Basic information
- CAS
67915-31-5- Standard SMILES
CC(C)N1CCN(c2ccc(OCC3COC(Cn4cncn4)(c4ccc(Cl)cc4Cl)O3)cc2)CC1- InChIKey
BLSQLHNBWJLIBQ-UHFFFAOYSA-N- Molecular formula
- C26H31Cl2N5O3
- Average molar mass
- 532.5 g/mol
- Monoisotopic mass
- 531.1803953
Overview
1-(4-{[2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)-4-isopropylpiperazine is a dioxolane that is 1,3-dioxolane which is substituted at positions 2, 2, and 4 by 2,4-dichlorophenyl, 1H-1,2,4-triazol-1-ylmethyl, and [4-(4-isopropylpiperazin-1-yl)phenoxy]methyl groups, respectively. It is a dichlorobenzene, an aromatic ether, a member of triazoles, a dioxolane, a N-alkylpiperazine, a N-arylpiperazine and a cyclic ketal.
Names & identifiers
- Preferred name
- 1-(4-((2-(2,4-Dichlorophenyl)-2-((1H-1,2,4-triazol-1-yl)methyl)-1,3-dioxolan-4-yl)methoxy)phenyl)-4-(propan-2-yl)piperazine
- IUPAC
- 1-[4-[[2-(2,4-dichlorophenyl)-2-(1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]-4-propan-2-ylpiperazine
- English name
- Terconazole
- Molecular formula
- C26H31Cl2N5O3
- Molecular weight
- 532.46
Names & synonyms
RefChem:935031DTXCID20209952DTXSID408608471-(4-((2-(2,4-Dichlorophenyl)-2-((1H-1,2,4-triazol-1-yl)methyl)-1,3-dioxolan-4-yl)methoxy)phenyl)-4-(propan-2-yl)piperazineMLS002701820Terconazole EP Impurity A1-(4-{[2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)-4-isopropylpiperazinerel-(2S,4S)-TerconazoleC26H31Cl2N5O3SCHEMBL5008913CHEMBL1714574SCHEMBL18258318
Show more names
Terazol 3TriaconazoleR42470FungistatTerazol 7TERCONAZOLETerconagoleGyno-TerazolTerconazole CRSTerconazole (200 mg)
CHEBI:82979BLSQLHNBWJLIBQ-UHFFFAOYSA-NHMS5084M131-[4-[[(2RS,4SR)-2-(2,4-Dichlorophenyl)-2-[(1H-1,2,4triazol-1-yl)methyl]-1,3-dioxolan-4-yl]methoxy]phenyl]-4-(1methylethyl)piperazines50331-[4-[[2-(2,4-dichlorophenyl)-2-(1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]-4-isopropyl-piperazineSMR001565413Q27156516
Properties
Computed structural properties
- XLogP
- 4.8
- Topological polar surface area
- 64.9 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 7
- Rotatable bonds
- 8
- Heavy atoms
- 36
- Formal charge
- 0
- Complexity
- 692
Physicochemical properties
- Melting point
- 126.3 °C · 126.3°C
- Boiling point
- 681.8 · 681.8±65.0 °C(Predicted)
- Density
- 1.35 · 1.35±0.1 g/cm3(Predicted)
- storage temp.
- Inert atmosphere,Room Temperature
- solubility
- 1 mg/mL · DMSO: soluble1mg/mL
- pka
- 8.33 · 8.33±0.10(Predicted)
- form
- powder
- color
- white
- Major Application
- forensics and toxicologyveterinary
- InChIKey
- BLSQLHNBWJLIBQ-GRHWAJSLNA-N
- SMILES
- N1(C2=CC=C(OC[C@H]3CO[C@@](C4=CC=C(Cl)C=C4Cl)(CN4C=NC=N4)O3)C=C2)CCN(C(C)C)CC1 |&1:7,10,r|
- CAS DataBase Reference
- 67915 · 67915-31-5(CAS DataBase Reference)
- FDA UNII
- 0 KJ2VE664U · 0KJ2VE664U
- ATC code
- 1 AG02 · G01AG02
- UNSPSC Code
- 41116107 · 41116107
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- wgk
- 3
- rtecs
- TL3564600
- hs_code
- 2934990002
- risk_code
- 36/37/38-53
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi
- safety_code
- 26
- Storage Class
- 11 - Combustible Solids
- target organs
- Respiratory system
- Hazard statements
- H315-H319-H335-H413
- Hazard Classifications
- Aquatic Chronic 4Eye Irrit. 2Skin Irrit. 2STOT SE 3
- Precautionary statements
- P261-P305+P351+P338
Chemistry & industry
Applications
DescriptionTerconazole is an antifungal agent somewhat more potent than clotrimazole and useful in the topical treatment of vaginal dermatophytosis and candidiasis.
DescriptionTerconazole is an orally bioavailable broad-spectrum triazole antifungal agent that completely inhibits growth of T. rubrum, M. audouini, M. canis, and T. verrucosum, as well as some C. albicans and A. fumigatus strains and other fungi when used at a concentration of 100 μg/ml. It also has bacteriostatic activity against E. coli, P. aeruginosa, S. aureus, and S. pyogenes when used at a concentration of 100 μg/ml. Terconazole eliminates vaginal C. albicans candidiasis infection in 97% of rats when administered as a 1% topical ointment and in 50% of rats when orally administered at a dose of 10 mg/kg. It inhibits cytochrome P450 (CYP) isoforms involved in ergosterol biosynthesis, interfering with fungal cell membranes. It decreases synthesis of 14α-desmethyl sterols and increases synthesis of methylated sterols in C. albicans (IC50 = 3 nM). Formulations containing terconazole have been used in the treatment of candidiasis of the vulva and vagina.
UsesTerazol (Ortho-McNeil).
UsesTerconazole belongs to a new chemical class of antifungal agents, the triazoles. Terconazole has a far greater selectively for yeast cytochrome P-450 than for mammalian microsomal cytochrome P-450 and is used as topical treatment of mycotic vaginitis. Terconazole may also be used in vitro as a potent antifungal agent to prevent the morphogenetic transformation of yeast into (pseudo-)mycelium form of Candida albicans.
Upstream & downstream products
Upstream raw materials
Suppliers100 total
国药集团化学试剂有限公司86-21-63210123 · [email protected]
Related reactions
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Compound notes
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