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Identification
Name Terconazole
Accession Number DB00251 (APRD00659)
Type small molecule
Groups approved
Description

Terconazole is an anti-fungal medication, primarily used to treat vaginal fungal infections. [Wikipedia]
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  • Triaconazole
Synonyms
Triaconazole
Salts Not Available
Brand names
Name Company
Fungistat
Gyno-Terazol
Terazol
Terazol 3
Terazol 7
Tercospor
Brand mixtures Not Available
Categories
  • Antifungals
  • Antifungal Agents
CAS number 67915-31-5
Weight Average: 532.462
Monoisotopic: 531.180395297
Chemical Formula C26H31Cl2N5O3
InChI Key InChIKey=BLSQLHNBWJLIBQ-OZXSUGGESA-N
InChI
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
Plain Text
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
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
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Organic
Classes
  • Benzyl Alcohols and Derivatives
  • Phenols and Derivatives
  • Ethers
  • Phenethylamines
  • Anisoles
Substructures
  • Glycerol and Derivatives
  • Benzyl Alcohols and Derivatives
  • Acetals and Derivatives
  • Phenols and Derivatives
  • Aliphatic and Aryl Amines
  • Triazoles
  • Piperazines
  • Ethers
  • Benzene and Derivatives
  • Aryl Halides
  • Halobenzenes
  • Dioxoles
  • Phenethylamines
  • Heterocyclic compounds
  • Aromatic compounds
  • Anisoles
  • Cyanamides
  • Phenyl Esters
  • Anilines
Pharmacology
Indication For the treatment of candidiasis (a yeast-like fungal infection) of the vulva and vagina.
Pharmacodynamics Terconazole is a triazole antifungal agent available for intravaginal use. It is structurally related to imidazole-derivative antifungal agents, although terconazole and other triazoles have 3 nitrogens in the azole ring. By inhibiting the 14-alpha-demethylase (lanosterol 14-alpha-demethylase), Terconazole inhibits ergosterol synthesis. Depletion of ergosterol in fungal membrane disrupts the structure and many functions of fungal membrane leading to inhibition of fungal growth.
Mechanism of action Terconazole may exert its antifungal activity by disrupting normal fungal cell membrane permeability. Terconazole and other triazole antifungal agents inhibit cytochrome P450 14-alpha-demethylase in susceptible fungi, which leads to the accumulation of lanosterol and other methylated sterols and a decrease in ergosterol concentration. Depletion of ergosterol in the membrane disrupts the structure and function of the fungal cell leading to a decrease or inhibition of fungal growth.
Absorption Following intravaginal administration of terconazole in humans, absorption ranged from 5-8% in three hysterectomized subjects and 12-16% in two non-hysterectomized subjects with tubal ligations
Volume of distribution Not Available
Protein binding 94.9%
Metabolism Systemically absorbed drug appears to be rapidly and extensively metabolized. Terconazole primarily undergoes oxidatative N- and O-dealkylation, dioxolane ring cleavage, and conjugation.
Route of elimination Following oral (30 mg) administration of 14C-labelled terconazole, excretion of radioactivity was both by renal (32-56%) and fecal (47-52%) routes.
Half life 6.9 hours (range 4.0-11.3)
Clearance Not Available
Toxicity The oral LD50 values were found to be 1741 and 849 mg/kg for the male and female in rat.
Affected organisms
  • Fungi
Pathways Not Available
Pharmacoeconomics
Manufacturers
  • Ortho mcneil janssen pharmaceuticals inc
  • Altana inc
  • Nycomed us inc
  • Taro pharmaceuticals usa inc
  • Ortho mcneil janssen pharmaceutical inc
  • Perrigo new york inc
Packagers
Dosage forms
Form Route Strength
Bead Intravaginal
Cream Intravaginal
Prices
Unit description Cost Unit
Terazol 3 0.8% Cream 20 gm Tube 55.99 USD tube
Terazol 7 0.4% Cream 45 gm Tube 54.0 USD tube
Terazol 3 3 80 mg Suppository Box 53.99 USD box
Terconazole 3 80 mg Suppository Box 50.9 USD box
Terconazole 0.4% Cream 45 gm Tube 42.57 USD tube
Terconazole 0.8% Cream 20 gm Tube 42.57 USD tube
Terazol 3 cream 2.64 USD g
Zazole 0.8% vaginal cream 2.54 USD g
Terconazole 0.8% cream 2.35 USD g
Terazol 7 cream 1.17 USD g
Terconazole 0.4% cream 0.96 USD g
First Prev Next Last
Patents Not Available
Properties
State solid
Melting point 126.3oC
Experimental Properties
Property Value Source
logP 4.5 PhysProp
Predicted Properties
Property Value Source
water solubility 1.16e-02 g/l ALOGPS
logP 4.58 ALOGPS
logP 5.37 ChemAxon Molconvert
logS -4.7 ALOGPS
pKa 0 ChemAxon Molconvert
hydrogen acceptor count 7 ChemAxon Molconvert
hydrogen donor count 0 ChemAxon Molconvert
polar surface area 64.88 ChemAxon Molconvert
rotatable bond count 8 ChemAxon Molconvert
refractivity 153.19 ChemAxon Molconvert
polarizability 56.15 ChemAxon Molconvert
References
Synthesis Reference Not Available
General Reference Not Available
External Links
Resource Link
KEGG Drug D00888 Link_out
KEGG Compound C08080 Link_out
PubChem Compound 441383 Link_out
PubChem Substance 46505257 Link_out
ChemSpider 390122 Link_out
Therapeutic Targets Database DAP000629 Link_out
PharmGKB PA451618 Link_out
Drug Product Database 2247651 Link_out
RxList http://www.rxlist.com/cgi/generic/tercon.htm Link_out
Drugs.com http://www.drugs.com/cdi/terconazole-cream.html Link_out
PDRhealth http://www.pdrhealth.com/drug_info/rxdrugprofiles/drugs/ter1436.shtml Link_out
Wikipedia http://en.wikipedia.org/wiki/Terconazole Link_out
ATC Codes
  • G01AG02
AHFS Codes
  • 84:04.08.08
PDB Entries Not Available
FDA label show (33.8 KB)
MSDS Not Available
Interactions
Drug Interactions Searched, but no interactions found.
Food Interactions Not Available
Targets

1. Cytochrome P450 51

Pharmacological action: yes
Actions: antagonist

Catalyzes C14-demethylation of lanosterol which is critical for ergosterol biosynthesis. It transforms lanosterol into 4,4'-dimethyl cholesta-8,14,24-triene-3-beta-ol

Organism class: fungal
UniProt ID: P10613 Link_out
Gene: ERG11
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Vanden Bossche H, Marichal P: Mode of action of anti-Candida drugs: focus on terconazole and other ergosterol biosynthesis inhibitors. Am J Obstet Gynecol. 1991 Oct;165(4 Pt 2):1193-9. Pubmed
  2. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. Pubmed
  3. Cauwenbergh G, Vanden Bossche H: Terconazole. Pharmacology of a new antimycotic agent. J Reprod Med. 1989 Aug;34(8 Suppl):588-92. Pubmed
Comments
Drug created on June 13, 2005 07:24 / Updated on February 14, 2012 11:40