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Compound Detail

CHEMBL1714574

TERCONAZOLE
💊 Approved Drug
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💊 Approved Drug
CC(C)N1CCN(c2ccc(OCC3COC(Cn4cncn4)(c4ccc(Cl)cc4Cl)O3)cc2)CC1

Basic Information

ChEMBL ID CHEMBL1714574
Name TERCONAZOLE
Phase Approved
Structure Type MOL
InChI Key BLSQLHNBWJLIBQ-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

Fungistat Gyno-terazol NSC-331942 Panlomyc R 42470 R-42,470 R-42470 Terazol 3 Terazol 7 Terconazol Terconazole Tercospor +2 more
33
Targets
69
Activities
3
Assay Types
0
PK Parameters
20
Publications
14
Known Names
2
Indications
1
Mechanisms

Molecular Properties

532.5
MW (Da)
4.46
ALogP
8
HBA
0
HBD
64.9
PSA (Ų)
0.42
QED
1
Ro5 Violations
8
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1987
Availability Prescription
Chirality Racemic

Routes of Administration

Topical

Flags

Natural Product
USAN Stem -conazole
USAN Year 1980

Extended Properties

Molecular Formula C26H31Cl2N5O3
MW 532.47
Aromatic Rings 3
Heavy Atoms 36
NP-Likeness -0.85

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Cytochrome P450 51 inhibitor INHIBITOR Lanosterol 14-alpha demethylase

Indications

Candidiasis, Vulvovaginal Vaginitis

ATC Classification

G01AG02
terconazole
Level 1: GENITO URINARY SYSTEM AND SEX HORMONES
Level 2: GYNECOLOGICAL ANTIINFECTIVES AND ANTISEPTICS

