Triaconazole

Base Information

• Chemical Name: Triaconazole
• CAS No.: 67915-31-5
• Molecular Formula: C26H31 Cl2 N5 O3
• Molecular Weight: 532.47
• Hs Code.: 2934990002
• NSC Number: 331942
• DSSTox Substance ID: DTXSID40860847
• Wikidata: Q27156516
• ChEMBL ID: CHEMBL1714574
• Mol file: 67915-31-5.mol

Synonyms: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;Fungistat;Gyno-Terazol;R 42470;Terazol;terconazole

Chemical Property of Triaconazole

Chemical Property:

• Vapor Pressure: 1.91E-18mmHg at 25°C
• Melting Point: 126.3 ºC
• Boiling Point: 681.8°Cat760mmHg
• PKA: 8.33±0.10(Predicted)
• Flash Point: 366.2°C
• PSA: 64.88000
• Density: 1.35g/cm³
• LogP: 4.46560
• Storage Temp.: 2-8°C
• Solubility.: DMSO: soluble1mg/mL
• XLogP3: 4.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 8
• Exact Mass: 531.1803953
• Heavy Atom Count: 36
• Complexity: 693

Purity/Quality:

99% ^*data from raw suppliers

Terconazole ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38-53
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)N1CCN(CC1)C2=CC=C(C=C2)OCC3COC(O3)(CN4C=NC=N4)C5=C(C=C(C=C5)Cl)Cl
• Description: Terconazole is an antifungal agent somewhat more potent than clotrimazole and useful in the topical treatment of vaginal dermatophytosis and candidiasis. Terconazole 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.
• Uses: Terazol (Ortho-McNeil). Terconazole 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.
• Indications: Terconazole (Terazol) is a fungicidal triazole topical preparation effective against many Candida strains. It is used as either a 3-day or a 7-day course (Terazol 7—0.4% cream for 7 days or Terazol 3—0.8% cream for 3 days).
• Therapeutic Function: Antifungal
• Clinical Use: cis-1-[4-[[2-(2,4-Dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl)methoxy]phenyl]-4-(1methylethyl)piperazine (Terazol), or terconazole, is a triazolederivative that is used exclusively for the control ofvulvovaginal moniliasis caused by C. albicans and otherCandida species. It is available in creams containing 0.4%and 0.8% of the free base intended for 7-day and 3-day treatmentperiods, respectively. Suppositories containing 80 mgof the free base are also available.

Technology Process of Triaconazole

There total 5 articles about Triaconazole which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

4-(p-methoxyphenyl)piperazine dihydrochloride (38869-47-5,70849-64-8) → (+/-)-Terconazole (67915-31-5,1486497-66-8)

Guidance literature:

Multi-step reaction with 3 steps

1: H₂, NaOAc / 10percent Pd/C / methanol

2: 85 percent / 48percent HBr / Heating

3: 1.) NaH / 1.) Me₂SO, 1 h, 2.) Me₂SO, 80 deg C, 4 h

With hydrogen bromide; hydrogen; sodium acetate; sodium hydride; palladium on activated charcoal; In methanol;

DOI:10.1021/jm00358a032

Reference yield:

(+/-)-cis-[2-(bromomethyl)-2-(2,4-dichlorophenyl)-1,3-dioxolane-4-yl]methyl benzoate (61397-56-6) → (+/-)-Terconazole (67915-31-5,1486497-66-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) NaH, 3.) aq. NaOH

2: 87 percent / pyridine

3: 1.) NaH / 1.) Me₂SO, 1 h, 2.) Me₂SO, 80 deg C, 4 h

With pyridine; sodium hydroxide; sodium hydride;

DOI:10.1021/jm00358a032

Reference yield:

cis-2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolane-4-methanol (67914-85-6) → (+/-)-Terconazole (67915-31-5,1486497-66-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 87 percent / pyridine

2: 1.) NaH / 1.) Me₂SO, 1 h, 2.) Me₂SO, 80 deg C, 4 h

With pyridine; sodium hydride;

DOI:10.1021/jm00358a032

upstream raw materials:

cis-[2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methyl methanesulfonate

4-(4-hydroxyphenyl)-1-(1-methylethyl)piperazine

4-(p-methoxyphenyl)piperazine dihydrochloride

(+/-)-cis-[2-(bromomethyl)-2-(2,4-dichlorophenyl)-1,3-dioxolane-4-yl]methyl benzoate

Refernces