibits the growth of human pathogenic yeasts. Tioconazole exhibits fungicidal activity in vitro against <i>Candida albicans</i>, other species of the genus Candida, and against <i>Torulopsis glabrata</i>. Tioconazole prevents the growth and function of some fungal organisms by interfering with the production of substances needed to preserve the cell membrane. In addition to its broad spectrum antifungal effects with tioconazole being effective against commonly occurring dermatophyte and yeast-like fungal species, tioconazole also has antibacterial effects on certain Gram-positive cocci bacteria.

Mechanism of Action · 1 item

Tioconazole interacts with 14-&alpha; demethylase, a cytochrome P-450 enzyme that converts lanosterol to ergosterol, an essential component of the yeast membrane. In this way, tioconazole inhibits ergosterol synthesis, resulting in increased cellular permeability. Tioconazole may also inhibit endogenous respiration, interact with membrane phospholipids, inhibit the transformation of yeasts to mycelial forms and the uptake of purine, impair triglyceride and/or phospholipid biosynthesis, and inhibit the movement of calcium and potassium ions across the cell membrane by blocking the ion transport pathway known as the Gardos channel.

Metabolism/Metabolites · 2 items

Orally administered tioconazole is extensively metabolized. The major metabolites are glucuronide conjugates.

Orally administered tioconazole is extensively metabolized. The major metabolites are glucuronide conjugates.

FDA Pharmacological Classification · 6 items

S57Y5X1117

TIOCONAZOLE

Established Pharmacologic Class [EPC] - Azole Antifungal

Chemical Structure [CS] - Azoles

Tioconazole is an Azole Antifungal.

TIOCONAZOLE

Related reactions

3 records
New reaction record
HRID 1265340 reaction equation
HRID 1265340As productuspto-grants-2003_04
HRID 1265341 reaction equation
HRID 1265341As productuspto-grants-2003_04
HRID 1265342 reaction equation
HRID 1265342As productuspto-grants-2003_04

Compound notes

Loading…

On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
J3.525D
storage temp.
Keep in dark place,Inert atmosphere,Room temperature
solubility
Very slightly soluble in water, very soluble in methylene chloride, freely soluble in alcohol.
form
powder
pka
6.66 · 6.66±0.12(Predicted)
color
white to off-white
Cosmetics Ingredients Functions
ANTIMICROBIAL
InChI
InChI=1S/C16H13Cl3N2OS/c17-12-1-2-13(14(18)7-12)15(8-21-5-4-20-10-21)22-9-11-3-6-23-16(11)19/h1-7,10,15H,8-9H2
InChIKey
QXHHHPZILQDDPS-UHFFFAOYSA-N
SMILES
C1N(CC(OCC2C=CSC=2Cl)C2=CC=C(Cl)C=C2Cl)C=CN=1
CAS DataBase Reference
65899 · 65899-73-2(CAS DataBase Reference)
EWG's Food Scores
1 · 1
FDA UNII
57 Y5X1117 · S57Y5X1117
ATC code
1 AC07,G01AF08 · D01AC07,G01AF08
UNSPSC Code
51302325 · 51302325
NACRES
85 · NA.85
Symbol(GHS)
7 · GHS07,GHS08,GHS09
Signal word
Warning
Hazard statements
302 · H302-H317-H361d-H410
Precautionary statements
202 · P202-P273-P280-P301+P312-P302+P352-P308+P313
PPE
95 · dust mask type N95 (US), Eyeshields, Gloves
Hazard Codes
Xn
Risk Statements
22 · 22
RIDADR
3077 · UN3077
WGK Germany
3 · 3
HazardClass
9 · 9
HS Code
2934990002 · 2934990002
Storage Class
11 · 11 - Combustible Solids
Hazard Classifications
4 OralAquatic · Acute Tox. 4 OralAquatic Acute 1Aquatic Chronic 1Repr. 2Skin Sens. 1
Limited Quantities
5 kg · 5.0 kg (11 lbs) (solid)
Excepted Quantities
Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L)
No indication of carcinogenicity to humans (not listed by IARC).
Effects During Pregnancy and Lactation◉ Summary of Use during Lactation

Safety data

PPE
dust mask type N95 (US), Eyeshields, Gloves
wgk
3
ridadr
UN3077
hs_code
2934990002
risk_code
22
Signal word
Warning
Symbol(GHS)
GHS07,GHS08,GHS09
hazard_code
Xn
hazard_class
9
Storage Class
11 - Combustible Solids
Hazard statements
H302-H317-H361d-H410
Limited Quantities
5.0 kg (11 lbs) (solid)
Excepted Quantities
Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L)
Hazard Classifications
Acute Tox. 4 OralAquatic Acute 1Aquatic Chronic 1Repr. 2Skin Sens. 1
Precautionary statements
P202-P273-P280-P301+P312-P302+P352-P308+P313
MeSH Pharmacological Classification · 2 items

Substances that destroy fungi by suppressing their ability to grow or reproduce. They differ from FUNGICIDES, INDUSTRIAL because they defend against fungi present in human or animal tissues.