Activity Summary

IC50 36 meas. best 6.5
Ki 28 meas. best 7.21
EC50 5 meas. best 6.4

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Alpha-2C adrenergic receptor
CHEMBL1916
Ki 7.21 7.21 61.0 1
Unchecked
CHEMBL612545
Ki 6.71 5.6757 195.0 7
Sigma non-opioid intracellular receptor 1
CHEMBL287
Ki 6.67 6.67 214.0 1
Unchecked
CHEMBL612545
IC50 6.5 5.4543 317.0 7
Alpha-2A adrenergic receptor
CHEMBL1867
Ki 6.43 6.43 369.0 1
Trypanosoma cruzi
CHEMBL368
EC50 6.4 6.4 400.0 1
Heme oxygenase 1
CHEMBL5035
IC50 6.39 6.39 410.0 1
Alpha-2C adrenergic receptor
CHEMBL1916
IC50 6.38 6.38 418.0 1
Sigma non-opioid intracellular receptor 1
CHEMBL287
IC50 6.29 6.29 508.0 1
Alpha-2A adrenergic receptor
CHEMBL1867
IC50 6.01 6.01 983.0 1
Alpha-2B adrenergic receptor
CHEMBL1942
Ki 5.9 5.9 1246.0 1
Muscarinic acetylcholine receptor M1
CHEMBL216
Ki 5.86 5.86 1375.0 1
D(3) dopamine receptor
CHEMBL234
Ki 5.8 5.8 1600.0 1
Muscarinic acetylcholine receptor M4
CHEMBL1821
Ki 5.72 5.72 1913.0 1
5-hydroxytryptamine receptor 2A
CHEMBL224
Ki 5.63 5.63 2336.0 1
5-hydroxytryptamine receptor 4
CHEMBL5017
Ki 5.61 5.61 2463.0 1
Polyunsaturated fatty acid lipoxygenase ALOX15
CHEMBL4358
IC50 5.61 5.61 2446.0 1
Alpha-2B adrenergic receptor
CHEMBL1942
IC50 5.56 5.56 2729.0 1
Lanosterol 14-alpha demethylase
CHEMBL3849
IC50 5.52 5.52 3000.0 1
Muscarinic acetylcholine receptor M3
CHEMBL245
Ki 5.51 5.51 3081.0 1
Muscarinic acetylcholine receptor M5
CHEMBL2035
Ki 5.5 5.5 3134.0 1
5-hydroxytryptamine receptor 2C
CHEMBL225
Ki 5.44 5.44 3646.0 1
Sodium-dependent dopamine transporter
CHEMBL238
Ki 5.36 5.36 4347.0 1
Muscarinic acetylcholine receptor M5
CHEMBL2035
IC50 5.36 5.36 4362.0 1
Muscarinic acetylcholine receptor M2
CHEMBL211
Ki 5.34 5.34 4590.0 1
D(3) dopamine receptor
CHEMBL234
IC50 5.33 5.33 4712.0 1
Heme oxygenase 2
CHEMBL3348
IC50 5.3 5.3 5000.0 1
Alpha-1A adrenergic receptor
CHEMBL319
Ki 5.27 5.27 5374.0 1
Sodium-dependent dopamine transporter
CHEMBL238
IC50 5.26 5.26 5472.0 1
Muscarinic acetylcholine receptor M1
CHEMBL216
IC50 5.24 5.24 5709.0 1
Sodium-dependent serotonin transporter
CHEMBL228
Ki 5.22 5.22 6086.0 1
5-hydroxytryptamine receptor 2C
CHEMBL225
IC50 5.16 5.16 6961.0 1
Alpha-1D adrenergic receptor
CHEMBL223
Ki 5.15 5.15 7070.0 1
Alpha-1B adrenergic receptor
CHEMBL315
Ki 5.1 5.1 7915.0 1
5-hydroxytryptamine receptor 2A
CHEMBL224
IC50 5.09 5.09 8175.0 1
Nuclear receptor subfamily 1 group I member 2
CHEMBL3401
EC50 5.05 4.95 8900.0 2
Nuclear receptor subfamily 1 group I member 2
CHEMBL2146315
EC50 5.04 5.04 9100.0 1
Tyrosine-protein kinase Fyn
CHEMBL1841
IC50 4.96 4.96 10896.0 1
Sodium-dependent serotonin transporter
CHEMBL228
IC50 4.94 4.94 11456.0 1
SARS-CoV-2
CHEMBL4303835
IC50 4.92 4.855 11920.0 2
Muscarinic acetylcholine receptor M2
CHEMBL211
IC50 4.89 4.89 12909.0 1
D(1A) dopamine receptor
CHEMBL2056
Ki 4.89 4.89 12740.0 1
Alpha-1A adrenergic receptor
CHEMBL319
IC50 4.88 4.88 13278.0 1
Muscarinic acetylcholine receptor M4
CHEMBL1821
IC50 4.86 4.86 13714.0 1
Alpha-1B adrenergic receptor
CHEMBL315
IC50 4.84 4.84 14299.0 1
Muscarinic acetylcholine receptor M3
CHEMBL245
IC50 4.84 4.84 14537.0 1
Alpha-1D adrenergic receptor
CHEMBL223
IC50 4.84 4.84 14385.0 1
5-hydroxytryptamine receptor 4
CHEMBL5017
IC50 4.83 4.83 14780.0 1
Acetylcholinesterase
CHEMBL220
IC50 4.67 4.67 21573.0 1
ADMET
CHEMBL612558
EC50 4.62 4.62 24000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Alpha-2C adrenergic receptor Ki = 61.0 nM 7.21 DRUGMATRIX: Adrenergic Alpha-2C radioligand binding (ligand: [3H] MK-912) -
Unchecked Ki = 195.0 nM 6.71 DRUGMATRIX: Sigma2 radioligand binding (ligand: [3H] Ifenprodil) -
Sigma non-opioid intracellular receptor 1 Ki = 214.0 nM 6.67 DRUGMATRIX: Sigma1 radioligand binding (ligand: [3H] Haloperidol) -
Unchecked IC50 = 317.0 nM 6.5 DRUGMATRIX: Sigma2 radioligand binding (ligand: [3H] Ifenprodil) -
Alpha-2A adrenergic receptor Ki = 369.0 nM 6.43 DRUGMATRIX: Alpha-2A adrenergic receptor radioligand binding (ligand: MK-912) -
Trypanosoma cruzi EC50 = 400.0 nM 6.4 Antitrypanosomal activity against Trypanosoma cruzi amastigotes infected in BESM... 20547819
Heme oxygenase 1 IC50 = 410.0 nM 6.39 Inhibition of rat spleen microsome HO-1 preincubated for 10 mins followed by bet... 31550661
Alpha-2C adrenergic receptor IC50 = 418.0 nM 6.38 DRUGMATRIX: Adrenergic Alpha-2C radioligand binding (ligand: [3H] MK-912) -
Sigma non-opioid intracellular receptor 1 IC50 = 508.0 nM 6.29 DRUGMATRIX: Sigma1 radioligand binding (ligand: [3H] Haloperidol) -
Alpha-2A adrenergic receptor IC50 = 983.0 nM 6.01 DRUGMATRIX: Alpha-2A adrenergic receptor radioligand binding (ligand: MK-912) -
Alpha-2B adrenergic receptor Ki = 1246.0 nM 5.9 DRUGMATRIX: Alpha-2B adrenergic receptor radioligand binding (ligand: Rauwolscin... -
Muscarinic acetylcholine receptor M1 Ki = 1375.0 nM 5.86 DRUGMATRIX: Muscarinic M1 radioligand binding (ligand: [3H] N-Methylscopolamine) -
Unchecked Ki = 1484.0 nM 5.83 DRUGMATRIX: Imidazoline I2, Central radioligand binding (ligand: [3H] Idazoxan) -
D(3) dopamine receptor Ki = 1600.0 nM 5.8 DRUGMATRIX: Dopamine D3 radioligand binding (ligand: [3H] Spiperone) -
Muscarinic acetylcholine receptor M4 Ki = 1913.0 nM 5.72 DRUGMATRIX: Muscarinic M4 radioligand binding (ligand: [3H] N-Methylscopolamine) -
Unchecked IC50 = 2226.0 nM 5.65 DRUGMATRIX: Imidazoline I2, Central radioligand binding (ligand: [3H] Idazoxan) -
5-hydroxytryptamine receptor 2A Ki = 2336.0 nM 5.63 DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2A radioligand binding (ligand: ... -
Polyunsaturated fatty acid lipoxygenase ALOX15 IC50 = 2446.0 nM 5.61 DRUGMATRIX: Lipoxygenase 15-LO enzyme inhibition (substrate: Linoleic acid) -
5-hydroxytryptamine receptor 4 Ki = 2463.0 nM 5.61 DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT4 radioligand binding (ligand: [... -
Unchecked Ki = 2602.0 nM 5.58 DRUGMATRIX: Sodium Channel, Site 2 radioligand binding (ligand: [3H] Batrachotox... -

