Terconazole (CED0010314)

Record Information

Version

1.0

Creation Date

2016-05-22 05:11:02 UTC

Update Date

2026-08-22 06:36:03 UTC

Accession Number

CHEM018358

Identification

Common Name

Terconazole

Class

Small Molecule

Description

Terconazole is an organic compound with the chemical formula C26H31Cl2N5O3. Terconazole belongs to the piperazines, a subclass of diazinanes within the organic compounds. With an average molecular weight of 532.46 g/mol, Terconazole is a heavy molecule. In terms of biological activity, it acts as an antagonist of the protein target Lanosterol 14-alpha demethylase (ERG11). The compound is associated with six recorded sources. Within healthcare, pharmaceuticals, and veterinary products, it is used in gynecologicals, and the recorded exposure route is vaginal. Other recorded sources include antennas in electrical and electronic equipment, as well as household cleaning and consumer products such as other smoking requisites and non electric simulated smoking devices. Additionally, it is linked to food, food processing, and cookware, specifically in the preparation of wine or sparkling wine and the preparation of malt.

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Terazol 3	Kegg
Triaconazole	HMDB
1-(4-((2-(2,4-Dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl)methoxy)phenyl)-4-(1-methylethyl)piperazine	HMDB
Cilag brand OF terconazole	HMDB
Janssen brand OF terconazole	HMDB
Fungistat	HMDB
Ortho brand OF terconazole	HMDB
Gyno-terazol	HMDB
Terazol	HMDB
Terconazole	MeSH

Chemical Formula

C₂₆H₃₁Cl₂N₅O₃

Average Molecular Mass

532.462 g/mol

Monoisotopic Mass

531.180 g/mol

CAS Registry Number

67915-31-5

IUPAC Name

1-(4-{[(2R,4S)-2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)-4-(propan-2-yl)piperazine

Traditional Name

terconazole

SMILES

CC(C)N1CCN(CC1)C1=CC=C(OC[C@H]2CO[C@@](CN3C=NC=N3)(O2)C2=C(Cl)C=C(Cl)C=C2)C=C1

InChI Identifier

InChI=1S/C26H31Cl2N5O3/c1-19(2)31-9-11-32(12-10-31)21-4-6-22(7-5-21)34-14-23-15-35-26(36-23,16-33-18-29-17-30-33)24-8-3-20(27)13-25(24)28/h3-8,13,17-19,23H,9-12,14-16H2,1-2H3/t23-,26-/m0/s1

InChI Key

BLSQLHNBWJLIBQ-OZXSUGGESA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylpiperazines. Phenylpiperazines are compounds containing a phenylpiperazine skeleton, which consists of a piperazine bound to a phenyl group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Diazinanes

Sub Class

Piperazines

Direct Parent

Phenylpiperazines

Alternative Parents

Substituents

Phenylpiperazine
N-arylpiperazine
Aminophenyl ether
1,3-dichlorobenzene
Phenoxy compound
Phenol ether
Tertiary aliphatic/aromatic amine
Dialkylarylamine
Aniline or substituted anilines
Alkyl aryl ether
Chlorobenzene
Halobenzene
Ketal
N-alkylpiperazine
Benzenoid
Aryl chloride
Aryl halide
Monocyclic benzene moiety
Heteroaromatic compound
1,2,4-triazole
Azole
Meta-dioxolane
Tertiary amine
Tertiary aliphatic amine
Ether
Acetal
Azacycle
Oxacycle
Organonitrogen compound
Organochloride
Organohalogen compound
Organic nitrogen compound
Hydrocarbon derivative
Organooxygen compound
Organic oxygen compound
Organopnictogen compound
Amine
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

1-(4-\{[2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy\}phenyl)-4-isopropylpiperazine (CHEBI:82980 )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Organoleptic Effects

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.012 g/L	ALOGPS
logP	4.58	ALOGPS
logP	5.37	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Basic)	8.41	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	64.88 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	153.19 m³·mol⁻¹	ChemAxon
Polarizability	56.15 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-001j-9443500000-9564806da5509b610135	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-00o0-3971230000-dd66741ee49b1efec5ef	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-001i-1031290000-ae9cf158d06c702d6779	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-006y-2030900000-107157b00d324c679eaf	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00di-9650000000-20fe5c34ac5ea92694b0	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-014i-9040020000-0b48b94660b9f3ef6e8b	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-014i-9020000000-63022b7fa681bfa05832	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-014i-9430000000-2d5aaa4b68e19d7bf8e6	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-001i-0000290000-f3aef95a41e4260dde02	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-001i-0001590000-49599976d635f6aacd4b	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0c0r-5589830000-780cdd0e0d8417618e23	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-001i-2000090000-c74ac4cbd2cd12fcbaeb	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00lr-6190360000-c1e756aeed62c3137090	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00o0-3920210000-06b53e2e06769acd7c3c	Not Available	View Spectrum