Compounds that specifically inhibit STEROL 14-DEMETHYLASE. A variety of azole-derived ANTIFUNGAL AGENTS act through this mechanism.

Absorption, Distribution and ExcretionSystemic absorption following a single intravaginal application of tioconazole in nonpregnant patients is negligible.
Cellular LocationsCytoplasm

Uses & manufacturing

UsesFor the local treatment of vulvovaginal candidiasis (moniliasis).
Applications · 4 items

DescriptionTioconazole is an antifungal agent, closely related to miconazole. Tioconazole is effective in the topical treatment of superficial fungal infections and appears to be more potent than miconazole against Candida and Trichophyton species.

UsesPotent inhibitor of cytochrome-P450

UsesTioconazole is an antifungal that is more active than Fluconazole (F421000) or Voriconazole (V760000) against Candida glabrata mutant strains. Antifungal (topical).

Usesantithrombotic

Upstream & downstream products

Upstream raw materials

2-Chloro-3-chloromethylthiopheneSodium hydridealpha-(2,4-Dichlorophenyl)-1H-imidazole-1-ethanol

Suppliers100 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
北京华美互利生物化工010-56205725 · [email protected]
湖北永阔科技有限公司027-59223108 15972152991 · [email protected]
南通飞宇生物科技有限公司0513-68819626 15152877458 · [email protected]
江苏瑞点药业有限公司15896106238 · [email protected]
湖北金梭生物科技有限公司00123456789 · [email protected]
T&W GROUP021-61551611 13296011611 · [email protected]
湖北科乐精细化工有限公司027-59101668 19945030958 · [email protected]
Dayang Chem (Hangzhou) Co.,Ltd.+86-0571-88938639 17705817739 · [email protected]
南京世洲生物科技有限公司025-025-85560043 17301488900 · [email protected]
LGM Pharma1-(800)-881-8210 · [email protected]
江西瑞威尔生物科技有限公司400-880-2824 18107960669 · [email protected]
江西瑞威尔生物科技有限公司18502728206 · [email protected]
江西瑞威尔生物科技有限公司18502762009 · [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(安徽泽升科技有限公司)021-58432009 400-005-6266 · [email protected]
梯希爱(上海)化工贸易有限公司021-61109150 · [email protected]
常州科化生物科技有限公司0519-68985668 13685222090 · [email protected]
广东云星生物技术有限公司0751-18902340975/189023400307 18902340307 · [email protected]
南京圣亿来化工有限公司19951936396 · [email protected]
MedBio脉铂医药021-69568360 18916172912 · [email protected]
上海相辉医药科技有限公司13761987713 · [email protected]
Pure Chemistry Scientific Inc.001-857-928-2050 or 1-888-588-9418 · [email protected]
上海泰坦科技股份有限公司4006009262 13023226327 · [email protected]
凯试(上海)科技有限公司021-50135380 · [email protected]
MedChemexpress LLC021-58955995 · [email protected]
孝感深远化工有限公司15527621225; 15527621225 · [email protected]
斯百全化学(上海)有限公司021-021-021-67601398-809-809-809 15221380277 · [email protected]
AdooQ BioScience, LLC+1 (866) 930-6790 · [email protected]
上海贤鼎生物科技有限公司4009209199 · [email protected]
深圳振强药物研发有限公司0755-66853366 13670046396 · [email protected]
广州爱纯医药科技有限公司020-39119399 18927568969 · [email protected]
武汉鹏胤药业有限公司13163333255 · [email protected]
湖北威德利化学试剂有限公司186-02735115 18602735115 · [email protected]
湖北鑫源顺医药化工有限公司13971561712, 13995564702, 027-50664929 · [email protected]
天津普西唐生物医药科技有限公司010-60605840 · [email protected]
南京百鑫德诺生物科技有限公司025-58849295 · [email protected]
湖北巨胜科技有限公司027-59599241 18871490274 · [email protected]
池州凯隆进出口贸易有限公司[email protected]
桦特昇生物科技(武汉)有限公司027-59207879 1972026995 18140587686 · [email protected]
珠海安哲生物科技有限公司13169972583 · [email protected]
TargetMol中国(陶术生物)021-021-33632979 15002134094 · [email protected]
上海陶术生物科技股份有限公司+1-781-999-5354; +1-00000000000 · [email protected]
湖北威德利化学科技有限公司027-83989310 18627915365 · [email protected]
湖北威德利化学试剂有限公司18327179646 · [email protected]
湖北辰心化工有限公司17362916295 · [email protected]
Qiuxian Baitai New Material Co., LTD+86-19932103556 · [email protected]
上海珞珐生化科技有限公司021-51111890 15317326293 · [email protected]
郑州阿尔法化工有限公司0371-53765687 18937137882 · [email protected]
成都润泽本土化工有限公司028-88469284 18000562381 · [email protected]

Additional notes

DefinitionChEBI: A member of the class of imidazoles that comprises 2-(2,4-dichlorophenyl)ethylimidazole carrying an additional (2-chloro-3-thienyl)methoxy substituent at position 2.