Literature References

PubMed DOI Target Context # Activities
16472241 10.2174/1570163043334794 Hepatotoxicity 18
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
20966043 10.1124/dmd.110.035105 Nuclear receptor subfamily 1 group I member 2 8
6834396 10.1021/jm00358a032 Trichophyton benhamiae 4
- 10.6019/CHEMBL4651402 SARS-CoV-2 4
6834396 10.1021/jm00358a032 Cavia porcellus 4
6834396 10.1021/jm00358a032 Saprolegnia 4
6834396 10.1021/jm00358a032 Unchecked 4
6834396 10.1021/jm00358a032 Aspergillus fumigatus 4
6834396 10.1021/jm00358a032 Sporothrix schenckii 4
6834396 10.1021/jm00358a032 Phialophora verrucosa 4
6834396 10.1021/jm00358a032 Candida tropicalis 4
6834396 10.1021/jm00358a032 Candida albicans 4
6834396 10.1021/jm00358a032 Cryptococcus neoformans 4
6834396 10.1021/jm00358a032 Trichophyton rubrum 4
6834396 10.1021/jm00358a032 Microsporum canis 4
6834396 10.1021/jm00358a032 Rattus norvegicus 2
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
- 10.1101/2020.03.25.008482 Vero C1008 2
- 10.1101/2020.03.25.008482 SARS-CoV-2 2

Data from ChEMBL 36 via Core Engine