Toxicity Profile

Mechanism of Toxicity

Not Available

Carcinogenicity (IARC Classification)

Not Available

Minimum Risk Level

Not Available

Symptoms

Not Available

Treatment

Not Available

Toxicity Values

Toxicity Value	Unit	Value Range	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Reference
246.0	Log mg/kg	[140:440]	Rat	LD50	oral	predicted	Not Available

Health Effects

Health Effect	Relationship	Direction	Reference

Exposure Sources

Source ID	Source	Sector	Reference
316	Gynecologicals	Healthcare, pharmaceuticals & veterinary products	Not Available
506	Antennas	Electrical & Electronic Equipment	Not Available
547	Preparation Of Malt	Food, food processing & cookware	Not Available
549	Preparation Of Wine Or Sparkling Wine	Food, food processing & cookware	Not Available
559	Non Electric Simulated Smoking Devices	Household cleaning & consumer products	Not Available
560	Other Smoking Requisites	Household cleaning & consumer products	Not Available
583	Anchoring Equipment	Marine, shipping & aquaculture	Not Available
616	Face Mask Cosmetics	Personal care & cosmetics	Not Available
619	Manicure Pedicure	Personal care & cosmetics	Not Available
630	Toys	Recreation & sports surfaces	Not Available
643	Headwear	Textiles, leather & furnishings	Not Available
653	Sewing	Textiles, leather & furnishings	Not Available

Pathways

2 pathways

Terconazole Action Pathway

Terconazole Drug Metabolism Action Pathway

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	Cytochrome P450 3A4	P08684	Humans	Predicted (SEA)	4.7488
Click to view 3D structure	Cytochrome P450 2A2	P15149	Rat	Predicted (SEA)	0.467095
Click to view 3D structure	Lanosterol 14-alpha demethylase	Q4PJW3	Bos taurus	Predicted (SEA)	0.389246
Click to view 3D structure	Cholesterol side-chain cleavage enzyme, mitochondrial	P14137	Rattus norvegicus	Predicted (SEA)	0.467095
Click to view 3D structure	Cytochrome P450 7A1	P18125	Rattus norvegicus	Predicted (SEA)	0.467095
Click to view 3D structure	Lanosterol 14-alpha demethylase	Q16850	Humans	Predicted (SEA)	0.0778492
Click to view 3D structure	Steroid 21-hydroxylase	P08686	Humans	Predicted (SEA)	1.32344
Click to view 3D structure	Aromatase	P11511	Humans	Predicted (SEA)	2.95827
Click to view 3D structure	Heme oxygenase 1	P06762	Rattus norvegicus	Predicted (SEA)	0.778492
Click to view 3D structure	Heme oxygenase 2	P23711	Rattus norvegicus	Predicted (SEA)	0.700643
Click to view 3D structure	Lanosterol 14-alpha demethylase	Q64654	Rattus norvegicus	Predicted (SEA)	0.856341
Click to view 3D structure	Alpha-2B adrenergic receptor	P18089	Humans	Predicted (SEA)	12.5337
Click to view 3D structure	Alpha-2A adrenergic receptor	P08913	Humans	Predicted (SEA)	18.8395
Click to view 3D structure	Sodium-dependent serotonin transporter	P31645	Humans	Predicted (SEA)	37.2119
Click to view 3D structure	Muscarinic acetylcholine receptor M2	P08172	Humans	Predicted (SEA)	8.40772
Click to view 3D structure	7-alpha-hydroxycholest-4-en-3-one 12-alpha-hydroxylase	Q9UNU6	Humans	Predicted (SEA)	0.233548
Click to view 3D structure	Cytochrome P450 11B1, mitochondrial	P15538	Humans	Predicted (SEA)	5.13805
Click to view 3D structure	Steroid 17-alpha-hydroxylase/17,20 lyase	P05093	Humans	Predicted (SEA)	5.13805
Click to view 3D structure	5-hydroxytryptamine receptor 2A	P28223	Humans	Predicted (SEA)	118.564
Click to view 3D structure	D(3) dopamine receptor	P35462	Humans	Predicted (SEA)	107.665
Click to view 3D structure	Sigma non-opioid intracellular receptor 1	Q99720	Humans	Predicted (SEA)	88.3589
Click to view 3D structure	Polyunsaturated fatty acid lipoxygenase ALOX15	P12530	Oryctolagus cuniculus	Predicted (SEA)	0.934191
Click to view 3D structure	ATP-dependent translocase ABCB1	P08183	Humans	Predicted (SEA)	16.5819
Click to view 3D structure	Cytochrome P450 11B1, mitochondrial	P15150	Bos taurus	Predicted (SEA)	0.467095
Click to view 3D structure	5-hydroxytryptamine receptor 2C	P28335	Humans	Predicted (SEA)	114.283